Title
Absolute configuration of a hydroxyfuranoid acid from the pelage of the genus Bos, 18-(6S,9R,10R)-bovidic acid
Author(s)
Ishii, H; Krane, S; Itagaki, Y; Berova, N; Nakanishi, K; Weldon, PJ
Published
2004
Publisher
Journal of Natural Products
Abstract
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 alpha-hydroxylated 2,5-tetrahydrofuranoid carboxylic acids, in reference to the family Bovidae, which represents their sole known natural source.
Keywords
SKIN SURFACE-LIPIDS; ZINC PORPHYRIN HOST; CHIRAL RECOGNITION; REAGENTS; ALCOHOL; CATTLE
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