Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase

doi:10.1111/tpj.13901

	Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase
	Wang, Q; Liu, J; Liang, J; Brown, R; Jia, MR; Zhou, K; Peters, RJ; Zhou K(周柯)
刊名	PLANT JOURNAL
	2018
卷号	94 期号:5 页码:847-856
关键词	biosynthesis maize root sesquiterpenoid terpene synthase
ISSN号	0960-7412
DOI	10.1111/tpj.13901
文献子类	Article
英文摘要	The astounding structural and biological diversities of the large class of terpenoid natural products are imparted by both their complex hydrocarbon backbones and further elaboration by the addition of multiple hydroxyl groups, which provide both solubility and specific binding properties. While the role of terpene synthases (TPSs) in generating hydrocarbons with complex backbones is well known, these also are known to generate (singly) hydroxylated products by the addition of water prior to terminating deprotonation. Here a maize sesquiterpene synthase was unexpectedly found to generate dually hydroxylated products directly from (E,E)-farnesyl diphosphate, primarily eudesmane-2,11-diol, along with two closely related structural isomers. The unprecedented formation of these diols was proposed to proceed via initial addition of water to a germacradienyl(+) intermediate, followed by protonation of the internal carbon-6,7-double-bond in the resulting hedycarol, with subsequent cyclization and further addition of water to an eudesmolyl(+) intermediate. Evidence for the proposed mechanism was provided by labeling studies, as well as site-directed mutagenesis, based on structural modeling, which identified an active site phenylalanine required for the protonation and further elaboration of hedycaryol. This dihydroxylated sesquiterpenoid synthase was specifically expressed in maize roots and induced by pathogen infection, with its major enzymatic product only detected in root exudates or infected roots, suggesting a role in defense. Regardless of the ultimate metabolic fate or physiological role of these diols, this report not only reveals an unanticipated extension of the catalytic prowess of TPSs, but also provides insight into the underlying enzymatic mechanism.
电子版国际标准刊号	1365-313X
WOS关键词	5-EPI-ARISTOLOCHENE SYNTHASE ; INDIRECT DEFENSE ; BIOSYNTHESIS ; PHYTOALEXINS ; HEDYCARYOL ; METABOLISM ; INTERMEDIATE ; ACCUMULATION ; MONOTERPENE ; CULTIVARS
WOS研究方向	Plant Sciences
语种	英语
WOS记录号	WOS:000434179400010
内容类型	期刊论文
源URL	[http://ir.ihep.ac.cn/handle/311005/285980]
专题	高能物理研究所_多学科研究中心
作者单位	中国科学院高能物理研究所
推荐引用方式 GB/T 7714	Wang, Q,Liu, J,Liang, J,et al. Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase[J]. PLANT JOURNAL,2018,94(5):847-856.
APA	Wang, Q.,Liu, J.,Liang, J.,Brown, R.,Jia, MR.,...&周柯.(2018).Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase.PLANT JOURNAL,94(5),847-856.
MLA	Wang, Q,et al."Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase".PLANT JOURNAL 94.5(2018):847-856.