Isolation and chemical synthesis of a major, novel biliary bile acid in the common wombat (Vombatus ursinus): 15{alpha}-hydroxylithocholic acid.

Isolation and chemical synthesis of a major, novel biliary bile acid in the common wombat (Vombatus ursinus): 15{alpha}-hydroxylithocholic acid. Research Abstract Details 

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Isolation and chemical synthesis of a major, novel biliary bile acid in the common wombat (Vombatus ursinus): 15{alpha}-hydroxylithocholic acid. Abstract Text:

Genta Kakiyama,Hideyuki Tamegai,Takashi Iida,Kuniko Mitamura,Shigeo Ikegawa,Takaaki Goto,Nariyasu Mano,Junichi Goto,Peter Holz,Lee R Hagey,Alan F Hofmann,Genta Kakiyama,Hideyuki Tamegai,Takashi Iida,Kuniko Mitamura,Shigeo Ikegawa,Takaaki Goto,Nariyasu Mano,Junichi Goto,Peter Holz,Lee R Hagey,Alan F Hofmann,Genta Kakiyama,Hideyuki Tamegai,Takashi Iida,Kuniko Mitamura,Shigeo Ikegawa,Takaaki Goto,Nariyasu Mano,Junichi Goto,Peter Holz,Lee R Hagey,Alan F Hofmann,

The major bile acids present in the gallbladder bile of the common Australian wombat (Vombatus ursinus) were isolated by preparative HPLC and identified by NMR as the taurine N-acylamidates of chenodeoxycholic acid (CDCA) and 15alpha-hydroxylithocholic acid (3alpha,15alpha-dihydroxy-5beta-cholan-24-oic acid). Taurine-conjugated CDCA constituted 78% of biliary bile acids, and (taurine-conjugated) 15alpha-hydroxylithocholic acid constituted 11%. Proof of structure of the latter compound was obtained by its synthesis from CDCA via a Delta(14) intermediate. The synthesis of its C-15 epimer, 15beta-hydroxylithocholic acid (3alpha,15beta-dihydroxy-5beta-cholan-24-oic acid), is also reported. The taurine conjugate of 15alpha-hydroxylithocholic acid was synthesized and shown to have chromatographic and spectroscopic properties identical to those of the compound isolated from bile. It is likely that 15alpha-hydroxylithocholic acid is synthesized in the wombat hepatocyte by 15alpha-hydroxylation of lithocholic acid that was formed by bacterial 7alpha-dehydroxylation of CDCA in the distal intestine. Thus, the wombat appears to use 15alpha-hydroxylation as a novel detoxification mechanism for lithocholic acid.

Isolation and chemical synthesis of a major, novel biliary bile acid in the common wombat (Vombatus ursinus): 15{alpha}-hydroxylithocholic acid. Publishing Authors By Initials

G Kakiyama,H Tamegai,T Iida,K Mitamura,S Ikegawa,T Goto,N Mano,J Goto,P Holz,LR Hagey,AF Hofmann,G Kakiyama,H Tamegai,T Iida,K Mitamura,S Ikegawa,T Goto,N Mano,J Goto,P Holz,LR Hagey,AF Hofmann,G Kakiyama,H Tamegai,T Iida,K Mitamura,S Ikegawa,T Goto,N Mano,J Goto,P Holz,LR Hagey,AF Hofmann,

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Isolation and chemical synthesis of a major, novel biliary bile acid in the common wombat (Vombatus ursinus): 15{alpha}-hydroxylithocholic acid. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of lipid research

VOLUME: 48

Page Numbers: 2682-92

Journal Abbreviation: J. Lipid Res.

ISSN: 0022-2275

DAY: 4

MONTH: 09

YEAR: 2007

Isolation and chemical synthesis of a major, novel biliary bile acid in the common wombat (Vombatus ursinus): 15{alpha}-hydroxylithocholic acid. Information

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LANGUAGE: eng

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AFFILIATION: Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajosui, Setagaya, Tokyo 156-8550, Japan.

Country: United States

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MEDLINETA: J Lipid Res

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