7-O-Methylluteone

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7-O-Methylluteone
7-O-Methylluteone.png
Names
IUPAC name
2′,4′,5-Trihydroxy-7-methoxy-6-(3-methylbut-2-en-1-yl)isoflavone
Systematic IUPAC name
3-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-6-(3-methylbut-2-en-1-yl)-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C21H20O6/c1-11(2)4-6-14-17(26-3)9-18-19(20(14)24)21(25)15(10-27-18)13-7-5-12(22)8-16(13)23/h4-5,7-10,22-24H,6H2,1-3H3
    Key: AZPLXDBZIQMMMT-UHFFFAOYSA-N
  • InChI=1/C21H20O6/c1-11(2)4-6-14-17(26-3)9-18-19(20(14)24)21(25)15(10-27-18)13-7-5-12(22)8-16(13)23/h4-5,7-10,22-24H,6H2,1-3H3
    Key: AZPLXDBZIQMMMT-UHFFFAOYAB
  • CC(=CCC1=C(C=C2C(=C1O)C(=O)C(=CO2)C3=C(C=C(C=C3)O)O)OC)C
Properties
C21H20O6
Molar mass 368.385 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

7-O-Methylluteone is a prenylated isoflavone. It can be found in the bark of Erythrina burttii . [1]

The enzyme monoprenyl isoflavone epoxidase uses 7-O-methylluteone, NADPH, H+ and O2 to produce a dihydrofurano pyranoisoflavone derivative, NADP+ and H2O.

Related Research Articles

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae).

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

Daidzein is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their poor bioavailability and low water solubility.

<i>Erythrina variegata</i> Species of legume

Erythrina variegata, commonly known as tiger's claw or Indian coral tree, is a species of Erythrina native to the tropical and subtropical regions of eastern Africa, the Indian subcontinent, northern Australia, and the islands of the Indian Ocean and the western Pacific Ocean east to Fiji.

In enzymology, a monoprenyl isoflavone epoxidase (EC 1.14.99.34) is an enzyme that catalyzes the chemical reaction

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

Erythravine is a tetrahydroisoquinoline alkaloid found in the plant Erythrina mulungu and other species of the genus Erythrina.

The molecular formula C21H20O6 may refer to:

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

Biochanin A is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A can be found in red clover in soy, in alfalfa sprouts, in peanuts, in chickpea and in other legumes.

<span class="mw-page-title-main">Prenylflavonoid</span>

Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid.

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

Prunetin is an O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of Prunus emarginata. Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores. It is also an allosteric inhibitor of human liver aldehyde dehydrogenase.

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

Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense L..

<span class="mw-page-title-main">Luteone (isoflavone)</span> Chemical compound

Luteone is a prenylated isoflavone, a type of flavonoid. It can be found in the pods of Laburnum anagyroides and can be synthesized.

Luteone may refer to:

<i>Millettia pachycarpa</i> Species of legume

Millettia pachycarpa is a perennial climbing shrub belonging to the genus Millettia. It is one of the most well known among ~150 species of Millettia, as it is widely used in traditional practices, such as for poisoning fish, agricultural pesticide, blood tonic, and treatments of cancer and infertility. The bark fiber is used for making strong ropes.

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

Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone". Members of the genus Millettia are now known to be rich in barbigerone, including M. dielsiena, M. ferruginea, M. usaramensis, and M. pachycarpa. It has also been isolated from the medicinal plant Sarcolobus globosus. Barbigerone from S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.

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

Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes which can be formed by coupling of the B ring to the 4-one position.

The molecular formula C20H18O4 may refer to:

Erythrina orientalis is a plant species in the genus Erythrina. This plant is a climbing herb that grows up to 6 m long, and has compound leaves with petioles that are 5–6 cm long. Its leaflets emerge in groups of three, and are 7–9 cm long and 5–8 cm wide. The plant's young leaves, flowers and pods are consumed as vegetables.

The biosynthesis of isoflavonoids involves several enzymes; These are:

<i>Erythrina burttii</i> Species of legume

Erythrina burttii is a flowering plant species in the genus of Erythrina found in Kenya and Ethiopia.

<i>Erythrina berteroana</i> Species of legume

Erythrina berteroana is a species of small deciduous tree in the family Fabaceae. It is found in Mexico, Central America and the northern part of South America. Common names include elequeme, gallito, machete, pernila de casa, pito and poró de cerca. It is a common tree in the drier parts of its range and has many traditional uses.

References

  1. Two prenylated flavonoids from the stem bark of Erythrina burttii. Abiy Yenesew, Beatrice Irungu, Solomon Derese, Jacob O. Midiwo, Matthias Heydenreich and Martin G. Peter, Phytochemistry, Volume 63, Issue 4, June 2003, Pages 445–448, doi : 10.1016/S0031-9422(03)00209-7