androst-16-en-3-one and androst-16-en-3-ol

To explore the possibility that compounds which were identified as pheromones in experimental animals mediate human menstrual synchrony, we examined the relationship between menstrual synchrony and the ability to smell putative pheromones, 5alpha-androst-16-en-3alpha-ol (3alpha-androstenol) and 5alpha-androst-16-en-3-one (5alpha-androstenone). When we examined menstrual synchrony among 64 women living together in a college dormitory, we found that 24 (38%) of them became synchronized with room-mates in 3 months. Afterwards, dilution series of 3alpha-androstenol and 5alpha-androstenone and the control odorant (pyridine) were presented to the 64 women and sensitivity to the odors was compared between synchronized and non-synchronized women. No difference was found between the two groups of women in the detection threshold for pyridine, indicating that general olfactory ability did not differ between them. The detection threshold for 3alpha-androstenol of synchronized women was significantly lower than that of non-synchronized women, but no difference in the threshold for 5alpha-androstenone was found between synchronized and non-synchronized women. These results indicate that the women who showed menstrual synchrony had a higher sensitivity to 3alpha-androstenol but not necessarily to 5alpha-androstenone.

Topics: Androstenes; Androstenols; Female; Humans; Menstruation; Pheromones; Sensory Thresholds; Smell

The pheromone binding protein 'pheromaxein' which binds the pheromonal 16-androstene steroids in the saliva of the male pig (boar), was degraded and lost its binding activity in saliva incubated in air for 72 h at 21 degrees C and 37 degrees C. However, pheromaxein and its binding activity were retained in saliva incubated for 168 h at 4 degrees C. When the 3H-labelled pheromones 5 alpha-androst-16-en-3 alpha-ol (3 alpha-androstenol), 5 alpha-androst-16-en-3-one (5 alpha-androstenone) and 5 alpha-androst-16-en-3 beta-ol (3 beta-androstenol) were incubated with boar saliva for 168 h at 21 degrees C, 3 alpha-androstenol was primarily converted to 5 alpha-androstenone and 5 alpha-androstenone to 3 beta-androstenol; 3 beta-androstenol was unchanged. Evidence was obtained for microorganisms being responsible for these steroid transformations.

Topics: Androstenes; Androstenols; Animals; Bacteria; Carrier Proteins; Intercellular Signaling Peptides and Proteins; Male; Pheromones; Saliva; Swine; Temperature; Time Factors

Three mature Large White boars were anaesthetized and received [7(n)-3H]pregnenolone by continuous infusion into right and left spermatic arteries for up to 180 min. Spermatic venous blood flow was measured by separate timed collections of completely diverted outflow from each testis and blood not sampled was returned to the peripheral circulation. The total radioactivity in plasma from each testis increased markedly during the first 60 min of infusion to reach a plateau from 80 to 180 min. Radiolabelling of 5 alpha-androst-16-en-3-one, 5 alpha-androst-16-en-3 beta-ol and -3 alpha-ol showed similar patterns with ratios of mean radioactivity of 5:3:1 respectively between 80 and 180 min. In comparison, the amounts of tritiated 4,16-androstadien-3-one formed were very small. The radiolabelling of testosterone and 4-androstenedione occurred more rapidly than that of the 16-androstenes and reached maxima by 30 min. However the amounts were only one-fifth (testosterone) and one-tenth (4-androstenedione) those of the combined quantities of tritiated 16-androstenes. Addition of human chorionic gonadotrophin (hCG) to the infusate to one testis in each animal (so that 5000 i.u. hCG were delivered in 15-20 min) produced no change in the outputs of radiolabelled steroids although radioimmunoassay of spermatic venous plasma in samples from the third experiment showed a transient increase in the concentration of 4-androstene-3,17-dione during the hCG infusion. It is suggested the lack of response to hCG could be produced by saturation and down regulation of binding sites by the very high local concentrations of hCG.

Topics: Androstadienes; Androstenedione; Androstenes; Androstenols; Animals; Chorionic Gonadotropin; Male; Pregnenolone; Swine; Testis; Testosterone; Time Factors

Submaxillary glands of mature Göttingen miniature pigs were examined for the presence of a sexual dimorphism. Gland weights, serous cell hypertrophy and total protein in the glands were much greater in male than female pigs. High concentrations of the pheromonal 16-androstene steroids were present in the glands of males and exceeded 2 mmol/g in some animals; this was primarily due to 5 alpha-androst-16-en-3 alpha-ol. The high concentration of 16-androstene steroids in boar glands was correlated with the presence of large amounts of binding protein for these steroids in the glands; smaller amounts of the binding protein were detected in female glands. These findings are similar to those found in domestic pigs, but the degree of sexual dimorphism assessed from these findings is more extreme in the miniature pig.

Topics: Androgen-Binding Protein; Androstenes; Androstenols; Animals; Carrier Proteins; Electrophoresis, Polyacrylamide Gel; Female; Male; Pheromones; Sex Attractants; Sex Characteristics; Submandibular Gland; Swine; Swine, Miniature

Topics: Androstenes; Androstenols; Animals; Pheromones