Leucocyanidin


Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins.

Chemistry

-Leucocyanidin can be synthesized from -dihydroquercetin by reduction with sodium borohydride.
Molar equivalents of synthetic -leucocyanidin and -catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-- and -bi- the all-trans-- and -tri-.

Metabolism

uses leucocyanidin, 2-oxoglutarate, and O2 to produce cis-dihydroquercetin, trans-dihydroquercetin, succinate, CO2, and H2O.
Leucoanthocyanidin reductase uses -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. 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.
The C-4 stereochemistry of leucocyanidin substrates affects anthocyanidin synthase products. This enzyme is an iron and 2-oxoglutarate dependent oxygenase.

Occurrence

Leucoyanidin can be found in Aesculus hippocastanum, Anacardium occidentale, Arachis hypogaea, Areca catechu, Asimina triloba, Cerasus vulgaris, Cinnamomum camphora, Erythroxylon coca, Gleditsia triacanthos, Hamamelis virginiana, Hippophae rhamnoides, Hordeum vulgare, Humulus lupulus, Hypericum perforatum, Laurus nobilis, Magnolia denudata, Malva sylvestris, Musa acuminata × balbisiana, Nelumbo nucifera, Pinus strobus, Prunus serotina ssp. serotina, Psidium guajava, Quercus alba, Quercus robur, Rumex hymenosepalus, Schinus terebinthifolius, Terminalia arjuna, Terminalia catappa, Theobroma cacao, Drimia maritima, Vicia faba, Vitis vinifera, Zea mays, and Ziziphus jujuba.