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

Uri Zehavi*, Orit Ziv-Fecht, Mordekhai Levy, Michael Naim, Ruth Evron, Itzhack Polacheck

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

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 23α-hydroxymethyl analog of medicagenic acid, namely, methyl 2β,3β-dihydroxy-23α-hydroxymethyl-Δ12-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.

Original languageEnglish
Pages (from-to)161-169
Number of pages9
JournalCarbohydrate Research
Volume244
Issue number1
DOIs
StatePublished - 21 May 1993

Fingerprint

Dive into the research topics of 'Synthesis and antifungal activity of medicagenic acid saponins on plant pathogens: modification of the saccharide moiety and the 23α substitution'. Together they form a unique fingerprint.

Cite this