Herbacetin

Last updated
Herbacetin
Herbacetin.svg
Herbacetin-3D-balls.png
Names
IUPAC name
3,4′,5,7,8-Pentahydroxyflavone
Systematic IUPAC name
3,5,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
8-Hydroxykaempferol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.237.124 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C15H10O7/c16-7-3-1-6(2-4-7)14-13(21)12(20)10-8(17)5-9(18)11(19)15(10)22-14/h1-5,16-19,21H X mark.svgN
    Key: ZDOTZEDNGNPOEW-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C15H10O7/c16-7-3-1-6(2-4-7)14-13(21)12(20)10-8(17)5-9(18)11(19)15(10)22-14/h1-5,16-19,21H
    Key: ZDOTZEDNGNPOEW-UHFFFAOYAP
  • C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O
Properties
C15H10O7
Molar mass 302.238 g·mol−1
Density 1.799 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Herbacetin is a flavonol, a type of flavonoid.

Glycosides

Herbacetin diglucoside can be isolated from flaxseed hulls. [1]

Contents

Rhodionin is a herbacetin rhamnoside found in Rhodiola species. [2]

Rhodiolin, a flavonolignan, is the product of the oxidative coupling of coniferyl alcohol with the 7,8-dihydroxy grouping of herbacetin. It can be found in the rhizome of Rhodiola rosea . [3]

Related Research Articles

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Nelumbo nucifera, also known as sacred lotus, Laxmi lotus, Indian lotus, or simply lotus, is one of two extant species of aquatic plant in the family Nelumbonaceae. It is sometimes colloquially called a water lily, though this more often refers to members of the family Nymphaeaceae.

<span class="mw-page-title-main">Secoisolariciresinol diglucoside</span> Antioxidant phytoestrogen

Secoisolariciresinol diglucoside (SDG) is an antioxidant phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed. It is a precursor of mammal lignans which are produced in the colon from chemicals in foods.

<i>Rhodiola rosea</i> Species of flowering plant in the stonecrop family Crassulaceae

Rhodiola rosea is a perennial flowering plant in the family Crassulaceae. It grows naturally in wild Arctic regions of Europe, Asia, and North America, and can be propagated as a groundcover.

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

Silibinin (INN), also known as silybin (both from Silybum, the generic name of the plant from which it is extracted), is the major active constituent of silymarin, a standardized extract of the milk thistle seeds, containing a mixture of flavonolignans consisting of silibinin, isosilibinin, silychristin, silidianin, and others. Silibinin itself is a mixture of two diastereomers, silybin A and silybin B, in approximately equimolar ratio. The mixture exhibits a number of pharmacological effects, particularly in the fatty liver, non-alcoholic fatty liver, non-alcoholic steatohepatitis, and there is great clinical evidence for the use of silibinin as a supportive element in alcoholic and Child–Pugh grade 'A' liver cirrhosis. However, despite its several beneficial effects on the liver, silibinin and all the other compounds found in silymarin, especially silychristin seem to act as potent disruptors of the thyroid system by blocking the MCT8 transporter. The long term intake of silymarin can lead to some form of thyroid disease and if taken during pregnancy, silymarin can cause the development of the Allan–Herndon–Dudley syndrome. Although this information is not being taken into consideration by all regulatory bodies, several studies now consider silymarin and especially silychristin to be important inhibitors of the MCT8 transporter and a potential disruptor of the thyroid hormone functions.

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<i>Pteridium aquilinum</i> Species of plant (fern)

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

Secoisolariciresinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, e.g. rye, and together with matairesinol, has attracted much attention for its beneficial nutritional effects.

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

Lotaustralin is a cyanogenic glucoside found in small amounts in Fabaceae austral trefoil, cassava, lima bean, roseroot and white clover, among other plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide.

<i>Rhodiola</i> Genus of flowering plants

Rhodiola is a genus of perennial plants in the family Crassulaceae that resemble Sedum and other members of the family. Like sedums, Rhodiola species are often called stonecrops. Some authors merge Rhodiola into Sedum.

