3-Formylcarbazole

[Chemical constituents from stems and leaves of Clausena emarginata].[Pubmed:31355567]

Zhongguo Zhong Yao Za Zhi. 2019 May;44(10):2096-2101.

The chemical constituents from the stems and leaves of Clausena emarginata were separated and purified by column chromatographies on silica gel,ODS,Sephadex LH-20,and PR-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic analysis,as well as comparisons with the data reported in the literature. Sixteen compounds were isolated from the 90% ethanol extract of the stems and leaves of C. emarginata,which were identified as siamenol( 1),murrastanine A( 2),3-formyl-1,6-dimethoxycarbazole( 3),3-methoxymethylcarbazole( 4),3-methylcarbazole( 5),murrayafoline A( 6),3-Formylcarbazole( 7),3-formyl-1-hydroxycarbazole( 8),3-formyl-6-methoxycarbazole( 9),murrayanine( 10),murrayacine( 11),girinimbine( 12),nordentatin( 13),chalepin( 14),8-hydroxy-6-methoxy-3-pentylisocoumarin( 15) and ethyl orsellinate( 16). Compounds 1-4,14-16 were isolated from C. emarginata for the first time. Among them,compounds 1,2,15 and 16 were isolated from the genus Clausena for the first time. All isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines: HL-60,SMMC-7721,A-549,MCF-7 and SW480 in vitro. Compounds 12 and 14 showed significant inhibitory effects against various human cancer cell lines with IC_(50) values comparable to those of doxorubicin.

[Chemical constituents from stems of Clausena excavata].[Pubmed:26027123]

Zhong Yao Cai. 2014 Nov;37(11):2012-5.

OBJECTIVE: To study the chemical constituents from the stems of Clausena excavata. METHODS: The constituents were isolated by various chromatographic techniques(silica gel, RP-MPLC and PHPLC) and their structures were determined on the basis of their spectroscopic data, as well as literatures. RESULTS: Eleven compounds were separated and identified as adicardin(1),7-[O-alpha-L-rh-amnopyranosyl-(1-->6)-O-beta-D-glucopyranosyloxy]cou marin(2), 6-methoxy-7-[O-alpha-L-rhamnopyranosyl-(1-->6)-O-beta-D-glucopyranosyloxy] coumarin (3), alloisoimperatorin (4), isopentenoyloxypsoralen (5), nordentatin (6), xanthyletin (7), 7-hydroxycoumarin (8), 3-Formylcarbazole(9), 3-formyl-6-methoxy carbazole(10), and murrayanine(11). CONCLUSION: compounds 2-4 and 10 are isolated from this plant for the first time, and compounds 1 and 5 are isolated from Clausena genus for the first time.

Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark: anti-trichomonal, antidiabetic, anti-inflammatory, hepatoprotective and antioxidant effects.[Pubmed:19095054]

J Ethnopharmacol. 2009 Feb 25;122(1):10-9.

ETHNOPHARMACOLOGICAL RELEVANCE: Clausena lansium (Fool's Curry Leaf) is used for various ethnomedical conditions in some countries, including bronchitis, malaria, viral hepatitis, acute and chronic gastro-intestinal inflammation, and as a spicy substitute of the popular Curry leaf tree (Murraya koenigii). AIM OF THE STUDY: This study was to evaluate the ethnomedical uses of the stem bark in inflammatory conditions, hepatotoxicity and to determine the anti-diabetic and anti-trichomonal properties of the plant. MATERIALS AND METHOD: Anti-trichomonal, in vivo and in vitro antidiabetic and insulin stimulating, anti-inflammatory, hepatoprotective and anti-oxidant activities using Trichomonas gallinae, glucose loaded rats and in vitro insulin secreting cell line (INS-1 cell), carrageenin-induced rat paw oedema, CCl(4)-induced hepatotoxicity and DPPH scavenging ability methods respectively for the extracts and some isolates were determined. RESULTS: A dichloromethane extract was superior over methanolic extract with respect to an anti-trichomonal activity which was measured after 24 and 48 h. The isolated compounds imperatorin and 3-Formylcarbazole had the main anti-trichomonal activity (LC(50)s of 6.0, 3.0 and 3.6, 9.7 microg/mL after 24 and 48 h, respectively). Methanolic extract (100 mg/kg) induced maximum and significant (p<0.05) anti-hyperglycaemic activity of 15.8% at 30 min and a 38.5% increase in plasma insulin at 60 min, compared to control. The increase in plasma insulin after 60 min, compared to 0 min, was 62.0% (p<0.05). The significant 174.6% increase of insulin release from INS-1 cells (in vitro) at 0.1 mg/ml indicates that it mediates its antidiabetic action mainly by stimulating insulin release. Imperatorin and chalepin were the major active constituents increasing in vitro insulin release to 170.3 and 137.9%, respectively. 100 mg/kg of the methanolic extract produced an anti-inflammatory activity after 4 h. A sedative effect was not observed. 100 and 200 mg/kg of methanolic extract administered i.p., reduced CCl4-induced hepatotoxicity firstly by 5.3 and 8.4% reduction in phenobarbitone-sleeping time respectively, secondly by reversing the reduction in serum liver proteins by 7.0-8.8%, serum AST, ALT and ALP activities by 27.7-107.9% and thirdly by diminishing increased values of plasma AST, ALT and ALP activities by 13.2-83.8%. The extract exhibited antioxidant activities. CONCLUSION: The hepatoprotective activity of C. lansium is partly due to its anti-oxidant and anti-inflammatory properties and confirms its folkloric use in the treatment of gastro-intestinal inflammation, bronchitis and hepatitis. In addition the use of C. lansium stem bark would be useful in diabetes and trichomoniasis.

