Abstract
A new spirostanol saponin, together with three known saponins, were isolated from the leaves of Solanum hispidum. The structure of the new saponin was elucidated as 6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta-ol (1) on the basis of spectroscopic analysis (1H NMR, 13C NMR, 1H-1H COSY, HMQC, HMBC, and HRFABMS). All of the isolated compounds showed antimycotic activity. The most active compound was 6alpha-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-quinovopyranosyl]-(25S)-5alpha-spirostan-3beta-ol (2) (MIC = 25 microg/mL against both Trichophyton mentagrophytes and T. rubrum). The structure-activity relationships of the isolated compounds and those isolated from S. chrysotrichum are discussed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antifungal Agents / chemistry
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Antifungal Agents / isolation & purification*
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Antifungal Agents / pharmacology
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Mexico
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Plant Leaves / chemistry
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Plants, Medicinal / chemistry*
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Saponins / chemistry
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Saponins / isolation & purification*
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Saponins / pharmacology
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Solanum / chemistry*
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Spirostans / chemistry
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Spirostans / isolation & purification*
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Spirostans / pharmacology
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Stereoisomerism
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Structure-Activity Relationship
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Trichophyton / drug effects*
Substances
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6alpha-O-(beta-D-xylopyranosyl-(1-3)-beta-D-quinovopyranosyl)-(25S)-5alpha-spirostan-3beta-ol
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6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta-ol
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Antifungal Agents
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Saponins
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Spirostans