Medicinal Chemistry Research

, Volume 21, Issue 7, pp 995–999 | Cite as

Synthesis of aspirin eugenol ester and its biological activity

  • Jian-yong Li
  • Yuan-guang Yu
  • Qi-wen Wang
  • Ji-yu Zhang
  • Ya-jun Yang
  • Bing Li
  • Xu-zheng Zhou
  • Jian-rong Niu
  • Xiao-juan Wei
  • Xi-wang Liu
  • Zhi-qi Liu
Original Research
First Online:
Received:
Accepted:

Abstract

Aspirin, as starting precursor, was reacted with SOCl2 to generate acyl chloride compound via esterifying eugenol to aspirin eugenol ester (AEE) with a yield of 65%. Tests of AEE for acute toxicity, anti-inflammatory, analgesic, and antipyretic effects were carried out in mice and rats. The results showed that toxicity of AEE was significantly reduced, about 50 and 3.7 times lower than aspirin and eugenol, respectively. Its strength of anti-inflammation, analgesia, and antipyresis was similar as aspirin and eugenol, but the effects lasted longer.

Keywords

Aspirin eugenol ester (AEE) Synthesis Toxicity Anti-inflammation Analgesic and antipyretic effects 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgments

NMR, EIMS, and element analysis were carried out in the center of analysis and identification, department of chemistry, Lanzhou University. The project was supported by Specific Program Funded by Basic Scientific Research Operating Expenses of Central Public Scientific Research Institutes of China (BRF060403), Key Project of Scientific and Technical Supporting Programs of Gansu Province of China (0804NKCA074).

References

  1. Cayman Chemical Company (2005) Aspirin. MATERIAL SAFETY DATA SHEET:3Google Scholar
  2. Chami N, Bennis S, Chami F, Aboussekhra A, Remmal A (2005) Study of anticandidal activity of carvacrol and eugenol in vitro and in vivo. Oral Microbiol Immunol 20:106–111PubMedCrossRefGoogle Scholar
  3. Feng J, Lipton JM (1987) Eugenol: antipyretic activity in rabbits. Neuropharmacology 26:1775–1778PubMedCrossRefGoogle Scholar
  4. Flower R, Gryglewshi R, Herbaczynska-cedro K, Vane JR (1972) Effects of anti-inflammatory drugs on prostaglandin biosynthesis. Nat New Biol 238:104–106PubMedGoogle Scholar
  5. Gill AO, Holley RA (2004) Mechanisms of bactericidal action of cinnamaldehyde against Listeria monocytogenes and of eugenol against L. monocytogenes and Lactobacillus sakei. Appl Environ Microbiol 70:5750–5755PubMedCrossRefGoogle Scholar
  6. Hashimoto S, Uchiyama K, Maeda M, Ishitsuka K, Furumoto K, Nakamura Y (1988) In vivo and in vitro effects of zinc oxide-eugenol (ZOE) on biosynthesis of cyclo-oxygenase products in rat dental pulp. J Dent Res 67:1092–1096PubMedCrossRefGoogle Scholar
  7. Li SQ (2003) Principal and method for animal toxicology, 2nd edn. Sichuan university publishing house, Chengdu, p 56Google Scholar
  8. Li J, Wang L, Bai H, Yang B, Yang H (2009) Synthesis, characterization, and anti-inflammatory activities of rare earth metal complexes of luteolin. Med Chem Res 18:1–5. doi: 10.1007/s00044-009-9289-2 CrossRefGoogle Scholar
  9. Nagababu E, Lakshmaiah N (1997) Inhibition of xanthine oxidase–xanthine–iron mediated lipid peroxidation by eugenol in liposomes. Mol Cell Biochem 166:65–71PubMedCrossRefGoogle Scholar
  10. Nigade G, Chavan P, Deodhar M (2010) Synthesis and analgesic activity of new pyridine-based heterocyclic derivatives. Med Chem Res 19:1–11. doi: 10.1007/s00044-010-9489-9 Google Scholar
  11. Patrono C (1989) Aspirin and human platelets from clinical trials to acetylation of cyclooxygenase and back. TiPS 10:453–458PubMedGoogle Scholar
  12. Raghavendra RH, Naidu KA (2009) Spice active principles as the inhibitors of human platelet aggregation and thromboxane biosynthesis. Prostaglandins Leukot Essent Fatty Acids 81:73–78PubMedCrossRefGoogle Scholar
  13. Schoemaker RG, Saxena PR, Kalkman EA (1998) Low-dose aspirin improves in vivo hemodynamics in conscious, chronically infarcted rats. Cardiovasc Res 37:108–114PubMedCrossRefGoogle Scholar
  14. Tragoolpua Y, Jatisatienr A (2007) Anti-herpes simplex virus activities of Eugenia caryophyllus (Spreng.) Bullock & S. G. Harrison and essential oil, eugenol. Phytother Res 21:1153–1158PubMedCrossRefGoogle Scholar
  15. Vane JR (1971) Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol 231:232–235PubMedGoogle Scholar
  16. Vane JR, Botting R (1987) Inflammation and mechanism of anti-inflammatory drugs. FASEB J 1:89–96PubMedGoogle Scholar
  17. Wallenburg HC, Dekker GA, Makovitz JW, Rotmams P (1986) Low-dose aspirin prevents pregnancy-induced hypertension and pre-eclampsia in angiotensin-sensitive primigravide. Lancet 1:1–3PubMedCrossRefGoogle Scholar
  18. WHO (2006) Summary of evaluations performed by the joint FAO/WHO expert committee on food additives, Eugenol No. 1529, WHO Food Additives Series 17, http://www.inchem.org/documents/jecfa/jecmono/v17je10.htm

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Jian-yong Li
    • 1
  • Yuan-guang Yu
    • 1
  • Qi-wen Wang
    • 1
  • Ji-yu Zhang
    • 1
  • Ya-jun Yang
    • 1
  • Bing Li
    • 1
  • Xu-zheng Zhou
    • 1
  • Jian-rong Niu
    • 1
  • Xiao-juan Wei
    • 1
  • Xi-wang Liu
    • 1
  • Zhi-qi Liu
    • 2
  1. 1.Key Lab of New Animal Drug Project of Gansu Province, Key Lab of Veterinary Pharmaceutics Discovery of Agricultural MinistryLanzhou Institute of Animal Science and Veterinary Pharmaceutics, Chinese Academy of Agricultural SciencesLanzhouChina
  2. 2.The Academy of Life Science and EngineeringLanzhou University of TechnologyLanzhouChina

Personalised recommendations