Colletochlorins E and F, New Phytotoxic Tetrasubstituted Pyran-2-one and Dihydrobenzofuran, Isolated from Colletotrichum higginsianum with Potential Herbicidal Activity

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• 作者：Marco Masi ; Alessio Cimmino ; Angela Boari ; Angela Tuzi ; Maria Chiara Zonno ; Riccardo Baroncelli ; Maurizio Vurro ; Antonio Evidente
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2017
• 出版时间：February 15, 2017
• 年：2017
• 卷：65
• 期：6
• 页码：1124-1130
• 全文大小：303K
• ISSN：1520-5118

文摘

A new tetrasubstituted pyran-2-one and a new dihydrobenzofuran, named colletochlorins E and F (1 and 2, respectively), were isolated from the culture filtrates of the fungus Colletotrichum higginsianum together with the already known colletochlorin A, 4-chloroorcinol, and colletopyrone. Colletochlorin E, the main metabolite, and colletochlorin F were characterized by spectroscopic (NMR, HRESIMS) and chemical methods as 3-[7-chloro-4-hydroxy-2-(1-hydroxy-1-methylethyl)-6-methyl-2,3-dihydrobenzofuran-5-ylmethyl]-4-hydroxy-5,6-dimethylpyran-2-one and 7-chloro-2-(1-hydroxy-1-methylethyl)-6-methyl-2,3-dihydrobenzofuran-4-ol, respectively. The absolute configuration 2′S of 1 was deduced by X-ray diffractometric analysis, whereas 2S of 2 was deduced by comparison of its NMR and CD data with those of 1. When assayed by leaf puncture on Sonchus arvensis and tomato leaves, 2 caused quite large necrosis (>1 cm), whereas 4-chloroorcinol proved to be the most active compound. These results were confirmed by those obtained in assays on Lemna minor and Phelipanche ramosa seed germination. Furthermore 1, colletochlorin A and colletopyrone were less or modestly active in the latter assay, respectively. Interestingly, the phytotoxicity was not associated with an antibiotic activity, whereas only 4-chloroorcinol and colletochlorin F exhibited zootoxic activity.