{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T09:48:11Z","timestamp":1791107291179,"version":"4.1.0"},"reference-count":32,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2011,11,21]],"date-time":"2011-11-21T00:00:00Z","timestamp":1321833600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A total of three carbazole alkaloids and essential oil from the leaves of Murraya koenigii (Rutaceae) were obtained and examined for their effects on the growth of five antibiotic resistant pathogenic bacteria and three tumor cell lines (MCF-7, P 388 and Hela). The structures of these carbazoles were elucidated based on spectroscopy data and compared with literature data, hence, were identified as mahanine (1), mahanimbicine (2) and mahanimbine (3). The chemical constituents of the essential oil were identified using Gas Chromatography-Mass Spectroscopy (GCMS). These compounds exhibited potent inhibition against antibiotic resistant bacteria such as Staphylococcus aureus (210P JTU), Psedomonas aeruginosa (ATCC 25619), Klebsiella pneumonia (SR1-TU), Escherchia coli (NI23 JTU) and Streptococcus pneumoniae (SR16677-PRSP) with significant minimum inhibition concentration (MIC) values (25.0\u2013175.0 mg\/mL) and minimum bacteriacidal concentrations (MBC) (100.0\u2013500.0 mg\/mL). The isolated compounds showed significant antitumor activity against MCF-7, Hela and P388 cell lines. Mahanimbine (3) and essential oil in particular showed potent antibacteria and cytotoxic effect with dose dependent trends (\u22645.0 \u03bcg\/mL). The findings from this investigation are the first report of carbazole alkaloids\u2019 potential against antibiotic resistant clinical bacteria, MCF-7 and P388 cell lines.<\/jats:p>","DOI":"10.3390\/molecules16119651","type":"journal-article","created":{"date-parts":[[2011,11,21]],"date-time":"2011-11-21T11:07:05Z","timestamp":1321873625000},"page":"9651-9664","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":109,"title":["Biological Activity of Carbazole Alkaloids and Essential Oil of Murraya koenigii Against Antibiotic Resistant Microbes and Cancer Cell Lines"],"prefix":"10.3390","volume":"16","author":[{"given":"Thilahgavani","family":"Nagappan","sequence":"first","affiliation":[{"name":"Laboratory of Natural Products Chemistry, Institute for Tropical Biology and Conservation, Universiti Malaysia Sabah, 88999 Kota Kinabalu, Sabah, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Perumal","family":"Ramasamy","sequence":"additional","affiliation":[{"name":"School of Medicine, Universiti Malaysia Sabah, 88999 Kota Kinabalu, Sabah, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohd Effendy Abdul","family":"Wahid","sequence":"additional","affiliation":[{"name":"Institute of Marine Biotechnology, University Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thirukanthan Chandra","family":"Segaran","sequence":"additional","affiliation":[{"name":"Institute of Marine Biotechnology, University Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7453-1718","authenticated-orcid":false,"given":"Charles S.","family":"Vairappan","sequence":"additional","affiliation":[{"name":"Laboratory of Natural Products Chemistry, Institute for Tropical Biology and Conservation, Universiti Malaysia Sabah, 88999 Kota Kinabalu, Sabah, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2011,11,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"926","DOI":"10.1016\/j.phymed.2010.03.004","article-title":"Antimicrobial, antiviral and cytotoxic activity of extracts and constituents from Polygonum spectabile Mart","volume":"17","author":"Brandao","year":"2010","journal-title":"Phytomedicine"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"846","DOI":"10.1016\/j.phymed.2007.09.004","article-title":"Benzobijuglone, a novel cytotoxic compound from Juglans mandshurica induced apoptosis in HeLa cervical cancer cells","volume":"14","author":"Li","year":"2007","journal-title":"Phytomedicine"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2694","DOI":"10.1016\/j.fct.2008.04.024","article-title":"(\u2212)-Anonaine induces apoptosis through Bax- and caspase-dependent pathways in human cervival cancer (HeLa) cells","volume":"46","author":"Chen","year":"2008","journal-title":"Food Toxicol. