Irilone

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Irilone
Irilone.svg
Irilone-3D-balls.png
Names
IUPAC name
4′,9-Dihydroxy-6,7-[methylenebis(oxy)]isoflavone
Systematic IUPAC name
9-Hydroxy-7-(4-hydroxyphenyl)-2H,8H-[1,3]dioxolo[4,5-g][1]benzopyran-8-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2 X mark.svgN
    Key: NUGRQNBDTZWXTP-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2
    Key: NUGRQNBDTZWXTP-UHFFFAOYAV
  • C1OC2=C(O1)C(=C3C(=C2)OC=C(C3=O)C4=CC=C(C=C4)O)O
Properties
C16H10O6
Molar mass 298.24 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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Irilone is an isoflavone, a type of flavonoid. It can be found in Trifolium pratense (red clover), [1] in Iris unguicularis [2] and in Iris germanica . [3]

Related Research Articles

<i>Iris</i> (plant) Genus of flowering plants in the family Iridaceae

Iris is a flowering plant genus of 310 accepted species with showy flowers. As well as being the scientific name, iris is also widely used as a common name for all Iris species, as well as some belonging to other closely related genera. A common name for some species is flags, while the plants of the subgenus Scorpiris are widely known as junos, particularly in horticulture. It is a popular garden flower.

<span class="mw-page-title-main">Phytoestrogen</span> Plant-derived xenoestrogen

A phytoestrogen is a plant-derived xenoestrogen not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds that, because of its structural similarity with estradiol (17-β-estradiol), have the ability to cause estrogenic or antiestrogenic effects. Phytoestrogens are not essential nutrients because their absence from the diet does not cause a disease, nor are they known to participate in any normal biological function. Common foods containing phytoestrogens are soy protein, beans, oats, barley, rice, coffee, apples, carrots.

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).

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

Iris croatica is a bearded rhizomatous species of iris endemic to Croatia.

<i>Iris <span style="font-style:normal;">×</span> germanica</i> Species of plant

Iris × germanica is the accepted name for a species of flowering plants in the family Iridaceae commonly known as the bearded iris or the German bearded iris. It is one of a group of hybrid origin. Varieties include I. × g. var. florentina.

<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">Formononetin</span> Chemical compound

Formononetin is an O-methylated isoflavone.

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

Tectorigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from leopard lily, in Iris unguicularis or Pueraria thunbergiana.

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

Pratensein is an O-methylated isoflavone, a type of flavonoid. It can be found in Trifolium pratense and can have effects for the prevention of atherosclerosis.

<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">Pseudobaptigenin</span> Chemical compound

Pseudobaptigenin is an isoflavone, a type of flavonoid. It can be isolated in Trifolium pratense.

<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.

<i>Iris tenuifolia</i> Species of plant

Iris tenuifolia 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 a wide region over central Asia, including Afghanistan, Pakistan, ; Kazakhstan, Uzbekistan and Mongolia and in China. It has long greyish-green leaves, short stem and pale violet, lilac, pale blue, or purple flowers.

<i>Iris kemaonensis</i> Species of plant

Iris kemaonensis, the Kumaon iris, is a plant species in the genus Iris, it is also in the subgenus Iris and in the section Pseudoregelia. It is a rhizomatous perennial, from Tibetan China, Bhutan, India, Kashmir and Nepal. It has light green or yellowish green leaves, that extend after flowering time. It has a short stem, 1–2 fragrant flowers that are purple, lilac, lilac-purple or pale purple. They also have darker coloured blotches or spots. It is cultivated as an ornamental plant in temperate regions. It is often known as Iris kumaonensis, due to a publishing error.

Iris cypriana is a plant species in the genus Iris, it is also in the subgenus Iris. It is a rhizomatous perennial, from Cyprus. It has narrow, glaucous and evergreen leaves, tall slender stem, with 2–3 branches, and 1–3 large flowers in lavender, lilac, red-lilac, to dark purple shades. It is cultivated as an ornamental plant in temperate regions. It is listed in some sources as a synonym of Iris germanica.

