Retusin (isoflavone)

Last updated
Retusin
Retusin isoflavone.svg
Retusin-(isoflavone)-3D-balls.png
Names
IUPAC name
7,8-Dihydroxy-4′-methoxyisoflavone
Systematic IUPAC name
7,8-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C16H12O5/c1-20-10-4-2-9(3-5-10)12-8-21-16-11(14(12)18)6-7-13(17)15(16)19/h2-8,17,19H,1H3 X mark.svgN
    Key: DLXIJJURUIXRFK-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H12O5/c1-20-10-4-2-9(3-5-10)12-8-21-16-11(14(12)18)6-7-13(17)15(16)19/h2-8,17,19H,1H3
    Key: DLXIJJURUIXRFK-UHFFFAOYAG
  • COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3O)O
Properties
C16H12O5
Molar mass 284.26 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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Retusin is an O-methylated isoflavone, a type of flavonoid. It can be found in Fabaceae species like Dipteryx odorata , [1] [2] in Dalbergia retusa [3] and in Millettia nitida . [4] It can also be found in Maackia amurensis cell cultures. [5]

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

Polyphenols are a large family of naturally occurring phenols They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

<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.

<i>Dipteryx odorata</i> Species of flowering tree in the pea family

Dipteryx odorata is a species of flowering tree in the pea family, Fabaceae. The tree is native to Northern South America and is semi-deciduous. Its seeds are known as tonka beans. They are black and wrinkled and have a smooth, brown interior. They have a strong fragrance similar to sweet woodruff due to their high content of coumarin.

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

Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose.

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

Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.

<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">Honokiol</span> Chemical compound

Honokiol is a lignan isolated from the bark, seed cones, and leaves of trees belonging to the genus Magnolia. It has been identified as one of the chemical compounds in some traditional eastern herbal medicines along with magnolol, 4-O-methylhonokiol, and obovatol.

<i>Maackia amurensis</i> Species of legume

Maackia amurensis, commonly known as the Amur maackia, is a species of tree in the family Fabaceae that can grow 15 metres (49 ft) tall. The species epithet and common names are from the Amur River region, where the tree originated; it occurs in northeastern China, Korea, and Russia.

<i>Dipteryx alata</i> Species of legume

Dipteryx alata is a large, undomesticated, edible nut-bearing tree from dryish tropical lowlands in central South America belonging to the legume family, Fabaceae, from the Dipterygeae tribe in the Faboideae subfamily. It is a wild species, widespread across the Cerrado savanna in South America. The baru nut seed is a grain legume, growing in popularity in North America as a snack food.

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

Formononetin is an O-methylated isoflavone.

<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">Alpinumisoflavone</span> Chemical compound

Alpinumisoflavone is a pyranoisoflavone, a type of isoflavone. It can be found in the bark of Rinorea welwitschii. It can also be found in the molluscicide plant Millettia thonningii and is thought to be an antischistosomal agent since it has been shown to kill the snails which transmit the schistosomiasis and also the larvae of the parasite itself.

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

Millettia thonningii is a species in the genus Millettia. It is a molluscicide plant. It contains the isoflavone alpinumisoflavone that is thought to be an antischistosomal agent.

<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">Medicarpin</span> Chemical compound

Medicarpin is a pterocarpan, a derivative of isoflavonoids.

<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.

Amurensin may refer to:

<i>Dalbergia lanceolaria</i> Species of legume

Dalbergia lanceolaria is a species of tree in the subfamily Faboideae and tribe Dalbergieae. It is a medium-sized tree growing to 20m tall and is native to: India, Sri Lanka, Nepal, Burma and Indo-China.

<i>Callerya nitida</i> Species of plant

Callerya nitida is a species of flowering plant in the family Fabaceae, native to south-central and southeast mainland China, Hainan and Taiwan. It was first described by George Bentham in 1842 as Millettia nitida.

References

  1. Isoflavones from Dipteryx odorata. Teruo Hayashi and Ronald H. Thomson, Phytochemistry, Volume 13, Issue 9, September 1974, Pages 1943-1946
  2. Microsomal metabolism of calycosin, formononetin and drug–drug interactions by dynamic microdialysis sampling and HPLC–DAD–MS analysis. Xiao-Dong Wen, Lian-Wen Qi, Bin Lia, Ping Li, Ling Yia, Ya-Qiong Wang, E-Hu Liu and Xiao-Lin Yang, Journal of Pharmaceutical and Biomedical Analysis, Volume 50, Issue 1, 15 August 2009, Pages 100-105
  3. Retusin (Dalbergia) on kanaya.naist.jp/
  4. Interactions between thrombin and natural products of Millettia nitita var. hirsutissima using capillary zone electrophoresis. Shuyu Zhang, Jun Cheng, Wenjing Chen, Xiaomei Ling, Yuying Zhao, Jie Feng, Cheng Xiang and Hong Liang, Journal of Chromatography B, Volume 877, Issue 32, 15 December 2009, pages 4107-4114, doi : 10.1016/j.jchromb.2009.10.033
  5. Isoflavonoid production by callus cultures of Maackia amurensis. S.A Fedoreyev, T.V Pokushalov, M.V Veselova, L.I Glebko, N.I Kulesh, T.I Muzarok, L.D Seletskaya, V.P Bulgakov and Yu.N Zhuravlev, Fitoterapia, 1 August 2000, Volume 71, Issue 4, Pages 365–372, doi : 10.1016/S0367-326X(00)00129-5