Jump to content

Emodin

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Myasuda (talk | contribs) at 02:11, 28 June 2016 (→List of species that produce emodin: sp). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Emodin
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1,3,8-trihydroxy-6-methylanthracene-9,10-dione [clarification needed]
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)
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).
checkY verify (what is checkY☒N ?)

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.[citation needed]

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

Compendial status

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 [dead link]
  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]". Zhong Yao Cai (in Chinese). 33 (4): 551–554. PMID 20845783. {{cite journal}}: Unknown parameter |trans_title= ignored (|trans-title= suggested) (help)
  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]". Zhongguo Zhong Yao Za Zhi [China Journal of Chinese Materia Medica] (in Chinese). 33 (12): 1415–1417. PMID 18837345. {{cite journal}}: Unknown parameter |trans_title= ignored (|trans-title= suggested) (help)
  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. ^ 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.
  26. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 20 April 2010.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Emodin&oldid=727300683"