Natural Zinniol Derivatives from Alternaria tagetica. Isolation, Synthesis, and Structure-Activity Correlation

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• 作者：M. Marcela Gamboa-Angulo ; Fabiola Escalante-Erosa ; Karlina Garc&iacute ; a-Sosa ; Fá ; tima Alejos-Gonzá ; lez ; Guillermo Delgado-Lamas ; and Luis M. Peñ ; a-Rodr&iacute ; guez
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2002
• 出版时间：February 27, 2002
• 年：2002
• 卷：50
• 期：5
• 页码：1053 - 1058
• 全文大小：79K
• 年卷期：v.50,no.5(February 27, 2002)
• ISSN：1520-5118

文摘

Two novel phytotoxins, 8-zinniol methyl ether (5) and 8-zinniol acetate (6), in addition to 6-(3',3'-dimethylallyloxy)-4-methoxy-5-methylphthalide (2), 5-(3',3'-dimethylallyloxy)-7-methoxy-6-methylphthalide (3), and the novel metabolites 8-zinniol 2-(phenyl)ethyl ether (4) and 7-zinniol acetate (7) havebeen identified as natural zinniol derivatives from the organic crude extract of Alternaria tageticaculture filtrates. Using zinniol as the starting material, phytotoxin 5 was synthesized, together with anumber of synthetic intermediates (8-13). Both natural and synthetic zinniol derivatives were evaluatedin the leaf-spot bioassay against marigold leaves (Tagetes erecta).Keywords: Alternaria tagetica; Tagetes erecta; marigold; phytotoxin; zinniol; zinniol derivatives; leaf-spot bioassay