Valoneic acid dilactone

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Valoneic acid dilactone
Valoneic acid dilactone.svg
Names
Preferred IUPAC name
3,4,5-Trihydroxy-2-[(3,7,8-trihydroxy-5,10-dioxo-5,10-dihydro[1]benzopyrano[5,4,3-cde][1]benzopyran-2-yl)oxy]benzoate
Other names
Valoneic acid bislactone
Valoneic acid bilactone
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29) X mark.svgN
    Key: BPAOAXAAABIQKR-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29)
    Key: BPAOAXAAABIQKR-UHFFFAOYAM
  • Oc1cc5c(=O)oc3c(O)c(Oc4c(C(=O)O)cc(O)c(O)c4O)cc2c3c5c(c1O)oc2=O
Properties
C21H10O13
Molar mass 470.28 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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Valoneic acid dilactone is a hydrolysable tannin that can be isolated from the heartwood of Shorea laevifolia [1] and in oaks species like the North American white oak ( Quercus alba ) and European red oak ( Quercus robur ). [2]

It shows an inhibitory effect on 5α-reductase, [1] an enzyme involved in steroids metabolism and prostate cancer.

Related Research Articles

<span class="mw-page-title-main">Tannin</span> Class of astringent, bitter plant polyphenolic chemical compounds

Tannins are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids.

<i>Quercus alba</i> Species of oak tree

Quercus alba, the white oak, is one of the preeminent hardwoods of eastern and central North America. It is a long-lived oak, native to eastern and central North America and found from Minnesota, Ontario, Quebec, and southern Maine south as far as northern Florida and eastern Texas. Specimens have been documented to be over 450 years old.

<i>Quercus robur</i> Species of flowering plant in the beech and oak family Fagaceae

Quercus robur, commonly known as common oak, pedunculate oak, European oak or English oak, is a species of flowering plant in the beech and oak family, Fagaceae. It is native to most of Europe west of the Caucasus. The tree is widely cultivated in temperate regions and has escaped into the wild in scattered parts of China and North America.

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

Tannic acid is a specific form of tannin, a type of polyphenol. Its weak acidity (pKa around 6) is due to the numerous phenol groups in the structure. The chemical formula for commercial tannic acid is often given as C76H52O46, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of galloyl moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (Caesalpinia spinosa), gallnuts from Rhus semialata or Quercus infectoria or Sicilian sumac leaves (Rhus coriaria).

<span class="mw-page-title-main">Ellagic acid</span> Natural phenol antioxidant

Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.

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

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

Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

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

Procyanidins are members of the proanthocyanidin class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.

A hydrolyzable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.

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

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak and European red oak. It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

Trigalloyl glucose may refer to:

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

Glucogallin is chemical compound formed from gallic acid and β-D-glucose. It can be found in oaks species like the North American white oak, European red oak and Amla fruit.

<i>Quercus infectoria</i> Species of oak tree

Quercus infectoria or the Aleppo oak is a species of oak well known for producing galls that have been traditionally used for centuries in Asia medicinally while also used in softening leather and in making black dye and ink.

<i>Quercus salicina</i> Species of oak tree

Quercus salicina is an oak species found in Japan, South Korea and Taiwan.

Tergallic acids are trimers of gallic acid, often found naturally in the form of glycosides. Tergallic acid O- or C-glucosides that can be found in acorns of several Quercus (oak) species. The dehydrated tergallic acid C-glucoside and tergallic acid O-glucoside can be characterised in the acorns of Quercus macrocarpa. Dehydrated tergallic-C-glucoside can be found in the cork from Quercus suber.

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

Valoneic acid is a hydrolysable tannin. It is a component of some hydrolysable tannins such as mallojaponin.

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

Flavogallonic acid is a hydrolysable tannin that can be found in valonea oak in chestnut wood or in Terminalia myriocarpa.

<span class="mw-page-title-main">Flavogallonic acid dilactone</span> Chemical compound

Flavogallonic acid dilactone is a hydrolysable tannin that can be found in Rhynchosia volubilis seeds, in Shorea laevifolia, in Anogeissus leiocarpus and Terminalia avicennoides.

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

Oligostilbenoids are oligomeric forms of stilbenoids. Some molecules are large enough to be considered polyphenols and constitute a class of tannins.

References

  1. 1 2 5A-Reductase inhibitory tannin-related compounds isolated from Shorea laevifolia. Yoshio Hirano, Ryuichiro Kondo and Kokki Sakai, Journal of wood science, Volume 49, Number 4, pp.339-343, doi : 10.1007/s10086-002-0481-y
  2. Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry. Pirjo Mämmelä, Heikki Savolainenb, Lasse Lindroosa, Juhani Kangasd and Terttu Vartiainen, Journal of Chromatography A, Volume 891, Issue 1, 1 September 2000, Pages 75-83, doi : 10.1016/S0021-9673(00)00624-5