Leucocyanidin
Encyclopedia
Leucocyanidin is a colorless chemical compound related to leucoanthocyanidin
s. Leucoyanidin can be found in Aesculus hippocastanum (Horse chestnut), Anacardium occidentale (Cashew, acajou), Arachis hypogaea (Earth Nut), 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 silvestris (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, mais), Ziziphus jujuba (jujube, Chinese date).
(+)Leucocyanidin can be synthesized from (+)dihydroquercetin by sodium borohydride
reduction.
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. 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 (20G) dependent oxygenase.
Leucoanthocyanidin
Leucoanthocyanidin are colorless chemical compounds related to anthocyanidins and anthocyanins. Leucoanthocyanins can be found in Anadenanthera peregrina and in several species of Nepenthes including Nepenthes rajah, Nepenthes burbidgeae, Nepenthes tentaculata, Nepenthes × alisaputrana and...
s. Leucoyanidin can be found in Aesculus hippocastanum (Horse chestnut), Anacardium occidentale (Cashew, acajou), Arachis hypogaea (Earth Nut), Areca catechu
Areca catechu
Areca catechu is the areca palm or areca nut palm, , a species of palm which grows in much of the tropical Pacific, Asia, and parts of east Africa. The palm is believed to have originated in either Malaysia or the Philippines...
(Areca nut), Asimina triloba
Asimina triloba
Asimina triloba, the pawpaw, paw paw, paw-paw, or common pawpaw, is a species of Asimina in the same plant family as the custard-apple, cherimoya, sweetsop, ylang-ylang and soursop...
(American custardapple), Cerasus vulgaris (Cherry), Cinnamomum camphora (Camphor), Erythroxylon coca (coca), Gleditsia triacanthos (Honey locust), Hamamelis virginiana
Hamamelis virginiana
Hamamelis virginiana is a species of Witch-hazel native to eastern North America, from Nova Scotia west to Minnesota, and south to central Florida to eastern Texas....
(American Witch Hazel), Hippophae rhamnoides
Hippophae rhamnoides
Hippophae rhamnoides, the common sea-buckthorn, is a deciduous shrub species in the genus Hippophae.Common Sea-buckthorn branches are dense, stiff, and very thorny. The leaves are a distinct pale silvery-green, lanceolate, 3-8 cm long and less than 7 mm broad. It is dioecious, with male and female...
(Hippophae berry Sanddorn), Hordeum vulgare (Barley), Humulus lupulus
Humulus lupulus
Humulus lupulus is a species of Humulus in the Cannabaceae family.Common hop is a dioecious, perennial herbaceous climbing plant which sends up new shoots in early spring and dies back to the cold-hardy rhizome in autumn...
(bine), Hypericum perforatum (perikon Amber), Laurus nobilis, Magnolia denudata (Hsin-I Yulan-Magnolie), Malva silvestris (Blue mallow), Musa acuminata × balbisiana
Banana
Banana is the common name for herbaceous plants of the genus Musa and for the fruit they produce. Bananas come in a variety of sizes and colors when ripe, including yellow, purple, and red....
(Banana), Nelumbo nucifera
Nelumbo nucifera
Nelumbo nucifera, known by a number of names including Indian Lotus, Sacred Lotus, Bean of India, or simply Lotus, is a plant in the monogeneric family Nelumbonaceae...
(Baladi bean), Pinus strobus (Eastern white pine), Prunus serotina ssp. serotina (black cherry), Psidium guajava
Psidium guajava
The apple guava or common guava is an evergreen shrub or small tree native to Mexico, the Caribbean, and Central and South America...
(Common guava), Quercus alba (White oak), Quercus robur (Common oak), Rumex hymenosepalus
Rumex hymenosepalus
Rumex hymenosepalus, commonly known as canaigre, ganagra, wild rhubarb, Arizona dock, or tanner's dock, is a perennial flowering plant which is native to the United States and Mexico. It has been cultivated in the southwestern United States as the roots are a good source of tannin, for use in...
(Arizona dock), Schinus terebinthifolius (Brazilian pepper tree), Terminalia arjuna
Terminalia arjuna
Terminalia arjuna is a tree of the genus Terminalia.-Description:...
(arjun), Terminalia catappa
Terminalia catappa
Terminalia catappa is a large tropical tree in the Leadwood tree family, Combretaceae. The tree has been spread widely by humans and the native range is uncertain. It has long been naturalised in a broad belt extending from Africa to Northern Australia and New Guinea through Southeast Asia and...
(Indian almond), Theobroma cacao (Cacao), Drimia maritima (Sea Squill), Vicia faba
Vicia faba
This article refers to the Broad Bean plant. For Broadbean the company, see Broadbean, Inc.Vicia faba, the Broad Bean, Fava Bean, Field Bean, Bell Bean or Tic Bean, is a species of bean native to north Africa and southwest Asia, and extensively cultivated elsewhere. A variety is provisionally...
(bell-bean), Vitis vinifera
Vitis vinifera
Vitis vinifera is a species of Vitis, native to the Mediterranean region, central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern Iran....
(Common Grape Vine), Zea Mays (Corn, mais), Ziziphus jujuba (jujube, Chinese date).
(+)Leucocyanidin can be synthesized from (+)dihydroquercetin by sodium borohydride
Sodium borohydride
Sodium borohydride, also known as sodium tetrahydridoborate, is an inorganic compound with the formula NaBH4. This white solid, usually encountered as a powder, is a versatile reducing agent that finds wide application in chemistry, both in the laboratory and on a technical scale. Large amounts are...
reduction.
Metabolism
Leucocyanidin oxygenaseLeucocyanidin oxygenase
In enzymology, a leucocyanidin oxygenase is an enzyme that catalyzes the chemical reactionThe 3 substrates of this enzyme are leucocyanidin, 2-oxoglutarate, and O2, whereas its 5 products are cis-dihydroquercetin, trans-dihydroquercetin, succinate, CO2, and H2O.This enzyme belongs to the family of...
uses leucocyanidin, 2-oxoglutarate, and O2 to produce cis-dihydroquercetin, trans-dihydroquercetin (taxifolin), succinate, CO2, and H2O.
Leucoanthocyanidin reductase
Leucoanthocyanidin reductase
In enzymology, a leucoanthocyanidin reductase is an enzyme that catalyzes the chemical reaction-catechin + NADP+ + H2O \rightleftharpoons 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+...
(LAR or leucocyanidin reductase LCR) uses (2R,3S)-catechin
Catechin
Catechin is a natural phenol antioxidant plant secondary metabolite. The term catechins is also commonly used to refer to the related family of flavonoids and the subgroup flavan-3-ols ....
, NADP+
Nicotinamide adenine dinucleotide phosphate
Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or TPN in older notation , is a coenzyme used in anabolic reactions, such as lipid and nucleic acid synthesis, which require NADPH as a reducing agent....
, 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 japonicus
Lotus japonicus is a wild legume that belongs to family Fabaceae. Members of this family are very diverse, constituting about 20,000 species. They are of significant agricultural and biological importance as many of the legume species are rich sources of protein and oil and can also fix atmospheric...
, Lotus uliginosus
Lotus uliginosus
Lotus pedunculatus , Greater Bird's-foot Trefoil or Marsh Bird's-foot Trefoil is a member of the pea family ....
, 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 (20G) dependent oxygenase.