CN: 32-1845/R
ISSN: 2095-6975
Cite this paper:
0
GU Xiao-Jie, HAO Da-Cheng. Recent advances in phytochemistry and pharmacology of C21 steroid constituents from Cynanchum plants[J]. Chinese Journal of Natural Medicines, 2016, 14(5): 321-334

Recent advances in phytochemistry and pharmacology of C21 steroid constituents from Cynanchum plants

GU Xiao-Jie, HAO Da-Cheng
Biotechnology Institute, School of Environment, Dalian Jiaotong University, Dalian 116028, China
Abstract:
Cynanchum is one of the most important genera in Asclepiadaceae family, which has long been known for its therapeutic effects. In this genus, 16 species are of high medicinal value. The extracts of the root and/or rhizome parts have been applied in traditional Chinese medicines (TCM) for the prevention and treatment of various illnesses for centuries. C21 steroids, as the typical constituents of Cynanchum species, possess a variety of structures and pharmacological activities. This review summarizes the comprehensive information on phytochemistry and pharmacology of C21 steroid constituents from Cynanchum plants, based on reports published between 2007 and 2015. Our aim is to provide a rationale for their therapeutic application, and to discuss the future trends in research and development of these compounds. A total of 172 newly identified compounds are reviewed according to their structural classifications. Their in vitro and in vivo pharmacological studies are also reviewed and discussed, focusing on antitumor, antidepressant, antifungal, antitaging, Na+/K+-ATPase inhibitory, appetite suppressing and antiviral activities. Future research efforts should concentrate on in vitro and in vivo biological studies and structure activity relationship of various C21 steroid constituents.
Key words:    Asclepiadaceae    Cynanchum    C21 steroid constituents    Phytochemical studies    Pharmacological actions   
Received: 2015-06-04   Revised:
Tools
PDF (662 KB) Free
Print this page
Email this article to others
Authors
Articles by GU Xiao-Jie
Articles by HAO Da-Cheng
References:
[1] Li PT, Michael GG, Stevens WD. In: Flora of China [M]. Beijing: Science Press: 1995: 205-223.
[2] The Chinese Traditional Medicine State Administration. Zhong Hua Ben Cao [M]. 3rd ed. Shanghai Science and Technology Publishing Company, 1999.
[3] Deepak D, Srivastav S, Khare A. In: Progress in the chemistry of organic natural products [M]. Springer Publishing Company, 1997, 71: 170-325.
[4] Wu ZJ, Ding LS, Zhao SX. Recent advance in the chemical and biological studies of Cynanchum plants [J]. World Phytomed Plant Med, 1991, 6(4): 147-154.
[5] Liu WW, Zhang CH, Wu LY, et al. Advance on chemical constituents and pharmacological activities of Cynanchum plants [J]. J Chin Med Mat, 2003, 26(3): 216-217.
[6] Wu Y, Zhou HL. Advance on chemical constituents of Cynanchum plants [J]. Central South Pharm, 2006, 4(5): 371-375.
[7] Bai H, Wang YS, Liu AQ. Advance study on the C21 steroid constituents of Cynanchum plants [J]. Nat Prod Res Dev, 2007, 19(5): 897-904.
[8] Ni Y, Ye YP. Distribution of C21 steroidal glycosides in plants of Asclepiadaceae and their pharmacological activities [J]. Chin Tradit Herb Drugs, 2010, 41(1): 162-165.
[9] Liu SG, Chen ZH, Wu J, et al. Appetite suppressing pregnane glycosides from the roots of Cynanchum auriculatum [J]. Phytochemistry, 2013, 93: 144-153.
[10] Yoon MY, Choi NH, Min BS, et al. Potent in vivo antifungal activity against powdery mildews of pregnane glycosides from the roots of Cynanchum wilfordii [J]. J Agric Food Chem, 2011, 59: 12210-12216.
[11] Chen G, Xu N, Pei YH. C21 steroidal glycosides from Cynanchum wallichii Wight [J]. J Asian Nat Prod Res, 2009, 11(2): 177-182.
[12] Gu XJ, Yao N, Qian SH, et al. Four new C21 steroidal glycosides from the roots of Cynanchum auriculatum [J]. Helv Chim Acta, 2009, 92: 88-97.
[13] Li YB, Zhang JF, Gu XJ, et al. Two new cytotoxic pregnane glycosides from Cynanchum auriculatum [J]. Plant Med, 2008, 74: 551-554.
[14] Huang LJ, Wang B, Zhang JX, et al. Studies on cytotoxic pregnane sapogenins from Cynanchum wilfordii [J]. Fitoterapia, 2015, 101: 107-116.
[15] Lu Y, Teng HL, Yang GZ, et al. Three new steroidal glycosides from the roots of Cynanchum auriculatum [J]. Molecules, 2011, 16: 1901-1909.
