Felinine: a urinary amino acid of Felidae

Hendriks, W.H.; Moughan, Paul J.; Tarttelin, Michael F.; Woolhouse, Anthony D.

doi:10.1016/0305-0491(95)00130-1

Cited by 60 publications

(47 citation statements)

References 19 publications

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“…It has been found that free felinine is totally degraded during acid hydrolysis under the conditions used in our laboratory (18). However, Westall (3) found that during acid hydrolysis felinine degraded to cysteine and cystine, while Tallan et al (5) reported that felinine degraded to cystine and cysteic acid, thus indicating a possible degradation pathway of felinine via Cys.…”

Section: Characterization Of [ 35 S]cysteine Peptide Fractions (Expermentioning

confidence: 72%

Isolation and Characterization of a Felinine-containing Peptide from the Blood of the Domestic Cat (Felis catus)

Rutherfurd

Moughan

et al. 2002

Journal of Biological Chemistry

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Felinine is a unique sulfur-containing amino acid found in the urine of domestic cats and select members of the Felidae family. Research over the past 50 years has led to the conclusion that felinine must be synthesized in the kidney, as free felinine is not present in the blood or tissues of cats. We propose that felinine is present in the blood as ␥-glutamylfelinylglycine, a glutathione conjugate. To test our hypothesis [ 35 S]cysteine was administered intraperitoneally to one entire male cat, and two radiolabeled fractions were isolated from the blood. We showed that the amounts of both fractions in serum were linked to the gender of the cat, with entire males expressing significantly higher levels compared with castrated males, entire females, or spayed females. Both fractions were characterized using amino acid analysis with one fraction (S18), containing an equimolar ratio of Cys, Glu, and Gly, while fraction S16 was found to contain Cys, plus free amino acids. Nanospray mass spectrometry confirmed the sequence of fraction S18 as being ␥-glutamylfelinylglycine and conclusively proving that felinine is present in the blood of cats as part of a larger molecule, thereby questioning the current theory that felinine is synthesized in the kidney.

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Section: Characterization Of [ 35 S]cysteine Peptide Fractions (Expermentioning

confidence: 72%

Isolation and Characterization of a Felinine-containing Peptide from the Blood of the Domestic Cat (Felis catus)

Rutherfurd

Moughan

et al. 2002

Journal of Biological Chemistry

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“…Felinine is structurally similar to methionine and cysteine but does not appear to undergo the oxidation of the sulphur atom that these other sulphur containing amino acids are susceptible to . It is possible that felinine stability may be pH-dependent as synthetic felinine is either degraded or modified in the present of acids (Westall, 1953;Hendriks et al, 1995b). Recently, Rutherfurd et al (2004) reported that felinine, naturally present in male cat urine degrades or disappears from solution much faster compared to synthetic felinine dissolved in water.…”

Section: Introductionmentioning

confidence: 99%

“…While the function of felinine is uncertain, it may be involved in the production of pheromone compounds used for the scent marking of territories in order to repel male cats and potentially attract female cats (Hendriks et al, 1995b). Felinine itself has been reported to be odourless (Brand, 1979;Hendriks et al, 1995a) but when stored at room temperature and at 4 C, synthetic felinine develops the characteristic catty odour associated with feline urine (Hendriks et al, 1995b). Consequently, it is likely that breakdown or modification of felinine is required to elicit this characteristic and pungent odour.…”

Section: Introductionmentioning

confidence: 99%

“…Consequently, it is likely that breakdown or modification of felinine is required to elicit this characteristic and pungent odour. A number of felinine degradation products have been postulated with 3-mercapto-3-methyl-1-butanol being the prime candidate responsible for the catty odour (Joulain and Laurent, 1989;Mattina et al, 1991;Hendriks et al, 1995b). Other workers, however, have not been unable to detect the presence of 3-mercapto-3-methyl-1-butanol in entire male cat urine samples indicating that other volatiles originating from felinine or felinine degradation products may be involved in the generation of the characteristic catty odour of feline urine urine or that the potency of 3-mercapto-3-methyl-1-butanol is such that the levels present in cat urine were below the level of detection.…”

Section: Introductionmentioning

confidence: 99%

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Felinine stability in the presence of selected urine compounds

et al. 2006

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Summary. The stability of felinine, an amino acid present in feline urine, was investigated. Synthetic felinine was unstable in the urine of a selection of mammals. Felinine was found to stable in feline urine in which urea had been degraded. Synthetic felinine was found to react specifically with urea and did not react with urea analogues such as biuret or thiourea or other nucleophilic compounds such as ammonia which is more nucleophilic or acetamide and water which are less nucleophilic than urea. The reaction of urea and felinine was independent of pH over the range of 3-10. Urea did not react with N-acetyl-felinine suggesting a felinine N-terminal interaction with urea. Mass spectral analysis of the reaction products showed the presence of carbamylated felinine and fragmentation ions derived from carbamyl-felinine. The physiological relevance of felinine carbamylation is yet to be determined.

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“…3) Felinine is a putative precursor of pheromones used for conspecific recognition and reproductive status by mature cats. 4) Cauxin hydrolyzes the peptide bond of the felinine precursor 3-methylbutanol cysteinylglycine, producing felinine and glycine in cat urine.…”

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confidence: 99%