Tectorigenin

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Tectorigenin
Tectorigenin.svg
Tectorigenin-3D-balls.png
Names
IUPAC name
4′,5,7-Trihydroxy-6-methoxyisoflavone
Systematic IUPAC name
5,7-Dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
Other names
Tectorigenine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.208.621 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12O6/c1-21-16-11(18)6-12-13(15(16)20)14(19)10(7-22-12)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3 X mark.svgN
    Key: OBBCRPUNCUPUOS-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H12O6/c1-21-16-11(18)6-12-13(15(16)20)14(19)10(7-22-12)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3
    Key: OBBCRPUNCUPUOS-UHFFFAOYAZ
  • COC1=C(C=C2C(=C1O)C(=O)C(=CO2)C3=CC=C(C=C3)O)O
Properties
C16H12O6
Molar mass 300.266 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tectorigenin is an O-methylated isoflavone, a type of flavonoid. It ha been isolated from leopard lily (Belamcanda chinensis), [1] Algerian iris (Iris unguicularis) [2] and East Asian arrowroot (Pueraria thunbergiana). [3]

Contents

Glycosides

Tectoridin is the 7-glucoside of tectorigenin.

See also

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">Kaempferol</span> Chemical compound

Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach, and broccoli. Kaempferol is a yellow crystalline solid with a melting point of 276–278 °C (529–532 °F). It is slightly soluble in water and highly soluble in hot ethanol, ethers, and DMSO. Kaempferol is named for 17th-century German naturalist Engelbert Kaempfer.

<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.

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

A leopard pattern is a spotted color pattern, particularly in the hair coat or skin of animals, but can also describe spotting patterns in plants and a distinctive print appearing on clothing and other fabrics.

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

Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant kudzu and from soybean leaves.

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

Puerarin, one of several known isoflavones, is found in a number of plants and herbs, such as the root of the kudzu plant

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

Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily, and Iris kemaonensis.

ψ-Tectorigenin Chemical compound

ψ-Tectorigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from Belamcanda chinensis, Dalbergia sissoo. It can also be isolated from the bacterium Nocardiopsis sp, and from the mold Stemphilium sp. No. 644.

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

Iridin is an isoflavone, a type of flavonoid. It is the 7-glucoside of irigenin and can be isolated from several species of irises like orris root, Iris florentina or Iris versicolor, also commonly known as the larger blue flag. It can also be found in Iris kemaonensis.

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

Tectoridin is an isoflavone, a type of flavonoid. It is the 7-glucoside of tectorigenin and can be isolated from flowers of Pueraria thunbergiana (Leguminosae).

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

<i>Iris domestica</i> Species of flowering plant

Iris domestica, commonly known as leopard lily, blackberry lily, and leopard flower, is an ornamental plant in the family Iridaceae. In 2005, based on molecular DNA sequence evidence, Belamcanda chinensis, the sole species in the genus Belamcanda, was transferred to the genus Iris and renamed Iris domestica.

<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">Irilone</span> Chemical compound

Irilone is an isoflavone, a type of flavonoid. It can be found in Trifolium pratense, in Iris unguicularis and in Iris germanica.

<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.

<i>Iris tectorum</i> Species of flowering plant

Iris tectorum is a plant species in the genus Iris, it is also in the subgenus Limniris. It is a rhizomatous perennial. It is native of China, Korea and Burma, with lavender-blue, bluish-violet, purple-blue, blue-lilac or sky blue flowers. There is a white form as well. It is a compact plant and is cultivated as an ornamental plant in temperate regions of the world.

<i>Iris unguicularis</i> Species of flowering plant

Iris unguicularis, the Algerian iris, is a rhizomatous flowering plant in the genus Iris, native to Greece, Turkey, Western Syria, and Tunisia. It grows to 30 centimetres (12 in), with grassy evergreen leaves, producing pale lilac or purple flowers with a central band of yellow on the falls. The flowers appear in winter and early spring. They are fragrant, with pronounced perianth tubes up to 20 cm (7.9 in) long.

Iris bungei is a beardless iris in the genus Iris, in the subgenus Limniris and in the series Tenuifoliae of the genus. It is a rhizomatous herbaceous perennial, from Mongolia, Tibet and China. It has green leaves, short stem and 2 violet, purple, lavender or blue flowers.

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

Mirificin, also known as daidzein 8-C-(6-apiofuranosylglucoside), is an isoflavone that is found in Pueraria mirifica and Pueraria lobata. It has estrogenic activity and hence is a phytoestrogen.

References

  1. Thelen, Paul; Scharf, Jens-Gerd; Burfeind, Peter; Hemmerlein, Bernhard; Wuttke, Wolfgang; Spengler, Barbara; Christoffel, Volker; Ringert, Rolf-Hermann; Seidlová-Wuttke, Dana (2005). "Tectorigenin and other phytochemicals extracted from leopard lily Belamcanda chinensis affect new and established targets for therapies in prostate cancer". Carcinogenesis. 26 (8): 1360–1367. doi: 10.1093/carcin/bgi092 . PMID   15845653.
  2. Atta-Ur-Rahman; Hareem, Sumaira; Iqbal Choudhary, M.; Sener, Bilge; Abbaskhan, Ahmed; Siddiqui, Hina; Anjum, Shazia; Orhan, Ilkay; Gurbuz, Ilhan; Ayanoglu, Filiz (2010). "New and Known Constituents from Iris unguicularis and Their Antioxidant Activity". Heterocycles. 82: 813. doi:10.3987/COM-10-S(E)6.
  3. Lee, Kyung-Tae; Sohn, Il-Cheol; Kim, Young-Kwan; Choi, Jung-Hye; Choi, Jong-Won; Park, Hee-Juhn; Itoh, Yoshie; Miyamoto, Ken-Ichi (2001). "Tectorigenin, an Isoflavone of Pueraria thunbergiana BENTH., Induces Differentiation and Apoptosis in Human Promyelocytic Leukemia HL-60 Cells". Biological and Pharmaceutical Bulletin. 24 (10): 1117–1121. doi: 10.1248/bpb.24.1117 . PMID   11642314.