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Literature summary extracted from

  • Liu, C.; Wang, X.; Shulaev, V.; Dixon, R.A.
    A role for leucoanthocyanidin reductase in the extension of proanthocyanidins (2016), Nat. Plants, 2, 16182 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.3.1.77 gene BAN, overexpression of the enzyme in Medicago truncatula hairy roots. Recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots Medicago truncatula
1.17.1.3 gene lar, overexpression of the enzyme in Medicago truncatula hairy roots, conversion of 4beta-(S-cysteinyl)-epicatechin to epicatechin by recombinant LAR Medicago truncatula

Protein Variants

EC Number Protein Variants Comment Organism
1.3.1.77 additional information construction of Tnt1 insertion mutants of gene ANR, two mutants are isolated with Tnt1 insertions in the third and sixth exons, respectively, leading to loss of function of ANR, which gives large reductions in both soluble and insoluble proanthocyanidins in seeds compared to wild-type, low amounts of epicatechin and its 3'-O-glucoside in the anr-1 mutant. The seeds of anr mutants are darkred resulting from redirected metabolic flow from anthocyanidin to anthocyanin. The lar-1/anr-1 double mutant displays the same seed colour as the anr-1 mutant. The anr mutant seeds contain leucocyandin for catechin production, but no substrate for epicatechin production Medicago truncatula
1.17.1.3 K143G no activity with authentic 4beta-(S-cysteinyl)-epicatechin with recombinant mutant LAR Medicago truncatula
1.17.1.3 additional information a lar-1/anr-1 double mutant displays darkred colour resulting from redirected metabolic flow from anthocyanidin to anthocyanin Medicago truncatula

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.3.1.77 cyanidin + 2 NADPH + H+ Medicago truncatula
-
(2R,3R)-epicatechin + 2 NADP+ ? ?
1.3.1.77 cyanidin + 2 NADPH + H+ Medicago truncatula ecotype R108
-
(2R,3R)-epicatechin + 2 NADP+ ? ?
1.3.1.77 additional information Medicago truncatula recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots ?
-
?
1.3.1.77 additional information Medicago truncatula ecotype R108 recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots ?
-
?
1.17.1.3 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+ Medicago truncatula
-
(2R,3S)-catechin + NADP+ + H2O
-
?
1.17.1.3 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+ Medicago truncatula ecotype R108
-
(2R,3S)-catechin + NADP+ + H2O
-
?
1.17.1.3 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ Medicago truncatula enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner in hairy roots. 4beta-(S-Cysteinyl)-epicatechin provides the extension unit during procyanidin polymerization epicatechin + cysteine + NADP+
-
?
1.17.1.3 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ Medicago truncatula ecotype R108 enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner in hairy roots. 4beta-(S-Cysteinyl)-epicatechin provides the extension unit during procyanidin polymerization epicatechin + cysteine + NADP+
-
?

Organism

EC Number Organism UniProt Comment Textmining
1.3.1.77 Medicago truncatula Q84XT1
-
-
1.3.1.77 Medicago truncatula ecotype R108 Q84XT1
-
-
1.17.1.3 Medicago truncatula Q3KN75
-
-
1.17.1.3 Medicago truncatula ecotype R108 Q3KN75
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.3.1.77 hairy root
-
Medicago truncatula
-
1.3.1.77 seed coat
-
Medicago truncatula
-
1.17.1.3 seed coat
-
Medicago truncatula
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.1.77 cyanidin + 2 NADPH + H+
-
Medicago truncatula (2R,3R)-epicatechin + 2 NADP+ ? ?
1.3.1.77 cyanidin + 2 NADPH + H+
-
Medicago truncatula ecotype R108 (2R,3R)-epicatechin + 2 NADP+ ? ?
1.3.1.77 additional information recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots Medicago truncatula ?
-
?
1.3.1.77 additional information recombinant enzyme ANR does not generate epicatechin from epicatechin-cysteine conjugate in hairy roots Medicago truncatula ecotype R108 ?
-
?
1.17.1.3 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
-
Medicago truncatula (2R,3S)-catechin + NADP+ + H2O
-
?
1.17.1.3 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
-
Medicago truncatula ecotype R108 (2R,3S)-catechin + NADP+ + H2O
-
?
1.17.1.3 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner in hairy roots. 4beta-(S-Cysteinyl)-epicatechin provides the extension unit during procyanidin polymerization Medicago truncatula epicatechin + cysteine + NADP+
-
?
1.17.1.3 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner Medicago truncatula epicatechin + cysteine + NADP+
-
?
1.17.1.3 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner in hairy roots. 4beta-(S-Cysteinyl)-epicatechin provides the extension unit during procyanidin polymerization Medicago truncatula ecotype R108 epicatechin + cysteine + NADP+
-
?
1.17.1.3 4beta-(S-cysteinyl)-epicatechin + NADPH + H+ enzyme LAR generates epicatechin from epicatechin-cysteine conjugate in an NADPH-dependent manner Medicago truncatula ecotype R108 epicatechin + cysteine + NADP+
-
?

Synonyms

EC Number Synonyms Comment Organism
1.3.1.77 ANR
-
Medicago truncatula
1.3.1.77 BAN
-
Medicago truncatula
1.17.1.3 LAR
-
Medicago truncatula
1.17.1.3 MtLAR
-
Medicago truncatula

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.17.1.3 22
-
assay at room temperature Medicago truncatula

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.17.1.3 7
-
assay at Medicago truncatula

Cofactor

EC Number Cofactor Comment Organism Structure
1.3.1.77 NADPH
-
Medicago truncatula
1.17.1.3 NADPH
-
Medicago truncatula

Expression

EC Number Organism Comment Expression
1.3.1.77 Medicago truncatula overexpression of the myeloblastosis (MYB)14 or MYB5 transcription factors induces proanthocyanidin biosynthesis in hairy roots, ANR is highly induced in MYB5 overexpressing hairy roots up
1.17.1.3 Medicago truncatula overexpression of the myeloblastosis (MYB)14 or MYB5 transcription factors induces proanthocyanidin biosynthesis in hairy roots, LAR is induced in MYB5 overexpressing hairy roots up

General Information

EC Number General Information Comment Organism
1.3.1.77 malfunction loss of function ANR mutants show large reductions in both soluble and insoluble proanthocyanidins in seeds compared to wild-type, as well as low amounts of epicatechin and its 3'-O-glucoside in the anr-1 mutant. The seeds of anr mutants are darkred resulting from redirected metabolic flow from anthocyanidin to anthocyanin Medicago truncatula
1.17.1.3 metabolism flavan-3-ols are synthesized through the flavonoid pathway via leucoanthocyanidin and anthocyanidin. Leucoanthocyanidin can be converted to (+)-flavan-3-ol, e.g. (+)-catechin, by leucoanthocyanidin reductase (LAR) or to anthocyanidin by anthocyanidin synthase (ANS) Medicago truncatula
1.17.1.3 additional information molecular modelling and molecular docking of epicatechin-cysteine to MtLAR, based on the crystal structure of Vitis vinifera LAR Medicago truncatula
1.17.1.3 physiological function role for leucoanthocyanidin reductase in the extension of proanthocyanidins. Monomeric flavan-3-ols do not dimerize in autopolymerization assays, whereas procyanidin B2 oligomerizes, either alone or with monomeric flavan-3-ols, suggesting that formation of epicatechin carbocation is a crucial step for proanthocyanidin assembly Medicago truncatula