来自 sp. B15-008 的 Vertirhodins A-F、含吡咯烷亚氨基糖的 C-连接吡喃萘醌
Vertirhodins A-F, C-Linked Pyrrolidine-Iminosugar-Containing Pyranonaphthoquinones from sp. B15-008.
机构信息
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892-0820, United States.
出版信息
Org Lett. 2021 Feb 5;23(3):682-686. doi: 10.1021/acs.orglett.0c03825. Epub 2021 Jan 14.
Abstract
Six novel pyranonaphthoquinones, vertirhodins A-F (-), were discovered from a soil-derived sp. B15-008. Their chemical structures and absolute configurations were determined using nuclear magnetic resonance and comparison of experimental and theoretical electronic circular dichroism spectra. The vertirhodins feature an unusual C-8 -methyl-2-pyrrolidinemethanol moiety, a 5,14-epoxide rarely seen in streptomyces-derived natural products, and a C-13 hydroxyl group that forms the semiquinone. A plausible biosynthetic gene cluster was identified through whole genome sequencing and provides insights into these features.
摘要
从土壤来源的 sp. B15-008 中发现了六种新型吡喃萘醌，即 vertirhodins A-F(-)。通过核磁共振和实验与理论电子圆二色谱的比较，确定了它们的化学结构和绝对构型。Vertirhodins 具有一个不寻常的 C-8 -甲基-2-吡咯烷甲醇部分、在链霉菌来源的天然产物中很少见的 5,14-环氧和一个形成半醌的 C-13 羟基。通过全基因组测序鉴定了一个可能的生物合成基因簇，为这些特征提供了线索。
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