Natural zinniol derivatives from Alternaria tagetica. Isolation, synthesis, and structure-activity correlation.
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) have been identified as natural zinniol derivatives from the organic crude extract of Alternaria tagetica culture filtrates. Using zinniol as the starting material, phytotoxin 5 was synthesized, together with a number of synthetic intermediates (8-13). Both natural and synthetic zinniol derivatives were evaluated in the leaf-spot bioassay against marigold leaves (Tagetes erecta).
Gamboa-Angulo
M Marcela
MM
Grupo de Química Orgánica, Centro de Investigación Científica de Yucatán, Calle 43 No. 130, Colonia Chuburná, Mérida, Yucatán, Mexico 97200.
Escalante-Erosa
Fabiola
F
García-Sosa
Karlina
K
Alejos-González
Fátima
F
Delgado-Lamas
Guillermo
G
Peña-Rodríguez
Luis M
LM
D000528:Alternaria / Q000737:chemistry* / Q000378:metabolism; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008968:Molecular Conformation; D009183:Mycotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D013329:Structure-Activity Relationship; D014992:Xylenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism
D009183:Mycotoxins; D014992:Xylenes; C051798:zinniol