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雀形目鸟类中的箭毒蛙毒素生物碱:来自新几内亚的第二种有毒鸟类属(科瓦氏伊夫鹑)

Batrachotoxin alkaloids from passerine birds: a second toxic bird genus (Ifrita kowaldi) from New Guinea.

作者信息

Dumbacher J P, Spande T F, Daly J W

机构信息

Molecular Genetics Laboratory, National Zoological Park, Smithsonian Institution, 3001 Connecticut Avenue NW, Washington, DC 20008, USA.

出版信息

Proc Natl Acad Sci U S A. 2000 Nov 21;97(24):12970-5. doi: 10.1073/pnas.200346897.

DOI:10.1073/pnas.200346897
PMID:11035772
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC27162/
Abstract

Batrachotoxins, including many congeners not previously described, were detected, and relative amounts were measured by using HPLC-mass spectrometry, in five species of New Guinean birds of the genus Pitohui as well as a species of a second toxic bird genus, Ifrita kowaldi. The alkaloids, identified in feathers and skin, were batrachotoxinin-A cis-crotonate (1), an allylically rearranged 16-acetate (2), which can form from 1 by sigmatropic rearrangement under basic conditions, batrachotoxinin-A and an isomer (3 and 3a, respectively), batrachotoxin (4), batrachotoxinin-A 3'-hydroxypentanoate (5), homobatrachotoxin (6), and mono- and dihydroxylated derivatives of homobatrachotoxin. The highest levels of batrachotoxins were generally present in the contour feathers of belly, breast, or legs in Pitohui dichrous, Pitohui kirhocephalus, and Ifrita kowaldi. Lesser amounts are found in head, back, tail, and wing feathers. Batrachotoxin (4) and homobatrachotoxin (6) were found only in feathers and not in skin. The levels of batrachotoxins varied widely for different populations of Pitohui and Ifrita, a result compatible with the hypothesis that these birds are sequestering toxins from a dietary source.

摘要

在新几内亚的五种辉亭鸟属鸟类以及第二种有毒鸟类科瓦氏伊芙翠鸟中,检测到了包括许多此前未描述过的同类物在内的箭毒蛙毒素,并使用高效液相色谱-质谱联用仪测量了其相对含量。在羽毛和皮肤中鉴定出的生物碱有:箭毒蛙毒素A顺式巴豆酸酯(1)、一种经烯丙基重排的16-乙酸酯(2),它可在碱性条件下通过[3,3] - 迁移重排由1形成、箭毒蛙毒素A和一种异构体(分别为3和3a)、箭毒蛙毒素(4)、箭毒蛙毒素A 3'-羟基戊酸酯(5)、高箭毒蛙毒素(6)以及高箭毒蛙毒素的单羟基和二羟基衍生物。在黑头辉亭鸟、黑头林鵙鹟和科瓦氏伊芙翠鸟中,箭毒蛙毒素的最高含量通常存在于腹部、胸部或腿部的正羽中。在头部、背部、尾部和翅膀的羽毛中含量较少。箭毒蛙毒素(4)和高箭毒蛙毒素(6)仅在羽毛中发现,而在皮肤中未发现。不同种群的辉亭鸟和伊芙翠鸟体内箭毒蛙毒素的含量差异很大,这一结果与这些鸟类从饮食来源中摄取毒素的假设相符。

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本文引用的文献

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Homobatrachotoxin in the genus Pitohui: chemical defense in birds?黑头林鵙鹟属中的箭毒蛙毒素:鸟类的化学防御?
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