Emodin

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Contents

Emodin
Emodin.svg
Emodin-3D-balls.png
Names
Preferred IUPAC name
1,3,8-Trihydroxy-6-methylanthracene-9,10-dione
Other names
6-Methyl-1,3,8-trihydroxyanthraquinone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.509 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3 Yes check.svgY
    Key: RHMXXJGYXNZAPX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3
    Key: RHMXXJGYXNZAPX-UHFFFAOYAD
  • O=C2c1cc(cc(O)c1C(=O)c3c2cc(O)cc3O)C
Properties
C15H10O5
Molar mass 270.240 g·mol−1
AppearanceOrange solid
Density 1.583±0.06 g/cm3
Melting point 256 to 257 °C (493 to 495 °F; 529 to 530 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is an organic compound. Classified as an anthraquinone,it can be isolated from rhubarb, buckthorn, and Japanese knotweed ( Reynoutria japonica syn. Polygonum cuspidatum). [1] Emodin is particularly abundant in the roots of the Chinese rhubarb ( Rheum palmatum ), knotweed and knotgrass ( Polygonum cuspidatum and Polygonum multiflorum ) as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed (Semen cassia). [2] It is specifically isolated from Rheum palmatum L. [3] It is also produced by many species of fungi, including members of the genera Aspergillus , Pyrenochaeta , and Pestalotiopsis , inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe , (Himalayan rhubarb) and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schüttgelb (Schuttgelb), and Persian Berry Lake. [4]

Pharmacology

Emodin is an active component of several plants used in traditional Chinese medicine (TCM) such as Rheum palmatum , Polygonum cuspidatum , and Polygonum multiflorum . It has various actions including laxative, antibacterial and antiinflammatory effects, [5] [6] and has also been identified as having potential antiviral activity against coronaviruses such as SARS-CoV-2, [7] [8] being one of the major active components of the antiviral TCM formulation Lianhua Qingwen. [9] [10]

Emodin has been shown to inhibit the ion channel of protein 3a, which could play a role in the release of the virus from infected cells. [11]

List of species

The following plant species are known to produce emodin:

Emodin also occurs in variable amounts in members of the crustose lichen genus Catenarina . [28]

Compendial status

Related Research Articles

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

Hypericin is a naphthodianthrone, an anthraquinone derivative which, together with hyperforin, is one of the principal active constituents of Hypericum. Hypericin is believed to act as an antibiotic, antiviral and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine β-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine.

<i>Polygonum</i> Genus of flowering plants in the knotweed family Polygonaceae

Polygonum is a genus of about 130 species of flowering plants in the buckwheat and knotweed family Polygonaceae. Common names include knotweed and knotgrass. In the Middle English glossary of herbs Alphita, it was known as ars-smerte. There have been various opinions about how broadly the genus should be defined. For example, buckwheat has sometimes been included in the genus as Polygonum fagopyrum. Former genera such as Polygonella have been subsumed into Polygonum; other genera have been split off.

<i>Fallopia</i> Genus of flowering plants in the knotweed family Polygonaceae

Fallopia is a genus of about 12 species of flowering plants in the buckwheat family, often included in a wider treatment of the related genus Polygonum in the past, and previously including Reynoutria. The genus is native to temperate and subtropical regions of the Northern Hemisphere, but species have been introduced elsewhere. The genus includes species forming vines and shrubs.

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

Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates.

<span class="mw-page-title-main">Anthraquinones</span> Type of compounds

For the parent molecule 9,10-anthraquinone, see anthraquinone

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

Umifenovir, sold under the brand name Arbidol, is sold and used as an antiviral medication for influenza in Russia and China. The drug is manufactured by Pharmstandard. It is not approved by the U.S. Food and Drug Administration (FDA) for the treatment or prevention of influenza.

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

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can be found in the bark of Picea sitchensis. It can also be isolated from Reynoutria japonica, the Japanese knotweed.

<i>Reynoutria multiflora</i> Species of flowering plant

Reynoutria multiflora is a species of flowering plant in the buckwheat family Polygonaceae native to central and southern China. It is known by the English common names tuber fleeceflower and Chinese (climbing) knotweed. It is known as he shou wu in China and East Asia. Another name for the species is fo-ti, which is a misnomer.

