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Authors = Asawin Wanbanjob

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12 pages, 114 KiB  
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
by Surachai Nimgirawath, Phansuang Udomputtimekakul, Thitima Apornpisarn, Asawin Wanbanjob and Thongchai Taechowisan
Molecules 2009, 14(2), 726-737; https://doi.org/10.3390/molecules14020726 - 12 Feb 2009
Cited by 3 | Viewed by 9564
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 13 [...] Read more.
(±)-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. Full article
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13 pages, 114 KiB  
Article
Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
by Surachai Nimgirawath, Rujee Lorpitthaya, Asawin Wanbanjob, Thongchai Taechowisan and Yue-Mao Shen
Molecules 2009, 14(1), 89-101; https://doi.org/10.3390/molecules14010089 - 29 Dec 2008
Cited by 7 | Viewed by 11724
Abstract
The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, [...] Read more.
The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028, (±)-norannuradhapurine inhibits the production of NO, PGE2, TNF-a, IL-1b and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
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13 pages, 136 KiB  
Article
Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
by Surachai Nimgirawath, Phansuang Udomputtimekakul, Samathi Pongphuttichai, Asawin Wanbanjob and Thongchai Taechowisan
Molecules 2008, 13(12), 2935-2947; https://doi.org/10.3390/molecules13122935 - 28 Nov 2008
Cited by 3 | Viewed by 9418
Abstract
The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated [...] Read more.
The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated cyclisation. Both (±)-laurelliptinhexadecan-1-one (1a) and (±)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
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