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 |
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| container_title | Carbohydrate research |
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| creator | Zehavi, Uri Ziv-Fecht, Orit Levy, Mordekhai Naim, Michael Evron, Ruth Polacheck, Itzhack |
| description | 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. |
| doi_str_mv | 10.1016/0008-6215(93)80012-4 |
| format | Article |
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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
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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. 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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.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>8339299</pmid><doi>10.1016/0008-6215(93)80012-4</doi><tpages>9</tpages></addata></record> |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Antifungal Agents - chemical synthesis Antifungal Agents - pharmacology Aspergillus niger - drug effects Carbohydrate Sequence Chemistry Exact sciences and technology Fungi - drug effects Fusarium - drug effects Glycosides - chemical synthesis Glycosides - pharmacology Molecular Sequence Data Oligosaccharides - chemical synthesis Oligosaccharides - pharmacology Organic chemistry Plants - microbiology Preparations and properties Rhizoctonia - drug effects Saponins - chemical synthesis Saponins - pharmacology Terpenoids Trichoderma - drug effects Triterpenes - pharmacology |
| title | Synthesis and antifungal activity of medicagenic acid saponins on plant pathogens: modification of the saccharide moiety and the 23α substitution |
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