Communication. Detection of equol in the steroid fraction from sturgeon (Acipenser baeri) plasma using capillary gas chromatography-mass spectrometry
Identifieur interne : 000431 ( Istex/Corpus ); précédent : 000430; suivant : 000432Communication. Detection of equol in the steroid fraction from sturgeon (Acipenser baeri) plasma using capillary gas chromatography-mass spectrometry
Auteurs : Catherine Pelissero ; Françoise Le Menn ; Philippe GarriguesSource :
- Analyst [ 0003-2654 ] ; 1989.
Abstract
Equol, which is a derivative of the vegetal isoflavone formononetin and obtained by bacterial degradation in the digestive tract of mammals fed on a vegetal diet, has been detected in the plasma of sturgeon fed on a soya-based fish diet. Such a compound, which is a structural analogue of certain sexual steroids, e.g., estradiol, has been demonstrated to have an estrogenic activity in several mammals and as such it could also be responsible for the secretion of vitellogenin by hepatocytes in male sturgeons. A combined analytical procedure involving several liquid chromatographic separations and capillary gas chromatography-mass spectrometry with chemical ionisation led to the detection of equol in estradiol extracts from fish plasma.
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DOI: 10.1039/AN9891401703
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Detection of equol in the steroid fraction from sturgeon (Acipenser baeri) plasma using capillary gas chromatography-mass spectrometry</title><author wicri:is="90%"><name sortKey="Pelissero, Catherine" sort="Pelissero, Catherine" uniqKey="Pelissero C" first="Catherine" last="Pelissero">Catherine Pelissero</name></author><author wicri:is="90%"><name sortKey="Le Menn, Francoise" sort="Le Menn, Francoise" uniqKey="Le Menn F" first="Françoise" last="Le Menn">Françoise Le Menn</name></author><author wicri:is="90%"><name sortKey="Garrigues, Philippe" sort="Garrigues, Philippe" uniqKey="Garrigues P" first="Philippe" last="Garrigues">Philippe Garrigues</name></author></analytic><monogr></monogr><series><title level="j">Analyst</title><title level="j" type="abbrev">Analyst</title><idno type="ISSN">0003-2654</idno><idno type="eISSN">1364-5528</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="1989">1989</date><biblScope unit="volume">114</biblScope><biblScope unit="issue">12</biblScope><biblScope unit="page" from="1703">1703</biblScope><biblScope unit="page" to="1705">1705</biblScope></imprint><idno type="ISSN">0003-2654</idno></series><idno type="istex">8018B8BBE055D8F58DF20BF6D7400924676A43C8</idno><idno type="DOI">10.1039/AN9891401703</idno><idno type="ms-id">AN9891401703</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0003-2654</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">Equol, which is a derivative of the vegetal isoflavone formononetin and obtained by bacterial degradation in the digestive tract of mammals fed on a vegetal diet, has been detected in the plasma of sturgeon fed on a soya-based fish diet. Such a compound, which is a structural analogue of certain sexual steroids, e.g., estradiol, has been demonstrated to have an estrogenic activity in several mammals and as such it could also be responsible for the secretion of vitellogenin by hepatocytes in male sturgeons. 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Such a compound, which is a structural analogue of certain sexual steroids, e.g., estradiol, has been demonstrated to have an estrogenic activity in several mammals and as such it could also be responsible for the secretion of vitellogenin by hepatocytes in male sturgeons. A combined analytical procedure involving several liquid chromatographic separations and capillary gas chromatography-mass spectrometry with chemical ionisation led to the detection of equol in estradiol extracts from fish plasma.</abstract><qualityIndicators><score>4.868</score><pdfVersion>1.3</pdfVersion><pdfPageSize>587.999 x 827.759 pts</pdfPageSize><refBibsNative>false</refBibsNative><keywordCount>0</keywordCount><abstractCharCount>742</abstractCharCount><pdfWordCount>1524</pdfWordCount><pdfCharCount>8658</pdfCharCount><pdfPageCount>3</pdfPageCount><abstractWordCount>112</abstractWordCount></qualityIndicators><title>Communication. Detection of equol in the steroid fraction from sturgeon (Acipenser baeri) plasma using capillary gas chromatography-mass spectrometry</title><genre><json:string>research-article</json:string></genre><host><volume>114</volume><pages><total>3</total><last>1705</last><first>1703</first></pages><issn><json:string>0003-2654</json:string></issn><issue>12</issue><genre><json:string>journal</json:string></genre><language><json:string>unknown</json:string></language><eissn><json:string>1364-5528</json:string></eissn><title>Analyst</title></host><categories><wos><json:string>science</json:string><json:string>chemistry, analytical</json:string></wos><scienceMetrix><json:string>natural