Characterization of an alkylresorcinol synthase that forms phenolics accumulating in the cuticular wax on various organs of rye (Secale cereale).,The Plant Journal

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Characterization of an alkylresorcinol synthase that forms phenolics accumulating in the cuticular wax on various organs of rye (Secale cereale).
The Plant Journal ( IF 6.2 ) Pub Date : 2020-01-25 , DOI: 10.1111/tpj.14704
Yulin Sun ₁ , Ruonan Yao ₁ , Xiufeng Ji ₂ , Hongqi Wu ₃ , Alvaro Luna ₁ , Zhonghua Wang ₃ , Reinhard Jetter _{1,

2}

Affiliation

Alkylresorcinols are bioactive compounds produced in diverse plant species, with chemical structures combining an aliphatic hydrocarbon chain and an aromatic ring with characteristic hydroxyl substituents. Here, we aimed to isolate and characterize the enzyme that forms the alkylresorcinols accumulating in the cuticular wax on the surface of all above‐ground organs of rye. Based on sequence homology with other type‐III polyketide synthases, a candidate alkylresorcinol synthase was cloned. Yeast heterologous expression showed that the enzyme, ScARS, is highly specific for the formation of the aromatic resorcinol ring structure, through aldol condensation analogous to stilbene synthases. The enzyme accepts long‐chain and very‐long‐chain acyl‐CoA starter substrates, preferring saturated over unsaturated chains. It typically carries out three rounds of condensation with malonyl‐CoA prior to cyclization, with only very minor activity for a fourth round of malonyl‐CoA condensation and cyclization to 5‐(2′‐oxo)‐alkylresorcinols or 5‐(2′‐hydroxy)‐alkylresorcinols. Like other enzymes involved in cuticle formation, ScARS is localized to the endoplasmic reticulum. ScARS expression patterns were found correlated with alkylresorcinol accumulation during leaf development and across different rye organs. Overall, our results thus suggest that ScARS synthesizes the cuticular alkylresorcinols found on diverse rye organ surfaces.

中文翻译：

表征间苯二酚合成酶的特征，该酶形成酚类，该酚类积累在黑麦（Secale谷类食品）的各个表皮蜡中。

烷基间苯二酚是在各种植物物种中产生的生物活性化合物，其化学结构结合了具有特征性羟基取代基的脂族烃链和芳环。在这里，我们旨在分离和鉴定形成黑麦所有地上器官表面上的表皮蜡中积累的烷基间苯二酚的酶。基于与其他III型聚酮化合物合酶的序列同源性，克隆了候选烷基间苯二酚合酶。酵母异源表达表明，通过类似于二苯乙烯合成酶的醛醇缩合，该酶ScARS对形成芳族间苯二酚环结构具有高度特异性。该酶接受长链和超长链酰基辅酶A起始物底物，比饱和链优先于饱和链。它通常在环化之前与丙二酰-CoA进行三轮缩合，而对于第四轮丙二酰-CoA缩合和环化成5-（2'-氧代）-烷基间苯二酚或5-（2'-羟基）-烷基间苯二酚像其他参与角质层形成的酶一样，ScARS定位于内质网。发现ScARS表达模式与叶发育过程中以及跨不同黑麦器官的烷基间苯二酚积累有关。总体而言，我们的结果因此表明，ScARS可以合成在各种黑麦器官表面发现的表皮烷基间苯二酚。

更新日期：2020-01-25

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