[16] Ma XX, Wang D, Zhang YJ, et al. Identification of new qingyangshengenin and caudatin glycosides from the roots of Cynanchum otophyllum [J]. Steroids, 2011, 76: 1003-1009.
[17] Yang QX, Ge YC, Huang XY, et al. Cynanauriculoside C-E, three new antidepressant pregnane glycosides from Cynanchum auriculatum [J]. Phytochem Lett, 2011, 4: 170-175.
[18] Chen G, Xu N, Li Z.F, et al. Steroidal glycosides with anti-tumor activity from the roots of Cynanchum wallichii Wight [J]. J Asian Nat Prod Res, 2010, 12(6): 453-457.
[19] Ma XX, Jiang FT, Yang QX, et al. New pregnane glycosides from the roots of Cynanchum otophyllum [J]. Steroids, 2007, 72: 778-786.
[20] Yang XX, Bao YR, Wang LF, et al. Two new steroidal glycosides from Cynanchum otophyllum Schneid [J]. J Asian Nat Prod Res, 2015, 17(3): 285-288.
[21] Chen G, Wang D, Pei YH. Two new C21 steroidal glycosides from Cynanchum wallichii Wight [J]. J Asian Nat Prod Res, 2008, 10(7): 671-676.
[22] Zhao YB, He HP, Lu CH, et al. C21 steroidal glycosides of seven sugar residues from Cynanchum otophyllum [J]. Steroids, 2006, 71: 935-941.
[23] Li X, Zhang M, Xiang C, et al. Antiepileptic C21 steroids from the roots of Cynanchum otophyllum [J]. J Asian Nat Prod Res, 2015, 12(1): 1-9.
[24] Wang D, Pan WH, Bao YR, et al. Two new steroidal glycosides from Cynanchum wallichii [J]. J Asian Nat Prod Res, 2014, 16(7): 759-763.
[25] Teng HL, Lu Y, Li J, et al. Two new steroidal glycosides from the root of Cynanchum auriculatum [J]. Chin Chem Lett, 2011, 22: 77-80.
[26] Yu JQ, Deng AJ, Qin HL. Nine new steroidal glycosides from the roots of Cynanchum stauntonii [J]. Steroids, 2013, 78: 79-90.
[27] Yu JQ, Zhang ZH, Deng AJ, et al. Three new steroidal glycosides from the roots of Cynanchum stauntonii [J]. Bio Med Res Int, 2013, ID: 816145, 1-6.
[28] Makio S, Ayaka M, Kayoko S, et al. Two secopregnane-type steroidal glycosides from Cynanchum stauntonii (Gecne.) [J]. Phytochem Lett, 2012, 5: 304-308.
[29] Tsutomu W, Tadataka N. Glycosides of 14,15-seco and 13,14:14,15-disecopregnanes from the roots of Cynanchum sublanceolatum [J]. Chem Pharm Bull, 2006, 54(11): 1551-1560.
[30] Liu Y, Qu J, Hu YC, et al. Seven new steroidal glycosides from the roots of Cynanchum forrestii [J]. Steroids, 2007, 72: 313-322.
[31] Fu MH, Wang ZJ, Yang HJ, et al. A new C21 steroidal glycosides from Cynanchum stauntonii [J]. Chin Chem Lett, 2007, 18: 415-417.
[32] Wang LQ, Wang JH, Shen YM, et al. Three new C21 steroidal glycosides from the roots of Cynanchum inamoenum [J]. Chem Lett, 2007, 18: 1235-1238.
[33] Yan Y, Zhang JX, Liu KX, et al. Seco-pregnane steroidal glycosides from the roots of Cynanchum atratum and their anti-TMV activity [J]. Fitoterapia, 2014, 97: 50-63.
[34] Chen H, Xu N, Zhou YZ, et al. Steroidal glycosides from the roots of Cynanchum amplexicaule Sieb. et Zucc [J]. Steroids, 2008, 73: 629-636.
[35] Li XY, Sun XH, Ye YP, et al. C21 steroidal glycosides from the roots of Cynanchum chekiangense and their immuno­suppressive activities [J]. Steroids, 2006, 71: 61-66.
[36] Kim CS, Oh JY, Choi SU, et al. Chemical constituents from the roots of Cynanchum paniculatum and their cytotoxic activity [J]. Carbohydr Res, 2013, 381: 1-5.
[37] Wang LQ, Lu Y, Zhao YX, et al. Three new C21 steroidal glycosides from the roots of Cynanchum inamoenum [J]. J Asian Nat Prod Res, 2007, 9(8): 771-779.
