Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 23, Pages 15355-15361Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02373
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Funding
- National Key R&D Program of China [2017YFC1703800]
- Program for the National Natural Science Foundation of China [81822042, 81630095, 81603165]
- Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program [2017BT01Y036]
- Guangdong Natural Science Foundation for Distinguished Young Scholars [2015A030306022]
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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.
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