sciences</json:string><json:string>chemistry</json:string><json:string>analytical chemistry</json:string></scienceMetrix></categories><publicationDate>1989</publicationDate><copyrightDate>1989</copyrightDate><doi><json:string>10.1039/AN9891401703</json:string></doi><id>8018B8BBE055D8F58DF20BF6D7400924676A43C8</id><score>0.054802433</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/8018B8BBE055D8F58DF20BF6D7400924676A43C8/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/8018B8BBE055D8F58DF20BF6D7400924676A43C8/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/8018B8BBE055D8F58DF20BF6D7400924676A43C8/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a">Communication. 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Detection of equol in the steroid fraction from sturgeon (Acipenser baeri) plasma using capillary gas chromatography-mass spectrometry</title><author xml:id="author-1"><persName><forename type="first">Catherine</forename><surname>Pelissero</surname></persName></author><author xml:id="author-2"><persName><forename type="first">Françoise</forename><surname>Le Menn</surname></persName></author><author xml:id="author-3"><persName><forename type="first">Philippe</forename><surname>Garrigues</surname></persName></author></analytic><monogr><title level="j">Analyst</title><title level="j" type="abbrev">Analyst</title><idno type="pISSN">0003-2654</idno><idno type="eISSN">1364-5528</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="1989"></date><biblScope unit="volume">114</biblScope><biblScope unit="issue">12</biblScope><biblScope unit="page" from="1703">1703</biblScope><biblScope unit="page" to="1705">1705</biblScope></imprint></monogr><idno type="istex">8018B8BBE055D8F58DF20BF6D7400924676A43C8</idno><idno type="DOI">10.1039/AN9891401703</idno><idno type="ms-id">AN9891401703</idno></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1989</date></creation><langUsage><language ident="en">en</language></langUsage><abstract><p>Equol, which is a derivative of the vegetal isoflavone formononetin and obtained by bacterial degradation in the digestive tract of mammals fed on a vegetal diet, has been detected in the plasma of sturgeon fed on a soya-based fish diet. Such a compound, which is a structural analogue of certain sexual steroids, e.g., estradiol, has been demonstrated to have an estrogenic activity in several mammals and as such it could also be responsible for the secretion of vitellogenin by hepatocytes in male sturgeons. A combined analytical procedure involving several liquid chromatographic separations and capillary gas chromatography-mass spectrometry with chemical ionisation led to the detection of equol in estradiol extracts from fish plasma.</p></abstract></profileDesc><revisionDesc><change when="1989">Published</change><change xml:id="refBibs-istex" who="#ISTEX-API" when="2017-01-18">References added</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/8018B8BBE055D8F58DF20BF6D7400924676A43C8/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="corpus rsc-journals not found" wicri:toSee="no header"><istex:xmlDeclaration>version="1.0" encoding="UTF-8"</istex:xmlDeclaration><istex:document><article type="ART" xsi:schemaLocation="http://www.rsc.org/schema/rscart38 http://www.rsc.org/schema/rscart38/rscart38.xsd" dtd="RSCART3.8"><metainfo><articletype code="ART" pubmedForm="research-article" headingForm="Papers" group="Paper" fullForm="Paper"></articletype></metainfo><art-admin><ms-id>AN9891401703</ms-id><doi>10.1039/AN9891401703</doi></art-admin><published type="print"><journalref><link>AN</link></journalref><volumeref><link>114</link></volumeref><issueref><link>12</link></issueref><pubfront><fpage>1703</fpage><lpage>1705</lpage><no-of-pages>3</no-of-pages><date><year>1989</year></date></pubfront></published><published type="subsyear"><journalref><title type="abbreviated">Analyst</title><title type="full">Analyst</title><title type="journal">Analyst</title><title type="display">Analyst</title><title type="pubmed">Analyst</title><sercode>AN</sercode><publisher><orgname><nameelt>The Royal Society of Chemistry</nameelt></orgname></publisher><issn type="print">0003-2654</issn><issn type="online">1364-5528</issn><coden>ANALAO</coden><cpyrt>This journal is © The Royal Society of Chemistry</cpyrt></journalref><pubfront><fpage></fpage><lpage></lpage><no-of-pages></no-of-pages><date><year>1989</year></date></pubfront></published><art-front><titlegrp><title>Communication. Detection