A novel enzyme system for the reduction of 3-oxo bile acids in human red blood cells
7α,12α-Dihydroxy-3-oxo- and 3,7,12-trioxo-5β-cholanoic acids labeled with 18O atoms were incubated with human red blood cells, and the biotransformation products were separated and characterized by gas chromatography-mass spectrometry as the pentafluorobenzyl ester-trimethylsilyl and -dimethylethyls...
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| Veröffentlicht in: | Steroids 1996-07, Vol.61 (7), p.416-420 |
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| creator | Goto, Junichi Miura, Hiroya Ando, Masayuki Yamato, Yasuhiro Ikegawa, Shigeo Nambara, Toshio Makino, Isao |
| description | 7α,12α-Dihydroxy-3-oxo- and 3,7,12-trioxo-5β-cholanoic acids labeled with
18O atoms were incubated with human red blood cells, and the biotransformation products were separated and characterized by gas chromatography-mass spectrometry as the pentafluorobenzyl ester-trimethylsilyl and -dimethylethylsilyl ether derivatives with the negative ion chemical ionization mode. The reduced products, 3β,7α,12α-trihydroxy-5β-cholanoic acid for the former, and 3α-hydroxylated dioxo bile acid together with 3β-hydroxylated 7,12-dioxo-5β-cholanoic acid for the latter, were identified as metabolites. When 3-oxo bile acid was incubated with human blood denatured at 70°C for 2 min, no metabolites were formed. The enzymic reduction activity has been localized in the red blood cell fraction. |
| doi_str_mv | 10.1016/0039-128X(96)00061-X |
| format | Article |
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18O atoms were incubated with human red blood cells, and the biotransformation products were separated and characterized by gas chromatography-mass spectrometry as the pentafluorobenzyl ester-trimethylsilyl and -dimethylethylsilyl ether derivatives with the negative ion chemical ionization mode. The reduced products, 3β,7α,12α-trihydroxy-5β-cholanoic acid for the former, and 3α-hydroxylated dioxo bile acid together with 3β-hydroxylated 7,12-dioxo-5β-cholanoic acid for the latter, were identified as metabolites. When 3-oxo bile acid was incubated with human blood denatured at 70°C for 2 min, no metabolites were formed. The enzymic reduction activity has been localized in the red blood cell fraction.</description><subject>3-oxo bile acid</subject><subject>Bile Acids and Salts - chemistry</subject><subject>Bile Acids and Salts - metabolism</subject><subject>Biological and medical sciences</subject><subject>Biotransformation</subject><subject>Blood - metabolism</subject><subject>Cholic Acids - chemical synthesis</subject><subject>Cholic Acids - chemistry</subject><subject>Cholic Acids - metabolism</subject><subject>Chromatography, Gas</subject><subject>Dehydrocholic Acid - chemical synthesis</subject><subject>Dehydrocholic Acid - chemistry</subject><subject>Dehydrocholic Acid - metabolism</subject><subject>enzymic reduction</subject><subject>Erythrocytes - metabolism</subject><subject>extrahepatic biotransformation</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>gas chromatography-mass spectrometry</subject><subject>Humans</subject><subject>ion cluster technique</subject><subject>Mass Spectrometry</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Oxygen Isotopes</subject><subject>red blood cell</subject><subject>Vertebrates: blood, hematopoietic organs, reticuloendothelial system</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1r3DAQhkVpSLdp_0ELOoTQHNyOJFsfl0AIaRMI5JLC3oRWGhMV20okO2Tz62Ozyx57Gob3meHlIeQbg58MmPwFIEzFuF7_MPIcACSr1h_Iimmlq0ZL9ZGsDsgn8rmUfwskDD8mx1oLxU29Ig-XdEgv2FEc3rY90rItI_a0TZmOj0gzhsmPMQ00tVRU6TXRTeyQOh9DoXGgj1PvhgWjmy6lQD12XflCjlrXFfy6nyfk7-_rh6ub6u7-z-3V5V3lhZZjxV3d1IF7LjGAQ8YNCFCI3rOmqYX2qqmVk60UqGtgRoAzwJVijQkQ2EackLPd36ecnicso-1jWRq4AdNUrNLCgGF6Busd6HMqJWNrn3LsXd5aBnaRaRdTdjFlzbLMMu16Pvu-_z9tegyHo729OT_d565417XZDT6WAyZ4wySDGbvYYTi7eImYbfERB48hZvSjDSn-v8c7IkWO6g</recordid><startdate>19960701</startdate><enddate>19960701</enddate><creator>Goto, Junichi</creator><creator>Miura, Hiroya</creator><creator>Ando, Masayuki</creator><creator>Yamato, Yasuhiro</creator><creator>Ikegawa, Shigeo</creator><creator>Nambara, Toshio</creator><creator>Makino, Isao</creator><general>Elsevier Inc</general><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19960701</creationdate><title>A novel enzyme system for the reduction