Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine 英文参考文献.docVIP

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Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine 英文参考文献.doc

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Total Syntheses of (±)-Gusanlung A, (±)-Gusanlung D and 8-Oxyberberrubine and the Uncertainty Concerning the Structures of (-)-Gusanlung A, (-)-Gusanlung D and 8-Oxyberberrubine 英文参考文献

Molecules 2009, 14, 726-737; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article 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 1,*, Phansuang Udomputtimekakul 1, Thitima Apornpisarn 1, Asawin Wanbanjob 1 and Thongchai Taechowisan 2 1 Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand; E-mails: Phansuang@ (P.U.), winsusc@ (T.A.), thitima_noon@ (T.A.) 2 Department of Microbiology, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand; E-mail: tthongch@su.ac.th (T.T.) * Author to whom correspondence should be addressed; E-mail: surachai@su.ac.th Received: 12 January 2009; in revised form: 9 February 2009 / Accepted: 12 February 2009 / Published: 12 February 2009 Abstract: (±)-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. Keywords: Alkaloid; Protoberberine; Isoquinoline; Synthesis; Antimicrobial activity. Molecules 2009, 14 727 Introduction (–)-Gusanlung D, isolated from Acangelisia gusanlung H. S. Lo (Menispermaceae), is the first natural 8-oxotetrahydroprotoberberine alkaloid with an unoxygenated ring D [1]. Based on spectral data analysis, structure 1 wa