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Gas Chromatographic/Mass Spectrometric Analysis of 19-Nortestosterone Urinary Metabolites in Cattle Etienne Benoit, J.L

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Gas Chromatographic/Mass Spectrometric Analysis of 19-Nortestosterone Urinary Metabolites in Cattle Etienne Benoit, J.L Gas chromatographic/mass spectrometric analysis of 19-nortestosterone urinary metabolites in cattle Etienne Benoit, J.L. Guyot, D. Courtot, P. Delatour To cite this version: Etienne Benoit, J.L. Guyot, D. Courtot, P. Delatour. Gas chromatographic/mass spectrometric anal- ysis of 19-nortestosterone urinary metabolites in cattle. Annales de Recherches Vétérinaires, INRA Editions, 1989, 20 (4), pp.485-491. hal-00901913 HAL Id: hal-00901913 https://hal.archives-ouvertes.fr/hal-00901913 Submitted on 1 Jan 1989 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Original article Gas chromatographic/mass spectrometric analysis of 19-nortestosterone urinary metabolites in cattle E. Benoît J.L. Guyot D. Courtot P. Delatour 1 INRA, Laboratoire No. 54i89, service de biochimie, Ecole Nationale Vétérinaire de Lyon, BP 31, 69752 Charbonnières Cedex; 2 INRA-ENVL, laboratoire de recherches sur le cheval de sport, Ecole Nationale Vétérinaire de Lyon, BP 31, 69752 Charbonnières Cedex, France (received 31 May 1988, accepted 18 January 1989) Summary ― Gas chromatographic and mass spectrometric method is used to confirm the administration of 19-nortestosterone to cattle. The most abundant metabolites detected were 19- norepitestosterone and 5a-oestrane-3p,17a-diol. gas chromatography ― mass spectrometry - 19-nortestosterone - metabolite - urine - cattle Résumé ― Etude par chromatographie en phase gazeuse couplée à la spectrométrie de masse des métabolites urinaires de la 19-nortestostérone chez les bovins. La chromatographie en phase gazeuse couplée à la spectrométrie de masse permet de confirmer l’administration, actuellement interdite dans l’ensemble de la CEE, de 19-nortestostérone chez les bovins, par la mise en évidence de différents métabolites urinaires caractéristiques, tels que la 19- norépistestostérone et le 5 o’-œsffane-3j3,17o!-d/o/. chromatographie en phase gazeuse ― spectrométrle de masse ― 19-nortestostérone - métabolite - urine - bovin INTRODUCTION it has also been used for non-therapeutic purposes; in humans to improve athletic performance, or in the veterinary field as a 19-Nortestosterone (19-NT), and its growth promoting agent to accelerate and esters, are synthetic anabolic steroids weight gain improve feeding in cattle. which are widely used as therapeutic efficiency agents. Since 19-NT promotes an in- On the basis of their toxic and creased formation of tissue protein, while hormone-like side effects, administration being less androgenic than testosterone, of anabolic steroids for zootechnical purposes in cattle has been banned Steroids throughout the EEC. However, it is generally agreed that the control of the Testosterone, epitestosterone, and 19-NT were illegal use of anabolic steroids is effective obtained from Sigma Chemical Co. (St Louis, only if sensitive and specific tests are MI, USA). 19-NT Undecanoate (Trophobo- used for the detection and identification of lene@) was kindly donated by Theramex (France). 5a-Estrane-30, 17-a-diol was kindly these drugs or their metabolites in urine. supplied from the Racecourse Security Service In the absence of such methods adapted Laboratory (Newmarket, England). 3,4-13C to cattle, it seems that 19-NT is widely testosterone was obtained from CEA (Gif-sur- used (Jansen et aL, 1985). Yvette, France). Methods based on radioimmunoassay (RIA) have been developed for the detection of 19-nortestosterone in man Animals, treatment and biological (Bosch, 1984; Belkien et aL, 1985), and in samples animal (Chapman et al., 1982; Benoit et aL, But due to their relative lack of 1985). Four adult friesian cows and four 2-month-old RIA methods can be used specificity, only calves were used in this study. They received a for screening purposes and positive single intramuscular injection of 1 mg of identification of steroids has to be nandrolone undecanoate per kg body weight. Urine were obtained to performed by combined gas chromato- samples prior administration, and 15 days thereafter, by and mass graphy spectrometry. catheterisation of the bladder or following This paper describes an analytical natural micturition. In one adult cow, urine was methodology developed for the isolation collected three days after administration. Urines were stored frozen at - 30 °C, until analysed. and identification of different urinary metabolites of 19-NT undecanoate in cattle using high resolution gas chromatography combined with mass Isolation procedure of urinary steroids spectrometry. Urine (10 ml), added with testosterone !3C (0,25 wg) as an internal standard, was slowly passed through a Seppak C18, followed by a 10-ml wash