Chemical characterization of territorial marking fluid of male Bengal tiger, Panthera tigris
Chemical characterization of territorial marking fluid of male Bengal tiger, Panthera tigris
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DOI：
10.1007/s10886-008-9462-y
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发表时间：
2008-05-01
影响因子：
2.3
通讯作者：
Weibchen, G.
中科院分区：
文献类型：
--
作者：
Burger, B. V.;Viviers, M. Z.;Weibchen, G.
雄性孟加拉虎（Panthera tigris）的领地标记液由尿液和少量脂质物质的混合物组成，脂质物质可以作为液体挥发性成分的控释载体。利用气相色谱和气相色谱-质谱联用技术，在打标液中鉴定出了 98 种挥发性化合物和元素硫。初步鉴定出另外 16 种挥发物。这些化合物大部分是链烷醇、链烷醛、2-链烷酮、支链和直链链烷酸、二羧酸二甲酯、γ-和δ-内酯以及含氮或硫的化合物。标记液的几个样品含有纯的(R)-3-甲基-2-辛酮、(R)-3-甲基-2-壬酮和(R)-3-甲基-2-癸酮，但这些酮在其他样品中部分或完全外消旋。 γ-内酯 (S)-(+)-(Z)-6-十二碳烯-4-内酯和 C-8 至 C-16 饱和 (R)-γ-内酯和 (S)-δ-内酯以高对映体纯度存在。手性羧酸、2-甲基壬酸、2-甲基癸酸、2-甲基十一烷酸和2-乙基己酸是外消旋体。此前报道的虎尿成分中未检测到尸胺、腐胺和 2-乙酰吡咯啉。一些酮、脂肪酸和内酯对标记液顶部空间的组成的主要贡献表明这些化合物可能是信息素的重要成分。尽管只占一小部分，但液体中的脂质部分比水性部分（尿液）含有更多的挥发性有机化合物。脂质作为老虎留下的化学信息的受控释放载体，其作用源于其对标记液挥发物的亲和力。在标记液的尿液部分中鉴定出了质量范围为 16 至 69 kDa 的六种蛋白质，其中包括被称为 cauxin 的类似羧酸酯酶的尿蛋白，之前在家猫和其他猫科动物的尿液中发现了这种蛋白。
The territorial marking fluid of the male Bengal tiger, Panthera tigris, consists of a mixture of urine and a small quantity of lipid material that may act as a controlled-release carrier for the volatile constituents of the fluid. Using gas chromatography and gas chromatography-mass spectrometry, 98 volatile compounds and elemental sulfur were identified in the marking fluid. Another 16 volatiles were tentatively identified. The majority of these compounds were alkanols, alkanals, 2-alkanones, branched and unbranched alkanoic acids, dimethyl esters of dicarboxylic acids, gamma- and delta-lactones, and compounds containing nitrogen or sulfur. Several samples of the marking fluid contained pure (R)-3-methyl-2-octanone, (R)-3-methyl-2-nonanone, and (R)-3-methyl-2-decanone, but these ketones were partly or completely racemized in other samples. The gamma-lactone (S)-(+)-(Z)-6-dodecen-4-olide and the C-8 to C-16 saturated (R)-gamma-lactones and (S)-delta-lactones were present in high enantiomeric purities. The chiral carboxylic acids, 2-methylnonanoic acid, 2-methyldecanoic acid, 2-methylundecanoic acid, and 2-ethylhexanoic acid were racemates. Cadaverine, putrescine, and 2-acetylpyrroline, previously reported as constituents of tiger urine, were not detected. The dominant contribution of some ketones, fatty acids, and lactones to the composition of the headspace of the marking fluid suggests that these compounds may be important constituents of the pheromone. Although it constitutes only a small proportion, the lipid fraction of the fluid contained larger quantities of the volatile organic compounds than the aqueous fraction (urine). The lipid derives its role as controlled-release carrier of the chemical message left by the tiger, from its affinity for the volatiles of the marking fluid. Six proteins with masses ranging from 16 to 69 kDa, inter alia, the carboxylesterase-like urinary protein known as cauxin, previously identified in the urine of the domestic cat and other felid species, were identified in the urine fraction of the marking fluid.