Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships.
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.
González
Manases
M
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, 62210 Cuernavaca, Morelos, México.
Zamilpa
Alejandro
A
Marquina
Silvia
S
Navarro
Víctor
V
Alvarez
Laura
L
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008800:Mexico; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D032322:Solanum / Q000737:chemistry*; D013150:Spirostans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014249:Trichophyton / Q000187:drug effects*
C487914:6alpha-O-(beta-D-xylopyranosyl-(1-3)-beta-D-quinovopyranosyl)-(25S)-5alpha-spirostan-3beta-ol; C487913:6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta-ol; D000935:Antifungal Agents; D012503:Saponins; D013150:Spirostans