- 5α-Androst-16-en-3α-ol β-D-glucuronide, precursor of 5α-androst-16-en-3α-ol in human sweat
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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 H2O-soluble conjugate, and this precursor was formally characterized in this study for the first time in human sweat. The possible H2O-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 H2O-soluble precursor of α-androstenol in apocrine secretion should be a β-glucuronide. Copyright
- Starkenmann, Christian,Mayenzet, Fabienne,Brauchli, Robert,Troccaz, Myriam
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p. 2197 - 2208
(2014/01/06)
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- Transformation of a series of saturated isomeric steroidal diols by Aspergillus tamarii KITA reveals a precise stereochemical requirement for entrance into the lactonization pathway
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Four isomers of 5α-androstan-3,17-diol have been transformed by the filamentous fungus Aspergillus tamarii, an organism which has the ability to convert progesterone to testololactone in high yield through an endogenous four step enzymatic pathway. The only diol handled within the lactonization pathway was 5α-androstan-3α,17β-diol which, uniquely underwent oxidation of the 17β-alcohol to the 17-ketone prior to its Baeyer-Villiger oxidation and the subsequent production of 3α-hydroxy-17a-oxa-D-homo-5α-androstan-17-one. This demonstrated highly specific stereochemical requirements of the 17β-hydroxysteroid dehydrogenase for oxidation of this specific steroidal diol to occur. In contrast, the other three diols were transformed within the hydroxylation pathway resulting in functionalization at C-11β. Only 5α-androstan-3β,17α-diol could bind to the hydroxylase in multiple binding modes undergoing monohydroxylation in 6β and 7β positions. Evidence from this study has indicated that hydroxylation of saturated steroidal lactones may occur following binding of ring-D in its open form in which an α-alcohol is generated with close spatial parity to the C-17α hydroxyl position. All metabolites were isolated by column chromatography and were identified by 1H, 13C NMR and DEPT analysis and further characterized using infra-red, elemental analysis and accurate mass measurement.
- Hunter, A. Christy,Collins, Catherine,Dodd, Howard T.,Dedi, Cinzia,Koussoroplis, Salomé-Juliette
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p. 352 - 358
(2011/11/12)
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- Catalytic hydrogenation of halosteroidal derivatives by bipyridine or phenanthroline complexes of copper(II) in hydrazine aqueous media
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We report two synthetic systems, Cu(Bpy)2+ and Cu(Phen) 2+, for catalytic hydrogenation of steroidal haloalkenes in the presence of hydrazine and air. These studies demonstrated that the selective hydrogenation is faster for the 1,10-phenanthroline-Cu(II) system because forming more stable copper complex are formed, leaving fewer free copper ions in solution. Evidence also supports that the catalytic power of Cu(II) ions can be tuned moderately through the addition of bidentate ligand, Bpy or Phen. Copyright Taylor & Francis Group, LLC.
- Du, Huang-Chi,Liu, Kung-Cheng,Li, Wen-Shan
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p. 621 - 630
(2007/10/03)
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- PREPARATION OF UNLABELLED AND 3H>-LABELLED EPITESTOSTERONE AND ITS METABOLITES
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Cold as well as 3H>-labelled substrates and metabolites IX-XI, XV, XVI, XX-XXII, XXIV, XXV and XXVIII were prepared by catalytic hydrogenation of epitestosterone (VIII) and Λ1-dehydroepitestosterone (XIII).The key step in the preparation of compound XXVIII was reaction of 3β-tosylates XXVI and XXX with potassium nitrite in dimethyl sulfoxide.
- Kasal, Alexander,Fuksova, Kveta,Pouzar, Vladimir
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p. 600 - 611
(2007/10/02)
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- Fragrance compositions and other compositions which contain human pheromones
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The invention concerns novel, non-therapeutic fragrance compositions and other compositions containing an odorant and a naturally occurring human pheromone. The invention also concerns fragrance compositions containing mixtures of naturally occurring human pheromones. The human pheromones disclosed are steroids which desirably belong to two distinct chemical classes: 16-Androstenes and Estrenes.
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