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Vercytochalasins A and B: Two unprecedented biosynthetically related cytochalasins from the deep-sea-sourced endozoic fungus Curvularia verruculosa

引用

Chinese Chemical Letters 2023年第2期34卷 407-411页

作者： Xueyi Hu Xiaoming Li Suiqun Yang Xin Li Bingui Wang Linghong Meng CAS and Shandong Province Key Laboratory of Experimental Marine Biology Institute of OceanologyChinese Academy of Sciencesand Laboratory of Marine Biology and BiotechnologyQingdao National Laboratory for Marine Science and TechnologyQingdao 266071China College of Marine Sciences University of Chinese Academy of SciencesBeijing 100049China Center for Ocean Mega-Science Chinese Academy of SciencesQingdao 266071China

Vercytochalasins A(1) and B(2), two biosynthetically related cytochalasins featuring novel structure and substituents, were isolated from the endozoic fungus Curvularia verruculosa which was associated with the deep-sea squat lobster Shinkaia crosnieri collected from the cold seep environment in South China sea. Their structures were elucidated by detailed interpretation of NMR spectroscopic and mass spectrometric data. The absolute configurations were confirmed by NOESY experiments as well as by DP4+ and ECD calculations. Differed from common cytochalasins, compound 1 is an uncommon secocytochalasin featuring the ester group cleaved between C-9 and C-23, and incorporating an additional oxygenated C4 unit which coupled with C-20 and C-22 to form a new substituted cyclohexenone moiety, while compound 2 contains an unusual 2–hydroxy-3-oxobutan-2-yl unit at C-22. Both compounds are distinctive from the commonly described cytochalasins. Compound 1 exhibited potent activity against angiotensini-converting enzyme(ACE) whereas compound 2 showed antibacterial activity. Molecular docking simulations were performed to explore the intermolecular interaction of compounds 1 and 2 with ACE.

关键词： Deep sea Endozoic fungus Curvularia verruculosa Cytochalasins angiotensin-i-converting enzyme inhibitory activity

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