Hemiterpenoids and Pyrazines in the Odoriferous Urine of the Maned Wolf (Chrysocyon brachyurus)

Goodwin, Thomas E.; Songsasen, Nucharin; Broederdorf, Laura J.; Burkert, B. A.; Chen, C. Joi; Jackson, Stephen R.; Keplinger, K.B.; Rountree, M.E.; Waldrip, Z.J.; Wedell, M.E.; Desrochers, Linda P.; Baker, William K.; Helsper, J.P.F.G.

doi:10.1007/978-1-4614-5927-9_13

Cited by 4 publications

(16 citation statements)

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“…Despite the fact that the urine of several canids contains the reduced sulfur compound, 3-methyl-1-methylthiobut-3-ene, this compound was not found in the urine of the maned wolf. Instead, an isomer, methyl prenyl sulfide is one of the most abundant urinary volatile organic compound (VOC) in this species [47], further supporting evidence that urinary VOCs are unique to each species. In fact several hemiterpenoid compounds such as geranyl nitrile and methyl prenyl sulfide, thought to be synthesized via the mevalonate pathway, are prevalent in maned wolf urine [47].…”

Section: Introductionmentioning

confidence: 52%

“…This study is the first robust differential analysis of urinary VOCs for a solitary canid species that relies on chemical communication for reproductive success. Previous analyses of maned wolf urine show that sulfur-containing hemiterpenoids, hemiterpenoid alcohols, and nitrogen-containing pyrazines are main components contributing to this species' odiferous urine [47]. Despite the fact that the urine of several canids contains the reduced sulfur compound, 3-methyl-1-methylthiobut-3-ene, this compound was not found in the urine of the maned wolf.…”

Section: Introductionmentioning

confidence: 87%

“…maned wolf [8,38,39,[41][42][43][44][45][46]. Maned wolf urine has a very distinctive, pungent odor with scent marks remaining detectable to humans for several weeks [3,47]. Rates of scent marking do not differ between male and female maned wolves [9].…”

Section: Introductionmentioning

confidence: 99%

“…Within Canidae, urinary VOCs have been characterized for the red fox [48][49][50], coyote [51,52], domestic dog [53][54][55], gray wolf [56,57], African wild dog [39,40], and maned wolf [47,58], though differential analysis ascribing putative semiochemical status to certain compounds has only been studied in the gray wolf, a social species. This study is the first robust differential analysis of urinary VOCs for a solitary canid species that relies on chemical communication for reproductive success.…”

Section: Introductionmentioning

confidence: 99%

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Differential expression of urinary volatile organic compounds by sex, male reproductive status, and pairing status in the maned wolf (Chrysocyon brachyurus)

et al. 2021

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The maned wolf (Chrysocyon brachyurus) is an induced ovulator. Though the mechanism of ovulation induction remains unknown, it is suspected to be urinary chemical signals excreted by males. This study assessed volatile organic compounds (VOCs) in weekly urine samples across 5 months from 13 maned wolves (6 intact males, 1 neutered male, 6 females) with the goal of identifying VOCs that are differentially expressed across sex, reproductive status, and pairing status. Solid-phase microextraction (SPME) and gas chromatography-mass spectrometry (GC-MS) were used to extract and separate VOCs that were identified via spectral matching with authentic standards, with spectral libraries, or with new software that further matches molecular fragment structures with mass spectral peaks. Two VOCs were present across all 317 urine samples: 2,5-dimethyl pyrazine and 2-methyl-6-(1-propenyl)-pyrazine. Fifteen VOCs differed significantly (Adj. P < 0.001 and |log2 fold change| >2.0) between intact males and females. Using partial least squares-discriminant analysis, the compounds with the highest importance to the sex classification were delta-decalactone, delta-dodecalactone, and bis(prenyl) sulfide. Sixty-two VOCs differed between intact males and the neutered male. Important classifier compounds were 3-ethyl 2,5-dimethyl pyrazine, 2-methyl-6-(1-propenyl)-pyrazine, and tetrahydro-2-isopentyl-5-propyl furan. Several VOCs established as important here have been implicated in reproductive communication in other mammals. This study is the most robust examination of differential expression in the maned wolf thus far and provides the most comprehensive analysis of maned wolf urinary VOCs to date, increasing the sample size substantially over previous chemical communication studies in this species. New data analysis software allowed for the identification of compounds in the hormone-producing mevalonate pathway which were previously unreported in maned wolf urine. Several putative semiochemicals were identified as good candidates for behavioral bioassays to determine their role in maned wolf reproduction, and specifically in ovulation induction.

