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 a chemical compound, of the anthraquinone family, that 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]

A computational study was conducted to investigate the inhibition mechanism on the formation of the Spike-ACE2 protein complex. [2] Specifically, it is seen dose-dependent inhibition in the prevention of infection by SARS-CoV-1, evidence which has stimulated further investigations on SARS-CoV-2. [2]

Emodin has been shown to inhibit the ion channel of protein 3a, which could play a crucial 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

<i>Lonicera japonica</i> Flowering shrub known as Japanese honeysuckle

Lonicera japonica, known as Japanese honeysuckle and golden-and-silver honeysuckle, is a species of honeysuckle native to East Asia, including many parts of China. It is often grown as an ornamental plant, but has become an invasive species in a number of countries. Japanese honeysuckle is used in traditional Chinese medicine.

<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">SARS-CoV-1</span> Virus that causes SARS

Severe acute respiratory syndrome coronavirus 1 (SARS-CoV-1), previously known as severe acute respiratory syndrome coronavirus (SARS-CoV), is a strain of coronavirus that causes severe acute respiratory syndrome (SARS), the respiratory illness responsible for the 2002–2004 SARS outbreak. It is an enveloped, positive-sense, single-stranded RNA virus that infects the epithelial cells within the lungs. The virus enters the host cell by binding to angiotensin-converting enzyme 2. It infects humans, bats, and palm civets. The SARS-CoV-1 outbreak was largely brought under control by simple public health measures. Testing people with symptoms, isolating and quarantining suspected cases, and restricting travel all had an effect. SARS-CoV-1 was most transmissible when patients were sick, so its spread could be effectively suppressed by isolating patients with symptoms.

<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">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 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.

Aphalara itadori, the Japanese knotweed psyllid, is a species of psyllid from Japan which feeds on Japanese knotweed.

<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.

