TY - JOUR
T1 - Synthesis and antifungal activity of medicagenic acid saponins on plant pathogens
T2 - modification of the saccharide moiety and the 23α substitution
AU - Zehavi, Uri
AU - Ziv-Fecht, Orit
AU - Levy, Mordekhai
AU - Naim, Michael
AU - Evron, Ruth
AU - Polacheck, Itzhack
PY - 1993/5/21
Y1 - 1993/5/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0027590950&partnerID=8YFLogxK
U2 - 10.1016/0008-6215(93)80012-4
DO - 10.1016/0008-6215(93)80012-4
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C2 - 8339299
AN - SCOPUS:0027590950
SN - 0008-6215
VL - 244
SP - 161
EP - 169
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1
ER -