Molecules 2009, 14(2), 726-737; doi:10.3390/molecules14020726
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,* email, Phansuang Udomputtimekakul 1 email, Thitima Apornpisarn 1 email, Asawin Wanbanjob 1  and Thongchai Taechowisan 2 email
1 Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand 2 Department of Microbiology, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand
* Author to whom correspondence should be addressed.
Received: 12 January 2009; in revised form: 9 February 2009 / Accepted: 12 February 2009 / Published: 12 February 2009
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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

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MDPI and ACS Style

Nimgirawath, S.; Udomputtimekakul, P.; Apornpisarn, T.; Wanbanjob, A.; Taechowisan, T. 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, 14, 726-737.

AMA Style

Nimgirawath S, Udomputtimekakul P, Apornpisarn T, Wanbanjob A, Taechowisan T. 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; 14(2):726-737.

Chicago/Turabian Style

Nimgirawath, Surachai; Udomputtimekakul, Phansuang; Apornpisarn, Thitima; Wanbanjob, Asawin; Taechowisan, Thongchai. 2009. "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 14, no. 2: 726-737.

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