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Papers In Press, published online ahead of print February 1, 2010
J. Lipid Res., doi:10.1194/jlr.R000042

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Journal of Lipid Research, Vol. 51, 226-246, February 2010
Copyright © 2010 by American Society for Biochemistry and Molecular Biology

Thematic Review

Bile salts of vertebrates: structural variation and possible evolutionary significance^[S]

Alan F. Hofmann^1,*, Lee R. Hagey^* and Matthew D. Krasowski^2,

^* Department of Medicine, University of California, San Diego, San Diego, CA, 92093-0063
Department of Pathology, University of Pittsburgh, Pittsburgh, PA 15261

¹ To whom correspondence should be addressed. e-mail: ahofmann{at}ucsd.edu

Biliary bile salt composition of 677 vertebrate species (103 fish, 130 reptiles, 271 birds, 173 mammals) was determined. Bile salts were of three types: C₂₇ bile alcohols, C₂₇ bile acids, or C₂₄ bile acids, with default hydroxylation at C-3 and C-7. C₂₇ bile alcohols dominated in early evolving fish and amphibians; C₂₇ bile acids, in reptiles and early evolving birds. C₂₄ bile acids were present in all vertebrate classes, often with C₂₇ alcohols or with C₂₇ acids, indicating two evolutionary pathways from C₂₇ bile alcohols to C₂₄ bile acids: a) a ‘direct’ pathway and b) an ‘indirect’ pathway with C₂₇ bile acids as intermediates. Hydroxylation at C-12 occurred in all orders and at C-16 in snakes and birds. Minor hydroxylation sites were C-1, C-2, C-5, C-6, and C-15. Side chain hydroxylation in C₂₇ bile salts occurred at C-22, C-24, C-25, and C-26, and in C₂₄ bile acids, at C-23 (snakes, birds, and pinnipeds). Unexpected was the presence of C₂₇ bile alcohols in four early evolving mammals. Bile salt composition showed significant variation between orders but not between families, genera, or species. Bile salt composition is a biochemical trait providing clues to evolutionary relationships, complementing anatomical and genetic analyses.

Supplementary key words bile acids • cholesterol • enzymes • metabolism • molecular evolution • phylogeny

Abbreviations: CA, cholic acid; CDCA, chenodeoxycholic acid; CMC, critical micellization concentration; DCA, deoxycholic acid; FXR, farnesoid X receptor; LCA, lithocholic acid; PXR, pregnane X receptor; UDCA, ursodeoxycholic acid; VDR, vitamin D receptor

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