Emodin

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title: "Emodin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["trihydroxyanthraquinones", "virucides", "resorcinols", "3-hydroxypropenals-within-hydroxyquinones"] topic_path: "general/trihydroxyanthraquinones" source: "https://en.wikipedia.org/wiki/Emodin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 443722128 | ImageFile = Emodin.svg | ImageSize = | ImageName = Skeletal formula | ImageFile1 = Emodin-3D-balls.png | ImageSize1 = | ImageName1 = Ball-and-stick model | PIN = 1,3,8-Trihydroxy-6-methylanthracene-9,10-dione | OtherNames = 6-Methyl-1,3,8-trihydroxyanthraquinone | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 3107 | KEGG_Ref = | KEGG = C10343 | 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 | InChIKey = RHMXXJGYXNZAPX-UHFFFAOYAD | ChEMBL_Ref = | ChEMBL = 289277 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = RHMXXJGYXNZAPX-UHFFFAOYSA-N | CASNo_Ref = | CASNo =518-82-1 | PubChem =3220 | DrugBank_Ref = | DrugBank = DB07715 | UNII_Ref = | UNII = KA46RNI6HN | ChEBI_Ref = | ChEBI = 42223 | SMILES = O=C2c1cc(cc(O)c1C(=O)c3c2cc(O)cc3O)C | Section2 = {{Chembox Properties | C=15 | H=10 | O=5 | Appearance = Orange solid | Density = 1.583±0.06 g/cm3 | MeltingPtC = 256 to 257 | BoilingPt = | BoilingPt_ref = | Solubility = 4.3 x 10 mol/L | Section3 = {{Chembox Hazards |Hazards_ref = |GHSPictograms = |HPhrases = |PPhrases = | MainHazards = | FlashPt = | AutoignitionPt =

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). 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). It is specifically isolated from Rheum palmatum L. 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.

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, anticancer, antibacterial and antiinflammatory effects, and has also been identified as having potential antiviral activity against coronaviruses such as SARS-CoV-2, being one of the major active components of the antiviral TCM formulation Lianhua Qingwen.

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.

List of species

The following plant species are known to produce emodin:

Compendial status

  • British Pharmacopoeia{{cite web |last=The British Pharmacopoeia Secretariat |title=Index, BP 2009 |year=2009 |url=http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf |access-date=20 April 2010 |archive-url=https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf |archive-date=11 April 2009

  • List of compounds with carbon number 15

References

References

  1. "Emodin". National Institute of Health.
  2. [[Dorland's Medical Dictionary]] (1938)
  3. (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.
  4. (3 November 2017). "Medicinal Plants – Recent Advances in Research and Development". Springer Singapore.
  5. {{PubChem. 3220
  6. (August 2016). "Emodin: A Review of its Pharmacology, Toxicity and Pharmacokinetics". Phytotherapy Research.
  7. (2016). "Anti-inflammatory Nutraceuticals and Chronic Diseases".
  8. (2012-09-01). "Anticancer potential of emodin". BioMedicine.
  9. (May 2007). "Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 interaction". Antiviral Research.
  10. (2020). "Network-based drug repurposing for novel coronavirus 2019-nCoV/SARS-CoV-2". Cell Discovery.
  11. (February 2016). "A network analysis of the Chinese medicine Lianhua-Qingwen formula to identify its main effective components". Molecular BioSystems.
  12. (June 2020). "Lianhuaqingwen exerts anti-viral and anti-inflammatory activity against novel coronavirus (SARS-CoV-2)". Pharmacological Research.
  13. (April 2011). "Emodin inhibits current through SARS-associated coronavirus 3a protein". Antiviral Research.
  14. (June 2008). "[Chemical constituents of aerial part of Acalypha australis]". Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica.
  15. (June 2010). "Cassia occidentalis L.: a review on its ethnobotany, phytochemical and pharmacological profile". Fitoterapia.
  16. (January 2010). "Analgesic and anti-inflammatory effects of Cassia siamea Lam. stem bark extracts". Journal of Ethnopharmacology.
  17. (April 2012). "Anthraquinone profiles, antioxidant and antimicrobial properties of Frangula rupestris (Scop.) Schur and Frangula alnus Mill. bark". Food Chemistry.
  18. (August 2003). "Constituents from Moghat, the Roots of Glossostemon bruguieri (Desf.)". Molecules.
  19. (April 2010). "[Studies on the chemical constituents of Kalimeris indica]". Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials.
  20. (April 2010). "The metabolic benefits of Polygonum hypoleucum Ohwi in HepG2 cells and Wistar rats under lipogenic stress". Journal of Agricultural and Food Chemistry.
  21. "Reynoutria japonica (Polygonaceae)". U.S. Department of Agriculture.
  22. (January 2010). "Effects of a bio-assay guided fraction from Polygonum cuspidatum root on the viability, acid production and glucosyltranferase of mutans streptococci". Fitoterapia.
  23. (2014). "Direct Effects of an Invasive European Buckthorn Metabolite on Embryo Survival and Development in Xenopus laevis and Pseudacris triseriata". Journal of Herpetology.
  24. (July 2011). "Antiproliferative and antimetastatic effects of emodin on human pancreatic cancer". Oncology Reports.
  25. (October 2010). "Anti-inflammatory, cyclooxygenase (COX)-2, COX-1 inhibitory, and free radical scavenging effects of Rumex nepalensis". Planta Medica.
  26. "Senna obtusifolia (Fabaceae)". U.S. Department of Agriculture.
  27. (December 2003). "Emodin isolated from Cassia obtusifolia (Leguminosae) seed shows larvicidal activity against three mosquito species". Journal of Agricultural and Food Chemistry.
  28. (October 2009). "Light-independent metabolomics of endophytic Thielavia subthermophila provides insight into microbial hypericin biosynthesis". Journal of Natural Products.
  29. (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.
  30. (2014). "''Catenarina'' (Teloschistaceae, Ascomycota), a new Southern Hemisphere genus with 7-chlorocatenarin". The Lichenologist.

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trihydroxyanthraquinonesvirucidesresorcinols3-hydroxypropenals-within-hydroxyquinones