Skip to main content

Official Journal of the Japan Wood Research Society

Antioxidant and cytotoxic activities of naphthalene derivatives from Diospyros kaki

Abstract

4,8-Dihydroxy-5-methoxy-2-naphthaldehyde (Compound I) was isolated from blackened heartwood of Diospyros kaki and was methylated with diazomethane. Antioxidant and cytotoxic activities of Compound I and two methylated derivatives [4-hydroxy-5,8-dimethoxy-2-(2-oxopropyl)-naphthalene (D-1) and 2-glycidyl-4-hydroxy-5,8-dimethoxy naphthalene (D-2)] were evaluated. Compound I showed higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and reducing power than D-1 and D-2. However, D-1 and D-2 exhibited slightly stronger 2,2-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid)+ (ABTS+) radical scavenging activity than Compound I. Compound I also exhibited stronger cytotoxic activity than D-1 and D-2 against the growth of HT-29 colon cancer cells. The results supported the hypothesis that methylation of naphthalene derivatives slightly increased ABTS+ radical scavenging activity, but significantly decreased DPPH radical scavenging activity, reducing power, and cytotoxic activity.

References

  1. George AP, Redpath S (2008) Health and medicinal benefits of persimmon fruit: a review. Adv Hort Sci 22:244–249

    Google Scholar 

  2. Harper SH, Kemp AD, Tannock J (1970) Methoxynaphthaldehydes as constituents of the heartwood of Diospyros quiloensis and their synthesis by the Stobbe condensation. J Chem Soc C 1970:626–636

    Article  Google Scholar 

  3. Sankaram AVB, Sidhu GS (1971) A new naphthaldehyde from the heartwood of Diospyros melanoxylon. Phytochemistry 10:458–459

    Article  CAS  Google Scholar 

  4. Ito Y, Hayashi Y, Kato A (1995) Antifungal compounds from trees of the genus Diospyros with complete assignment of nuclear magnetic resonance data. Mokuzai Gakkaishi 41:694–698

    CAS  Google Scholar 

  5. Ganapaty S, Thomas PS, Karagianis G, Waterman PG, Brun R (2006) Antiprotozoal and cytotoxic naphthalene derivatives from Diospyros assimilis. Phytochemistry 67:1950–1956

    Article  PubMed  CAS  Google Scholar 

  6. Noda E, Aoki T, Minato K (2002) Physical and chemical characteristics of the blackened portion of Japanese persimmon (Diospyros kaki). J Wood Sci 48:245–249

    Article  CAS  Google Scholar 

  7. Matsushita Y, Jang IC, Imai T, Fukushima K, Lee SC (2010) Naphthalene derivatives from Diospyros kaki. J Wood Sci 56:418–421

    Article  CAS  Google Scholar 

  8. Lee SC, Kim JH, Jeong SM, Kim DR, Ha JU, Nam KC, Ahn DU (2003) Effect of far-infrared radiation on the antioxidant activity of rice hulls. J Agric Food Chem 51:4400–4403

    Article  PubMed  CAS  Google Scholar 

  9. Muller HE (1985) Detection of hydrogen peroxide produced by microorganism on ABTS-peroxidase medium. Zentralbl Bakteriol Mikrobiol Hyg 259:151–158

    CAS  Google Scholar 

  10. Oyaizu M (1986) Antiangiogenic properties of natural polyphenols from red wine and green tea. Jpn J Nutr 44:307–315

    CAS  Google Scholar 

  11. Brand-Williams W, Cuvelier ME, Berset C (1995) Use of a free radical method to evaluate antioxidant activity. Lebensm-Wiss Technol 28:25–30

    CAS  Google Scholar 

  12. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evan C (1999) Antioxidant activity applying improved ABTS radical cation decolorization assay. Free Radical Res 26:1231–1237

    CAS  Google Scholar 

  13. Nicoletta P, Roberta R, Min Y, Catherine RE (1999). Screening of dietary carotenoids and carotenoid-rich fruit extracts for antioxidant activities applying 2,2’-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) radical cation decolorization assay. Method Enzymol 299:379–389

    Article  Google Scholar 

  14. Yu L, Haley S, Perret J, Harris M, Wilson J, Qian M (2002) Free radical scavenging properties of wheat extracts. J Agric Food Chem 50:1619–1624

    Article  PubMed  CAS  Google Scholar 

  15. Wang M, Li J, Rangarajan M, Shao Y, La Voie EJ, Huang TC, Ho CT (1998) Antioxidative phenolic compounds from Sage (Salvia officinalis). J Agric Food Chem 46:4869–4873

    Article  CAS  Google Scholar 

  16. Shimada K, Fujikawa K, Yahara K, Nakamura T (1992) Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion. J Agric Food Chem 36:459–469

    Google Scholar 

  17. Li N, Liu JH, Zhang J, Yu BY (2008) Comparative evaluation of cytotoxicity and antioxidative activity of 20 flavonoids. J Agric Food Chem 56:3876–3883

    Article  PubMed  CAS  Google Scholar 

  18. Lee YT, Don MJ, Hung PS, Shen YC, Lo YS, Chang KW, Chen CF, Ho LK (2005) Cytotoxicity of phenolic acid phenethyl esters on oral cancer cells. Cancer Lett 223:19–25

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Seung-Cheol Lee.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Matsushita, Y., Jang, IC., Imai, T. et al. Antioxidant and cytotoxic activities of naphthalene derivatives from Diospyros kaki . J Wood Sci 57, 161–165 (2011). https://doi.org/10.1007/s10086-010-1147-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10086-010-1147-9

Key words

  • Naphthalene derivatives
  • Persimmon wood
  • Antioxidant activity
  • Cytotoxic activity