Prenylated Bibenzyls from the Chinese Liverwort Radula constricta and Their Mitochondria-Derived Paraptotic Cytotoxic Activities

  • J Nat Prod. 2019 Jul 26;82(7):1741-1751. doi: 10.1021/acs.jnatprod.8b00897.
Chun-Yang Zhang  1 ,  Yun Gao  1 ,  Rong-Xiu Zhu  2 ,  Ya-Nan Qiao  1 ,  Jin-Chuan Zhou  3 ,  Jiao-Zhen Zhang  1 ,  Yi Li  1 ,  Si-Wen Li  1 ,  Sheng-Hua Fan  1 ,  Hong-Xiang Lou  1
Affiliations
  • 1. Department of Natural Products Chemistry, Key Lab of Chemical Biology of the Ministry of Education , Shandong University , Jinan 250012 , People's Republic of China.
  • 2. School of Chemistry and Chemical Engineering , Shandong University , Jinan 250010 , People's Republic of China.
  • 3. School of Pharmacy , Linyi University , Linyi 276000 , People's Republic of China.
PMID: 31268321 DOI: 10.1021/acs.jnatprod.8b00897
Abstract

Nine new prenylated bibenzyls, radstrictins A-I (1-9), and 11 known congeners were obtained from the Chinese liverwort Radula constricta. Their structures were identified by analysis of HRMS, NMR, and electronic circular dichroism data. Radstrictins A-F (1-6) were isolated as a racemate or scalemic mixtures. All the isolated compounds were subjected to cytotoxicity assessment. Methyl 2,4-dihydroxy-3-(3-methyl-2-butenyl)-6-phenethylbenzoate (10) exhibited significant activity against human lung Cancer cell lines A549 and NCI-H1299 with IC50 values of 6.0 and 5.1 μM, respectively. Further research revealed that cell death triggered by 10 occurred via mitochondria-derived Paraptosis.