Natural products (NPs) have been regarded to be greatly beneficial to human health and as important resources for drug discovery. One of the prominent events in 2015 was that the Noble Prize in Physiology or Medicine was awarded to an eminent Chinese scholar, Professor TU You-You, for the discovery of artemisinin (Qing-Hao-Su) as an effective chemotherapy against falciparum malaria. NPs research and development went to the limelight of the world once again. In fact, Mother Nature is still the best chemist, and is still a non-exhausted source for new pharmacophores. New separation and analytical systems have reduced research cost and shortened timeline nowadays, especially for those novel NPs with mass-limited materials. Unprecedented NPs will remain to be the important source of new chemical entities (NCE) and novel drug candidates.
Undoubtedly, China has become the strong force in NPs research in recent years. As far as publications are concerned, peer-reviewed articles from China are often ranked the first in most international journals in this field, such as Journal of Natural Products, Organic Letters, Phytochemistry, Tetrahe dron and Planta Med ica. For example, Chinese scholars (i.e., both the corresponding author's and the first author's affiliations belong to China) published 112, 103, and 103 papers in Journal of Natural Products in 2015, 2016 and 2017, respectively, accounting for about 1/4 of the journal publications.
This review sums up the remarkable new findings from characteristic NPs chemistry investigations made by domestic scholars in China over a three-year period, i.e., 2015 through 2017. In order to accomplish this task, the main databases such as SciFinder Scholar, PubMed, Web of Science, China Knowledge Resource Integrated Database, Wanfang Data and VIP China Science and Technology Journal Database have been thoroughly investigated. For example, we took the following strategies in searching SciFinder Scholar: at the advanced search interface, we put "new compounds from (natural sources)", "chemical constituents from (natural sources)" or "isolation and structure elucidation" as research topic respectively, the [publication years] were set as 2015-2017, and the [company] was designated as China. The search term "new compounds" could be replaced by "novel compounds", "unusual compounds", "undescribed compounds", "rare compounds", or "novel structures" for further search. Meanwhile, we also searched SciFinder Scholar by journal names, including Journal of Natural Products, Organic Letters, Journal of Organic Chemistry, Journal of the American Chemical Society, Angewandte Chemie-International Edition, Phytochemistry, Phytochemistry letters, Tetrahedron, Tetrahedron letters, RSC Advances, Planta Med ica, etc. To avoid omitting important papers, some specific words such as "alkaloids", "terpenoids", "flavonoids" were also tried in the searches. The retrieved references have been analyzed one by one. Both the unrelated search results and duplicates were removed. Thus, 1479 papers in English and 332 papers in Chinese were collected. In particular, newly discovered compounds containing unusual complex structures and/or exhibiting promising bioactivities were hand-picked. As a result, 320 selected compounds from 277 papers, organized on the basis of their chemical structure classes and novelties, were illustrated in this review article.Newly Discovered Natural Products: Phytochemistry, Pharmacology, and Biological Activities Terpenoids Monoterpenoids
A new iridoid glucoside, 5-[3-(1-hydroxyethyl) pyridine], 7-loganin ester (1), has been identified from the aerial parts of Pterocephalus hookeri . An unusual secoiridoid trimer, named sweriyunnanlactone A (2), was isolated from Swertia yunnanensis under the guidance of LC-MS analysis. Compound 2 was the first example of secoiridoid trimer featuring a C28 skeleton, showing weak inhibition on HBV DNA replication with an IC50 of 60.76 μmol·L-1 (Selective index = 12.6) on HepG 2.2.15 cell line in vitro .Sesquiterpenoids
8α-Hydroxy-T-muurolol (3) has been isolated from the aerial parts of Chimonanthus salicifolius. It shows significantly immunosuppressive activity in a dose-dependent manner . Kadcoccinin A (4), a cage-like sesquiterpenoid possessing a tricyclo[4.4.0.03, 10]decane scaffold from the stems of Kadsura coccinea, exhibits weak antifungal effects against Fusarium oxysporum, Gaeumannomyces graminis, and Verticillium cinnabarium . Norxanthantolide F (5) has been isolated from the fruits of Xanthium sibiricum. It exhibits antiinflammatory activity by suppressing the lipopolysaccharide (LPS)- induced nitric oxide (NO) production in BV2 microglial cells, with an IC50 of 3.0 μmol·L-1. A phytochemical investigation on the whole plant of Salvia substolonifera has yielded seven germacrane sesquiterpenoids. Among them, substolide G (6) significantly inhibits the VEGF-induced human umbilical vein endothelial cell (HUVEC) proliferation in vitro (IC50 16.1 μmol·L-1) . Cernuumolide H (7), a highly oxygenated germacranolide isolated from Carpesium cernuum, exhibits moderate cytotoxic effects against four tumor cell lines with IC50 ranging from 0.87 to 2.02 μmol·L-1 . Two rare rearranged cuparane-type sesquiterpenoids, beshanzuenones A (8) and B, have been isolated from the shed trunk barks of Abies beshanzuensis, a critically endangered plant native to China.They show considerable activity against influenza virus A (H3N2) . A few novel bisabolene-derived sesquiterpenoids have been isolated from the roots of Artabotrys hexapetalus. Among them, artaboterpenoid A (9) featured a novel carbon skeleton with a new C (2)—C (10) linkage; artaboterpenoid B was obtained as a pair of enantiomers. Moreover, (—)-8R-artaboterpenoid B (10) exhibited cytotoxic effects against HCT- 116, HepG2, A2780, NCI-H1650, and BGC-823 cell lines with IC50 ranging from 1.38 to 8.19 μmol·L-1 . Nine new humulane-derived sesquiterpenoids have been isolated from the Antarctic fungus Aspergillus ochraceopetaliformis SCSIO 05702. Among them, ochracenes A (11) and B (12) featured novel carbon skeletons with corresponding methyl migration and ring cleavage. Moreover, Compound 12 exhibits inhibitory effect on LPS-induced NO release in RAW 264.7 cells with an IC50 of 14.6 ± 0.5 μmol·L-1 . Wilfolide A (13), a rare humulanolide with an unusual bicyclo [6.3.0] undecane core and an adjoining butyrolactone moiety, has been isolated from the roots of Cynanchum wilfordii. It exhibits weak acetylcholinesterase (AChE) inhibitory activity . Dysifragilone A (14), with a rearranged avarone skeleton, has been isolated from the South China Sea sponge Dysidea fragilis. This compound shows potent inhibitory activity against the production of NO stimulated by LPS in mouse RAW264.7 cells, with an IC50 of 6.61 μmol·L-1 . Chermesin A (15), a drimane-type sesquiterpene, has been isolated and identified from the culture extract of Penicillium chermesinum EN-480, an endophytic fungus obtained from the inner tissue of the marine red alga Pterocladiella tenuis. It exhibits antibacterial activity against the opportunistic pathogen Micrococcus luteus, with an MIC value of 8 μg·mL-1. Another drimane-type sesquiterpenoid named polymorphine B (16) has been obtained from the ethyl acetate (EtOAc) extract of fermentation broth of fungus Xylaria polymorpha. It exhibits anti-acetylcholinesterase and α-glucosidase inhibitory activites . Daphnauranin A (17), a sesquiterpene with an unprecedented 5/7 oxacycloheptane ring system, has been isolated from the roots of Daphne aurantiaca. It shows anti-insect activity against male fruit fly with anti-feeding rate up to 46.2% ± 7.1% at 1 mmol·L-1 . A rare carotane-type sesquiterpene, forkienin A (18), has been isolated from the twigs and leaves of Fokienia hodginsii . Plebein A (19), a sesquiterpene with a novel skeleton has been isolated from the whole plant of Salvia plebeia . Illisimonin A (20), an unprecedented sesquiterpene with a tricyclo [5.2.1.01, 6] decane skeleton, has been isolated from the fruits of Illicium simonsii. It shows neuroprotective effect against oxygen-glucose deprivation (OGD)-induced cell injury in SHSY5Y cells with an EC50 of 27.72 μmol·L-1 . Aromaticane A (21), an unprecedented guaiane-type sesquiterpene with unique cyclopropane and furan functionalities, has been isolated from the radix of Curcuma aromatica. It exhibits notable antioxidant effect on oxidative injury induced by H2O2 . Nicotabin A (22), a sesquiterpene derivative possessing a fused 5/6/5/5/5 ring system, has been isolated from leaves of Nicotiana tabacum. It inhibits NO production in LPS-activated RAW264.7 macrophages with an IC50 of 22.1 μmol·L-1 . Commiphorane C (23), isolated from Resina Commiphora, possesses a 5/6/7 backbone. Biological evaluation reveals that compound 23 can significantly attenuate overproduction of fibronectin, collagen I, and α-SMA in TGF-β1-induced rat renal proximal tubular cells .Dimeric sesquiterpenoids
Three cadinane dimers with multiple contiguous quarternary carbons have been isolated from the rhizomes of Stahlianthus involucratus. Among them, involucratustone A (24) is a rearranged homodimer of cadinane sesquiterpene fused with a unique fully substituted 1-oxaspiro[4.4]nonane core, which is obtained for the first time in nature. It exhibits potent cytotoxic activity. Meanwhile, involucratustone C (25), a novel 3′, 4′-seco-cadinane-dimer, possesses notable anti-inflammatory effect . Chlorajaponilide F (26), isolated from the whole plant of Chloranthus japonicus (Chloranthaceae), is effective against wild type HIV-1 replication with an EC50 of 3.08 μmol·L-1. It has also been found to show inhibitory effects on two NNRTI-resistant HIV strains . Fortunilide A (27) is a dimeric lindenane-type sesquiterpene isolated from Chloranthus fortunei. It is noticeable that 27 exhibits low nanomolar activity against chloroquine-resistant Plasmodium falciparum with the IC50 of 5.2 ± 0.6 nmol·L-1, which is comparable to the potency of artemisinin (IC50 4.0 ± 4.2 nmol·L-1) . Fortunoid B (28), representing the first example of the heterodimer of a lindenane and a eudesmane sesquiterpene, has been also isolated from C. fortunei. It shows moderate antimalarial activity . Eleven new sesquiterpene dimers have been isolated from the seeds of Sarcandra glabra. Among them, sarglabolide A (29) has been verified to exclusively possess a seventeen-membered macrocyclic ester ring formed by the scaffold of the sesquiterpene dimer and small organic acids. It can significantly inhibit NO production in LPS-induced macrophages, with an IC50 of 3.04 μmol·L-1. Guaianodilactone B (30), a guaianoid dimer from Carpesium faberi, exhibits potent cytotoxicity against human leukemia (CCRF-CEM) cells with an IC50 of 2.03 μmol·L-1. This compound may be served as a promising lead for a new class of antileukemic agent . Another guaianoid dimer, namely selengsisnin A (31), has been isolated and identified from Artemisia selengensis .
Dicarabrone A (32), possessing a new skeleton featuring a cyclopentane ring connecting two sesquiterpene lactone units, has been isolated from the whole plant of Carpesium abrotanoides. It shows moderate effect on HL-60 cells, with an IC50 of 9.1 μmol·L-1. A phytochemical investigation of the whole plant of Ligularia pleurocaulis has led to the isolation of an eremophilenolide dimer named biligupleurolide (33), which shows moderate growth inhibitory activities against MCF-7, HepG2, and A549 . Sterhirsutin C (34), a new heterodimeric sesquiterpene from the culture of Stereum hirsutum, shows cytotoxicities against K562 and HCT116 cell lines . Xylopiana A (35), a dimeric guaiane, has been isolated from the leaves of Xylopia vielana . Artemisian B (36), the first example of [4 + 2] Diels—Alder type adducts presumably biosynthesized from a rare 1, 10 : 4, 5-di-seco- guaianolide and a guaianolide diene, has been isolated from the traditional Chinese medicine Artemisia argyi. It exhibits significant antiproliferative activity via apoptosis induction and G2/M arrest in MDA-MB-468 cells, with an IC50 of 3.21 μmol·L-1.Diterpenoids
Lagoditerpene A (37) has been isolated from a Labiatae plant, Lagochilus platyacanthus. It shows moderate hemostatic activity by shortening the values of activated partial thromboplastin time . An architecturally complex spiroketal diterpenoid, leonuketal (38), has been isolated from the aerial parts of the plant Leonurus japonicas. It shows significant vasorelaxant activity against KCl-induced contraction of rat aorta, with the EC50 of 2.32 μmol·L-1. Two labdane-type diterpenoids, haplomintrins A (39) and B with six rings system, have been isolated from a Chinese liverwort Haplomitrium mnioides . Chlorabietin C (40) has been isolated from the roots of Chloranthus oldhamii, a rare Chloranthaceae plant, endemic to China. It shows anti-neuroinflammatory effect by inhibiting NO production in LPS- activated murine BV-2 microglial cells (IC50 16.4 μmol·L-1) . Nepetaefolin F (41) has been isolated from the whole plant of Caryopteris nepetaefolia. It shows higher cytotoxicity than paclitaxel in one nonsmall-cell lung cancer, patient-derived xenograft (PDX) model when tested using PDX models and the adenosine triphosphate-tumor chemosensitivity assay (ATP- TCA) with an IC50 of 6.3 μmol·L-1 . The phytochemical study of Pedilanthus tithymaloides has led to the isolation of eight new and five known jatrophane diterpenoids. Subsequent structural modification has yielded 22 new derivatives. Compound 42, one of the derivatives, exhibits a remarkable metabolic stability in vitro and a favorable antitumor effect in vivo .
A phytochemical investigation of the hydrophobic extract of Rabdosia serra (Lamiaceae family) has led to the isolation of two types of ent-6, 7-secokaurane diterpenoids, ent-6, 20-epoxy-6, 7-secokaur-1, 7-olide and ent-6, 7-secokaur-7, 20- olide illustrated by rabdosins E (43) and K (44), respectively . Pierisketolide A (45), an unusual A-homo-B-nor-ent- kaurane carbon skeleton, has been isolated from the roots of Pieris formosa. It exhibits an analgesic effect with a 45% writhe inhibition rate at a dose of 10.0 mg·kg-1. Scopariusol A (46), the first ent- kaurane diterpenoid featuring a 1, 11-ether bridge, together with a dimeric ent-kaurane scopariusol I (47), has been isolated from the aerial parts of Isodon scoparius . An unprecedented 7, 8 : 15, 16-di-seco-15-nor-21-homo-ent- kauranoid, named laxiflorol A (48), has been isolated from the leaves of Isodon eriocalyx var. laxiflora . Stelleralide F (49), obtained from the roots of Stellera chamaejasme, exhibits extremely potent anti-HIV activity in an in vitro assay against NL4-3 virus replication in MT4 lymphocytes, with an EC50 of 0.93 nmol·L-1 . Chinensipene B (50) from Trigonostemon chinensis has been demonstrated to have inhibitory effect on LPS-induced NO production, with the IC50 of 10.2 μmol·L-1 . Rhodomollacetal A (51), possessing a 2, 3 : 5, 6-di-seco-grayanane carbon skeleton, has been isolated from the leaves of Rhododendron molle . Rhodomollanol A (52), a highly oxygenated diterpene, has been also isolated from the same plant. It exhibits moderate PTP1B inhibitory activity . Cinnamomols A (53) and B, featuring a cage-like, rigid, and hexacyclic ring system, have been isolated from the leaves of Cinnamomum cassia. It exhibits significant immunostimulative activity . Eleganstone A (54) has been isolated from the marine sponge Dactylospongia elegans and exhibits weak antibacterial activities against E. coli, Bacillus subtilis, and Staphylococcus aureus . Euphordraculoates A (55) and B (56), featuring tigliane diterpenoids with two new carbon skeletons, have been characterized as secondary metabolites from Euphorbia dracunculoides. Compound 56 can inhibit Wnt pathway in a dose- and time-dependent manner . Crotusin C (57), a new tigliane-type diterpenoid isolated from the methanolic extract of the twigs and leaves of Croton caudatus, shows significant inhibitory activities against five human tumor cell lines with IC50 ranging from 0.49 to 4.19 μmol·L-1. Perovskatone B (58), an icetexane-type diterpenoid from Perovskia atriplicifolia, possesses noticeable anti-hepatitis B virus activity in vitro . Eight new cafestol-type diterpenoids have been isolated from the twigs of Tricalysia fruticosa. Among them, tricalysin H (59) can significantly inhibit the NO production in LPS-activated RAW264.7 macrophages, with an IC50 of 6.6 μmol·L-1. Euphomilone A (60), a highly modified ent-rosane-type diterpenoid from the aerial parts of Euphorbia milii, displays inhibition on the receptor activator of nuclear factor-kappaB ligand (RANKL)-induced osteoclast formation (IC50 12.6 μmol·L-1) . Brassicicene M (61), isolated from the fungus Alternaria brassicicola, features a unique tricyclo[9.2.1.03, 7]tetradecane core skeleton . Xishacorene A (62) has been isolated from the Xisha soft coral Sinularia polydactyla. It exhibits an interesting dose-dependent promotion effect on the ConA- induced T lymphocyte proliferation .
