Metabolism of Furanocoumarins by Three Recombinant CYP9A Proteins From the Polyphagous Cotton Bollworm Helicoverpa armigera

IF 1.5 4区 农林科学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY
Kai Tian, Jiang Zhu, Xinghui Qiu
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Abstract

Furanocoumarins are a class of chemical compounds with phototoxic properties. For herbivores, efficient detoxification of such defense compounds is the prerequisite to feed successfully on furanocoumarin-containing plants. The cotton bollworm Helicoverpa armigera is a very important polyphagous pest in agriculture, but how it copes with toxic furanocoumarins in some of its host plants is not well understood. Given that cytochrome P450s are well known for their capacity in xenobiotic metabolism, this study attempted to explore the potential roles of cytochrome P450s in furanocoumarin transformation in this pest. Our data showed that two linear structures (psoralen and xanthotoxin) could be metabolized by three recombinant CYP9A enzymes, but no detectable depletion was observed for the linear one with the 8-dimethylallyloxy substituent on the coumarin moiety (imperatorin) and the angular furanocoumarin (angelicin). Initial epoxidation of the double bond connecting C2' and C3' of the furano ring following by cleavage of the epoxidated furan ring, leading to the formation of more soluble, less reactive and nonphotosensitizing metabolites, was identified as a common mechanism of linear furanocoumarin metabolism using a quadrupole/time-of-flight (Q-TOF) mass spectrometry interfaced with a high performance liquid chromatography (HPLC) system. Our data demonstrated that multiple P450s were involved in the detoxification of linear furanocoumarins in the cotton bollworm. These findings contribute to a better understanding of the biochemical basis of adaptation to plant defense chemicals in this economically important pest.

Abstract Image

多食性棉铃虫 Helicoverpa armigera 的三种重组 CYP9A 蛋白对呋喃香豆素的代谢作用
呋喃香豆素是一类具有光毒性的化合物。对于食草动物来说,高效解毒这类防御化合物是成功捕食含呋喃香豆素植物的先决条件。棉铃虫(Helicoverpa armigera)是农业中一种非常重要的多食性害虫,但人们对它如何应对某些寄主植物中的有毒呋喃香豆素并不十分了解。鉴于细胞色素 P450s 在异生物代谢方面的能力众所周知,本研究试图探索细胞色素 P450s 在该害虫体内呋喃香豆素转化过程中的潜在作用。我们的数据显示,三种重组 CYP9A 酶可以代谢两种线性结构(补骨脂素和黄腐霉毒素),但对于香豆素分子上带有 8-二甲基烯丙氧基取代基的线性结构(欧鼠李素)和角呋喃香豆素(当归苷),没有观察到可检测到的损耗。利用与高效液相色谱(HPLC)系统连接的四极杆/飞行时间(Q-TOF)质谱法,我们发现连接呋喃环 C2' 和 C3' 的双键发生初始环氧化反应,然后环氧化呋喃环被裂解,从而形成溶解度更高、反应性更低且无光敏性的代谢物,这是线性呋喃香豆素代谢的常见机制。我们的数据表明,多种 P450 参与了棉铃虫体内线性呋喃香豆素的解毒过程。这些发现有助于更好地了解这种具有重要经济价值的害虫适应植物防御化学品的生化基础。
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来源期刊
CiteScore
4.30
自引率
4.50%
发文量
115
审稿时长
12 months
期刊介绍: Archives of Insect Biochemistry and Physiology is an international journal that publishes articles in English that are of interest to insect biochemists and physiologists. Generally these articles will be in, or related to, one of the following subject areas: Behavior, Bioinformatics, Carbohydrates, Cell Line Development, Cell Signalling, Development, Drug Discovery, Endocrinology, Enzymes, Lipids, Molecular Biology, Neurobiology, Nucleic Acids, Nutrition, Peptides, Pharmacology, Pollinators, Proteins, Toxicology. Archives will publish only original articles. Articles that are confirmatory in nature or deal with analytical methods previously described will not be accepted.
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