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玫瑰天竺葵(香叶天竺葵)中12-氧代植物二烯酸还原酶的特性研究

Characterization of 12-Oxophytodienoic Acid Reductases from Rose-scented Geranium (Pelargonium graveolens).

作者信息

Iijima Miu, Kenmoku Hiromichi, Takahashi Hironobu, Lee Jung-Bum, Toyota Masao, Asakawa Yoshinori, Kurosaki Fumiya, Taura Futoshi

出版信息

Nat Prod Commun. 2016 Dec;11(12):1775-1782.

Abstract

Pelargonium graveolens L'Hér, also referred to as rose geranium, is a popular herbal plant with typical rosy fragrance largely based on the blend of monoterpenoid constituents. Among them, citronellol, which is biosynthesized from geraniol via double bond reduction, is the most abundant scent compound. In this study, three 12-oxophytodienoic acid reductases (PgOPRl-3) hive been cloned from P. graveolens, as -possible candidates for the double-bond reductase involved in citronellol biosynthesis. The bacterially expressed recombinant PgOPRs did not reduce geraniol to citronellol, but stereoselectively converted citral into (S)-citronellal in the presence of NADPH. Thus, the a,-unsaturated carbonyl moiety in the substrate is essential for the catalytic activity of PgOPRs; as reported for OPRs from other plants and structurally related yeast old yellow enzymes. PgOPRs promiscuously accepted linear and cyclic α,β- uisaturated carbonyl substrates, including methacrolein, a typical reactive carbonyl compound. The possible biotechnological applications for PgOPRs in plant metabolic'engineering, based on their catalytic properties, are discussed herein.

摘要

香叶天竺葵(Pelargonium graveolens L'Hér),也被称为玫瑰天竺葵,是一种广受欢迎的草本植物,具有典型的玫瑰香味,这种香味很大程度上基于单萜类成分的混合。其中,通过香叶醇经双键还原生物合成的香茅醇是含量最高的香味化合物。在本研究中,从香叶天竺葵中克隆出了三种12-氧代植物二烯酸还原酶(PgOPR1-3),作为参与香茅醇生物合成的双键还原酶的可能候选者。细菌表达的重组PgOPR不会将香叶醇还原为香茅醇,但在存在NADPH的情况下会立体选择性地将柠檬醛转化为(S)-香茅醛。因此,底物中的α,β-不饱和羰基部分对于PgOPR的催化活性至关重要;正如其他植物的OPR和结构相关的酵母老黄色酶所报道的那样。PgOPR随意接受线性和环状α,β-不饱和羰基底物,包括典型的活性羰基化合物甲基丙烯醛。本文基于其催化特性讨论了PgOPR在植物代谢工程中的可能生物技术应用。

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