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DOI: 10.1055/s-2003-37716
Coumarins and Carbazoles from Clausena excavata Exhibited Antimycobacterial and Antifungal Activities
Publikationsverlauf
Received: June 4, 2002
Accepted: October 27, 2002
Publikationsdatum:
07. März 2003 (online)
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Abstract
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 μg/mL, respectively. O-Methylated clausenidin (4), prepared from 3, exhibited antimycobacterial activity at MIC 50 μg/mL. Compounds 6, 7, 8 and 10 showed antifungal activity with IC50 values of 13.6, 29.3, 9.5 and 2.8 μg/mL, respectively. All compounds demonstrated no cytotoxicity against KB and BC-1 cell lines.
References
- 1 Wu C C, Ko F N, Wu T S, Teng C M. Antiplatelet effects of clausine-D isolated from Clausena excavata . Biochimica et Biophysica Acta. 1994; 1201 1-6
- 2 Yenjai C, Sripontan S, Sriprajun P, Kittakoop P, Jintasirikul A, Tanticharoen M, Thebtaranonth Y. Coumarins and carbazoles with antiplasmodial activity from Clausena harmandiana . Planta Medica. 2000; 66 277-9
- 3 Wu T S, Furukawa H. Biological and phytochemical investigation of Clausena excavata . Journal of Natural Products. 1982; 45 718-20
- 4 Chakraborty A, Saha C, Podder G, Chowdhury B K, Bhattacharyya P. Carbazole alkaloid with antimicrobial activity from Clausena heptaphylla . Phytochemistry. 1995; 38 787-9
- 5 Ito C, Katsuno S, Itoigawa M, Ruangrungsi N, Mukainaka T, Okuda M, Kitakawa Y, Tokuda H, Nishino H, Furukawa H. New carbazole alkaloids from Clausena anisata with antitumor promoting activity. Journal of Natural Products. 2000; 63 125-8
- 6 Ito C, Itoigawa M, Katsuno S, Omura M, Tokuda H, Nishino H, Furukawa H. Chemical constituents of Clausena excavata: Isolation and structure elucidation of novel furanone-coumarins with inhibitory effects for tumor-promoting. Journal of Natural Products. 2000; 63 1218-24
- 7 Hirata K, Ito C, Furukawa H, Itoigawa M, Cosentino L M, Lee K -H. Substituted 7H-pyrido[4,3-c]carbazoles with potent anti-HIV activity. Bioorganic and Medicinal Chemistry Letters. 1999; 9 119-22
- 8 Wu T S, Furukawa H. Acridone alkaloids. VII. Constituents of Citrus sinensis Osbeck var. brasiliensis Tanaka. Isolation and characterization of three new acridone alkaloids, and a new coumarin. Chemical and Pharmaceutical Bulletin. 1983; 31 901-6
- 9 Huang S C, Wu P L, Wu T S. Two coumarins from the root bark of Clausena excavata . Phytochemistry. 1997; 44 179-81
- 10 Jash S S, Biswas G K, Bhattacharyya S K, Bhattacharyya P, Chakraborty A, Chowdhury B K. Carbazole Alkaloids from Glycosmis pentaphylla . Phytochemistry. 1992; 31 2503-5
- 11 Bhattacharyya P, Chakraborty A. Mukonal, a probable biogenetic intermediate of pyranocarbazole alkaloids from Murraya koenigii . Phytochemistry. 1984; 23 471-2
- 12 Li W S, McChesney J D, El-Feraly F S. Carbazole alkaloids from Clausena lansium . Phytochemistry. 1991; 30 343-6
- 13 Chaichantipyuth C, Pummangura S, Naowsaran K, Thanyavuthi D. Two new bioactive carbazole alkaloids from the root bark of Clausena harmandiana . Journal of Natural Products. 1988; 51 1285-8
- 14 Ito C, Katsuno S, Ohto H, Omura M, Kajiura I, Furukawa H. Constituents of Clausena excavata. Isolation and structural elucidation of new carbazole alkaloids. Chemical and Pharmaceutical Bulletin. 1997; 45 48-52
- 15 Collins L, Franzblau S G. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium . Antimicrobial Agents and Chemotherapy. 1997; 4 1004-9
- 16 Scudiero D A, Shoemaker R H, Paull K D, Monks A, Tierney S, Nofziger T H,. et al . Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Research. 1988; 48 4827-33
- 17 Skehan P, Storeng R, Scudiero D, Monks A, McMohon J D, Vistica D ,. et al . New colorimetric cytotoxicity assay for anticancer-drug screening. Journal of National Cancer Institute. 1990; 82 1107-12
Associate Professor Dr. Ngampong Kongkathip
Department of Chemistry
Faculty of Science
Kasetsart University
Chatujak
Bangkok 10900
Thailand
eMail: fscinpk@ku.ac.th
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