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Literature summary extracted from

  • Milkowski, C.; Strack, D.
    Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering (2010), Planta, 232, 19-35.
    View publication on PubMed

Application

EC Number Application Comment Organism
2.3.1.91 agriculture targeted metabolic engineering, designed to generate low-sinapate ester lines of Brassica napus, because sinaoate esters hamper to use of Brassica napus as animal feeding crop Brassica napus

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.91 DNA and amino acid sequence determination and analysis, phylogenetic analysis Arabidopsis thaliana
2.3.1.91 homology-based cloning strategy, DNA and amino acid sequence determination and analysis, phylogenetic analysis Brassica napus
3.1.1.49 functional expression of Brassica napus BnSCE3 in Arabidopsis thaliana developing seeds resulting in a dramatic decrease in the sinapine content Brassica napus
3.1.1.49 gene At1g28640, the BnSCE3 homologue is tagged on chromosome I Arabidopsis thaliana
3.1.1.49 gene At1g28650, the BnSCE3 homologue is tagged on chromosome I Arabidopsis thaliana
3.1.1.49 gene At1g28660, the BnSCE3 homologue is tagged on chromosome I Arabidopsis thaliana
3.1.1.49 gene At1g28670, the BnSCE3 homologue is tagged on chromosome I Arabidopsis thaliana

Protein Variants

EC Number Protein Variants Comment Organism
2.3.1.91 additional information metabolic engineering by dsRNAi technique allowing effient gene silencing in a polyploid genetic background, silencing SCT. Suppression of SCT in Arabidopsis thaliana results in a reduction of seed sinapine content by 52% compared to the wild-type. Construction of a T-DNA insertion mutant lacking SCT activity Arabidopsis thaliana
2.3.1.91 additional information metabolic engineering by dsRNAi technique allowing effient gene silencing in a polyploid genetic background, silencing SCT. Suppression of SCT in Brassica napus results in a reduction of seed sinapine compared to the wild-type Brassica napus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.91 1-O-sinapoyl-beta-D-glucose + choline Brassica napus
-
 D-glucose + sinapoylcholine
-
 ?
2.3.1.91 1-O-sinapoyl-beta-D-glucose + choline Arabidopsis thaliana
-
 D-glucose + sinapoylcholine
-
 ?
3.1.1.49 additional information Brassica napus BnSCE3 reveals a broad substrate specificity toward phenolic choline esters, even accepting phosphatidylcholine, pointing to a phospholipase A-like activity ?
-
 ?
3.1.1.49 O-sinapoylcholine + H2O Brassica napus i.e. sinapine choline + sinapate
-
 ?
3.1.1.49 O-sinapoylcholine + H2O Arabidopsis thaliana i.e. sinapine choline + sinapate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.91 Arabidopsis thaliana Q8VZU3
-
-
2.3.1.91 Brassica napus
-
-
-
3.1.1.49 Arabidopsis thaliana P0C8Z7 gene At1g28640
-
3.1.1.49 Arabidopsis thaliana Q38894 gene At1g28670
-
3.1.1.49 Arabidopsis thaliana Q3E7I6 gene At1g28650
-
3.1.1.49 Arabidopsis thaliana Q9FPE4 At1g28660
-
3.1.1.49 Brassica napus
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
2.3.1.91 1-O-sinapoyl-beta-D-glucose + choline = D-glucose + sinapoylcholine catalytic mechanism, a double displacement ping-pong mechanism would require water exclusion from the active center to prevent hydrolysis. Since this assumption is not supported by the SCT structure model Brassica napus
a
2.3.1.91 1-O-sinapoyl-beta-D-glucose + choline = D-glucose + sinapoylcholine Ser-His-Asp catalytic triad, catalytic mechanism, a double displacement ping-pong mechanism would require water exclusion from the active center to prevent hydrolysis, overview. Since this assumption is not supported by the SCT structure model Arabidopsis thaliana
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.3.1.91 seed
-
 Brassica napus
-
2.3.1.91 seed
-
 Arabidopsis thaliana
-
3.1.1.49 seed germinating Brassica napus
-
3.1.1.49 seed germinating Arabidopsis thaliana
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.91 1-O-sinapoyl-beta-D-glucose + choline
-
 Brassica napus D-glucose + sinapoylcholine
-
 ?
2.3.1.91 1-O-sinapoyl-beta-D-glucose + choline
-
 Arabidopsis thaliana D-glucose + sinapoylcholine
-
 ?
3.1.1.49 additional information BnSCE3 reveals a broad substrate specificity toward phenolic choline esters, even accepting phosphatidylcholine, pointing to a phospholipase A-like activity Brassica napus ?
-
 ?
3.1.1.49 O-sinapoylcholine + H2O i.e. sinapine Brassica napus choline + sinapate
-
 ?
3.1.1.49 O-sinapoylcholine + H2O i.e. sinapine Arabidopsis thaliana choline + sinapate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.91 SCT
-
 Brassica napus
2.3.1.91 SCT
-
 Arabidopsis thaliana
2.3.1.91 sinapoylglucose: choline sinapoyltransferase
-
 Brassica napus
2.3.1.91 sinapoylglucose:choline sinapoyltransferase
-
 Arabidopsis thaliana
3.1.1.49 SCE
-
 Brassica napus
3.1.1.49 SCE
-
 Arabidopsis thaliana
3.1.1.49 sinapine esterase
-
 Brassica napus
3.1.1.49 sinapoylcholine(sinapine) esterase
-
 Brassica napus
3.1.1.49 sinapoylcholine(sinapine) esterase
-
 Arabidopsis thaliana