Cassane skeletons are rare in nature, but often possess valuable medicinal properties. Neocaesalminin A (63), a furanoditerpenoid with an unusual A-seco-rearranged cassane skeleton, has been isolated from the seeds of Caesalpinia minax . Caesalsappanin H (64), isolated from the seeds of Caesalpinia sappan, displays antimalarial activity against the chloroquine- resistant K1 strain of Plasmodium falciparum, with an IC50 value of 0.52 μmol·L-1. Boscartin A (65) has been isolated from the gum resin of Boswellia carterii. Its antiulcerative colitis activity has been evaluated in an in vitro x-box-binding protein 1 (XBP 1) transcriptional activity assay. Compound 65 significantly activates XBP 1 transcription, with an EC50 of 0.34 μmol·L-1. Scutolide D (66), a new neo-clerodane-type diterpenoid isolated from the whole plant of Scutellaria barbata, exhibits moderate inhibition against Epstein—Barr virus (EBV) lytic replication, with an EC50 of 3.2 μmol·L-1. A phytochemical investigation of the 70% acetone extract of Croton crassifolius roots has afforded eight new diterpenoids. Among them, crassin A (67) is a ring B-rearranged diterpenoid, whereas crassin C (68) is a ring A-rearranged diterpenoid . Aphapolin A (69), a nemoralisin-type diterpenoid, has been isolated from Aphanamixis polystachya (Wall.) R. Parker . Penioxalicin (70), the first 3-nor-2, 3-seco-labdane type diterpene, has been isolated from the fungus Penicillium oxalicum TW01-1. It shows moderate cytotoxicity against HL-60 cell line . Vitepyrroloid A (71), a new labdane diterpenoid containing a 2-cyano-substituted pyrrole-ring, has been isolated from the leaves of Vitex trifolia. It shows cytotoxic activity against a human nasopharyngeal carcinoma cell line (CNE1), with an IC50 of 8.7 μmol·L-1. Chloranhenryin D (72), a rare naturally occurring C-14 norabietane, has been isolated from the whole plant of Chloranthus henryi . Citrinovirin (73), a novel norditerpene with an unprecedented carbon skeleton, has been isolated from the culture of a marine brown alga-endophytic strain (cf-27) of Trichoderma citrinoviride. It inhibits the growth of Staphylococcus aureus, with an MIC value of 12.4 μg·mL-1. Four polycyclic norditerpenoids have been isolated from Cephalotaxus sinensis. Among them, cephalotanins A (74) and C (75) possess two different unprecedented carbon skeletons. Moreover, compound 74 exhibits considerable nuclear factor-kappaB (NF-κB) inhibition with an IC50 of 4.12 μmol·L-1. Cephanolide A (76) has been isolated and characterized from Cephalotaxus sinensis as the first example of A-ring-contracted cephalotane-type dinorditerpenoid . 2β-Hydroxynagilactone L (77), a dinorditerpenoid isolated from the seeds of Podocarpus nagi, shows cytotoxicities against A2780 and HEY cell lines with IC50 of less than 2.5 μmol·L-1. Several new diterpenoids have been isolated from the whole plant of Ligularia fischeri. Fischericin A (78) is a new 15, 16-dinorerythroxylane-type diterpenoid possessing a C18 skeleton; while fischericin B (79) is the first example of a 6/6/6/6/5/5-fused hexacyclic ent-kaurane diterpenoid .
Mannolide A (80), a new kind of diterpenoid featuring a new intact carbon skeleton, has been isolated from Cephalotaxus mannii . Euryachin A (81), a new type of tetracyclic diterpenoid, has been obtained from the branches of Eurya chinensis. It exhibits anti-inflammatory activity with the potency comparable to the positive control L-N-Methylarginine, when evaluating against NO production in LPS-stimulated RAW264.7 cells . Three highly modified diterpenoids, pepluacetal (82), pepluanols A (83) and B (84), have been isolated and identified from Euphorbia peplus. They all inhibit Kv1.3, a validated target for the treatment of autoimmune diseases. Among them, compound 84 is most effective, with an IC50 of 9.50 μmol·L-1 . Sarcophytrol A (85), isolated from the South China Sea soft coral Sarcophyton trocheliophorum, bears a dodecahydrocyclopenta[6, 7]cycloundeca[1, 2-b]oxirene ring system with an unusual 1Z-configuration . Euphorikanin A (86) has been isolated from the roots of Euphorbia kansui and exhibits moderate cytotoxicities against two human tumor cell lines HeLa and NCI-446 . Rhodomollein XXVIII (87), a new grayanoid isolated from the roots of Rhododendron molle, has been demonstrated to have significant antinociceptive activity in an acetic acid-induced writhing test. Furthermore, its analogues, rhodojaponins Ⅲ and Ⅵ, are more potent than morphine in both acute and inflammatory pain models . Six new highly oxygenated polycyclic cyathane-xylosides have been obtained from the cultures of the basidiomycete Cyathus striatus. Of these, striatoid F (88) can dose-dependently enhance nerve growth factor (NGF)- mediated neurite outgrowth in rat pheochromocytoma (PC-12) cells . Perforalactone A (89), a new 20S quassinoid with a unique cage-like 2, 4-dioxaadamantane ring system and a migrated side chain, has been isolated from the plant Harrisonia perforata. It exhibits notable biological properties, including insecticidal activity against Aphis medicaginis Koch and antagonist activity at the nicotinic acetylcholine receptor of Drosophila melanogaster . Vulgarisin B (90) has been isolated from a medicinal plant Prunella vulgaris Linn. It has been demonstrated to have modest cytotoxicity against A549 cells . Commiphorane A (91), a dinorditerpenoid characteristic of a 6/6/6/6 ring system, has been isolated from Resina Commiphora . A dimeric abietane diterpenoid, biteuvisone A (92), has been isolated from the whole plant of Teucrium viscidum . In fact, only about 20 dimeric abietane diterpenoids have been so far reported since 2000. Aphadilactone E (93) has been isolated from Aphanamixis grandifolia. It shows moderate antimalarial activity, with an IC50 of 1.03 μmol·L-1 . Taxodikaloid A (94) has been isolated from the seeds of Taxodium ascendens. It features an unprecedented oxazoline ring linkage connecting two abietane diterpenoid monomers, which shows potential neuroprotective activity against Aβ25—35-induced damage in SH-SY5Y cells . Eupractenoids A (95) and B (96), two heterodimeric diterpenoids comprising abietane lactone and nor-rosane constituent units, have been isolated from the roots of Euphorbia ebracteolata. Compound 95 exhibits a moderate inhibitory effect on α-glucosidase (IC50 7.94 μmol·L-1), with a Ki of 10.8 μmol·L-1. Whereas, compound 96 inhibits the acetyl transfer activity of Mycobacterium tuberculosis GlmU (IC50 41.85 μmol·L-1), a novel tuberculosis treatment target . Neoglaucocalyxin (97), a rare dimer of ent-kauranoid with a cyclobutane ring, has been obtained from the aerial parts of Rabdosia japonica . Birhodomollein A (98) has been isolated from the flowers of Rhododendron molle. It contains a rare chloro- substitution on one of the grayanane moieties .
Erinacine S (99) has been isolated from the ethanol extract of the mycelia of Hericium erinaceus. In a 30-day oral course, compound 99 could attenuate Aβ plaque burden in the brains of 5-month-old female APP/PS1 transgenic mice . Aspterpenacid A (100), with an unusual 5/3/7/6/5 ring system, has been isolated from the mangrove endophytic fungus Aspergillus terreus H010 . Interestingly, aspterpenacid C (101), an analogue of compound 100, has been discovered from the traditional Chinese medicinal plant Swertia bimaculata. Compound 101 exhibits moderate inhibitory activities on NO production (IC50 16.1 μmol·L-1) and HIV-1 replication (EC50 1.35 μmol·L-1) . Sesteralterin (102) has been obtained from the culture extract of an Alternaria alternata strain (k21-1) isolated from the surface of the marine red alga Lomentaria hakodatensis. It represents the first nitidasane sesterterpene naturally produced by fungi . (—)- Hippolide J (103) and its enantiomer, have been isolated from the marine sponge Hippospongia lachne collected from the South China Sea. Both of them have been found to show potent antifungal activities against three strains of hospital-acquired pathogenic fungi (i.e., Candida albicans SC5314, Candida glabrata 537, and Trichophyton rubrum Cmccftla) with MIC50 of 0.125- 0.25 μg·mL-1.Triterpenoids
A phytochemical investigation of the methanolic extract of the fruiting bodies of Fomes officinalis has afforded a number of 24-methyl-lanostane triterpenoids. Among them, officimalonic acid A (104) represents a previously unknown triterpene type with a 24-methyl-7(8→9)abeo-lanostane skeleton; officimalonic acid D (105) shows a potent inhibitory effect (IC50 6.8 μmol·L-1) on NO production in LPS-induced RAW264.7 cells . Tsugalide A (106), a new rearranged lanostane triterpenoid, has been isolated from the MeOH extract of the stem of Tsuga longibracteata . Six lanostane- related triterpenoids have been isolated from Kadsura coccinea. Among them, kadcoccinone A (107) has an infrequent 14 (13→12)-abeo-6/6/5/6-fused rearranged lanostane-type skeleton; kadcoccinone C (108) possesses a novel 6/6/9-fused carbocyclic core containing a rare oxabicyclo [4.3.1] decane system; kadcoccinones D (109) and E represent the first two examples of the 18 (13→12)-abeo-26-norlanostane triterpenoids . Euviscin A (110) has been isolated from the whole plant of Teucrium viscidum. It possesses a rare 7 (8→9)-abeo-9R-D: C-friedo-B′: A′-neo-gammacerane skeleton . Ganoboninone A (111), a new 3, 4-seco-27-norlanostane triterpenoid, has been isolated from the fruiting bodies of the medicinal mushroom Ganoderma boninense. It shows antimalarial effect with an IC50 of 27.36 μmol·L-1 . Balanterpene A (112), featuring a ring-expanded triterpenoid skeleton with the C-19 methyl involved in the ring formation, has been isolated from the leaves of Casearia balansae . Cimiheraclein A (113) has been isolated from the aerial parts of Cimicifuga heracleifolia and exhibits weak inhibitory activity against the STAT 3 signaling pathway . Four iridals with an unprecedented α-terpineol moiety have been isolated from the ethanol extract of rhizomes of Iris tectorum. Among them, polycycloiridal A (114) exhibits pronounced hepatoprotective activity at a concentration of 10 μmol·L-1 . Lancolide E (115), featuring a complex tetracyclo [5.4.0.02, 4.03, 7] undecane-bridged system, has been obtained from a "talented" schinortriterpenoid producer Schisandra lancifolia . Schincalide A (116), a schinortriterpenoid possessing a tricyclo [5.2.1.01, 6]decane- bridged system, has been isolated from the stems and leaves of Schisandra incarnate . Spiroschincarin A (117), featuring a unique 1-oxaspiro[6.6]tridecane motif, has been isolated from the fruits of Schisandra incarnata .
Alismanin A (118), an aromatic triterpenoid with a C34 skeleton, has been isolated from Alisma orientale. It displays significant activation effect on pregnane X receptor (PXR) at 10 nmol·L-1 . Picraquassin A (119), obtained from the stems of Picrasma quassioides, has an unprecedented 21, 24-cycloapotirucallane skeleton . Spirochensilide A (120), isolated from Abies chensiensis, is regarded as the first rearranged triterpenoid skeleton featuring an unprecedented spiro-[5, 6] ring system . Several highly modified triterpenoids have been isolated from Phyllanthus hainanensis. They exhibit exceptionally potent in vitro immunosuppressive activities against the proliferation of T and B lymphocytes. Among them, phainanoid F (121) has been the most potent, with the IC50 of 2.04 nmol·L-1 [positive control cyclosporin A (CsA) 14.21 nmol·L-1] and < 1.60 nmol·L-1 (CsA 352.87 nmol·L-1), respectively . In addition, phainanolide A (122) exhibits remarkable cytotoxic activity against HL-60 cells with an IC50 of 0.079 μmol·L-1 .
Twenty new liminoids have been isolated and identified from Cipadessa cinerascens. Among the isolates, cipacinoid A (123) shows moderate protein tyrosine phosphatase 1B (PTP1B) inhibition ; ciparasins B (124) and P (125) exhibit significant anti-HIV activity with the EC50 of 5.5 μmol·L-1 and 6.1 μmol·L-1, respectively . Fourteen new limonoids have been isolated from the whole plant of Munronia henryi. Among them, munronin A (126) exhibits cytotoxic effects on a small panel of cancer cell lines, with IC50 ranging from 0.4 to 2.3 μmol·L-1; while munronin H (127) shows significant anti-TMV activity, with an IC50 of 19.6 μg·mL-1. Walrobsin A (128) has been isolated from the root barks of Walsura robusta. It shows significant anti-inflammatory activity with an IC50 of 7.8μmol·L-1 and also inhibits the expression of iNOS and IL-1β in a dose- dependent manner . Walsuronoid F (129), featuring an 18 (13/14)-abeo limonoid skeleton, has been isolated from the fruits of Walsura robusta . Trichilia species of the Meliaceae family are well-known for metabolizing structurally diverse limonoids. From the fruits of Trichilia connaroides, several novel ones have been obtained. Among them, spirotrichilin A (130) shows weak anti-inflammatory activity on NO production in LPS-induced RAW264.7 cells . In contrast, trichiconlide A (131) bears an unprecedented 5/6/5/6/5 carbon skeleton; trichiconlide B (132) possesses a cage- like structure located between rings A and C. Furthermore, 131 shows a moderate inhibitory effect on LPS-induced NO production in the RAW264.7 cell line . Triconoids A (133) and D (134), representing two rearranged limonoid skeletons, have been isolated from the leaves and twigs Trichilia connaroides collected from the capital area of Nepal . Chukvelutilide Y (135), a new C-15 enolic acyl phragmalin- type limonoid orthoester, has been isolated from the ethanol extract of seeds of Chukrasia tabularis . Xylomexicanin I (136), a tetranortriterpenoid with bridged B- and C-rings, has been isolated from seeds of the Chinese mangrove, Xylocarpus granatum . Three new ring B-seco limonoids, ciliatonoids A—C, have been isolated from Toona ciliata. Both ciliatonoids A (137) and B possess an unprecedented limonoid architecture, while ciliatonoid C (138) belongs to a rare class of limonoid and displayed modest cytotoxic effects against HL-60 and P-388 cell lines, with IC50 of 1.19 and 2.50 μmol·L-1, respectively . Perforanoid A (139) has been isolated from the leaves of Harrisonia perforata (Blanco) Preliminary studies show that Compound 139 has been cytotoxic towards HEL, K562, and CB3 tumor cell lines, with IC50 of 6.17, 4.24 and 3.91 μmol·L-1, respectively .
Krishnadimer A (140), a C2-symmetric limonoid dimer representing a new class of axially chiral nonbiaryl natural products, has been isolated from the seeds of a mangrove, Xylocarpus moluccensis .Meroterpenoids
(+)-Rhodonoid C (141) and (—)-rhodonoid C, an enantiomeric pair of meroterpenoids isolated from the aerial parts of Rhododendron capitatum, are the first examples of meromonoterpenes incorporating an unprecedented 6/6/6/5 ring system. Compound 141 shows antiviral activity against herpes simplex virus type 1 (HSV-1) in vitro . (±)-rasumatranin A (142), a pair of bibenzyl-based meroterpenoid enantiomers have been isolated from the adnascent Chinese liverwort, Radula sumatrana . Seven monoterpene—shikimate—conjugated meroterpenoids with a spiro ring system have been isolated from Guignardia mangiferae. Among them, manginoid A (143) represents the first example of spiro meroterpenoid bearing a bridged spirocyclohexanedione moiety. Manginoid E (144) possesses an unexpected 2, 4-dioxatricyclo[3.3.1.03, 7] nonane motif. Compound 143 exhibits inhibitory activity against 11β-hydroxysteroid dehydrogenase type 1 with an IC50 of 0.84 μmol·L-1 . The endophytic fungus Guignardia mangiferae isolated from Ilex cornuta leaves has been shown to produce a family of meroterpenes with toll-like receptor 3 regulating activity. Among the isolates, compound 145 could selectively upregulate the toll-like receptor 3 expression in mouse dendritic cells at 10.0 μmol·L-1. Frutescone A (146), a tasmanone-based meroterpenoid from the aerial parts of Baeckea frutescens L., exhibits moderate cytotoxicities . Chrysogenolide A (147) has been isolated from the solid substrate fermentation cultures of a Huperzia serrata endophytic fungus, Penicillium chrysogenum MT-12 .
Two enantiomeric pairs of meroterpenoids have been isolated from Rhododendron capitatum. Among them, (—)- rhodonoid B (148) and its enantiomer both have been found to show PTP1B inhibitory activities . Five pairs of dimeric meroterpenoid enantiomers have been characterized from Ganoderma cochlear. Among the isolates, (+)-cochlearoid A (149) significantly inhibits Cav3.1 T-type calcium channel (TTCC) with noticeable selectivity . Ganoleucin A (150) has been isolated from the fruiting bodies of Ganoderma leucocontextum. It presents potent noncompetitive inhibitory activity against a-glucosidase from both yeast and rat small intestinal mucosa . A new curcuminoid, curcuterpene G (151), has been isolated from the low polar fraction of methanol extracts from the rhizome of Curcuma longa. Compound 151 exhibits the inhibitory effect to HepG2, A549, and CT-26 tumor cells with the IC50 of 4.82, 8.81, and 5.40 μmol·L-1, respectively . Spiroaspertrione A (152), a novel terpene- polyketide hybrid spiromeroterpenoid, has been isolated from cultures of Aspergillus sp. TJ23. It has been demonstrated to have potent resensitization of oxacillin against methicillin-resistant Staphylococcus aureus by lowering the oxacillin MIC up to 32-fold from 32 to 1 μg·mL-1. Two novel meroterpenoids including yaminterritrem B (153), have been discovered from Aspergillus terreus. Compound 153 exhibits a dose-dependent inhibitory effect on COX-2 expression in LPS-stimulated RAW264.7 macrophages . Dysiherbol A (154), a new tetracyclic meroterpene isolated from a Dysidea sp. marine sponge collected from the South China Sea, possesses an intriguing 6/6/5/6-fused tetracyclic carbon skeleton. The NF-κB inhibitory and cytotoxic activity evaluation disclosed that compound 154 shows potent activity with IC50 of 0.49 and 0.58 μmol·L-1, respectively . Sarglaperoxide A (155), an unusual sesquiterpene—normonoterpene conjugates with a peroxide bridge, has been isolated from the seeds of Sarcandra glabra. It exhibits 64.5% inhibitory effect against Staphylococcus aureus at 25 μg·mL-1 and displayed 53.6% inhibitory effects on NO production in LPS-induced RAW264.7 at 25 μmol·L-1. The results match the traditional applications of S. Glabra . Two novel immunosuppressive unsymmetrical cyclobutane derivatives, including scopariusicide A (156), have been isolated from the aerial parts of Isodon scoparius . Chartarolide A (157), a phenylspirodrimane-based meroterpenoid, has been isolated from a sponge (Niphates recondite) associated fungus Stachybotrys chartarum WGC-25C-6. It exhibits significant cytotoxic activities against a small panel of human tumor cell lines, showing strong inhibitory activities against the human tumor related protein kinases of FGFR3, IGF1R, PDGFRb, and TrKB .Phloroglucinol-terpene adducts
Eleven new polycyclic polyprenylated acylphloroglucinols (PPAPs) have been isolated from the whole plant Hypericum uralum. Among them, uralione A (158) has been found to exhibit significant protective effect against induced injury in PC12 cells . Hyperuralone D (159), a 1, 9-seco-bicyclic PPAP isolated from the aerial parts of Hypericum uralum, exhibits moderate inhibition against AChE with an IC50 of 7.1 μmol·L-1 . Hyperattenin K (160), isolated from Hypericum attenuatum Choisy and identified as a new adamantyl-like PPAP, exhibits inhibitory effect on HIV-1 replication in C8166 cells and moderate cytotoxic effects against the HL-60 and A-549 cell lines . Another two adamantane type PPAPs have been isolated from Hypericum subsessile. Of them, hypersubone B (161) exhibits significant cytotoxicities against four human cancer lines . Garcinia L. is a rich source of PPAPs. (+)-Garcimulin A (162) and its enantiomer, isolated from Garcinia multiflora, exhibits cytotoxic activities against five human cancer cell lines . Garmultin A (163) has been obtained as a pair of enantiomers from the same plant. In an assay for its cytotoxic activities against five human tumor cell lines, the levo isomer exhibits stronger inhibitory activity than the dextro isomer . Hypercohin K (164), the first PPAP possessing a unique spiro-fused cyclopropane ring, has been isolated from Hypericum cohaerens. It has been found to significantly increase the activity of AChE . Callisretone A (165), a rearranged phloroglucinol-monoterpenoid adduct, has been isolated from Callistemon rigidus. It shows inhibitory effects on NO production with an IC50 of 15.3 μmol·L-1 . Viminalin F (166), a hybrid of acylphloroglucinol and α-phellandrene isolated from the fruits of Callistemon viminalis, exhibits moderate cytotoxic activity . Hypersampsonone A (167) has been isolated from the aerial parts of Hypericum sampsonii. It exhibits inhibition against phosphodiesterase-4 (PDE4), a drug target for the treatment of asthma and chronic obstructive pulmonary disease, with an IC50 of 8.08 μmol·L-1 . Garciyunnanimine A (168), a polycyclic polyprenylated acylphloroglucinol imine (PPAP imine), has been isolated from Garcinia yunnanensis .
