l-Kynurenine, an amino acid identified as a sex pheromone in the urine of ovulated female masu salmon

l-Kynurenine, an amino acid identified as a sex pheromone in the urine of ovulated female masu salmon
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L-犬尿氨酸,一种在排卵的雌性马苏鲑鱼尿液中被鉴定为性信息素的氨基酸

DOI:
10.1073/pnas.0604340103
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发表时间:
2006
期刊:
Proceedings of the National Academy of Sciences
影响因子:
--
通讯作者:
F. Yamazaki
F. Yamazaki
中科院分区:
--
文献类型:
--
作者:
H. Yambe;S. Kitamura;M. Kamio;Miho Yamada;S. Matsunaga;N. Fusetani;F. Yamazaki

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许多动物在繁殖季节利用性信息素寻找交配伴侣。然而,大多数脊椎动物的性信息素仍有待确定。在过去的20年里,类固醇和异黄酮类化合物已被确定为几种鱼类的性信息素。这些信息素被广泛地称为“激素信息素”,因为它们或它们的前体在这些鱼中充当激素。迄今为止,没有其他类型的性信息素已明确确定硬骨鱼。在这里,我们报告的“非激素信息素”硬骨鱼的鉴定。生殖成熟的雌性马苏鲑鱼(Oncorhynchus masou)的尿液含有吸引雄性的信息素。生物测定引导的分级分离产生了在光谱和色谱性质上与l-犬尿氨酸相同的活性化合物。犬尿氨酸是L-色氨酸在脊椎动物中的主要代谢产物。这种信息素甚至在皮摩尔浓度下也能激发雄性特有的行为;其电生理阈值为10−14 M。l-犬尿氨酸是雌性马苏鲑鱼宣传其准备交配的合理物质。
Many animals employ sex pheromones to find mating partners during their reproductive seasons. However, most sex pheromones of vertebrates remain to be identified. Over the past 20 years, steroids and prostaglandins have been identified as sex pheromones in several fishes. These pheromones are broadly termed “hormonal pheromones” because they or their precursors act as hormones in these fishes. Hitherto, no other type of sex pheromone has been unambiguously identified in teleost fish. Here we report the identification of a “nonhormonal pheromone” in teleost fish. The urine of the reproductively mature female masu salmon (Oncorhynchus masou) contains a male-attracting pheromone. Bioassay-guided fractionation yielded an active compound that was identical to l-kynurenine in spectral and chromatographic properties. l-Kynurenine is a major metabolite of l-tryptophan in vertebrates. This pheromone elicits a male-specific behavior at even picomolar concentrations; its electrophysiological threshold is 10−14 M. l-Kynurenine is a reasonable substance for female masu salmon to advertise their readiness for mating.