Total Synthesis and the Biological Activities of (±)-Norannuradhapurine 英文参考文献.docVIP

Molecules 2009, 14, 89-101; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Total Synthesis and the Biological Activities of (±)-Norannuradhapurine Surachai Nimgirawath 1,*, Rujee Lorpitthaya 1, Asawin Wanbanjob 1, Thongchai Taechowisan 2 and Yue-Mao Shen 3 1 Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand; E-mails: G050010@.sg (R. L.), winsusc@ (A. W.) 2 Department of Microbiology, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand; E-mail: tthongch@su.ac.th (T. T.) 3 Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China. E-mail: yshen@ (Y-M. C.) * Author to whom correspondence should be addressed; E-mail: surachai@su.ac.th. 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-α, IL-1β 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.  Molecules 2009, 14 90 Introduction (-)-Norannuradhapurine (1a) is a phenolic noraporphine alkaloid isolated for the first time from the bark and leaves of Polyalthia acuminate Thw. (Annonaceae) [1] and subsequently from the bark and wood of Fissistigma glaucescens (Hance) Merr. and the wood of Fissistigma oldhamii (Hemsl.) M