Bioactive Enmein-Type ent-Kaurane Diterpenoids from Isodon phyllostachys

  • J Nat Prod. 2016 Jan 22;79(1):132-40. doi: 10.1021/acs.jnatprod.5b00802.
Jin Yang  1  2 ,  Wei-Guang Wang  1 ,  Hai-Yan Wu  1  2 ,  Xue Du  1 ,  Xiao-Nian Li  1 ,  Yan Li  1 ,  Jian-Xin Pu  1 ,  Han-Dong Sun  1
Affiliations
  • 1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.
  • 2. University of Chinese Academy of Sciences , Beijing 100049, People's Republic of China.
PMID: 26757019 DOI: 10.1021/acs.jnatprod.5b00802
Abstract

Thirty-two enmein-type ent-kaurane Diterpenoids, including 13 new compounds, were isolated from the aerial parts of Isodon phyllostachys. Compounds 1 and 2 are the first examples of 3,20:6,20-diepoxyenmein-type ent-kauranoids, and the structures of these new compounds were established mainly by analyzing NMR and HREIMS data. The absolute configurations of 1 and 8 and the relative configuration of 9 were determined using single-crystal X-ray diffraction. Compounds 11, 15, 20, and 21 were active against five human Cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), with IC50 values ranging from 1.2 to 5.0 μM. Compounds 3, 11, 15, 17, 20, 21, 25, and 29 strongly inhibited NO production in LPS-stimulated RAW264.7 cells, with IC50 values ranging from 0.74 to 4.93 μM.