Leucodelphinidin

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Leucodelphinidin
Leucodelphinidin.svg
Names
IUPAC name
(2R,3S,4S)-Flavan-3,3′,4,4′,5,5′,7-heptol
Systematic IUPAC name
(2R,3S,4S)-2-(3,4,5-Trihydroxyphenyl)-2H-1-benzopyran-3,4,5,7-tetrol
Other names
leukoefdin
Leucoefdin
leucodelfinidin
Leucoephdine
Leukoephdin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C15H14O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,13-22H/t13-,14-,15+/m0/s1 X mark.svgN
    Key: ZEACOKJOQLAYTD-SOUVJXGZSA-N X mark.svgN
  • InChI=1/C15H14O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,13-22H/t13-,14-,15+/m0/s1
    Key: ZEACOKJOQLAYTD-SOUVJXGZBJ
  • C1=C(C=C(C(=C1O)O)O)C2C(C(C3=C(C=C(C=C3O2)O)O)O)O
Properties
C15H14O8
Molar mass 322.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Leucodelphinidin is a colorless chemical compound related to leucoanthocyanidins. It can be found in Acacia auriculiformis , [1] in the bark of Karada ( Cleistanthus collinus ) and in the kino (gum) from Eucalyptus pilularis . [2]

Other species containing leucodelphinidin include Aesculus hippocastanum (Horse chestnut, in rind/bark/cortex), Arachis hypogaea (Earth nut in seeds), Arbutus unedo (Arbutus, in the leaf), Caesalpinia pulcherrima (Barbados pride), Ceratonia siliqua (Carob, in the fruit), Hamamelis virginiana (American witch hazel, in the leaf), Hippophae rhamnoides (Hippophae berry, in the leaf), Humulus lupulus (bine flower / blossom, in the leaf), Musa acuminata × balbisiana (Banana, in the fruit), Nelumbo nucifera (lotus, in the leaf), Phyllanthus emblica (Emblic, Indian gooseberry, in the rind/bark/cortex), Quercus alba (White oak, in the rind/bark/cortex), Quercus robur (Common oak, in the rind/bark/cortex), Rumex hymenosepalus (Arizona dock, in the root), Schinus molle (California peppertree, in the leaf) and Vicia faba (bell-bean, in the seed). [3]

A leucodelphinidin derivative isolated from Ficus bengalensis shows hypoglycemic effects. [4]

Metabolism

Dihydroflavonol 4-reductase (DFR) uses dihydromyricetin (ampelopsin) NADPH and 2 H+ to produce leucodelphinidin and NADP. [5] [6]

Related Research Articles

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An oak is a hardwood tree or shrub in the genus Quercus of the beech family. They have spirally arranged leaves, often with lobed edges, and a nut called an acorn, borne within a cup. The genus is widely distributed in the Northern Hemisphere; it includes some 500 species, both deciduous and evergreen. Fossil oaks date back to the Middle Eocene. Molecular phylogeny shows that the genus is divided into Old World and New World clades, but many oak species hybridise freely, making the genus's history difficult to resolve.

<i>Quercus rubra</i> Species of flowering plant in the beech and oak family Fagaceae

Quercus rubra, the northern red oak, is an oak tree in the red oak group. It is a native of North America, in the eastern and central United States and southeast and south-central Canada. It has been introduced to small areas in Western Europe, where it can frequently be seen cultivated in gardens and parks. It prefers good soil that is slightly acidic. Often simply called red oak, northern red oak is so named to distinguish it from southern red oak (Q. falcata), also known as the Spanish oak. Northern red oak is sometimes called champion oak.

<i>Quercus suber</i> Species of plant

Quercus suber, commonly called the cork oak, is a medium-sized, evergreen oak tree in the section Quercus sect. Cerris. It is the primary source of cork for wine bottle stoppers and other uses, such as cork flooring and as the cores of cricket balls. It is native to southwest Europe and northwest Africa. In the Mediterranean basin the tree is an ancient species with fossil remnants dating back to the Tertiary period. It can survive for as long as two centuries. Typically, once it reaches 25 years old, its thick bark can be harvested for cork every 9 to 12 years without causing harm to the tree.

<i>Acacia auriculiformis</i> Species of legume

Acacia auriculiformis, commonly known as earleaf acacia, earpod wattle, auri, karuvel and aakashmani, is a fast-growing, crooked, gnarly tree in the family Fabaceae. It is native to Australia, Philippines, Indonesia, and Papua New Guinea. It grows up to 30 metres (98 ft) tall. Acacia auriculiformis has about 47,000 seeds per kilogram (21,000/lb).

<i>Opuntia ficus-indica</i> Species of cactus

Opuntia ficus-indica, the Indian fig opuntia, fig opuntia, or prickly pear, is a species of cactus that has long been a domesticated crop plant grown in agricultural economies throughout arid and semiarid parts of the world. O. ficus-indica is the most widespread and most commercially important cactus. It is grown primarily as a fruit crop, and also for the vegetable nopales and other uses. Cacti are good crops for dry areas because they efficiently convert water into biomass. O. ficus-indica, as the most widespread of the long-domesticated cactuses, is as economically important as maize and blue agave in Mexico. Opuntia species hybridize easily, but the wild origin of O. ficus-indica is likely to have been in central Mexico, where its closest genetic relatives are found.

