Compendium of Inflammatory Diseases

2016 Edition
| Editors: Michael J. Parnham

Flavonoids as Anti-inflammatory Agents

Reference work entry
DOI: https://doi.org/10.1007/978-3-7643-8550-7_19

Synonyms

Bioflavonoids; Flavonoids; Phenylchromones; Vitamin P

Definition

The flavonoids are a group of plant secondary metabolites biosynthetically derived from shikimic acid and polyketide pathways. They are plant pigments containing benzopyrone substituted with a phenyl ring at position 2 or 3 and possess a wide spectrum of biological activities, including antioxidant and anti-inflammatory activities.

Chemical Structures and Properties

The technical term “flavonoid” arises from the basic skeleton of these plant pigments that are derived from benzo-γ-pyrone, structure well known as chromone, modified at position 2 or 3 by the addition of a phenyl ring at position 2 yielding a flavonoid and at position 3 an isoflavonoid (Fig. 1). The biosynthesis of flavonoids is based on the crossing of shikimic acid and acylphloroglucinol metabolic pathways. The three-ring skeleton may be substituted with hydroxyl groups. Substitution of the A ring typically occurs at positions 5 and 7 (a meta...
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References

  1. Bruneton, J. (1999). Pharmacognosy, phytochemistry, medicinal plants. Lavoisier, Paris, France.Google Scholar
  2. Costa, G., Francisco, V., Lopes, M. C., Cruz, M. T., & Batista, M. T. (2012). Intracellular signaling pathways modulated by phenolic compounds: Application for new anti-inflammatory drugs discovery. Current Medicinal Chemistry, 19, 2876–2900.CrossRefPubMedGoogle Scholar
  3. Crozier, A., Del Rio, D., & Clifford, M. N. (2010). Bioavailability of dietary flavonoids and phenolic compounds. Molecular Aspects of Medicine, 31, 446–467.CrossRefPubMedGoogle Scholar
  4. de Pascual-Teresa, S., Moreno, D. A., & García-Viguera, C. (2010). Flavanols and anthocyanins in cardiovascular health: A review of current evidence. International Journal of Molecular Science, 11, 1679–1703.CrossRefGoogle Scholar
  5. Del Rio, D., Rodriguez-Mateos, A., Spencer, J. P. E., Tognolini, M., Borges, G., & Crozier, A. (2013). Dietary (poly)phenolics in human health: Structures, bioavailability, and evidence of protective effects again chronic diseases. Antioxidants & Redox Signaling, 18, 1818–1892.CrossRefGoogle Scholar
  6. Dolton, M. J., Roufogalis, B. D., & McLachlan, A. J. (2012). Fruit juices as perpetrators of drug interactions: The role of organic anion-transporting polypeptides. Clinical Pharmacology & Therapeutics, 92, 622–630.CrossRefGoogle Scholar
  7. Egert, S., & Rimbach, G. (2011). Which sources of flavonoids: Complex diets or dietary supplements? Advances in Nutrition, 2. doi:10.3945/an.110.000026.Google Scholar
  8. García-Lafuente, A., Guillamón, E., Villares, A., Rostagno, M. A., & Martínez, J. A. (2009). Flavonoids as anti-inflammatory agents: Implications in cancer and cardiovascular disease. Inflammation Research, 58, 537–552.CrossRefPubMedGoogle Scholar
  9. Hamer, M., & Steptoe, A. (2006). Influence of specific nutrients on progression of atherosclerosis, vascular function, haemostasis and inflammation in coronary heart disease patients: A systematic review. British Journal of Nutrition, 95, 849–859.CrossRefPubMedGoogle Scholar
  10. Havsteen, B. H. (2002). The biochemistry and medical significance of the flavonoids. Pharmacology & Therapeutics, 96, 67–202.CrossRefGoogle Scholar
  11. Izzi, V., Masuelli, l., Tresoldi, I., Sacchetti, P., Modesti, A., Galvano, F., et al. (2012). The effects of dietary flavonoids on the regulation of redox inflammatory networks. Frontiers in Bioscience, 17, 2396–2418.CrossRefGoogle Scholar
  12. Kim, P. K., Son, K. H., Chang, H. W., & Kang, S. S. (2004). Anti-inflammatory plant flavonoids and cellular action mechanisms. Journal of Pharmacological Sciences, 96, 229–245.CrossRefPubMedGoogle Scholar
  13. Peterson, J., & Dwyer, J. (1998). Flavonoids: Dietary occurrence and biochemical activity. Nutrition Research, 18, 1995–2018.Google Scholar
  14. Pietta, P. G. (2000). Flavonoids as antioxidants. Journal of Natural Products, 63, 1035–1042.CrossRefPubMedGoogle Scholar
  15. Procházková, D., Boušová, I., & Wilhelmová, N. (2011). Antioxidant and prooxidant properties of flavonoids. Fitoterapia, 82, 513–523.CrossRefPubMedGoogle Scholar
  16. Seden, K., Dickinson, L., Khoo, S., & Back, D. (2010). Grapefruit-drug interactions. Drugs, 70, 2373–2407.CrossRefPubMedGoogle Scholar
  17. Skibola, C. F., & Smith, M. T. (2000). Potential health impacts of excessive flavonoid intake. Free Radical Biology and Medicine, 29, 375–383.CrossRefPubMedGoogle Scholar
  18. Smejkal, K. (2014). Cytotoxic potential of C-prenylated flavonoids. Phytochemistry Reviews, 13, 245–275.CrossRefGoogle Scholar
  19. Srinivas, N. R. (2013). Is pomegranate juice a potential perpetrator of clinical drug-drug interactions? Review of the in vitro, preclinical and clinical evidence. European Journal of Drug Metabolism and Pharmacokinetics, 38, 223–229.CrossRefPubMedGoogle Scholar
  20. Thilakarathna, S. H., & Rupasinghe, H. P. V. (2013). Flavonoids bioavailability and attempts for bioavailability enhancement. Nutrients, 5, 3367–3387.CrossRefPubMedPubMedCentralGoogle Scholar
  21. Yazaki, K., Sasaki, K., & Tsurumaru, Y. (2009). Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry, 70, 1739–1745.CrossRefPubMedGoogle Scholar

Copyright information

© Springer International Publishing AG 2016

Authors and Affiliations

  1. 1.Department of Molecular Biology and Pharmaceutical Biotechnology, Faculty of PharmacyUniversity of Veterinary and Pharmaceutical Sciences BrnoBrnoCzech Republic
  2. 2.Department of Natural Drugs, Faculty of PharmacyUniversity of Veterinary and Pharmaceutical Sciences BrnoBrnoCzech Republic