Embelin

Embelin (2,5-dihydroxy-3-undecyl-1,4-benzoquinone) is a naturally occurring para-benzoquinone isolated from dried berries of Embelia ribes plants.[1][2] Embelin has a wide spectrum of biological activities, including antioxidant, antitumor, anti-inflammatory, analgesic, anthelmintic, antifertility and antimicrobial.[3][4][5] Several studies have reported antidiabetic activity of embelin[6] Embelin treatment significantly decreased paraquat‐induced lung injury through suppressing oxidative stress, inflammatory cascade (inflammatory cytokines release), and MAPK/NF‐κB signaling pathway in paraquat‐intoxicated rats[7] Embelin and embelin derivatives selectively inhibits 5-LOX and microsomal prostaglandin E2 synthase-1[8][9]

Embelin
Names
Preferred IUPAC name
2,5-Dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
Other names
Embelic acid, Emberine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.164
EC Number
  • 208-979-8
KEGG
UNII
  • InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
    Key: IRSFLDGTOHBADP-UHFFFAOYSA-N
  • CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O
Properties
C17H26O4
Molar mass 294.391 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H361
P201, P202, P281, P308+P313, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Radhakrishnan, N., & Gnanamani, A. (2014). 2, 5-dihydroxy-3-undecyl-1, 4-benzoquinone (Embelin)-A second solid gold of India-A Review. International Journal Pharmacy & Pharmaceutical Sciences, 6(6), 23-30.
  2. Poojari, R. (2014). Embelin–a drug of antiquity: shifting the paradigm towards modern medicine. Expert opinion on investigational drugs, 23(3), 427-444. PMID 24397264 doi:10.1517/13543784.2014.867016
  3. Sheng, Z., Ge, S., Gao, M., Jian, R., Chen, X., Xu, X., ... & Chen, W. H. (2020). Synthesis and biological activity of embelin and its derivatives: an overview. Mini Reviews in Medicinal Chemistry, 20(5), 396-407. PMID 31644404 doi:10.2174/1389557519666191015202723
  4. Lu, H., Wang, J., Wang, Y., Qiao, L., & Zhou, Y. (2016). Embelin and its role in chronic diseases. In Anti-inflammatory Nutraceuticals and Chronic Diseases (pp. 397-418). Springer, Cham. PMID 27671825 doi:10.1007/978-3-319-41334-1_16
  5. Chen, X., Gao, M., Jian, R., Hong, W. D., Tang, X., Li, Y., Zhao, D., Zhang, K., Chen, W., Zheng, X., Sheng, Z., Wu, P. (2020). Design, synthesis and α-glucosidase inhibition study of novel embelin derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry, 35(1), 565-573. doi:10.1080/14756366.2020.1715386 PMC 7006637 PMID 31969031
  6. Durg, S., Veerapur, V. P., Neelima, S., & Dhadde, S. B. (2017). Antidiabetic activity of Embelia ribes, embelin and its derivatives: A systematic review and meta-analysis. Biomedicine & Pharmacotherapy, 86, 195-204. PMID 27984799 doi:10.1016/j.biopha.2016.12.001
  7. SreeHarsha, N. (2020). Embelin impact on paraquat‐induced lung injury through suppressing oxidative stress, inflammatory cascade, and MAPK/NF‐κB signaling pathway. Journal of Biochemical and Molecular Toxicology. PMID 32020686 doi:10.1002/jbt.22456
  8. Schaible, A. M., Traber, H., Temml, V., Noha, S. M., Filosa, R., Peduto, A., Weinigel, C., Barz, D., Schuster, D., Werz, O. (2013). Potent inhibition of human 5-lipoxygenase and microsomal prostaglandin E2 synthase-1 by the anti-carcinogenic and anti-inflammatory agent embelin. Biochemical Pharmacology, 86(4), 476-486. PMID 23623753 doi:10.1016/j.bcp.2013.04.015
  9. Filosa, R., Peduto, A., Schaible, A. M., Krauth, V., Weinigel, C., Barz, D., ... & D'Agostino, B. (2015). Novel series of benzoquinones with high potency against 5-lipoxygenase in human polymorphonuclear leukocytes. European Journal of Medicinal Chemistry, 94, 132-139. PMID 25765759 doi:10.1016/j.ejmech.2015.02.042
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