Skip to main content
SpringerLink
Log in

Oxidative coupling of cinnamic acid derivatives and their radical-scavenging activities

  • Article
  • Organic Chemistry
  • Published:
Chinese Science Bulletin

Abstract

4-Hydroxycinnamic acid derivatives, including ferulic acid (FA) (1), sinapic acid (SA) (2) and caffeic acid (CA) (3), are widely distributed in the plant kingdom, and undergo oxidative cross-coupling leading to the corresponding dehydrodimers, trimers and even higher oligomers in plants. In order to evaluate the antioxidative ability of these 4-hydroxycinnamic acid derivatives and their oligomers, we synthesized 8-8′-bis-lactone-dimers (8-8′-DiFA (4), 8-8′-DiSA (5) and 8-8′-DiCA (6)), as well as a new trimer (7), by the reaction of the corresponding monomers (1–3) with Ag2O in methanol, and assayed their free radical-scavenging activity by the reaction with 2,2-diphenyl-1-picrylhydrazyl radical (DPPH·). It was found that CA (3) and 8-8′-DiCA (6) bearing o-dihydroxyl groups exhibited significantly higher radical-scavenging activity than those bearing no such groups, and oxidative coupling of CA (3) resulted in remarkable enhancement in the activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Finkel T, Holbrook N J. Oxidants, oxidative stress and the biology of ageing. Nature, 2000, 408: 239–247

    Article  Google Scholar 

  2. Perwez H S, Hofseth L J, Harris C C. Radical cause of cancer. Nat Rev Cancer, 2003, 3: 276–285

    Article  Google Scholar 

  3. Cooke M S, Evans M D, Dizdaroglu M, et al. Oxidative DNA damage: Mechanism, mutation, and disease. FASEB J, 2003, 17: 1195–1214

    Article  Google Scholar 

  4. Surh Y J. Cancer chemoprevention with dietary phytochemicals. Nat Rev Cancer, 2003, 3: 768–780

    Article  Google Scholar 

  5. Brash D E, Harve P A. New careers for antioxidants. Proc Natl Acad Sci USA, 2002, 99: 13969–13971

    Article  Google Scholar 

  6. Rice-Evans C A, Diplock A T. Current status of antioxidant therapy. Free Radic Biol Med, 1993, 15: 77–96

    Article  Google Scholar 

  7. Zhou B, Liu Z L. Bioantioxidants: From chemistry to biology. Pure Appl Chem, 2005, 77: 1887–1903

    Article  Google Scholar 

  8. Robbins R J. Phenolic acids in foods: An overview of analytical methodology. J Agric Food Chem, 2003, 51: 2866–2887

    Article  Google Scholar 

  9. Castelluccio C, Paganga G, Melikian N, et al. Antioxidant potential of intermediates in phenylpropanoid metabolism in higher plants. FEBS Lett, 1995, 368: 188–192

    Article  Google Scholar 

  10. Nardini M, D’Aquino M, Tomassi G, et al. Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Radic Biol Med, 1995, 19: 541–552

    Article  Google Scholar 

  11. Firuzi O, Giansanti L, Vento R, et al. Hypochlorite scavenging activity of hydroxycinnamic acids evaluated by a rapid microplate method based on the measurement of chloramines. J Pharm Pharmacol, 2003, 55: 1021–1027

    Article  Google Scholar 

  12. Pannala A, Razaq R, Halliwell B, et al. Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: Nitration or electron donation? Free Radic Biol Med, 1998, 24: 594–606

    Article  Google Scholar 

  13. Chen J H, Ho C T. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J Agric Food Chem, 1997, 45: 2374–2378

    Article  Google Scholar 

  14. Zhou B, Miao Q, Yang L, et al. Antioxidative effects of flavonols and their glycosides against the free-radical-induced peroxidation of linoleic acid in solution and in micelles. Chem Eur J, 2005, 11: 680–691

    Article  Google Scholar 

  15. Zhou B, Wu L M, Yang L, et al. Evidence for α-tocopherol regeneration reaction of green tea polyphenols in SDS micelles. Free Radic Biol Med, 2005, 38: 78–84

    Article  Google Scholar 

  16. Chen W F, Deng S L, Zhou B, et al. Curcumin and its analogues as potent inhibitors of low density lipoprotein oxidation: H-atom abstraction from the phenolic groups and possible involvement of the 4-hydroxy-3-methoxyphenyl groups. Free Radic Biol Med, 2006, 40: 526–535

    Article  Google Scholar 

  17. Zheng L F, Wei Q Y, Cai Y J, et al. DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu (II) ions: Mechanism and structure-activity relationship. Free Radic Biol Med, 2006, 41: 1807–1816

    Article  Google Scholar 

  18. Qian Y P, Cai Y J, Fan G J, et al. Antioxidant-based lead discovery for cancer chemoprevention: The case of resveratrol. J Med Chem, 2009, 52: 1963–1974

    Article  Google Scholar 

  19. Shang Y J, Qian Y P, Liu X D, et al. Radical-scavenging activity and mechanism of resveratrol-oriented analogues: Influence of the solvent, radical and substitution. J Org Chem, 2009, 74: 5025–5031

