Sexually mature male deer are known to rub-urinate, a process where urine is deposited on the tarsal gland. The resulting mixture of compounds from urine and secretions from the tarsal gland are used to signal sex, age, maturation status, and other information at close distance. We examined the difference in metabolites of tarsal gland extracts from male and female whitetail deer, Odocoileus virginianus, harvested during the mating season. Using NMR spectroscopy and high-pressure liquid chromatography linked to high resolution mass spectrometry (HPLC/HR-MS) we identified a homologous series of four male-specific compounds. The compounds are novel glycine conjugates of 10-hydroxy-6,9-oxido fatty acids, which we term cervidins A-D. Cervidins were deemed to possess the absolute configuration 6S,9R,10R through comparison of their spectroscopic data with those of known compounds. In addition, cholesterol 3-sulfate and 3-(3-hydroxyphenyl)-propanoic acid were found to be present in the extracts. Our results clearly demonstrate the diversity of potential semiochemicals contained in the mammalian integument.

已知性成熟的雄性鹿会小便，这是尿液沉积在睑板腺上的过程。来自尿液和睑板腺分泌物的化合物混合物可用于在近距离处发出性别，年龄，成熟状态和其他信息的信号。我们研究了在交配季节收获的雄性和雌性白尾鹿（Odocoileus virginianus）腺提取物代谢产物的差异。使用NMR光谱学和与高分辨率质谱法（HPLC / HR-MS）关联的高压液相色谱，我们鉴定了四个男性特异性化合物的同源序列。所述化合物是10-羟基-6,9-氧化脂肪酸的新型甘氨酸缀合物，我们称其为cervidins AD。cervidins被认为具有绝对构型6 S，9 - [R 10 - [R通过它们与那些已知化合物的光谱数据进行比较。此外，发现提取物中还存在胆固醇3-硫酸盐和3-（3-羟苯基）-丙酸。我们的结果清楚地证明了哺乳动物被皮中含有潜在的信息化学物质的多样性。