Bile acids LVII. Analysis of bile acids by high pressure liquid chromatography and mass spectrometry

Shaw, Roger; Elliott, William H.

doi:10.1007/bf02533858

Cited by 44 publications

(10 citation statements)

References 25 publications

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“…Edward Doisy, chairman of the Department of Biochemistry at St. Louis University, having already won the Nobel prize for his work on vitamin K, pursued the identity of the 3,6,7-trihydroxy bile acids in rats and identifi ed the ␣ -, ␤ -, and -muricholic acids ( 22 ). His student, William Elliott synthesized numerous bile acids and described their chemical and chromatographic properties ( 23 ).…”

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confidence: 99%

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

305

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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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

305

284

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“…However, only so-called "total bile acids" were estimated and the method was based on the assumption that the chemical nature of the bile acid(s) to be measured was known. Development of immunoassays provided another biological approach to bile acid analysis ( 11 ) The GLC requirement for volatility was eliminated when high-performance liquid chromatography (HPLC) was introduced ( 12 ). Separation effi ciencies of GLC and HPLC methods have been greatly improved since the time of their introduction.…”

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Bile acids: analysis in biological fluids and tissues

Griffiths

Sjövall

2010

Journal of Lipid Research

169

146

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in lower vertebrates. Metabolism of cholesterol to bile acids/bile alcohols is of major importance for the maintenance and regulation of cholesterol homeostasis. Depending on their structure, bile acids/bile alcohols can be ligands to nuclear receptors with different regulatory functions in animals, including even Caenorhabditis elegans ( 1 ). Bile acids can be formed in some marine microorganisms ( 2 ). These fi ndings have increased interest in methods for specifi c and sensitive analysis of bile acids.Conjugated forms of bile acids/bile alcohols in bile (bile salts) are essential participants in the absorption of lipids and lipid soluble compounds. Studies of this function, bile secretion, enterohepatic circulation, levels in blood, urine, and feces required methods for analysis of bile acids. In 1844, M. von Pettenkofer described his classical color reaction between cholic acid(s) and sugar in conc. sulfuric acid. During the subsequent 100 years, the reaction was modifi ed in numerous ways. This period is described by Sobotka ( 3, 4 ), who pointed out the discrepancies between the poor quality of the analytical methods of his days and the better understanding of bile acid physiology and pathology. He made the following remarks, well worth considering today:"The value of a method lies not only in its specifi city but also in the ease with which interfering factors may be specifi cally removed. To test the usefulness of a method, it is insuffi cient to demonstrate that solutions of the pure substance yield correct results and that known amounts of the substance, when added to biological material, may be completely recovered. It is absolutely necessary to prove that the analytical reaction given by the biological material or extract is due to the substance for which one tests. The unequivocal identifi cation of this substance, in amounts consistent with the analytical data, should alAbstract The formation of bile acids/bile alcohols is of major importance for the maintenance of cholesterol homeostasis. Besides their functions in lipid absorption, bile acids/bile alcohols are regulatory molecules for a number of metabolic processes. Their effects are structure-dependent, and numerous metabolic conversions result in a complex mixture of biologically active and inactive forms. Advanced methods are required to characterize and quantify individual bile acids in these mixtures. A combination of such analyses with analyses of the proteome will be required for a better understanding of mechanisms of action and nature of endogenous ligands. Mass spectrometry is the basic detection technique for effl uents from chromatographic columns. Capillary liquid chromatography-mass spectrometry with electrospray ionization provides the highest sensitivity in metabolome analysis. Classical gas chromatography-mass spectrometry is less sensitive but offers extensive structuredependent fragmentation increasing the specifi city in analyses of isobaric isomers of unconjugated bile acids. Depending on the nature of the bile acid/bile alc...

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“…As it was demonstrated before by other authors [27,69]; free bile acids were harder to detect than conjugated ones. Tauro-conjugated bile acids showed greater absorbance values than their corresponding glyco-conjugated ones.…”

Section: Resultsmentioning

confidence: 49%

“…During the last years, HPLC has been one of the most used techniques for the analysis and identification of different lipid classes [44] and, particularly, for the separation and quantification of bile acids and their derivatives in different biological materials, due to its possibility to be coupled to a great variety of detectors [14,27,[69][70][71][72][73][74]. HPLC presents several advantages in relation to other techniques such as high resolution, high sensitivity and specificity [44,75].…”

Section: High Performance Liquid Chromatographymentioning

confidence: 99%