CN: 32-1845/R
ISSN: 2095-6975
Cite this paper:
LUO Xiao-Wei, LIN Yun, LU Yong-Jun, ZHOU Xue-Feng, LIU Yong-Hong. Peptides and polyketides isolated from the marine sponge-derived fungus Aspergillus terreus SCSIO 41008[J]. Chinese Journal of Natural Medicines, 2019, 17(2): 149-154

Peptides and polyketides isolated from the marine sponge-derived fungus Aspergillus terreus SCSIO 41008

LUO Xiao-Wei1,2, LIN Yun3,4, LU Yong-Jun3,4, ZHOU Xue-Feng1,2, LIU Yong-Hong1,2
1 CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China;
2 University of Chinese Academy of Sciences, Beijing 100049, China;
3 School of Life Sciences, Sun Yat-Sen University, Guangzhou 510275, China;
4 Biomedical Center of Sun Yat-Sen University, Guangzhou 510275, China
Two new isomeric modified tripeptides, aspergillamides C and D (compounds 1 and 2), together with fifteen known compounds (compounds 3-17), were obtained from the marine sponge-derived fungus Aspergillus terreus SCSIO 41008. The structures of the new compounds, including absolute configurations, were determined by extensive analyses of spectroscopic data (NMR, MS, UV, and IR) and comparisons between the calculated and experimental electronic circular dichroism (ECD) spectra. Butyrolactone I (compound 11) exhibited strong inhibitory effects against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with the IC50 being 5.11 ± 0.53 μmol·L-1, and acted as a noncompetitive inhibitor based on kinetic analysis.
Key words:    Aspergillus terreus    Aspergillamides    Polyketides    MptpB inhibitor   
Received: 2018-07-17   Revised:
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Articles by LIU Yong-Hong
[1] Cheung RCF, Ng TB, Wong JH. Marine peptides:bioactivities and applications[J]. Mar Drugs, 2015, 13(7):4006-4043.
[2] Pangestuti R, Kim SK. Bioactive peptide of marine origin for the prevention and treatment of non-communicable diseases[J]. Mar Drugs, 2017, 15(3):67.
[3] Toske SG, Jensen PR, Kauffman CA, et al. Aspergillamides A and B:modified cytotoxic tripeptides produced by a marine fungus of the genus Aspergillus[J]. Tetrahedron, 1998, 54(44):13459-13466.
[4] Shiomi K, Hatae K, Yamaguchi Y, et al. New antibiotics miyakamides produced by a fungus[J]. J Antibiot, 2002, 55(11):952-961.
[5] Zhang HW, Zhao ZP, Wang H. Cytotoxic natural products from marine sponge-derived microorganisms[J]. Mar Drugs, 2017, 15(3):68.
[6] Indraningrat AAG, Smidt H, Sipkema D. Bioprospecting sponge-associated microbes for antimicrobial compounds[J]. Mar Drugs, 2016, 14(5):87.
[7] Blunt JW, Carroll AR, Copp BR, et al. Marine natural products[J]. Nat Prod Rep, 2018, 35(1):8-53.
[8] Subhan M, Faryal R, Macreadie I. Exploitation of Aspergillus terreus for the production of natural statins[J]. J Fungi, 2016, 2(2):13.
[9] Guo F, Li ZL, Xu XW, et al. Butenolide derivatives from the plant endophytic fungus Aspergillus terreus[J]. Fitoterapia, 2016, 113:44-50.
[10] Parvatkar RR, D'Souza C, Tripathi A, et al. Aspernolides A and B, butenolides from a marine-derived fungus Aspergillus terreus[J]. Phytochemistry, 2009, 70(1):128-132.
[11] Nong XH, Wang YF, Zhang XY, et al. Territrem and butyrolactone derivatives from a marine-derived fungus Aspergillus terreus[J]. Mar Drugs, 2014, 12(12):6113-6124.
[12] 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.
[13] 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.
[14] You MJ, Liao LJ, Hong SH, et al. Lumazine peptides from the marine-derived fungus Aspergillus terreus[J]. Mar Drugs, 2015, 13(3):1290-1303.
[15] He F, Bao J, Zhang XY, et al. Asperterrestide A, a cytotoxic cyclic tetrapeptide from the marine-derived fungus Aspergillus terreus SCSGAF0162[J]. J Nat Prod, 2013, 76(6):1182-1186.
