Biosynthesis of iridoid sex pheromones in aphids.
Biosynthesis of iridoid sex pheromones in aphids.
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DOI：
10.1073/pnas.2211254119
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发表时间：
2022-10-18
影响因子：
11.1
通讯作者：
中科院分区：
文献类型：
--
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植物、动物和微生物产生大量的天然产物，对防御和通信至关重要。这些化合物中的大多数显示出遗传学上的限制，但是，在极少数情况下，相同的天然产物是由两个不同界的生物合成的。例如，单萜衍生的环烯醚萜类化合物已在50多个植物科中发现，但也在几个昆虫目中观察到。蚜虫环烯醚萜途径是迄今为止报道的最长和化学上最复杂的昆虫衍生天然产物生物合成途径之一，其发现突出了昆虫和植物中代谢酶趋同进化的潜在机制，包括招募不同的酶类来催化相同的化学过程。环烯醚萜类化合物广泛存在于植物和昆虫中，具有多种生态功能。虽然环烯醚萜类化合物的生物合成在植物中得到了广泛的研究，但对昆虫如何合成这些天然产物知之甚少。在这里，我们阐明了环烯醚萜类化合物顺-反-荆芥内酯和顺-反-荆芥内酯的豌豆蚜Acyrthosiphon pisum（Harris），在那里他们作为性信息素的生物合成。在有性生殖的雌性蚜虫的后腿中独家生产环烯醚萜，这使我们能够通过寻找在该组织中特异表达的基因来鉴定环烯醚萜基因。候选酶的生化特性表明，环烯醚萜途径在蚜虫的收益通过相同的序列的中间体所描述的植物。这六种已鉴定的蚜虫酶与植物中的对应酶无关，最终证明了植物和昆虫中整个环烯醚萜途径的独立进化。与植物途径相反，至少有三种蚜虫环烯醚萜酶可能是膜结合的。我们证明，脂质环境有利于环烯醚萜类环戊醇-吡喃支架在体外的反应性烯醇中间体的环化，这表明膜是蚜虫环烯醚萜途径的重要组成部分。总之，这一复杂的昆虫代谢途径的发现为蚜虫环烯醚萜类性信息素的形成奠定了遗传和生化基础，这一发现也为理解界间复杂代谢途径的趋同进化奠定了基础。
Plants, animals, and microbes produce a plethora of natural products that are important for defense and communication. Most of these compounds show a phylogenetically restricted occurrence, but, in rare instances, the same natural product is biosynthesized by organisms in two different kingdoms. The monoterpene-derived iridoids, for example, have been found in more than 50 plant families but are also observed in several insect orders. The discovery of the aphid iridoid pathway, one of the longest and most chemically complex insect-derived natural product biosynthetic pathways reported to date, highlights the mechanisms underlying the convergent evolution of metabolic enzymes in insects and plants, including the recruitment of different enzyme classes to catalyze the same chemical processes. Iridoid monoterpenes, widely distributed in plants and insects, have many ecological functions. While the biosynthesis of iridoids has been extensively studied in plants, little is known about how insects synthesize these natural products. Here, we elucidated the biosynthesis of the iridoids cis-trans-nepetalactol and cis-trans-nepetalactone in the pea aphid Acyrthosiphon pisum (Harris), where they act as sex pheromones. The exclusive production of iridoids in hind legs of sexual female aphids allowed us to identify iridoid genes by searching for genes specifically expressed in this tissue. Biochemical characterization of candidate enzymes revealed that the iridoid pathway in aphids proceeds through the same sequence of intermediates as described for plants. The six identified aphid enzymes are unrelated to their counterparts in plants, conclusively demonstrating an independent evolution of the entire iridoid pathway in plants and insects. In contrast to the plant pathway, at least three of the aphid iridoid enzymes are likely membrane bound. We demonstrated that a lipid environment facilitates the cyclization of a reactive enol intermediate to the iridoid cyclopentanoid-pyran scaffold in vitro, suggesting that membranes are an essential component of the aphid iridoid pathway. Altogether, our discovery of this complex insect metabolic pathway establishes the genetic and biochemical basis for the formation of iridoid sex pheromones in aphids, and this discovery also serves as a foundation for understanding the convergent evolution of complex metabolic pathways between kingdoms.
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DOI：
10.1073/pnas.1523468113
发表时间：
2016-03-15
影响因子：
11.1
作者：
Beran, Franziska;Rahfeld, Peter;Koellner, Tobias G.
通讯作者：
Koellner, Tobias G.
影响因子：
56.9
作者：
Frey, M;Chomet, P;Gierl, A
通讯作者：
Gierl, A
影响因子：
16.6
作者：
Jensen, Niels Bjerg;Zagrobelny, Mika;Hjerno, Karin;Olsen, Carl Erik;Houghton-Larsen, Jens;Borch, Jonas;Moller, Birger Lindberg;Bak, Soren
通讯作者：
Bak, Soren
影响因子：
11.6
作者：
Jozwiak, Adam;Gutkowska, Malgorzata;Swiezewska, Ewa
通讯作者：
Swiezewska, Ewa
影响因子：
10.7
作者：
Kumar, Sudhir;Stecher, Glen;Tamura, Koichiro
通讯作者：
Tamura, Koichiro