Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one 英文参考文献.docVIP

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Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one 英文参考文献.doc

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Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one 英文参考文献

Molecules 2008, 13, 2935-2947; DOI: 10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan- 1-one Surachai Nimgirawath1,*, Phansuang Udomputtimekakul 1, Samathi Pongphuttichai 1, Asawin Wanbanjob 1 and Thongchai Taechowisan 2 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; E-mail: tthongch@su.ac.th (T. T.) * Author to whom correspondence should be addressed; E-mail: surachai@su.ac.th. Received: 8 November 2008; in revised form: 19 November 2008 / Accepted: 25 November 2008/ Published: 28 November 2008 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 cyclisation. Both (±)-laurelliptinhexadecan-1-one (1a) and (±)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028. Keywords: Alkaloid; Amidic aporphine; Isoquinoline; Synthesis; Antimicrobial activity. Introduction Amidic aporphine alkaloids usually occur as N-formyl, N-acetyl and N-methoxycarbonyl derivatives [1]. (+)-Laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) are two unique amidic aporphine alkaloids in which a palmitoyl and a stearoyl functional group is attached to Molecules 2008, 13 2936 the nitrogen of the aporphine nucleus, respectively (Figure 1)[2]. Figure 1. Structures of (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan- 1-one (1b).