Ypsilandrosides U-Y, five new steroidal saponins from Ypsilandra thibetica

doi:10.1007/s13659-022-00337-0

应用天然产物 ›› 2022, Vol. 12 ›› Issue (3): 17-17.DOI: 10.1007/s13659-022-00337-0

Ypsilandrosides U-Y, five new steroidal saponins from Ypsilandra thibetica

Wen-Tao Gao^1,2, Ling-Ling Yu^2,3, Jing Xie^2,3, Long-Gao Xiao^2,3, Shi-Juan Zhang^2,3, Wen-Yi Ma^2,3, Huan Yan², Hai-Yang Liu²

1 College of Traditional Chinese Medicine, Yunnan University of Chinese Medicine, Kunming, 650500, China;
2 State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China;
3 University of Chinese Academy of Sciences, Beijing, 100049, China

收稿日期:2022-02-21 出版日期:2022-06-24 发布日期:2022-06-24
通讯作者: Hai-Yang Liu,E-mail:haiyangliu@mail.kib.ac.cn
基金资助:
This work was financially supported by the National Natural Science Foundation of China (U1802287 and 32000280), the Ten Thousand Talents Plan of Yunnan Province for Industrial Technology Leading Talents, and the State Key Laboratory of Phytochemistry and Plant Resources in West China (P2019-ZZ02).

Ypsilandrosides U-Y, five new steroidal saponins from Ypsilandra thibetica

Wen-Tao Gao^1,2, Ling-Ling Yu^2,3, Jing Xie^2,3, Long-Gao Xiao^2,3, Shi-Juan Zhang^2,3, Wen-Yi Ma^2,3, Huan Yan², Hai-Yang Liu²

1 College of Traditional Chinese Medicine, Yunnan University of Chinese Medicine, Kunming, 650500, China;
2 State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China;
3 University of Chinese Academy of Sciences, Beijing, 100049, China

Received:2022-02-21 Online:2022-06-24 Published:2022-06-24
Contact: Hai-Yang Liu,E-mail:haiyangliu@mail.kib.ac.cn
Supported by:
This work was financially supported by the National Natural Science Foundation of China (U1802287 and 32000280), the Ten Thousand Talents Plan of Yunnan Province for Industrial Technology Leading Talents, and the State Key Laboratory of Phytochemistry and Plant Resources in West China (P2019-ZZ02).

摘要/Abstract

摘要： Phytochemical reinvestigation on the whole plants of Ypsilandra thibetica obtained four new spirostanol glycosides, named ypsilandrosides U-X (1–4), and one new cholestanol glycoside, named ypsilandroside Y (5). Their structures have been established by extensive spectroscopic data and chemical methods. Among them, compound 4 is a rare spirostanol glycoside which possesses a novel 5(6 → 7) abeo-steroidal aglycone, while compound 1 is a first spirostanol bisdesmoside attached to C-3 and C-12, respectively, isolated from the genus Ypsilandra. The induced platelet aggregation activity of the isolates was tested.

关键词: Ypsilandra thibetica, Melanthiaceae, Ypsilandrosides U-Y, Spirostanol saponins, Cholestanol saponins

Abstract: Phytochemical reinvestigation on the whole plants of Ypsilandra thibetica obtained four new spirostanol glycosides, named ypsilandrosides U-X (1–4), and one new cholestanol glycoside, named ypsilandroside Y (5). Their structures have been established by extensive spectroscopic data and chemical methods. Among them, compound 4 is a rare spirostanol glycoside which possesses a novel 5(6 → 7) abeo-steroidal aglycone, while compound 1 is a first spirostanol bisdesmoside attached to C-3 and C-12, respectively, isolated from the genus Ypsilandra. The induced platelet aggregation activity of the isolates was tested.

Key words: Ypsilandra thibetica, Melanthiaceae, Ypsilandrosides U-Y, Spirostanol saponins, Cholestanol saponins

Wen-Tao Gao, Ling-Ling Yu, Jing Xie, Long-Gao Xiao, Shi-Juan Zhang, Wen-Yi Ma, Huan Yan, Hai-Yang Liu. Ypsilandrosides U-Y, five new steroidal saponins from Ypsilandra thibetica[J]. 应用天然产物, 2022, 12(3): 17-17.

