Total synthesis and the biological activities of (+/-)-norannuradhapurine
Surachai Nimgirawath1, Rujee Lorpitthaya, Asawin Wanbanjob
1Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand. surachai@su.ac.th
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, PGE(2), TNF-alpha, IL-1beta and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro.
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