Callistrilone A (169), the first triketone—phloroglucinol— monoterpene hybrid, has been isolated from the leaves of Callistemon rigidus. It exhibits moderate antibacterial activity against Gram-positive bacteria including multiresistant strains . Drychampone A (170), a sesquiterpenoid-based meroterpenoid, has been isolated from Dryopteris championii. It possesses a novel carbon skeleton constructed by an 11/6/6 ring system coupled with a pyronone moiety . Guapsidial A (171), a sesquiterpene- based psidium meroterpenoid, has been isolated from the leaves of Psidium guajava . Hyperjapone A (172) has been obtained as a racemic mixture from Hypericum japonicum. It exhibits moderate cytotoxic activities against HeLa and HepG2 cell lines . A couple of meroterpenoids have been isolated from the leaves of Rhodomyrtus tomentosa. Among them, tomentodiones A (173) and B are a pair of C-11' epimers of caryophyllene-conjugated phloroglucinols. ; rhodomyrtial A (174) is an unprecedented triketone-sesquiterpene- triketone adduct ; tomentodione E (175) represents the first example of β-calacorene-based meroterpenoid .
Nine new conjugates of sesquiterpenoids and acylphloroglucinols have been isolated from the leaves of Eucalyptus robusta. Among them, eucarobustol A (176) represents the first example of conjugate of aristolane and acylphloroglucinol unit. In turn, eucarobustol C (177) features a new coupling model of guaiane and acylphloroglucinol via the C-4—C-7′ bond. Furthermore, compound 176 shows inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) with IC50 of 1.3 μmol·L-1 . Rhodomentones A (178) and B (179) bearing an unprecedented caryophyllene-conjugated oxa-spiro[5.8] tetradecadiene skeleton, have been isolated from the leaves of Rhodomyrtus tomentosa . A few meroterpenoids with new skeletons have been isolated from the leaves of Myrtus communis. Among them, compound 180 features a new carbon skeleton with an unprecedented octahydrospiro[bicyclo[7.2.0] undecane-2, 2′-chromene] tetracyclic ring system. A variable temperature NMR spectroscopy experiment suggested it existed as a mixture of two conformers (180a and 180b) in solution .
Guajavadimer A (181), a dimeric sesquiterpene-based meroterpenoid, has been isolated from the leaves of Psidium guajava L. It shows moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells . Dimericbiscognienyne A (182), an unusual diisoprenyl- cyclohexene-type meroterpenoid dimer, has been isolated from Biscogniauxia sp. . Three pairs of dimeric meroterpenoid enantiomers have been isolated from the fruiting bodies of Ganoderma applanatum. All of them have been proved to be JAK3 inhibitors. In addition, the enantiomers of applanatumine B (183) are active towards discoidin domain receptor 1 (DDR1) with IC50 of 8.2 μmol·L-1 and 6.9 μmol·L-1 , respectively. Three interesting phloroglucinol-diterpene adducts have been isolated from the roots of a rare Chloranthaceae plant, Chloranthus oldhamii. Among them, chlorabietol C (184) shows inhibitory activity against PTP1B with an IC50 of 4.9 μmol·L-1 .
Four new butyrolactones have been isolated from the fermentation product of the endophytic fungus Aspergillus versicolor. Among them, versicolactone A (185) displays significant antitobacco mosaic virus activity with the inhibition rate of 46.4%, even more potent than the positive control ningnanmycin (30.8%) . Two pairs of racemic spirodienone neolignans have been isolated from the bark of Cinnamomum subavenium. Of all isolates, (—)-subaveniumin B (186) exhibits moderate inhibitory effect against LPS-induced NO production in RAW264.7 mouse macrophages (IC50 4.3 μmol·L-1) . Gastradefurphenol (187), a minor 9, 9′-neolignan, has been isolated from an aqueous extract of the Gastrodia elata rhizomes . The bioassay-guided separation of the dried root of Campylotropis hirtella has led to the isolation of one neuraminidase inhibitor (188) with the IC50 of 16.76 μmol·L-1 .Coumarins
Anisucoumaramide (189) has been isolated from Clausena anisumolens. It shows high selectivity for the MAO-B (human monoamine oxidase) isoenzyme and inhibitory activity in the nanomolar range . The racemic mixture (±)-cnidimonin A (190), isolated from the fruits of Cnidium monnieri, exhibits stronger antiviral activity against HSV-1 (IC50 1.23 μmol·L-1) than its corresponding optically pure enantiomers . Two pairs of oligomeric coumarin enantiomers, including (+)-spirotriscoumarin A (191), have been isolated from Toddalia asiatica. Interestingly, the racemic mixtures exhibits 3- to 6-fold stronger antiviral activity against H3N2 than their corresponding optically pure enantiomers . Andafocoumarin B (192), isolated from the roots of Angelica dahurica cv. Hangbaizhi, exhibits a potent inhibition on NO production in LPS-activated RAW264.7 macrophages, with an IC50 of 13.9 μmol·L-1. Cochlearoid F (193), isolated from the fruiting bodies of Ganoderma cochlear, exhibits potent inhibitory activity on fibronectin overproduction in TGF-β1-induced HKC-8 cells .Flavonoids
From the 95% EtOH extract of the leaves of Garcinia oligantha, oliganthin I (194) has been identified as a new xanthone derivative. It exhibits inhibitory effects on four human tumor cell growth, with IC50 ranging from 3.2 to 6.2 μmol·L-1. Neobraclactone A (195) has been isolated from the leaves of Garcinia bracteata. It shows significant growth inhibition activities against the human leukaemia HL-60 and K562 cell lines with GI50 of 0.50 and 0.40 μmol·L-1, respectively . Four pairs of prenylated flavan enantiomers have been isolated from the stem and root bark of Daphne giraldii. The isolates have a selective cytotoxicity towards hepatic carcinoma cell lines. Among them, (2R)-kazinol B (196) shows a more potent inhibitory effect on Hep3B cells than its racemate . Sophopterocarpan A (197) has been isolated from the roots of Sophora flavescens Ait. It is a potential autophagy activator and exhibits cytotoxic activity in MCF-7 cells . Caesalpinnone A (198), a hybrid of flavan and chalcone, has been isolated from the twigs and leaves of Caesalpinia enneaphylla. It shows the highest cytotoxicities against the HL-60, SMMC-7721, A549, MCF-7, and SW-480 human tumor cell lines with IC50 in the range of 0.54—0.87 μmol·L-1. (+)-Ascomlactone A (199) and (—)-ascomlactone A, a pair of enantiomeric polyketide dimers, have been obtained from a mangrove endophytic fungus Ascomycota sp. SK2YWS-L. Both of them exhibit significant inhibitory effect against α-glucosidase with IC50 of 63.7 and 27.μmol·L-1, respectively . Nine unexpected new flavonol glycoside cyclodimers in the truxinate- or truxillate- form have been isolated as minor components from the extract of Ginkgo biloba leaves. Of them, biginkgoside E (200) significantly inhibits NO production in LPS-activated BV-2 microglial cells, with an IC50 of 2.91 μmol·L-1.Steroids
Gloeophyllin A (201), featuring a rare C-nor-D-homosteroid skeleton, has been isolated from the solid cultures of Gloeophyllum abietinum. It shows strong antiproliferative activity against K562 cells with an IC50 of 4.73 μg·mL-1. A new steroidal ketone (202), with an ergosta-22, 25-diene side chain, has been obtained from the South China Sea marine sponge Xestospongia testudinaria. It exhibits significant inhibitory activity against PTP1B, with an IC50 of 4.27 μmol·L-1 . Two new functionalized ergostane-type steroids, phomopsterones A (203) and B (204), have been isolated from the plant derived Phomopsis sp. TJ507A. Compound 203 is an unprecedented ergosteroid featuring a rearranged bicyclo[3.3.1]nonane motif. Compound 204exhibits anti-inflammatory activity . Ganotheaecolin A (205) has been isolated from the fruiting bodies of Ganoderma theaecolum. It represents a 6/6/7/5-fused carbon skeletal ergosterol. Chantriolide D (206), isolated from the whole plants of Tacca chantrieri, exhibits selective cytotoxicity against A2780 cells with an IC50 of 4.61 μmol·L-1 . Four new C21 steroids with an open-chain sugar moiety have been isolated from the canes of Marsdenia tenacissima. Two of them including compound 207 exhibits a wide spectrum of chemoresistance reversal activity.
Bufospirostenin A (208) and bufogargarizin C (209), two novel steroids with rearranged A/B rings, have been isolated from the toad Bufo bufo gargarizans . 2′S-Arenobufagin-3-O-lactate (210), isolated from the eggs of the toad Bufo bufo gargarizans, exhibits potent cytotoxic effects against human gastric cancer cells BGC-823 and human lung cancer cells A549 with IC50 of 12.19 and 8.86 nmol·L-1, respectively . Aspafilisine (211), featuring a unique rearranged seven- membered B ring formed by the C (7)-C (14) linkage, has been isolated from the roots of Asparagus filicinus . Neocyclocitrinol E (212), an unusual C25 steroid, has been isolated from solid fermentation products of the fungus Chaetomium sp. M453 assosiated with Huperzia serrata (Thunb. Ex Murray) Trev. . Ganoderin A (213) has been isolated from the Ganoderma lucidum spores oil . A novel withanolide, aromaphysalin A (214), possessing an exceptional C (11)-C (15) bond and an unprecedented 4, 9-cyclized aromatic ring (ring A), has been isolated from the stems and leaves of Physalis angulata L. It exhibits inhibitory activity on NO production with an IC50 of 51.64 μmol·L-1 . Two novel physalins, physalin X (215) and aromaphysalin B (216), have been isolated from Physalis angulata L. They both exhibit inhibitory activities on NO production with IC50 of 68.50 and 29.69 μmol·L-1, respectively . Withapubeside B (217), possessing a cage segment and an enolic glucoside moiety, has been isolated from the stems of Physalis pubescens L. . Matsutakone (218), a novel sterol with an unprecedented polycyclic ring system, has been isolated from the fruiting bodies of Tricholoma matsutake. It exhibits inhibitory activity against AChE .
Three novel 7, 8-seco-lycopodane-derived 8, 5-lactones, namely annotinolides A (219), B (220), and C (221), have been isolated from the club mossLycopodium annotinum. They exhibit considerable antiaggregation activities against Aβ1-42 peptide at 50 μmol·L-1 . A novel C16N2 Lycopodium alkaloid, phlefargesiine A (222), has been isolated from the club moss Phlegmariurus fargesii. It exhibits inhibitory effect against AChE with an inhibitory ratio of 36.2% at 40 μmol·L-1 . A little later, a very closely related alkaloid, phleghenrine D (223), together with neophleghenrine A (224) containing a 9-azaprotoadamantane moiety, has been isolated from another club moss Phlegmariurus henryi. Compound 223 shows potent AChE inhibitory activity but no inhibition against BuChE in comparison with tacrine (the positive control) . Squarrosusine A (225) has been isolated from the aerial parts of Phlegmariurus squarrosus. It is the first example of aldol condensation in fawcettimine-type Lycopodium alkaloids . Lycoplanine A (226) has been isolated from the club moss Lycopodium complanatum. It is a potent Cav3.1 T-type calcium channel (TTCC) inhibitor with an IC50 of 6.06 μmol·L-1 .
Sporulaminal A (227), an unusual spiroaminal derived from bergamotane sesquiterpenoid, has been isolated from a marine- derived fungus Paraconiothyrium sporulosum YK-03 . Pericoannosin A (228) and periconiasin F (229) have been isolated from the endophytic fungus Periconia sp. F-31 of the medicinal plant Annona muricata. Both of them shows anti- HIV activity with IC50 of 69.6 and 29.2 μmol·L-1, respectively . (—)-Sinensilactam A (230) has been isolated from the fruiting bodies of Ganoderma sinensis. It has been found to be a Smad3 phosphorylation inhibitor in TGF-β1 induced human renal proximal tubular cells . A couple of matrine-based alkaloids have been discovered from the seeds of Sophora alopecuroides. Sophalines A (231) and B (232) possess unprecedented 6/6/6/4 and 6/5/6/6 ring systems, respectively; while sophaline C (233) is a matrine—acetophenone alkaloid. Compounds 232 and 233 significantly inhibited HBsAg secretion by more than 50.0% at non-cytotoxic concentration of 0.4 mmol·L-1, which is more potent than the positive control lamivudine (3TC) (31.5% at a concentration of 1.0 mmol·L-1) .
Three new Myrioneuron alkaloids have been isolated from Myrioneuron faberi. Among them, myrifamine B (234) shows significant in vitro inhibitory activity towards the hepatitis C virus; myrifamine C (235) is the first example of a symmetric dimer among the Myrioneuron alkaloids . Arthpyrone A (236), a 4-hydroxy-2-pyridone alkaloid, has been isolated from the sponge-derived fungus Arthrinium arundinis ZSDS1-F3. Compound 236 possesses a 2-pyridone core featured with a decalin moiety linked via a carboxide bridge bearing a novel oxabicyclo[3.3.1]-nonane ring system .
Khasuanine A (237), a novel monoterpenoid indole alkaloid, has been isolated from the roots of Melodinus khasianus. It markedly inhibits the proliferation of PC3 cell with an IC50 of 0.45 μmol·L-1 and was able to induce the apoptosis of PC3 cells by activation of caspase 3 and p53, and by inhibition of Bcl-2 . Versicoamide F (238), has been isolated from the fungus Aspergillus tennesseensis. It shows weak antiproliferative activity against the H460 cell line . New monoterpenoid indole alkaloids, kopsinidine C (239) and 11, 12-methylenedioxychanofruticosinic acid (240), have been obtained from the twigs and leaves of Kopsia officinalis . Alstrostine G (241) possessing an unprecedented 6/5/6/6/5/6-ring system has been isolated from Alstonia rostrata . Rauvomine B (242), isolated from the aerial parts of Rauvolfia vomitoria, is a novel C18 normonoterpenoid indole alkaloid with a substituted cyclopropane ring. It exhibits significant anti-inflammatory activity .
Diaporisoindole A (243), a novel isoprenylisoindole alkaloid, has been isolated from the endophytic fungus Diaporthe sp. SYSUHQ3. It exhibits inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B with an IC50 of 4.2 μmol·L-1 . Three pairs of new enantiomeric alkaloids with an unprecedented spiro indolinone- naphthofuran skeleton have been isolated from a marine Streptomyces sp. Among them, (±)-pratensilin A (244) shows moderate cytotoxicities towards a small panel of cell lines .
A rare arcutine-type C20-diterpenoid alkaloid, aconicarmicharcutinium A, has been obtained as hydroxide (245) from the lateral roots of Aconitum carmichaelii . Apetaldine A (246), a C19-diterpenoid alkaloid, has been isolated from Aconitum apetalum . Sinomontadine (247), a C18-diterpenoid alkaloid, has been isolated from Aconitum sinomontanum. It features an unprecedented skeleton containing a seven-membered ring (A-ring) . Pericolactine A (248), obtained from a fungus Periconia sp. (No. 19-4-2-1) isolated from the lichen Parmelia sp., is a new class of diterpenoid alkaloid with an unusual fused 5-5-8-5 tetracyclic ring system . Walujewine A (249) and walujewine C (250), two new isosteroidal alkaloids, have been isolated from the bulbs of Fritillaria walujewii. Compound 249 shows highly selective AChE inhibition and compound 250 was potent dual AChE-BuChE inhibitors . A spinaceamine- bearing pregnane, named scleronine (251), has been isolated from a Chinese soft coral Scleronephthya sp., showing significant inhibitory effects against the migration of tumor cells A549 and B16 .
