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Names | |
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IUPAC name (2R,3S,4S)-Flavan-3,3′,4,4′,5,7-hexol | |
Systematic IUPAC name (2R,3S,4S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol | |
Other names Leucocianidol Leucocianidolum Leucocyanidol Leukocyanidine Procyanidol Resivit Leucoanthocyanidol Vitamin P faktor 3,4-Cyanidiol (2R,3S,4S)-3,4,5,7,4-pentahydroxyflavan | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C15H14O7 | |
Molar mass | 306.26 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins.
(+)-Leucocyanidin can be synthesized from (+)-dihydroquercetin by reduction with sodium borohydride. [1]
Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-[4,8]- and [4,6]-bi-[(+)-catechins] (procyanidins B3, B6) the all-trans-[4,8:4,8]- and [4,8:4,6]-tri-[(+)-catechins] (procyanidin C2 and isomer). [2]
Leucocyanidin oxygenase uses leucocyanidin, 2-oxoglutarate, and O2 to produce cis-dihydroquercetin, trans-dihydroquercetin (taxifolin), succinate, CO2, and H2O.
Leucoanthocyanidin reductase (LAR or leucocyanidin reductase LCR) uses (2R,3S)-catechin, NADP+, and H2O to produce 2,3-trans-3,4-cis-leucocyanidin, NADPH, and H+. Its gene expression has been studied in developing grape berries and grapevine leaves. [3] Its activity has also been measured in leaves, flowers, and seeds of the legumes Medicago sativa , Lotus japonicus , Lotus uliginosus , Hedysarum sulfurescens , and Robinia pseudoacacia . [4]
The C-4 stereochemistry of leucocyanidin substrates affects anthocyanidin synthase (ANS) products. This enzyme is an iron(II) and 2-oxoglutarate (2OG) dependent oxygenase. [5]
Leucoyanidin can be found in these plants: [6]