Emodin

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Contents

Emodin
Skeletal formula Emodin.svg
Skeletal formula
Ball-and-stick model Emodin-3D-balls.png
Ball-and-stick model
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)
4.3 x 10-6 mol/L
Hazards [1]
GHS labelling:
GHS-pictogram-exclam.svg
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
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). [2] 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). [3] It is specifically isolated from Rheum palmatum L. [4] 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. [5]

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, [6] [7] [8] and has also been identified as having potential antiviral activity against coronaviruses such as SARS-CoV-2, [9] [10] being one of the major active components of the antiviral TCM formulation Lianhua Qingwen. [11] [12]

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. [13]

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 . [30]

Compendial status

References

  1. ↑ "Emodin". PubChem. National Institute of Health. Retrieved 15 November 2024.
  2. ↑ Dorland's Medical Dictionary (1938)
  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.
  4. ↑ 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.
  5. ↑ CID 3220 from PubChem
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ Hsu SC, Chung JG (1 September 2012). "Anticancer potential of emodin". BioMedicine. 2 (3): 108–116. doi:10.1016/j.biomed.2012.03.003. ISSN   2211-8020. PMC   7104001 . PMID   32289000.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ Wang CH, Zhong Y, Zhang Y, Liu JP, Wang YF, Jia WN, et al. (February 2016). "A network analysis of the Chinese medicine Lianhua-Qingwen formula to identify its main effective components". Molecular BioSystems. 12 (2): 606–13. doi:10.1039/c5mb00448a. PMID   26687282.
  12. ↑ Runfeng L, Yunlong H, Jicheng H, Weiqi P, Qinhai M, Yongxia S, et al. (June 2020). "Lianhuaqingwen exerts anti-viral and anti-inflammatory activity against novel coronavirus (SARS-CoV-2)". Pharmacological Research. 156: 104761. doi:10.1016/j.phrs.2020.104761. PMC   7102548 . PMID   32205232.
  13. ↑ 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.
  14. ↑ Wang XL, Yu KB, Peng SL (June 2008). "[Chemical constituents of aerial part of Acalypha australis]" [Chemical Constituents of Aerial Part of Acalypha australis]. Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica (in Chinese). 33 (12): 1415–7. PMID   18837345.
  15. ↑ 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.
  16. ↑ 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.
  17. ↑ 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.
  18. ↑ Meselhy MR (August 2003). "Constituents from Moghat, the Roots of Glossostemon bruguieri (Desf.)". Molecules. 8 (8): 614–621. doi: 10.3390/80800614 . PMC   6146927 .
  19. ↑ Wang G, Wang GK, Liu JS, Yu B, Wang F, Liu JK (April 2010). "[Studies on the chemical constituents of Kalimeris indica]" [Studies on the Chemical Constituents of Kalimeris indica]. Zhong Yao Cai = Zhongyaocai = Journal of Chinese Medicinal Materials (in Chinese). 33 (4): 551–4. PMID   20845783.
  20. ↑ 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. Bibcode:2010JAFC...58.5174C. doi:10.1021/jf100046h. PMID   20230058.
  21. ↑ "Reynoutria japonica (Polygonaceae)". Dr. Duke's Phytochemical and Ethnobotanical Databases. U.S. Department of Agriculture. Archived from the original on 6 June 2021.
  22. ↑ 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.
  23. 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.
  24. ↑ 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.
  25. ↑ 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.
  26. ↑ "Senna obtusifolia (Fabaceae)". Dr. Duke's Phytochemical and Ethnobotanical Databases. U.S. Department of Agriculture. Archived from the original on 6 June 2021.
  27. ↑ 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. Bibcode:2003JAFC...51.7629Y. doi:10.1021/jf034727t. PMID   14664519.
  28. ↑ 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.
  29. ↑ 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.
  30. ↑ 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.
  31. ↑ 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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