Flueggether A (252) and virosinine A (253) have been isolated from Flueggea virosa. Both show mild in vitro anti-HIV activity . Chemical investigation of the Nepalese Daphniphyllum himalense has yielded two compounds, himalensines A (254) and B (255). Compound 254 is the first natural C19 Daphniphyllum alkaloid; while 255 bears a 22-nor-1, 13-secodaphnicyclidin skeleton and exhibits marginal inhibitory activities against two kinases, PTP1B and IKK- β . Scholarisine H (256), a new monoterpenoid indole alkaloid possessing a rare cage carbon skeleton, has been isolated from the leaves of Alstonia scholaris . Plantadeprate A (257), a monoterpene zwitterionic guanidium from the seeds of Plantago depressa, exhibits potential antihyperglycemic effect attributed to suppression of hepatic gluconeogenesis with an inhibitory rate of 8.2% at 40 μmol·L-1 . N-4-Demethyl- 21-dehydrokoumine (258), has been isolated from the leaves and vine stems of Gelsemium elegans. It exhibits moderate cytotoxic effects against five human tumor cell lines, with IC50 ranging from 4.6 to 9.3 μmol·L-1 . (+)-Tishaviolamine A (259), featuring an unprecedented 6/5/5/6/5 nitrogen containing heterocyclic skeleton, has been isolated from Viola tianschanica . Conipyridoin E (260) has been identified from the solid culture of the fungus Coniochaeta cephalothecoides. It exhibits strong activity against the growth of both Staphylococcus aureus and MRSA with MIC of 0.97 μmol·L-1 . Gunnilactam A (261), a novel macrocyclic tetralactam, has been isolated from the submerged fermentation broth of Paecilomyces gunnii which is an entomogenous fungus identified as the anamorph of Cordyceps gunnii. Compound 261 exhibits selective cytotoxic activity against human prostate cancer C42B cells with an IC50 of 5.4 μmol·L-1 . From the fermentation broth of the marine-derived Actinoalloteichus cyanogriseus WH1-2216-6, a new 5, 5, 6-polycyclic tetramate macrolactam (PTM) named 16-hydroxymaltophilin (262) has been isolated. It is active against a panel of human cancer cell lines with the IC50 of 4.5-9.7 μmol·L-1. One novel hybrid peptide—polyketide, dahurelmusin A (263), has been isolated from Elymus dahuricus infected by the Epichloë bromicola endophyte. It exhibits significant insecticidal activities against Rhopalosiphum padi and Brevicoryne brassicae with LC50 of 0.092 and 0.251 mmol·L-1, respectively . Nivelactam (264), a new macrolactam derivative, has been isolated from the fermentation broth of Streptomyces niveus. Compound 264 displayed moderate cytotoxic activities against a panel of human tumor cell lines in vitro . Emericellolide A (265), featuring the unprecedented macrolide skeleton composed of an unusual L-glutamate fragment, an isoindolone unit, and a sesquiterpene moiety, has been isolated from a plant endophytic fungus Emericella nidulans HDN12-249 .
Aglaodoratin C (266), a rare C-10 carbonylated aglain- type flavonol-diamide [3+2] adduct, has been isolated from the leaves of Aglaia odorata (Meliaceae). It has been demonstrated to inhibit liver carcinoma HepG2 cell proliferation . Versiquinazoline B (267), a fumiquinazoline-type alkaloid from the gorgonian-derived fungus Aspergillus versicolor LZD-14-1, exhibits inhibitory activities against thioredoxin reductase (TrxR) . Flueggenines E (268) and F (269) have been isolated from the ethanolic extract of Flueggea virosa. Both are Securinega alkaloid hybrids incorporating tryptamine or piperidine residues. Compound 268 shows a moderate anti-HIV activity . Speradine C (270), a highly oxygenated hexacyclic cyclopiazonic acid (CPA) alkaloid, has been isolated from the sponge derived fungus Aspergillus flavus MXH-X104 . Curvularia sp. IFB-Z10, a white croaker-associated fungus, has yielded a skeletally unprecedented indolizine alkaloid named curindolizine (271), which displays an anti-inflammatory action in LPS-induced RAW264.7 macrophages with an IC50 of 5.31 μmol·L-1 .
(+)-Nigegladine A (272) and (-)-nigegladine A, a pair of enantiomers of thymoquinone dimer, have been isolated from the seeds of Nigella glandulifera. They both exhibitsignificant protective effects against hypoxia/reoxygenation-induced H9c2 myocardial cell injury . Two pairs of enantiomeric alkaloid dimers have been isolated from the aerial parts of Macleaya cordata. Among them, (—)-macleayin A (273) exhibits modest cytotoxic activity against the HL-60 cell line with an IC50 of 3.51 μmol·L-1 . Geleganidine B (274), an unusual dimeric monoterpenoid indole alkaloid, has been isolated from the roots of Gelsemium elegans. It shows moderate cytotoxic activity against MCF-7 and PC-12 cells . Exotine A (275), a heterodimer of isopentenyl-substituted indole and coumarin derivative linked through a fused heptacyclic ring system, has been isolated from the roots of Murraya exotica. It shows inhibition of NO production in LPS-induced BV-2 microglial cells . Fistulain A (276), a new type of dimeric chromone alkaloid, has been isolated from the bark of Cassia fistula. It displays anti-TMV activity and weak cytotoxicities . Duclauxamide A1 (277), a new polyketide-derived heptacyclic oligophenalenone dimer with a N-2-hydroxyethyl moiety, has been isolated from Penicillium manginii YIM PH30375 and shows moderate cytotoxic effects against a small panel of cancer cell lines . Four pairs of partially racemized β-carboline alkaloids have been isolated from the extract of Peganum harmala. Among them, pegaharmine D (278) shows significant cytotoxic activities against HL-60, PC-3 and SGC-7901 cell lines . (+)-Pestaloxazine A (279), consisting of 22 carbons and 12 heteroatoms, has been isolated along with its enantiomer from a Pestalotiopsis sp. fungus derived from a soft coral. Compound 279 exhibits potent antiviral activity against EV71 (enterovirus 71) with an IC50 of 14.2 μmol·L-1, stronger than that of the positive control ribavirin (IC50 256.1 μmol·L-1) . (±)-Uncarilin B, a pair of unusual dimeric isoechinulin-type enantiomers with a symmetric four-membered core, have been isolated from Uncaria rhynchophylla. (—)-Uncarilin B (280), at a concentration of 0.25 mmol·L-1, shows activities on MT1 and MT2 (melatonin) receptors with agonistic rates of 11.26% and 52.44%, respectively . Tabercorymines A (281) and B, two new vobasinyl—ibogan-type bisindole alkaloids with an unprecedented skeleton, have been isolated from Tabernaemontana corymbosa. Both of them show potent antiproliferative activities against several human cancer cell lines, including vincristine- resistant KB . A new bisindole alkaloid, hunterizeyline F (282), has been isolated from the twigs and leaves of Hunteria zeylanica . (±)-Peharmaline A (283), existing as a pair of rare β-carboline-vasicinone hybrid alkaloid enantiomers, have been isolated from the seeds of Peganum harmala. They exhibit significant cytotoxic activities against HL-60, PC-3, and SGC-7901 cancer cell lines with IC50 of 9.2, 21.6, and 25.4 μmol·L-1, respectively . Six unusual matrine-type alkaloid dimers have been isolated from the roots of Sophora flavescens. Among them, flavesine A (284) is the first natural matrine-type alkaloid dimer, while flavesine F (285) represents an unprecedented dimerization pattern constructed by matrine and (—)-cytisine .
Gelsekoumidine B (286), obtained as a pair of atropisomeric bisindole alkaloids (286a/286b), has been isolated from the roots of Gelsemium elegans. Compound 286 represents the first example of seco-koumine—gelsedine type alkaloid. It exhibits a moderate inhibitory effect against NO production .
Pseudellone A (287), together with its diastereomer, has been isolated from the marine-derived fungus Pseudallescheria ellipsoidea F42-3 . Four new diketopiperazines have been characterized from the mangrove-derived Penicillium brocae MA-231. Of the isolates, spirobrocazine A (288) possesses a rare spirocyclic 6/5/6/5/6 cyclic system; brocazine G (289) exhibits potent cytotoxicities against both sensitive and cisplatin-resistant human ovarian cancer cells and antimicrobial activity against pathogenic Staphylococcus aureus . One bisthiodiketopiperazine derivative, named adametizine A (290), has been isolated from the marine-sponge derived fungus Penicillium adametzioides AS-53. It exhibits lethality against brine shrimp (Artemia salina) with an LD50 of 4.8 μmol·L-1. Penicisulfuranol A (291), a new epipolythiodioxopiperazine (ETP) alkaloid, has been isolated from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. It shows cytotoxicities against HeLa and HL-60 cell lines with IC50 of 0.1 and 0.5 μmol·L-1, respectively . Streptopertusacin A (292), a unique indolizinium alkaloid existing as a zwitterion, has been isolated from a culture of the seaweed-derived Streptomyces sp. HZP-2216E. It shows moderate activity against the growth of methicillin-resistant Staphylococcus aureus (MRSA) .
Cytochalasan-type secondary metabolites are generally produced by fungi. Armochaetoglobin L (293) has been isolated from the solid culture broth of Chaetomium globosumTW1-1 and shows anti-HIV activity with an EC50 value of 0.48 μmol·L-1. Armochaeglobines A (294) and B (295), another two indolebased cytochalasan alkaloids with new carbon skeletons, have been obtained from the fungus Chaetomium globosum TW1-1 which has been first isolated from the arthropod Armadillidium vulgare . Arthriniumnin A (296) has been isolated and identified from the fungus Arthrinium arundinis ZSDS1-F3 derived from the sponge Phakellia fusca . A novel polycyclic aspochalasin, aspochalazine A (297), has been isolated from the culture broth of Aspergillus sp. found in the gut of a marine isopod Ligia oceanica. It is the first aspochalasin derivative with an azabicyclo . A series of merocytochalasans have been isolated from the culture broth of Aspergillus flavipes. Among them, aspergilasine A (298) possesses a uniquely caged pentacyclo[18.104.22.168, 11.02, 7.05, 10] dodecane skeleton with an unexpected cyclobutane ring ; epicochalasines A (299) and B, possessing a hendecacyclic ring system, can induce G2/M-phase cell cycle arrest significantly ; asperflavipine A (300), possessing two cytochalasan moieties and two epicoccine moieties, is the first cytochalasan heterotetramer; asperflavipine B (301) contains a cytochalasan and two epicoccine moieties. Compound 300 shows moderate cytotoxic effects and induced apoptosis in Jurkat, NB4, and HL60 cells through the activation of caspase-3 and degradation of poly (ADP-ribose) polymerase (PARP) .Polyketides
Penicilfuranone A (302), a novel furancarboxylic acid, has been isolated from the cultures of the fungus Penicillium sp. sh18 endophytic to the stems ofIsodon eriocalyx var. laxiflora . Six new 16-membered macrolides with a rare branched octose unit have been isolated from Streptomyces sp. HK-2006-1. Among the isolates, aldgamycin O (303) shows antibacterial activity against Staphylococcus aureus 209P with an MIC of 16 μg·mL-1.Miscellaneous
A new spiroketal, chlorotheolide B (304), has been isolated from the solid substrate fermentation of the plant endophytic fungus Pestalotiopsis theae (N635). It shows an antiproliferative effect against the human tumor HeLa cell line and induces an autophagic process in the cells . (+)-Denobilone A (305), together with its enantiomer, has been isolated from Dendrobium nobile. Both of them show moderate inhibitory effects against HeLa, MCF-7, and A549 cells . Diasteltoxin A (306), asteltoxin-bearing dimers, has been isolated from a mutated strain of a sponge-derived fungus Emericella variecolor XSA-07-2. It exerted certain inhibitory effects against two tumor cell lines (H1299 and MCF-7) and exhibits inhibition against thioredoxin reductase (TrxR) . Grisemycin (307), the first sulfur angucyclinone with an unusual ether- bridged system, has been isolated from a marine-derived Streptomyces griseus strain M268. It exhibits modestly selective activity against HL-60 . Selesconol (308), an inducer for the differentiation of rat bone marrow mesenchymal stem cells into neural cells, has been obtained from the culture of Daldinia eschscholzii IFB-TL01 . Dihydrotrichodimer ether A (309), a rare bisorbicillinoid with a γ-pyrone moiety, has been isolated from the fungus Clonostachys rosea YRS-06. It displays potent inhibition activity against E. Coli with an MIC value of 25 μg·mL-1 . Citrifuran A (310), metabolized by an Aspergillus sp., shows moderate inhibitory activity against LPS-induced NO production in RAW 264.7 macrophages with an IC50 of 18.3 μmol·L-1 . Three novel aromatic azoxy compounds including azoxymycin A (311) have been isolated and identified from Streptomyces chattanoogensis L10 . Forsythenethoside A (312) has been isolated from the fruits of Forsythia suspensa. It shows strong neuroprotective activity against serum-deprivation-induced PC12 cell damage . Rifamorpholine B (313) has been isolated from the culture of a locust associated rare actinobacteria, Amycolatopsis sp. HCa4, showing potent activity against MRSA with an MIC of 4.0 μmol·L-1 . A new griseofulvin derivative, 4′-demethoxy-4′-N-isopentylisogriseofulvin (314), has been isolated from Penicillium griseofulvum CPCC 400528. It exhibits anti-HIV activity with an IC50 of 33.2 μmol·L-1 . Chrysanthemorimic acid A (315) has been isolated and characterized from the flowers of Chrysanthemum morifolium. It displays significant effect against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells at 10 μmol·L-1. The phytochemical investigations on the rhizomes of Atractylodes lancea have led to the isolation of compound 316. It shows weak inhibitory effects on α-glucosidases and protein tyrosine phosphates 1B (PTP1B) at a concentration of 10 μmol·L-1 . Lecanicillone A (317), an unusual dimeric spiciferone with acyclobutane ring via a [2 + 2] cycloaddition, has been isolated from an entomopathogenic fungus Lecanicillium sp. PR-M-3. Compound 317 shows moderate cytotoxicity against the HL-60 cell line . Tadehaginoside D (318), obtained from Tadehagi triquetrum, significantly increases the basal and insulin-elicited glucose uptake . The biosynthesis gene cluster (fls) for atypical angucycline fluostatins has been identified from the marine derived Micromonospora rosaria SCSIO N160. Heterologous expression of the intact fls-gene cluster in Streptomyces coelicolor YF11 in the presence of 3% sea salts yielded difluostatin A (319) which exhibits antibacterial activities . By genome wide deletions of epigenetic regulators in entomopathogenic fungus Metarhizium robertsii, unexpected activations of orphan secondary metabolite genes have been found upon the disruption of a histone acetyltransferase (HAT) gene Hat1. This led to the characterization of 8 isocoumarin derivatives including meromuside A (320) .Discussion and Perspective
Natural products (NPs) are rich source for novel compounds that are of great value, not only for organic chemistry but also for drug discovery. In the years of 2015, 2016, and 2017, with the development of separation and analytical techniques, a bunch of more complex natural products with/without better bioactivities have been identified by Chinese researchers. Because of the limitation of length, we deeply feel sorry that this review could not cover all achievements in NPs chemistry made by Chinese scholars. Nevertheless, the selected findings could represent the advanced NPs chemistry researches in the past three years, and would greatly enrich our knowledge about NPs and help accelerate the process for drug discovery. The newly discovered chemical structures provide new ideas for drug researchers. At the same time, some of NPs can be just served as lead compounds for drug discovery. For example, fortunilide A (27), showing antimarial activity at low nanomolar level, could be a promising drug candidate like arteminsinin; stelleralide F (49) shows significant anti-HIV activity about 34 times better than AZT in an in vitro assay; phainanoid F (121), the immunosuppressive triterpene with new carbon skeleton, exhibits exceptionally potent immunosuppressive activities in vitro against the proliferation of T and B lymphocytes, which is about 7 and 221 times as active as cyclosporin A.
The biosyntheses studies and genetic regulations are of great help for understanding the biosynthetic pathway of NPs. As a branch of NPs research, such studies provide a future view for NPs scientific direction: with the help of biologists, chemists can manufacture any interesting compounds or try to get novel compounds by gene manipulation.
However, there are still some critical limitations concerning NPs research in China. First, how can we elucidate the interactions between the compounds existing in one plant/ organism? It's difficult while it's imperative to identify real active compounds from crude extracts. Second, how can we discover the mass-limited NPs with novel skeletons and potent bioactivities from unexploited nature sources (e.g., endangered plants native to China )? Meanwhile, how can we rapidly achieve the miniaturization (microgram scale) of the structure elucidation using new analytical technologies (e.g., advanced NMR probes [278, 279])? Third, how can we develop more reliable and more sensitive screening methods? China is a large nation with tradition of prescribing herbal medicines. Thousands of years of practice accumulates enormous clinical data that are treasures for human beings. By cooperating with scientists all over the world, Chinese scholars will for sure make greater achievements in NPs research in the years to come.Acknowledgements
We thank Prof. YE Yang (Shanghai Institute of Materia Medica, Chinese Academy of Sciences) for suggestions and discussions in preparation of this review. We are grateful to our lab members for assistance in literature search and preparation of this review.
