Total syntheses of (+/-)-gusanlung a, (+/-)-gusanlung D and 8-oxyberberrubine and the uncertainty concerning the structures of (-)-gusanlung A, (-)-gusanlung D and 8-oxyberberrubine.
(+/-)-Gusanlung A, 8-oxyberberrubine and (+/-)-gusanlung D have been synthesized by radical cyclisation of the corresponding 2-aroyl-1-methylenetetra- hydroisoquinolines. The (1)H and (13)C spectra of (-)-gusanlung D were found to be different from those of synthetic (+/-)-gusanlung D. Careful analyses of the (13)C spectra of (-)-gusanlung A and natural 8-oxyberberrubine also cast doubt on the correctness of the structures previously assigned to these two compounds. (+/-)-Gusanlung A and (+/-)-gusanlung D were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028.
Nimgirawath
Surachai
S
Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand. surachai@su.ac.th
Udomputtimekakul
Phansuang
P
Apornpisarn
Thitima
T
Wanbanjob
Asawin
A
Taechowisan
Thongchai
T
D001599:Berberine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D004365:Drugs, Chinese Herbal / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013211:Staphylococcus aureus / Q000187:drug effects
D004365:Drugs, Chinese Herbal; C539478:gusanlung D; D001599:Berberine; C073424:gusanlung A; C115958:berberrubine