A Two-Dimensional NMR Study on Steroid Glycosides Extracted from Trillium tschonoskii

doi:10.11938/cjmr20150112

Chinese Journal of Magnetic Resonance ›› 2015, Vol. 32 ›› Issue (1): 105-115.doi: 10.11938/cjmr20150112

A Two-Dimensional NMR Study on Steroid Glycosides Extracted from Trillium tschonoskii

CHAI Jiang1，WANG Xin3，LI Hui-min4，ZHANG Xin1，YANG Fang1，TANG Zhi-shu1，SONG Xiao-mei1，PEI Yue-hu4，MEI Qi-bing2，YUE Zheng-gang1,2?

1. Shaanxi Collaborative Innovation Center of Chinese Medicinal Resource Industrialization, Shannxi Province Key Laboratory of New Drugs and Chinese Medicine Foundation Research, Shaanxi Rheumatism and Tumor Center of TCM Engineering Technology Research, School of Pharmacy, Shannxi University of Traditional Chinese Medicine, Xianyang 712046, China;
2. Key Laboratory of Gastrointestinal Pharmacology of Chinese Materia Medica of the State Administration of Traditional Chinese Medicine, Collaborative Innovation Center for Chinese Medicine in Qinba Mountains, School of Pharmacy, the Fourth Military Medical University, Xi′an 710032, China;
3. The First Hospital of Xi′an, Xi′an 710002, China;
4. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China

Received:2014-05-26 Revised:2015-01-12 Online:2015-03-05 Published:2015-03-05
About author:*Corresponding author：YUE Zheng-gang, Tel: +86-18092086211, E-mail: liuxingjian1981@163.com.
Supported by:
国家自然科学基金资助项目(81373978)；陕西省重点科技创新团队资助项目(2012KCT-20)；陕西省“13115”科技创新工程专项资助项目(2010ZDGC-22)；陕西省教育厅科技计划资助项目(09jk394)．

Abstract

Abstract:

(25S)-27-hydroxypenogenin-3β-O-α-L-rhamnopyranosyl-(1→4)-[O-α-L-rhamnopyranosyl-(1→2)]-O-β-D-glucopyranoside (1) and polyphylloside III (2) were isolated from Trillium tschonoskii by column chromatography. One-dimensional and two-dimensional NMR techniques, including ¹H NMR, ¹³C NMR, DEPT, HSQC, HMBC and ¹H-¹H COSY, were used to elucidate the structures of these compounds. ¹³C NMR and ¹H NMR chemical shifts of the two compounds were completely assigned.

Key words: NMR, two-dimensional NMR, steroid glycosides, assignment

CLC Number:

O482.53

CHAI Jiang1，WANG Xin3，LI Hui-min4，ZHANG Xin1，YANG Fang1，TANG Zhi-shu1，SONG Xiao-mei1，PEI Yue-hu4，MEI Qi-bing2，YUE Zheng-gang1,2. A Two-Dimensional NMR Study on Steroid Glycosides Extracted from Trillium tschonoskii[J]. Chinese Journal of Magnetic Resonance, 2015, 32(1): 105-115.

References

[1] Xie Zong-wan(谢宗万). The Compilation of Chinese Herbal Medicine(全国中草药汇编): 上册(第2 版)[M]. Beijing (北京): People's Medical Publishing House(人民卫生出版社), 2000.

[2] Song Xiao-mei(宋小妹), Liu Hai-jing(刘海静). Research and Application of "Qi-Medicines" in Taibai Mountains(太白七药研究与应用)[M]. Beijing(北京): People's Medical Publishing House(人民卫生出版社), 2011.

[3] Yu Ling-ling(喻玲玲), Zou Kun(邹坤), Wang Xi-zhi(汪鋆植), et al. Study on the anti- inflammatory, analgesic and thrombosis effects of extract of Trillium tschonoskii Maxim. (延龄草提取物抗炎、镇痛和凝血作用的研究)[J]. Lishizhen Medicine and Materia Medica Research(时珍国医国药), 2008, 19(5) : 1 178－1 180.

[4] Li Y H, Sun Y, Fan L, et al. Paris saponin VII inhibits growth of colorectal cancer cells through Ras signaling pathway[J]. Biochem Pharmacol, 2014, 88(2): 150－157.

[5] Wang H, Zhai Z B, Li N L, et al. Steroidal saponin of Trillium tschonoskii. Reverses multidrug resistance of hepatocellular carcinoma[J]. Phytomedicine, 2013, 20(11): 985－991.

[6] Masateru O, TAKAMURA C, SUGITA F, et al. Two new steroid glycosides and a new sesquiterpenoid glycoside from the underground parts of Trillium kamtschaticum[J]. Chem Pharm Bull, 2007, 55(4): 551－556.

[7] Masateru O, Fumie S, Syoko S, et al. Three new steroid glycosides from the underground parts of Trillium kamtschaticum[J]. Chem Pharm Bull, 2007, 55(7): 1 093－1 096.

[8] Nakano K, Maruashi T, Nohara T, et al. A flavonol glycoside and a sesquiterpene cellobioside from Trillium tschonoskii[J]. Phytochemistry, 1983, 22(5): 1 249－1 251.

[9] Huang H C, Tsai W J, Liaw C C, et al. Anti-platelet aggregation triterpene saponins from the galls of Sapindus mukorossi [J]. Chem Pharm Bull, 2007, 55(9): 1 412－1 415.

[10] Li Hui-min(李慧敏), Pan Xian-wei(潘宪伟), Mei Qi-bing(梅其炳), et al. Isolation and identification of chemical constituents from root and rhizoma of Trillium tschonoskii Maxim.(延龄草化学成分的分离与鉴定)[J]. Journal of Shenyang Pharmaceutical University(沈阳药科大学学报), 2013, 30(7): 509－516.

[11] Ju Y, Jia Z J. Steroidal saponins from the rhizomes Smilax menispermoidea[J]. Phytochemistry, 1992, 31(4): 1 349－1 351.

[12] Chen Chang-xiang(陈昌祥), Zhou Jun(周俊), Hiromichi Nagasawa, et al. Two minor steroidal saponins from the aerial parts of paris polyhylla var. Yunnanensis(滇重楼地上部分的两个微量皂甙)[J]. Acta Botanica Yannanico(云南植物研究), 1995, 17(2): 215－220.

[13] Huang H C, Lin M K, Hwang S Y, et al. Two anti-inflammatory steroidal saponins from Dracaena angustifolia Roxb[J]. Molecules, 2013, 18(8): 8 752－8 763.

[14] Kang Li-ping(康利平), Wang Yong-ze(王永泽), Feng Bing(冯冰), et al. An NMR study on two glucosylated steroidal saponins of Tb 2(皂苷Tb 2个糖基化产物的NMR研究)[J]. Chinese J Magn Reson(波谱学杂志), 2012, 29(1): 101－111.

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A Two-Dimensional NMR Study on Steroid Glycosides Extracted from Trillium tschonoskii

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