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Ypsiyunnosides A – E, Five New Cholestanol Glycosides from Ypsilandra yunnanensis

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ABSTRACT

151: 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 (–), 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 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.

151: Five new cholestanol glycosides, ypsiyunnosides A–E (–), were isolated from the whole plants of Ypsilandrayunnanensis. Compound 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 material: The online version of this article (doi:10.1007/s13659-016-0098-2) contains supplementary material, which is available to authorized users.

No MeSH data available.


Chemical structures of compounds 1–5
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Fig1: Chemical structures of compounds 1–5

Mentions: Ypsilandra yunnanensis W. W. Sm. et J. F. Jeffr., belonging to the family of Liliaceae, is an erect, perennial herb and distributed mainly in the northwest of Yunnan Province and the southeast of the Tibet Autonomous Region of China. It usually grows in grass slope, forest-shrub edge, or under the bushes at the altitude between 3300 and 4000 m [1]. Previously, we have performed a systemic phytochemical investigation of the whole plants of Y. thibetica and obtained a series of spirostanol-, furostanol-, and 23-spirocholestanol glycosides with cytotoxic, antifungal, hemostatic, and anti-HIV activities [2–9]. However, the phytochemicals and the biological activity of Y. yunnanensis have not been reported so far. 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. As part of our continuing search for structurally diverse and bioactive steroidal glycosides from the Ypsilandra plants, the chemical constituents of Y. yunnanensis were investigated. 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. This paper presents herein the isolation, structural elucidation, and the induced platelet aggregation activities and cytotoxicities of these compounds.Fig. 1


Ypsiyunnosides A – E, Five New Cholestanol Glycosides from Ypsilandra yunnanensis
Chemical structures of compounds 1–5
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5385661&req=5

Fig1: Chemical structures of compounds 1–5
Mentions: Ypsilandra yunnanensis W. W. Sm. et J. F. Jeffr., belonging to the family of Liliaceae, is an erect, perennial herb and distributed mainly in the northwest of Yunnan Province and the southeast of the Tibet Autonomous Region of China. It usually grows in grass slope, forest-shrub edge, or under the bushes at the altitude between 3300 and 4000 m [1]. Previously, we have performed a systemic phytochemical investigation of the whole plants of Y. thibetica and obtained a series of spirostanol-, furostanol-, and 23-spirocholestanol glycosides with cytotoxic, antifungal, hemostatic, and anti-HIV activities [2–9]. However, the phytochemicals and the biological activity of Y. yunnanensis have not been reported so far. 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. As part of our continuing search for structurally diverse and bioactive steroidal glycosides from the Ypsilandra plants, the chemical constituents of Y. yunnanensis were investigated. 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. This paper presents herein the isolation, structural elucidation, and the induced platelet aggregation activities and cytotoxicities of these compounds.Fig. 1

View Article: PubMed Central - PubMed

ABSTRACT

151: 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 (–), 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 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.

151: Five new cholestanol glycosides, ypsiyunnosides A–E (–), were isolated from the whole plants of Ypsilandrayunnanensis. Compound 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 material: The online version of this article (doi:10.1007/s13659-016-0098-2) contains supplementary material, which is available to authorized users.

No MeSH data available.