of equol in the steroid fraction from sturgeon (<it>Acipenser baeri</it>) plasma using capillary gas chromatography-mass spectrometry</title></titlegrp><authgrp><author><person><persname><fname>Catherine</fname><surname>Pelissero</surname></persname></person></author><author><person><persname><fname>Françoise</fname><surname>Le Menn</surname></persname></person></author><author><person><persname><fname>Philippe</fname><surname>Garrigues</surname></persname></person></author></authgrp><abstract><p>Equol, which is a derivative of the vegetal isoflavone formononetin and obtained by bacterial degradation in the digestive tract of mammals fed on a vegetal diet, has been detected in the plasma of sturgeon fed on a soya-based fish diet. Such a compound, which is a structural analogue of certain sexual steroids, <it>e.g.</it>, estradiol, has been demonstrated to have an estrogenic activity in several mammals and as such it could also be responsible for the secretion of vitellogenin by hepatocytes in male sturgeons. A combined analytical procedure involving several liquid chromatographic separations and capillary gas chromatography-mass spectrometry with chemical ionisation led to the detection of equol in estradiol extracts from fish plasma.</p></abstract></art-front><art-body><section type="PDFExtract"><title></title><p> ANALYST, DECEMBER 1989, VOL. 114 1703 COM M U Nl CATION Material for publication as a Communication must be on an urgent matter and be of obvious scientific importance. Rapidity of publication is enhanced if diagrams are omitted, but tables and formulae can be included. Communications receive priority and are usually published within 5-8 weeks of receipt. They are intended for brief descriptions of work that has progressed to a stage at which it is likely to be valuable to workers faced with similar problems. A fuller paper may be offered subsequently, if justified by later work. Manuscripts are usually examined by one referee and inclusion of a Communication is at the Editor’s discretion. Detection of Equol in the Steroid Fraction From Sturgeon (Acipenser baeri) Plasma Using Capillary Gas Chromatography - Mass Spectrometry Catherine Pelissero and Franqoise Le Menn Groupe de Reproduction des Poissons, Laboratoire de Biologie Marine, Universite de Bordeaux I, Avenue des Facultes, 33405 Talence Cedex, France Philippe Garrigues UA 348 CNRS Universite de Bordeaux I, 33405 Talence Cedex, France Equol, which is a derivative of the vegetal isoflavone formononetin and obtained by bacterial degradation in the digestive tract of mammals fed on a vegetal diet, has been detected in the plasma of sturgeon fed on a soya-based fish diet. </p><p>Such a compound, which is a structural analogue of certain sexual steroids, e.g., estradiol, has been demonstrated to have an estrogenic activity in several mammals and as such it could also be responsible for the secretion of vitellogenin by hepatocytes in male sturgeons. </p><p>A combined analytical procedure involving several liquid chromatographic separations and capillary gas chromatography - mass spectrometry with chemical ionisation led to the detection of equol in estradiol extracts from fish plasma. Keywords: Equol; sturgeon; capillary gas chromatography; mass spectrometry; chemical ionisation Recent interest in the presence of drugs and xenobiotic compounds in animal or human food has led to the assessment and development of the analytical capabilities of food and toxicology laboratories. For these purposes, gas chromato- graphy - mass spectrometry with electron ionisation (EI) or, chiefly, chemical ionisation (CI) offers important advantages for the identification and determination of many drugs. </p><p>Equol (Fig. 1) has been proven to be present in large amounts in the excretions (urine, faeces) of mammals such as horses and goats and also in man.14 It has been demonstrated that this compound is formed by the bacterial degradation of dietary isoflavones (daidzein, formononetin; see Fig. 1) present in vegetals.5-9 As it is structurally related to sexual steroids, equol was found to have an effect on estrogen receptors in mammals. 