Nitrogen Oxide Inhibitory Trimeric and Dimeric Carbazole Alkaloids from Murraya tetramera

  • J Nat Prod. 2015 Oct 23;78(10):2432-9. doi: 10.1021/acs.jnatprod.5b00527.
Hai-Ning Lv  1 ,  Ran Wen  1 ,  Ying Zhou  2 ,  Ke-Wu Zeng  1 ,  Jun Li  3 ,  Xiao-Yu Guo  1 ,  Peng-Fei Tu  1 ,  Yong Jiang  1
Affiliations
  • 1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.
  • 2. Zhejiang Institute for Food and Drug Control, Hangzhou 310004, People's Republic of China.
  • 3. Modern Research Center for Traditional Chinese Medicine, Beijing University of Chinese Medicine , Beijing 100029, People's Republic of China.
PMID: 26327273 DOI: 10.1021/acs.jnatprod.5b00527
Abstract

Two new structurally unique trimeric Carbazole Alkaloids, murratrines A and B (1, 2), and 11 new carbazole dimers, murradines A-K (3-13), and four known analogues (14-17) were isolated from the leaves and stems of Murraya tetramera. The structures and relative configurations of 1-13 were elucidated on the basis of comprehensive 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and electronic circular dichroism (ECD) data analysis. Murratrines A and B (1, 2) both contain an unprecedented carbazole trimeric skeleton, and murradines A and D (3, 6) are the first natural C-1-C-3'-methyl-linked and C-6-C-3'-methyl-linked dimeric Carbazole Alkaloids, respectively. Compounds 4, 10, 14, 15, and 17 exhibited inhibition of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC50 values in the range of 11.2-19.3 μM.