Isoorientin

Last updated
Isoorientin
Homoorientin.svg
Names
IUPAC name
6-(β-D-Glucopyranosyl)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-1-benzopyran-4-one
Other names
Luteolin-6-C-glucoside
homoorientin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.128.382 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1
    Key: ODBRNZZJSYPIDI-VJXVFPJBSA-N
  • C1=CC(=C(C=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O)C4C(C(C(C(O4)CO)O)O)O)O)O)O
Properties
C21H20O11
Molar mass 448.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isoorientin (or homoorientin) is a flavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside. Bioassay-directed fractionation techniques led to isolation of isoorientin as the main hypoglycaemic component in Gentiana olivieri . [1] Studies also showed that isoorientin is a potential neuroprotective compound against Alzheimer's disease. [2]

Contents

Natural occurrences

Isoorientin can be isolated from the passion flower, Vitex negundo , Terminalia myriocarpa , the Açaí palm and Swertia japonica .

Metabolism

See also

Related Research Articles

<i>Gentiana</i> Genus of flowering plants in the family Gentianaceae

Gentiana is a genus of flowering plants belonging to the gentian family (Gentianaceae), the tribe Gentianeae, and the monophyletic subtribe Gentianinae. With about 400 species, it is considered a large genus. Gentians are notable for their mostly large trumpet-shaped flowers, which are often of an intense blue hue.

A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.

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

Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance.

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

Marine pharmacognosy is the investigation and identification of medically important plants and animals in the marine environment. It is a sub branch of terrestrial pharmacognosy. Generally the drugs are obtained from the marine species of bacteria, virus, algae, fungi and sponges. It is a relatively new field of study in western medicine, although many marine organisms were used in Traditional Chinese Medicine. It was not until 2004 that the first FDA approval of a drug came directly from the sea: ziconotide, which was isolated from a marine cone snail.

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

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

<span class="mw-page-title-main">Phenolic content in wine</span> 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.

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

Orientin is a flavone, a chemical flavonoid-like compound. It is the 8-C glucoside of luteolin.

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

Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus, in the Phyllostachys nigra bamboo leaves, in the pearl millet, and in Hawthorn.

The molecular formula C21H20O10 (molar mass: 432.38 g/mol, exact mass: 432.105647 u) may refer to:

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

Isovitexin is a flavone. the apigenin-6-C-glucoside. In this case, the prefix 'iso' does not imply an isoflavonoid, but the position of the glucoside on the flavone.

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

Isoquercetin, isoquercitrin or isotrifoliin is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including Mangifera indica (mango) and Rheum nobile. It is also present in the leaves of Annona squamosa, Camellia sinensis (tea). and Vestia foetida

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

Cynaroside is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin.

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

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin.

The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes or during controlled oxygenation processes during the aging of wine. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins, oxovitisins and pyranoanthocyanin dimers; their general structure includes an additional ring that may have different substituents linked directly at C-10.

Charantin is a chemical substance obtained from the Asian bitter melon, reputed to be responsible for the hypoglycaemic properties of those plants. It was identified by Lolitkar and Rao in 1960. It was also found in the similar African species M. foetida, by A. Olaniyi in 1975, under the name foetidin.

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.

<i>Gentiana olivieri</i> Species of plant

Gentiana olivieri is a plant species in the genus Gentiana found in Asia.

<i>Phlomoides tuberosa</i> Species of flowering plant

Phlomoides tuberosa, the sage-leaf mullein, is a perennial herbaceous flowering plant in the family Lamiaceae, native to China, Kazakhstan, Kyrgyzstan, Mongolia, Russia; SW Asia and Europe. Enlarged, tuberous roots give rise to erect stems to 150 cm bearing purple-red flowers.

<span class="mw-page-title-main">Bioassay</span> Analytical method to determine concentration of a substance

A bioassay is an analytical method to determine the concentration or potency of a substance by its effect on living animals or plants, or on living cells or tissues(in vitro). A bioassay can be either quantal or quantitative, direct or indirect. If the measured response is binary, the assay is quantal, if not, it is quantitative.

Silene jenisseensis, is a species of flowering plant in the family Caryophyllaceae, native to Siberia, Far East and Mongolia.

References

  1. Hypoglycaemic activity of Gentiana olivieri and isolation of the active constituent through bioassay- directed fractionation techniques. Ekrem Sezik, Mustafa Aslan, Erdem Yesilada, Shigeru Ito, Life Sciences, 28 January 2005, Volume 76, Issue 11, Pages 1223–1238, doi : 10.1016/j.lfs.2004.07.024
  2. Zhibin Liang; Bei Zhang; Wei Wen Su; Philip G Williams; Qing X Li (July 2016). "C-Glycosylflavones Alleviate Tau Phosphorylation and Amyloid Neurotoxicity through GSK3β Inhibition". ACS Chemical Neuroscience. 7: 912–923. doi:10.1021/acschemneuro.6b00059. PMC   7355085 . PMID   27213824.