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

✍ Scribed by Uri Zehavi; Orit Ziv-Fecht; Mordekhai Levy; Michael Naim; Ruth Evron; Itzhack Polacheck

Book ID
102990316
Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
625 KB
Volume
244
Category
Article
ISSN
0008-6215

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✦ Synopsis

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 23a-hydroxymethyl analog of medicagenic acid, namely, methyl 2B,3&dihydroxy-23n-hydroxymethyl-A'*-oleanene-28@zarboxylate, against Sclerotium roljkii, 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 23a 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.

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