pH Modulation of Zopfiellin Antifungal Activity to Colletotrichum and Botrytis

• Published in: Journal of agricultural and food chemistry Vol. 50; no. 24; pp. 7007 - 7012
• Main Authors: Futagawa, Mitsugu, Rimando, Agnes M, Tellez, Mario R, Wedge, David E
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 20.11.2002
• Subjects: Ascomycota - chemistry; Biological and medical sciences; Botrytis - drug effects; Chemical control; Chromatography, High Pressure Liquid; Colletotrichum - drug effects; Control; Cyclooctanes - chemistry; Cyclooctanes - isolation & purification; Cyclooctanes - pharmacology; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; Fungicides, Industrial - chemistry; Fungicides, Industrial - isolation & purification; Fungicides, Industrial - pharmacology; Fusarium - drug effects; Hydrogen-Ion Concentration; Magnetic Resonance Spectroscopy; Mass Spectrometry; Phytopathology. Animal pests. Plant and forest protection; Plant Diseases - microbiology; Performance evaluation; Plant pathogen; Botrytis cinerea; Biological control; Environmental factor; Fungi; natural products; Antifungal agent; Colletotrichum fragariae; Chemical control; Fusarlum oxysporum; pH; Ascomycetes; Mould; Colletotrichum gloeosporloldes; Fungi Imperfecti; Colletotrichum acutatum; Thallophyta; Fusarium oxysporum; Pesticides; Pest and disease control; Chemical structure; Natural product; Fungicide; Biological activity; Microbial fungicide; zopflellin; Colletotrichum gloeosporioides; Zopflella curvata
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf025720z

Zopfiellin, a novel cyclooctanoid natural product isolated from Zopfiella curvata No. 37-3, was evaluated in a 96-well microtiter assay for fungicidal activity against Botrytis cinerea, Colletotrichum acutatum, Colletotrichum fragariae, Colletotrichum gloeosporioides, and Fusarium oxysporum. Zopfiellin exhibited pH-dependent activity, with the most mycelial growth inhibition demonstrated at pH 5.0. Mass spectrometry and nuclear magnetic resonance spectroscopy studies indicated that zopfiellin undergoes structural changes with changes in pH. At pH 5.0, zopfiellin showed the greatest activity against B. cinerea (IC80 = 10 μM), C. gloeosporioides (IC80 = 10 μM), and C. fragariae (IC80 = 10 μM) and intermediate activity against C. acutatum (IC80 = 30 μM), and was not active against F. oxysporum (IC80 > 100 μM). Keywords: Fungicide; natural products; zopfiellin; Zopfiella curvata; Botrytis cinerea; Colletotrichum acutatum; Colletotrichum fragariae; Colletotrichum gloeosporioides; Fusarium oxysporum