Total synthesis and antimicrobial activity of +/--laurelliptinhexadecan-1-one and +/--laurelliptinoctadecan-1-one

• Published in: Molecules (Basel, Switzerland) Vol. 13; no. 12; pp. 2935 - 2947
• Main Authors: Nimgirawath, Surachai, Udomputtimekakul, Phansuang, Pongphuttichai, Samathi, Wanbanjob, Asawin, Taechowisan, Thongchai
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 28.11.2008; MDPI
• Subjects: Alkaloid; Amidic aporphine; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antimicrobial activity; Antimicrobial agents; Candida albicans - drug effects; Cell Line, Tumor; Chloride; Cocculus - chemistry; E coli; Escherichia coli - drug effects; Heterocyclic Compounds, 4 or More Rings - chemical synthesis; Heterocyclic Compounds, 4 or More Rings - chemistry; Heterocyclic Compounds, 4 or More Rings - pharmacology; Humans; Isoquinoline; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Molecular Structure; Spectrophotometry, Ultraviolet; Staphylococcus aureus - drug effects; Stereoisomerism; Synthesis; Thailand
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules13122935

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.