Zhang JF, Huang S, Shan LH, et al. New iridoid glucoside from Pterocephalus hookeri[J]. Chinese J Org Chem, 2015, 35(11): 2441-2444. DOI:10.6023/cjoc201506001
Geng CA, Chen XL, Huang XY, et al. Sweriyunnanlactone A, one unusual secoiridoid trimer from Swertia yunnanensis[J]. Tetrahedron Lett, 2015, 56(17): 2163-2166. DOI:10.1016/j.tetlet.2015.03.057
Li D, Jiang YY, Jin ZM, et al. Isolation and absolute configurations of diastereomers of 8α-hydroxy-T-muurolol and (1α, 6β, 7β)- cadinane-4-en-8α, 10α-diol from Chimonanthus salicifolius[J]. Phytochemistry, 2016, 122: 294-300. DOI:10.1016/j.phytochem.2016.01.005
Hu ZX, Shi YM, Wang WG, et al. Structural characterization of kadcoccinin A: a sesquiterpenoid with a tricyclo[4.4.0.03, 10]decane scaffold from Kadsura coccinea[J]. Org Lett, 2016, 18(9): 2284-2287. DOI:10.1021/acs.orglett.6b00919
Shi YS, Liu YB, Ma SG, et al. Bioactive sesquiterpenes and lignans from the fruits of Xanthium sibiricum[J]. J Nat Prod, 2015, 78(7): 1526-1535. DOI:10.1021/np500951s
Fang LL, Lin WW, Qiu GG, et al. Substolides A-G, germacrane sesquiterpenoids from Salvia substolonifera[J]. Phytochemistry, 2015, 120: 28-35. DOI:10.1016/j.phytochem.2015.09.013
Liu QX, Yang YX, Zhang JP, et al. Isolation, structure elucidation, and absolute configuration of highly oxygenated germacranolides from Carpesium cernuum[J]. J Nat Prod, 2016, 79(10): 2479-2486. DOI:10.1021/acs.jnatprod.6b00315
Hu CL, Xiong J, Li JY, et al. Rare sesquiterpenoids from the shed trunk barks of the critically endangered plant Abies beshanzuensis and their bioactivities[J]. Eur J Org Chem, 2016, 2016(10): 1832-1835. DOI:10.1002/ejoc.v2016.10
Xi FM, Ma SG, Liu YB, et al. Artaboterpenoids A and B, bisabolene-derived sesquiterpenoids from Artabotrys hexapetalus[J]. Org Lett, 2016, 18(14): 3374-3377. DOI:10.1021/acs.orglett.6b01519
Wang JF, He WJ, Kong FD, et al. Ochracenes A-I, humulane-derived sesquiterpenoids from the Antarctic fungus Aspergillus ochraceopetaliformis[J]. J Nat Prod, 2017, 80(6): 1725-1733. DOI:10.1021/acs.jnatprod.6b00810
Li JL, Fu Y, Zhang HY, et al. Two new humulanolides from the roots of Cynanchum wilfordii[J]. Tetrahedron Lett, 2015, 56(46): 6503-6505. DOI:10.1016/j.tetlet.2015.10.016
Jiao WH, Xu TT, Zhao F, et al. Dysifragilones A-C, unusual sesquiterpene aminoquinones and inhibitors of NO production from the South China Sea sponge Dysidea fragilis[J]. Eur J Org Chem, 2015, 2015(5): 960-966. DOI:10.1002/ejoc.v2015.5
Liu H, Li XM, Liu Y, et al. Chermesins A-D: meroterpenoids with a drimane-type spirosesquiterpene skeleton from the marine algal-derived endophytic fungus Penicillium chermesinum EN-480[J]. J Nat Prod, 2016, 79(4): 806-811. DOI:10.1021/acs.jnatprod.5b00893
Yang NN, Kong FD, Ma QY, et al. Chemical constituents from the cultures of fungus Xylaria polymorpha[J]. Chin J Org Chem, 2017, 37(4): 1033-1039. DOI:10.6023/cjoc201612039
Huang SZ, Ma QY, Kong FD, et al. Daphnauranins A and B, two new antifeedants isolated from Daphne aurantiaca roots[J]. Fitoterapia, 2017, 122: 11-15. DOI:10.1016/j.fitote.2017.08.001
Wu XD, Zhong WW, Ding LF, et al. Sesquiterpenoids from the twigs and leaves of Fokienia hodginsii[J]. J Asian Nat Prod Res, 2017, 19(7): 666-672. DOI:10.1080/10286020.2016.1247350
Zhang CG, Jin MR, Chou GX, et al. Plebeins A-F, sesquiterpenoids and diterpenoids from Salvia plebeian[J]. Phytochem Lett, 2017, 19: 254-258. DOI:10.1016/j.phytol.2017.02.001
Ma SG, Li M, Lin MB, et al. Illisimonin A, a caged sesquiterpenoid with a tricyclo[5.2.1.01, 6]decane skeleton from the fruits of Illicium simonsii[J]. Org Lett, 2017, 19(22): 6160-6163. DOI:10.1021/acs.orglett.7b03050
Dong SJ, Li BC, Dai WF, et al. Sesqui- and diterpenoids from the radix of Curcuma aromatica[J]. J Nat Prod, 2017, 80(12): 3093-3102. DOI:10.1021/acs.jnatprod.6b01100
Feng T, Li XM, He J, et al. Nicotabin A, a sesquiterpenoid derivative from Nicotiana tabacum[J]. Org Lett, 2017, 19(19): 5201-5203. DOI:10.1021/acs.orglett.7b02559
Dong L, Cheng LZ, Yan YM, et al. Commiphoranes A-D, carbon skeletal terpenoids from Resina commiphora[J]. Org Lett, 2017, 19(1): 286-289. DOI:10.1021/acs.orglett.6b03661
Li QM, Luo JG, Zhang YM, et al. Involucratustones A-C: unprecedented sesquiterpene dimers containing multiple contiguous quaternary carbons from Stahlianthus involucratus[J]. Chem Eur J, 2015, 21(38): 13206-13209. DOI:10.1002/chem.v21.38
Yan H, Ba MY, Li XH, et al. Lindenane sesquiterpenoid dimers from Chloranthus japonicus inhibit HIV-1 and HCV replication[J]. Fitoterapia, 2016, 115: 64-68. DOI:10.1016/j.fitote.2016.09.023
Zhou B, Wu Y, Dalal S, et al. Nanomolar antimalarial agents against chloroquine-resistant Plasmodium falciparum from medicinal plants and their structure-activity relationships[J]. J Nat Prod, 2017, 80(1): 96-107. DOI:10.1021/acs.jnatprod.6b00744
Zhou B, Liu QF, Dalal S, et al. Fortunoids A-C, three sesquiterpenoid dimers with different carbon skeletons from Chloranthus fortunei[J]. Org Lett, 2017, 19(3): 734-737. DOI:10.1021/acs.orglett.7b00066
Wang P, Luo J, Zhang YM, et al. Sesquiterpene dimers esterified with diverse small organic acids from the seeds of Sarcandra glabra[J]. Tetrahedron, 2015, 71(33): 5362-5370. DOI:10.1016/j.tet.2015.05.112
Xu XK, Ye J, Chen LP, et al. Four new isomeric sesquiterpene lactone dimers from Carpesium faberi[J]. Tetrahedron Lett, 2015, 56(46): 6381-6384. DOI:10.1016/j.tetlet.2015.09.127
Ma YL, Wang MJ, Yi ZC, et al. A new bis-sesquiterpenoid from Artemisia selengensis[J]. Chin Tradit Herb Drugs, 2017, 48(14): 2817-2819.
Wu JW, Tang CP, Chen L, et al. Dicarabrones A and B, a pair of new epimers dimerized from sesquiterpene lactones via a[J]. Org Lett, 2015, 17(7): 1656-1659. DOI:10.1021/acs.orglett.5b00371
Xie GB, Xie Y, Hu YZ, et al. Cytotoxic sesquiterpenoids from Ligularia pleurocaulis[J]. Phytochemistry, 2016, 125: 99-105. DOI:10.1016/j.phytochem.2016.02.010
Qi QY, Ren JW, Sun LW, et al. Stucturally diverse sesquiterpenes produced by a Chinese Tibet fungus Stereum hirsutum and their cytotoxic and immunosuppressant activities[J]. Org Lett, 2015, 17(12): 3098-3101. DOI:10.1021/acs.orglett.5b01356
Zhang YL, Zhou XW, Wang XB, et al. Xylopiana A, a dimeric guaiane with a case-shaped core from Xylopia vielana: structural elucidation and biomimetic conversion[J]. Org Lett, 2017, 19(11): 3013-3016. DOI:10.1021/acs.orglett.7b01276
Xue GM, Han C, Chen C, et al. Artemisians A-D, diseco- guaianolide involved heterodimeric[J]. Org Lett, 2017, 19(19): 5410-5413. DOI:10.1021/acs.orglett.7b02681
Zhang CG, Wang L, Lu Y, et al. Diterpenoids from the whole plant of Lagochilus platyacanthus[J]. Planta Med, 2015, 81(15): 1345-1352. DOI:10.1055/s-00000058
Xiong L, Zhou QM, Zou YK, et al. Leonuketal, a spiroketal diterpenoid from Leonurus japonicus[J]. Org Lett, 2015, 17(24): 6238-6241. DOI:10.1021/acs.orglett.5b03227
Zhou JC, Zhang JZ, Cheng AX, et al. Highly rigid labdane-type diterpenoids from a Chinese liverwort and light-driven structure diversification[J]. Org Lett, 2015, 17(14): 3560-3563. DOI:10.1021/acs.orglett.5b01664
Xiong J, Hong ZL, Xu P, et al. ent-Abietane diterpenoids with anti-neuroinflammatory activity from the rare Chloranthaceae plant Chloranthus oldhamii[J]. Org Biomol Chem, 2016, 14(20): 4678-4689. DOI:10.1039/C6OB00731G
Zhang CG, Chou GX, Mao XD, et al. Nepetaefolins A-J, cytotoxic chinane and abietane diterpenoids from Caryopteris nepetaefolia[J]. J Nat Prod, 2017, 80(6): 1742-1749. DOI:10.1021/acs.jnatprod.6b00972
Zhu J, Wang R, Lou L, et al. Jatrophane diterpenoids as modulators of P-glycoprotein-dependent multidrug resistance (MDR): advances of structure-activity relationships and discovery of promising MDR reversal agents[J]. J Med Chem, 2016, 59(13): 6353-6369. DOI:10.1021/acs.jmedchem.6b00605
Wang WQ, Xuan LJ. ent-6, 7-Secokaurane diterpenoids from Rabdosia serra and their cytotoxic activities[J]. Phytochemistry, 2016, 122: 119-125. DOI:10.1016/j.phytochem.2015.11.014
Niu CS, Li Y, Liu YB, et al. Pierisketolide A and pierisketones B and C, three diterpenes with an unusual carbon skeleton from the roots of Pieris formosa[J]. Org Lett, 2017, 19(4): 906-909. DOI:10.1021/acs.orglett.7b00048
Jiang HY, Wang WG, Tang JW, et al. Structurally diverse diterpenoids from Isodon scoparius and their bioactivity[J]. J Nat Prod, 2017, 80(7): 2026-2036. DOI:10.1021/acs.jnatprod.7b00163
Wang WG, Tang JW, Shi YM, et al. Laxiflorol A, the first example of 7, 8: 15, 16-di-seco-15-nor-21-homo-ent-kauranoid from Isodon eriocalyx var. laxiflora[J]. RSC Adv, 2015, 5(8): 6132-6135. DOI:10.1039/C4RA12704H
Yan M, Lu Y, Chen CH, et al. Stelleralides D-J and anti-HIV daphnane diterpenes from Stellera chamaejasme[J]. J Nat Prod, 2015, 78(11): 2712-2718. DOI:10.1021/acs.jnatprod.5b00660
Xu J, Peng MQ, Sun XC, et al. Bioactive diterpenoids from Trigonostemon chinensis: structures, NO inhibitory activities, and interactions with iNOS[J]. Bioorg Med Chem Lett, 2016, 26(19): 4785-4789. DOI:10.1016/j.bmcl.2016.08.026
Zhou JF, Sun N, Zhang HQ, et al. Rhodomollacetals A-C, PTP1B inhibitory diterpenoids with a 2, 3: 5, 6-di-seco- grayanane skeleton from the leaves of Rhododendron molle[J]. Org Lett, 2017, 19(19): 5352-5355. DOI:10.1021/acs.orglett.7b02633
Zhou JF, Zhan GQ, Zhang HQ, et al. Rhodomollanol A, a highly oxygenated diterpenoid with a 5/7/5/5 tetracyclic carbon skeleton from the leaves of Rhododendron molle[J]. Org Lett, 2017, 19(14): 3935-3938. DOI:10.1021/acs.orglett.7b01863
Zhou L, Tuo YL, Hao Y, et al. Cinnamomols A and B, immunostimulative diterpenoids with a new carbon skeleton from the leaves of Cinnamomum cassia[J]. Org Lett, 2017, 19(11): 3029-3032. DOI:10.1021/acs.orglett.7b01323
Yu HB, Gu BB, Wang SP, et al. New diterpenoids from the marine sponge Dactylospongia elegans[J]. Tetrahedron, 2017, 73(47): 6657-6661. DOI:10.1016/j.tet.2017.10.023
Wang L, Yang J, Kong LM, et al. Natural and semisynthetic tigliane diterpenoids with new carbon skeletons from Euphorbia dracunculoides as a Wnt signaling pathway inhibitor[J]. Org Lett, 2017, 19(14): 3911-3914. DOI:10.1021/acs.orglett.7b01813
Chen YY, Yang KX, Yang XW, et al. New cytotoxic tigliane diterpenoids from Croton caudatus[J]. Planta Med, 2016, 82(8): 729-733. DOI:10.1055/s-00000058
Jiang ZY, Yu YJ, Huang CG, et al. Icetexane diterpenoids from Perovskia atriplicifolia[J]. Planta Med, 2015, 81(3): 241-246. DOI:10.1055/s-00000058
Shen CP, Luo JG, Yang MH, et al. Cafestol-type diterpenoids from the twigs of Tricalysia fruticosa with potential anti-inflammatory activity[J]. J Nat Prod, 2015, 78(6): 1322-1329. DOI:10.1021/acs.jnatprod.5b00165
Liu SN, Huang D, Morris-Natschke SL, et al. Euphomilones A and B, ent-rosane diterpenoids with 7/5/6 and 5/7/6 skeletons from Euphorbia milii[J]. Org Lett, 2016, 18(23): 6132-6135. DOI:10.1021/acs.orglett.6b03142
Tang Y, Xue YB, Du G, et al. Structural revisions of a class of natural products: scaffolds of aglycon analogues of fusicoccins and cotylenins isolated from fungi[J]. Angew Chem Int Edit, 2016, 128(12): 4137-4141. DOI:10.1002/ange.201600313
Ye F, Zhu ZD, Chen JS, et al. Xishacorenes A-C, diterpenes with bicyclo[3.3.1] nonane nucleus from the Xisha soft coral Sinularia polydactyla[J]. Org Lett, 2017, 19(16): 4183-4186. DOI:10.1021/acs.orglett.7b01716
Dong RJ, Yuan JZ, Wu SL, et al. Anti-inflammation furanoditerpenoids from Caesalpinia minax Hance[J]. Phytochemistry, 2015, 117: 325-331. DOI:10.1016/j.phytochem.2015.06.025
Ma GX, Wu HF, Chen DL, et al. Antimalarial and antiproliferative cassane diterpenes of Caesalpinia sappan[J]. J Nat Prod, 2015, 78(10): 2364-2371. DOI:10.1021/acs.jnatprod.5b00317
Ren J, Wang YG, Wang AG, et al. Cembranoids from the gum resin of Boswellia carterii as potential antiulcerative colitis agents[J]. J Nat Prod, 2015, 78(10): 2322-2331. DOI:10.1021/acs.jnatprod.5b00104
Wu TZ, Wang Q, Jiang C, et al. neo-Clerodane diterpenoids from Scutellaria barbata with activity against Epstein-Barr virus lytic replication[J]. J Nat Prod, 2015, 78(3): 500-509. DOI:10.1021/np500988m
Yuan QQ, Tang S, Song WB, et al. Crassins A-H, diterpenoids from the roots of Croton crassifolius[J]. J Nat Prod, 2017, 80(2): 254-260. DOI:10.1021/acs.jnatprod.6b00425
Fang FH, Huang WJ, Zhou SY, et al. Aphapolins A and B: two nemoralisin diterpenoids isolated from Aphanamixis polystachya (Wall.) R. Parker[J]. Eur J Org Chem, 2017, 2017(30): 4428-4433.
Bian XQ, Bai J, Hu XL, et al. Penioxalicin, a novel 3-nor-2, 3-seco-labdane type diterpene from the fungus Penicillium oxalicum TW01-1[J]. Tetrahedron Lett, 2015, 56(35): 5013-5016. DOI:10.1016/j.tetlet.2015.07.014
Luo P, Xia WJ, Morris-Natschke SL, et al. Vitepyrroloids A-D, 2-cyanopyrrole- containing labdane diterpenoid alkaloids from the leaves of Vitex trifolia[J]. J Nat Prod, 2017, 80(5): 1679-1683. DOI:10.1021/acs.jnatprod.6b01195
Xie CF, Sun LM, Liao K, et al. Bioactive ent-pimarane and ent-abietane diterpenoids from the whole plants of Chloranthus henryi[J]. J Nat Prod, 2015, 78(11): 2800-2807. DOI:10.1021/acs.jnatprod.5b00781
Liang XR, Miao FP, Song YP, et al. Citrinovirin with a new norditerpene skeleton from the marine algicolous fungus Trichoderma citrinoviride[J]. Bioorg Med Chem Lett, 2016, 26(20): 5029-5031. DOI:10.1016/j.bmcl.2016.08.093
Xu JB, Fan YY, Gan LS, et al. Cephalotanins A-D, four norditerpenoids represent three highly rigid carbon skeletons from Cephalotaxus sinensis[J]. Chem Eur J, 2016, 22(41): 14648-14654. DOI:10.1002/chem.201603373
Fan YY, Xu JB, Liu HC, et al. Cephanolides A-J, cephalotane- type diterpenoids from Cephalotaxus sinensis[J]. J Nat Prod, 2017, 80(12): 3159-3166. DOI:10.1021/acs.jnatprod.7b00412
Feng ZL, Zhang LL, Zheng YD, et al. Norditerpenoids and dinorditerpenoids from the seeds of Podocarpus nagi as cytotoxic agents and autophagy inducers[J]. J Nat Prod, 2017, 80(7): 2110-2117. DOI:10.1021/acs.jnatprod.7b00347
Gobu FR, Chen JJ, Zeng J, et al. Isolation, structure elucidition, and immunosuppressive activity of diterpenoids from Ligularia fischeri[J]. J Nat Prod, 2017, 80(8): 2263-2268. DOI:10.1021/acs.jnatprod.7b00198
Ni G, Zhang H, Fan YY, et al. Mannolides A-C with an intact diterpenoid skeleton providing insights on the biosynthesis of antitumor Cephalotaxus troponoids[J]. Org Lett, 2016, 18(8): 1880-1883. DOI:10.1021/acs.orglett.6b00653
Song JL, Yuan Y, Tan HB, et al. Euryachins A and B, a new type of diterpenoids from Eurya chinensis with potent NO production inhibitory activity[J]. RSC Adv, 2016, 6(89): 85958-85961. DOI:10.1039/C6RA11994H
Wan LS, Nian Y, Ye CJ, et al. Three minor diterpenoids with three carbon skeletons from Euphorbia peplus[J]. Org Lett, 2016, 18(9): 2166-2169. DOI:10.1021/acs.orglett.6b00787
Chen WT, Yao LG, Li XW, et al. Sarcophytrols A-C, new capnosane diterpenoids from the South China Sea soft coral Sarcophyton trocheliophorum[J]. Tetrahedron Lett, 2015, 56(11): 1348-1352. DOI:10.1016/j.tetlet.2015.01.157
Fei DQ, Dong LL, Qi FM, et al. Euphorikanin A, a diterpenoid lactone with a fused 5/6/7/3 ring system from Euphorbia kansui[J]. Org Lett, 2016, 18(12): 2844-2847. DOI:10.1021/acs.orglett.6b01093
Li Y, Liu YB, Zhang JJ, et al. Antinociceptive grayanoids from the roots of Rhododendron molle[J]. J Nat Prod, 2015, 78(12): 2887-2895. DOI:10.1021/acs.jnatprod.5b00456
Bai R, Zhang CC, Yin X, et al. Striatoids A-F, cyathane diterpenoids with neurotrophic activity from cultures of the fungus Cyathus striatus[J]. J Nat Prod, 2015, 78(4): 783-788. DOI:10.1021/np501030r
Fang X, Di YT, Zhang Y, et al. Unprecedented quassinoids with promising biological activity from Harrisonia perforata[J]. Angew Chem Int Edit, 2015, 54(19): 5592-5595. DOI:10.1002/anie.201412126
Lou HY, Jin L, Huang T, et al. Vulgarisins B-D, three novel diterpenoids with a rare skeleton isolated from Prunella vulgaris Linn[J]. Tetrahedron Lett, 2017, 58(5): 401-404. DOI:10.1016/j.tetlet.2016.12.029
Gao C, Han L, Zheng D, et al. Dimeric abietane diterpenoids and sesquiterpenoid lactones from Teucrium viscidum[J]. J Nat Prod, 2015, 78(4): 630-638. DOI:10.1021/np500746n
Zhang H, Liu J, Gan LS, et al. Antimalarial diterpenoid dimers of a new carbon skeleton from Aphanamixis grandifolia[J]. Org Biomol Chem, 2016, 14(3): 957-962. DOI:10.1039/C5OB02296G
Huang XH, Tao LX, Ke CQ, et al. Taxodikaloids A and B, two dimeric abietane- type diterpenoids from Taxodium ascendens possessing an oxazoline ring linkage[J]. Org Lett, 2017, 19(3): 556-559. DOI:10.1021/acs.orglett.6b03597
Wei YL, Wang C, Cheng ZB, et al. Heterodimeric diterpenoids isolated from Euphorbia ebracteolata roots and their inhibitory effects on α-glucosidase[J]. J Nat Prod, 2017, 80(12): 3219-3224.
