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Emodin

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Emodin
Skeletal formula
Ball-and-stick model
Names
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 Edit this at Wikidata
KEGG
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 checkY
    Key: RHMXXJGYXNZAPX-UHFFFAOYSA-N checkY
  • 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
Appearance Orange solid[1]
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).
checkY verify (what is checkY☒N ?)

Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a chemical compound that can be isolated from rhubarb, buckthorn, and Japanese knotweed (Reynoutria japonica syn. Polygonum cuspidatum).[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, 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]

List of plant species

The following plant species produce emodin:

Compendial status

References

  1. ^ Herbal Extract Online. http://herbalextractonline.com/Herbal-Extract/Emodin.html (accessed 9 November 2014).
  2. ^ Dorland's Medical Dictionary (1938)
  3. ^ Palaniyandi, Karyppaiya (3 November 2017). Medicinal Plants – Recent Advances in Research and Development. Singapore : Springer Singapore : Imprint: Springer. 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, Huyiligeqi Ni J. Emodin: A Review of its Pharmacology, Toxicity and Pharmacokinetics. Phytother Res. 2016 Aug;30(8):1207-18. doi:10.1002/ptr.5631 PMID 27188216
  6. ^ Monisha BA, Kumar N, Tiku AB. Emodin and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;928:47-73. PMID 27671812 doi:10.1007/978-3-319-41334-1_3
  7. ^ Ho TY, Wu SL, Chen JC, Li CC, Hsiang CY. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 interaction. Antiviral Res. 2007 May;74(2):92-101. PMID 16730806 doi:10.1016/j.antiviral.2006.04.014
  8. ^ Zhou Y, Hou Y, Shen J, Huang Y, Martin W, Cheng F. Network-based drug repurposing for novel coronavirus 2019-nCoV/SARS-CoV-2. Cell Discov. 2020 Mar 16;6:14. doi:10.1038/s41421-020-0153-3 PMID 32194980
  9. ^ Wang CH, Zhong Y, Zhang Y, Liu JP, Wang YF, Jia WN, Wang GC, Li Z, Zhu Y, Gao XM. A network analysis of the Chinese medicine Lianhua-Qingwen formula to identify its main effective components. Mol Biosyst. 2016 Feb;12(2):606-13. doi:10.1039/c5mb00448a PMID 26687282
  10. ^ Runfeng L, Yunlong H, Jicheng H, Weiqi P, Qinhai M, Yongxia S, Chufang L, Jin Z, Zhenhua J, Haiming J, Kui Z, Shuxiang H, Jun D, Xiaobo L, Xiaotao H, Lin W, Nanshan Z, Zifeng Y. Lianhuaqingwen exerts anti-viral and anti-inflammatory activity against novel coronavirus (SARS-CoV-2). Pharmacol Res. 2020 Mar 20:104761. doi:10.1016/j.phrs.2020.104761 PMID 32205232
  11. ^ Wang, X. L.; Yu, K. B.; Peng, S. L. (2008). "[Chemical constituents of aerial part of Acalypha australis]" [Chemical Constituents of Aerial Part of Acalypha australis]. Zhongguo Zhong Yao Za Zhi [China Journal of Chinese Materia Medica] (in Chinese). 33 (12): 1415–1417. PMID 18837345.
  12. ^ Yadav, J. P.; Arya, V.; Yadav, S.; Panghal, M.; Kumar, S.; Dhankhar, S. (2010). "Cassia occidentalis L.: A Review on its Ethnobotany, Phytochemical and Pharmacological Profile". Fitoterapia. 81 (4): 223–230. doi:10.1016/j.fitote.2009.09.008. PMID 19796670.