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

Rosavin are a family of cinnamyl mono- and diglycosides that are key ingredients of Rhodiola rosea L.,. R. rosea is an important medicinal plant commonly used throughout Europe, Asia, and North America, that has been recognized as a botanical adaptogen by the European Medicines Agency. Rosavin production is specific to R. rosea and R. sachalinenis, and the biosynthesis of these glycosides occurs spontaneously in Rhodiola roots and rhizomes. The production of rosavins increases in plants as they get older, and the amount of the cinnamyl alcohol glycosides depends on the place of origin of the plant.

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

Salidroside (rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea. It has been studied, along with rosavin, as one of the potential compounds responsible for the putative antidepressant and anxiolytic actions of this plant. Salidroside may be more active than rosavin, even though many commercially marketed Rhodiola rosea extracts are standardized for rosavin content rather than salidroside.

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

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical compound that gives flowers a blue color for the first time in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

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

Icariin is a chemical compound classified as a prenylated flavonol glycoside, a type of flavonoid. It is the 8-prenyl derivative of kaempferol 3,7-O-diglucoside. The compound has been isolated from several species of plant belonging to the genus Epimedium which are commonly known as horny goat weed, Yin Yang Huo, and Herba epimedii. Extracts from these plants are reputed to produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function. However, clinical trial data are lacking to support these claims.

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

Galangin is a flavonol, a type of flavonoid.

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

Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols.

<i>Selliguea feei</i> Species of fern

Selliguea feei is a fern belonging to the genus Selliguea in the family Polypodiaceae. This fern can be collected in Indonesia. The species name feei commemorates the botanist Antoine Laurent Apollinaire Fée.

Flavonolignans are natural phenols composed of a part flavonoid and a part phenylpropane.

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

Rhodionin is a herbacetin rhamnoside found in Rhodiola species.

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

Rosiridin is a chemical compound that has been isolated from Rhodiola sachalinensis. Rosiridin can inhibit monoamine oxidases A and B, possibly meaning that the compound could help in the treatment of depression and senile dementia.

<span class="mw-page-title-main">Silychristin</span> Natural chemical compound

Silychristin is a natural product and one of the constituents of silymarin, the standardized, active extract of the fruit of milk thistle, Silybum marianum. It is the second most abundant constituent in silymarin, after silybin. Silychristin is a flavonolignan, along with many other silymarin constituents, meaning it is composed up of a flavonoid and a lignan. It is estimated that up to 65–80% of silymarin extract is made up of flavonolignans, like silychristin, which give silymarin its well known potent antioxidant and hepatoprotective properties. Silychristin can exist as two stereoisomers, silychristin A and silychristin B. The marianum variety of S. marianum includes silychristin A as a major flavonolignan constituent, while the lesser known and studied albiflorum variety includes unique flavonolignans, including silyhermin, (–)-silandrin, and (+)-silymonin.

References

  1. Struijs, K.; Vincken, J. P.; Verhoef, R.; Van Oostveen-Van Casteren, W. H. M.; Voragen, A. G. J.; Gruppen, H. (2007). "The flavonoid herbacetin diglucoside as a constituent of the lignan macromolecule from flaxseed hulls". Phytochemistry. 68 (8): 1227–1235. doi:10.1016/j.phytochem.2006.10.022. PMID   17141814.
  2. Li, T.; Zhang, H. (2008). "Identification and Comparative Determination of Rhodionin in Traditional Tibetan Medicinal Plants of Fourteen Rhodiola Species by High-Performance Liquid Chromatography-Photodiode Array Detection and Electrospray Ionization-Mass Spectrometry". Chemical & Pharmaceutical Bulletin. 56 (6): 807–14. doi: 10.1248/cpb.56.807 . PMID   18520085.
  3. Zapesochnaya, G. G.; Kurkin, V. A. (1983). "The flavonoids of the rhizomes ofRhodiola rosea. II. A flavonolignan and glycosides of herbacetin". Chemistry of Natural Compounds. 19: 21–29. doi:10.1007/BF00579955. S2CID   7656479.