Anti-tuberculosis constituents from the stem bark of Micromelum hirsutum.[Pubmed:15770548]

Planta Med. 2005 Mar;71(3):261-7.

Anti-TB bioassay-directed fractionation led to the isolation of six carbazole alkaloids, as well as the gamma-lactone derivative of oleic acid, from the CH (2)Cl (2) extract of the stem bark of Micromelum hirsutum. The carbazoles include the new micromeline ( 2) and five known alkaloids: lansine ( 3), 3-methylcarbazole ( 4), methyl carbazole-3-carboxylate ( 5), 3-Formylcarbazole ( 6), and 3-formyl-6-methoxycarbazole ( 7). Compound 1 was identified as the lactone derivative of oleic acid, (-)- Z-9-octadecene-4-olide, for which the trivial name micromolide ( 1) is suggested. It showed potent in vitro anti-TB activity against H37R v (MIC: 1.5 microg/mL), a selectivity index (SI) of 63, and exhibited activity against the Erdman strain of M. tuberculosis in a J774 mouse macrophage model (EC (90) : 5.6 microg/mL). Thus, 1 appears worthy of further evaluation as a potential new anti-TB agent. Isolates 2, 3, 6 and 7 had anti-TB MIC values between 14.3 and 42.3 microg/mL, while compounds 4 and 5 were considered inactive (MIC > 128 microg/mL). Structure elucidation and identification were based on spectroscopic analysis, including MS, 1D/2D NMR, and a full (1)H spin system analysis of 1.

Coumarins and carbazoles from Clausena excavata exhibited antimycobacterial and antifungal activities.[Pubmed:12624822]

Planta Med. 2003 Feb;69(2):155-7.

Four known coumarins, dentatin (1), nor-dentatin (2), clausenidin (3) and xanthoxyletin (5), and six known carbazole derivatives, 3-Formylcarbazole (6), mukonal (7), 3-methoxycarbonylcarbazole (8), murrayanine (9), 2-hydroxy-3-formyl-7-methoxycarbazole (10) and clauszoline J (11) were isolated from Clausena excavata. Compounds 1 and 6 were first isolated from the crude chloroform extract of the rhizomes. Compounds 1, 2, 3, 6, 7, 8, 10 and 11 showed antimycobacterial activity at a minimum inhibitory concentration (MIC) of 50, 100, 200, 100, 200, 50, 100 and 100 microg/mL, respectively. O-Methylated clausenidin ( 4), prepared from 3, exhibited antimycobacterial activity at MIC 50 microg/mL. Compounds 6, 7, 8 and 10 showed antifungal activity with IC 50 values of 13.6, 29.3, 9.5 and 2.8 microg/mL, respectively. All compounds demonstrated no cytotoxicity against KB and BC-1 cell lines.

Carbazole alkaloid with antimicrobial activity from Clausena heptaphylla.[Pubmed:7766168]

Phytochemistry. 1995 Feb;38(3):787-9.

A new carbazole alkaloid designated as clausenal was isolated from the leaves of Clausena heptaphylla and its structure established as 1,8-dimethoxy-3-Formylcarbazole from physical, chemical and synthetic evidence. The alkaloid was found to be active against both Gram-positive and Gram-negative bacteria, and fungi.