Identification of a novel bile acid in swans, tree ducks, and geese: 3α,7α,15α-trihydroxy-5β-cholan-24-oic acid

Kakiyama, Genta; Iida, Takashi; Goto, Takaaki; Mano, Nariyasu; Goto, Junichi; Nambara, Toshio; Hagey, Lee R.; Schteingart, Claudio D.; Hofmann, Alan F.

doi:10.1194/jlr.m600149-jlr200

Cited by 15 publications

(11 citation statements)

References 25 publications

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“…The NMR data (Tables 1, 2) were in good agreement with those of the known compound 3a,7a,15a-trihydroxy-5b-cholan-24-oyl taurine (10), 13) except for signals due to absence of taurine group at the side chain. Compound 3 was further determined as 3a,7a,15a-trihydroxy-5b-cholan-24- oic acid by interpretation of 2D NMR spectrum, and had been named as cygnocholic acid by Kakiyama et al…”

Section: Resultssupporting

confidence: 68%

“…2) from H 2 -23 and H 2 -25 to C-24. Analysis of 13 C-NMR spectra through DEPT of 1 also showed that C-9 was a non-protonated carbon. Thus, the additional hydroxyl group was determined at C-9, which was confirmed by HMBC correlations (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…13) With this report, two new additional sites of hydroxylation on the cholanoic acid nucleus in primary bile acids were discovered at C-9 and C-5. These bile acid structures may provide the useful information for phylogenesis.…”

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confidence: 99%

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Novel Bile Acids from Bear Bile Powder and Bile of Geese

Chai

Song

et al. 2009

Chem. Pharm. Bull.

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Bile acids, as the water-soluble amphipathic end products of cholesterol metabolism, are important due to their roles in elimination of cholesterol and absorption of lipids and fatsoluble vitamins in the intestine.1) C24 bile acids found in most mammals are present in bile as N-acyl amidates (conjugates) of taurine or glycine.2) All primary C24 bile acids have a hydroxyl group at C-3 which is from cholesterol and at C-7, as cholesterol 7a-hydroxylation is the rate-limiting step in bile acid biosynthesis. Thus, chenodeoxycholic acid (CDCA; 3a,7a-dihydroxy-5b-cholan-24-oic acid) is the root C24 bile acid.3) Chenodeoxycholic acid and ursodeoxycholic acid (UDCA; 3a,7a-dihydroxy-5b-cholanoic acid) are widely used for the treatment of cholesterol gall-stones and ursodeoxycholic acid has been introduced for the therapy of cholestatic liver diseases. [4][5][6][7][8][9] In the previous study, several bile acids including CDCA, CA, TCDCA, TUDCA, TCA were obtained from bile of Ursus arctos by Yamaguchi et al. 10) In order to search for new natural bioactive constituents from animal bile and provide chemical standards for the research on its quality control, two kinds of bile from different animals including Selenaretos thibetanus CUVIER and Anser anser domesticus were chemically investigated in our research group. This paper describes the isolation and structural determination of two novel bile acids, tauroselocholic acid (1), tauroansocholic acid (2), and a new natural bile acid, cygnocholic acid (3) which had been synthesized by Iida et al.,11) together with seven known compounds from these two kinds of bile. Results and DiscussionCompound 1 was isolated as colorless syrup, and it showed positive Gregory Pascoe reaction, suggesting it to be a bile acid. Its molecular formula C 26 H 45 NO 7 S was established by the pseudo-molecular ion peak at m/z 514.2860 [MϪH] Ϫ in the HR-ESI-MS and confirmed by the NMR data analysis. The IR spectrum indicated the presence of hydroxyl group (3420 cm C-NMR spectra (distortionless enhancement by polarization transfer (DEPT)) exhibited three methyls, twelve methylenes, seven methines and four quaternary carbons. Analysis of the 13 C-NMR spectrum showed three hydroxylated carbons at d 68.2 (CH), 73.1 (CH) and 75.8 (q C), and one amide carbonyl at d 176.6. The above data showed high similarity with those of the known compound, 3a,7a-dihydroxy-5b-cholanoic acid N- [2-sulfoethyl] amide (8) 10) except for an additional hydroxyl group, which implied 1 to has 3a-hydroxyl and 7a-hydroxyl substituents. Interpretation of the 1 H-1 H correlation spectroscopy (COSY) spectrum led to the determination of partial structures I, II and III (Fig. 2). Partial structure I were connected to II by heteronuclear multiple bonding connectivity (HMBC) correlations (Fig. 2) from H 3 -19 to C-5, C-9, C-10, from H 3 -18 to C-12, C-13, C-14, C-17, and from H-11b to C-8. The structural moiety I was also connected to III by HMBC correlations (Fig. 2) from H 2 -23 and H 2 -25 to C-24. Analysis of 13 C-NMR spectra t...

