Higginsianin F, one skeletal rearrangement diterpenoid α-pyridone with phytotoxic activity isolated from Colletotrichum higginsianum

文献类型： 外文期刊

第一作者： Chen, Kang

作者： Chen, Kang;Song, Kainan;Hao, Xiaoyang;Wang, Chen;Zhang, Liwen;Yue, Qun;Xie, Linan;Xu, Yuquan;Wang, Chen;Zhang, Liwen;Yue, Qun;Xie, Linan;Xu, Yuquan

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关键词： Colletotrichum higginsianum; Glomerellaceae; Amaranthus retroflexus; Chenopodium album; Phytotoxicity; Fungal natural products; Diterpenoid pyrones

期刊名称：PHYTOCHEMISTRY （ 影响因子：3.4； 五年影响因子：3.6 ）

ISSN： 0031-9422

年卷期： 2025 年 235 卷

页码：

收录情况： SCI

摘要： Higginsianin F (1), a previously undescribed diterpenoid alpha-pyridone skeleton featuring a unique N-hydroxyethyl3-(5-acetyl-4-hydroxy)-alpha-pyridone ring, along with three undescribed diterpenoid pyrones, higginsianins G-I (2-4), were isolated from the mycelium of the phytopathogenic fungus Colletotrichum higginsianum. Their structures were elucidated through comprehensive analysis using NMR, HRESIMS, and ECD experiments. The absolute configuration of compound 2 was determined to be opposite to the other three compounds based on ECD experiments and the measured optical rotation value. A biosynthetic pathway for the N-hydroxyethyl-3-(5acetyl-4-hydroxy)-alpha-pyridone ring in 1 was proposed, involving a key Friedel-Crafts acylation reaction. Compound 1 exhibited potential phytotoxic activity, inducing the formation of necrotic spots on Chenopodium album L. leaves at a concentration of 2 mu g/mu L, and inhibiting the germination of Amaranthus retroflexus L. seeds by 94.8 % at a concentration of 1000 mu g/mL.

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