Total syntheses of (+/-)-gusanlung a, (+/-)-gusanlung D and 8-oxyberberrubine and the uncertainty concerning the structures of (-)-gusanlung A, (-)-gusanlung D and 8-oxyberberrubine

Surachai Nimgirawath; Phansuang Udomputtimekakul; Thitima Apornpisarn; Asawin Wanbanjob; Thongchai Taechowisan

doi:10.3390/molecules14020726

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. 2009 Feb 12;14(2):726-37. doi: 10.3390/molecules14020726.

Authors

Surachai Nimgirawath¹, Phansuang Udomputtimekakul, Thitima Apornpisarn, Asawin Wanbanjob, Thongchai Taechowisan

Affiliation

¹ Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand. surachai@su.ac.th

Abstract

(+/-)-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.

MeSH terms

Berberine / analogs & derivatives*
Berberine / chemical synthesis
Berberine / chemistry
Berberine / pharmacology
Candida albicans / drug effects
Drugs, Chinese Herbal / chemical synthesis*
Drugs, Chinese Herbal / chemistry*
Drugs, Chinese Herbal / pharmacology
Escherichia coli / drug effects
Microbial Sensitivity Tests
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Staphylococcus aureus / drug effects

Substances

Drugs, Chinese Herbal
gusanlung D
Berberine
gusanlung A
berberrubine