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Anabolic-Androgenic Steroids in Horses: Natural Presence and Underlying Biomechanisms

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Anabolic-Androgenic Steroids in Horses: Natural Presence and Underlying Biomechanisms ANABOLIC-ANDROGENIC STEROIDS IN HORSES: NATURAL PRESENCE AND UNDERLYING BIOMECHANISMS Anneleen Decloedt Dissertation submitted in the fulfilment of the requirements for the degree of Doctor of philosophy (PhD) in Veterinary Sciences, Faculty of Veterinary Medicine, Ghent University PROMOTER Prof. dr. ir. Lynn Vanhaecke Ghent University, Faculty of Veterinary Medicine Department of Veterinary Public Health and Food Safety Laboratory of Chemical Analysis MEMBERS OF THE READING COMMITTEE Prof. dr. James Scarth HFL Sport Science, Cambridgeshire, United-Kingdom Prof. dr. Peter Van Eenoo Ghent University, DoCoLab, Zwijnaarde, Belgium Prof. dr. Ann Van Soom Ghent University, Faculty of Veterinary Medicine, Merelbeke, Belgium MEMBERS OF THE EXAMINATION COMMITTEE Dr. Ludovic Bailly-Chouriberry Laboratoires des Courses Hippiques, Verrières-le-Buisson, France Dr. Leen Van Ginkel Wageningen University, RIKILT, Wageningen, The Netherlands Prof. dr. Myriam Hesta Ghent University, Faculty of Veterinary Medicine, Merelbeke, Belgium This work was funded by the Fédération Nationale des Courses Françaises (via the Laboratoire des Courses Hippiques) and executed at the Laboratory of Chemical Analysis (Faculty of Veterinary Medicine, Ghent University, Merelbeke). The author and the promoter give the authorisation to consult and to copy parts of this work for personal use only. Every other use is subject to the copyright laws. Permission to reproduce any material contained in this work should be obtained from the author. “The universe is full of magic, Just patiently waiting for our wits to grow sharper” TABLE OF CONTENTS TABLE OF CONTENTS Chapter I – General Introduction 1 1. Steroids 3 1.1 Chemical structure 1.2 (Steroid) hormones and their role in the endocrine system 1.3 Biosynthesis of steroid hormones 1.4 Anabolic-androgenic steroids (AAS) 1.5 Synthesis and absorption of the steroid precursor cholesterol 2. Anabolic steroid abuse 12 2.1 Scientific history of anabolic steroid abuse 2.2 Residue-analysis in farm animals: regulations 2.3 Doping regulations: humans and horses 2.4 Sex steroids as registered drugs 3. Endogenous steroids 17 3.1 Reference ranges for endogenous steroids in humans 3.2 Reference ranges for endogenous steroids in horses 3.3 Hormonal disorders in horses 4. Phytosterols 22 4.1 Biological role and chemical structure 4.2 Link to anabolic steroids 5. Equine digestive tract 26 5.1 Anatomical overview 5.2 Diet 6. Analytical instrumentation 29 6.1 History 6.2 Phase I and II metabolites 6.3 UHPLC-MS/MS 6.4 GC-C-IRMS i TABLE OF CONTENTS 7. Aims 36 Chapter II – Development and validation of a UHPLC-MS/MS method to quantify low levels of anabolic-androgenic steroids naturally present in urine of untreated horses 47 1. Abstract 49 2. Introduction 50 3. Material and methods 53 3.1 Chemicals and reagents 3.2 Sample collection and extraction 3.3 Hydrolysis of the glucuro- and sulfo-conjugated compounds 3.4 Solid phase extraction, washing, and solvolysis 3.5 UHPLC-MS/MS analysis 3.6 Standard addition approach and data analysis 3.7 Quality assurance: validation of the analytical method 4. Results and discussion 59 4.1 Validation study 4.1.1 Specificity 4.1.2 Selectivity 4.1.3 Linearity 4.1.4 Precision 4.1.5 Trueness 4.1.6 Stability 4.1.7 Limit of detection and quantification 4.2 Urine screening of untreated horses 5. Conclusion 69 5.1 Executive summary Chapter III – Optimisation of phytosterol extraction and analysis from feed by D-Optimal design and UHPLC-MS/MS 75 1. Abstract 77 2. Introduction 78 ii TABLE OF CONTENTS 3. Material and methods 81 3.1 LC-MS2 reagents and chemicals 3.2 Feed and food samples 3.3 Extraction protocol optimisation 3.4 UHPLC-Triple quadrupole MS/MS analysis 3.5 Data analysis and quality assurance of the analytical method: validation according to EU Council Decision 2002/657 and AOAC guidelines 3.6 Quantitative analysis of different feed and food samples 4. Results and discussion 86 4.1 Extraction protocol optimisation 4.2 Data analysis and quality assurance of the analytical method: validation according to EU Council Decision 2002/657 and AOAC guidelines 4.2.1 Specificity 4.2.2 Selectivity 4.2.3 Calibration curves 4.2.4 Trueness: recovery 4.2.5 Precision 4.2.6 Limit of detection and quantification 4.3 Quantitative analysis of different food and feed samples 5. Conclusion 99 5.1 Highlights Chapter IV – In vitro simulation of the equine hindgut as a tool to study the influence of phytosterol consumption on the excretion of anabolic- androgenic steroids 103 1. Abstract 105 2. Introduction 106 3. Material and methods 109 3.1 LC-MS2 reagents and chemicals 3.2 In vitro digestion: batch incubations 3.2.1 Buffers and broths 3.2.2 Fecal inoculum 3.2.3 Digestion protocol and sampling iii TABLE OF CONTENTS 3.2.4 Validation of the in vitro digestion protocol 