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Thesis Reference Thesis The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from precursors to odorous volatiles TROCCAZ, Myriam Abstract A côté des stéroïdes et des acides gras, une troisième classe de molécules ayant un seuil de perception très faible, les sulfanylakanoles, contribuent à l'odeur caractéristique de la transpiration humaine. Ce travail de thèse a permis l'identification de la bactérie S. haemolyticus, comme capable de générer le (R) et le (S)-3-methyle-3-sulfanylhexan-1-ole (forme majoritaire, ayant une odeur d'oignon) après incubation avec un conjugué de la cystéine et de la glycine présent dans les secrétions axillaires. Les enzymes de S. haemolyticus issues du gene metC tel que la cytathionine β-lyase ont peu d'implication dans cette transformation. Etonnamment, le ratio entre la concentration des précurseurs acides (conjugés de la glutamine) et des précurseurs soufrés est trois fois plus important chez l'homme que chez la femme. Des analyses sensorielles ont confirmé le caractère essentiel de la composition de la sueur sur le développement des odeurs corporelles qui sont ensuite modulées par la flore cutanée. Reference TROCCAZ, Myriam. The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from precursors to odorous volatiles. Thèse de doctorat : Univ. Genève, 2009, no. Sc. 4102 URN : urn:nbn:ch:unige-45634 DOI : 10.13097/archive-ouverte/unige:4563 Available at: http://archive-ouverte.unige.ch/unige:4563 Disclaimer: layout of this document may differ from the published version. 1 / 1 UNIVERSITE DE GENEVE Section des Sciences Pharmaceutiques FACULTE DES SCIENCES Laboratoire de pharmacie galénique Professeur Gerrit Borchard et de biopharmacie Département Recherche en Biotechnologie FIRMENICH SA Laboratoire de microbiologie Docteur Anthony Clark The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from precursors to odorous volatiles THESE présentée à la Faculté des sciences de l‘Université de Genève pour obtenir le grade de Docteur ès sciences, mention interdisciplinaire par Myriam TROCCAZ de Arles (Bouches du Rhône, France) Thèse N°4102 GENEVE Atelier d‘impression ReproMail 2009 UNIVERSITY OF GENEVA / FIRMENICH SA The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from precursors to odorous volatiles Au bout de tout savoir et de tout accroissement de notre savoir, il n’y a pas un point final, mais un point d’interrogation. Herman Hesse (1877-1962) UNIVERSITY OF GENEVA / FIRMENICH SA The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from precursors to odorous volatiles Table of Contents List of Abbreviations………………………………………………………………………………………………………………iii Summary of Thesis………………………………………………………………………………………………………………...vii Résumé de Thèse…………………………………………………………………………………………………………………...xiii 1. INTRODUCTION ............................................................................................................................................ 1 1.1. GENERAL PICTURE OF HUMAN BODY ODORS ……………………………………………………………………………………..3 1.1.1. Human skin: structure and function ……………………………………………………………………………………………………..….3 1.1.2. Sweat glands present on skin …………………………………………………………………………………………………………..………4 1.1.3. Factors influencing human body odors …………………………………………………………………………………………..……..…7 1.1.4. Odorous axillary volatiles ……………………………………………………………………………………………………………….….….13 1.2. BACTERIAL TRANSFORMATIONS OF HUMAN AXILLARY SECRETIONS .……………………………………………………….21 1.2.1. Steroids ………………………………………………………………………………………………………………………………………….……..21 1.2.2. Volatile fatty acids ………………………………………………………………………………………………………………………….…....22 1.2.3. Sulfur compounds ……………………………………………………………………………………..…………………………………….…..24 1.3. AIM OF THE THESIS………………………………………………………………………………………….……………………….31 BIBLIOGRAPHY …………………………………………………………………………………………………………………….…………33 2. MAJOR SULFUR VOLATILES IN AXILLARY MALODOR ……………………………………………………………………..41 3-METHYL-3-SULFANYLHEXAN-1-OL AS MAJOR DESCRIPTOR FOR THE HUMAN AXILLA-SWEAT ODOR PROFILE (PUBLISHED IN CHEMISTRY AND BIODIVERSITY) ………………………………………………………………………………….….43 BIBLIOGRAPHY ...... …………………………………………………………………………………………………………………………63 3. IDENTIFICATION OF SULFUR ODOR PRECURSORS ............................................................................. 65 IDENTIFICATION OF THE PRECURSOR OF (S)-3-METHYL-3-SULFANYLHEXAN-1-OL, THE SULFURY MALODOR OF HUMAN AXILLA-SWEAT (PUBLISHED IN CHEMISTRY AND BIODIVERSITY) …….……………………………………………..…67 BIBLIOGRAPHY ...... …………………………………………………………………………………………………………………………85 Page | i UNIVERSITY OF GENEVA / FIRMENICH SA The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from precursors to odorous volatiles 4. GENDER AND BODY ODOR : IT IS ALL IN THE CHEMISTRY ............................................................... 