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Diverse Prenylated Bibenzyl Enantiomers from the Chinese Liverwort Radula apiculata and Their Cytotoxic Activities.

Chun-Yang ZhangYun GaoJin-Chuan ZhouZe-Jun XuYa-Nan QiaoJiao-Zhen ZhangHong-Xiang Lou
Published in: Journal of natural products (2021)
An EtOH extract of the Chinese liverwort Radula apiculata showed cytotoxic activity against the A549 lung cancer cell line. Bioassay-guided fractionation led to the isolation of 19 prenylated bibenzyls, including eight previously unknown dimeric prenylated bibenzyls [radulapins A-H (1-8)], four new prenylated bibenzyls (9-12), and seven known compounds (13-19). Compounds 1-11 were analyzed as racemates by chiral-phase separation. Their structures were determined by detailed analysis of their spectroscopic data and by single-crystal X-ray diffraction, chiral resolutions, and electronic circular dichroism measurements. Using an MTT assay, these dimers (1-8) showed significant cytotoxic activity against a panel of human cancer cell lines. Further investigation revealed that compound 4 induces PC-3 cell death via mitochondrial-derived apoptosis.
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