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Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)

Sterols are widely distributed in nature from lipids in organisms to sediments. As a conventional method, extraction and derivatization with TMS have been applied for sterol analysis, requiring a long preparation time for gas chromatography–mass spectrometry analysis. In this study, for sterol analy...

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Autores principales: Nakakuni, Masatoshi, Yamasaki, Yoshimi, Yoshitake, Nonoka, Takehara, Keiko, Yamamoto, Shuichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6928973/
https://www.ncbi.nlm.nih.gov/pubmed/31703423
http://dx.doi.org/10.3390/molecules24224040
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author Nakakuni, Masatoshi
Yamasaki, Yoshimi
Yoshitake, Nonoka
Takehara, Keiko
Yamamoto, Shuichi
author_facet Nakakuni, Masatoshi
Yamasaki, Yoshimi
Yoshitake, Nonoka
Takehara, Keiko
Yamamoto, Shuichi
author_sort Nakakuni, Masatoshi
collection PubMed
description Sterols are widely distributed in nature from lipids in organisms to sediments. As a conventional method, extraction and derivatization with TMS have been applied for sterol analysis, requiring a long preparation time for gas chromatography–mass spectrometry analysis. In this study, for sterol analysis, thermochemolysis using tetramethylammonium hydroxide (TMAH) was applied. This method performs hydrolysis and methylation simultaneously; thus, free and ether-bonding sterols can be analyzed as sterol methyl ethers in a relatively short time period. A sediment sample from a tideland (the Yatsu tideland, Japan) was analyzed using the TMAH method, and we detected more than 10 sterols, which include cholest-5-en-3β-ol (cholesterol), 24-ethylcholest-5-en-3β-ol (sitosterol), 24-methylcholesta-5,22E-3β-ol (brassicasterol), 24-ethylcholesta-5,24(28)Z-dien-3β-ol (isofucosterol), 4α,23,24-trimethyl-5α(H)-cholest-22E-en-3β- ol (dinosterol), and 5β(H)-cholestan-3β-ol (coprostanol). The detection of the various sterols can be attributed to multiple natural and artificial sources around the Yatsu tideland. In this paper, the mass spectra of these sterols are provided together with an interpretation of their fragmentation patterns. Additionally, the fecal pollution in the Yatsu tideland is discussed in the context of the detection of coprostanol.
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spelling pubmed-69289732019-12-26 Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH) Nakakuni, Masatoshi Yamasaki, Yoshimi Yoshitake, Nonoka Takehara, Keiko Yamamoto, Shuichi Molecules Article Sterols are widely distributed in nature from lipids in organisms to sediments. As a conventional method, extraction and derivatization with TMS have been applied for sterol analysis, requiring a long preparation time for gas chromatography–mass spectrometry analysis. In this study, for sterol analysis, thermochemolysis using tetramethylammonium hydroxide (TMAH) was applied. This method performs hydrolysis and methylation simultaneously; thus, free and ether-bonding sterols can be analyzed as sterol methyl ethers in a relatively short time period. A sediment sample from a tideland (the Yatsu tideland, Japan) was analyzed using the TMAH method, and we detected more than 10 sterols, which include cholest-5-en-3β-ol (cholesterol), 24-ethylcholest-5-en-3β-ol (sitosterol), 24-methylcholesta-5,22E-3β-ol (brassicasterol), 24-ethylcholesta-5,24(28)Z-dien-3β-ol (isofucosterol), 4α,23,24-trimethyl-5α(H)-cholest-22E-en-3β- ol (dinosterol), and 5β(H)-cholestan-3β-ol (coprostanol). The detection of the various sterols can be attributed to multiple natural and artificial sources around the Yatsu tideland. In this paper, the mass spectra of these sterols are provided together with an interpretation of their fragmentation patterns. Additionally, the fecal pollution in the Yatsu tideland is discussed in the context of the detection of coprostanol. MDPI 2019-11-07 /pmc/articles/PMC6928973/ /pubmed/31703423 http://dx.doi.org/10.3390/molecules24224040 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Nakakuni, Masatoshi
Yamasaki, Yoshimi
Yoshitake, Nonoka
Takehara, Keiko
Yamamoto, Shuichi
Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)
title Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)
title_full Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)
title_fullStr Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)
title_full_unstemmed Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)
title_short Methyl Ether-Derivatized Sterols and Coprostanol Produced via Thermochemolysis Using Tetramethylammonium Hydroxide (TMAH)
title_sort methyl ether-derivatized sterols and coprostanol produced via thermochemolysis using tetramethylammonium hydroxide (tmah)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6928973/
https://www.ncbi.nlm.nih.gov/pubmed/31703423
http://dx.doi.org/10.3390/molecules24224040
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