[16] Cai SX, Du L, Gerea AL, et al. Spiro fused diterpene-indole alkaloids from a creek-bottom-derived Aspergillus terreus[J]. Org Lett, 2013, 15(16):4186-4189.
[17] Niu XM, Dahse HM, Menzel KD, et al. Butyrolactone I derivatives from Aspergillus terreus carrying an unusual sulfate moiety[J]. J Nat Prod, 2008, 71(4):689-692.
[18] 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.
[19] Igarashi M, Ishizaki Y, Takahashi Y. New antituberculous drugs derived from natural products:current perspectives and issues in antituberculous drug development[J]. J Antibiot, 2017, 71(1):15-25.
[20] Fang W, Wang JJ, Wang JF, et al. Cytotoxic and antibacterial eremophilane sesquiterpenes from the marine-derived fungus Cochliobolus lunatus SCSIO41401[J]. J Nat Prod, 2018, 81(6):1405-1410.
[21] Luo XW, Lin XP, Tao HM, et al. Isochromophilones A-F, cytotoxic chloroazaphilones from the marine mangrove endophytic fungus Diaporthe sp. SCSIO 41011[J]. J Nat Prod, 2018, 81(4):934-941.
[22] Tan YH, Yang B, Lin XP, et al. Nitrobenzoyl sesquiterpenoids with cytotoxic activities from a marine-derived Aspergillus ochraceus fungus[J]. J Nat Prod, 2018, 81(1):92-97.
[23] Rank C, Klejnstrup ML, Petersen LM, et al. Comparative chemistry of Aspergillus oryzae (RIB40) and A. flavus (NRRL 3357)[J]. Metabolites, 2012, 2(1):39-56.
[24] Adpressa DA, Loesgen S. Bioprospecting chemical diversity and bioactivity in a marine derived Aspergillus terreus[J]. Chem Biodivers, 2016, 13(2):253-259.
[25] Shen Y, Zou JH, Xie D, et al. Butyrolactone and cycloheptanetrione from mangrove-associated fungus Aspergillus terreus[J]. Chem Pharm Bull, 2012, 60(11):1437-1441.
[26] Li T, Wang GC, Huang XJ, et al. Whitmanoside A, a new alpha-pyrone glycoside from the leech whitmania pigra[J]. Heterocycles, 2013, 87(7):1537-1543.
[27] Asiri IAM, Badr JM, Youssef DTA. Penicillivinacine, antimigratory diketopiperazine alkaloid from the marine-derived fungus Penicillium vinaceum[J]. Phytochem Lett, 2015, 13:53-58.
[28] Haroon MH, Premaratne SR, Choudhry MI, et al. A new glucuronidase inhibiting butyrolactone from the marine endophytic fungus Aspergillus terreus[J]. Nat Prod Res, 2013, 27(12):1060-1066.
[29] Jo G, Shin SY, Lee Y, et al. A compound isolated from Rumex japonicus induces early growth response gene-I expression[J]. J Korean Soc Appl Biol Chem, 2011, 54(4):637-643.
[30] Liu DS, Yan L, Ma LY, et al. Diphenyl derivatives from coastal saline soil fungus Aspergillus iizukae[J]. Arch Pharm Res, 2015, 38(6):1038-1043.
[31] Hawas UW, El-Beih AA, El-Halawany AM. Bioactive anthraquinones from endophytic fungus Aspergillus versicolor isolated from red sea algae[J]. Arch Pharm Res, 2012, 35(10):1749-1756.
[32] Petit P, Lucas EMF, Abreu LM, et al. Novel antimicrobial secondary metabolites from a Penicillium sp. isolated from Brazilian cerrado soil[J]. Electron J Biotechn, 2009, 12(12):8-9.
[33] Krohn K, Bahramsari R, Florke U, et al. Dihydroisocoumarins from fungi:isolation, structure elucidation, circular dichroism and biological activity[J]. Phytochemistry, 1997, 45(2):313-320.
[34] Yun BR, Yang HJ, Weon JB, et al. Neuroprotective properties of compounds extracted from Dianthus superbus L. against glutamate-induced cell death in HT22 Cells[J]. Pharmacogn Mag, 2016, 12(46):109-113.
[35] Luo XW, Zhou XF, Lin XP, et al. Antituberculosis compounds from a deep-sea-derived fungus Aspergillus sp. SCSIO Ind09F01[J]. Nat Prod Res, 2017, 31(16):1958-1962.