Axillary Odor

Shelley, Walter B.

doi:10.1001/archderm.1953.01540100070012

Cited by 152 publications

(59 citation statements)

References 9 publications

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“…Volatile substances evaporating from these areas make a key contribution to human body odor. However, sweat secreted from apocrine glands in these skin areas is initially odorless, and since the work of Shelley et al (1), it is known that skin bacteria release the odoriferous principles from nonsmelling substrates present in these secretions. Indeed, the axilla is a skin region colonized by an unusually dense bacterial population, with a species composition dominated by the two genera Staphylococcus and Corynebacterium (2,3).…”

mentioning

confidence: 99%

The Sequential Action of a Dipeptidase and a β-Lyase Is Required for the Release of the Human Body Odorant 3-Methyl-3-sulfanylhexan-1-ol from a Secreted Cys-Gly-(S) Conjugate by Corynebacteria

Emter

Natsch

2008

Journal of Biological Chemistry

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Human axillary odor is formed by the action of Corynebacteria on odorless axilla secretions. Sulfanylalkanols, 3-methyl-3-sulfanylhexan-1-ol in particular, form one key class of the odoriferous compounds. A conjugate with the dipeptide Cys-Gly has been reported as the secreted precursor for 3-methyl-3-sulfanylhexan-1-ol. Here, we confirm the Cys-Gly-(S) conjugate as the major precursor of this odorant, with lower levels of the Cys-(S) conjugate being present in axilla secretions. The enzymatic release of 3-methyl-3-sulfanylhexan-1-ol from the Cys-Gly-(S) conjugate by the axilla isolate Corynebacterium Ax20 was thus investigated. Cellular extracts of Ax20 released 3-methyl-3-sulfanylhexan-1-ol from the Cys-Gly-(S) conjugate and from the Cys-(S) conjugate, whereas the previously isolated C-S lyase of this bacterial strain was only able to cleave the Cys-(S) conjugate. o-Phenanthroline blocked the release from the Cys-Gly-(S) conjugate but did not affect cleavage of the Cys-(S) conjugate, indicating that in a first step, a metal-dependent dipeptidase hydrolyzes the Cys-Gly bond. This enzyme was purified by four chromatographic steps and gel electrophoresis, and the partial amino acid sequence was determined. The corresponding gene was cloned and expressed in Escherichia coli. It codes for a novel dipeptidase with a high affinity toward the Cys-Gly-(S) conjugate of 3-methyl-3-sulfanylhexan-1-ol. Co-incubating either the synthetic Cys-Gly-(S) conjugate or fresh axilla secretions with both the C-S lyase and the novel dipeptidase did release 3-methyl-3-sulfanylhexan-1-ol, proving that the sequential action of these two enzymes from the skin bacterium Corynebacterium Ax20 does release the odorant from the key secreted precursor.The skin in human armpits contains a dense arrangement of sweat glands. Volatile substances evaporating from these areas make a key contribution to human body odor. However, sweat secreted from apocrine glands in these skin areas is initially odorless, and since the work of Shelley et al. (1), it is known that skin bacteria release the odoriferous principles from nonsmelling substrates present in these secretions. Indeed, the axilla is a skin region colonized by an unusually dense bacterial population, with a species composition dominated by the two genera Staphylococcus and Corynebacterium (2, 3). Most individuals carry a flora that is dominated by either one of these two genera, and there is a strong correlation between a high population of Corynebacteria and strong axillary odor formation (2, 4). Subjects whose axillary skin is mainly colonized by Staphylococci emit only low levels of odor. Based on this fundamental work, axilla secretions contain non-odoriferous precursors that are transformed into the volatile substances by bacterial enzymes mainly present in Corynebacteria and to a lesser extent in Staphylococci.Early studies on the chemistry of human axilla odors identified the odoriferous steroids 5␣-androst-16-en-3-one (5, 6) and 5␣-androst-16-en-3␣-ol (7) in human axilla secretions. Lat...

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confidence: 99%

The Sequential Action of a Dipeptidase and a β-Lyase Is Required for the Release of the Human Body Odorant 3-Methyl-3-sulfanylhexan-1-ol from a Secreted Cys-Gly-(S) Conjugate by Corynebacteria

Emter

Natsch

2008

Journal of Biological Chemistry

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“…Sweat, as it is secreted by axillary glands, is odorless, and since the pioneering work of Shelley et al [3], it is known that the action of skin bacteria is needed to generate the odoriferous principles from non-smelling molecules present in these secretions. Indeed, the axilla is a skin region supporting a dense bacterial population, which is dominated by the two genera Staphylococcus and Corynebacteria [4] [5].…”

mentioning

confidence: 99%

“…The preparation of 6 via H 2 S addition/NaBH 4 reduction proved to be very inefficient. It was finally synthesized from pentan-2-one (10) via HornerÀWadsworthÀEmmons reaction with triethyl phosphonoacetate, 1,4-addition of PhCH 2 SH, followed by LiAlH 4 reduction and reductive cleavage of the thioether with Na in NH 3 .…”

