Natural Products and Bioprospecting    2022, Vol. 12 Issue (3) : 17-17     DOI: 10.1007/s13659-022-00337-0
ORIGINAL ARTICLES |
Ypsilandrosides U-Y, five new steroidal saponins from Ypsilandra thibetica
Wen-Tao Gao1,2, Ling-Ling Yu2,3, Jing Xie2,3, Long-Gao Xiao2,3, Shi-Juan Zhang2,3, Wen-Yi Ma2,3, 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
Download: PDF(1194 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
Abstract  Phytochemical reinvestigation on the whole plants of Ypsilandra thibetica obtained four new spirostanol glycosides, named ypsilandrosides U-X (14), 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.
Keywords Ypsilandra thibetica      Melanthiaceae      Ypsilandrosides U-Y      Spirostanol saponins      Cholestanol saponins     
Fund: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).
Corresponding Authors: Hai-Yang Liu,E-mail:haiyangliu@mail.kib.ac.cn     E-mail: haiyangliu@mail.kib.ac.cn
Issue Date: 24 June 2022
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
Wen-Tao Gao
Ling-Ling Yu
Jing Xie
Long-Gao Xiao
Shi-Juan Zhang
Wen-Yi Ma
Huan Yan
Hai-Yang Liu
Trendmd:   
Cite this article:   
Wen-Tao Gao,Ling-Ling Yu,Jing Xie, et al. Ypsilandrosides U-Y, five new steroidal saponins from Ypsilandra thibetica[J]. Natural Products and Bioprospecting, 2022, 12(3): 17-17.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-022-00337-0     OR     http://npb.kib.ac.cn/EN/Y2022/V12/I3/17
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]. Natural Products and Bioprospecting, 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]. Natural Products and Bioprospecting, 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]. Natural Products and Bioprospecting, 2012, 2(1): 11-15.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed