Genkwanin

Last updated
Genkwanin
Genkwanin v2.svg
Genkwanin molecule ball.png
Names
IUPAC name
4′,5-Dihydroxy-7-methoxyflavone
Systematic IUPAC name
5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Other names
Gengkwanin
Apigenin 7-methyl ether
4′,5-dihydroxy-7-methoxy flavone
5,4′-Dihydroxy-7-methoxyflavone
5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.195.986 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3 X mark.svgN
    Key: JPMYFOBNRRGFNO-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
    Key: JPMYFOBNRRGFNO-UHFFFAOYAO
  • COC1=CC(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O
  • COc1cc(c2c(=O)cc(oc2c1)c3ccc(cc3)O)O
Properties
C16H12O5
Molar mass 284.267 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Genkwanin is an O-methylated flavone, a type of flavonoid. It can be found in the seeds of Alnus glutinosa , [1] in the leaves of the ferns Notholaena bryopoda and Asplenium normale , [2] and in the leaves of trees in the genus Aquilaria . [3]

Related Research Articles

<span class="mw-page-title-main">Alder</span> Genus of flowering plants in the birch family Betulaceae

Alders are trees that compose the genus Alnus in the birch family Betulaceae. The genus includes about 35 species of monoecious trees and shrubs, a few reaching a large size, distributed throughout the north temperate zone with a few species extending into Central America, as well as the northern and southern Andes.

<span class="mw-page-title-main">Fern</span> Class of vascular plants

The ferns are a group of vascular plants that reproduce via spores and have neither seeds nor flowers. They differ from mosses by being vascular, i.e., having specialized tissues that conduct water and nutrients, and in having life cycles in which the branched sporophyte is the dominant phase.

<i>Alnus glutinosa</i> Species of flowering plant in the birch family Betulaceae

Alnus glutinosa, the common alder, black alder, European alder, European black alder, or just alder, is a species of tree in the family Betulaceae, native to most of Europe, southwest Asia and northern Africa. It thrives in wet locations where its association with the bacterium Frankia alni enables it to grow in poor quality soils. It is a medium-sized, short-lived tree growing to a height of up to 30 metres (98 feet). It has short-stalked rounded leaves and separate male and female flowers in the form of catkins. The small, rounded fruits are cone-like and the seeds are dispersed by wind and water.

<i>Alnus rubra</i> Species of tree

Alnus rubra, the red alder, is a deciduous broadleaf tree native to western North America.

<i>Alnus incana</i> Species of tree

Alnus incana, the grey alder, tag alder or speckled alder, is a species of multi-stemmed, shrubby tree in the birch family, with a wide range across the cooler parts of the Northern Hemisphere. Tolerant of wetter soils, it can slowly spread with runners and is a common sight in swamps and wetlands.

<i>Alnus cordata</i> Species of plant

Alnus cordata, the Italian alder, is a tree or shrub species belonging to the family Betulaceae, and native to the southern Apennine Mountains and the north-eastern mountains of Corsica. It has been introduced in Sicily, Sardinia, and more recently in Central-Northern Italy, other European countries and extra-European countries, where it has become naturalised.

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

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

<i>Coleophora</i> Genus of moths

Coleophora is a very large genus of moths of the family Coleophoridae. It contains some 1,350 described species. The genus is represented on all continents, but the majority are found in the Nearctic and Palaearctic regions. Many authors have tried splitting the genus into numerous smaller ones, but most of these have not become widely accepted.

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

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

<i>Scutellaria lateriflora</i> Species of flowering plant

Scutellaria lateriflora, is a hardy perennial herb of the mint family, Lamiaceae, native to North America.

<i>Aquilaria sinensis</i> Species of agarwood tree from China

Aquilaria sinensis, known as incense tree, is a species of plant in the family Thymelaeaceae. It is endemic to China. It is threatened by habitat loss. This medicinal plant is a source of fragrant wood, formed under a pathological condition, called agarwood.

<span class="mw-page-title-main">Anthocyanin</span> Class of plant-based pigments

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart named a chemical compound that gives flowers a blue color, Anthokyan, in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

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

Acacetin is a 4′-O-methylated flavone of the parent compound apigenin, found in Robinia pseudoacacia, Turnera diffusa (damiana), Betula pendula, and in the fern Asplenium normale.

<i>Phyllonorycter stettinensis</i> Species of moth

Phyllonorycter stettinensis is a moth of the family Gracillariidae. It is found from Scandinavia and Finland to the Pyrenees, Corsica, Italy and Bulgaria and from Great Britain to Russia.

<i>Phyllonorycter klemannella</i> Species of moth

Phyllonorycter klemannella is a moth of the family Gracillariidae. It is known from all of Europe, except Greece.

<i>Phyllonorycter rajella</i> Species of moth

Phyllonorycter rajella is a moth of the family Gracillariidae. It is known from all of Europe, except the Iberian Peninsula and Greece.

<i>Frankia alni</i> Species of bacterium

Frankia alni is a Gram-positive species of actinomycete filamentous bacterium that lives in symbiosis with actinorhizal plants in the genus Alnus. It is a nitrogen-fixing bacterium and forms nodules on the roots of alder trees.

<i>Alnus serrulata</i> Species of tree

Alnus serrulata, the hazel alder or smooth alder, is a thicket-forming shrub in the family Betulaceae. It is native to eastern North America and can be found from western Nova Scotia and southern New Brunswick south to Florida and Texas.

<i>Heliozela resplendella</i> Species of moth

Heliozela resplendella is a moth of the Heliozelidae family. It is found from Fennoscandia and northern Russia to the Pyrenees, Alps and Romania and from Ireland to the Baltic region.

<i>Eriocampa ovata</i> Species of sawfly

Eriocampa ovata, known generally as the alder sawfly or woolly alder sawfly, is a species of common sawfly in the family Tenthredinidae. The larvae feed on the leaves of the common alder and the grey alder, sometimes causing defoliation.

References

  1. O'Rourke, Ciara; Byres, Maureen; Delazar, Abbas; Kumarasamy, Yashodharan; Nahar, Lutfun; Stewart, Fiona; Sarker, Satyajit D. (2005). "Hirsutanonol, oregonin and genkwanin from the seeds of Alnus glutinosa (Betulaceae)". Biochemical Systematics and Ecology. 33 (7): 749–752. doi:10.1016/j.bse.2004.10.005. Archived from the original on 2012-08-23. Retrieved 2010-02-23.
  2. UmiKalsom, Yusuf; Harborne, Jeffrey B. (1991). "Flavonoid distribution in asplenioid ferns". Pertanika. 14 (3): 297–300.
  3. Kakino, Mamoru; Hara, Hideaki (2016). "Pharmacological Effects of Aquilaria SPP. Leaves and Their Chemical Constituents". Agarwood. Tropical Forestry. pp. 125–136. doi:10.1007/978-981-10-0833-7_8. ISBN   978-981-10-0832-0.