3-Ethyl-2,7-dimethyl octane, a testosterone dependent unique urinary sex pheromone in male mouse (Mus musculus) (original) (raw)
Related papers
Journal of Biosciences, 2002
The present study was carried out to investigate the chemical nature of the urine of male mice and to assess its bioactivity. Urine of mature male mice was extracted with dichloromethane (1 : 1 ratio v/v) and analysed by gas-chromatography linked mass-spectrometry (GC-MS). Ten different compounds such as alkanes, alcohols, etc. were detected in the urine. Among the ten, five compounds are specific to males, namely 3-cyclohexene-1methanol (I), 3-amino-s-triazole (II), 4-ethyl phenol (III), 3-ethyl-2,7-dimethyl octane (IV) and 1-iodoundecane (V). The compound, 4-ethylphenol, has been previously reported in several strains of male mice. Furthermore, the compounds (II) and (IV) are similar to 2-sec-butylthiazole and dehydro-exo-brevicomin compounds which have already been reported in male mice. Bioassay revealed that compounds (II), (III) and (IV) were responsible for attracting females and in inducing aggression towards males, as compared to the other compounds, i.e. (I) and (V). The results indicate that these three volatiles (II, III and IV) of male mice appear to act as attractants of the opposite sex.
Sex- and Gonad-Affecting Scent Compounds and 3 Male Pheromones in the Rat
Chemical Senses, 2008
This study was aimed at identifying sex pheromones of the rat (Rattus norvegicus). We characterized the volatiles and semivolatiles of rat preputial gland and voided urine by using gas chromatography-mass spectrometry (GC-MS) and quantified them by their GC areas (abundances) and percentage of GC areas (relative abundances). Although all the compounds other than 4-heptanone and phenol detected were shared by males and females, the quantities for some of these sex-common compounds exhibited sexual dimorphism and decreased with gonadectomy. Thus, these compounds might be sex pheromones. Among them, squalene from preputial glands and 2-heptanone and 4-ethyl phenol from urine were 3 major compounds. They were richer in males and could be suppressed by castration. Adding any of the 3 compounds (at a concentration higher than its physiological level in male urine) to castrated male urine (CMU) increased the attractiveness of CMU to sex-naive females. Adding the 3 together (at the levels in normal male urine) to CMU significantly increased the attractiveness of CMU to females. However, such combination did not fully restore females' preference for urine from intact males, suggesting that some other trace compounds such as 4-heptanone and phenol might also play some roles in sex attractiveness. Thus, squalene, 2-heptanone, and 4-ethyl phenol were indeed male pheromone molecules in rats. Our study also indicates that E,E-b-farnesene and E-a-farnesene, both richer in females than males, might be putative female pheromones.
Animal Behaviour, 1985
The urine of intact, adult male mice elicits more investigatory sniffing from female mice than does the urine of castrated males. When either of two androgen-dependent urinary compounds, 2-sec-butyl dihydrothiazole or dehydro-exo-brevicomin are added to castrate urine, its relative attractiveness remains the same. When both compounds are added to castrate urine, however, its activity is enhanced and the castrate urine becomes as attractive to females as whole, intact male urine. Females exposed to the reconstituted 'normal' urine for 3 rain per day, displayed more frequent oestrus cycles. The two synthetic compounds are synergistic in the context of castrate urine, producing an olfactory message that behaviourally and physiologically mimics the activity of the normal biological signal.
Pattern of volatile compounds in dominant and subordinate male mouse urine
Journal of Chemical Ecology, 1989
The urinary volatiles from dominant and subordinate male mice were chromatographically compared, both immediately and seven days after dominant-subordinate relationships between pairs were formed. Statistical comparison of the peak areas of volatile constituents present in male urine revealed that 16 urinary compounds exhibited substantial concentration differences depending upon social status of the animals. Urinary dihydrofurans, ketones, and acetates exhibited a significant, long-term (seven-day) decrease in the urine of subordinates when compared to control and dominant males. Two sesquiterpenic compounds, c~-and/~-farnesene, were elevated only in the dominant urine one week after dominance was established. 2-(see-Butyl)-4,5-dihydrothiazole was found in higher concentration in bladder or excreted urine of dominant males when compared to subordinates. Of the 16 compounds subjected to statistical analysis, four exhibited hormonal dependency: c~-and ~-farnesene, dehydro-exo-brevicomin, and 2-(sec-butyl)-4,5-dihydrothiazole. Neither dehydro-exo-brevicomin nor 2-(see-butyl)-4,5-dihydrothiazole was present in the urine of immature and castrated males. Testosterone treatment restores their presence in male urine. Also, c~-and r were absent in the urine of immature males and significantly reduced in the urine of castrated males. The absence of c~-and/3-farnesene in bladder urine suggests that one of the sex-accessory glands may be the site of their origin.
Protein-bound Male Urinary Pheromones: Differential Responses According to Age and Gender
Chemical Senses, 1998
The attractive properties of male urinary pheromones were tested on adult or prepubertal male and female mice. An androgen-dependent protein is present in adult male urine (major urinary protein, MUP) which has been suggested to be a pheromone-binding protein. We tested the pheromonal properties of the protein-bound volatiles in a test of attractiveness. These molecules, that co-purify with MUP, attract females and repel adult males. In prepubertal animals, females are repelled and males are attracted by the same stimuli. These results are similar to those obtained by others with adult male whole urine. Therefore MUP binds molecules with a pheromonal activity, and these molecules are sufficient to act as male signals.
