Lipidyl Pseudopteranes A-F: Isolation, Biomimetic Synthesis, and PTP1B Inhibitory Activity...

J. Nat. Prod., 2008, 71 (12), pp 1977–1982

Lipidyl Pseudopteranes A-F: Isolation, Biomimetic Synthesis, and PTP1B Inhibitory Activity of
a New Class of Pseudopteranoids from the Gorgonian Pseudopterogorgia acerosa

Abhijeet S. Kate,§,‡ Isabelle Aubry,† Michel L. Tremblay,† and Russell G. Kerr*,§
Department of Chemistry and Department of Biomedical Sciences, Atlantic Veterinary College, UniVersity of Prince Edward Island,
Charlottetown, Prince Edward Island, Canada C1A 4P3, Department of Chemistry and Biochemistry, Florida Atlantic UniVersity,
Boca Raton, Florida 33431, and McGill Cancer Centre and Department of Biochemistry, McGill UniVersity, Montreal, Quebec, Canada H3G 1Y6
ReceiVed August 28, 2008
 

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.