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Modified Fusicoccane-Type Diterpenoids from <i>Alternaria brassicicola</i>

Fengli Li, Shuang Lin, Sitian Zhang, Lifen Pan, Chenwei Chai, Jun‐Cheng Su, Beiye Yang, Junjun Liu, Jianping Wang, Zhengxi Hu, Yonghui Zhang

2020Journal of Natural Products35 citationsDOI

Abstract

Seven new modified fusicoccane-type diterpenoids (1–7), together with two known congeners (8 and 9), were obtained from Alternaria brassicicola. Their structures were elucidated from a combination of NMR and HRESIMS data and 13C NMR calculation as well as DP4+ probability analyses, and the absolute configurations of 1–5 were determined by ECD calculation and single-crystal X-ray diffraction (Cu Kα). Compounds 1–3 belong to a rare class of 16-nor-dicyclopenta[a,d]cyclooctane diterpenoids, and compounds 2 and 4 represent the first examples of fusicoccane-type diterpenoids featuring two previously undescribed tetracyclic 5/6/6/5 ring systems, while compound 5 features a previously undescribed tetracyclic 5/8/5/3 ring system. Compound 7 was moderately anti-inflammatory, and compounds 2, 3, 5, and 7 were weakly cytotoxic.

Topics & Concepts

CyclooctaneStereochemistryRing (chemistry)ChemistryType (biology)Organic chemistryBiologyCatalysisEcology14-3-3 protein interactionsMicrobial Natural Products and BiosynthesisFungal Plant Pathogen Control
Modified Fusicoccane-Type Diterpenoids from <i>Alternaria brassicicola</i> | Litcius