title: Natural zinniol derivatives from Alternaria tagetica. Isolation, synthesis, and structure-activity correlation.
abstract: 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).
authors.affiliation: Grupo de Química Orgánica, Centro de Investigación Científica de Yucatán, Calle 43 No. 130, Colonia Chuburná, Mérida, Yucatán, Mexico 97200.
authors.forename: M Marcela
authors.initials: MM
authors.lastname: Gamboa-Angulo
authors.forename: Fabiola
authors.initials: F
authors.lastname: Escalante-Erosa
authors.forename: Karlina
authors.initials: K
authors.lastname: García-Sosa
authors.forename: Fátima
authors.initials: F
authors.lastname: Alejos-González
authors.forename: Guillermo
authors.initials: G
authors.lastname: Delgado-Lamas
authors.forename: Luis M
authors.initials: LM
authors.lastname: Peña-Rodríguez
mesh_terms: 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
chemical_list: D009183:Mycotoxins; D014992:Xylenes; C051798:zinniol