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Trichothecrotocins D–L, Antifungal Agents from a Potato-Associated <i>Trichothecium crotocinigenum</i>

Huixiang Yang, Juan He, Falei Zhang, Xian-Dong Zhang, Zheng-Hui Li, Tao Feng, Hong‐Lian Ai, Ji‐Kai Liu

2020Journal of Natural Products16 citationsDOI

Abstract

Seven new merosesquiterpenoids, trichothecrotocins D–J (1–7), two new trichothecene sesquiterpenoids, trichothecrotocins K (12) and L (13), and six known compounds (8–11, 14, and 15), were isolated from a potato-associated fungus, Trichothecium crotocinigenum. Compounds 5 and 6 were racemates which were further separated as pure enantiomers. Structures together with absolute configurations were established by extensive spectroscopic analysis, as well as quantum chemistry calculations on ECD and optical rotations. Compounds 1–4 are rare meroterpenoids featuring a seco-phenyl group, while 1 and 2 possessed a novel 6–6/5 fused ring system. Compounds 1–4, 8, 11, and 12 showed antifungal activity against four plant pathogens with MIC values of 8–128 μg/mL. It is suggested that the meroterpenoids produced by T. crotocinigenum may play an important role in the antifungal property of the fungus, thereby protecting the host plant, i.e., potato.

Topics & Concepts

TrichotheceneAntifungalStereochemistryEnantiomerFungusChemistryBiologyBotanyMicrobiologyFood scienceMycotoxinMicrobial Natural Products and BiosynthesisPlant and animal studiesChemical synthesis and alkaloids