Bioactive quassinoids from the seeds of Brucea javanica

  • J Nat Prod. 2012 Apr 27;75(4):683-8. doi: 10.1021/np200920c.
Jun-Hong Liu  1 ,  Nan Zhao ,  Gui-Jie Zhang ,  Shi-Shan Yu ,  Li-Jun Wu ,  Jing Qu ,  Shuang-Gang Ma ,  Xiao-Guang Chen ,  Tian-Qi Zhang ,  Jian Bai ,  Hui Chen ,  Zhen-Feng Fang ,  Fen Zhao ,  Wei-Bin Tang
Affiliations
  • 1. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, NO.1 Xian Nong Tan Street, Beijing 100050, People's Republic of China.
PMID: 22506620 DOI: 10.1021/np200920c
Abstract

Six new quassinoids (1-6) and eight known compounds of this type (7-14) were isolated from the seeds of Brucea javanica. Their structures were elucidated by analysis of their spectroscopic data and from chemical evidence. Compounds 1-5 were found to be unusual quassinoids with a 2,3-seco A ring. The configurations at C-4 in 4 and 5 were determined by a difference circular dichroism method. In in vitro bioassays, 8 and 10 showed inhibitory activities for nitric oxide production in LPS-activated macrophages, with IC(50) values of 1.9 and 5.0 μM, respectively, while compounds 6, 8-11, 13, and 14 exhibited cytotoxicity against five human tumor cell lines (HCT-8, HepG2, BGC-823, A549, and SKVO3), having IC(50) values in the range 0.12-9.3 μM.