<i>Hippophae rhamnoides</i> Species of flowering plant

Hippophae rhamnoides, also known as sea-buckthorn, is a species of flowering plant in the family Elaeagnaceae, native to the cold-temperate regions of Europe and Asia. It is a spiny deciduous shrub. The plant is used in the food and cosmetics industries, in traditional medicine, as animal fodder, in horticulture, and for ecological purposes.

<i>Acacia</i> Genus of plants

Acacia, commonly known as wattles or acacias, is a genus of about 1,084 species of shrubs and trees in the subfamily Mimosoideae of the pea family Fabaceae. Initially, it comprised a group of plant species native to Africa, South America, and Australasia, but is now reserved for species mainly from Australia, with others from New Guinea, Southeast Asia, and the Indian Ocean. The genus name is Neo-Latin, borrowed from the Greek ἀκακία, a term used in antiquity to describe a preparation extracted from Vachellia nilotica, the original type species.

<i>Acacia mearnsii</i> Species of flowering plant

Acacia mearnsii, commonly known as black wattle, late black wattle or green wattle, is a species of flowering plant in the family Fabaceae and is endemic to south-eastern Australia. It is usually an erect tree with smooth bark, bipinnate leaves and spherical heads of fragrant pale yellow or cream-coloured flowers followed by black to reddish brown pods. In some other parts of the world, it is regarded as an invasive species.

<i>Vachellia nilotica</i> Species of flowering plant in the bean family Fabaceae

Vachellia nilotica, more commonly known as Acacia nilotica, and by the vernacular names of gum arabic tree, babul, thorn mimosa, Egyptian acacia or thorny acacia, is a flowering tree in the family Fabaceae. It is native to Africa, the Middle East and the Indian subcontinent. It is also considered a 'weed of national significance' and an invasive species of concern in Australia, as well as a noxious weed by the federal government of the United States.

<i>Vateria indica</i> Species of tree

Vateria indica, the white dammar, is a species of tree in the family Dipterocarpaceae. It is endemic to the Western Ghats mountains in India. It is threatened by habitat loss. It is a large canopy or emergent tree frequent in tropical wet evergreen forests of the low and mid-elevations.

<span class="mw-page-title-main">Tanbark</span> Tree bark used for tanning

Tanbark is the bark of certain species of trees, traditionally used for tanning hides into leather.

<i>Tabebuia rosea</i> Species of tree

Tabebuia rosea, also called pink poui, and rosy trumpet tree is a neotropical tree that grows up to 30 m (98 ft) and can reach a diameter at breast height of up to 100 cm (3 ft). The Spanish name roble de sabana, meaning "savannah oak", is widely used in Costa Rica, probably because it often remains in heavily deforested areas and because of the resemblance of its wood to that of oak trees. It is the national tree of El Salvador, where it is called "Maquilíshuat".

<span class="mw-page-title-main">Leucocyanidin</span> Chemical compound

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

<span class="mw-page-title-main">Leucopeonidin</span> Chemical compound

Leucopeonidin is a leucoanthocyanidin.

<span class="mw-page-title-main">Procyanidin B2</span> Chemical compound

Procyanidin B2 is a B type proanthocyanidin. Its structure is (−)-Epicatechin-(4β→8)-(−)-epicatechin.

<span class="mw-page-title-main">Castalagin</span> Chemical compound

Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Terminalia leiocarpa and Terminalia avicennoides.

<i>Quercus infectoria</i> Species of oak tree

Quercus infectoria or the Aleppo oak is a species of oak well known for producing galls that have been traditionally used for centuries in Asia medicinally while also used in softening leather and in making black dye and ink.

<i>Ziziphus oenopolia</i> Species of flowering plant

Ziziphus oenopolia, commonly known as the jackal jujube, small-fruited jujube or wild jujube, is a flowering plant with a broad distribution through tropical and subtropical Asia and Australasia. In India, it is mostly found in the deciduous forests of the southern part of the country.

<i>Clerodendrum infortunatum</i> Species of flowering plant

Clerodendrum infortunatum, known as bhat or hill glory bower, is a perennial shrub belonging to the family Lamiaceae, also sometimes classified under Verbenaceae. It is the type species among ~150 species of Clerodendrum. It is one of the most well-known natural health remedies in traditional practices and siddha medicine.

References

  1. Drewes, S. E.; Roux, D. G. (1966). "A new flavan-3,4-diol from Acacia auriculiformis by paper ionophoresis". Biochemical Journal. 98 (2): 493–500. doi:10.1042/bj0980493. PMC   1264869 . PMID   5941342.
  2. Ganguly, A.K.; Seshadri, T.R.; Subramanian, P. (1958). "A study of leucoanthocyanidins of plants—I". Tetrahedron. 3 (3): 225–229. doi:10.1016/0040-4020(58)80017-4.
  3. Leucodelphinidin on liberherbarum.com
  4. Geetha, B. S.; Mathew, B. C.; Augusti, K. T. (1994). "Hypoglycemic effects of leucodelphinidin derivative isolated from Ficus bengalensis (Linn)". Indian Journal of Physiology and Pharmacology. 38 (3): 220–222. PMID   7814088.
  5. leucodelphinidin biosynthesis pathway proposed on biocyc.org
  6. Les cibles d’amélioration pour la qualité des raisins: L’exemple des flavonoïdes, Nancy Terrier (French) [ permanent dead link ]