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Involvement of CYP347W1 in neurotoxin 3-nitropropionic acid-based chemical defense in mustard leaf beetle Phaedon cochleariae
Insect Science ( IF 2.9 ) Pub Date : 2021-07-08 , DOI: 10.1111/1744-7917.12944 Nanxia Fu 1, 2 , Tobias Becker 1 , Wolfgang Brandt 3 , Maritta Kunert 1, 4 , Antje Burse 1, 5 , Wilhelm Boland 1
Insect Science ( IF 2.9 ) Pub Date : 2021-07-08 , DOI: 10.1111/1744-7917.12944 Nanxia Fu 1, 2 , Tobias Becker 1 , Wolfgang Brandt 3 , Maritta Kunert 1, 4 , Antje Burse 1, 5 , Wilhelm Boland 1
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Chrysomelina beetlesstore 3-nitropropionic acid in form of a pretoxin, isoxazolin-5-one glucoside-conjugated ester, to protect themselves against predators. Here we identified a cytochrome P450 monooxygenase, CYP347W1, to be involved in the production of the 3-nitropropionic acid moiety of the isoxazolin-5-one glucoside ester. Knocking down CYP347W1 led to a significant depletion in the concentration of the isoxazolin-5-one glucoside ester and an increase in the concentration of the isoxazolin-5-one glucoside in the larval hemolymph. Enzyme assays with the heterologously expressed CYP347W1 showed free β-alanine was not the direct substrate. Homology modeling indicated that β-alanine-CoA ester can fit into CYP347W1’s active site. Furthermore, we proved that Phaedon cochleariae eggs are not able to de novo synthesize 3-NPA, although both isoxazolin-5-one glucoside and its 3-NPA-conjugated ester are present in the eggs. These results provide direct evidence for the involvement of CYP347W1 in the biosynthesis of a P. cochleariae chemical defense compound.
中文翻译：
CYP347W1 参与基于神经毒素 3-硝基丙酸的芥菜叶甲虫 Phaedon cochleariae 的化学防御
Chrysomelina 甲虫以前毒素异恶唑啉-5-酮糖苷共轭酯的形式储存 3-硝基丙酸，以保护自己免受捕食者的侵害。在这里，我们鉴定了一种细胞色素 P450 单加氧酶CYP347W1，它参与异恶唑啉-5-酮糖苷酯的 3-硝基丙酸部分的产生。敲除 CYP347W1导致幼虫血淋巴中异恶唑啉-5-酮糖苷酯的浓度显着降低，异恶唑啉-5-酮糖苷浓度增加。用异源表达的CYP347W1进行的酶测定显示游离β -丙氨酸不是直接底物。同源性模型表明β-丙氨酸-CoA酯可以适应CYP347W1的活性位点。此外，我们证明了Phaedon cochleariae卵不能从头合成 3-NPA，尽管卵中存在异恶唑啉-5-酮糖苷及其 3-NPA 共轭酯。这些结果为CYP347W1参与了P. cochleariae化学防御化合物的生物合成提供了直接证据。
更新日期：2021-07-08
中文翻译：
CYP347W1 参与基于神经毒素 3-硝基丙酸的芥菜叶甲虫 Phaedon cochleariae 的化学防御
Chrysomelina 甲虫以前毒素异恶唑啉-5-酮糖苷共轭酯的形式储存 3-硝基丙酸，以保护自己免受捕食者的侵害。在这里，我们鉴定了一种细胞色素 P450 单加氧酶CYP347W1，它参与异恶唑啉-5-酮糖苷酯的 3-硝基丙酸部分的产生。敲除 CYP347W1导致幼虫血淋巴中异恶唑啉-5-酮糖苷酯的浓度显着降低，异恶唑啉-5-酮糖苷浓度增加。用异源表达的CYP347W1进行的酶测定显示游离β -丙氨酸不是直接底物。同源性模型表明β-丙氨酸-CoA酯可以适应CYP347W1的活性位点。此外，我们证明了Phaedon cochleariae卵不能从头合成 3-NPA，尽管卵中存在异恶唑啉-5-酮糖苷及其 3-NPA 共轭酯。这些结果为CYP347W1参与了P. cochleariae化学防御化合物的生物合成提供了直接证据。
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