Liu HC, Xiang ZB, Wang Q, et al. Monomeric and dimeric ent-kauranoid-type diterpenoids from Rabdosia japonica and their cytotoxicity and anti-HBV activities[J]. Fitoterapia, 2017, 118: 94-100. DOI:10.1016/j.fitote.2017.03.006
Zhou SZ, Tang CP, Ke CQ, et al. Three new dimeric diterpenes from Rhododendron molle[J]. Chin Chem Lett, 2017, 28(6): 1205-1209. DOI:10.1016/j.cclet.2017.02.020
Chen CC, Tzeng TT, Chen CC, et al. Erinacine S, a rare sesterterpene from the mycelia of Hericium erinaceus[J]. J Nat Prod, 2016, 79(2): 438-441. DOI:10.1021/acs.jnatprod.5b00474
Liu ZM, Chen Y, Chen SH, et al. Aspterpenacids A and B, two sesterterpenoids from a mangrove endophytic fungus Aspergillus terreus H010[J]. Org Lett, 2016, 18(6): 1406-1409. DOI:10.1021/acs.orglett.6b00336
Dong M, Quan LQ, Dai WF, et al. Anti-inflammatory and anti-HIV compounds from Swertia bimaculata[J]. Planta Med, 2017, 83(17): 1368-1373. DOI:10.1055/s-0043-114736
Shi ZZ, Miao FP, Fang ST, et al. Sesteralterin and tricycloalterfurenes A-D: terpenes with rarely occurring frameworks from the marine-alga-epiphytic fungus Alternaria alternata k21-1[J]. J Nat Prod, 2017, 80(9): 2524-2529. DOI:10.1021/acs.jnatprod.7b00478
Jiao WH, Hong LL, Sun JB, et al. (±)-Hippolide J - a pair of unusual antifungal enantiomeric sesterterpenoids from the marine sponge Hippospongia lachne[J]. Eur J Org Chem, 2017, 2017(24): 3421-3426. DOI:10.1002/ejoc.v2017.24
Han JX, Li LY, Zhong JL, et al. Officimalonic acids A-H, lanostane triterpenes from the fruiting bodies of Fomes officinalis[J]. Phytochemistry, 2016, 130: 193-200. DOI:10.1016/j.phytochem.2016.05.004
Xiao SJ, Shi DB, Yuan ZL, et al. Two new rearranged lanostane triterpenoids from Tsuga longibracteata[J]. Chin J Org Chem, 2016, 36(7): 1686-1689. DOI:10.6023/cjoc201601035
Hu ZX, Shi YM, Wang WG, et al. Kadcoccinones A-F, new biogenetically related lanostane-type triterpenoids with diverse skeletons from Kadsura coccinea[J]. Org Lett, 2015, 17(18): 4616-4619. DOI:10.1021/acs.orglett.5b02360
Li ZY, Qi FM, Zhi DJ, et al. A novel spirocyclic triterpenoid and a new taraxerane triterpenoid from Teucrium viscidum[J]. Org Chem Front, 2017, 4(1): 42-46.
Ma K, Li L, Bao L, et al. Six new 3, 4-seco-27-norlanostane triterpenes from the medicinal mushroom Ganoderma boninense and their antiplasmodial activity and agonistic activity to LXRβ[J]. Tetrahedron, 2015, 71(12): 1808-1814. DOI:10.1016/j.tet.2015.02.002
Xu J, Kang J, Sun XC, et al. Di- and Triterpenoids from the leaves of Casearia balansae and neurite outgrowth promoting effects of PC12 cells[J]. J Nat Prod, 2016, 79(1): 170-179. DOI:10.1021/acs.jnatprod.5b00815
Wang WH, Nian Y, He YJ, et al. New cycloartane triterpenes from the aerial parts of Cimicifuga heracleifolia[J]. Tetrahedron, 2015, 71(42): 8018-8025. DOI:10.1016/j.tet.2015.08.057
Zhang CL, Liu YF, Wang Y, et al. Polycycloiridals A-D, four iridal-type triterpenoids with an α-terpineol moiety from Iris tectorum[J]. Org Lett, 2015, 17(22): 5686-5689. DOI:10.1021/acs.orglett.5b02982
Shi YM, Cai SL, Li XN, et al. LC-UV-guided isolation and structure determination of lancolide E: a nortriterpenoid with a tetracyclo[5.4.0.02, 4.03, 7] undecane-bridged system from a "talented" Schisandra plant[J]. Org Lett, 2016, 18(1): 100-103. DOI:10.1021/acs.orglett.5b03334
Zhou M, Liu Y, Song J, et al. Schincalide A, a schinortriterpenoid with a tricyclo[5.2.1.01, 6]decane-bridged system from the stems and leaves of Schisandra incarnate[J]. Org Lett, 2016, 18(18): 4558-4561. DOI:10.1021/acs.orglett.6b02197
Song J, Liu Y, Zhou M, et al. Spiroschincarins A-E: five spirocyclic nortriterpenoids from the fruit of Schisandra incarnata[J]. Org Lett, 2017, 19(5): 1196-1199. DOI:10.1021/acs.orglett.7b00250
Wang C, Huo XK, Luan ZL, et al. Alismanin A, a triterpenoid with a C34 skeleton from Alisma orientale as a natural agonist of human pregnane X receptor[J]. Org Lett, 2017, 19(20): 5645-5648. DOI:10.1021/acs.orglett.7b02738
Xu J, Xiao D, Lin QH, et al. Cytotoxic tirucallane and apotirucallane triterpenoids from the stems of Picrasma quassioides[J]. J Nat Prod, 2016, 79(8): 1899-1910. DOI:10.1021/acs.jnatprod.5b01137
Zhao QQ, Song QY, Jiang K, et al. Spirochensilides A and B, two new rearranged triterpenoids from Abies chensiensis[J]. Org Lett, 2015, 17(11): 2760-2763. DOI:10.1021/acs.orglett.5b01166
Fan YY, Zhang H, Zhou Y, et al. Phainanoids A-F, a new class of potent immunosuppressive triterpenoids with an unprecedented carbon skeleton from Phyllanthus hainanensis[J]. J Am Chem Soc, 2015, 137(1): 138-141. DOI:10.1021/ja511813g
Fan YY, Gan LS, Liu HC, et al. Phainanolide A, highly modified and oxygenated triterpenoid from Phyllanthus hainanensis[J]. Org Lett, 2017, 19(17): 4580-4583. DOI:10.1021/acs.orglett.7b02181
Yu JH, Liu QF, Sheng L, et al. Cipacinoids A-D, four limonoids with spirocyclic skeletons from Cipadessa cinerascens[J]. Org Lett, 2016, 18(3): 444-447. DOI:10.1021/acs.orglett.5b03487
Yu JH, Wang GC, Han YS, et al. Limonoids with anti-HIV activity from Cipadessa cinerascens[J]. J Nat Prod, 2015, 78(6): 1243-1252. DOI:10.1021/acs.jnatprod.5b00025
Yan Y, Zhang JX, Huang T, et al. Bioactive limonoid constituents of Munronia henryi[J]. J Nat Prod, 2015, 78(4): 811-821. DOI:10.1021/np501057f
An FL, Sun DM, Li RJ, et al. Walrobsins A and B, two anti-inflammatory limonoids from root barks of Walsura robusta[J]. Org Lett, 2017, 19(17): 4568-4571. DOI:10.1021/acs.orglett.7b02173
Zhang Y, An FL, Huang SS, et al. Diverse triterpenoids from the fruits of Walsura robusta and their reversal of multidrug resistance phenotype in human breast cancer cells[J]. Phytochemistry, 2017, 136: 108-118. DOI:10.1016/j.phytochem.2017.01.008
An FL, Luo J, Li RJ, et al. Spirotrichilins A and B: two rearranged spirocyclic limonoids from Trichilia connaroides[J]. Org Lett, 2016, 18(8): 1924-1927. DOI:10.1021/acs.orglett.6b00738
An FL, Luo J, Wang XB, et al. Trichiconlides A and B: two novel limonoids from the fruits of Trichilia connaroides[J]. Org Biomol Chem, 2016, 14(4): 1231-1235. DOI:10.1039/C5OB02300A
Wang GC, Fan YY, Shyaula SL, et al. Triconoids A-D, four limonoids possess two rearranged carbon skeletons from Trichilia connaroides[J]. Org Lett, 2017, 19(8): 2182-2185. DOI:10.1021/acs.orglett.7b00873
Yi L, Zhang HJ, Tian XM, et al. Four new limonoids from the seeds of Chukrasia tabularis A. Juss[J]. Phytochem Lett, 2017, 19: 12-17. DOI:10.1016/j.phytol.2016.11.004
Wu YB, Wang YZ, Ni ZY, et al. Xylomexicanins I and J: limonoids with unusual B/C rings from Xylocarpus granatum[J]. J Nat Prod, 2017, 80(9): 2547-2550. DOI:10.1021/acs.jnatprod.7b00305
Liu CP, Wang GC, Gan LS, et al. Ciliatonoids A and B, two limonoids from Toona ciliata[J]. Org Lett, 2016, 18(12): 2894-2897. DOI:10.1021/acs.orglett.6b01213
Lv C, Yan XH, Tu Q, et al. Isolation and asymmetric total synthesis of perforanoid A[J]. Angew Chem Int Edit, 2016, 55(26): 7539-7543. DOI:10.1002/anie.201602783
Li WS, Wu J, Li J, et al. Krishnadimer A, an axially chiral non- biaryl natural product: discovery and biomimetic synthesis[J]. Org Lett, 2017, 19(1): 182-185. DOI:10.1021/acs.orglett.6b03479
Liao HB, Huang GH, Yu MH, et al. Five pairs of meroterpenoid enantiomers from Rhododendron capitatum[J]. J Org Chem, 2017, 82(3): 1632-1637. DOI:10.1021/acs.joc.6b02800
Wang X, Li L, Zhu RX, et al. Bibenzyl-based meroterpenoid enantiomers from the Chinese liverwort Radula sumatrana[J]. J Nat Prod, 2017, 80(12): 3143-3150. DOI:10.1021/acs.jnatprod.7b00394
Chen KL, Zhang XW, Sun WG, et al. Manginoids A-G: seven monoterpene- shikimate-conjugated meroterpenoids with a spiro ring system from Guignardia mangiferae[J]. Org Lett, 2017, 19(21): 5956-5959. DOI:10.1021/acs.orglett.7b02955
Han WB, Dou H, Yuan WH, et al. Meroterpenes with toll-like receptor 3 regulating activity from the endophytic fungus Guignardia mangiferae[J]. Planta Med, 2015, 81(2): 145-151.
Hou JQ, Guo C, Zhao JJ, et al. Frutescone A-G, tasmanone- based meroterpenoids from the aerial parts of Baeckea frutescens[J]. J Org Chem, 2017, 82(3): 1448-1457. DOI:10.1021/acs.joc.6b02643
Qi BW, Liu X, Mo T, et al. 3, 5-Dimethylorsellinic acid derived meroterpenoids from Penicillium chrysogenum MT-12, an endophytic fungus isolated from Huperzia serrata[J]. J Nat Prod, 2017, 80(10): 2699-2707. DOI:10.1021/acs.jnatprod.7b00438
Liao HB, Lei C, Gao LX, et al. Two enantiomeric pairs of meroterpenoids from Rhododendron capitatum[J]. Org Lett, 2015, 17(20): 5040-5043. DOI:10.1021/acs.orglett.5b02515
Zhou FJ, Nian Y, Yan YM, et al. Two new classes of T-type Calcium channel inhibitors with new chemical scaffolds from Ganoderma cochlear[J]. Org Lett, 2015, 17(12): 3082-3085. DOI:10.1021/acs.orglett.5b01353
Wang K, Bao L, Ma K, et al. A novel class of α-glucosidase and HMG-CoA reductase inhibitors from Ganoderma leucocontextum and the anti-diabetic properties of ganomycin I in KK-Ay mice[J]. Eur J Med Chem, 2017, 127: 1035-1046. DOI:10.1016/j.ejmech.2016.11.015
Li R, Jia K, Fu Q, et al. LC-MS guided discovery, structural elucidation of a new curcuminoids, and its cytotoxicity[J]. Chin Tradit Herb Drugs, 2016, 47(14): 2418-2423.
He Y, Hu ZX, Sun WG, et al. Spiroaspertrione A, a bridged spirocyclic meroterpenoid, as a potent potentiator of oxacillin against methicillin-resistant Staphylococcus aureus from Aspergillus sp. TJ23[J]. J Org Chem, 2017, 82(6): 3125-3131. DOI:10.1021/acs.joc.7b00056
Liaw CC, Yang YL, Lin CK, et al. New meroterpenoids from Aspergillus terreus with inhibition of cyclooxygenase-2 expression[J]. Org Lett, 2015, 17(10): 2330-2333. DOI:10.1021/acs.orglett.5b00739
Jiao WH, Shi GH, Xu TT, et al. Dysiherbols A-C and dysideanone E, cytotoxic and NF-κB inhibitory tetracyclic meroterpenes from a Dysidea sp. marine sponge[J]. J Nat Prod, 2016, 79(2): 406-411. DOI:10.1021/acs.jnatprod.5b01079
Wang P, Li RJ, Liu RH, et al. Sarglaperoxides A and B, sesquiterpene-normonoterpene conjugates with a peroxide bridge from the seeds of Sarcandra glabra[J]. Org Lett, 2016, 18(4): 832-835. DOI:10.1021/acs.orglett.6b00112
Zhou M, Li XR, Tang JW, et al. Scopariusicides, novel unsymmetrical cyclobutanes: structural elucidation and concise synthesis by a combination of intermolecular[J]. Org Lett, 2015, 17(24): 6062-6065. DOI:10.1021/acs.orglett.5b03079
Liu D, Li Y, Li XD, et al. Chartarolides A-C, novel meroterpenoids with antitumor activities[J]. Tetrahedron Lett, 2017, 58(19): 1826-1829. DOI:10.1016/j.tetlet.2017.03.079
Zhou ZB, Li ZR, Wang XB, et al. Polycyclic polyprenylated derivatives from Hypericum uralum: neuroprotective effects and antidepressant-like activity of uralodin A[J]. J Nat Prod, 2016, 79(5): 1231-1240. DOI:10.1021/acs.jnatprod.5b00667
Zhang JJ, Yang XW, Liu X, et al. 1, 9-Seco-bicyclic polyprenylated acylphloroglucinols from Hypericum uralum[J]. J Nat Prod, 2015, 78(12): 3075-3079. DOI:10.1021/acs.jnatprod.5b00830
Li DY, Zhu HC, Qi CX, et al. Two new adamantyl-like polyprenylated acylphloroglucinols from Hypericum attenuatum choisy[J]. Tetrahedron Lett, 2015, 56(15): 1953-1955. DOI:10.1016/j.tetlet.2015.02.056
Liao Y, Liu X, Yang J, et al. Hypersubones A and B, new polycyclic acylphloroglucinols with intriguing adamantane type cores from Hypericum subsessile[J]. Org Lett, 2015, 17(5): 1172-1175. DOI:10.1021/acs.orglett.5b00100
Fan YM, Yi P, Li Y, et al. Two unusual polycyclic polyprenylated acylphloroglucinols, including a pair of enantiomers from Garcinia multiflora[J]. Org Lett, 2015, 17(9): 2066-2069. DOI:10.1021/acs.orglett.5b00588
Tian DS, Yi P, Xia L, et al. Garmultins A-G, biogenetically related polycyclic acylphloroglucinols from Garcinia multiflora[J]. Org Lett, 2016, 18(22): 5904-5907. DOI:10.1021/acs.orglett.6b03004
Yang XW, Yang J, Liao Y, et al. Hypercohin K, a polycyclic polyprenylated acylphloroglucinol with an unusual spiro-fused cyclopropane ring from Hypericum cohaerens[J]. Tetrahedron Lett, 2015, 56(41): 5537-5540. DOI:10.1016/j.tetlet.2015.08.033
Cao JQ, Tian HY, Li MM, et al. Rearranged phloroglucinol- monoterpenoid adducts from Callistemon rigidus[J]. J Nat Prod, 2018, 81(1): 57-62. DOI:10.1021/acs.jnatprod.7b00606
Wu L, Zhang YL, Wang XB, et al. Viminalins A-O: diverse[J]. Tetrahedron, 2017, 73(8): 1105-1113. DOI:10.1016/j.tet.2016.12.076
Zhang JS, Zou YH, Guo YQ, et al. Polycyclic polyprenylated acylphloroglucinols: natural phosphodiesterase-4 inhibitors from Hypericum sampsonii[J]. RSC Adv, 2016, 6(58): 53469-53476. DOI:10.1039/C6RA08805H
Zheng D, Zhang H, Zheng CW, et al. Garciyunnanimines A-C, novel cytotoxic polycyclic polyprenylated acylphloroglucinol imines from Garcinia yunnanensis[J]. Org Chem Front, 2017, 4(11): 2102-2108. DOI:10.1039/C7QO00485K
Cao JQ, Huang XJ, Li YT, et al. Callistrilones A and B, triketone-phloroglucinol- monoterpene hybrids with a new skeleton from Callistemon rigidus[J]. Org Lett, 2016, 18(1): 120-123. DOI:10.1021/acs.orglett.5b03360
Chen NH, Zhang YB, Huang XJ, et al. Drychampones A-C: three meroterpenoids from Dryopteris championii[J]. J Org Chem, 2016, 81(19): 9443-9448. DOI:10.1021/acs.joc.6b01720
Jian YQ, Huang XJ, Zhang DM, et al. Guapsidial A and guadials B and C: three new meroterpenoids with unusual skeletons from the leaves of Psidium guajava[J]. Chem Eur J, 2015, 21(25): 9022-9027. DOI:10.1002/chem.v21.25
Yang XW, Li YP, Su J, et al. Hyperjapones A-E, terpenoid polymethylated acylphloroglucinols from Hypericum japonicum[J]. Org Lett, 2016, 18(8): 1876-1879. DOI:10.1021/acs.orglett.6b00650
Liu HX, Chen K, Tang GH, et al. Isolation and biomimetic total synthesis of tomentodiones A-B, terpenoid-conjugated phloroglucinols from the leaves of Rhodomyrtus tomentosa[J]. RSC Adv, 2016, 6(53): 48231-48236. DOI:10.1039/C6RA08776K
Zhang YL, Chen C, Wang XB, et al. Rhodomyrtials A and B, two meroterpenoids with a triketone-sesquiterpene-triketone skeleton from Rhodomyrtus tomentosa: structural elucidation and biomimetic synthesis[J]. Org Lett, 2016, 18(16): 4068-4071. DOI:10.1021/acs.orglett.6b01944
Zhang YL, Zhou XW, Wu L, et al. Isolation, structure elucidation, and absolute configuration of syncarpic acid-conjugated terpenoids from Rhodomyrtus tomentosa[J]. J Nat Prod, 2017, 80(4): 989-998. DOI:10.1021/acs.jnatprod.6b01005
Yu Y, Gan LS, Yang SP, et al. Eucarobustols A-I, conjugates of sesquiterpenoids and acylphloroglucinols from Eucalyptus robusta[J]. J Nat Prod, 2016, 79(5): 1365-1372. DOI:10.1021/acs.jnatprod.6b00090
Liu HX, Chen K, Yuan Y, et al. Rhodomentones A and B, novel meroterpenoids with unique NMR characteristics from Rhodomyrtus tomentosa[J]. Org Biomol Chem, 2016, 14(30): 7354-7360. DOI:10.1039/C6OB01215A
Liu C, Ang S, Huang XJ, et al. Meroterpenoids with new skeletons from Myrtus communis and structure revision of myrtucommulone K[J]. Org Lett, 2016, 18(16): 4004-4007. DOI:10.1021/acs.orglett.6b01817
Li CJ, Ma J, Sun H, et al. Guajavadimer A, a dimeric caryophyllene-derived meroterpenoid with a new carbon skeleton from the leaves of Psidium guajava[J]. Org Lett, 2016, 18(2): 168-171. DOI:10.1021/acs.orglett.5b03117
Zhao H, Chen GD, Zou J, et al. Dimericbiscognienyne A: a meroterpenoid dimer from Biscogniauxia sp. with new skeleton and its activity[J]. Org Lett, 2017, 19(1): 38-41. DOI:10.1021/acs.orglett.6b03264
Luo Q, Wang Z, Luo J, et al. (±)-Applanatumines B-D: novel dimeric meroterpenoids from Ganoderma applanatum as inhibitors of JAK3[J]. RSC Adv, 2017, 7(60): 38037-38043. DOI:10.1039/C7RA04862A
Xiong J, Hong ZL, Gao LX, et al. Chlorabietols A-C, phloroglucinol-diterpene adducts from the Chloranthaceae plant Chloranthus oldhamii[J]. J Org Chem, 2015, 80(21): 11080-11085. DOI:10.1021/acs.joc.5b01658
Zhou M, Du G, Yang HY, et al. Antiviral butyrolactones from the endophytic fungus Aspergillus versicolor[J]. Planta Med, 2015, 81(3): 235-240.
