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And Its Metabolites Urine by LC/APCI/MS and GC/MS Determination ofAdrenosterone and its Metabolites Bull. Korean Chem. Soc. 2009, Vol. 30, No. 7 1489 Determination of Adrenosterone and its Metabolites in Human Urine by LC/APCI/MS and GC/MS Eunjung HanJ* Okkyoung Yim,t Sun-young Beak「Jaeyeon Chung「Ji-hye Lee「Jungahn Kim,* and YUnje Kim” ‘Korea Institute of Science and Technology, P. O. Box 131, Cheongryang, Seoul 136-791, Korea. * E-mail: [email protected] * Department of Chemistry, Kyunghee University, Seoul 130-701, Korea Received March 16, 2009, Accepted May 11, 2009 This study was done for the determination and excretion profile of adrenosterone and its metabolites in human urine using both liquid chromatography with atmospheric pressure chemical ionization mass spectrometry and gas chromatography with mass spectrometry. Adrenosterone and its two metabolites were detected in human urine after administration a healthy volunteer with 75 mg of adrenosterone. We found that adrenosterone -M1 (C19H26O3) was a reduction and adrenosterone -M2 (C19H26O4) was a hydroxylation at C-ring, which did not know the exact position of the C-ring. The adrenosterone parent was detected by GC/TOF-MS, but not detected by LC/APCI/MS because of low intensity. Adrenosterone and its two metabolites were excreted as their glucuronided fractions. The recovery of this method ranged from 100.7 to 118.4% and the reproducibility and accuracy test were 85.5 to 112.0% and 1.1 to 8.4%, respectively. The excretion studies showed that adrenosterone and its metabolites were detectable in human urine during a 48 h period after oral administration, with maximum level of excretion at 4.1 h. The glucuro-/sulfa- conjugated ratio of adrenosterone, M1 and M2 was 0.73 士 0.03, 0.96 士 0.06 and 0.89 士 0.03 (n = 6), respectively. The amounts of adrenosterone excreted in urine were 14.75 ng for 48 h. Also, the maximum level of androsterone and 11p-hydroxy androsterone, which were endogenous steroids, were reached 4.1 h after the oral administration of adrenosterone. Key Words: Adrenosterone, Metabolites, LC/APCI/MS, GC/MS Introduction derivatization for their analysis.11-14 More recently, liquid chro- matography/mass spectrometry (LC/MS) has been used for Anabolic-androgenic steroids (AAS) have been widely used trace bioanalysis.15-18 This technique allows highly sensitive as therapeutic agents for restoring muscle strength and increas­ determinations without derivatization as required for GC/MS. ing muscle size.1,2 However, abuse of AAS causes many It is also possible to devise methods in specificity for meta­ adverse effects in several organs systems, particularly the liver bolites and structurally similar compounds.19 and heart.3, 4 The present work reports a method to detect the metabolites Over the last decade, a number of certain type of anabolic of adrenosterone in human urine after oral administration, steroids, so called prohormones, have become available in the using both LC/MS and GC/MS as methods for screening and United States as nutritional supplements.5 The term “prohorm­ confirmation. The determination of the adrenosterone parent one” is used because initially these substances were precursors and its metabolites in human urine was also studied. In of testosterone (T) or nortestosterone. These products Supple­ addition, we studied the excretion profile of adrenosterone ment Health and Education Act, although the recently are sold and its metabolites after oral administration. as over-the-counter products under the 1994 Dietary signed “Anabolic steroid Control Act of 2004” is intended to put a Experiment시 ban on these substances. Global distribution via the internet has resulted in a huge international commercial success for Chemicals. Adrenosterone (androst-4-ene-3,11,17-trione) products including androst-4-ene-3,17-dione (AD), 19-noran- and 17-methyltestosterone (used as an internal standard) were drostenedione and dehydroepiandrosterone. The use of these purchased from Sigma Chemical Co. (MO, USA). Adreno- substances constitutes a doping offence according to the regu­ steorne tablets were purchased from Ergopharm (Champaign, lations6 of the World Anti-Doping Agency (WADA). IL, USA). Serdolite® PAD-1 resin (particle size 0.1-0.2 mm) In general, adrenosterone (androst-4-ene-3,11,17-trione, was supplied by Serva Co. (Heidelberg, Germany) and was Fig. 1), a tri-ketosteroid, was isolated from the cortical extracts washed with acetone, methanol and distilled water before use. by Reichstein.7 Adrenosterone exhibits a variety of biological KH2PO4 and K3PO4 were obtained from KANTO Chemical properties such as androgenic properties and activities.8,9 It Co (Tokyo, Japan). p-Glucuronidase was obtained from Roche also possesses aromatase (estrogen synthetase) inhibitory Diagnostics (Mannheim, Germany). Diethyl