New Steroidal Saponins and Sterol Glycosides from Paris polyphylla var. yunnanensis

Xia Wu; Lei Wang; Guo-Cai Wang; Hui Wang; Yi Dai; Wen-Cai Ye; Yao-Lan Li

doi:10.1055/s-0032-1315239

Planta Medica, Table of Contents

Planta Med 2012; 78(15): 1667-1675
DOI: 10.1055/s-0032-1315239

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

New Steroidal Saponins and Sterol Glycosides from Paris polyphylla var. yunnanensis

Authors

Xia Wu

¹Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou, PR China

²Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, PR China
Lei Wang

¹Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou, PR China

²Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, PR China
Guo-Cai Wang

¹Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou, PR China

²Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, PR China
Hui Wang

³School of Medicine, Jinan University, Guangzhou, PR China
Yi Dai

¹Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou, PR China

²Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, PR China
Wen-Cai Ye

¹Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou, PR China

²Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, PR China
Yao-Lan Li

¹Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou, PR China

²Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou, PR China

Abstract

Four new steroidal saponins, pariposides A–D (1–4), and two new sterol glycosides, pariposides E–F (5-6), along with eight known steroidal saponins (7-14), two known sterol glycosides (15–16), and two known ecdysteroids (17–18), were isolated from the roots of Paris polyphylla var. yunnanensis. Among them, compounds 1–4 are the first spirostanol saponins with a peroxy group located between C-5 and C-8 of the aglycone. Their structures were determined by detailed spectroscopic analyses and chemical methods. All the isolated compounds were evaluated for their in vitro cytotoxicities against human nasopharyngeal carcinoma epithelial (CNE) cells, and steroidal saponins 7, 11, 13, and 14 showed a potent antiproliferative effect on CNE cells with IC₅₀ values of 9.2, 4.7, 11.1, and 2.7 µM, respectively.

Key words

Paris polyphylla var. yunnanensis - Liliaceae - steroidal saponin - sterol glycoside - cytotoxic activities

