CN: 32-1845/R
ISSN: 2095-6975
Cite this paper:
0
MEI Yu-Dan, ZHANG Nan, ZHANG Wei-Yang, TANG Jin-Shan, ZHOU Hua, YU Yang, YAO Xin-Sheng. Two new ursane-type nortriterpenes from Lonicera macranthoides and their iNOS-inhibitory activities[J]. Chinese Journal of Natural Medicines, 2019, 17(1): 27-32

Two new ursane-type nortriterpenes from Lonicera macranthoides and their iNOS-inhibitory activities

MEI Yu-Dan1,4, ZHANG Nan2, ZHANG Wei-Yang3, TANG Jin-Shan1, ZHOU Hua3, YU Yang1, YAO Xin-Sheng1,2
1 Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China;
2 College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China;
3 Faculty of Chinese Medicine, Macau University of Science and Technology and State Key Laboratory of Quality Research in Chinese Medicine(Macau University of Science and Technology), Macau 999078, China;
4 XiangXue Academician workstation, Xiangxue Pharmaceutical Co., Ltd., Guangzhou 510663, China
Abstract:
The flower buds of Lonicera macranthoides (Shan Yin-Hua), represent an important traditional Chinese medicine and food ingredient. A phytochemical investigation of the 70% EtOH extract of the flower buds of L. macranthoides resulted in the isolation of 12 triterpenoids (1-12), including two new ursane-type nortriterpenes, 2α, 24-dihydroxy-23-nor-ursolic acid (1) and 2α, 4α-dihydroxy-23-nor-ursolic acid (2). Their structures were established by multiple spectroscopic methods and comparison with literature data. All isolated compounds were evaluated for their anti-inflammatory effects in LPS-activated RAW264.7 cells. Compounds 1 and 2 exhibited inhibitory effects on iNOS at the concentration of 30 μmol·L-1.
Key words:    Lonicerae Flos    Lonicera macranthoides    Ursane-type nortriterpenes    Anti-inflammation    iNOS   
Received: 2018-09-10   Revised:
Tools
PDF (727 KB) Free
Print this page
Email this article to others
Authors
Articles by MEI Yu-Dan
Articles by ZHANG Nan
Articles by ZHANG Wei-Yang
Articles by TANG Jin-Shan
Articles by ZHOU Hua
Articles by YU Yang
Articles by YAO Xin-Sheng
References:
[1] Hu X, Chen L, Shi S, et al. Antioxidant capacity and phenolic compounds of Lonicerae macranthoides by HPLC-DAD-QTOF-MS/MS[J]. J Pharm Biomed Anal, 2016, 124:254-260.
[2] Liu X, Zhou R, Shen B, et al. Determination and isolation of four anti-tumor saponins from Lonicera macranthoides by HPLC-ESI-QTOF/MS and HSCCC[J]. Curr Pharm Biotechnol, 2018, 19(13):1106-1114.
[3] Yu S, Guan F, Zhao X, et al. Macranthoside B induces apoptosis and autophagy via reactive oxygen species accumulation in human ovarian cancer A2780 cells[J]. Nutr Cancer, 2016, 68(2):280-289.
[4] Wang J, Zhao XZ, Qi Q, et al. Macranthoside B, a hederagenin saponin extracted from Lonicera macranthoides and its anti-tumor activities in vitro and in vivo[J]. Food Chem Toxicol, 2009, 47(7):1716-1721.
[5] Shi JZ, Liu GT. Effect of α-hederin and sapindoside B on hepatic microsomal cytochrome P-450 in mice[J]. Acta Pharmacol Sin, 1996, 17(3):264-266.
[6] Guan F, Wang H, Shan Y, et al. Inhibition of COX-2 and PGE2 in LPS-stimulated RAW264.7 cells by lonimacranthoide VI, a chlorogenic acid ester saponin[J]. Biomed Rep, 2014, 2(5):760.