ether and ace­ activity which plays an important role managing the estrogen- tonitrile were purchased from J. T. Baker (Phillipsburg, MT, mediated events especially in ovulation and the growth of USA). Ammonium acetate was purchased from YAKURY estrogen-dependent tumors.10 Chemical Co (Tokyo, Japan). Acetonitrile and distilled water Generally, metabolites in urine are polar, so it is not easy to were used after filtering through Millipore filters (0.45 卩m, use gas chromatography/mass spectrometry (GC/MS) without MA, USA) and sonication for 20 min. N-Methyl-N-trimethyl- 1490 Bull. Korean Chem. Soc. 2009, Vol. 30, No. 7 Eunjung Han et al Table 1. Operating conditions for LC/APCI/MS Table 2. Operating conditions for GC/MS LC conditions GC conditions Column : Capcell Pak, Type UG120, C18 Column : Ultra-2 (150 mm x 2.0 mm i.d., particle size 5 pm) (cross-linked 5% phenylmethylsiloxane, Flow rate : 0.2 mL/min 0.2 mm i.d. x 25 mm length x 0.11 pm film thickness) Mobile phase Carrier gas : He at 1.0 mL/min solvent A 10 mM acetic acid in D.W Oven temperature program : solvent B 10 mM acetic acid in Acetonitrile Rate (oC/min) Temp. (oC) Hold(min) Gradient time table 180 1 Time (min) 0 3 7 9 10 20 260 0 A solvent (%) 75 50 50 20 75 10 325 2 B solvent (%) 25 50 50 80 25 Run time : 14.50 min Run time : 13 min Injection volume : 2 卩 L Injection volume : 10 pL Injection port temperature : 280 oC Column temperature : 45 oC Transfer line temperature : 280 oC MS conditions TOF-MS conditions Ionization method: APCI Source temperature : 230 oC Ionization mode : positive ion mode mass range : m/z 100 〜650 Corona current : 5 uA Scan rate : 10 spectra/sec Desolvation gas flow : 1000 cc/min (N2) Nebulizer pressure : 410 kPa MSD conditions Desolvation gas temperature : 400 oC Source temperature : 230 oC Scan range : m/z 100 〜400 mass range : m/z 100 〜650 Scan rate : 6.25 spectra/sec Acquisition mode : SIM (Selected Ion Monitoring) mode Selected ion (m/z): 301, 411,413, 446, 501, 503, 516, 518, 589, silyltrifluoroacetamide (MSTFA), ammonium iodide (NH4I) 604 and dithioerythritol (DTE) were obtained from Sigma. Instruments and equipment. The LC/TOF-MS system, con­ PAD-1 resin until a bead height of 1.5 cm was achieved. The sisted of an HP 1100 series LC with an atmospheric pressure column was washed with 2 mL of distilled water and then 3 chemical ionization (APCI) source from Agilent Technologies mL of a urine sample spiked with 17-methyltestosterone (50 pL, (Palo Alto, CA, USA) and TOF-MS from LECO (St. Joseph, 10 pg mL-1) as the internal standard was passed through the MI, U SA), was used for the separation and estimation of the column. The adsorbed sample was washed with 2 mL of dis­ molecular weights of metabolites. Liquid chromatographic tilled water and eluted with 4 mL of methanol. The collected separation was done on a Capcell Pak C18 column (150 mm x solution was evaporated with a rotary evaporator, and the 2.0 mm i.d., particle size 5 卩m) from Shiseido (Chuoku, Japan). residue was dissolved in 1 mL of phosphate buffer (0.2 M, pH The 6890N GC from Agilent with TOF-MS from LECO was 6.8). used to detect suspected metabolites. 6890N GC-5975 MSD P-Glucuronidase (50 pL) was added and the solution was from Agilent was used for the excretion studies for adre­ heated at 55 oC for 1 h in order to hydrolyze the glucuronide nosterone and its urinary metabolites. The column was an Ul­ conjugate. After hydrolysis and cooling to room temperature, tra-2 cross-linked 5% phenylmethylsiloxane capillary column 5 mL of ether was added, and then the mixture was shaken for (25 m x 0.2 mm i.d., 0.11 卩m film thickness). Operating con­ 10 min and centrifuged at 2500 rpm for 5 min. The organic ditions for LC/APCI/MS and GC/MS are shown in Tables 1 layer was transferred to another test tube and then concentrated and 2, respectively. at 40 oC under a gentle stream of nitrogen. The residue was HS501D shaker from IKA (Staufen, Germany) for liquid dissolved in 100 pL of methanol, and 10 pL was injected into extraction, Varifuge-F from Heraeus (Hanau, Germany) for the LC/APCI/MS. centrifugation, vortex mixer from Scientific Industry (Bohe­ The ratio of free, glucuro- and sulfa-conjugaed forms of mia, USA), Turbovap® LV evaporator from Zymark (Hopkin­ adrenosterone and its metabolites were studied to the excreted ton, MA, U SA) and WB 2000 evaporator from Hiedolph (Sch- forms. wabach, Germany) for sample concentration, and ecoline Trimethylsilylation forGC/MS. For characterization of adre­ RE112 Freezer from LAUDA (Lauda-Konogshofen, Ger­ nosterone and its urinary metabolites proposed by GC/MS, many) to take organic layer from extraction procedure were the residue was dried in a vacuum desiccator for 30 min. The used. dried residue was dissolved in 50 pL of MSTFA/NH4I/ DTE Volunteer sample.
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