Genkwanin

Last updated
Genkwanin
Genkwanin.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 284.27 g/mol
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] and the leaves of the ferns Notholaena bryopoda and Asplenium normale [2] and 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 comprising the genus Alnus in the birch family Betulaceae. The genus comprises 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

A fern is a member of a group of vascular plants that reproduce via spores and have neither seeds nor flowers. The polypodiophytes include all living pteridophytes except the lycopods, and differ from mosses and other bryophytes 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 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. It is easily distinguished by its small cones, speckled bark and broad leaves.

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

Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance.

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

Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid found in a wide variety of plants, including citrus.

<i>Etlingera elatior</i> Herbaceous perennial plant

Etlingera elatior is a species of herbaceous perennial plant in the family Zingiberaceae; it is native to Thailand, Malesia and New Guinea.

<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.

<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 is a species of plant in the family Thymelaeaceae. It is It is threatened by habitat loss. This medicinal plant is a source of fragrant wood, formed under a pathological condition, called Chen Xiang in Standard Mandarin, or chàhm hēung in Cantonese, or agarwood.

NVC community W7 is one of the woodland communities in the British National Vegetation Classification system; it is one of seven woodland communities in the NVC classed as "wet woodlands".

<span class="mw-page-title-main">Anthocyanin</span> Class of chemical compounds

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 gave the name Anthokyan to a chemical compound that gives flowers a blue color for the first time 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.

<i>Agelastica alni</i> Species of beetle

Agelastica alni, the alder leaf beetle, is a species of leaf beetle (Chrysomelidae) in the genus Agelastica. Agelastica alni is distributed in Europe, the Caucasus, Siberia, north-eastern Kazakhstan, and in the 19th century was introduced to the United States.

<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), shows moderate aromatase inhibition, Betula pendula, and in the fern Asplenium normale.

<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.

<i>Eriophyes laevis</i> Species of mite

Eriophyes laevis is a gall mite which makes small, pimple-like galls on the leaves of alder. The mite was first described by the Austrian zoologist, Alfred Nalepa in 1889 and is found in Europe and North America.

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.
  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: 125–136. doi:10.1007/978-981-10-0833-7_8. ISBN   978-981-10-0832-0.