Female-to-male sex pheromones of low volatility in the Asian elephant, Elephas maximus

In their natural ecosystems, the sexes of Asian elephants, Elephas maximus, live separately. For several weeks prior to ovulation, the urine and cervical mucus of female Asian elephants contain extractable chemical agents of low volatility that elicit a high frequency of flehmen responses from bull elephants as an integral part of mating. Subsequent to flehmen responses, male sexual arousal occurs and, if the female is available, mating results. During the course of our project to determine the agent(s) and describe the responses associated with female to male sexual communication, we have identified an unusual compound. This compound, apparently the sole component of the active fraction, was identified by mass, proton nuclear magnetic resonance, ultraviolet/visible, and infrared spectrometries as indolo-[2,1-b]quinazoline-6,12-dione (tryptanthrine). Exhaustive and repetitive bioassays established that pure authentic (synthetic) tryptanthrine was not the compound responsible for the bioresponse. Rather a coeluting minor component, also of low volatility, elicited the male bioresponse