10.1021/np030242n.s002 Bingnan Han Bingnan Han Kerry L. McPhail Kerry L. McPhail Alessia Ligresti Alessia Ligresti Vincenzo Di Marzo Vincenzo Di Marzo William H. Gerwick William H. Gerwick Semiplenamides A−G, Fatty Acid Amides from a Papua New Guinea Collection of the Marine Cyanobacterium <i>Lyngbya </i><i>s</i><i>emiplena</i> American Chemical Society 2003 alcohol moieties Marine Cyanobacterium Lyngbya affinity chemical derivatization Amide GC rat cannabinoid CB 1 receptor metabolite AMT series aliphatic portion 1997 Papua New Guinea collection experiment lipid brine shrimp model system anandamide membrane transporter chiral toxicity marine cyanobacterium Lyngbya semiplena 2 D NMR methods 1 D NOE data acid amides 1 D inhibitor IC 50 Fatty Papua New Guinea Collection stereochemistry semiplenamide emiplena Semiplenamides 18.1 μ M 2003-10-24 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Semiplenamides_A_G_Fatty_Acid_Amides_from_a_Papua_New_Guinea_Collection_of_the_Marine_Cyanobacterium_i_Lyngbya_i_i_s_i_i_emiplena_i_/3361294 Semiplenamides A (<b>1</b>) to G (<b>7</b>), a series of new anandamide-like fatty acid amides, were isolated from a 1997 Papua New Guinea collection of the marine cyanobacterium <i>Lyngbya semiplena</i>. 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 <sup>1</sup>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<sub>1</sub> receptor and semiplenamide A was a moderate inhibitor (IC<sub>50</sub> = 18.1 μM) of the anandamide membrane transporter (AMT).