Abstract

Phytochemical investigation on the whole plants of Ypsilandra yunnanensis was carried out for the first time and led to the isolation of five new cholestanol glycosides, ypsiyunnosides A–E (1–5), and one known analogue. Their structures were determined mainly by detailed spectroscopic analysis, including extensive 1D and 2D NMR, MS and UV, as well as chemical methods. Among them, compound 1 possessed a rare 6/6/6/5/5 fused-rings cholestanol sketelon, which was identified as (23R,25R)-3β,16α,26-triol-16,23-cyclocholest-5,17(20)-dien-22-one. Their induced platelet aggregation activities and cytotoxicities were evaluated.Graphical Five new cholestanol glycosides, ypsiyunnosides A–E (1–5), were isolated from the whole plants of Ypsilandra yunnanensis. Compound 1 possessed a rare 6/6/6/5/5 fused-rings cholestanol sketelon. Their structures were elucidated by a combination of 1D and 2D NMR, MS and chemical analysis. Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0098-2) contains supplementary material, which is available to authorized users.

Highlights

  • The HPLC analysis revealed that the secondary metabolites of Y. thibetica and Y. yunnanensis were very different, especially in the water-soluble part of the crude extract

  • The result led to the isolation of five new cholestane glycosides (1–5) and one known analogue, parispseudoside C (6) [10] as shown in Fig. 1 from the 70 % EtOH extract of the whole title plant

  • Their structures were determined by the analysis of spectroscopic data (HR-ESI-MS, 1D and 2D NMR) and chemical methods

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Summary

Graphical Abstract

Ypsiyunnosides A–E (1–5), were isolated from the whole plants of Ypsilandra yunnanensis. Compound 1 possessed a rare 6/6/6/5/5 fused-rings cholestanol sketelon. Their structures were elucidated by a combination of 1D and 2D NMR, MS and chemical analysis. Keywords Ypsilandra yunnanensis Á Liliaceae Á Cholestane glycoside Á Ypsiyunnosides A–E. Yu Chen and Yong-Ai Si have contributed to this work. Electronic supplementary material The online version of this article (doi:10.1007/s13659-016-0098-2) contains supplementary material, which is available to authorized users. Si University of Chinese Academy of Sciences, Beijing 100039, China

Introduction
Results and Discussion
Plant Material
Extraction and Isolation
Acid Hydrolysis and GC Analysis
3.10 Cytotoxic Assay
Platelet Aggregation Assays

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