Xanthchrysones A–C: Rearranged Phenylpropanoyl–Phloroglucinol Dimers with Unusual Skeletons from Xanthostemon chrysanthus

作者：Fen Liu, Hai‐Yan Tian, Xiaolin Huang, Wen‐Jing Wang, Ni-Ping Li, Jun He, Wen‐Cai Ye, Lei Wang · 发表于：The Journal of Organic Chemistry · 年份：2019 · DOI：10.1021/acs.joc.9b02373 · 被引用次数：19 · 研究领域：Natural Compound Pharmacology Studies、Bioactive Compounds and Antitumor Agents、Bioactive natural compounds

Three pairs of dimeric phenylpropanoyl–phloroglucinol enantiomers, (+)- and (−)-xanthchrysones A–C [(+)- and (−)- 1–3 ], as well as their postulated biosynthetic precursors, were isolated and identified from the leaves of Xanthostemon chrysanthus . Compound 1 featured an unprecedented bis-phenylpropanoyl-benzo[ b ]cyclopent[ e ] oxepine tricyclic backbone. Compounds 2 and 3 represent the first examples of 1-(cyclopentylmethyl)-3-(3-phenylpropanoyl)benzene scaffold. The structures and absolute configurations of 1 – 3 were determined by spectroscopic and X-ray diffraction analysis as well as electronic circular dichroism (ECD) calculation. Both (+)- 2 and (−)- 2 showed moderate antibacterial activities including several multidrug-resistant strains.