87 GENDER-SPECIFIC DIFFERENCES BETWEEN THE CONCENTRATIONS OF NON-VOLATILE (R)/(S)-3-METHYL-3- SULFANYLHEXAN-1-OL AND (R)/(S)-3-HYDROXY-3-METHYL-HEXANOIC ACID ODOR PRECURSORS IN AXILLARY SECRETIONS (PUBLISHED IN CHEMICAL SENSES) …………………………………………………………………………………….89 BIBLIOGRAPHY……… .... …………………………………………………………………………………………………………………105 5. ENZYMES INVOLVED IN SULFUR COMPOUNDS BIOSYNTHESIS .................................................. 107 PROPERTIES OF RECOMBINANT STAPHYLOCOCCUS HAEMOLYTICUS CYSTATHIONINE -LYASE (METC) AND ITS POTENTIAL ROLE IN THE GENERATION OF VOLATILE THIOLS IN AXILLARY MALODOR (PUBLISHED IN CHEMISTRY AND BIODIVERSITY) ...........................……………………………………………………………………………………………………109 BIBLIOGRAPHY……… .... …………………………………………………………………………………………………………………129 6. FINAL CONCLUSIONS .............................................................................................................................. 131 BIBLIOGRAPHY……… .... …………………………………………………………………………………………………………………139 7. APPENDIX .................................................................................................................................................. 141 7.1. DETERMINATION OF ODOR DETECTION THRESHOLDS OF MAJOR SWEAT VOLATILES ........................ ………..143 7.2. BIOTRANSFORMATION OF CYSTEINYL-GLYCINE S-CONJUGATE BY S. HAEMOLYTICUS .................................. 148 7.3. FREE AND TOTAL AMINO-ACIDS COMPOSITION OF MALE AND FEMALE UNDERARM SECRETIONS ................... 151 7.4. CARBON-SULFUR -LYASE (C-S -LYASE) SIMILARITIES IN AXILLARY BACTERIA ........................................ 153 7.5 INHIBITION OF SWEAT MALODOR (INT. PAT. WO 2006/079934 A2) ……….………………………………………154 BIBLIOGRAPHY …….…………………………………………………………………………………………………………………...….171 Author publications………………………….……………………………………………………………………………………173 Author patents………………………….……………………………………………………………….……………………………173 Acknowledgements-Remerciements…….……………………………………………………………………………175 Page | ii UNIVERSITY OF GENEVA / FIRMENICH SA The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from precursors to odorous volatiles List of Abbreviations : sweat rate 3M2HA: 3-Methyl-2-Hexenoic Acid Apo D: Apolipoprotein D ASOB1: Apocrine Odor-Binding protein 1 ASOB2: Apocrine Odor-Binding protein 2 ATCC: American Type Culture Collection C. jeikeium: Corynebacterium jeikeium Cauxin: Carboxylesterase-like urinary excreted protein CBL: Cystathionine -Lyase CFU: Colony Forming Unit CGL: Cystathionine -Lyase CGS: Cystathionine -Synthase C-S lyase: Carbon-Sulfur lyase Cys-S-conjugate: Cysteine-S-conjugate; [1-(2-hydroxyethyl)-1-methylbutyl]-(L)-cysteine Cys/Met metabolism enzyme: Enzyme involved in cysteine and methionine metabolism Cys-Gly-S-conjugate: Cysteine-Glycine-S-conjugate; [1-(2-hydroxyethyl)-1-methylbutyl]-(L)- cysteinylglycine DHT: Dihydrotestosterone DSMZ: Deutsche Sammlung von Mikroorganism und Zellkulturen DTNB: 5,5‘-Dithiobis(2-Nitrobenzoic Acid) E. coli: Escherichia coli E3M2HA: (E)-3-Methyl-2-Hexenoic Acid EDTA: EthyleneDiamineTetraAcetic acid FMO3: Flavin-containing MonoOxygenase FSH: Follicle Stimulating Hormone GC/MS: Gas Chromatography-Mass Spectrometry GC-AED: Gas Chromatography coupled to an Atomic Emission Detector HAM: Human Axillary Malodor HMHA: 3-Hydroxy-3-MethylHexanoic Acid HSD: 3-HydroxySteroid Dehydrogenase Page | iii UNIVERSITY OF GENEVA / FIRMENICH SA The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from precursors to odorous volatiles IPTG: Isopropyl-beta-thio-galactoside kDa: kiloDalton (1 Da = 1,67 × 10-24 g) LH: Luteinizing Hormone MD-GC: Chiral Multidimensional Gas Chromatography MeSH: Methanethiol MGL: Methionine -Lyase MHC: Major Histocompatibility Complex NCBI: National Center for Biotechnology Information Nr: Number of repetitions OAH/OAS sulphydrylase: O-Acetylserine/O-Acetylhomoserine Sulphydrylase ODT: Odor Detection Threshold PAGE: Polyacrylamide gel electrophoresis pCBL: Putative Cystathionine -Lyase PLP: Pyridoxal-5‘-Phosphate HMHA: 3-Hydroxy-3-Methyl-2-Hexanoic Acid MSH: 3-Methyl-3-SulfanylHexan-1-ol SD: Standard Deviation SDS: Sodium Dodecyl Sulphate SEM: Standard Error of the Mean; SEM = SD/√Nr-1 S. epidermidis: Staphylococcus epidermidis S. haemolyticus: Staphylococcus haemolyticus Tc: hypothalamic core temperature Ts: average skin temperature UV-HPLC: High-performance liquid chromatography-UV absorption spectrometry VFA: Volatile Fatty Acids VNO: VomeroNasal Organ VSC: Volatile Sulfur Compound : set temperature of the blood : set temperature of the skin Page | iv UNIVERSITY OF GENEVA / FIRMENICH SA The biosynthetic pathway of sulfur-containing molecules in Human Axillary Malodor: from
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