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Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand
Department of Microbiology, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China
* Author to whom correspondence should be addressed.
Received: 2 December 2008; in revised form: 19 December 2008 / Accepted: 23 December 2008 / Published: 29 December 2008
Abstract: The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028, (±)-norannuradhapurine inhibits the production of NO, PGE2, TNF-a, IL-1b and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro.
Keywords: Alkaloid; Anti-inflammatory Activity; Aporphine; Isoquinoline; Synthesis; Radical Cyclization
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Nimgirawath, S.; Lorpitthaya, R.; Wanbanjob, A.; Taechowisan, T.; Shen, Y.-M. Total Synthesis and the Biological Activities of (±)-Norannuradhapurine. Molecules 2009, 14, 89-101.
Nimgirawath S, Lorpitthaya R, Wanbanjob A, Taechowisan T, Shen Y-M. Total Synthesis and the Biological Activities of (±)-Norannuradhapurine. Molecules. 2009; 14(1):89-101.
Nimgirawath, Surachai; Lorpitthaya, Rujee; Wanbanjob, Asawin; Taechowisan, Thongchai; Shen, Yue-Mao. 2009. "Total Synthesis and the Biological Activities of (±)-Norannuradhapurine." Molecules 14, no. 1: 89-101.