3.2.5 In vitro digestion supplements 3.2.6 Bacterial strains 3.3 Extraction of in vitro digestion and urine samples 3.3.1 Hydrolysis 3.3.2 Solid phase extraction (SPE), liquid-liquid extraction and solvolysis 3.3.3 Pooling and reconstitution 3.4 UHPLC-triple quadrupole MS/MS analysis 3.5 Quantification: data analysis and quality assurance of the analytical method 4. Results 118 4.1 Quantification: data analysis and quality assurance of the analytical method 4.2 In vitro digestion: proof of principle 4.3 Blank in vitro digestion 4.4 In vitro digestions with added steroid precursors 4.5 In vitro digestions with added phytosterols or herbal supplements 5. Discussion 129 6. Conclusion 133 Chapter V – Moldy feed, a possible explanation for the excretion of anabolic-androgenic steroids in horses? 141 1. Abstract 143 2. Introduction 144 3. Material and methods 147 3.1 LC-MS/MS reagents and chemicals 3.2 Buffers, broths and feed samples 3.3 Aerobic incubation of moldy feed 3.4 Aerobic incubation of a commercial grain mix with Mycobacterium sp. 3.5 Activity of extracellular enzymes excreted by corn-related molds 3.6 In vitro digestion of moldy feed 3.7 UHPLC-Triple Quadrupole MS/MS analysis 3.8 Data analysis, quantitative and qualitative assurance of the analytical method 4. Results 155 iv TABLE OF CONTENTS 4.1 Aerobic incubation of moldy feed 4.2 Aerobic incubation of a commercial grain mix with Mycobacterium sp. 4.3 Activity of extracellular enzymes excreted by corn-related molds 4.4 In vitro digestion of moldy feed 5. Discussion 159 6. Conclusion 164 Chapter VI – Influence of glucocorticoid treatment on the excretion of anabolic-androgenic steroids: in vitro simulations and in vivo case study 171 1. Abstract 173 2. Introduction 174 3. Material and methods 176 3.1 In vivo experimental set-up 3.2 In vitro simulation of the equine hindgut: biotransformation of glucocorticoids 3.3 LC-MS reagents and chemicals 3.4 Extraction of urine and in vitro digestion samples 3.4.1 Hydrolysis 3.4.2 Solid Phase Extraction (SPE) 3.4.3 Pooling and reconstitution 3.5 Analytical methods (UHPLC-MS/MS and UHPLC-Orbitrap-HRMS) 3.6 Quantification 4. Results 182 4.1 Urinary profile after intra-articular administration of betamethasone 4.2 In vitro digestion: biotransformation of glucocorticoids 5. Discussion 184 Chapter VII – General Discussion and Future Perspectives 191 1. Positioning of the research 193 1.1 Economical relevance of horse sports and racing v TABLE OF CONTENTS 1.2 Anabolic steroid abuse: back to the future? 1.3 Endogenous AAS: complicating doping analysis 1.4 Analytical methods to detect (endogenous) steroid abuse 2. Scientific contributions and research findings 198 2.1 Development and validation of a UHPLC-MS/MS method to quantify low levels of AAS naturally present in urine of untreated horses 2.2 Extraction optimisation, development and validation of a UHPLC-MS/MS method for the detection and quantification of phytosterols in feed 2.3 Validation of an in vitro digestion simulation of the equine hindgut as a tool to study the influence of phytosterol consumption on the excretion of anabolic- androgenic steroids in horses 2.4 Moldy feed, a possible explanation for the detection of anabolic-androgenic steroids in horses? 2.5 Influence of glucorticoid treatment on the excretion of anabolic-androgenic steroids in equine urine 3. Future perspectives 211 3.1 Endogenous steroid formation 3.2 Dietary contamination and transformation 3.3 Phytosterol-enriched feed consumption: in vivo 3.4 Mashes and silage 3.5 Influence of glucocorticoid treatment on the excretion of AAS 3.6 Equine Biological Passport Summary 225 Samenvatting 231 CV 237 Dankwoord 247 vi NOTATION INDEX NOTATION INDEX 17β-HSD 17β-hydroxysteroid dehydrogenase enzyme ∆1-SDH delta-1-steroid dehydrogenase %RSD Relative Standard Deviation αBol α-Boldenone; 17α-hydroxy-1,4-androstadiene-3-one AAS Anabolic-Androgenic Steroids ABP Athlete Biological Passport Ac-CoA Acetyl-Coenzyme A ACAT Acetyl-CoA Acetate Transferase ACTH Adrenocorticotropic hormone ADD Androstadienedione; boldione; androsta-1,4-diene-3,17-dione ADF Acid Detergent Fibre AED Androstenedione; androst-4-ene-3,17-dione AL Anterior Lobe (of the pituitary gland) AOAC Association of Official Analytical Chemists AORC Association of Official Racing Chemists ARB Australian Racing Board ASG Acylated Steryl Glycosides (phytosterol conjugates) au Arbitrary Units BCFIvet “Belgisch Centrum voor Farmacotherapeutische Informatie” BHI Brain Heart Infusion BM1 5β-androst-1-en-17β-ol-3-one BSE Bovine Spongiform Encephalopathy ßBol ß-boldenone; 17ß-hydroxy-1,4-androstadiene-3-one ßT ß-testosterone; 17ß-hydroxy-4-androstene-3-one CD Council Decision CE Collision Energy CEC Capillary Electro Chromatography CID Collision Induced Dissociation CHRB Canadian Horse Racing Board CP Crude Protein CPB Cystein Peptone Bouillon CRH Corticotrophin-releasing hormone CRM Certified Reference Material vii NOTATION INDEX DHEA Dehydroepiandrosterone DHT Dihydrotestosterone DM Dry Matter DOE Design of Experiments d.w.
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