  13. ^ Nsonde Ntandou, G. F.; Banzouzi, J. T.; Mbatchi, B.; Elion-Itou, R. D.; Etou-Ossibi, A. W.; Ramos, S.; Benoit-Vical, F.; Abena, A. A.; Ouamba, J. M. (2010). "Analgesic and Anti-Inflammatory Effects of Cassia siamea Lam. Stem Bark Extracts". Journal of Ethnopharmacology. 127 (1): 108–111. doi:10.1016/j.jep.2009.09.040. PMID 19799981.
  14. ^ Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, 10000 Zagreb, Croatia b Dipartimento di Scienze del Farmaco, Università degli Studi "G. d’Annunzio" di Chieti-Pescara, Via dei Vestini 31, 66100 Chieti, Italy (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.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  15. ^ http://www.mdpi.net/molecules/papers/80800614.pdf
  16. ^ Wang, G.; Wang, G. K.; Liu, J. S.; Yu, B.; Wang, F.; Liu, J. K. (2010). "[Studies on the chemical constituents of Kalimeris indica]" [Studies on the Chemical Constituents of Kalimeris indica]. Zhong Yao Cai (in Chinese). 33 (4): 551–554. PMID 20845783.
  17. ^ Chao, P. M.; Kuo, Y. H.; Lin, Y. S.; Chen, C. H.; Chen, S. W.; Kuo, Y. H. (2010). "The Metabolic Benefits of Polygonum hypoleucum Ohwi in HepG2 Cells and Wistar Rats under Lipogenic Stress". Journal of Agricultural and Food Chemistry. 58 (8): 5174–5180. doi:10.1021/jf100046h. PMID 20230058.
  18. ^ "Archived copy". Archived from the original on 16 June 2013. Retrieved 3 May 2011.{{cite web}}: CS1 maint: archived copy as title (link)
  19. ^ Ban, S. H.; Kwon, Y. R.; Pandit, S.; Lee, Y. S.; Yi, H. K.; Jeon, J. G. (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): 30–34. doi:10.1016/j.fitote.2009.06.019. PMID 19616082.
  20. ^ a b Sacerdote, Allison B.; King, Richard B. (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.
  21. ^ Liu, A.; Chen, H.; Wei, W.; Ye, S.; Liao, W.; Gong, J.; Jiang, Z.; Wang, L.; Lin, S. (2011). "Antiproliferative and Antimetastatic Effects of Emodin on Human Pancreatic Cancer". Oncology Reports. 26 (1): 81–89. doi:10.3892/or.2011.1257. PMID 21491088.
  22. ^ Gautam, R.; Karkhile, K. V.; Bhutani, K. K.; Jachak, S. M. (2010). "Anti-Inflammatory, Cyclooxygenase (COX)-2, COX-1 Inhibitory, and Free Radical Scavenging Effects of Rumex nepalensis". Planta Medica. 76 (14): 1564–1569. doi:10.1055/s-0030-1249779. PMID 20379952.
  23. ^ Dr. Duke's Phytochemical and Ethnobotanical Databases
  24. ^ Yang, Y.-C.; Lim, M.-Y.; Lee, H.-S. (2003). "Emodin Isolated from Cassia obtusifolia (Leguminosae) Seed Shows Larvicidal Activity against Three Mosquito Species". Journal of Agricultural and Food Chemistry. 51 (26): 7629–7631. doi:10.1021/jf034727t. PMID 14664519.
  25. ^ Kusari, S.; Zühlke, S.; Košuth, J.; Čellárová, E.; Spiteller, M. (2009). "Light-Independent Metabolomics of Endophytic Thielavia subthermophila Provides Insight into Microbial Hypericin Biosynthesis". Journal of Natural Products. 72 (10): 1825–1835. doi:10.1021/np9002977. PMID 19746917.
  26. ^ Ghosh, S.; Das Sarma, M.; Patra, A.; Hazra, B. (2010). "Anti-Inflammatory and Anticancer Compounds Isolated from Ventilago madraspatana Gaertn., Rubia cordifolia Linn. and Lantana camara Linn". Journal of Pharmacy and Pharmacology. 62 (9): 1158–1166. doi:10.1111/j.2042-7158.2010.01151.x. PMID 20796195.
  27. ^ 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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