Nitrogen Oxide Inhibitory Trimeric and Dimeric Carbazole Alkaloids from Murraya tetramera.
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.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.
Hai-Ning
HN
Lv
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.
Ran
R
Wen
Zhejiang Institute for Food and Drug Control, Hangzhou 310004, People's Republic of China.
Ying
Y
Zhou
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.
Ke-Wu
KW
Zeng
Modern Research Center for Traditional Chinese Medicine, Beijing University of Chinese Medicine , Beijing 100029, People's Republic of China.
Jun
J
Li
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.
Xiao-Yu
XY
Guo
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.
Peng-Fei
PF
Tu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.
Yong
Y
Jiang
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D002227:Carbazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides / Q000494:pharmacology; D051379:Mice; D017628:Microglia / Q000187:drug effects; D015394:Molecular Structure; D032101:Murraya / Q000737:chemistry*; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry
D000470:Alkaloids; D002227:Carbazoles; D004365:Drugs, Chinese Herbal; D008070:Lipopolysaccharides; C000604835:murratrine A; D009569:Nitric Oxide