Lai YJ, Liu TT, Sa RJ, et al. Neolignans with a rare 2-oxaspiro[4.5]deca-6, 9-dien- 8-one motif from the stem bark of Cinnamomum subavenium[J]. J Nat Prod, 2015, 78(7): 1740-1744. DOI:10.1021/np5010533
Zhou X, Guo QL, Zhu CG, et al. Gastradefurphenol, a minor 9, 9'-neolignan with a new carbon skeleton substituted by two p-hydroxybenzyls from an aqueous extract of "tian ma"[J]. Chin Chem Lett, 2017, 28(6): 1185-1189. DOI:10.1016/j.cclet.2017.03.028
Du X, Xuan BX, Shen ZW. Chemical constituents with neuraminidase inhibitory activities from Campylotropis Hirtella[J]. Acta Chim Sin, 2015(7): 741-748.
Wang YS, Li BT, Liu SX, et al. Anisucoumaramide, a bioactive coumarin from Clausena anisumolens[J]. J Nat Prod, 2017, 80(4): 798-804. DOI:10.1021/acs.jnatprod.6b00391
Su FY, Zhao Z, Ma SG, et al. Cnidimonins A-C, three types of hybrid dimer from Cnidium monnieri: structural elucidation and semisynthesis[J]. Org Lett, 2017, 19(18): 4920-4923. DOI:10.1021/acs.orglett.7b02290
Tang ZH, Liu YB, Ma SG, et al. Antiviral spirotriscoumarins A and B: two pairs of oligomeric coumarin enantiomers with a spirodienone-sesquiterpene skeleton from Toddalia asiatica[J]. Org Lett, 2016, 18(19): 5146-5149. DOI:10.1021/acs.orglett.6b02572
Wei W, Wu XW, Deng GG, et al. Anti-inflammatory coumarins with short- and long-chain hydrophobic groups from roots of Angelica dahurica cv. Hangbaizhi[J]. Phytochemistry, 2016, 123: 58-68. DOI:10.1016/j.phytochem.2016.01.006
Wang XL, Zhou FJ, Dou M, et al. Cochlearoids F-K: phenolic meroterpenoids from the fungus Ganoderma cochlear and their renoprotective activity[J]. Bioorg Med Chem Lett, 2016, 26(22): 5507-5512. DOI:10.1016/j.bmcl.2016.10.011
Tang YX, Fu WW, Wu R, et al. Bioassay-guided isolation of prenylated xanthone derivatives from the leaves of Garcinia oligantha[J]. J Nat Prod, 2016, 79(7): 1752-1761. DOI:10.1021/acs.jnatprod.6b00137
Niu SL, Li DH, Wang YT, et al. Neobraclactones A-C, three unprecedented chaise longue-shaped xanthones from Garcinia bracteata[J]. Org Biomol Chem, 2017, 15(22): 4901-4906. DOI:10.1039/C7OB01007A
Sun Q, Yao GD, Song XY, et al. Autophagy antagonizes apoptosis induced by flavan enantiomers from Daphne giraldii in hepatic carcinoma cells in vitro[J]. Eur J Med Chem, 2017, 133: 1-10. DOI:10.1016/j.ejmech.2017.03.072
Zhu H, Yang YN, Xu K, et al. Sophopterocarpan A, a novel pterocarpine derivative with a benzotetrahydrofuran-fused bicyclo[3.3.1] nonane from Sophora flavescens[J]. Org Biomol Chem, 2017, 15(26): 5480-5483. DOI:10.1039/C7OB01261F
Zhang LJ, Bi DW, Hu JM, et al. Four hybrid flavan-chalcones, caesalpinnone A possessing a 10, 11-dioxatricyclic[5.3.3.01, 6] tridecane-bridged system and caesalpinflavans A-C from Caesalpinia enneaphylla[J]. Org Lett, 2017, 19(16): 4315-4318. DOI:10.1021/acs.orglett.7b01955
Liu ZM, Chen SH, Qiu P, et al. (+)- and (-)-Ascomlactone A: a pair of novel dimeric polyketides from a mangrove endophytic fungus Ascomycota sp. SK2YWS-L[J]. Org Biomol Chem, 2017, 15(48): 10276-10280. DOI:10.1039/C7OB02707A
Ma GL, Xiong J, Yang GX, et al. Biginkgosides A-I, unexpected minor dimeric flavonol diglycosidic truxinate and truxillate esters from Ginkgo biloba leaves and their antineuroinflammatory and neuroprotective activities[J]. J Nat Prod, 2016, 79(5): 1354-1364. DOI:10.1021/acs.jnatprod.6b00061
Han JJ, Bao L, Tao QQ, et al. Gloeophyllins A-J, cytotoxic ergosteroids with various skeletons from a Chinese Tibet fungus Gloeophyllum abietinum[J]. Org Lett, 2015, 17(10): 2538-2541. DOI:10.1021/acs.orglett.5b01080
He WF, Xue DQ, Yao LG, et al. A new bioactive steroidal ketone from the South China Sea sponge Xestospongia testudinaria[J]. J Asian Nat Prod Res, 2016, 18(2): 195-199. DOI:10.1080/10286020.2015.1056521
Hu ZX, Wu Y, Xie SS, et al. Phomopsterones A and B, two functionalized ergostane-type steroids from the endophytic fungus Phomopsis sp. TJ507A[J]. Org Lett, 2017, 19(1): 258-261. DOI:10.1021/acs.orglett.6b03557
Luo Q, Yang ZL, Yan YM, et al. Ganotheaecolin A, a neurotrophic conjugated ergosterol with a naphtho[1, 8-ef] azulene scaffold from Ganoderma theaecolum[J]. Org Lett, 2017, 19(3): 718-721. DOI:10.1021/acs.orglett.7b00012
Ni G, Yang HZ, Fu NJ, et al. Cytotoxic taccalonolides and withanolides from Tacca chantrieri[J]. Planta Med, 2015, 81(3): 247-256. DOI:10.1055/s-00000058
Yao S, To KK, Ma L, et al. Polyoxypregnane steroids with an open-chain sugar moiety from Marsdenia tenacissima and their chemoresistance reversal activity[J]. Phytochemistry, 2016, 126: 47-58. DOI:10.1016/j.phytochem.2016.03.006
Tian HY, Ruan LJ, Yu T, et al. Bufospirostenin A and bufogargarizin C, steroids with rearranged skeletons from the toad Bufo bufo gargarizans[J]. J Nat Prod, 2017, 80(4): 1182-1186. DOI:10.1021/acs.jnatprod.6b01018
Zhou SW, Zheng QF, Huang XY, et al. Isolation and identification of L/D-lactate- conjugated bufadienolides from toad eggs revealing lactate racemization in amphibians[J]. Org Biomol Chem, 2017, 15(26): 5609-5615. DOI:10.1039/C7OB01055A
Wang JP, Cai L, Chen FY, et al. A new steroid with unique rearranged seven- membered B ring isolated from roots of Asparagus filicinus[J]. Tetrahedron Lett, 2017, 58: 3590-3593. DOI:10.1016/j.tetlet.2017.07.072
Yu FX, Li Z, Chen Y, et al. Four new steroids from the endophytic fungus Chaetomium sp. M453 derived of Chinese herbal medicine Huperzia serrata[J]. Fitoterapia, 2017, 117: 41-46. DOI:10.1016/j.fitote.2016.12.012
Ge FH, Duan MH, Li J, et al. Ganoderin A, a novel 9, 11-secosterol from Ganoderma lucidum spores oil[J]. J Asian Nat Prod Res, 2017, 19(12): 1252-1257. DOI:10.1080/10286020.2017.1313834
Sun CP, Kutateladze AG, Zhao F, et al. A novel withanolide with an unprecedented carbon skeleton from Physalis angulata[J]. Org Biomol Chem, 2017, 15(5): 1110-1114. DOI:10.1039/C6OB02656G
Sun CP, Oppong MB, Zhao F, et al. Unprecedented 22, 26-seco physalins from Physalis angulata and their anti-inflammatory potential[J]. Org Biomol Chem, 2017, 15(41): 8700-8704. DOI:10.1039/C7OB02205K
Xia GY, Yao T, Zhang BY, et al. Withapubesides A-D: natural inducible nitric oxide synthase (iNOS) inhibitors from Physalis pubescens[J]. Org Biomol Chem, 2017, 15(47): 10016-10023. DOI:10.1039/C7OB02551C
Zhao ZZ, Chen HP, Wu B, et al. Matsutakone and matsutoic acid, two (nor) steroids with unusual skeletons from the edible mushroom Tricholoma matsutake[J]. J Org Chem, 2017, 82(15): 7974-7979. DOI:10.1021/acs.joc.7b01230
Tang Y, Xiong J, Zhang JJ, et al. Annotinolides A-C, three lycopodane-derived 8, 5-lactones with polycyclic skeletons from Lycopodium annotinum[J]. Org Lett, 2016, 18(17): 4376-4379. DOI:10.1021/acs.orglett.6b02132
Meng WJ, Xiong J, Wang WX, et al. Phlefargesiine A, a C16N2 lycopodium alkaloid with an unprecedented[6/7/6/6]- tetracyclic skeleton from Phlegmariurus fargesii[J]. Tetrahedron Lett, 2016, 57(29): 3218-3221. DOI:10.1016/j.tetlet.2016.06.050
Dong LB, Wu XD, Shi X, et al. Phleghenrines A-D and neophleghenrine A, bioactive and structurally rigid Lycopodium alkaloids from Phlegmariurus henryi[J]. Org Lett, 2016, 18(18): 4498-4501. DOI:10.1021/acs.orglett.6b02065
Li P, Huang W, Zhuo JX, et al. Seven new Lycopodium alkaloids from the aerial parts of Phlegmariurus squarrosus[J]. Tetrahedron, 2015, 71(33): 5308-5314. DOI:10.1016/j.tet.2015.06.012
Zhang ZJ, Nian Y, Zhu QF, et al. Lycoplanine A, a C16N lycopodium alkaloid with a 6/9/5 tricyclic skeleton from Lycopodium complanatum[J]. Org Lett, 2017, 19(17): 4668-4671. DOI:10.1021/acs.orglett.7b02293
Zhang LH, Feng BM, Chen G, et al. Sporulaminals A and B: a pair of unusual epimeric spiroaminal derivatives from a marine- derived fungus Paraconiothyrium sporulosum YK-03[J]. RSC Adv, 2016, 6(48): 42361-42366. DOI:10.1039/C6RA01401A
Zhang DW, Tao XY, Chen RD, et al. Pericoannosin A, a polyketide synthase-nonribosomal peptide synthetase hybrid metabolite with new carbon skeleton from the endophytic fungus Periconia sp[J]. Org Lett, 2015, 17(17): 4304-4307. DOI:10.1021/acs.orglett.5b02123
Luo Q, Tian L, Di L, et al. (±)-Sinensilactam A, a pair of rare hybrid metabolites with Smad3 phosphorylation inhibition from Ganoderma sinensis[J]. Org Lett, 2015, 17(6): 1565-1568. DOI:10.1021/acs.orglett.5b00448
Zhang Y, Zhang X, Chen N, et al. Four matrine-based alkaloids with antiviral activities against HBV from the seeds of Sophora alopecuroides[J]. Org Lett, 2017, 19(2): 424-427. DOI:10.1021/acs.orglett.6b03685
Cao MM, Zhang Y, Huang SD, et al. Alkaloids with different carbon units from Myrioneuron faberi[J]. J Nat Prod, 2015, 78(11): 2609-2616. DOI:10.1021/acs.jnatprod.5b00543
Wang JF, Wei XY, Qin XC, et al. Arthpyrones A-C, pyridone alkaloids from a sponge-derived fungus Arthrinium arundinis ZSDS1-F3[J]. Org Lett, 2015, 17(3): 656-659. DOI:10.1021/ol503646c
Zhou J, Feng JH, Fang L. A novel monoterpenoid indole alkaloid with anticancer activity from Melodinus khasianus[J]. Bioorg Med Chem Lett, 2017, 27(4): 893-896. DOI:10.1016/j.bmcl.2017.01.005
Liu L, Wang L, Bao L, et al. Versicoamides F-H, prenylated indole alkaloids from Aspergillus tennesseensis[J]. Org Lett, 2017, 19(4): 942-945. DOI:10.1021/acs.orglett.7b00145
Zeng T, Wu XY, Yang SX, et al. Monoterpenoid indole alkaloids from Kopsia officinalis and the immunosuppressive activity of rhazinilam[J]. J Nat Prod, 2017, 80(4): 864-871. DOI:10.1021/acs.jnatprod.6b00697
Zhong XH, Bao MF, Zeng CX, et al. Polycyclic monoterpenoid indole alkaloids from Alstonia rostrata and their reticulate derivation[J]. Phytochem Lett, 2017, 20: 77-83. DOI:10.1016/j.phytol.2017.04.008
Zeng J, Zhang DB, Zhou PP, et al. Rauvomines A and B, two monoterpenoid indole alkaloids from Rauvolfia vomitoria[J]. Org Lett, 2017, 19(15): 3998-4001. DOI:10.1021/acs.orglett.7b01723
Cui H, Lin Y, Luo MC, et al. Diaporisoindoles A-C: three isoprenylisoindole alkaloid derivatives from the mangrove endophytic fungus Diaporthe sp. SYSU- HQ3[J]. Org Lett, 2017, 19(20): 5621-5624. DOI:10.1021/acs.orglett.7b02748
Zhang SM, Yang Q, Guo L, et al. Isolation, structure elucidation and racemization of (+)- and (-)-pratensilins A-C: unprecedented spiro indolinone-naphthofuran alkaloids from a marine Streptomyces sp[J]. Chem Commun, 2017, 53(72): 10066-10069. DOI:10.1039/C7CC04983H
Meng XH, Jiang ZB, Guo QL, et al. A minor arcutine-type C20-diterpenoid alkaloid iminium constituent of "fu zi"[J]. Chin Chem Lett, 2017, 28(3): 588-592. DOI:10.1016/j.cclet.2016.11.010
Zhang JF, Chen L, Huang S, et al. Diterpenoid alkaloids from two Aconitum species with antifeedant activity against Spodoptera exigua[J]. J Nat Prod, 2017, 80(12): 3136-3142. DOI:10.1021/acs.jnatprod.7b00380
Zhang Q, Tan JJ, Chen XQ, et al. Two novel C18-diterpenoid alkaloids, sinomontadine with an unprecedented seven-membered ring A and chloride-containing sinomontanine N from Aconitum sinomontanum[J]. Tetrahedron Lett, 2017, 58(18): 1717-1720. DOI:10.1016/j.tetlet.2017.03.013
Wu YH, Chen GD, He RR, et al. Pericolactines A-C, a new class of diterpenoid alkaloids with unusual tetracyclic skeleton[J]. Sci Rep, 2015, 5(1): 17082. DOI:10.1038/srep17082
Liu YM, Feng YD, Lu X, et al. Isosteroidal alkaloids as potent dual-binding site inhibitors of both acetylcholinesterase and butyrylcholinesterase from the bulbs of Fritillaria walujewii[J]. Eur J Med Chem, 2017, 137: 280-291. DOI:10.1016/j.ejmech.2017.06.007
Cheng W, Liu Z, Yu Y, et al. An unusual spinaceamine-bearing pregnane from a soft coral Scleronephthya sp. inhibits the migration of tumor cells[J]. Bioorg Med Chem Lett, 2017, 27(12): 2736-2741. DOI:10.1016/j.bmcl.2017.04.058
Zhang H, Zhu KK, Han YS, et al. Flueggether A and virosinine A, anti-HIV alkaloids from Flueggea virosa[J]. Org Lett, 2015, 17(24): 6274-6277. DOI:10.1021/acs.orglett.5b03320
Zhang H, Shyaula SL, Li JY, et al. Himalensines A and B, alkaloids from Daphniphyllum himalense[J]. Org Lett, 2016, 18(5): 1202-1205. DOI:10.1021/acs.orglett.6b00362
Yang XW, Luo XD, Lunga PK, et al. Scholarisines H-O, novel indole alkaloid derivatives from long-term stored Alstonia scholaris[J]. Tetrahedron, 2015, 71(22): 3694-3698. DOI:10.1016/j.tet.2014.09.052
Zheng XM, Meng FW, Geng F, et al. Plantadeprate A, a tricyclic monoterpene zwitterionic guanidium, and related derivatives from the seeds of Plantago depressa[J]. J Nat Prod, 2015, 78(11): 2822-2826. DOI:10.1021/acs.jnatprod.5b00368
