Fisetinidin

Last updated
Fisetinidin chloride
Fisetinidin.svg
Names
IUPAC name
2-(3,4-dihydroxyphenyl)chromenylium-3,7-diol chloride
Other names
Fisetinidin chloride
3,3',4',7-Tetrahydroxyflavylium chloride
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C15H10O5.ClH/c16-10-3-1-8-5-13(19)15(20-14(8)7-10)9-2-4-11(17)12(18)6-9;/h1-7H,(H3-,16,17,18,19);1H X mark.svgN
    Key: GLSBVYMMIPVYDC-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C15H10O5.ClH/c16-10-3-1-8-5-13(19)15(20-14(8)7-10)9-2-4-11(17)12(18)6-9;/h1-7H,(H3-,16,17,18,19);1H
    Key: GLSBVYMMIPVYDC-UHFFFAOYAZ
  • C1=CC(=CC2=[O+]C(=C(C=C21)O)C3=CC(=C(C=C3)O)O)O.[Cl-]
Properties
C15H11O5+ (Cl)
Molar mass 306.69 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Fisetinidin is an anthocyanidin. It has been obtained from the heartwood of Acacia mearnsii , [1] from the bark of Rhizophora apiculata [2] and can also be synthesized. [3] Fisetinidin is very similar in structure to fisetin, [3] which itself differs in structure from quercetin only by an additional hydroxyl group on the latter.

Contents

An assay of twenty flavonoids showed fisetinidin to be the least effective in inhibition of CD38 enzyme. [4]

Tannins

Fisetinidin can compose tannins. [1] The polymers are then called profisetinidin (Porter, 1992). [2]

See also

Related Research Articles

Tannin 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.

Flavan-3-ol Category of chemical compound

Flavan-3-ols are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They are found in most plants and have a role in plant defense.

Polyphenol Class of chemical compounds

Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. 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.

<i>Schinopsis balansae</i> Species of tree

Schinopsis balansae is a hardwood tree known as willow-leaf red quebracho which forms forests in the subtropical Humid Chaco ecoregion of north-eastern Argentina, and Paraguay. It is also found in the wild Pantanal vegetation in Brazil. Some of its vernacular names are quebracho colorado chaqueño and quebracho santafesino. Other species, like Schinopsis lorentzii, bear the general name quebracho and have similar properties and uses. S. balansae shares its habitat with a species of the same genus, S. heterophylla, and the two are often confused.

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.

<i>Acacia mearnsii</i> Species of flowering plant

Acacia mearnsii, commonly known as black wattle, late black wattle or green wattle, is a species of flowering plant in the family Fabaceae and is endemic to south-eastern Australia. It is usually an erect tree with smooth bark, bipinnate leaves and spherical heads of fragrant pale yellow or cream-coloured flowers followed by black to reddish brown pods. In some other parts of the world, it is regarded as an invasive species.

Procyanidin

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.

<i>Rhizophora apiculata</i> Species of tree

Rhizophora apiculata belongs to the Plantae kingdom under the Rhizophoraceae family. Currently R. apiculata is distributed throughout Australia, Guam, India, Indonesia, Malaysia, Micronesia, New Caledonia, Papua New Guinea, the Philippines, Singapore, the Solomon Islands, Sri Lanka, Taiwan, the Maldives, Thailand, Vanuatu, and Vietnam. Rhizophora apiculata is called ‘bakhaw lalaki,’ in the Philippines, "Thakafathi ތަކަފަތި" in the Maldives, 'Đước' in Vietnam, Garjan in India, as well as other vernacular names.

Phenolic content in wine Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

Fisetin Chemical compound

Fisetin (7,3′,4′-flavon-3-ol) is a plant flavonol from the flavonoid group of polyphenols. It can be found in many plants, where it serves as a yellow/ochre colouring agent. It is also found in many fruits and vegetables, such as strawberries, apples, persimmons, onions and cucumbers. Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.

A profisetinidin is a type of condensed tannins formed from leuco-fisetinidin, the leucoanthocyanidin form of fisetinidin.

Prodelphinidin is a name for the polymeric tannins composed of gallocatechin. It yields delphinidin during depolymerisation under oxidative conditions.

Leucoanthocyanidin Chemical compound

Leucoanthocyanidin (flavan-3,4-diols) are colorless chemical compounds related to anthocyanidins and anthocyanins. Leucoanthocyanins can be found in Anadenanthera peregrina and in several species of Nepenthes including N. burbidgeae, N. muluensis, N. rajah, N. tentaculata, and N. × alisaputrana.

A type proanthocyanidins are a specific type of proanthocyanidins, which are a class of flavonoid. Proanthocyanidins fall under a wide range of names in the nutritional and scientific vernacular, including oligomeric proanthocyanidins, flavonoids, polyphenols, condensed tannins, and OPCs. Proanthocyanidins were first popularized by French scientist Jacques Masquelier.

Phlobaphene

Phlobaphenes are reddish, alcohol-soluble and water-insoluble phenolic substances. They can be extracted from plants, or be the result from treatment of tannin extracts with mineral acids. The name phlobaphen come from the Greek roots φλoιὀς (phloios) meaning bark and βαφή (baphe) meaning dye.

Prorobinetidins are a type of condensed tannins formed from robinetinidol. They form robinetinidin when depolymerized under oxidative conditions.

Castalagin Chemical compound

Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides.

Quebracho[keˈβ̞ɾa.t͡ʃo] is a common name in Spanish to describe very hard wood tree species. The etymology of the name derived from quiebrahacha, or quebrar hacha, meaning "axe-breaker".

Condensed tannin Polymers formed by the condensation of flavans.

Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.

Leucofisetinidin Chemical compound

Leucofisetinidin is a flavan-3,4-diol (leucoanthocyanidin), a type of natural phenolic substance. It is the monomer of condensed tannins called profisetinidins. Those tannins can be extracted from the heartwood of Acacia mearnsii or from the heartwoods of Schinopsis balansae, Schinopsis quebrachocolorado and from commercial quebracho extract.

References

  1. 1 2 D. G. Roux; E. Paulus (February 1962). "Condensed tannins. 12. Polymeric leuco-fisetinidin tannins from the heartwood of Acacia mearnsii". Biochem. J. 82 (2): 320–324. doi:10.1042/bj0820320. PMC   1243455 . PMID   14494576.
  2. 1 2 Afidah A. Rahim; Emmanuel Rocca; Jean Steinmetz; M. Jain Kassim; M. Sani Ibrahim; Hasnah Osman (2008). "Antioxidant activities of mangrove Rhizophora apiculata bark extracts". Food Chemistry. 107 (1): 200–207. doi:10.1016/j.foodchem.2007.08.005.
  3. 1 2 M. Gábor; E. EperJessy (10 December 1966). "Antibacterial Effect of Fisetin and Fisetinidin". Nature. 212 (1273): 1273. doi: 10.1038/2121273a0 . PMID   21090477. S2CID   4262402.
  4. Kellenberger E, Kuhn I, Schuber F, Muller-Steffner H (2011). "Flavonoids as inhibitors of human CD38". Bioorganic & Medicinal Chemistry Letters . 21 (13): 3939–3942. doi:10.1016/j.bmcl.2011.05.022. PMID   21641214.