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Unexpected Noremestrin with a Sulfur-Bearing 15-Membered Macrocyclic Lactone from <i>Emericella</i> sp. 1454

Yu‐Chuan Chen, Tongmei Xiao, Shuyue Guo, Shanshan Chang, Xiaoming Xi, Bingjie Su, Tao Zhang, Liyan Yu, Wuli Zhao, Jingshuai Wu, Yan Li, Shuyi Si, Minghua Chen

2023Organic Letters13 citationsDOI

Abstract

Two previous unreported epipolythiodioxopiperazines of the emestrin family, namely, noremestrin A ( 1 ) and secoemestrin E ( 2 ), were successfully isolated from the fungal source Emericella sp. 1454. Employing comprehensive spectroscopic techniques, such as high-resolution electrospray ionization mass spectrometry, infrared, and nuclear magnetic resonance (NMR), along with NMR and electronic circular dichroism calculations, the chemical structures of compounds 1 and 2 were elucidated. Particularly noteworthy is the distinctive nature of noremestrin A, representing the inaugural instance of a noremestrin variant incorporating a sulfur-bearing 15-membered macrocyclic lactone moiety. Compounds 1 and 2 exhibited weak cytotoxic activities against the human chronic myelocytic leukemia cell lines MEG-01 and K562.

Topics & Concepts

ChemistryMoietyStereochemistryCircular dichroismElectrospray ionizationLactoneMass spectrometrySulfurK562 cellsCrystallographyOrganic chemistryIn vitroBiochemistryChromatographyMicrobial Natural Products and BiosynthesisFungal Biology and ApplicationsMarine Sponges and Natural Products