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confidence: 99%

Identification of Odoriferous Sulfanylalkanols in Human Axilla Secretions and Their Formation through Cleavage of Cysteine Precursors by a CS Lyase Isolated from Axilla bacteria

Natsch

Schmid²,

Flachsmann³

2004

Chemistry & Biodiversity

107

127

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Human axillary odor is known to be formed upon the action of Corynebacteria sp. on per se odorless axilla secretions. Besides the known odoriferous acids, we report the occurrence in human axilla secretions of four odoriferous sulfanylalkanols, namely 3-sulfanylhexan-1-ol (3), 2-methyl-3-sulfanylbutan-1-ol (4), 3-sulfanylpentan-1-ol (5), and 3-methyl-3-sulfanylhexan-1-ol (6). These compounds have a pungent sweat/kitchen odor, also reminiscent of onions with some fruity connotations, and perception thresholds in the pg/l range. It was postulated that the odorless precursors for these compounds are cysteine conjugates. Bacterial isolates obtained from the human axilla and belonging to the Corynebacteria were, indeed, found to have the enzymatic capacity to release various thiols from cysteine conjugates. The metC gene, which is known to code for a cystathione-beta-lyase, was cloned from the axilla isolate Corynebacterium striatum Ax20 and heterologously expressed in E. coli. The pure recombinant enzyme cleaves various cysteine conjugates and has a similar substrate specificity as the cell homogenates of the wild-type. The recombinant enzyme was finally incubated with odorless axilla secretions and shown to release odoriferous thiols.

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“…These sex-specific phenomena of androstenone and physiological and psychological effects of volatile steroids may be related and influence each other. Volatile steroids, on the other hand, are generated through the metabolism of microorganisms living on the skin (8), the same as other kinds of body odors (1)(2)(3)(4). We previously reported that C. xerosis exhibited high capabilities for generating androstenone and we thought that this bacterium may play a pivotal role in skin-resident microorganisms in generating androstenone (11).…”

Section: Discussionmentioning

confidence: 97%

Suppressive Effect of Constituents Isolated from Kernel of Prunus armeniaca on 5 .ALPHA.-Androst-16-en-3-one Generated by Microbial Metabolism

et al. 2006

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It is well known that body odors are a complex mixture of many kinds of volatile compounds and body odor is also related to the metabolism of microorganisms living on the skin (1-4). Iida et al. (5) reported that the vinyl ketones 1-octen-3-one and cis-1,5-octadien-3-one, which were scented with a strong metallic odor, Abstract: It has recently been reported that 5a-androst-16-en-3-one (androstenone) is a key compound in body malodors, and that female subjects were more sensitive than male subjects to androstenone. Androstenone is generated by the metabolism of a skin-resident microorganism, Corynebacterium xerosis, and apricot kernel extract (AKE) effectively suppressed this metabolism. In this study, AKE was fractionated according to its suppressive activity on androstenone generation in C. xerosis, in order to confirm its active constituents. (R)-Prunasin and (S)-prunasin, which were nitrile compounds, were isolated and identified as the active constituents in AKE and they strongly suppressed the bacterial metabolism. Amygdaline was also isolated as an (R)-and (S)-mixture. This compound is a typical bioactive ingredient in apricot kernel and the structure has one more glucose molecule with b-1,6 bond in contrast to prunasin. However, amygdalin was not included in the active fraction and it did not have any effect on suppressing androstenone generation. Furthermore, neither prunasin nor amygdalin had any bactericidal effect. In addition, the generation of hydrogen cyanide was not detected from either of them during incubation with C. xerosis in the reaction to generate androstenone. Based on these results, we confirmed that prunasin was the active constituent in AKE suppressing the generation of androstenone. The mechanism did not depend on the inhibition of metalloprotein through the generation of hydrogen cyanide from prunasin. This suppressive effect is possibly based on the tertiary structure of prunasin and the structure may influence the metabolic components that are related to the generation of volatile steroids in skin-resident microorganisms. 353 JOS

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Axillary Odor

Cited by 152 publications

References 9 publications

The Sequential Action of a Dipeptidase and a β-Lyase Is Required for the Release of the Human Body Odorant 3-Methyl-3-sulfanylhexan-1-ol from a Secreted Cys-Gly-(S) Conjugate by Corynebacteria

The Sequential Action of a Dipeptidase and a β-Lyase Is Required for the Release of the Human Body Odorant 3-Methyl-3-sulfanylhexan-1-ol from a Secreted Cys-Gly-(S) Conjugate by Corynebacteria

Identification of Odoriferous Sulfanylalkanols in Human Axilla Secretions and Their Formation through Cleavage of Cysteine Precursors by a CS Lyase Isolated from Axilla bacteria

Suppressive Effect of Constituents Isolated from Kernel of Prunus armeniaca on 5 .ALPHA.-Androst-16-en-3-one Generated by Microbial Metabolism

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