<i>Reynoutria sachalinensis</i> Species of flowering plant in the knotweed family Polygonaceae

Reynoutria sachalinensis (giant knotweed or Sakhalin knotweed is a species of Fallopia native to northeastern Asia in northern Japan and the far east of Russia.

<i>Rhamnus cathartica</i> Species of flowering plant in the buckthorn family Rhamnaceae

Rhamnus cathartica, the European buckthorn, common buckthorn, purging buckthorn, or just buckthorn, is a species of small tree in the flowering plant family Rhamnaceae. It is native to Europe, northwest Africa and western Asia, from the central British Isles south to Morocco, and east to Kyrgyzstan. It was introduced to North America as an ornamental shrub in the early 19th century or perhaps before, and is now naturalized in the northern half of the continent, and is classified as an invasive plant in several US states and in Ontario, Canada.

<i>Frangula alnus</i> Species of flowering plant in the family Rhamnaceae

Frangula alnus, commonly known as alder buckthorn, glossy buckthorn, or breaking buckthorn, is a tall deciduous shrub in the family Rhamnaceae. Unlike other "buckthorns", alder buckthorn does not have thorns. It is native to Europe, northernmost Africa, and western Asia, from Ireland and Great Britain north to the 68th parallel in Scandinavia, east to central Siberia and Xinjiang in western China, and south to northern Morocco, Turkey, and the Alborz in Iran and the Caucasus Mountains; in the northwest of its range, it is rare and scattered. It is also introduced and naturalised in eastern North America.

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

Aloe emodin is an anthraquinone and an isomer of emodin present in aloe latex, an exudate from the aloe plant. It has a strong stimulant-laxative action. Aloe emodin is not carcinogenic when applied to the skin, although it may increase the carcinogenicity of some kinds of radiation.

<i>Persicaria capitata</i> Species of plant

Persicaria capitata, the pink-headed persicaria, pinkhead smartweed, pink knotweed, Japanese knotweed, or pink bubble persicaria, is an Asian species of plants in the genus Persicaria within the buckwheat family. It is native to Asia and grown as an ornamental in other countries. It has become naturalized in Australia, South Africa and a few scattered locations in the Americas.

<span class="mw-page-title-main">Rhein (molecule)</span> Chemical compound

Rhein, also known as cassic acid, is a substance in the anthraquinone group obtained from rhubarb. Like all such substances, rhein is a cathartic, which is commonly found as a glycoside such as rhein-8-glucoside or glucorhein. Rhein was first isolated in 1895. It is found in rhubarb species like Rheum undulatum and Rheum palmatum as well as in Cassia reticulata.

Catechin-7-<i>O</i>-glucoside Chemical compound

Catechin-7-O-glucoside is a flavan-3-ol glycoside formed from catechin.

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

(S)-Magnoflorine is a quaternary benzylisoquinoline alkaloid (BIA) of the aporphine structural subgroup which has been isolated from various species of the family Menispermaceae, such as Pachygone ovata,Sinomenium acutum, and Cissampelos pareira. 

Ann P. Conolly (1917–2010) was a British botanist and teacher who contributed to quaternary botany and conducted important early work on the history and spread of Japanese Knotweed in the UK.

<i>Reynoutria</i> Genus of flowering plants in the knotweed family Polygonaceae

Reynoutria is a genus of flowering plants in the Polygonaceae, also known as the knotweed or buckwheat family. The genus is native to eastern China, Eastern Asia and the Russian Far East, although species have been introduced to Europe and North America. Members of the genus, including R. japonica and its hybrid with R. sachalinensis, are highly invasive plants.

<span class="mw-page-title-main">Polygonoideae</span> Subfamily of the knotweed family of plants (Polygonaceae)

Polygonoideae is a subfamily of plants in the family Polygonaceae. It includes a number of plants that can be highly invasive, such as Japanese knotweed, Reynoutria japonica, and its hybrid with R. sachalinensis, R. × bohemica. Boundaries between the genera placed in the subfamily and their relationships have long been problematic, but a series of molecular phylogenetic studies have clarified some of them, resulting in the division of the subfamily into seven tribes.

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