The biosynthesis of shikimate metabolites

Dewick, Paul M.

doi:10.1039/np9951200101

Cited by 17 publications

(11 citation statements)

References 56 publications

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“…This observation correlates with declining levels for metabolites associated with the shikimic acid pathway (quinic acid, tyrosine, and shikimic acid) by 7 and 10 DAF under HNT ( Figure 7 and Figure S4 ). Previous literature has shown that the shikimic acid pathway contribute to biotic and abiotic stress response through the synthesis of protective compounds such as anthocyanins and tocopherols (Dewick, 1995). It also produces the precursors for a phytohormone, salicylic acid, which is involved in the transduction of response to several abiotic stresses such as high and low temperatures as well as heavy metal stress (Janda et al, 2007).…”

Section: Discussionmentioning

confidence: 99%

Metabolic Dynamics of Developing Rice Seeds Under High Night-Time Temperature Stress

et al. 2019

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High temperature stress during rice reproductive development results in yield losses. Reduced grain yield and grain quality has been associated with high temperature stress, and specifically with high night-time temperatures (HNT). Characterizing the impact of HNT on the phenotypic and metabolic status of developing rice seeds can provide insights into the mechanisms involved in yield and quality decline. Here, we examined the impact of warmer nights on the morphology and metabolome during early seed development in six diverse rice accessions. Seed size was sensitive to HNT in four of the six genotypes, while seed fertility and seed weight were unaffected. We observed genotypic differences for negative impact of HNT on grain quality. This was evident from the chalky grain appearance due to impaired packaging of starch granules. Metabolite profiles during early seed development (3 and 4 days after fertilization; DAF) were distinct from the early grain filling stages (7 and 10 DAF) under optimal conditions. We observed that accumulation of sugars (sucrose, fructose, and glucose) peaked at 7 DAF suggesting a major flux of carbon into glycolysis, tricarboxylic acid cycle, and starch biosynthesis during grain filling. Next, we determined hyper (HNT > control) and hypo (HNT < control) abundant metabolites and found 19 of the 57 metabolites to differ significantly between HNT and control treatments. The most prominent changes were exhibited by differential abundance of sugar and sugar alcohols under HNT, which could be linked to a protective mechanism against the HNT damage. Overall, our results indicate that combining metabolic profiles of developing grains with yield and quality parameters under high night temperature stress could provide insight for exploration of natural variation for HNT tolerance in the rice germplasm.

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Section: Discussionmentioning

confidence: 99%

Metabolic Dynamics of Developing Rice Seeds Under High Night-Time Temperature Stress

et al. 2019

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“…Since the three reductive steps all involve reduction of an , -conjugated double bond with the same stereochemical characteristics (shown in previous experiments to be anti, see ref. 2), it is possible that the single enzyme is responsible for catalyzing all three steps in the pathway. The potent immunosuppressants ascomycin (FK520) 270, FK506 269 and rapamycin 272 are macrocyclic polyketides that all contain a unit probably derived from 3,4-dihydroxycyclohexanecarboxylic acid.…”

Section: Cyclohexanecarboxylic Acidmentioning

confidence: 99%

“…This report reviews the literature that was published during 1995 and 1996 on the biosynthesis of compounds, mainly non-nitrogenous, that are derived wholly or partly from shikimate, and continues the coverage described in Volume 12 of Natural Product Reports 1 and earlier reports. 2,3 This review includes descriptions of the biosynthetic pathways, the enzymes and enzyme mechanisms involved, and brief information about the genes encoding for these enzymes.…”

Section: Introductionmentioning

confidence: 99%

The biosynthesis of shikimate metabolites

Dewick¹

1998

Nat. Prod. Rep.

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“…Hydroxycinnamyl alcohols, such as p‐coumaryl, caffeyl, coniferyl and sinapyl alcohols (Figure ), also known as monolignols, form a group of secondary plant metabolites derived from phenylalanine and having a wide variety of functions both as structural and as signaling molecules . These natural phenolic alcohols act as monomers in lignin biosynthesis, the process of radical bio‐polymerization that generates the most abundant accumulation of natural aromatic compounds .…”

Section: Introductionmentioning

confidence: 99%

A Facile Preparation of Hydroxycinnamyl Alcohols withSimultaneous Protection of Phenol Groups as Carbonate

2018

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A novel procedure for reduction and simultaneous protection of phenol groups of hydroxycinnamic acids to the related alcohols has been developed. During the formation of mixed anhydrides from the acids and an alkyl chloroformate, the phenol was protected as carbonate, and the mixed anhydrides were reduced with an aqueous solution of sodium borohydride. Free phenols were obtained by deprotection under mild conditions with 30% aq. NH4OH in methanol. O‐protected phenolic alcohols can be converted by standard methods into orthogonal protected derivatives. This rapid and efficient synthetic method offers a simple and high‐yield preparation of these important fine chemicals, overcoming the tedious and costly procedures associate with the use of strong reducing agents such as LiAlH4 and DIBAL−H.

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The biosynthesis of shikimate metabolites

Cited by 17 publications

References 56 publications

Metabolic Dynamics of Developing Rice Seeds Under High Night-Time Temperature Stress

Metabolic Dynamics of Developing Rice Seeds Under High Night-Time Temperature Stress

The biosynthesis of shikimate metabolites

A Facile Preparation of Hydroxycinnamyl Alcohols withSimultaneous Protection of Phenol Groups as Carbonate

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