Journal
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
Volume 169, Issue -, Pages -Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.pestbp.2020.104670
Keywords
Hypoxylon anthochroum; Nodulisporium sp; Isobenzofuranones; Phthalides; Antifungal; Antioomycete; Endophyte
Categories
Funding
- Consejo Nacional de Ciencia y Tecnologia, Mexico (CONACyT) [A1-S-20469, 02291222]
- Programa de Apoyo a Proyectos de Investigacion e Innovacion Tecnologica (PAPIIT-DGAPA) [UNAM IN207117, IN210920]
- CONACyT Mexico [0224747]
- UNAM
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Hypoxylon species are distributed worldwide and have been isolated from different habitats. The endophyte Hypoxylon anthochroum strain Gseg1 was isolated from healthy leaves of Gliricidia sepium. A chemical study of the culture medium and mycelium organic extracts of the endophytic fungus H. anthochroum Gseg1 led to the isolation of three known isobenzofuranones, 7-hydroxy-4,6-dimethyl-3H-isobenzofuran-1-one, 1, 7-methoxy-4,6-dimethyl-3H-isobenzofuran-1-one, 2, 6-formyl-4-methyl-7-methoxy-3H-isobenzofuran-1-one, 3, and one compound was isolated for the first time as a natural product, 7-methoxy-4-methyl-3H-isobenzofuran-1-one, 4. In addition, the chemical synthesis of 1 and 2, and a derivative, 7-methoxy-6-methyl-3H-isobenzofuran-1-one, 5, was performed. The isobenzofuranones showed antifungal and antioomycete activities. Compounds 1-5 inhibited the growth of Fusarium oxysporum, Alternaria alternata, Pythium aphanidermatum, and Phytophthora capsici, in addition, 1, 2 and 5 interrupted the respiration and caused electrolyte leakage due to cell membrane damage. Compound 2 was the most active, inhibiting the growth of the four microorganisms, affecting the respiration and increasing the relative conductivity due to electrolyte leakage. Compounds 1-4 also induce morphological changes in the plant pathogens' mycelia and hyphae. These compounds could be useful for the control of plant pathogenic fungi and oomycetes of agricultural relevance.
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