A novel varanic acid epimer – (24R,25S)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid – is a major biliary bile acid in two varanid lizards and the Gila monster

Hagey, Lee R.; Ogawa, Shoujiro; Kato, Narimi; Satoh, Rika; Une, Mizuho; Mitamura, Kuniko; Ikegawa, Shigeo; Hofmann, Alan F.; Iida, Takashi

doi:10.1016/j.steroids.2012.08.017

Cited by 5 publications

(2 citation statements)

References 23 publications

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“…The most common diastereoismer is varanic acid, which has the 24 R ,25 R confi guration. In collaboration with the Iida and Une groups, we have found that the 24 R ,25 S epimer is present in the bile of several varanids ( 139 ). C 27 BILE ALCOHOLS.…”

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confidence: 86%

Key discoveries in bile acid chemistry and biology and their clinical applications: history of the last eight decades

Hofmann

Hagey

2014

Journal of Lipid Research

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284

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conceptions are rare, and provocative judgments stand the test of time. Let us also hope that this effort will be both useful and entertaining. Each of the topics discussed merits at least a full length article, so there will be, of necessity in many instances, consideration of only what we perceive to be the highlights. THE EBB AND FLOW OF MEDICAL INTEREST IN BILE ACIDSAfter the elucidation of the true chemical structure of bile acids in 1932 (see below), there was little interest in bile acids in the Western world. One exception to this statement was the laboratory of Siegfried Thannhauser, who wrote the fi rst textbook of metabolic biochemistry in Germany. He studied cholesterol and bile acid balance in the biliary fi stula dog ( 1 ). During this time, bile acids were sold as liver tonics and laxatives, but there were no placebo-controlled studies showing effi cacy. Indeed, bile acids were considered by the medical profession to have no useful therapeutic properties. The tri-oxo derivative of cholic acid (called "dehydrocholic acid") was known to induce bile fl ow in animals ( 2 ), and was occasionally used to stimulate bile fl ow in patients; but again there were no controlled studies showing effi cacy in hepatobiliary disease.

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Section: Downloaded Frommentioning

confidence: 86%

Key discoveries in bile acid chemistry and biology and their clinical applications: history of the last eight decades

Hofmann

Hagey

2014

Journal of Lipid Research

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284

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“…Compounds 29-31 are BA-sulfates, and SO 3 À (m/z = 79.9) was the major fragments for BA-sulfates. These compounds could be tentatively characterized by comparison with literature data (Yamaguchi et al, 2009;Chen et al, 2012;Hagey et al, 2012;Sergi et al, 2012).…”

Section: Steroidsmentioning

confidence: 99%

Characterization of chemical constituents and rats metabolites of Shuanghua Baihe tablets by HPLC‐Q‐TOF‐MS/MS

Zheng

Cong

Xue

et al. 2014

Biomedical Chromatography

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A high-performance liquid chromatography/quadrupole time-of-flight mass spectrometry method was established to detect as many constituents in rat biological fluids as possible after oral administration of Shuanghua Baihe tablets (SBT). An Agilent Poroshell 120 EC-C18 column was adopted to separate the samples, and mass spectra were acquired in positive and negative modes. First, the fingerprints of SBT were established, resulting in 32 components being detected within 40 min. Among these compounds, 12 were tentatively identified by comparing the retention times and mass spectral data with those of reference standards and the reference literature; the other 20 components were tentatively assigned solely based on the MS data. Furthermore, metabolites in rat plasma and urine after oral administration of SBT were also analyzed. A total of 19 compounds were identified, including 13 prototypes and six metabolites through metabolic pathways of demethylation and glucuronide conjugation. Glucuronidated alkaloids were the main constituents in the plasma, and were then excreted from urine. This is the first systematic study on the metabolic profiling of SBT.

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Two Major Bile Acids in the Hornbills, (24R,25S)‐3α,7α,24‐Trihydroxy‐5β‐cholestan‐27‐oyl Taurine and Its 12α‐Hydroxy Derivative

Satoh

Ogata

Saito

et al. 2016

Lipids

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Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes Buceros bicornis (great hornbill) and Penelopides panini (Visayan tarictic hornbill). Their structures were determined to be 3α,7α,24‐dihydroxy‐5β‐cholestan‐27‐oic acid and its 12α‐hydroxy derivative, 3α,7α,12α,24‐tetrahydroxy‐5β‐cholestan‐27‐oic acid (varanic acid, VA), both present in bile as their corresponding taurine amidates. The four diastereomers of varanic acid were synthesized and their assigned structures were confirmed by X‐ray crystallographic analysis. VA and its 12‐deoxy derivative were found to have a (24R,25S)‐configuration. 13 additional hornbill species were also analyzed by HPLC and showed similar bile acid patterns to B. bicornis and P. panini. The previous stereochemical assignment for (24R,25S)‐VA isolated from the bile of varanid lizards and the Gila monster should now be revised to the (24S,25S)‐configuration.

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A novel varanic acid epimer – (24R,25S)-3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid – is a major biliary bile acid in two varanid lizards and the Gila monster

Cited by 5 publications

References 23 publications

Key discoveries in bile acid chemistry and biology and their clinical applications: history of the last eight decades

Key discoveries in bile acid chemistry and biology and their clinical applications: history of the last eight decades

Characterization of chemical constituents and rats metabolites of Shuanghua Baihe tablets by HPLC‐Q‐TOF‐MS/MS

Two Major Bile Acids in the Hornbills, (24R,25S)‐3α,7α,24‐Trihydroxy‐5β‐cholestan‐27‐oyl Taurine and Its 12α‐Hydroxy Derivative

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