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Section: Resultssupporting

confidence: 68%

Section: Resultsmentioning

confidence: 99%

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Novel Bile Acids from Bear Bile Powder and Bile of Geese

Chai

Song

et al. 2009

Chem. Pharm. Bull.

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“…We previously reported that 15a-hydroxylation occurs in swans, tree ducks, and geese, in whom 3a,7a,15a-trihydroxy-5b-cholan-24-oic acid is a primary bile acid (2). We think it highly unlikely that 15a-hydroxylithocholic acid arose by bacterial 7a-dehydroxylation of this primary, trihydroxy bile acid, as it was not present in the biliary bile acids of the wombat.…”

Section: Biological Aspectsmentioning

confidence: 99%

“…After being allowed to stand overnight at room temperature, the mixture was poured into ice water (0jC) and extracted with CH 2 Synthesis of 3a-hydroxy-5b-chol-7-en-24-oic acid (5a) and its methyl ester (5b)…”

Section: Lc-esi-ms/ms Of Compound Cmentioning

confidence: 99%

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

Kakiyama

Tamegai

Iida

et al. 2007

Journal of Lipid Research

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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 15a-hydroxylithocholic acid (3a,15a-dihydroxy5b-cholan-24-oic acid). Taurine-conjugated CDCA constituted 78% of biliary bile acids, and (taurine-conjugated) 15a-hydroxylithocholic acid constituted 11%. Proof of structure of the latter compound was obtained by its synthesis from CDCA via a # 14 intermediate. The synthesis of its C-15 epimer, 15b-hydroxylithocholic acid (3a,15b-dihydroxy-5b-cholan-24-oic acid), is also reported. The taurine conjugate of 15a-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 15a-hydroxylithocholic acid is synthesized in the wombat hepatocyte by 15a-hydroxylation of lithocholic acid that was formed by bacterial 7a-dehydroxylation of CDCA in the distal intestine. Thus, the wombat appears to use 15a-hydroxylation as a novel detoxification mechanism for lithocholic acid

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Bile acids: Trying to understand their chemistry and biology with the hope of helping patients

2008

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An informal review of the author's five decades of research on the chemistry and biology of bile acids in health and disease is presented. The review begins with a discussion of bile acid structure and its remarkable diversity in vertebrates. Methods for tagging bile acids with tritium for metabolic or transport studies are summarized. Bile acids solubilize polar lipids in mixed micelles; progress in elucidating the structure of the mixed micelle is discussed. Extensive studies on bile acid metabolism in humans have permitted the development of physiological pharmacokinetic models that can be used to simulate bile acid metabolism. Consequences of defective bile acid biosynthesis and transport have been clarified, and therapy has been developed. Methods for measuring bile acids have been improved. The rise and fall of medical and contact dissolution of cholesterol gallstones is chronicled. Finally, principles of therapy with bile acid agonists and antagonists are given. Advances in understanding bile acid biology and chemistry have helped to improve the lives of patients with hepatobiliary or digestive disease.

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Identification of a novel bile acid in swans, tree ducks, and geese: 3α,7α,15α-trihydroxy-5β-cholan-24-oic acid

Cited by 15 publications

References 25 publications

Novel Bile Acids from Bear Bile Powder and Bile of Geese

Novel Bile Acids from Bear Bile Powder and Bile of Geese

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

Bile acids: Trying to understand their chemistry and biology with the hope of helping patients

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