Total synthesis and the biological activities of (+/-)-norannuradhapurine.
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.
Nimgirawath
Surachai
S
Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand. surachai@su.ac.th
Lorpitthaya
Rujee
R
Wanbanjob
Asawin
A
Taechowisan
Thongchai
T
Shen
Yue-Mao
YM
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001060:Aporphines / Q000138:chemical synthesis* / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D002460:Cell Line; D003500:Cyclization; D051546:Cyclooxygenase 2 / Q000187:drug effects; D015232:Dinoprostone / Q000037:antagonists & inhibitors; D004926:Escherichia coli / Q000187:drug effects; D053583:Interleukin-1beta / Q000037:antagonists & inhibitors; D008070:Lipopolysaccharides / Q000276:immunology / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000276:immunology; D019684:Magnoliopsida / Q000737:chemistry; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors; D013211:Staphylococcus aureus / Q000187:drug effects; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors; D000093242:Interleukin-6 Inhibitors
D000893:Anti-Inflammatory Agents; D001060:Aporphines; D051546:Cyclooxygenase 2; D015232:Dinoprostone; D053583:Interleukin-1beta; D008070:Lipopolysaccharides; D009569:Nitric Oxide; D052247:Nitric Oxide Synthase Type II; D014409:Tumor Necrosis Factor-alpha; D000093242:Interleukin-6 Inhibitors; C534561:norannuradhapurine; C077623:Ptgs2 protein, mouse