1 ~ ~ 3 1 0 ~ ~ Vitellogenin, known to be induced by estrogens, has been detected in the plasma of male sturgeons fed on an artificial diet for trout containing about 20% of soya extract.12 In a preliminary approach, we correlated the abnormal presence of vitellogenin to a sexual steroid dietary contamination.12 The aim of this paper was to detect the presence of isoflavone metabolites in plasma, known for their estrogenic property and originating from the vegetal part of the diet. </p><p>To our knowledge no data on the detection of such a compound have been reported in lower vertebrates, although some studies have described the mascu- linisation of fish by phytosterols.13J4 In the work reported here, we describe the detection of equol in plasma from cultured sturgeon fed on a soya enriched semi-synthetic diet devoid of sexual estrogens. Capillary gas chromatography coupled to mass spectrometry (GC - MS) used in the CI mode has been performed on estradiol plasma extracts and its applicability to the detection of compounds closely related to estrogens in fish plasma extracts has been demonstrated. Experimental Sample Preparation Sturgeons from a fish farm were fed on a fish diet containing 30% casein, 30% soya with “amidon,â€� fish oil, vitamins and salts. </p><p>The fish plasmas were extracted as described by Fostier OH- \ OCHB 0 Formo no net i n (M, 270) 0 Daidzein ( Mr 254) Equol (Mr 242) Fig. 1. Structures of equol and its principal precursors in soya1704 ANALYST, DECEMBER 1989, VOL. 114 and Breton. 15 Liquid extraction was performed with cyclohex- ane - ethyl acetate (50 + 50). The extracts collected were then submitted to open liquid column chromatography on a Sephadex LH-20 column (8 x 0.5 cm i.d.) with dichloro- methane - methanol (95+5) as eluent. The fraction corre- sponding to the elution of estradiol was collected, evaporated to dryness, stored in ethanol and kept at -20 "C for further GC or GC - MS analyses.16 Equol reference samples were kindly donated by H. </p><p>Adlercreutz (University of Helsinki, Finland) and C. Jordan (University of Wisconsin, USA). Gas Chromatographic Analyses Capillary gas chromatography with flame ionisation detection (FID) was performed on a Carlo-Erba Model 4160 chromato- graph equipped with a splitless injector and a flame ionisation detector. Analyses were carried out on a CPSil8 CB capillary column (50 m x 0.25 mm i.d.) with helium as the carrier gas m/z Fig. 2. Chemical ionisation mass spectra of equol (a) as a reference standard and ( b ) as the compound isolated in the estradiol extract from sturgeon plasma and with the following temperature programme: initial temperature 50 "C, then up to 220 "C at 10 "C min-1 and then to 310 "C at 2 "C min-1. </p><p>A capillary chromatograph (Varian 3300) coupled to an ion trap detector (Finnigan) in the CI mode with isobutane as the ionisation gas was used for the equol reference sample. Analyses were carried out on a DB5 column (J and W; 30 m x 0.25 mm i.d.) with the temperature programme described above. Results and Discussion Although the mass spectrometric analysis of equol has often been performed with its trimethylsilyl ether derivative , only one paper17 has reported the mass spectrum of the free compound obtained in the EI mode. Under CI, equol exhibits a mass spectrum with five major peaks at 243 ( M + 1,71), 242 (M+, 68), 123 (loo), 120 (28) and 107 (44%) as shown in Fig. </p><p>2. The peaks correspond to the fragmentation scheme shown in Fig. 3. The GC - FID trace of the estradiol fraction from a fish plasma shows several peaks as shown in Fig. 4. Some of the peaks have been identified as contaminants (phthalates) owing to the method of blood sampling of the fish. A small peak observed on the GC - FID trace could be attributed to equol according to the retention time. This was confirmed by GC - MS; the peak exhibited a spectrum profile similar to the equol standard in Fig. 2(a). It was determined that about 5 ng of equol were present in 200 p1 of an estradiol extract from fish plasma. The detection of equol would suggest the presence, in the gastrointestinal tract of sturgeon, of a microflora capable of biologically degrading isoflavones (such as daidzein or formo- nonetin) to form equol as suggested previously.7~18 As gastrointestinal microflora are considered to be limited in fish compared to mammals, the degradation of equol precursors is probably not complete, consequently daidzein or formonon- etin must also be looked for in fish plasmas. </p><p>Conclusion Equol has been identified for the first time in the plasma of lower vertebrates by mass spectrometry with chemical ionisa- tion. This indicates that isoflavones of soya contained in fish diets could be transformed into weak estrogenic compounds by the microflora of the digestive tracts of fish. The presence of equol could probably have an influence on the sexual Fig. 3. Fragmentation scheme of equol as suggested by the major ions observed in the C1 mass spectrumANALYST, DECEMBER 1989, VOL. 114 1705 0 Cholesterol L 20 40 Retention time/min Fig. </p><p>4. phthalate contaminants (B). A, Equol Chromatogram obtained from the estradiol extract from sturgeon plasma (FID). Note the significant amount of cholesterol and function of cultured animals. Moreover, the presence of isoflavone metabolites in fish plasma indicates that the dietary contamination is probably a more complex process involving both animal estrogens and vegetal estrogenic compounds. We are grateful to Cemagref (Cestas) for the gift of the sturgeons and to Dr. S. Kaushik from the INRA Laboratory of Nutrition Fish (St P6e sur Nivelle) for the soya enriched semi-synthetic diet. We are also indebted to E. Choquetand E. G6nin from Finnigan-Mat (Orsay) for the GC - MS facilities. </p><p>D. Dessort (Elf-Aquitaine, Pau) is also acknow- ledged for helpful discussions on GC - MS data. We also thank Ph. Lighfoot for careful reading of the manuscript. References 1. Thompson, M. A., Lasley, B. A., Rideout, B. A., and Kasman, L. H., Biol. Reprod., 1984,31, 705. 2. Axelson. M., Kirk, D. N., Farrant, R. D., Gooley, G., Lawson, A. M., and Setchell, K. D. R., Biochem. J . , 1982,201, 353. 3. Kaziro, R., Kennedy, J . P., Cole, E. R., and Southwell-Keely, R. T., J. Endocrinol., 1984, 103, 395. 4. Tang, B. Y., and Adams, N. R., J. Endocrinol., 1980,85,291. 5. Axelson, M., Sjovall, J., Gustafsson, B. E., and Setchell, K. D. R., Nature (London), 1982, 298, 659. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. Biggers, J . D., and Curnow, D. H., Biochem. J., 1954,58,278. Axelson, M., Sjovall, J., Gustafsson, B. E., and Setchell, K. D. R., J. Endocrinol., 1984, 102, 49. Shutt, D. A., and Braden, A. W. H.,Aust. J. Agric. Res., 1968, 19, 545. Braden, A. W. H., Hart, N. K., and Lamberton, J. A., Aust. J . Agric. Res., 1967, 18, 335. Adlercreutz, H., Fotsis, T., Bannwart, C., Wahala, K., Makela, T., Brunow, G., and Hase, T., J. Steroid Biochem., 1986, 25, 791. Adlercreutz, H., Hockerstedt, K., Bannwart, C., Bloigu, S . , Hamalainen, E., Fotsis, T., and Ollus, A., J. Steroid Biochem., 1987, 27, 1135. Pelissero, C., and Le Menn. F., C. R. Acad. Sci. skrie I l l , 1988, 307, 749. Howell, W. M., Black, D. A., and Bortone, S. A., Copeia, 1980, 4, 676. Hunsinger, R. H., Byram, B. R., and Howell, W. M., J . Fish Biol., 1988, 32, 795. Fostier, A., and Breton, B., J. Steroid Riochem., 1975,6,345. Pelissero, C., Thkse de 3" cycle, Universite de Bordeaux, 1988. Hayashi, Y., Shirato, T., Sakurai, K., and Takahashi, T., Mokuzai Gakkaishi, 1978, 24, 898. Shutt, D. A., Endeavour, 1976, 35, 110. Paper 91034221 Received August 23rd, 1989</p></section></art-body></article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>Communication. 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Such a compound, which is a structural analogue of certain sexual steroids, e.g., estradiol, has been demonstrated to have an estrogenic activity in several mammals and as such it could also be responsible for the secretion of vitellogenin by hepatocytes in male sturgeons. A combined analytical procedure involving several liquid chromatographic separations and capillary gas chromatography-mass spectrometry with chemical ionisation led to the detection of equol in estradiol extracts from fish plasma.</abstract><relatedItem type="host"><titleInfo><title>Analyst</title></titleInfo><titleInfo type="abbreviated"><title>Analyst</title></titleInfo><genre type="journal">journal</genre><originInfo><publisher>The Royal Society of Chemistry.</publisher></originInfo><identifier type="ISSN">0003-2654</identifier><identifier type="eISSN">1364-5528</identifier><identifier type="coden">ANALAO</identifier><identifier type="RSC sercode">AN</identifier><part><date>1989</date><detail type="volume"><caption>vol.</caption><number>114</number></detail><detail type="issue"><caption>no.</caption><number>12</number></detail><extent unit="pages"><start>1703</start><end>1705</end><total>3</total></extent></part></relatedItem><identifier type="istex">8018B8BBE055D8F58DF20BF6D7400924676A43C8</identifier><identifier type="DOI">10.1039/AN9891401703</identifier><identifier type="ms-id">AN9891401703</identifier><accessCondition type="use and reproduction" contentType="copyright">This journal is © The Royal Society of Chemistry</accessCondition><recordInfo><recordContentSource>RSC Journals</recordContentSource><recordOrigin>The Royal Society of Chemistry</recordOrigin></recordInfo></mods></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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|texte= Communication. Detection of equol in the steroid fraction from sturgeon (Acipenser baeri) plasma using capillary gas chromatography-mass spectrometry
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