Synthesis and antifungal activity of medicagenic acid saponins on plant pathogens: modification of the saccharide moiety and the 23α substitution

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 23α-hydroxymethyl analog of medicagenic acid, namely, methyl 2β,3β-dihydroxy-23α-hydroxymethyl-Δ 12-oleanene-2...

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Veröffentlicht in:Carbohydrate research 1993-05, Vol.244 (1), p.161-169
Hauptverfasser: Zehavi, Uri, Ziv-Fecht, Orit, Levy, Mordekhai, Naim, Michael, Evron, Ruth, Polacheck, Itzhack
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Sprache:eng
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Zusammenfassung: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 23α-hydroxymethyl analog of medicagenic acid, namely, methyl 2β,3β-dihydroxy-23α-hydroxymethyl-Δ 12-oleanene-28β-carboxylate, against Sclerothium 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 23α 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.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(93)80012-4