Tandem mass spectrometric characterization of bile acids and steroid conjugates based on low-energy collision-induced dissociation

Masamitsu Maekawa, Miki Simada, Takashi Iida, Junichi Goto, Nariyasu Mano

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

We examined the characteristics of several bile acids and some steroid conjugates under low-energy-collision-induced dissociation conditions using a triple quadrupole tandem mass spectrometer. According to conjugation types, we observed characteristic product ions and/or neutral losses in the product ion spectra. Amino acid conjugates afforded specific product ions. For example, glycine-conjugated metabolites routinely produced a product ion at m/z 74, and taurine-conjugated metabolites produced product ions at m/z 124, 107, and 80. When a strong peak appeared at m/z 97, the molecule contained a sulfate group. In contrast to amino acid conjugates, carbohydrate conjugates required a combination of product ions and neutral losses for identification. We could discriminate a glucoside from an acyl galactoside according to the presence or absence of a product ion at m/z 161 and a neutral loss of 180 Da. Discrimination among esters, aliphatic ethers, and phenolic ether types of glucuronides was based upon differences in the intensities of a product ion at m/z 175 and a neutral loss of 176 Da. Furthermore, N-acetylglucosamine conjugates showed a characteristic product ion at m/z 202 and a neutral loss of 203 Da, and the appearance of a product ion at m/z 202 revealed the existence of N-acetylglucosamine conjugated to an aliphatic hydroxyl group without a double bond in the immediate vicinity. Together, the data presented here will help to enable the identification of unknown conjugated cholesterol metabolites by using low-energy collision-induced dissociation.

Original languageEnglish
Pages (from-to)80-91
Number of pages12
JournalSteroids
Volume80
DOIs
Publication statusPublished - 2014 Feb 1

Keywords

  • Bile acid conjugate
  • Low-energy collision-induced dissociation
  • Neutral loss
  • Product ion
  • Steroid conjugate

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Pharmacology
  • Endocrinology
  • Clinical Biochemistry
  • Organic Chemistry

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