Total synthesis and antimicrobial activity of +/--laurelliptinhexadecan-1-one and +/--laurelliptinoctadecan-1-one.
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.
Nimgirawath
Surachai
S
Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom, Thailand. surachai@su.ac.th
Udomputtimekakul
Phansuang
P
Pongphuttichai
Samathi
S
Wanbanjob
Asawin
A
Taechowisan
Thongchai
T
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D045744:Cell Line, Tumor; D031605:Cocculus / Q000737:chemistry; D004926:Escherichia coli / Q000187:drug effects; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism
D000890:Anti-Infective Agents; D006576:Heterocyclic Compounds, 4 or More Rings; C534176:laurelliptinhexadecan-1-one; C534177:laurelliptinoctadecan-1-one