Synthesis and antifungal activity of medicagenic acid saponins on plant pathogens: modification of the saccharide moiety and the 23 alpha 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 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.
Zehavi
U
U
Department of Biochemistry and Human Nutrition, Faculty of Agriculture, Hebrew University of Jerusalem, Rehovot, Israel.
Ziv-Fecht
O
O
Levy
M
M
Naim
M
M
Evron
R
R
Polacheck
I
I
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001234:Aspergillus niger / Q000187:drug effects; D002240:Carbohydrate Sequence; D005658:Fungi / Q000187:drug effects*; D005670:Fusarium / Q000187:drug effects; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D010944:Plants / Q000382:microbiology; D012232:Rhizoctonia / Q000187:drug effects; D012503:Saponins / Q000138:chemical synthesis* / Q000494:pharmacology; D014242:Trichoderma / Q000187:drug effects; D014315:Triterpenes / Q000494:pharmacology*
D000935:Antifungal Agents; D006027:Glycosides; D009844:Oligosaccharides; D012503:Saponins; D014315:Triterpenes; C005982:medicagenic acid