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

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2008-12, Vol.71 (12), p.1977-1982
• Main Authors: Kate, Abhijeet S, Aubry, Isabelle, Tremblay, Michel L, Kerr, Russell G
• Format: Article
• Language: English
• Subjects: Animals; Anthozoa - chemistry; Biological and medical sciences; Disease Models, Animal; Diterpenes - chemistry; Diterpenes - classification; Diterpenes - isolation & purification; Diterpenes - pharmacology; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - isolation & purification; Enzyme Inhibitors - pharmacology; Fatty Acids - chemistry; Fatty Acids - isolation & purification; Fatty Acids - pharmacology; General pharmacology; Marine Biology; Medical sciences; Mice; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800544b

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.