title: 5α-Androst-16-en-3α-ol β-D-glucuronide, precursor of 5α-androst-16-en-3α-ol in human sweat.
abstract: 5α-Androst-16-en-3α-ol (α-androstenol) is an important contributor to human axilla sweat odor. It is assumed that α-andostenol is excreted from the apocrine glands via a H2 O-soluble conjugate, and this precursor was formally characterized in this study for the first time in human sweat. The possible H2 O-soluble precursors, sulfate and glucuronide derivatives, were synthesized as analytical standards, i.e., α-androstenol, β-androstenol sulfates, 5α-androsta-5,16-dien-3β-ol (β-androstadienol) sulfate, α-androstenol β-glucuronide, α-androstenol α-glucuronide, β-androstadienol β-glucuronide, and α-androstenol β-glucuronide furanose. The occurrence of α-androstenol β-glucuronide was established by ultra performance liquid chromatography (UPLC)/MS (heated electrospray ionization (HESI)) in negative-ion mode in pooled human sweat, containing eccrine and apocrine secretions and collected from 25 female and 24 male underarms. Its concentration was of 79 ng/ml in female secretions and 241 ng/ml in male secretions. The release of α-androstenol was observed after incubation of the sterile human sweat or α-androstenol β-glucuronide with a commercial glucuronidase enzyme, the urine-isolated bacteria Streptococcus agalactiae, and the skin bacteria Staphylococcus warneri DSM 20316, Staphylococcus haemolyticus DSM 20263, and Propionibacterium acnes ATCC 6919, reported to have β-glucuronidase activities. We demonstrated that if α- and β-androstenols and androstadienol sulfates were present in human sweat, their concentrations would be too low to be considered as potential precursors of malodors; therefore, the H2 O-soluble precursor of α-androstenol in apocrine secretion should be a β-glucuronide.
authors: Firmenich SA, Corporate R&D Division, 1 Route des Jeunes, P.O. Box 239, CH-1211 Geneva-8, (phone: +41-22-7803477; fax: +41-22-7803334). christian.starkenmann@firmenich.com.
authors: Christian
authors: C
authors: Starkenmann
authors: Fabienne
authors: F
authors: Mayenzet
authors: Robert
authors: R
authors: Brauchli
authors: Myriam
authors: M
authors: Troccaz
mesh_terms: D000737:Androstenols / Q000032:analysis* / Q000737:chemistry* / Q000378:metabolism; D001050:Apocrine Glands / Q000737:chemistry / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D004439:Eccrine Glands / Q000737:chemistry / Q000378:metabolism; D005260:Female; D005966:Glucuronidase / Q000378:metabolism; D020719:Glucuronides / Q000032:analysis* / Q000378:metabolism; D006094:Gram-Positive Bacteria / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D008297:Male; D009812:Odorants / Q000032:analysis; D021241:Spectrometry, Mass, Electrospray Ionization; D013542:Sweat / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000737:Androstenols; D020719:Glucuronides; C000590557:androst-16-en-3-ol glucuronide; C000152:androsta-5,16-dien-3 beta-ol; D005966:Glucuronidase
keywords: Bacterial degradation; Human sweat; Malodor; α-Androstenol β-glucuronide