Leucocyanidin

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

Leucocyanidin

Names
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
CAS Number	480-17-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:11412 Y
ChEMBL	ChEMBL124022 Y
ChemSpider	389677 Y
PubChem CID	440833
UNII	RAP1D6110C Y
CompTox Dashboard (EPA)	DTXSID70331530
InChI InChI=1S/C15H14O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,13-21H/t13-,14-,15+/m0/s1 Y Key: SBZWTSHAFILOTE-SOUVJXGZSA-N Y
SMILES C1=CC(=C(C=C1[C@@H]2[C@H]([C@H](C3=C(C=C(C=C3O2)O)O)O)O)O)O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

Chemistry

(+)-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]

Metabolism

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]

Occurrence

Leucoyanidin can be found in these plants:^[6]

• Aesculus hippocastanum (Horse chestnut)
• Anacardium occidentale (Cashew, acajou)
• Arachis hypogaea (peanut)
• Areca catechu (Areca nut)
• Asimina triloba (American custardapple)
• Cerasus vulgaris (Cherry)
• Cinnamomum camphora (Camphor)
• Erythroxylon coca (coca)
• Gleditsia triacanthos (Honey locust)
• Hamamelis virginiana (American Witch Hazel)
• Hippophae rhamnoides (Hippophae berry Sanddorn)
• Hordeum vulgare (Barley)
• Humulus lupulus (bine)
• Hypericum perforatum (perikon Amber)
• Laurus nobilis
• Magnolia denudata (Hsin-I Yulan-Magnolie)
• Malva sylvestris (Blue mallow)
• Musa acuminata × balbisiana (Banana)
• Nelumbo nucifera (Baladi bean)
• Pinus strobus (Eastern white pine)
• Prunus serotina ssp. serotina (black cherry)
• Psidium guajava (Common guava)
• Quercus alba (White oak)
• Quercus robur (Common oak)
• Rumex hymenosepalus (Arizona dock)
• Schinus terebinthifolius (Brazilian pepper tree)
• Terminalia arjuna (arjun)
• Terminalia catappa (Indian almond)
• Theobroma cacao (Cacao)
• Drimia maritima (Sea Squill)
• Vicia faba (bell-bean)
• Vitis vinifera (common grape vine)
• Zea mays (corn, maize)
• Ziziphus jujuba (jujube, Chinese date).