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1881","DOI":"10.1016\/j.bmcl.2010.01.159","article-title":"Synthesis, antibacterial and antifungal activities of some carbazole derivatives","volume":"20","author":"Zhang","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_5","first-page":"2685","article-title":"Working group on the registration and monitoring of cervical cancer screening programmes in the European Union within the European Network for Information on Cancer (EUNICE). Description of the national situation of cervical cancer screening in the member states of the European Union","volume":"45","author":"Antilla","year":"2009","journal-title":"Eur. J. Cancer"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4","DOI":"10.1016\/S0959-8049(01)00267-2","article-title":"Cancer burden in the year 2000: The global picture","volume":"37","author":"Parkin","year":"2001","journal-title":"Eur. J. Cancer"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"4570","DOI":"10.1016\/j.bmcl.2009.06.098","article-title":"Synthesis and evaluation of novel substituted 5-hydroxycoumarin and pyranocoumarin derivatives exhibiting significant antiproliferative activity against breast cancer cell lines","volume":"19","author":"Mao","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3259","DOI":"10.1016\/j.bmcl.2010.04.061","article-title":"Synthesis of new cis-fused tetrahydrochromeno [4,3-b]quinolines and their antiproliferative activity studies against MDA-MB-231 and MCF-7 breast cancer cell lines","volume":"20","author":"Nagaiah","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1016\/j.bcp.2009.09.007","article-title":"Apoptotic effects of mahanine on human leukemic cells are mediated through crosstalk between Apo-1\/Fas signaling and the Bid protein and via mitochondrial pathways","volume":"79","author":"Bhattacharya","year":"2010","journal-title":"Biochem. Pharmacol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/j.bcp.2003.07.021","article-title":"Mechanism of mahanine-induced apoptosis in human leukemia cells (HL-60)","volume":"67","author":"Roy","year":"2004","journal-title":"Biochem. Pharmacol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1016\/j.foodchem.2005.09.078","article-title":"Antibacterial activity of the essential oils of Salvia officinalis L. and Salvia triloba L. cultivated in South Brazil","volume":"100","author":"Delamare","year":"2007","journal-title":"Food Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"567","DOI":"10.1016\/j.phytochem.2004.12.030","article-title":"Chemical constituents of Murraya siamensis: Three coumarins and their anti-tumor promoting effect","volume":"66","author":"Ito","year":"2005","journal-title":"Phytochemistry"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"212","DOI":"10.1016\/j.bbrc.2007.08.005","article-title":"Mahanine reverses an epigenetically silenced tumor suppressor gene RASSF1A in human prostate cancer cells","volume":"362","author":"Jagadeesh","year":"2007","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1016\/j.etp.2010.04.012","article-title":"Hepatoprotective effects of aqueous leaf extract and crude isolates of Murraya koenigii against in vitro ethanol-induced hepatotoxicity model","volume":"63","author":"Sathaye","year":"2011","journal-title":"Exp. Toxicol. Pathol."},{"key":"ref_15","unstructured":"Cordell, G.A. (2008). The Alkaloids: Chemistry and Biology, Academic Press."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5589","DOI":"10.1021\/jf010621r","article-title":"Antioxidative activity of carbazoles from Murraya koenigii leaves","volume":"45","author":"Tachibana","year":"2001","journal-title":"J. Agric. Food Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"444","DOI":"10.1021\/jf9805808","article-title":"Biologically active carbazole alkaloids from Murraya koenigii","volume":"47","author":"Ramsewak","year":"1999","journal-title":"J. Agric. Food Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1601","DOI":"10.1016\/j.phytochem.2005.05.001","article-title":"A benzoisofuranone derivative and carbazole alkaloids from Murraya koenigii and their antimicrobial","volume":"66","author":"Rahman","year":"2005","journal-title":"Phytochemistry"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1016\/0031-9422(96)00361-5","article-title":"Seasonal variations of carbazole