General Information

EC Number General Information Comment Organism
2.3.1.91 evolution evolutionary ancestry of the sinapoyltransferases sinapoylglucose:L-malate sinapoyltransferase and sinapoylglucose:choline sinapoyltransferase with serine carboxypeptidases, molecular mechanisms, overview Arabidopsis thaliana
2.3.1.91 evolution evolutionary ancestry of the sinapoyltransferases sinapoylglucose:L-malate sinapoyltransferase and sinapoylglucose:choline sinapoyltransferase with serine carboxypeptidases, molecular mechanisms, overview. Phylogenetic clustering of the sinapoyltransferases SMT and SCT and of sinapine esterase BnSCE3 Brassica napus
2.3.1.91 malfunction a T-DNA insertion mutant lacking SCT activity reveals increased betaine levels in seeds due to increased endogenous choline supply as a consequence of blocked sinapine synthesis Arabidopsis thaliana
2.3.1.91 malfunction down-regulation of BnSCT is accompanied by an increase in the level of free choline that is not channelled into sinapine Brassica napus
2.3.1.91 metabolism 1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase, SGT EC 2.4.1.120, during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase, SCT, and hydrolyzed by sinapoylcholine (sinapine) esterase, SCE, in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase, SMT, pathway of sinapate ester biosynthesis, overview. The metabolic pool size of sinapoylglucose in brassicaceous plants is dependent on its turnover rate, developmentally regulated via differential expression of enzymes involved Arabidopsis thaliana
2.3.1.91 metabolism 1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase, SGT, during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase , SCT, and hydrolyzed by sinapoylcholine (sinapine) esterase, SCE, in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase, SMT, pathway of sinapate ester biosynthesis, overview. The metabolic pool size of sinapoylglucose in brassicaceous plants is dependent on its turnover rate, developmentally regulated via differential expression of enzymes involved Brassica napus
2.3.1.91 physiological function in brassicaceous plants like Arabidpsis thaliana and Brassica napus sinapate is channelled via 1-O-sinapoyl-beta-glucose to various sinapate esters of which 2-O-sinapoyl-L-malate, a proven UV-shielding component, partially accumulates in vacuoles of the leaf epidermis Brassica napus
2.3.1.91 physiological function in brassicaceous plants like Arabidpsis thaliana and Brassica napus sinapate is channelled via 1-O-sinapoyl-beta-glucose to various sinapate esters of which 2-O-sinapoyl-L-malate, a proven UV-shielding component, partially accumulates in vacuoles of the leaf epidermis Arabidopsis thaliana
3.1.1.49 evolution BnSCE3 is classifed as a member of the SGNH hydrolase subfamily of GDSL-lipases which cleave ester bonds in a wide array of lipids. Sinapine esterase BnSCE3 kept the catalytic mechanism of the hydrolytic ancestor but experienced a change in substrate specificity Brassica napus
3.1.1.49 evolution sinapine esterase is classifed as a member of the SGNH hydrolase subfamily of GDSL-lipases which cleave ester bonds in a wide array of lipids Arabidopsis thaliana
3.1.1.49 metabolism 1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase and hydrolyzed by sinapoylcholine (sinapine) esterase in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase. Pathway of sinapate ester biosynthesis, overview Brassica napus
3.1.1.49 metabolism 1-O-sinapoylglucose, produced by UDP-glucose:sinapate glucosyltransferase during seed development, is converted to sinapine by sinapoylglucose:choline sinapoyltransferase and hydrolyzed by sinapoylcholine (sinapine) esterase in germinating seeds. The released sinapate feeds via sinapoylglucose into the biosynthesis of sinapoylmalate in the seedlings catalyzed by sinapoylglucose:L-malate sinapoyltransferase. Pathway of sinapate ester biosynthesis, overview Arabidopsis thaliana
3.1.1.49 additional information SCE activity in seedlings of Brassica napus is mediated by a GDSL lipase-like enzyme designated as BnSCE3, one of three detected SCE isoforms Brassica napus
3.1.1.49 physiological function sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings Arabidopsis thaliana
3.1.1.49 physiological function sinapoylmalate is involved in protecting the leaves against the deleterious effects of UV-B radiation. Sinapine might function as storage vehicle for ready supply of choline for phosphatidylcholine biosynthesis in young seedlings. Antinutritive character of sinapine and related sinapate esters Brassica napus