Natural Products from Murraya tetramera

Chemical Constituents of Murraya tetramera Huang and Their Repellent Activity against Tribolium castaneum.[Pubmed: 28825643]

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Nitrogen Oxide Inhibitory Trimeric and Dimeric Carbazole Alkaloids from Murraya tetramera.[Pubmed: 26327273]

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.

Cytotoxic compounds isolated from Murraya tetramera Huang.[Pubmed: 25165861]

A new compound and seven known compounds were isolated from Murraya tetramera Huang for the first time, and they were identified with NMR and MS spectral analysis. It was confirmed that the new compound was 10-methoxy-7-methyl-2H-benzo[g]chromen-2-one (3) and the others were β-eudesmol (1), trans-3β-(1-hydroxy-1-methylethyl)-8aβ-methyl-5-methylenedecalin-2-one (2), 5,7-dimethoxy-8-[(Z)-3'-methyl-butan-1',3'-dienyl]coumarin (4), 7-geranyloxy-6-methoxycoumarin (5), 5,7-dimethoxy-8-(3-methyl-2-oxo-butyl)coumarin (6), murrangatin acetate (7) and toddalenone (8). Furthermore, the cytotoxic activity against human lung adenocarcinoma (A549), human hepatocellular carcinoma cells (SMMC-7721), human bladder tumor cells (EJ), human cervical carcinoma cells (HeLa), and human B-lineage acute lymphoblastic leukemia 1 cells (BALL-1) was evaluated for all compounds. It was found that five of them displayed various degrees of cytotoxicity against different testing targets. Compound 1 showed significant cytotoxic activity against the five cell lines (A549, SMMC-7721, EJ, Hela and BALL-1). Compounds 2 and 5 showed significant cytotoxicity against three cell lines (A549, SMMC-7721 and BALL-1). Compound 4 showed significant cytotoxicity against three cell lines (A549, EJ and BALL-1). However, compound 3 only showed fair cytotoxicity against the BALL-1 cell line. The structure-active relationships were investigated as well. These active compounds might be potential lead compounds for the treatment of cancer.