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Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase
Liang, J; Liu, J; Brown, R; Jia, MR; Zhou, K; Peters, RJ; Wang, Q; Zhou K(周柯)
2018
Source PublicationPLANT JOURNAL
ISSN0960-7412
EISSN1365-313X
Volume94Issue:5Pages:847-856
SubtypeArticle
AbstractThe 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.
Keywordbiosynthesis maize root sesquiterpenoid terpene synthase
DOI10.1111/tpj.13901
WOS Keyword5-EPI-ARISTOLOCHENE SYNTHASE ; INDIRECT DEFENSE ; BIOSYNTHESIS ; PHYTOALEXINS ; HEDYCARYOL ; METABOLISM ; INTERMEDIATE ; ACCUMULATION ; MONOTERPENE ; CULTIVARS
Indexed BySCI ; EI
Language英语
WOS Research AreaPlant Sciences
WOS SubjectPlant Sciences
WOS IDWOS:000434179400010
EI Accession Number20182305291545
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ihep.ac.cn/handle/311005/285980
Collection多学科研究中心
Affiliation中国科学院高能物理研究所
First Author AffilicationInstitute of High Energy
Recommended Citation
GB/T 7714
Liang, J,Liu, J,Brown, R,et al. Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase[J]. PLANT JOURNAL,2018,94(5):847-856.
APA Liang, J.,Liu, J.,Brown, R.,Jia, MR.,Zhou, K.,...&周柯.(2018).Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase.PLANT JOURNAL,94(5),847-856.
MLA Liang, J,et al."Direct production of dihydroxylated sesquiterpenoids by a maize terpene synthase".PLANT JOURNAL 94.5(2018):847-856.
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