Combretol

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Combretol
Combretol.svg
Names
IUPAC name
5-Hydroxy-3,3′,4′,5′,7-pentamethoxyflavone
Preferred IUPAC name
5-Hydroxy-3,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one
Other names
3,7,3',4',5'-pentamethylmyricetin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H20O8/c1-23-11-8-12(21)16-13(9-11)28-18(20(27-5)17(16)22)10-6-14(24-2)19(26-4)15(7-10)25-3/h6-9,21H,1-5H3 X mark.svgN
    Key: SUNUQCQIFHHEOW-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C20H20O8/c1-23-11-8-12(21)16-13(9-11)28-18(20(27-5)17(16)22)10-6-14(24-2)19(26-4)15(7-10)25-3/h6-9,21H,1-5H3
    Key: SUNUQCQIFHHEOW-UHFFFAOYAT
  • COC1=CC(=C2C(=C1)OC(=C(C2=O)OC)C3=CC(=C(C(=C3)OC)OC)OC)O
Properties
C20H20O8
Molar mass 388.36 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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Combretol is an O-methylated flavonol, a type of flavonoid. It is the 3,7,3',4',5'-O-methylation of myricetin and can be extracted from Combretum quadrangulare [2] and from Rhodomyrtus tomentosa . [3]

Related Research Articles

Combretaceae Family of flowering plants

The Combretaceae, often called the white mangrove family, are a family of flowering plants in the order Myrtales. The family includes about 530 species of trees, shrubs, and lianas in ca 10 genera. The family includes the leadwood tree, Combretum imberbe. Three genera, Conocarpus, Laguncularia, and Lumnitzera, grow in mangrove habitats (mangals). The Combretaceae are widespread in the subtropics and tropics. Some members of this family produce useful construction timber, such as idigbo from Terminalia ivorensis. The commonly cultivated Quisqualis indica is now placed in the genus Combretum. Many plants in the Quisqualis species contain the Non-proteinogenic amino acid excitotoxin Quisqualic acid, a potent AMPA agonist.

<i>Combretum</i> Genus of plants in Combretaecae family

Combretum, the bushwillows or combretums, make up the type genus of the family Combretaceae. The genus comprises about 272 species of trees and shrubs, most of which are native to tropical and southern Africa, about 5 to Madagascar, but there are others that are native to tropical Asia, New Guinea and the Bismarck Archipelago, Australia, and tropical America. Though somewhat reminiscent of willows (Salix) in their habitus, they are not particularly close relatives of these.

Punicalagin Chemical compound

Punicalagin is an ellagitannin, a type of phenolic compound. It is found in forms alpha and beta in pomegranates, in Terminalia catappa and Terminalia myriocarpa, and in Combretum molle, the velvet bushwillow, a plant species found in South Africa. These three genera are all Myrtales and the last two are both Combretaceae.

<i>Combretum quadrangulare</i> Species of flowering plant

Combretum quadrangulare is a small tree of the family Combretaceae, up to 10 m high. The tree grows wildly or is planted in Vietnam, Cambodia, Laos, Myanmar and Thailand.

Combretum caffrum is the Eastern Cape South African bushwillow tree.

Combretastatin Chemical compound

Combretastatin is a dihydrostilbenoid found in Combretum caffrum.

Brown-backed woodpecker Species of bird

The brown-backed woodpecker is a species of bird in the woodpecker family Picidae. It is found in a belt across the savannah region of sub-Saharan Africa from Senegal in the west to Ethiopia, Kenya and Tanzania in the east. It is generally uncommon, but has a very large range and the population appears to be steady, so the International Union for Conservation of Nature has rated its conservation status as being of "least concern".

Combretastatin A-4 Chemical compound

Combretastatin A-4 is a combretastatin and a stilbenoid. It can be isolated from Combretum caffrum, the Eastern Cape South African bushwillow tree or in Combretum leprosum, the mofumbo, a species found in Brazil.

The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups. O-methylation has an effect on the solubility of flavonoids.

1-<i>alpha</i>-<i>O</i>-Galloylpunicalagin Chemical compound

1-α-O-Galloylpunicalagin is an ester of gallic acid and punicalagin, a type of ellagitannin. It is found in the pomegranate and in Combretum glutinosum.

Punicalin Chemical compound

Punicalin is an ellagitannin. It can be found in Punica granatum (pomegranate) or in the leaves of Terminalia catappa, a plant used to treat dermatitis and hepatitis. It is also reported in Combretum glutinosum, all three species being Myrtales, the two last being Combretaceae.

Pomegranate ellagitannin Ellagitannins found in the pomegranate fruit

The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of pomegranates.

<i>Combretum molle</i> Species of tree

Combretum molle, the velvet bushwillow, is a medium to large tree species in the genus Combretum found in western, eastern and southern Africa.

Combretastatin B-1 Chemical compound

Combretastatin B-1 is a combretastatin and a dihydrostilbenoid. It can be found in Combretum caffrum, the Eastern Cape South African bushwillow tree or in Combretum kraussii, the forest bushwillow.

Dihydrostilbenoid

Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.

Glyptopetalum quadrangulare is a plant in the family Celastraceae. The specific epithet quadrangulare is from the Latin meaning "four-angled", referring to the winged twigs.

<i>Combretum hereroense</i> Species of tree

Combretum hereroense, commonly known as the russet bushwillow and the mouse-eared combretum, is a deciduous shrub or small tree that is found from eastern Africa to northern South Africa. Over its extensive range it is variable with respect to leaf shape, fruit size and indumentum.

Combretum trifoliatum is a vine of the family Combretaceae. It is found from Myanmar across Southeast Asia and Wallacea to New Guinea and Australia. It grows in wet places, including where it can be submerged for four months a year by floodwaters. It is unusual in retaining its photosynthesizing leaves when flooded. Parts of the plant are used in traditional medicine.

References

  1. "KNApSAcK Metabolite Information - C00004777". www.knapsackfamily.com.
  2. Combretol from Combretum quadrangulare. Stang Mongkolsuk, F. M. Dean and L. E. Houghton, J. Chem. Soc. C, 1966, page 125, doi : 10.1039/J39660000125
  3. 5-Hydroxy-3,3',4',5',7-pentamethoxyflavone (combretol). Dachriyanus, R. Fahmi, M. V. Sargent, B. W. Skelton and A. H. White, Acta Crystallogr. (2004). E60, o86-o88