Xu YK, Yang L, Liao SG, et al. Koumine, humantenine, and yohimbane alkaloids from Gelsemium elegans[J]. J Nat Prod, 2015, 78(7): 1511-1517. DOI:10.1021/np5009619
Chen QB, Aisa HA. Alkaloid constituents from Viola tianschanica[J]. Phytochemistry, 2017, 144: 233-242. DOI:10.1016/j.phytochem.2017.09.011
Han JJ, Liu CC, Li L, et al. Decalin-containing tetramic acids and 4-hydroxy-2- pyridones with antimicrobial and cytotoxic activity from the fungus Coniochaeta cephalothecoides collected in Tibetan Plateau (Medog)[J]. J Org Chem, 2017, 82(21): 11474-11486. DOI:10.1021/acs.joc.7b02010
Zheng YB, Zhang JY, Wei LF, et al. Gunnilactams A-C, macrocyclic tetralactams from the mycelial culture of the entomogenous fungus Paecilomyces gunnii[J]. J Nat Prod, 2017, 80(6): 1935-1938. DOI:10.1021/acs.jnatprod.7b00060
Mei XG, Wang LP, Wang DY, et al. Polycyclic tetramate macrolactams from the marine-derived Actinoalloteichus cyanogriseus WH1-2216-6[J]. Chin J Org Chem, 2017, 37(9): 2352-2360. DOI:10.6023/cjoc201703048
Song QY, Yu HT, Zhang XX, et al. Dahurelmusin A, a hybrid peptide-polyketide from Elymus dahuricus infected by the Epichloë bromicola endophyte[J]. Org Lett, 2017, 19(1): 298-300. DOI:10.1021/acs.orglett.6b03568
Li LY, Cai YP, Jiang Y, et al. A unique macrolactam derivative via a[4+6]- cycloaddition from Streptomyces niveus[J]. Bioorg Med Chem Lett, 2016, 26(6): 1599-1604. DOI:10.1016/j.bmcl.2016.02.002
Zhou HB, Sun XH, Li N, et al. Isoindolone-containing meroperpenoids from the endophytic fungus Emericella nidulans HDN12-249[J]. Org Lett, 2016, 18(18): 4670-4673. DOI:10.1021/acs.orglett.6b02297
An FL, Wang JS, Wang H, et al. Cytotoxic flavonol-diamide[3+2] adducts from the leaves of Aglaia odorata[J]. Tetrahedron, 2015, 71(16): 2450-2457. DOI:10.1016/j.tet.2015.02.028
Cheng ZB, Lou LL, Liu D, et al. Versiquinazolines A-K, fumiquinazoline-type alkaloids from the gorgonian-derived fungus Aspergillus versicolor LZD-14-1[J]. J Nat Prod, 2016, 79(11): 2941-2952. DOI:10.1021/acs.jnatprod.6b00801
Zhang H, Zhang CR, Han YS, et al. New Securinega alkaloids with anti-HIV activity from Flueggea virosa[J]. RSC Adv, 2015, 5(129): 107045-107053. DOI:10.1039/C5RA22191A
Ma XH, Peng JX, Wu GW, et al. Speradines B-D, oxygenated cyclopiazonic acid alkaloids from the sponge-derived fungus Aspergillus flavus MXH-X104[J]. Tetrahedron, 2015, 71(21): 3522-3527. DOI:10.1016/j.tet.2015.03.050
Han WB, Zhang AH, Deng XZ, et al. Curindolizine, an anti-inflammatory agent assembled via Michael addition of pyrrole alkaloids inside fungal cells[J]. Org Lett, 2016, 18(8): 1816-1819. DOI:10.1021/acs.orglett.6b00549
Tian J, Han C, Guo WH, et al. Nigegladines A-C, three thymoquinone dimers from Nigella glandulifera[J]. Org Lett, 2017, 19(23): 6348-6351. DOI:10.1021/acs.orglett.7b03189
Sai CM, Li DH, Xue CM, et al. Two pairs of enantiomeric alkaloid dimers from Macleaya cordata[J]. Org Lett, 2015, 17(16): 4102-4105. DOI:10.1021/acs.orglett.5b02044
Zhang W, Huang XJ, Zhang SY, et al. Geleganidines A-C, unusual monoterpenoid indole alkaloids from Gelsemium elegans[J]. J Nat Prod, 2015, 78(8): 2036-2044. DOI:10.1021/acs.jnatprod.5b00351
Liu BY, Zhang C, Zeng KW, et al. Exotines A and B, two heterodimers of isopentenyl-substituted indole and coumarin derivatives from Murraya exotica[J]. Org Lett, 2015, 17(17): 4380-4383. DOI:10.1021/acs.orglett.5b02230
Zhou M, Zhou K, Gao XM, et al. Fistulains A and B, new bischromones from the bark of Cassia fistula, and their activities[J]. Org Lett, 2015, 17(11): 2638-2641. DOI:10.1021/acs.orglett.5b01007
Cao P, Yang J, Miao CP, et al. New duclauxamide from Penicillium manginii YIM PH30375 and structure revision of the duclauxin family[J]. Org Lett, 2015, 17(5): 1146-1149. DOI:10.1021/acs.orglett.5b00081
Wang KB, Li DH, Hu P, et al. A series of β-carboline alkaloids from the seeds of Peganum harmala show G-quadruplex interactions[J]. Org Lett, 2016, 18(14): 3398-3401. DOI:10.1021/acs.orglett.6b01560
Jia YL, Wei MY, Chen HY, et al. (+)- and (—)-Pestaloxazine A, a pair of antiviral enantiomeric alkaloid dimers with a symmetric spiro[oxazinane-piperazinedione] skeleton from Pestalotiopsis sp[J]. Org Lett, 2015, 17(17): 4216-4219. DOI:10.1021/acs.orglett.5b01995
Geng CA, Huang XY, Ma YB, et al. (±)-Uncarilins A and B, dimeric isoechinulin-type alkaloids from Uncaria rhynchophylla[J]. J Nat Prod, 2017, 80(4): 959-964. DOI:10.1021/acs.jnatprod.6b00938
Yuan YX, Zhang Y, Guo LL, et al. Tabercorymines A and B, two vobasinyl- ibogan-type bisindole alkaloids from Tabernaemontana corymbosa[J]. Org Lett, 2017, 19(18): 4964-4967. DOI:10.1021/acs.orglett.7b02445
Bao MF, Zeng CX, Liu YP, et al. Indole alkaloids from Hunteria zeylanica[J]. J Nat Prod, 2017, 80(4): 790-797. DOI:10.1021/acs.jnatprod.5b01035
Wang KB, Li SG, Huang XY, et al. (±)-Peharmaline A: a pair of rare β-carboline- vasicinone hybrid alkaloid enantiomers from Peganum harmala[J]. Eur J Org Chem, 2017, 2017(14): 1876-1879. DOI:10.1002/ejoc.201700137
Zhang YB, Zhan LQ, Li GQ, et al. Dimeric matrine-type alkaloids from the roots of Sophora flavescens and their anti-hepatitis B virus activities[J]. J Org Chem, 2016, 81(15): 6273-6280. DOI:10.1021/acs.joc.6b00804
Zhang W, Xu W, Wang GY, et al. Gelsekoumidines A and B: two pairs of atropisomeric bisindole alkaloids from the roots of Gelsemium elegans[J]. Org Lett, 2017, 19(19): 5194-5197. DOI:10.1021/acs.orglett.7b02463
Liu W, Li HJ, Xu MY, et al. Pseudellones A-C, three alkaloids from the marine-derived fungus Pseudallescheria ellipsoidea F42-3[J]. Org Lett, 2015, 17(21): 5156-5159. DOI:10.1021/acs.orglett.5b02311
Meng LH, Wang CY, Mándi A, et al. Three diketopiperazine alkaloids with spirocyclic skeletons and one bisthiodiketopiperazine derivative from the mangrove-derived endophytic fungus Penicillium brocae MA-231[J]. Org Lett, 2016, 18(20): 5304-5307. DOI:10.1021/acs.orglett.6b02620
Liu Y, Li XM, Meng LH, et al. Bisthiodiketopiperazines and acorane sesquiterpenes produced by the marine-derived fungus Penicillium adametzioides AS-53 on different culture media[J]. J Nat Prod, 2015, 78(6): 1294-1299. DOI:10.1021/acs.jnatprod.5b00102
Zhu ML, Zhang XM, Feng HM, et al. Penicisulfuranols A-F, alkaloids from the mangrove endophytic fungus Penicillium janthinellum HDN13-309[J]. J Nat Prod, 2017, 80(1): 71-75. DOI:10.1021/acs.jnatprod.6b00483
Zhang XF, Chen L, Chai WY, et al. A unique indolizinium alkaloid streptopertusacin A and bioactive bafilomycins from marine-derived Streptomyces sp. HZP- 2216E[J]. Phytochemistry, 2017, 144: 119-126. DOI:10.1016/j.phytochem.2017.09.010
Chen CM, Zhu HC, Wang JP, et al. Armochaetoglobins K-R, anti-HIV pyrrole-based cytochalasans from Chaetomium globosum TW1-1[J]. Eur J Org Chem, 2015, 2015(14): 3086-3094. DOI:10.1002/ejoc.201403678
Chen CM, Zhu HC, Li XN, et al. Armochaeglobines A and B, two new indole-based alkaloids from the arthropod-derived fungus Chaetomium globosum[J]. Org Lett, 2015, 17(3): 644-647. DOI:10.1021/ol503666b
Wang JF, Wang Z, Ju ZR, et al. Cytotoxic cytochalasins from marine-derived fungus Arthrinium arundinis[J]. Planta Med, 2015, 81(2): 160-166. DOI:10.1055/s-00000058
Li XY, Zhao ZH, Ding WJ, et al. Aspochalazine A, a novel polycyclic aspochalasin from the fungus Aspergillus sp. Z4[J]. Tetrahedron Lett, 2017, 58(25): 2405-2408. DOI:10.1016/j.tetlet.2017.04.071
Wei GZ, Chen CM, Tong QY, et al. Aspergilasines A-D: four merocytochalasans with new carbon skeletons from Aspergillus flavipes QCS12[J]. Org Lett, 2017, 19(16): 4399-4402. DOI:10.1021/acs.orglett.7b02146
Zhu HC, Chen CM, Tong QY, et al. Epicochalasines A and B: two bioactive merocytochalasans bearing caged epicoccine dimer units from Aspergillus flavipes[J]. Angew Chem Int Edit, 2016, 55(10): 3486-3490. DOI:10.1002/anie.201511315
Zhu HC, Chen CM, Tong QY, et al. Asperflavipine A: a cytochalasan heterotetramer uniquely defined by a highly complex tetradecacyclic ring system from Aspergillus flavipes QCS12[J]. Angew Chem Int Edit, 2017, 56(19): 5242-5246. DOI:10.1002/anie.201701125
Wang WG, Li A, Yan BC, et al. LC-MS-guided isolation of penicilfuranone A: a new antifibrotic furancarboxylic acid from the plant endophytic fungus Penicillium sp. sh18[J]. J Nat Prod, 2016, 79(1): 149-155. DOI:10.1021/acs.jnatprod.5b00814
Wang CX, Ding R, Jiang ST, et al. Aldgamycins J-O, 16-membered macrolides with a branched octose unit from Streptomycetes sp. and their antibacterial activities[J]. J Nat Prod, 2016, 79(10): 2446-2454. DOI:10.1021/acs.jnatprod.6b00200
Liu L, Han Y, Xiao JH, et al. Chlorotheolides A and B, spiroketals generated via Diels-Alder reactions in the endophytic fungus Pestalotiopsis theae[J]. J Nat Prod, 2016, 79(10): 2616-2623. DOI:10.1021/acs.jnatprod.6b00550
Zhou XM, Zheng CJ, Gan LS, et al. Bioactive phenanthrene and bibenzyl derivatives from the stems of Dendrobium nobile[J]. J Nat Prod, 2016, 79(7): 1791-1797. DOI:10.1021/acs.jnatprod.6b00252
Long HL, Cheng ZB, Huang W, et al. Diasteltoxins A-C, asteltoxin-based dimers from a mutant of the sponge-associated Emericella variecolor fungus[J]. Org Lett, 2016, 18(18): 4678-4681. DOI:10.1021/acs.orglett.6b02313
Xie ZP, Zhou L, Guo L, et al. Grisemycin, a bridged angucyclinone with a methylsulfinyl moiety from a marine-derived Streptomyces sp[J]. Org Lett, 2016, 18(6): 1402-1405. DOI:10.1021/acs.orglett.6b00332
Zhang AH, Tan R, Jiang N, et al. Selesconol, a fungal polyketide that induces stem cell differentiation[J]. Org Lett, 2016, 18(21): 5488-5491. DOI:10.1021/acs.orglett.6b02688
Zhai MM, Qi FM, Li J, et al. Isolation of secondary metabolites from the soil- derived fungus Clonostachys rosea YRS-06, a biological control agent, and evaluation of antibacterial activity[J]. J Agric Food Chem, 2016, 64(11): 2298-2306. DOI:10.1021/acs.jafc.6b00556
Yin GP, Wu YR, Yang MH, et al. Citrifurans A-D, four dimeric aromatic polyketides with new carbon skeletons from the fungus Aspergillus sp[J]. Org Lett, 2017, 19(15): 4058-4061. DOI:10.1021/acs.orglett.7b01823
Guo YY, Li H, Zhou ZX, et al. Identification and biosynthetic characterization of natural aromatic azoxy products from Streptomyces chattanoogensis L10[J]. Org Lett, 2015, 17(24): 6114-6117. DOI:10.1021/acs.orglett.5b03137
Shao SY, Feng ZM, Yang YN, et al. Forsythenethosides A and B: two new phenylethanoid glycosides with a 15-membered ring from Forsythia suspensa[J]. Org Biomol Chem, 2017, 15(33): 7034-7039. DOI:10.1039/C7OB01811H
Xiao YS, Zhang B, Zhang M, et al. Rifamorpholines A-E, potential antibiotics from locust-associated actinobacteria Amycolatopsis sp. Hca4[J]. Org Biomol Chem, 2017, 15(18): 3909-3916. DOI:10.1039/C7OB00614D
Zhang DW, Zhao LL, Wang LN, et al. Griseofulvin derivative and indole alkaloids from Penicillium griseofulvum CPCC 400528[J]. J Nat Prod, 2017, 80(2): 371-376. DOI:10.1021/acs.jnatprod.6b00829
Yang PF, Feng ZM, Yang YN, et al. Neuroprotective caffeoylquinic acid derivatives from the flowers of Chrysanthemum morifolium[J]. J Nat Prod, 2017, 80(4): 1028-1033. DOI:10.1021/acs.jnatprod.6b01026
Xu K, Feng ZM, Yang YN, et al. Two new compounds from rhizomes of Atractylodes lancea[J]. Chin J Org Chem, 2017, 37(11): 3019-3023. DOI:10.6023/cjoc201706031
Wang ZY, Sang XN, Sun K, et al. Lecanicillones A-C, three dimeric isomers of spiciferone A with a cyclobutane ring from an entomopathogenic fungus Lecanicillium sp. PR-M-3[J]. RSC Adv, 2016, 6(85): 82348-82351. DOI:10.1039/C6RA11422A
Zhang XP, Chen CY, Li YH, et al. Tadehaginosides A-J, phenylpropanoid glucosides from Tadehagi triquetrum, enhance glucose uptake via the upregulation of PPARγ and GLUT-4 in C2C12 myotubes[J]. J Nat Prod, 2016, 79(5): 1249-1258. DOI:10.1021/acs.jnatprod.5b00820
Yang CF, Huang CS, Zhang WJ, et al. Heterologous expression of fluostatin gene cluster leads to a bioactive heterodimer[J]. Org Lett, 2015, 17(21): 5324-5327. DOI:10.1021/acs.orglett.5b02683
Fan AL, Mi WB, Liu ZG, et al. Deletion of a Histone acetyltransferase leads to the pleiotropic activation of natural products in Metarhizium robertsii[J]. Org Lett, 2017, 19(7): 1686-1689. DOI:10.1021/acs.orglett.7b00476
Hu JF, Garo E, Yoo HD, et al. Application of capillary-scale NMR for the structure determination of phytochemicals[J]. Phytochem Anal, 2015, 16(2): 127-133.
Hu JF, Eldridge GR, Yu YH, et al. High-throughput natural product chemistry methods and the application of the capillary NMR probe[J]. Prog Chem, 2008, 20(4): 429-440.