Antifungal and antioomycete activities and modes of action of isobenzofuranones isolated from the endophytic fungus Hypoxylon anthochroum strain Gseg1,Pesticide Biochemistry and Physiology

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Antifungal and antioomycete activities and modes of action of isobenzofuranones isolated from the endophytic fungus Hypoxylon anthochroum strain Gseg1
Pesticide Biochemistry and Physiology ( IF 4.2 ) Pub Date : 2020-10-01 , DOI: 10.1016/j.pestbp.2020.104670
Rosa Elvira Sánchez-Fernández ₁ , Rosalía Sánchez-Fuentes ₁ , Hiram Rangel-Sánchez ₂ , Simón Hernández-Ortega ₃ , José G López-Cortés ₂ , Martha Lydia Macías-Rubalcava ₁

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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.

中文翻译：

从内生真菌 Hypoxylon anthochroum Gseg1 菌株中分离的异苯并呋喃酮的抗真菌和抗卵菌活性和作用方式

Hypoxylon 物种分布在世界各地，并已从不同的栖息地中分离出来。从 Gliricidia sepium 的健康叶子中分离出内生菌 Hypoxylon anthochroum 菌株 Gseg1。对内生真菌 H. anthochroum Gseg1 的培养基和菌丝体有机提取物的化学研究导致分离出三种已知的异苯并呋喃酮，7-羟基-4,6-二甲基-3H-异苯并呋喃-1-one, 1, 7-甲氧基-4,6-二甲基-3H-异苯并呋喃-1-酮, 2, 6-甲酰基-4-甲基-7-甲氧基-3H-异苯并呋喃-1-one, 3, 1个化合物首次分离为一种天然产物，7-甲氧基-4-甲基-3H-异苯并呋喃-1-one，4。此外，1和2的化学合成，以及衍生物，7-甲氧基-6-甲基-3H-异苯并呋喃-1 -一，5，进行了。异苯并呋喃酮显示出抗真菌和抗卵菌活性。化合物1-5抑制尖孢镰刀菌、链格孢、腐霉和辣椒疫霉的生长，此外，化合物1、2和5由于细胞膜损伤而中断呼吸并引起电解质泄漏。化合物2活性最强，抑制四种微生物的生长，影响呼吸作用，并因电解质泄漏而增加相对电导率。化合物 1-4 还诱导植物病原体菌丝体和菌丝的形态变化。这些化合物可用于控制与农业相关的植物病原真菌和卵菌。化合物2活性最强，抑制四种微生物的生长，影响呼吸作用，并因电解质泄漏而增加相对电导率。化合物 1-4 还诱导植物病原体菌丝体和菌丝的形态变化。这些化合物可用于控制与农业相关的植物病原真菌和卵菌。化合物2活性最强，抑制四种微生物的生长，影响呼吸作用，并因电解质泄漏而增加相对电导率。化合物 1-4 还诱导植物病原体菌丝体和菌丝的形态变化。这些化合物可用于控制与农业相关的植物病原真菌和卵菌。

更新日期：2020-10-01

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