Tagetolone and Tagetenolone:  Two Phytotoxic Polyketides from Alternaria tagetica

• Published in: Journal of agricultural and food chemistry Vol. 49; no. 3; pp. 1228 - 1232
• Main Authors: Gamboa-Angulo, M. Marcela, García-Sosa, Karlina, Alejos-González, Fátima, Escalante-Erosa, Fabiola, Delgado-Lamas, Guillermo, Peña-Rodríguez, Luis M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.03.2001; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Alternaria - chemistry; Alternaria - growth & development; Alternaria - pathogenicity; Biological and medical sciences; Chemistry; Chemistry, Applied; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Mycotoxins - chemistry; Mycotoxins - isolation & purification; Parabens - chemistry; Parabens - isolation & purification; Parabens - pharmacology; Pathology, epidemiology, host-fungus relationships. Damages, economic importance; Phenylethyl Alcohol - analogs & derivatives; Phenylethyl Alcohol - isolation & purification; Physical Sciences; Phytopathology. Animal pests. Plant and forest protection; Plants - microbiology; Science & Technology; Xylenes - chemistry; phytotoxins; METABOLITES; tagetenolone; tagetolone; Tagetes erecta; marigold; TOXINS; tryrosol; p-hydroxybenzoic acid; Alternaria tagetica; PATHOGENS; Purification; Plant pathogen; Phytotoxin; Mycotoxin; Host agent relation; Identification; Compositae; Fungi; Characterization; Toxin; Phytotoxicity; Dicotyledones; Angiospermae; Flower crop; Isolation; Spermatophyta; Fungi Imperfecti; Thallophyta
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf000872k

Two new phytotoxic polyketides, tagetolone (1) and tagetenolone (2), in addition to tyrosol and p-hydroxybenzoic acid, have been isolated from the organic crude extract of culture filtrates from the fungal pathogen Alternaria tagetica. Complete characterization of all structures was carried out following a careful analysis of their spectroscopic data (IR, MS, 1H and 13C NMR, and 2D NMR experiments). Keywords: Alternaria tagetica; Tagetes erecta; phytotoxins; marigold; tagetolone; tagetenolone; tyrosol; p-hydroxybenzoic acid