Emodin
| Emodin | |
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1,3,8-trihydroxy-6-methylanthracene-9,10-dione[clarification needed] |
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Other names
6-methyl-1,3,8-trihydroxyanthraquinone |
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| Identifiers | |
| CAS number | 518-82-1 |
| PubChem | 3220 |
| ChemSpider | 3107 |
| UNII | KA46RNI6HN |
| DrugBank | DB07715 |
| KEGG | C10343 |
| ChEBI | CHEBI:42223 |
| ChEMBL | CHEMBL289277 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C15H10O5 |
| Molar mass | 270.24 g mol−1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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, the buckthorn and Japanese Knotweed (Fallopia japonica syn. Polygonum cuspidatum).[1] The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb.
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[edit] 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.[2] In studies in obese mice, emodin limits the effect of glucocorticoids and may therefore ameliorate diabetes and insulin resistance.[3]
Pharmacological studies have demonstrated that emodin when isolated from rhubarb exhibits anti-cancer effects on several human cancers including human pancreatic cancer.[4][not in citation given] Emodin in rhubarb extracts may also have neuroprotective properties against glutamate toxicity,[5] but in other studies it seems to increase inflammation and have other possible neurotoxic effects.
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]
[edit] List of plants that contain the chemical
- Cassia obtusifolia[6]
- Fallopia japonica[7], syn. Polygonum cuspidatum[8]
- Senna obtusifolia[9]
- Ventilago madraspatana[10]
- Kalimeris indica[11]
- Rumex nepalensis[12]
- Polygonum hypoleucum[13]
- Cassia occidentalis[14]
- Cassia siamea[15]
- Acalypha australis[16]
- Rheum palmatum[17]
[edit] Compendial status
[edit] References
- ^ Dorland's Medical Dictionary (1938)
- ^ Feng, Y; Huang, SL; Dou, W; Zhang, S; Chen, JH; Shen, Y; Shen, JH; Leng, Y (2010). "Emodin, a natural product, selectively inhibits 11beta-hydroxysteroid dehydrogenase type 1 and ameliorates metabolic disorder in diet-induced obese mice". British journal of pharmacology 161 (1): 113–26. doi:10.1111/j.1476-5381.2010.00826.x. PMC 2962821. PMID 20718744. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2962821.
- ^ Novel diabetes hope comes from Chinese herbs, esciencenews.com, August 17, 2010
- ^ Lee, JK; Jung, JS; Park, SH; Park, SH; Sim, YB; Kim, SM; Ha, TS; Suh, HW (2010). "Anti-inflammatory effect of visnagin in lipopolysaccharide-stimulated BV-2 microglial cells". Archives of pharmacal research 33 (11): 1843–50. doi:10.1007/s12272-010-1117-1. PMID 21116788.
- ^ Gu JW, 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. http://www.ncbi.nlm.nih.gov/pubmed/15992585.
- ^ Yang, Young-Cheol et al. (2003). "Emodin Isolated from Cassia obtusifolia (Leguminosae) Seed Shows Larvicidal Activity against Three Mosquito Species". Journal of Agricultural and Food Chemistry (ACS Publications) 51 (26): 7629–7631. doi:10.1021/jf034727t. PMID 14664519.
- ^ http://www.ars-grin.gov/cgi-bin/duke/highchem.pl
- ^ Ban SH. Kwon YR. Pandit S. Lee YS. Yi HK. Jeon JG.,"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, 2010 Jan.
- ^ Dr. Duke's Phytochemical and Ethnobotanical Databases
- ^ Ghosh S. Das Sarma M. Patra A. Hazra B. ,"Anti-inflammatory and anticancer compounds isolated from Ventilago madraspatana Gaertn., Rubia cordifolia Linn. and Lantana camara Linn.", Journal of Pharmacy & Pharmacology. 62(9):1158-66, 2010 Sep.
- ^ [Studies on the chemical constituents of Kalimeris indica]. [Chinese] Wang G. Wang GK. Liu JS. Yu B. Wang F. Liu JK. Zhong Yao Cai. 33(4):551-4, 2010 Apr.
- ^ Anti-inflammatory, cyclooxygenase (COX)-2, COX-1 inhibitory, and free radical scavenging effects of Rumex nepalensis. Gautam R. Karkhile KV. Bhutani KK. Jachak SM. Planta Medica. 76(14):1564-9, 2010 Oct.
- ^ Chao PM. Kuo YH. Lin YS. Chen CH. Chen SW. Kuo YH. ,"The metabolic benefits of Polygonum hypoleucum Ohwi in HepG2 cells and Wistar rats under lipogenic stress." Journal of Agricultural & Food Chemistry. 58(8):5174-80, 2010 Apr 28.
- ^ Yadav JP. Arya V. Yadav S. Panghal M. Kumar S. Dhankhar S.Cassia occidentalis L.: a review on its ethnobotany, phytochemical and pharmacological profile. [Review] [105 refs]" Fitoterapia. 81(4):223-30, 2010 Jun.
- ^ "Analgesic and anti-inflammatory effects of Cassia siamea Lam. stem bark extracts." Nsonde Ntandou GF. Banzouzi JT. Mbatchi B. Elion-Itou RD. Etou-Ossibi AW. Ramos S. Benoit-Vical F. Abena AA. Ouamba JM. Journal of Ethnopharmacology. 127(1):108-11, 2010 Jan 8.
- ^ Wang XL. Yu KB. Peng SL. Zhongguo Zhong Yao Za Zhi/Zhongguo Zhongyao Zazhi,"Chemical constituents of aerial part of Acalypha australis., [Chinese] China Journal of Chinese Materia Medica. 33(12):1415-7, 2008 Jun.
- ^ Liu A., Chen H., Wei W., Ye S., Liao W., Gong J., Jiang Z., Wang L., Lin S. ,"Antiproliferative and antimetastatic effects of emodin on human pancreatic cancer", [In Process] Oncology Reports 2011 26:1 (81-89)
- ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 20 April 2010.