Regulation of volatile and non-volatile pheromone attractants depends upon male social status
Scientific Reports, 2019
We investigated the regulation of chemical signals of house mice living in seminatural social conditions. We found that male mice more than doubled the excretion of major urinary proteins (MUPs) after they acquired a territory and become socially dominant. MUPs bind and stabilize the release of volatile pheromone ligands, and some MUPs exhibit pheromonal properties themselves. We conducted olfactory assays and found that female mice were more attracted to the scent of dominant than subordinate males when they were in estrus. Yet, when male status was controlled, females were not attracted to urine with high MUP concentration, despite being comparable to levels of dominant males. To determine which compounds influence female attraction, we conducted additional analyses and found that dominant males differentially upregulated the excretion of particular MUPs, including the pheromone MUP20 (darcin), and a volatile pheromone that influences female reproductive physiology and behavior. Our findings show that once male house mice become territorial and socially dominant, they upregulate the amount and types of excreted MUPs, which increases the intensities of volatiles and the attractiveness of their urinary scent to sexually receptive females. House mice (Mus musculus) excrete large quantities of major urinary proteins (MUPs) that bind and transport hydrophobic ligands, including several volatile pheromones 1-3. Upon excretion, MUPs slow down the release of volatiles from scent marks 4-8 , which may prolong their attraction and influence on conspecifics. MUPs are often suggested to show high individual diversity and thereby mediate individual and kin recognition 9,10. They are encoded by 21 paralogous loci, but MUP genes are highly homologous 11,12 and no individual variation has been detected in wild populations 13. Interestingly, MUP excretion is sexually dimorphic 5,14,15 , under endocrine control 16-18 , and dynamically regulated 19 depending upon health 20-22 , nutritional status 23 , and social interactions 24,25. Our aims here were to test whether house mice regulate the excretion of MUPs or volatile pheromone ligands depending upon their social status, and whether such regulation influences the attractiveness of their odor to potential mates 24. Male house mice are territorial and much evidence indicates that intra-and inter-sexual selection are mediated by chemosensory signals. Dominant territorial males scent mark their territories, and males deposit more scent-marks after winning an agonistic encounter compared to losers (winners are commonly labeled as 'dominants' and losers as 'subordinates') 26-28. Females are attracted to male urinary scent 29-31 and especially to the scent of 'dominant' males 32-35. Male reproductive success correlates with scent-marking when male social status is controlled and females are free to select their mates 36. Male urine also has priming effects on female reproductive physiology (accelerating puberty, synchronizing estrus, and blocking pregnancy 37), and especially if males are socially 'dominant' 38. Several volatile odor compounds (VOCs) have been identified as sexual pheromones (eliciting sexual attraction, priming effects, or both), including αand βfarnesene 39 , 2-sec-Butyl-4, 5-dihydrothiazole (SBT), 3, 4-dehydro-exo-brevicomin (DHB), and 6-hydroxy-6-methyl-3-heptanone (HMH 40), though not in all strains 41. Exposure to a combination of male pheromones (SBT, DHB, and HMH) induces female olfactory
Arquivos de Ciências Veterinárias e Zoologia da UNIPAR
It is well established that the behavior of different mammalians, including rodents, may undergo profound changes in the presence of individuals of other species. Therefore, the aim of this study was to verify if the presence of pheromones from male mice could influence the reproductive parameters of female rats. Twenty Swiss (SW) male mice and 16 Long Evans (LE) female Rats were housed in separate rooms, with communication in the ceiling in its entire length. A continuous flow of air was planned to pass through the room of the mice before the room of the rats and finally be exchanged with the external environment. During 45 days, vaginal smears were collected. Relative weights of reproductive organs, estradiol, progesterone, and dehydroepiandrosterone levels were also measured. The total duration of the estrous cycle and relative organ weight remained unchanged. On the other hand, the proestrus and estrus phases, as well as the estradiol levels were increased, while the diestrus ph...
An ephemeral sex pheromone in the urine of female house mice (Mus domesticus)
Behavioral and neural biology, 1992
From previous research, the ultrasonic vocalizations of male mice (Mus domesticus) to female mouse urine were hypothesized to be learned as a result of classical conditioning during adult heterosexual encounters. According to this interpretation, a previously neutral conditioned stimulus in female urine comes to elicit vocalizations as a result of its association with some other unknown unconditioned stimulus associated with adult females. However, the research from which this hypothesis was derived utilized urine collected from females housed in metabolic cages. Three experiments further examined the classical conditioning hypothesis using two types of female urine: (i) metabolic-cage-collected urine and (ii) freshly voided urine. Experiment 1 demonstrated that, in contrast to vocalizations to metabolic-cage-collected urine, adult heterosexual experience was not necessary for males to vocalize to freshly voided female urine. In addition, unlike metabolic-cage-collected urine (Exper...
Theriogenology, 2006
The present study was designed to identify the urinary volatiles across various reproductive stages of female mice in order to detect estrus-specific chemical signal. The urine of adult female mice were extracted with dichloromethane (1:1 ratio, v/v) and analyzed by gas chromatography linked mass-spectrometry (GC-MS). Numerous compounds were identified during estrus cycle of female mice urine. Among these, the compounds, namely, isocroctylhydrazine, 4-methyl-2-heptanone and auzulene were specific to proestrus stage and the compounds, 1-H-cyclopop-e.auzulene, caryophyllene, copanene were specific to estrus stage. However, the compound, 1-iodo-2methyl undecane (1I2MU) was observed both in proestrus and estrus phases and was absent in all other phases. The volatile signal produced at the end of proestrus and the beginning of estrus phase appears to be behaviourally important in the attraction of males. Moreover, the behaviour assay revealed that the compound, 1I2MU, is involved in attracting the male mice. This result concludes that the 1-iodo-2methyl undecane is considered as a putative estrus-specific chemo-signal.