Homozinniol, a New Phytotoxic Metabolite from Alternaria solani

• Published in: Journal of agricultural and food chemistry Vol. 45; no. 1; pp. 282 - 285
• Main Authors: GamboaAngulo, MM, AlejosGonzalez, F, PenaRodriguez, LM
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.01.1997; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; ALTERNARIA SOLANI; BIOASSAYS; Biological and medical sciences; Chemistry; Chemistry, Applied; COMPOSE HETEROCYCLIQUE; COMPUESTOS HETEROCICLICOS; ENSAYO BIOLOGICO; FITOTOXINAS; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; HETEROCYCLIC COMPOUNDS; IDENTIFICACION; IDENTIFICATION; ISOLATION; Life Sciences & Biomedicine; METABOLITE; METABOLITES; METABOLITOS; Pathology, epidemiology, host-fungus relationships. Damages, economic importance; PHTHALIDES; Physical Sciences; Phytopathology. Animal pests. Plant and forest protection; PHYTOTOXINE; PHYTOTOXINS; POLYKETIDES; Science & Technology; TEST BIOLOGIQUE; zinniol; Alternaria solani; homozinniol; Solanum tuberosum; phytotoxin; polyketide; PORRI; Lycopersicon esculentum; phthalide; PATHOGENS; Plant pathogen; Phytotoxin; Metabolite; Chemical structure; NMR spectrometry; Fungi; Microbial origin; Benzenic compound; Fungi Imperfecti; Phthalic acid derivatives; Mass spectrometry; Thallophyta
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf960134p

A bioassay-guided fractionation of the phytotoxic crude extract of Alternaria solani resulted in the isolation of two phytotoxic metabolites identified as zinniol (1) and a new polyketide:  homozinniol (2). A third metabolite, 6-[(3‘,3‘-dimethylallyl)oxy]-4-methoxy-5-methylphthalide (3) was also isolated and identified. Structural assignment of the metabolites was based primarily on the analysis of their mass spectrometry and 1H NMR spectroscopy data. Keywords: Alternaria solani; Solanum tuberosum; Lycopersicon esculentum; phytotoxin; zinniol; homozinniol; polyketide; phthalide