alkaloids in Murraya euchrestifolia","volume":"43","author":"Wu","year":"1996","journal-title":"Phytochemistry"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1245","DOI":"10.1016\/j.bmcl.2008.12.077","article-title":"Synthesis and SAR of vinca alkaloids analogues","volume":"19","author":"Voss","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"246","DOI":"10.1016\/j.phymed.2004.12.002","article-title":"Anti-trichomonal, biochemical and toxicological activities of methanolic extract and some carbazole alkaloids isolated from the leaves of Murraya koenigii growing in Nigeria","volume":"13","author":"Adebajo","year":"2006","journal-title":"Phytomedicine"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3413","DOI":"10.1016\/S0968-0896(03)00308-0","article-title":"Synthesis and cytotoxic activity of different open indocarbazole alkaloid analogues","volume":"11","author":"Caballero","year":"2003","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"309","DOI":"10.2174\/1570179043366594","article-title":"Transition metal complexes in organic synthesis. Part 70. Synthesis of biologically active carbazole alkaloids using organometallic chemistry","volume":"1","author":"Knolker","year":"2004","journal-title":"Curr. Org. Synth."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1881","DOI":"10.1016\/j.bmcl.2010.01.159","article-title":"Synthesis, antibacterial and antifungal activities of some carbazole derivatives","volume":"20","author":"Zhang","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4303","DOI":"10.1021\/cr020059j","article-title":"Isolation and synthesis of biologically active carbazole alkaloids","volume":"102","author":"Knolker","year":"2002","journal-title":"Chem. Rev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"114","DOI":"10.1016\/j.canlet.2005.04.021","article-title":"Anti-proliferative activity of essential oil extracted from Thai medicinal plants on KB and P388 cell lines","volume":"235","author":"Manosroi","year":"2006","journal-title":"Cancer Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1016\/j.jep.2009.08.034","article-title":"Essential oils of Salvia bracteata and Salvia rubifolia from Lebanon: Chemical composition, antimicrobial activity and inhibitory effect on human melanoma cells","volume":"126","author":"Cardile","year":"2009","journal-title":"J. Ethnopharmacol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"971","DOI":"10.1016\/S0031-9422(00)90474-6","article-title":"Terpenoids from Salvia sclarea","volume":"36","author":"Ulubelen","year":"1994","journal-title":"Phytochemistry"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2755","DOI":"10.1016\/j.fct.2009.08.005","article-title":"Disinfect properties of essential oils from Salvia officinalis L. cultivated in Tunisia","volume":"47","author":"Bouaziz","year":"2009","journal-title":"Food Chem. Toxicol."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"681","DOI":"10.1016\/j.foodcont.2007.07.007","article-title":"Antimicrobial activity and chemical composition of Thymus vulgaris, Thymus zygis and Thymus hyemalis essential oils","volume":"19","author":"Rota","year":"2008","journal-title":"Food Control"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"823","DOI":"10.1016\/j.foodchem.2006.09.032","article-title":"Antimicrobial activity of the essential oils of Brazilian species of the genus Cunila against foodborne pathogens and spoiling bacteria","volume":"103","author":"Sandri","year":"2007","journal-title":"Food Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1016\/j.foodchem.2005.09.078","article-title":"Antibacterial activity of the essential oils of Salvia officinalis L. and Salvia triloba L. cultivated in South Brazil","volume":"100","author":"Delamare","year":"2007","journal-title":"Food Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/16\/11\/9651\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:58:04Z","timestamp":1760219884000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/16\/11\/9651"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,11,21]]},"references-count":32,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2011,11]]}},"alternative-id":["molecules16119651"],"URL":"https:\/\/doi.org\/10.3390\/molecules16119651","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,11,21]]}}}