[38] Zhang M, Wang JS, Luo J, et al. Glaucogenin E, a new C21 steroid from Cynanchum stauntonii [J]. Nat Prod Res, 2013, 27(2): 176-180.
[39] Dou J, Li P, Bi ZM, et al. New C21 steroidal glycosides from Cynanchum paniculatum [J]. Chin Chem Lett, 2007, 18: 300-302.
[40] Chen G, Chen H, Li W, et al. Steroidal glycosides from Cynanchum amplexicaule [J]. J Asian Nat Prod Res, 2011, 13(8): 756-760.
[41] Chen G, Chen H, Li W, et al. Steroidal glycosides from Cynanchum amplexicaule [J]. Chem Nat Comp, 2012, 48(6): 1021-1023.
[42] Chen G, Yi S, Hua HM, et al. Two new steroidal glycosides from Cynanchum amplexicaule [J]. J Asian Nat Prod Res, 2012, 14(6): 559-563.
[43] Wang LQ, Shen YM, Hu JM, et al. A new C21 steroidal glycosides from Cynanchum inamoenum [J]. J Asian Nat Prod Res, 2008, 10(9): 867-871.
[44] Bai H, Li W, Asada Y, et al. Twelve pregnane glycosides from Cynanchum atratum [J]. Steroids, 2009, 74: 198-207.
[45] Bai H, Li W, Koike K. Pregnane glycosides from Cynanchum atratum [J]. Steroids, 2008, 73: 96-103.
[46] Fei HR, Chen HL, Xiao T, et al. Caudatin induces cell cycle arrest and caspase-dependent apoptosis in HepG2 cell [J]. Mol Biol Rep, 2012, 39: 131-138.
[47] Wang YQ, Yang B, Zhang RS, et al. Inhibitive effect of C-21 steroidal glycosides of Cynanchum auriculatum on rat glioma cells in vitro [J]. J Zhejiang Univ (Med Sci), 2011, 40(4): 402-407.
[48] Wang DY, Zhang HQ, Li, X. Apoptosis induced by the C21 steroidal glycosides in Baishouwu and its mechanism of action in hepatoma [J]. Acta Pharm Sin, 2007, 42(4): 366-370.
[49] Yao N, Gu XJ, Li YB. Effects of three C21 steroidal saponins from Cynanchum auriculatum on cell growth and cell cycle of human lung cancer A549 cells [J]. Chin J Chin Mat Med, 2009, 34(11): 1418-1421.
[50] Xu W, Shan L, Liu X, et al. Determination of two C21 steroidal glycosides of Baishouwu and their metabolites in mice plasma and tumor humogenate by liquid chromatography-tandem mass spectrometry [J]. J Chromatogr B Anal Tech Biomed Life Sci, 2008, 876: 203-210.
[51] Liu KY, Chen F, Zhang HQ. Antitumor effects by Wilfoside C3N treatment in ECA109 cells [J]. Anti-Caner Drugs, 2010, 21: 625-631.
[52] Peng YR, Li YB, Liu XD, et al. Antitumor activity of C-21 steroidal glycosides from Cynanchum auriculatum Royle ex Wight [J]. Phytomedicine, 2008, 15: 1016-1020.
[53] Peng YR, Ding YF, Wei YJ, et al. Caudatin-2, 6-dideoxy-3-O-methy-β-D-cymaropyranoside 1 induced apoptosis through caspase 3-dependent pathway in human hepatoma cell line SMMC7721 [J]. Phytother Res, 2011, 25: 631-637.
[54] Zhang RS, Liu YL, Wang YQ, et al. Cytotoxic and apoptosis-inducing properties of auriculoside A in tumor cells [J]. Chem Biodiver, 2007, 4: 887-892.
[55] Ye LF, Wang YQ, Yang B, et al. Cytotoxic and apoptosis-inducing properties of a C21-steroidal glycoside isolated from the roots of Cynanchum auriculatum [J]. Oncology Lett, 2013, 5: 1407-1411.
[56] Ji CX, Li XY, Jia SB, et al. The antidepressant effect of Cynanchum auriculatum in mice [J]. Pharm Biol, 2012, 50(9): 1067-1072.
[57] Zhang SX, Li X, Yin JL, et al. Effect of C21 steroidal glycosides from root of Cynanchum auriculatum on D-galactose induced aging model mice [J]. Chin J Chin Mat Med, 2007, 32(23): 2511-2514.
[58] Van Heerden FR, Horak RM, Mahara JV, et al. An appetite suppressant from Hoodia species [J]. Phytochemistry, 2007, 68: 2545-2553.
[59] Li YM, Wang LH, Li SL, et al. Seco-pregnane steroids target the subgenomic RNA of alphavirus-like RNA viruses [J]. Proc Nat Acade Sci Am, 2007, 104(19): 8083-8088.