参考文献

1.Li D-Z.The families and genera of Chinese vascular plants, vol.1.Beijing:China Science Press; 2020.p.354-5.
2.College JNM.Dictionary of traditional Chinese materia medica.Shanghai:China Shanghai Scientifc and Technological Press; 1977.p.1841.
3.Yunnan Food and Drug Administration.The Yunnan Chinese materia medica standards, Yi Nationality Medicine (III), Kunming:China Shanghai Yunnan Scientifc and Technological Press; 2005.p.5-6.
4.Xie B-B, Liu H-Y, Ni W, Chen C-X.Ypsilandrosides C-G, fve new spirostanol saponins from Ypsilandra thibetica.Steroids.2009;74:950-5.
5.Liu H-Y, Chen C-X, Lu Y, Yang J-Y, Ni W.Steroidal and pregnane glycosides from Ypsilandra thibetica.Nat Prod Bioprospect.2012;2:11-5.
6.Xie B-B, Liu H-Y, Ni W, Chen C-X, Lu Y, Wu L, Zheng Q-T.Five new steroidal compounds from Ypsilandra thibetica.Chem Biodivers.2006;3:1211-8.
7.Xie B-B, Chen C-X, Guo Y-H, Li Y-Y, Liu Y-J, Ni W, Yang L-M, Gong N-B, Zheng Y-T, Wang R-R, Lu Y, Liu H-Y.New 23-spirocholestane derivatives from Ypsilandra thibetica.Planta Med.2013;79:1063-7.
8.Lu Y, Xie B-B, Chen C-X, Ni W, Hua Y, Liu H-Y.Ypsilactosides A and B, two new C22-steroidal lactone glycosides from Ypsilandra thibetica.Helv Chim Acta.2011;94:92-7.
9.Si Y-A, Yan H, Ni W, Liu Z-H, Lu T-X, Chen C-X, Liu H-Y.Two new steroidal saponins from Ypsilandra thibetica.Nat Prod Bioprospect.2014;4:315-8.
10.Lu Y, Chen C-X, Ni W, Hua Y, Liu H-Y.Spirostanol tetraglycosides from Ypsilandra thibetica.Steroids.2010;75:982-7.
11.Nakano K, Murakami K, Takaishi Y, Tomimatsu T, Nohara T.Studies on the constituents of Heloniopsis orientalis (Thunb.) C.Tanaka.Chem Pharm Bull.1989;37:116-8.
12.Snyder J-R, Serianni A-S.DL-Apiose substituted with stable isotpoes-synthesis, NMR-spectral analysis, and furanose anomerization.Carbohydr Res.1987;166:85-99.
13.Kitagawa I, Sakagami M, Hashiuchi F, Zhou J-L, Yoshikawa M, Ren J.Apioglycyrrhizin and araboglycyrrhizin, 2 new sweet oleanene-type trit-erpene oligoglycosides from the root of Glycyrrhiza infata.Chem Pharm Bull.1989;37:551-3.
14.Agrawal P-K.NMR-spectroscopy in the structural elucidation of oligosac-charides and glycosides.Phytochemistry.1992;31:3307-30.
15.Kasai M-O-R, Asakawa J, Mizutani K, Tanaka O.¹³C NMR study of α-and β-anomeric pairs of D-mannopyranosides and L-rhamnopyranosides.Tetrahedron.1979;35:1427-32.
16.Lu T-X, Shu T, Qin X-J, Ni W, Ji Y-H, Chen Q-R, Khanf A, Zhao Q, Liu H-Y.Spi-rostanol saponins from Ypsilandra parvifora induce platelet aggregation.Steroids.2017;123:55-60.
17.Yang Y-J, Pang X, Wang B, Yang J, Chen X-J, Sun X-G, Li Q, Zhang J, Guo B-L, Ma B-P.Steroidal saponins from Trillium tschonoskii rhizomes and their cytotoxicity against HepG2 cells.Steroids.2020;156:108587.
18.Xiao C-M, Huang J, Zhong X-M, Tan X-Y, Deng P-C.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;92:2587-95.
19.Born G-V-R.Aggregation of blood platelets by adenosine diphosphate and its reversal.Nature.1962;194:927-9.
20.Born G-V-R, Cross M-J.The aggregation of blood platelets.J Physiol.1963;168:178-95.

[1]	Ling-Yu Jin, Ting-Xiang Lu,. Xu-Jie Qin, Wei Ni, Huan Yan, Yu Chen, Hui Liu, Hong-Ping He, Hai-Yang Liu. Two New Highly Oxygenated Spirostanol Saponins from Paris polyphylla var. stenophylla[J]. 应用天然产物, 2016, 6(4): 205-210.
[2]	Yong-Ai Si, Huan Yan, Wei Ni, Zhen-Hua Liu, Ting-Xiang Lu, Chang-Xiang Cheng, Hai-Yang Liu. Two New Steroidal Saponins from Ypsilandra thibetica[J]. 应用天然产物, 2014, 4(6): 315-318.
[3]	Hai-Yang LIU, Chang-Xiang CHEN, Yi LU, Jun-Yun YANG, Wei NI. Steroidal and pregnane glycosides from Ypsilandra thibetica[J]. 应用天然产物, 2012, 2(1): 11-15.

Ypsilandrosides U-Y, five new steroidal saponins from Ypsilandra thibetica

Ypsilandrosides U-Y, five new steroidal saponins from Ypsilandra thibetica

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 3

编辑推荐

Metrics

本文评价