Full Text

References

References
1 George F, Zohar K, Harinder PSM, Klaus B. The biological action of saponins in animal systems: a review. Brit J Nutr 2002; 88: 578-605
2 Xiao X, Bai P, Nguyen TMB, Xiao JG, Liu SL, Yang G, Hu L, Chen XL, Zhang XM, Liu JS, Wang H. The antitumoral effect of Paris saponin I associated with the induction of apoptosis through the mitochondrial pathway. Mol Cancer Ther 2009; 8: 1179-1188
3 Ma DD, Lu HX, Xu LS, Xiao W. Polyphyllin D exerts potent anti-tumour effects on Lewis cancer cells under hypoxic conditions. J Intern Med Res 2009; 37: 631-640
4 Zhang XF, Cui Y, Huang JJ, Zhang YZ, Nie Z, Wang LF, Yan BZ, Tang YL, Liu Y. Immuno-stimulating properties of diosgenyl saponins isolated from Paris polyphylla . Bioorg Med Chem Lett 2007; 17: 2408-2413
5 Zhao Y, Kang LP, Liu YX, Liang YG, Tan DW, Yu ZY, Cong YW, Ma BP. Steroidal saponins from the rhizome of Paris polyphylla and their cytotoxic activities. Planta Med 2009; 75: 356-363
6 Xiao CM, Huang J, Zhong XM, Tan XY, Deng PC. Two new homo-aro-cholestane glycosides and a new cholestane glycoside from the roots and rhizomes of Paris polyphylla var. pseudothibetica . Helv Chim Acta 2009; 92: 2587-2595
7 Zhang T, Liu H, Liu XT, Chen XQ, Wang Q. Steroidal saponins from the rhizomes of Paris delavayi . Steroids 2009; 74: 809-813
8 Zhao Y, Kang LP, Liu YX, Zhao Y, Xiong CQ, Ma BP, Dong FT. Three new steroidal saponins from the rhizome of Paris polyphylla . Magn Reson Chem 2007; 45: 739-744
9 Liu H, Huang Y, Wang Q, Zhang T, Song Y. Detection of saponins in extracts from the rhizomes of Paris species and prepared Chinese medicines by high performance liquid chromatography-electrospray ionization mass spectrometry. Planta Med 2006; 72: 835-841
10 Wu SS, Gao WY, Duan HQ, Jia W. Advances in studies on chemical constituents and pharmacological activities of Rhizoma Paridis. Chin Tradit Herb Drugs 2004; 35: 344-347
11 Bureau of Chinese Herb administration. Chinese herbal medicines. Shanghai: Shanghai Sci & Tech Pub. Co.; 1999: 130
12 Zhu LC, Tan J, Wang BC, Guan LH, Liu YP, Zheng C. In-vitro antitumor activity and antifungal activity of pennogenin steroidal saponins from Paris polyphylla var. yunnanensis . Iran J Pharm Res 2011; 10: 279-286
13 Chan JY, Koon JC, Liu XZ, Detmar M, Yu B, Kong SK, Fung KP. Polyphyllin D, a steroidal saponin from Paris polyphylla, inhibits endothelial cell functions in vitro and angiogenesis in zebrafish embryos in vivo . J Ethnopharmacol 2011; 137: 64-69
14 Yan LL, Zhang YJ, Gao WY, Man SL, Wang Y. In vitro and in vivo anticancer activity of steroid saponins of Paris polyphylla var. yunnanensis . Exp Oncol 2009; 31: 27-32
15 Deng DW, Lauren DR, Cooney JM, Jensen DJ, Wurms KV, Upritchard JE, Cannon RD, Wang MZ, Li MZ. Antifungal saponins from Paris polyphylla Smith. Planta Med 2008; 74: 1397-1402
16 Yu MC, Yuan JM. Epidemiology of nasopharyngeal carcinoma. Semin Cancer Biol 2002; 12: 421-429
17 Parkin DM. The global health burden of infection-associated cancers in the year 2002. Int J Cancer 2006; 118: 3030-3044
18 Wang X, Chow LS, Nicholls JM, Kwong DL, Sham JS, Wong YC, Tsao SW. Significance of scheduling on the cytotoxicity of radiation and cisplatin combination treatment in nasopharyngeal carcinoma cells. Anticancer Drugs 2002; 13: 957-964
19 Wang Y, He QY, Tsao SW, Cheung YH, Wong A, Chiu JF. Cytokeratin 8 silencing in human nasopharyngeal carcinoma cells leads to cisplatin sensitization. Cancer Lett 2008; 265: 188-196
20 Xie SM, Fang WY, Liu Z, Wang SX, Li X, Liu TF, Xie WB, Yao KT. Lentivirus-mediated RNAi silencing targeting ABCC2 increasing the sensitivity of a human nasopharyngeal carcinoma cell line against cisplatin. J Transl Med 2008; 6: 55
21 Wu X, Li YL, Zhang DM, Ye WC. In vitro antiproliferative activity of 25 Chinese medicinal herbs against nasopharyngeal carcinoma cell. Chin Tradit Patent Med 2010; 32: 2161-2163
22 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63
23 Yang SL, Liu XK, Wu H, Wang HB, Qing C. Steroidal saponins and cytoxicity of the wild edible vegetable Smilacina atropurpurea . Steroids 2009; 74: 7-12
24 Takechi M, Shimada S, Tanaka Y. Structure-activity relationships of synthetic disogenyl diglycosides. Phytochemistry 1992; 31: 3280-3281
25 Hu WY, Duan JA, Qian DW, Wang DW. Studies on chemical constituents in fresh fleshy scaleleaf of Lilium lancifolium . Chin J Chin Mater Med 2007; 32: 1656-1659
26 Yu H, Han XW, Liu XM, Yu B, Hui YZ, Bao X. NMR studies on synthesized diosgenyl saponin analogs. Magn Reson Chem 2000; 38: 704-706
27 Liu H, Huang Y, Zhang T, Wang Q, Chen XQ. Studies on chemical constituents of Paris delavayi Franch. J China Pharm Univ 2006; 37: 409-412
28 Ono M, Takamura C, Sugita F, Masuoka C, Yoshimitsu H, Ikeda T, Nohara T. Two new steroid glycosides and a new sesquiterpenoid glycoside from the underground parts of Trillium kamtschaticum . Chem Pharm Bull 2007; 55: 551-556
29 Chen CX, Zhang YT, Zhou J. Studies on the saponin components of plants in Yunnan VI. Steroid glycosides of Paris polyphylla sm. var. yunnanensis (Fr.) H–M (2). Acta Bot Yunn 1983; 5: 91-97
30 Chen CX, Zhou J. Studies on the saponin components of plants in Yunnan VIII. Steroidal saponins in Paris luquanensis . Acta Bot Yunn 1983; 5: 219-223
31 Liu DL, Pang FG, Zhang JX, Wang NL, Yao XS. Studies on the chemical constituents of Bulbophyllum odoratissimum Lindi. Chin J Med Chem 2005; 15: 103-107
32 Zheng GM, Wei XY, Xu LX, Xie HH, Wu P. Chemical constituents from pericarp of longan fruits. Chin Tradit Herb Drugs 2011; 42: 1485-1489
33 Suksamrarn A, Kumpun S, Yingyongnarongkul B. Ecdysteroids of Vitex scabra stem bark. J Nat Prod 2002; 65: 1690-1692
34 Odinokov VN, Galyautdinov IV, Ibragimova AS, Veskina NA, Khalilov LM, Dolgushin FM, Starikova ZA. Novel ecdysteroid analogs with oxygen-containing heterocycles in the steroid skeleton. Chem Heterocycl Compds 2008; 44: 1077-1091
35 Gunatilaka AAL, Gopichand Y, Schmitz FJ, Djerassi C. Minor and trace sterols in marine invertebrates. 26. Isolation and structure elucidation of nine new 5α,8α-epidoxy sterols from four marine organisms. J Org Chem 1981; 46: 3860-3866
36 Takaishi Y, Uda M, Ohashi T, Nakano K, Murakami K, Tomimatsu T. Glycosides of ergosterol derivatives from Hericum erinacens . Phytochemistry 1991; 30: 4117-4120
37 Zhang DM, Miyase T, Kuroyanagi M, Umehara K, Ueno A. Studies on the constituents of Polygala japonica Houtt. I. Structures of polygalasaponins I–X. Chem Pharm Bull 1995; 43: 115-120
38 Idaka K, Hirai Y, Shoji J. Studies on the constituents of Palmae plants. V. Steroid saponins and flavonoids of leaves of Phoenix rupicola T. Anderson, P. loureirii kunth, P. reclinata N. J. Jacquin, and Arecastrum romanzoffianum beccari. Chem Pharm Bull 1991; 39: 1455-1461
39 Yan LL, Zhang YJ, Gao WY, Man SL. Study on structure-function relationship and cytotoxic activities of steroid saponins of Paris polyphylla var. yunnanensis on 10 tumor cells. Chin J Chin Mater Med 2008; 33: 2057-2060

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