with water. The free and MATERIALS AND METHODS conjugated steroids were recovered by elution with 10 ml of methanol. The methanolic eluate was evaporated to dryness at 40 °C under vacuum. The residues were dissolved in 5 ml of M sodium acetate buffer Chemical and solvents 0.2 (pH 5.2), containing 200 ml of Helix pomatia digestive juice. After incubation at 37 °C for 16 h, pH was Solvents were of analytical grade and were adjusted to 10 with NaOH N. The hydrolysate distilled before use. Heptafluorobutyric was then passed through an Estrogen column, anhydride (HFBa) was purchased from Pierce followed by 5 ml wash with water. The neutral Chemical Co., Rockford, IL, USA. Helix steroids were eluted by 5 ml of methanol. The pomatia digestive juice was obtained from IBF methanolic eluate was evaporated to dryness (France). SepPack C18 and Estrogen Column then redissolved with 60 gl of methanol/ (AG1-X2) was obtained from Waters (Milford, diethyl!ther (1/1). The total solution was MS, USA) and BioRad (Spiral, Dijon, France), applied on a thin-layer chromatographic (TLC) respectively. Thin layer plate silica gel was plate, previously washed with the eluant purchased from Merck (Kieselgel 60 F254, [benzene/ethyl―acetate (70/30)]. Migration of Darmstadt, FRG). up to 15 cm was allowed. The silica gel zone, corresponding to the migration of a mixture of were maintained, respectively, at 180 °C and steroids such 17a-methyltestosterone, epi- 290 °C, and the electron energy was set at 70 testosterone and dehydrotestosterone, was eV. Electron impact mass spectra were recuperated and eluted with 1 ml of acetone. recorded from 120 uma to 700 uma at a speed of 1 ms/uma. Preparation of derivatives The acetone eluate was evaporated to dryness, RESULTS dissolved in 50 wl of acetone, and then 10 III of HFBa was added. The mixture was left for 155 min at room temperature, then evaporated to We were interested only in steroids which dryness. The derivatives were recovered with were not observed in urine sample 50 wl of anhydrous benzene. collected prior to administration of the anabolic steroid. The presence of steroids derived by a reductive process, or by Gas chromatographylmass spectro- epimerisation, from the structure of metry nandrolone were investigated (i.e. 3-oxo- estr-4-ene-17-ol, estr-4-ene-3,17-diol and Gas chromatographic/mass spectrometric estrane-3,17-diol). analyses were carried out using a NERMAG R The total ion chromatogram and 10.10 B with a GIRDEL instrument, equipped ion current chromatograms for 31 gas chromatograph. The analyses were run fragment ions at m/z 666 ion of 19-NT on a SE-30 fused silica capillary column (25 m (molecular x 0.32 mm). Helium was used as the carrier diHFB derivative), corresponding to gas at a speed of 50 cm/s. Injection port was steroids extracted from a urine sample held at 250 °C. A sample volume of 2 pl was collected three days after administration into the column a solid injected through injector. of 19-NT undecanoate, is presented in The temperature was programmed from 180-230 °C at 3 °C/min. The ion source tem- Figure 1. Fragment ion current chromato- perature and the interface oven temperature gram for ions at m/z 666 shows the presence of two characteristic peaks. found with the other characteristic ions of Structural identification of compound B estranediol di HFB derivatives. was ascertained by comparison of its Nevertheless, in the mass spectrum of mass spectrum and retention time with compound C and D, the relative intensity those of authentic 19-NT di HFB of ion at m/z 670 seems to be too derivative. Mass spectrum, but not important in comparision with reference retention time, was identical to 19-NT di estranediol; as a result, we are of the HFB derivative. However, the relative opinion that only compounds E-I are retention time of compound A, in isomeric steroids. Relative retention time comparison to that of compound B, (19- of compoundI in comparision to NT) (0.89) was similar to relative retention compound G (0.868) is consistent with a time of authentic epitestosterone di HFB hypothetical structure 5a-estrane-3p,17p- derivative, in comparison to authentic di HFB derivative but its intensity is too testosterone di HFB derivative (0.89). In weak to permit us to observe a complete consequence, compound A is believed to mass spectrum; the same problem occurs be 19-norepitestosterone di HFB. Relative with compound I. From quantitative point concentration of 17a derivative was more of view, compound G (5a-estrane-3I3,17a- important (x 7) than 17P derivative. diol) appears to be the most important. Fragment ion current chromatograms The presence of A4-estrene-3,17-diol for ions at m/z 456 (most prominent ion of di HFB derivative was also examined, but estranediol diHFB derivative), corres- the standard of these isomeric steroids is ponding to steroids extracted from the not commercially available.
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