Lipidyl pseudopteranes A-F: isolation, biomimetic synthesis, and PTP1B inhibitory activity of a new class of pseudopteranoids from the Gorgonian Pseudopterogorgia acerosa.
Novel lipidyl pseudopteranoids, lipidyl pseudopteranes A-F (1-6), have been isolated from the soft coral Pseudopterogorgia acerosa collected from the Bahamas. Structure elucidation of the six new compounds was based on 1D and 2D NMR data and mass spectrometry, and a biomimetic synthesis of 1 from pseudopterolide (7) was used to help establish its absolute configuration. These structures represent the first report of a pseudopterane diterpene with a fatty acid moiety. Lipidyl pseudopteranes A and D exhibited modest yet selective inhibitory activity against protein tyrosine phosphatase 1B, a promising drug target.
Kate
Abhijeet S
AS
Department of Chemistry and Department of Biomedical Sciences, Atlantic Veterinary College, University of Prince Edward Island, Charlottetown, Prince Edward Island, Canada C1A4P3.
Aubry
Isabelle
I
Tremblay
Michel L
ML
Kerr
Russell G
RG
D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D004195:Disease Models, Animal; D004224:Diterpenes / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D005227:Fatty Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors*
D004224:Diterpenes; D004791:Enzyme Inhibitors; D005227:Fatty Acids; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1