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Synthesis and Antifungal Activity of Medicagenic Acid Saponins on Plant Pathogens: Modification of the Saccharide Moiety and the 23 Alpha Substitution

Synthesis and Antifungal Activity of Medicagenic Acid Saponins on Plant Pathogens: Modification of the Saccharide Moiety and the 23 Alpha Substitution

U Zehavi, O Ziv-Fecht, M Levy, M Naim, R Evron, I Polacheck

Carbohydr Res. 1993 May 21;244(1):161-9.

PMID: 8339299

Abstract:

The study of structure-antifungal activity relationships of medicagenic acid saponins was widened to include synthetic glycosides of mannose, galactose, cellobiose, and lactose as well as a 23 alpha-hydroxymethyl analog of medicagenic acid, namely, methyl 2 beta,3 beta-dihydroxy-23 alpha-hydroxymethyl-delta (12)-oleanene-28 beta-carboxylate, against Sclerotium rolfsii, Rhizoctonia solani, Trichoderma viride, Aspergillus niger, and Fusarium oxysporum. The native glucose-containing saponin was a more effective antifungal agent than the aforementioned saponins, except in the case of the cellobiose-containing derivative and F. oxysporum. A carboxyl substituent at the 23 alpha position of the sapogenin brought about higher fungistatic activity than a methyl carboxylate which, in turn, was more effective than an hydroxymethyl group at the same position.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP599075	Medicagenic acid		599-07-5	Price

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