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Antioxidant and cytotoxic activities of naphthalene derivatives from Diospyros kaki
Journal of Wood Science volume 57, pages 161–165 (2011)
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
George AP, Redpath S (2008) Health and medicinal benefits of persimmon fruit: a review. Adv Hort Sci 22:244–249
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
Sankaram AVB, Sidhu GS (1971) A new naphthaldehyde from the heartwood of Diospyros melanoxylon. Phytochemistry 10:458–459
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
Ganapaty S, Thomas PS, Karagianis G, Waterman PG, Brun R (2006) Antiprotozoal and cytotoxic naphthalene derivatives from Diospyros assimilis. Phytochemistry 67:1950–1956
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
Matsushita Y, Jang IC, Imai T, Fukushima K, Lee SC (2010) Naphthalene derivatives from Diospyros kaki. J Wood Sci 56:418–421
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
Muller HE (1985) Detection of hydrogen peroxide produced by microorganism on ABTS-peroxidase medium. Zentralbl Bakteriol Mikrobiol Hyg 259:151–158
Oyaizu M (1986) Antiangiogenic properties of natural polyphenols from red wine and green tea. Jpn J Nutr 44:307–315
Brand-Williams W, Cuvelier ME, Berset C (1995) Use of a free radical method to evaluate antioxidant activity. Lebensm-Wiss Technol 28:25–30
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
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
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
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
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
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
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
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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
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DOI: https://doi.org/10.1007/s10086-010-1147-9