来自四数九里香的氮氧化物抑制性三聚体和二聚体咔唑生物碱。

Nitrogen Oxide Inhibitory Trimeric and Dimeric Carbazole Alkaloids from Murraya tetramera.

作者信息

Lv Hai-Ning, Wen Ran, Zhou Ying, Zeng Ke-Wu, Li Jun, Guo Xiao-Yu, Tu Peng-Fei, Jiang Yong

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University , Beijing 100191, People's Republic of China.

Zhejiang Institute for Food and Drug Control, Hangzhou 310004, People's Republic of China.

出版信息

J Nat Prod. 2015 Oct 23;78(10):2432-9. doi: 10.1021/acs.jnatprod.5b00527. Epub 2015 Sep 1.

DOI:10.1021/acs.jnatprod.5b00527

PMID:26327273

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.

摘要

从四数九里香的叶和茎中分离得到了两种结构独特的新型三聚咔唑生物碱——九里香素A和B（1, 2）、11种新型咔唑二聚体——九里香碱A - K（3 - 13）以及4种已知类似物（14 - 17）。通过综合一维和二维核磁共振波谱、高分辨率质谱以及电子圆二色光谱（ECD）数据分析，阐明了化合物1 - 13的结构和相对构型。九里香素A和B（1, 2）均含有前所未有的咔唑三聚体骨架，而九里香碱A和D（3, 6）分别是首例天然的C - 1 - C - 3'-甲基连接和C - 6 - C - 3'-甲基连接的二聚咔唑生物碱。化合物4、10、14、15和17在BV - 2小胶质细胞中对脂多糖刺激产生的一氧化氮具有抑制作用，IC50值在11.2 - 19.3 μM范围内。