Han Bingnan, McPhail Kerry L, Ligresti Alessia, Di Marzo Vincenzo, Gerwick William H
College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA.
J Nat Prod. 2003 Oct;66(10):1364-8. doi: 10.1021/np030242n.
Semiplenamides A (1) to G (7), a series of new anandamide-like fatty acid amides, were isolated from a 1997 Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena. The planar structures of these lipids were determined using standard 1D and 2D NMR methods. The relative stereochemistry of the aliphatic portion of the new metabolites was deduced from 1D NOE data and (1)H-decoupling experiments, while the absolute stereochemistry of the amino alcohol moieties was assigned by chemical derivatization and chiral GC-MS methods. All of these new metabolites displayed toxicity in the brine shrimp model system, while semiplenamides A, B, and G showed weak affinity for the rat cannabinoid CB(1) receptor and semiplenamide A was a moderate inhibitor (IC(50) = 18.1 muM) of the anandamide membrane transporter (AMT).
从1997年采集自巴布亚新几内亚的海洋蓝藻半丰满鞘丝藻（Lyngbya semiplena）中分离出了一系列新的类花生四烯酸脂肪酸酰胺——半丰满酰胺A（1）至G（7）。这些脂质的平面结构通过标准的一维和二维核磁共振方法确定。新代谢产物脂肪族部分的相对立体化学结构由一维核Overhauser效应（NOE）数据和氢去耦实验推导得出，而氨基醇部分的绝对立体化学结构则通过化学衍生化和手性气相色谱 - 质谱方法确定。所有这些新代谢产物在卤虫模型系统中均表现出毒性，同时半丰满酰胺A、B和G对大鼠大麻素CB(1)受体显示出弱亲和力，且半丰满酰胺A是一种中等强度的花生四烯酸乙醇胺膜转运体（AMT）抑制剂（IC(50) = 18.1 μM）。
