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).