Absolute Configuration of a Hydroxyfuranoid Acid from the Pelage of the Genus Bos, 18-(6S,9R,10R)-Bovidic Acid

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2004-08, Vol.67 (8), p.1426-1430
• Main Authors: Ishii, Hideki, Krane, Sonja, Itagaki, Yasuhiro, Berova, Nina, Nakanishi, Koji, Weldon, Paul J
• Format: Article
• Language: English
• Subjects: Analytical, structural and metabolic biochemistry; Animals; Aromatic and heterocyclic compounds; Biological and medical sciences; Cattle; Circular Dichroism; Fundamental and applied biological sciences. Psychology; Hair - chemistry; Heterocyclic compounds, pigments; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Other biological molecules; Sheep; Stearic Acids - chemistry; Stearic Acids - isolation & purification; Stereoisomerism
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np049937u

Pelage extracts of the banteng (Bos javanicus), the domestic cattle (B. taurus), the gaur (B. frontalis), and the yak (B. grunniens) were investigated by FABMS and NMR. An 18-carbon hydroxyfuranoid acid, 1 (10-hydroxy-6,9-oxidooctadecanoic acid), first reported from the wool of the domestic sheep (Ovis aries) was confirmed in B. frontalis; we suspend judgment on the occurrence of this compound in the other species we examined. The stereochemistry of 1, determined by Mosher NMR and CD tweezer methods, was assigned as 6S, 9R, 10R. We propose the name bovidic acid for this and homologous α-hydroxylated 2,5-tetrahydrofuranoid carboxylic acids, in reference to the family Bovidae, which represents their sole known natural source.