    Article  Google Scholar 

  20. Fang J G, Zhou B. Structure-activity relationship and mechanism of the tocopherol-regenerating activity of resveratrol and its analogues. J Agric Food Chem, 2008, 56: 11458–11463

    Article  Google Scholar 

  21. Cheng J C, Dai F, Zhou B, et al. Antioxidative activity of hydroxycinnamic acid derivatives in human low density lipoprotein: Mechanism and structure-activity relationship. Food Chem, 2007, 104: 132–139

    Article  Google Scholar 

  22. Bunzel M, Ralph J, Funk C, et al. Structural elucidation of new ferulic acid-containing phenolic dimers and trimers isolated from maize bran. Tetrahedron Lett, 2005, 46: 5845–5850

    Article  Google Scholar 

  23. Funk C, Ralph J, Steinhart H, et al. Isolation and structural characterization of 8-O-4/8-O-4- and 8-8/8-O-4-coupled dehydrotriferulic acids from maize bran. Phytochemistry, 2005, 66: 363–371

    Article  Google Scholar 

  24. Bunzel M, Ralph J, Bruening P, et al. Structural identification of dehydrotriferulic and dehydrotetraferulic acids isolated from insoluble maize bran fiber. J Agric Food Chem, 2006, 54: 6409–6418

    Article  Google Scholar 

  25. Tanaka T, Nishimura A, Kouno I, et al. Isolation and characterization of yunnaneic acids A-D, four novel caffeic acid metabolites from Salvia yunnanensis. J Nat Prod, 1996, 59: 843–849

    Article  Google Scholar 

  26. Tanaka T, Nishimura A, Kouno I, et al. Four new caffeic acid metabolites, yunnaneic acids E-H, from Salvia yunnanensis. Chem Pharm Bull, 1997, 45: 1596–1600

    Google Scholar 

  27. Cano A, Arnao M B, Williamson G, et al. Superoxide scavenging by polyphenols: Effect of conjugation and dimerization. Redox Rep, 2002, 7: 379–383

    Article  Google Scholar 

  28. Cartwright N J, Haworth R D. Constituents of natural phenolic resins. XIX. Oxidation of ferulic acid. J Chem Soc, 1944, 535–537

  29. Kumada Y, Takeuchi T, Umezawa H. Characterization of the dehydrodicaffeic acid dilactone-forming enzyme and the enzymic and chemical synthesis of this mushroom product. Agric Biol Chem, 1977, 41: 877–885

    Google Scholar 

  30. Sako M, Hosokawa H, Ito T, et al. Regioselective oxidative coupling of 4-hydroxystilbenes: Synthesis of resveratrol and ɛ-viniferin (E)-dehydrodimers. J Org Chem, 2004, 69: 2598–2600

    Article  Google Scholar 

  31. West K F, Moore H W. An unusual oxidative dimerization of 2-(vinyloxy)phenols. J Org Chem, 1984, 49: 2809–2812

    Article  Google Scholar 

  32. Liu H L, Kong L Y, Takaya Y, et al. Biotransformation of ferulic acid into two new dihydrotrimers by Momordica charantia peroxidase. Chem Pharm Bull, 2005, 53: 816–819

    Article  Google Scholar 

  33. Ward G, Hadar Y, Bilkis I, et al. Initial steps of ferulic acid polymerization by lignin peroxidase. J Biol Chem, 2001, 276: 18734–18741

    Article  Google Scholar 

  34. Taylor E C, Andrade J G, Rall G J H, et al. Thallium in organic synthesis. 60. 2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octane-4,8-dione lignans by oxidative dimerization of 4-alkoxycinnamic acids with thallium (III) trifluoroacetate or cobalt(III) trifluoride. J Org Chem, 1981, 46: 3078–3081

    Article  Google Scholar 

  35. Tazaki H, Taguchi D, Hayashida T, et al. Stable isotope-labeling studies on the oxidative coupling of caffeic acid via o-quinone. Biosci Biotechnol Biochem, 2001, 65: 2613–2621

    Article  Google Scholar 

  36. Goupy P, Dufour C, Loonis M, et al. Quantitative kinetic analysis of hydrogen transfer reactions from dietary polyphenols to the DPPH radical. J Agric Food Chem, 2003, 51: 615–622

    Article  Google Scholar 

  37. Foti M, Ruberto G. Kinetic solvent effects on phenolic antioxidant determined by spectrophotometric measurements. J Agric Food Chem, 2001, 49: 342–348

    Article  Google Scholar 

  38. Wright J S, Johnson E R, Dilabio G A. Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidant. J Amer Chem Soc, 2001, 123: 1173–1183

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, China

    XiaoLing Jin, RuTing Yang, YaJing Shang, Fang Dai, YiPing Qian, LiXia Cheng, Bo Zhou & ZhongLi Liu

Authors
  1. XiaoLing Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. RuTing Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. YaJing Shang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Fang Dai
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. YiPing Qian
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. LiXia Cheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Bo Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. ZhongLi Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Bo Zhou or ZhongLi Liu.

About this article

Cite this article

Jin, X., Yang, R., Shang, Y. et al. Oxidative coupling of cinnamic acid derivatives and their radical-scavenging activities. Chin. Sci. Bull. 55, 2885–2890 (2010). https://doi.org/10.1007/s11434-010-3064-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11434-010-3064-0

Keywords

Search

Navigation