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Section: Introductionmentioning

confidence: 52%

Section: Introductionmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Differential expression of urinary volatile organic compounds by sex, male reproductive status, and pairing status in the maned wolf (Chrysocyon brachyurus)

et al. 2021

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“…5-Methylhexan-3-one has been identified in the preorbital gland secretion of klipspringer, Oreotragus oreotragus (Burger et al, 1997) and the blue duiker, Cephalophus monicola (Burger and Pretorius, 1987;Burger et al, 1997). Trimethylpyrazine was detected in the scent marks of female marmoset monkeys, Callithrix jacchus (Smith et al, 2001) and in the urine of bobcats, Lynx rufus (Mattina et al, 1991) as well as maned wolves, Chrysocyon brachyurus (Mattina et al, 1991;Smith et al, 2001;Goodwin et al, 2013). 2,4-Dimethylquinazoline was reported from dorsal patches of males of the Curaçaoan long-nosed bat, Leptonycteris curasoae (Muñoz-Romo et al, 2012).…”

Section: Species Differencesmentioning

confidence: 99%

Volatile Urinary Signals of Two Nocturnal Primates, Microcebus murinus and M. lehilahytsara

et al. 2020

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Mouse lemurs are small, nocturnal, arboreal solitary foragers and are endemic primates of Madagascar. This lifestyle and their high predation risk can explain why mouse lemurs rely heavily on olfaction for intraspecific communication. As they often use urine for this purpose, we investigated dichloromethane extracts of the urine of two mouse lemur species, the gray mouse lemur (Microcebus murinus) and the Godman's mouse lemur (M. lehilahytsara), using gas-chromatography-mass spectrometry. We detected 977 different volatile compounds of different compound classes in 22 urine extracts obtained from nine M. murinus (four males, five females) and nine M. lehilahytsara (three males, six females) individuals. We compared the volatile profiles of the sexes and species using principal component analyses and discriminant function analyses and detected a significant difference in the urinary profiles of males and females and in the profiles of M. murinus and M. lehilahytsara. These very complex sex-and species-specific signatures could be used for distance communication in the context of species recognition, for mate search and in male-male competition. Our study provides important mechanistic insights into complex chemical signaling pathways in primates that are mirrored, in the case of mouse lemurs, by their extraordinarily rich repertoire of olfactory receptors. The production of highly informative olfactory signals may be complementing the complex acoustic signaling system of these solitary foragers suggesting the existence of a multimodal communication network that should be highly beneficial for any species living in dispersed social networks.

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Reproductive endocrine patterns and volatile urinary compounds of Arctictis binturong: discovering why bearcats smell like popcorn

Greene

Wallen

Moresco

et al. 2016

Sci Nat

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Members of the order Carnivora rely on urinary scent signaling, particularly for communicating about reproductive parameters. Here, we describe reproductive endocrine patterns in relation to urinary olfactory cues in a vulnerable and relatively unknown viverrid--the binturong (Arctictis binturong). Female binturongs are larger than and dominate males, and both sexes engage in glandular and urinary scent marking. Using a large (n = 33), captive population, we collected serum samples to measure circulating sex steroids via enzyme immunoassay and urine samples to assay volatile chemicals via gas chromatography-mass spectrometry. Male binturongs had expectedly greater androgen concentrations than did females but, more unusually, had equal estrogen concentrations, which may be linked to male deference. Males also expressed a significantly richer array of volatile chemical compounds than did females. A subset of these volatile chemicals resisted decay at ambient temperatures, potentially indicating their importance as long-lasting semiochemicals. Among these compounds was 2-acetyl-1-pyrroline (2-AP), which is typically produced at high temperatures by the Maillard reaction and is likely to be responsible for the binturong's characteristic popcorn aroma. 2-AP, the only compound expressed by all of the subjects, was found in greater abundance in males than females and was significantly and positively related to circulating androstenedione concentrations in both sexes. This unusual compound may have a more significant role in mammalian semiochemistry than previously appreciated. Based on these novel data, we suggest that hormonal action and potentially complex chemical reactions mediate communication of the binturong's signature scent and convey information about sex and reproductive state.

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Hemiterpenoids and Pyrazines in the Odoriferous Urine of the Maned Wolf (Chrysocyon brachyurus)

Cited by 4 publications

References 53 publications

Differential expression of urinary volatile organic compounds by sex, male reproductive status, and pairing status in the maned wolf (Chrysocyon brachyurus)

Differential expression of urinary volatile organic compounds by sex, male reproductive status, and pairing status in the maned wolf (Chrysocyon brachyurus)

Volatile Urinary Signals of Two Nocturnal Primates, Microcebus murinus and M. lehilahytsara

Reproductive endocrine patterns and volatile urinary compounds of Arctictis binturong: discovering why bearcats smell like popcorn

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