References

  1. ↑ Dorland's Medical Dictionary (1938)
  2. 1 2 3 Dellafiora L, Dorne JL, Galaverna G, Dall'Asta C (2020). "Preventing the Interaction between Coronaviruses Spike Protein and Angiotensin I Converting Enzyme 2: An in Silico Mechanistic Case Study on Emodin as a Potential Model Compound". Applied Sciences. 10 (18): 6358. doi: 10.3390/app10186358 . S2CID   224994102.
  3. ↑ Tsay HS, Shyur LF, Agrawal DC, Wu YC, Wang SY (3 November 2017). Medicinal Plants – Recent Advances in Research and Development. Singapore: Springer Singapore. p. 339. ISBN   978-981-10-5978-0.
  4. ↑ CID 3220 from PubChem
  5. ↑ Dong X, Fu J, Yin X, Cao S, Li X, Lin L, Ni J (August 2016). "Emodin: A Review of its Pharmacology, Toxicity and Pharmacokinetics". Phytotherapy Research. 30 (8): 1207–18. doi:10.1002/ptr.5631. PMC   7168079 . PMID   27188216.
  6. ↑ Monisha BA, Kumar N, Tiku AB (2016). "Emodin and Its Role in Chronic Diseases". Anti-inflammatory Nutraceuticals and Chronic Diseases. Advances in Experimental Medicine and Biology. Vol. 928. pp. 47–73. doi:10.1007/978-3-319-41334-1_3. ISBN   978-3-319-41332-7. PMID   27671812.
  7. ↑ Ho TY, Wu SL, Chen JC, Li CC, Hsiang CY (May 2007). "Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 interaction". Antiviral Research. 74 (2): 92–101. doi:10.1016/j.antiviral.2006.04.014. PMC   7114332 . PMID   16730806.
  8. ↑ Zhou Y, Hou Y, Shen J, Huang Y, Martin W, Cheng F (2020). "Network-based drug repurposing for novel coronavirus 2019-nCoV/SARS-CoV-2". Cell Discovery. 6: 14. doi: 10.1038/s41421-020-0153-3 . PMC   7073332 . PMID   32194980.
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  11. ↑ Schwarz S, Wang K, Yu W, Sun B, Schwarz W (April 2011). "Emodin inhibits current through SARS-associated coronavirus 3a protein". Antiviral Research. 90 (1): 64–9. doi:10.1016/j.antiviral.2011.02.008. PMC   7114100 . PMID   21356245.
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  13. ↑ Yadav JP, Arya V, Yadav S, Panghal M, Kumar S, Dhankhar S (June 2010). "Cassia occidentalis L.: a review on its ethnobotany, phytochemical and pharmacological profile". Fitoterapia. 81 (4): 223–30. doi:10.1016/j.fitote.2009.09.008. PMID   19796670.
  14. ↑ Nsonde Ntandou GF, Banzouzi JT, Mbatchi B, Elion-Itou RD, Etou-Ossibi AW, Ramos S, et al. (January 2010). "Analgesic and anti-inflammatory effects of Cassia siamea Lam. stem bark extracts". Journal of Ethnopharmacology. 127 (1): 108–11. doi:10.1016/j.jep.2009.09.040. PMID   19799981.
  15. ↑ Kremer D, Kosalec I, Locatelli M, Epifano F, Genovese S, Carlucci G, Končić MZ (April 2012). "Anthraquinone profiles, antioxidant and antimicrobial properties of Frangula rupestris (Scop.) Schur and Frangula alnus Mill. bark". Food Chemistry. 131 (4): 1174–1180. doi:10.1016/j.foodchem.2011.09.094.
  16. ↑ Meselhy MR (August 2003). "Constituents from Moghat, the Roots of Glossostemon bruguieri (Desf.)". Molecules. 8 (8): 614–621. doi: 10.3390/80800614 . PMC   6146927 .
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  18. ↑ Chao PM, Kuo YH, Lin YS, Chen CH, Chen SW, Kuo YH (April 2010). "The metabolic benefits of Polygonum hypoleucum Ohwi in HepG2 cells and Wistar rats under lipogenic stress" (PDF). Journal of Agricultural and Food Chemistry. 58 (8): 5174–80. doi:10.1021/jf100046h. PMID   20230058.
  19. ↑ "Reynoutria japonica (Polygonaceae)". Dr. Duke's Phytochemical and Ethnobotanical Databases. U.S. Department of Agriculture.
  20. ↑ Ban SH, Kwon YR, Pandit S, Lee YS, Yi HK, Jeon JG (January 2010). "Effects of a bio-assay guided fraction from Polygonum cuspidatum root on the viability, acid production and glucosyltranferase of mutans streptococci". Fitoterapia. 81 (1): 30–4. doi:10.1016/j.fitote.2009.06.019. PMID   19616082.
  21. 1 2 Sacerdote AB, King RB (2014). "Direct Effects of an Invasive European Buckthorn Metabolite on Embryo Survival and Development in Xenopus laevis and Pseudacris triseriata" (PDF). Journal of Herpetology. 48 (1): 51–58. doi:10.1670/12-066. S2CID   62818226.
  22. ↑ Liu A, Chen H, Wei W, Ye S, Liao W, Gong J, et al. (July 2011). "Antiproliferative and antimetastatic effects of emodin on human pancreatic cancer". Oncology Reports. 26 (1): 81–9. doi: 10.3892/or.2011.1257 . PMID   21491088.
  23. ↑ Gautam R, Karkhile KV, Bhutani KK, Jachak SM (October 2010). "Anti-inflammatory, cyclooxygenase (COX)-2, COX-1 inhibitory, and free radical scavenging effects of Rumex nepalensis". Planta Medica. 76 (14): 1564–9. doi:10.1055/s-0030-1249779. PMID   20379952. S2CID   260253513.
  24. ↑ "Senna obtusifolia (Fabaceae)". Dr. Duke's Phytochemical and Ethnobotanical Databases. U.S. Department of Agriculture.
  25. ↑ Yang YC, Lim MY, Lee HS (December 2003). "Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species". Journal of Agricultural and Food Chemistry. 51 (26): 7629–31. doi:10.1021/jf034727t. PMID   14664519.
  26. ↑ Kusari S, Zühlke S, Kosuth J, Cellárová E, Spiteller M (October 2009). "Light-independent metabolomics of endophytic Thielavia subthermophila provides insight into microbial hypericin biosynthesis". Journal of Natural Products. 72 (10): 1825–35. doi:10.1021/np9002977. PMID   19746917.
  27. ↑ Ghosh S, Das Sarma M, Patra A, Hazra B (September 2010). "Anti-inflammatory and anticancer compounds isolated from Ventilago madraspatana Gaertn., Rubia cordifolia Linn. and Lantana camara Linn". The Journal of Pharmacy and Pharmacology. 62 (9): 1158–66. doi: 10.1111/j.2042-7158.2010.01151.x . PMID   20796195. S2CID   25769269.
  28. ↑ Søchting U, Søgaard MZ, Elix JA, Arup U, Elvebakk A, sancho LG (2014). "Catenarina (Teloschistaceae, Ascomycota), a new Southern Hemisphere genus with 7-chlorocatenarin". The Lichenologist. 46 (2): 175–187. doi:10.1017/s002428291300087x. S2CID   83906534.
  29. ↑ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 20 April 2010.
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