Quinone Derivatives as Promising Anti- Helicobacter pylori Agents from Aerial Parts of Mitracarpus hirtus

作者：Mingming Xu, Junfei Zhou, Ding Heng, Xiaorong Su, Monday M. Onakpa, Yuefan Bai, Jin‐Ao Duan, Chun‐Tao Che, Hongkai Bi, Ming Zhao · 发表于：Journal of Natural Products · 年份：2022 · DOI：10.1021/acs.jnatprod.1c01163 · 被引用次数：15 · 研究领域：Helicobacter pylori-related gastroenterology studies、Bioactive Compounds and Antitumor Agents、Phytochemistry and Bioactive Compounds

Seven new naphthoquinone diglycosides ( 1 – 7 ), three new anthraquinones ( 8 – 10 ), and eight known analogues were obtained from the aerial parts of Mitracarpus hirtus collected from West Africa in a bioassay-guided phytochemical investigation. All isolated compounds were elucidated by comparison with the literature and interpretation of spectroscopic data, and the absolute configurations of the new naphthoquinone diglycosides ( 1 – 10 ) were confirmed by chemical methods and ECD calculations. Notably, compound 1 was found to be the first naphthoquinone diglycoside containing carboxylic acid and isopentenyl side chains isolated from a species in the genus Mitracarpus . Compounds 6 – 18 showed antibacterial activity against multiple Helicobacter pylori strains with MIC values ranging from 0.0625 to 64 μg/mL. Particularly, 1-hydroxybenzoisochromanquinone ( 17 ) and benzo[ g ]isoquinoline-5,10-dione ( 18 ), with MIC values of 0.0625 and 0.125 μg/mL, displayed 32–512-fold higher potencies than a positive control, metronidazole. Compound 18 also demonstrated high antibiofilm activity and killed biofilm-encased Helicobacter pylori cells more effectively than metronidazole.