[7] Liu J, Zhang J, Wang F, et al. Chemical constituents from the buds of Lonicera macranthoides in Sichuan, China[J]. Biochem Syst Ecol, 2014, 54:68-70.
[8] Liu J, Zhang J, Wang F, et al. New secoiridoid glycosides from the buds of Lonicera macranthoides[J]. Nat Prod Commun, 2012, 7(12):1561-1562.
[9] Chen Y, Zhao Y, Wang M, et al. The first chlorogenic acid ester saponin from Lonicera macranthoides[J]. Chem Nat Compd, 2012, 47(6):940-943.
[10] Liu J, Zhang J, Wang F, et al. Isolation and characterization of new minor triterpenoid saponins from the buds of Lonicera macranthoides[J]. Carbohydr Res, 2013, 370(7):76-81.
[11] Chen Y, Zhao Y, Wang M, et al. A new lupane-type triterpenoid saponin from Lonicera macranthoides[J]. Chem Nat Compd, 2014, 49(6):1087-1090.
[12] Jia XD, Feng X, Zhao XZ, et al. Studies on the chemical constituents of Lonicra macranthoides[J]. Chin Tradit Herb Drugs, 2008, 39(11):1635-1636.
[13] Chen Y, Feng X, Wang M, et al. Triterpene glycosides from Lonicera Ⅱ. Isolation and structural determination of glycosides from buds of Lonicera macranthoides[J]. Chem Nat Compd, 2009, 4(45):514-519.
[14] Chen Y, Feng X, Jia X, et al. Triterpene glycosides from Lonicera isolation and structural determination of seven glycosides from flower buds of Lonicera macranthoides[J]. Chem Nat Compd, 2008, 44(1):39-43.
[15] Chen Y, Shan Y, Zhao Y, et al. Two new triterpenoid saponins from Lonicera macranthoides[J]. Chin Chem Lett, 2012, 23(3):325-328.
[16] Chen CY, Qi LW, Li HJ, et al. Simultaneous determination of iridoids, phenolic acids, flavonoids, and saponins in Flos Lonicerae and Flos Lonicerae japonicae by HPLC-DAD-ELSD coupled with principal component analysis[J]. J Sep Sci, 2007, 30:3181-3192.
[17] Teng RW, Wang DZ, Chen CX. Two triterpenoid saponins from Lonicera japonica[J]. Chin Chem Lett, 2000, 11(4):337-340.
[18] Wang HB, Mayer R, Rücker G. Triterpenoid glycosides from Stauntonia hexaphylla[J]. Phytochemistry, 1993, 34(5):1389-1394.
[19] Panov DA, Grishkovets VI, Kachala VV, et al. Triterpene glycosides from Kalopanax septemlobum. VⅡ. Minor glycosides from stems of Kalopanax septemlobum var. maximowiczii and Kalopanax septemlobum var. typicum[J]. Chem Nat Compd, 2006, 42(1):61-66.
[20] Kawai H, Kuroyanagi M, Umehara K, et al. Studies on the saponins of Lonicera japonica Thunb[J]. Cheml Pharm Bull, 1988, 36(12):4769.
[21] Bang SC, Kim Y, Lee JH, et al. Triterpenoid saponins from the roots of Pulsatilla koreana[J]. J Nat Prod, 2005, 68(2):268-272.
[22] Bisoli E, Garcez WS, Hamerski L, et al. Bioactive pentacyclic triterpenes from the stems of Combretum laxum[J]. Molecules, 2008, 13(11):2717-2728.
[23] Kawahara K, Hohjoh H, Inazumi T, et al. Prostaglandin E2-induced inflammation:Relevance of prostaglandin E receptors[J]. Biochim Biophys Acta, 2015, 1851(4):414.
[24] Aktan F. iNOS-mediated nitric oxide production and its regulation[J]. Life Sci, 2004, 75(6):639.