<i>Iris florentina</i> Variety of plant

The identity of the plant first described by Carl Linnaeus as Iris florentina remains unclear, as of December 2021. In horticulture, it has been treated as a white-flowered variant of Iris × germanica, under names such as Iris germanica nothovar. florentina, Iris × germanica var. florentina and Iris × germanica 'Florentina'. Iris florentina has also been treated as the correct name for the true species also known as Iris albicansLange.

<i>Iris kashmiriana</i> Species of plant

Iris kashmiriana is a plant species in the genus Iris, it is also in the subgenus Iris. It is a rhizomatous perennial, from Kashmir, India. It has straight, sword-shaped, glaucous leaves, tall, thick stem with up 2 short branches, which hold 2–3 flowers, which can be white, cream or pale blue, lilac, lavender or blue-purple. It is cultivated as an ornamental plant in temperate regions, although in Kashmir, it is also planted on graves.

<i>Iris mesopotamica</i> Species of plant

Iris mesopotamica, the Mesopotamian iris, is a species in the genus Iris, it is also in the subgenus Iris. It is a rhizomatous perennial, from the middle East, within the countries of Iraq, Turkey, Syria and Israel. It has linear, grey-green or green broad leaves, tall stem with 2–3 branches, holding up to 9 scented flowers, in shades of violet, purple, lavender blue and light blue, with a yellow and white or orange and white beard. It is listed as a synonym of Iris germanica in some sources. It is cultivated as an ornamental plant in temperate regions, including being planted in graveyards and cemeteries but may also be used for celebrations and decoration.

<i>Iris sambucina</i> Species of plant

Iris sambucina, the elder scented iris, is a plant species in the genus Iris, it is also in the subgenus Iris. It is a rhizomatous perennial, from southern and central Europe, and Spain. It has green, curved or sword-like leaves, tall round stem, multiple flowers in shades from brown violet, or brown-purple, to purple-violet, blue violet, mauve, and to purple. The large flowers are fragrant, with the scent of elderflowers, hence the name. It was first considered a separate species, then it was classified as a synonym of Iris germanica, before being classified as a separate species again, but with a hybrid origin from Iris pallida and Iris variegata. It is sometimes cultivated as an ornamental plant in temperate regions.

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

Rimostil is a dietary supplement and extract of isoflavones from red clover which was under development by Kazia Therapeutics for the prevention of postmenopausal osteoporosis and cardiovascular disease and for the treatment of menopausal symptoms and hyperlipidemia but was never approved for medical use. It is enriched with isoflavone phytoestrogens such as formononetin, biochanin A, daidzein, and genistein, and is proposed to act as a selective estrogen receptor modulator, with both estrogenic and antiestrogenic effects in different tissues. The extract reached phase II clinical trials for cardiovascular disorders, hyperlipidemia, and postmenopausal osteoporosis prior to the discontinuation of its development in 2007.

References

  1. The red clover isoflavone irilone is largely resistant to degradation by the human gut microbiota. Annett Braune, Ronald Maul, Nils Helge Schebb, Sabine E. Kulling and Michael Blaut, Molecular Nutrition & Food Research, 8 Dec 2009
  2. New and Known Constituents from Iris unguicularis and Their Antioxidant Activity. Atta-ur-Rahman, Sumaira Hareem, M. Iqbal Choudhary, Bilge Sener, Ahmed Abbaskhan, Hina Siddiqui, Shazia Anjum, Ilkay Orhan, Ilhan Gurbuz and Filiz Ayanoglu, HeteroCycles, 2010, Special issue, Vol 82, No. 1, pages 813–824, doi : 10.3987/COM-10-S(E)6
  3. Lipase-catalyzed regioselective protection/deprotection of hydroxyl groups of the isoflavone irilone isolated from Iris germanica. Nighat Nazir, Surrinder Koul, Mushtaq Ahmad Qurishi, Subhash Chandra Taneja and Ghulam Nabi Qazi, Biocatalysis and Biotransformation, 2 December 2008, 1029–2446, Volume 27, Issue 2, Pages 118–123, INIST : 21235726