Emodin

Emodin

Names
IUPAC name 1,3,8-trihydroxy-6-methylanthracene-9,10-dione
Other names 6-methyl-1,3,8-trihydroxyanthraquinone
Identifiers
CAS Number	518-82-1
ChEBI	CHEBI:42223
ChEMBL	ChEMBL289277
ChemSpider	3107
DrugBank	DB07715
Jmol interactive 3D	Image
KEGG	C10343
PubChem	3220
UNII	KA46RNI6HN
InChI 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 Key: RHMXXJGYXNZAPX-UHFFFAOYSA-N 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
SMILES O=C2c1cc(cc(O)c1C(=O)c3c2cc(O)cc3O)C
Properties
Chemical formula	C15H10O5
Molar mass	270.24 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)
Boiling point	586.9 ± 39.0 °C [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Emodin (from Rheum emodi, a Himalayan rhubarb) is a purgative resin, 6-methyl-1,3,8-trihydroxyanthraquinone, from rhubarb, buckthorn and Japanese knotweed (Fallopia japonica syn. Polygonum cuspidatum).^[3] It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. Synonyms for emodin include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schuttgelb, and Persian Berry Lake.^[4]

Pharmacology

Emodin is being studied as a potential agent that could reduce the impact of type 2 diabetes. It is a potent selective inhibitor of the enzyme 11β-HSD1.^[5] In studies in obese mice, emodin limits the effect of glucocorticoids and may therefore ameliorate diabetes and insulin resistance.^[6]

Pharmacological studies have demonstrated that emodin when isolated from rhubarb exhibits anti-cancer effects on several human cancers, including human pancreatic cancer.^[7][8][9] Emodin in rhubarb extracts may also have neuroprotective properties against glutamate toxicity.^[10]

Aloe-emodin (1,3,8-trihydroxyanthraquinone) is a variety of emodin found in Socotrine, Barbados, and Zanzibar aloes, but not in Natal aloes.

Emodin is also shown to block cytomegalovirus infections as well as herpes simplex. Research is currently being performed in this area.

List of species that produce emodin

• Senna obtusifolia^[11] (syn. Cassia obtusifolia^[12])
• Fallopia japonica^[13] (syn. Polygonum cuspidatum^[14])
• Ventilago madraspatana^[15]
• Kalimeris indica^[16]
• Rumex nepalensis^[17]
• Polygonum hypoleucum^[18]
• Cassia occidentalis^[19]
• Cassia siamea^[20]
• Acalypha australis^[21]
• Rheum palmatum^[22]
• Thielavia subthermophila^[23]
• Glossostemon bruguieri ^[24]

Compendial status

• British Pharmacopoeia^[25]

• List of compounds with carbon number 15

References

1. Herbal Extract Online. http://herbalextractonline.com/Herbal-Extract/Emodin.html (accessed 9 November 2014).
2. Scifinder (accessed 9 November 2014). Emodin (518-82-1) Experimental Properties.
3. Dorland's Medical Dictionary (1938)
4. PubChem. http://pubchem.ncbi.nlm.nih.gov/compound/emodin (accessed Sept 17, 2014)
5. Feng, Y.; Huang, S. L.; Dou, W.; Zhang, S.; Chen, J. H.; Shen, Y.; Shen, J. H.; Leng, Y. (2010). "Emodin, a Natural Product, Selectively Inhibits 11β-Hydroxysteroid Dehydrogenase Type 1 and Ameliorates Metabolic Disorder in Diet-Induced Obese Mice". British Journal of Pharmacology 161 (1): 113–126. doi:10.1111/j.1476-5381.2010.00826.x. PMC 2962821. PMID 20718744.
6. Novel diabetes hope comes from Chinese herbs, esciencenews.com, 17 August 2010
7. Lin, S.; 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.
8. Sun, Y. (2008). "Chemosensitization by Emodin, a Plant-Derived Anti-Cancer Agent: Mechanism of Action". Cancer Biology & Therapy 7 (3): 476–478. doi:10.4161/cbt.7.3.5584. PMID 18245955.
9. Dorsey, J. F.; Kao, G. D. (2007). "Aloe(-Emodin) for Cancer? More than Just a Comforting Salve" (pdf). Cancer Biology & Therapy 6 (1): 89–90. doi:10.4161/cbt.6.1.3845. PMID 17297301.
10. Gu, J. W.; Hasuo, H.; Takeya, M.; Akasu, T. (2005). "Effects of Emodin on Synaptic Transmission in Rat Hippocampal CA1 Pyramidal Neurons in vitro". Neuropharmacology 49 (1): 103–111. doi:10.1016/j.neuropharm.2005.02.003. PMID 15992585.
11. Dr. Duke's Phytochemical and Ethnobotanical Databases
12. 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.
13. http://www.ars-grin.gov/cgi-bin/duke/highchem.pl
14. 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.
15. 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 & Pharmacology 62 (9): 1158–1166. doi:10.1111/j.2042-7158.2010.01151.x. PMID 20796195.
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. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. http://www.mdpi.net/molecules/papers/80800614.pdf
25. The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 20 April 2010.