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Molecules 2009, 14(1), 89-101; doi:10.3390/molecules14010089
Article

Total Synthesis and the Biological Activities of (±)-Norannuradhapurine

1,* , 1
,
1
,
2
 and
3
1 Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand 2 Department of Microbiology, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand 3 Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China
* Author to whom correspondence should be addressed.
Received: 2 December 2008 / Revised: 19 December 2008 / Accepted: 23 December 2008 / Published: 29 December 2008
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
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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 Alkaloid; Anti-inflammatory Activity; Aporphine; Isoquinoline; Synthesis; Radical Cyclization
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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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.

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