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 (2R,3S,4R or S)-leucocyanidin and (+)-
catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-''trans''-
,8 and
,6bi-
+)-catechins(
procyanidins B3,
B6) the all-''trans''-
,8:4,8 and
,8:4,6tri-
+)-catechins(
procyanidin C2 and isomer).
Metabolism
Leucocyanidin oxygenase uses leucocyanidin, 2-oxoglutarate, and O
2 to produce ''cis''-dihydroquercetin, ''trans''-
dihydroquercetin (taxifolin), succinate, CO
2, and H
2O.
Leucoanthocyanidin reductase (LAR or leucocyanidin reductase LCR) uses (2''R'',3''S'')-
catechin,
NADP+, and H
2O 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 (ANS) products. This enzyme is an iron(II) and 2-oxoglutarate (2OG) dependent oxygenase.
Occurrence
Leucoyanidin can be found in these plants:
*''
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 rhamnoides'', also known as sea buckthorn, sandthorn, sallowthorn or seaberry, is a species of flowering plant in the family Elaeagnaceae, native to cold-temperate regions of Eurasia. It is a spiny deciduous shrub. The plant is used ...
'' (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
''Nelumbo nucifera'', also known as the pink lotus, sacred lotus, Indian lotus, or simply lotus, is one of two extant taxon, extant species of aquatic plant in the Family (biology), family Nelumbonaceae. It is sometimes colloquially called a ...
'' (Baladi bean)
*''
Pinus strobus'' (Eastern white pine)
*''
Prunus serotina'' ssp. serotina (black cherry)
*''
Psidium guajava'' (Common guava)
*''
Quercus alba
''Quercus alba'', the white oak, is one of the preeminent hardwoods of eastern and central North America. It is a long-lived oak, native to eastern and central North America and found from Minnesota, Ontario, Quebec, and southern Maine south as ...
'' (White oak)
*''
Quercus robur'' (Common oak)
*''
Rumex hymenosepalus'' (Arizona dock)
*''
Schinus terebinthifolius'' (Brazilian pepper tree)
*''
Terminalia arjuna'' (arjun)
*''
Terminalia catappa
''Terminalia catappa'' is a large Tropics, tropical tree in the leadwood tree family, Combretaceae, native to Asia, Australia, the Pacific, Madagascar and Seychelles. Common names in English include country almond, Indian almond, Malabar almond, ...
'' (Indian almond)
*''
Theobroma cacao
''Theobroma cacao'' (cacao tree or cocoa tree) is a small ( tall) evergreen tree in the Malvaceae family. Its seedscocoa beansare used to make chocolate liquor, cocoa solids, cocoa butter and chocolate. Although the tree is native to the tropi ...
'' (Cacao)
*''
Drimia maritima'' (Sea Squill)
*''
Vicia faba
''Vicia faba'', commonly known as the broad bean, fava bean, or faba bean, is a species of vetch, a flowering plant in the pea and bean family Fabaceae. It is widely cultivated as a crop for human consumption, and also as a cover crop. Vari ...
'' (bell-bean)
*''
Vitis vinifera
''Vitis vinifera'', the common grape vine, is a species of flowering plant, native to the Mediterranean Basin, Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern ...
'' (common grape vine)
*''
Zea mays
Maize (; ''Zea mays''), also known as corn in North American English, is a tall stout Poaceae, grass that produces cereal grain. It was domesticated by indigenous peoples of Mexico, indigenous peoples in southern Mexico about 9,000 years ago ...
'' (corn, maize)
*''
Ziziphus jujuba'' (jujube, Chinese date).
References
{{Leucoanthocyanidin
Leucoanthocyanidins
Catechols
Resorcinols