of 3-oxo bile acids in human red blood cells</title><author>Goto, Junichi ; Miura, Hiroya ; Ando, Masayuki ; Yamato, Yasuhiro ; Ikegawa, Shigeo ; Nambara, Toshio ; Makino, Isao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c386t-2a454d2c26ed0ae1290307eecc155438c7547a6f63e8401930a90277159d0d1b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>3-oxo bile acid</topic><topic>Bile Acids and Salts - chemistry</topic><topic>Bile Acids and Salts - metabolism</topic><topic>Biological and medical sciences</topic><topic>Biotransformation</topic><topic>Blood - metabolism</topic><topic>Cholic Acids - chemical synthesis</topic><topic>Cholic Acids - chemistry</topic><topic>Cholic Acids - metabolism</topic><topic>Chromatography, Gas</topic><topic>Dehydrocholic Acid - chemical synthesis</topic><topic>Dehydrocholic Acid - chemistry</topic><topic>Dehydrocholic Acid - metabolism</topic><topic>enzymic reduction</topic><topic>Erythrocytes - metabolism</topic><topic>extrahepatic biotransformation</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>gas chromatography-mass spectrometry</topic><topic>Humans</topic><topic>ion cluster technique</topic><topic>Mass Spectrometry</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Oxygen Isotopes</topic><topic>red blood cell</topic><topic>Vertebrates: blood, hematopoietic organs, reticuloendothelial system</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goto, Junichi</creatorcontrib><creatorcontrib>Miura, Hiroya</creatorcontrib><creatorcontrib>Ando, Masayuki</creatorcontrib><creatorcontrib>Yamato, Yasuhiro</creatorcontrib><creatorcontrib>Ikegawa, Shigeo</creatorcontrib><creatorcontrib>Nambara, Toshio</creatorcontrib><creatorcontrib>Makino, Isao</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Steroids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goto, Junichi</au><au>Miura, Hiroya</au><au>Ando, Masayuki</au><au>Yamato, Yasuhiro</au><au>Ikegawa, Shigeo</au><au>Nambara, Toshio</au><au>Makino, Isao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A novel enzyme system for the reduction of 3-oxo bile acids in human red blood cells</atitle><jtitle>Steroids</jtitle><addtitle>Steroids</addtitle><date>1996-07-01</date><risdate>1996</risdate><volume>61</volume><issue>7</issue><spage>416</spage><epage>420</epage><pages>416-420</pages><issn>0039-128X</issn><eissn>1878-5867</eissn><coden>STEDAM</coden><abstract>7α,12α-Dihydroxy-3-oxo- and 3,7,12-trioxo-5β-cholanoic acids labeled with
18O atoms were incubated with human red blood cells, and the biotransformation products were separated and characterized by gas chromatography-mass spectrometry as the pentafluorobenzyl ester-trimethylsilyl and -dimethylethylsilyl ether derivatives with the negative ion chemical ionization mode. The reduced products, 3β,7α,12α-trihydroxy-5β-cholanoic acid for the former, and 3α-hydroxylated dioxo bile acid together with 3β-hydroxylated 7,12-dioxo-5β-cholanoic acid for the latter, were identified as metabolites. When 3-oxo bile acid was incubated with human blood denatured at 70°C for 2 min, no metabolites were formed. The enzymic reduction activity has been localized in the red blood cell fraction.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>8837294</pmid><doi>10.1016/0039-128X(96)00061-X</doi><tpages>5</tpages></addata></record> |
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| ispartof | Steroids, 1996-07, Vol.61 (7), p.416-420 |
| issn | 0039-128X 1878-5867 |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | 3-oxo bile acid Bile Acids and Salts - chemistry Bile Acids and Salts - metabolism Biological and medical sciences Biotransformation Blood - metabolism Cholic Acids - chemical synthesis Cholic Acids - chemistry Cholic Acids - metabolism Chromatography, Gas Dehydrocholic Acid - chemical synthesis Dehydrocholic Acid - chemistry Dehydrocholic Acid - metabolism enzymic reduction Erythrocytes - metabolism extrahepatic biotransformation Fundamental and applied biological sciences. Psychology gas chromatography-mass spectrometry Humans ion cluster technique Mass Spectrometry Molecular Structure Oxidation-Reduction Oxygen Isotopes red blood cell Vertebrates: blood, hematopoietic organs, reticuloendothelial system |
| title | A novel enzyme system for the reduction of 3-oxo bile acids in human red blood cells |
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