Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine

Molecules

Surachai Nimgirawath¹  Phansuang Udomputtimekakul¹  Thitima Apornpisarn¹  Asawin Wanbanjob¹ 

[1] Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand; E-mails:

关键词: Alkaloid;    Protoberberine;    Isoquinoline;    Synthesis;    Antimicrobial activity.;   

DOI  :  10.3390/molecules14020726

来源: mdpi

【 摘 要 】

(±)-Gusanlung A, 8-oxyberberrubine and (±)-gusanlung D have been synthesized by radical cyclisation of the corresponding 2-aroyl-1-methylenetetra- hydroisoquinolines. The ¹H and ¹³C spectra of (-)-gusanlung D were found to be different from those of synthetic (±)-gusanlung D. Careful analyses of the ¹³C 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.

【 授权许可】

CC BY   
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.