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Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships.
J Nat Prod. 2004 Jun; 67(6):938-41.JN

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.

Authors+Show Affiliations

González M
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Chamilpa, 62210 Cuernavaca, Morelos, México.
Zamilpa A
No affiliation info available
Marquina S
No affiliation info available
Navarro V
No affiliation info available
Alvarez L
No affiliation info available

MeSH

Antifungal AgentsMexicoMolecular StructureNuclear Magnetic Resonance, BiomolecularPlant LeavesPlants, MedicinalSaponinsSolanumSpirostansStereoisomerismStructure-Activity RelationshipTrichophyton

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15217270

Citation

González, Manases, et al. "Antimycotic Spirostanol Saponins From Solanum Hispidum Leaves and Their Structure-activity Relationships." Journal of Natural Products, vol. 67, no. 6, 2004, pp. 938-41.
González M, Zamilpa A, Marquina S, et al. Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships. J Nat Prod. 2004;67(6):938-41.
González, M., Zamilpa, A., Marquina, S., Navarro, V., & Alvarez, L. (2004). Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships. Journal of Natural Products, 67(6), 938-41.
González M, et al. Antimycotic Spirostanol Saponins From Solanum Hispidum Leaves and Their Structure-activity Relationships. J Nat Prod. 2004;67(6):938-41. PubMed PMID: 15217270.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships. AU - González,Manases, AU - Zamilpa,Alejandro, AU - Marquina,Silvia, AU - Navarro,Víctor, AU - Alvarez,Laura, PY - 2004/6/26/pubmed PY - 2004/8/10/medline PY - 2004/6/26/entrez SP - 938 EP - 41 JF - Journal of natural products JO - J Nat Prod VL - 67 IS - 6 N2 - 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. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/15217270/Antimycotic_spirostanol_saponins_from_Solanum_hispidum_leaves_and_their_structure_activity_relationships_ DB - PRIME DP - Unbound Medicine ER -