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Antioxidant and Antiproliferative Activity of Diospyros lotus L. Extract and Isolated Compounds

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Abstract

The object of the study was to determine the chemical composition of Diospyros lotus L. extract and their antioxidant and antiproliferative properties. Eight compounds were isolated from D. lotus and identified as gallic acid, methylgallate, ellagic acid, kaempferol, quercetin, myricetin, myricetin 3-O-β-glucuronide, and myricetin-3-O-α-rhamnoside. D. lotus extract tested in different in vitro systems (DPPH, ABTS, FRAP, and Fe2+ chelating activity assay) showed significant antioxidant activity. The potential antiproliferative properties of D. lotus extract and isolated compounds against nine human cancer cell lines such as COR-L23, CaCo-2, C32, ACHN, A375, A549, Huh-7D12, MCF-7, and LNCaP were investigated in vitro by SRB assay. D. lotus extract demonstrated the highest inhibitory activity against COR-L23 with an IC50 value of 12.2 μg/ml. Among identified hydrolysable tannins, ellagic acid evidenced strong antiproliferative activity against both C32 and A375 cells with IC50 values of 0.8 and 4.1 μg/ml, respectively. Interesting results were observed, also, with gallic acid that showed the highest cytotoxic activity against CaCo-2 (IC50 2.6 μg/ml). Overall, the results of this study suggest that D. lotus displays a good antioxidant activity and has antiproliferative effects. Both activities are related to identified phenolic compounds.

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Abbreviations

ABTS:

2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

FRAP:

Ferric Reducing Ability Power

ROS:

Reactive oxygen species

SRB:

Sulforhodamine B

TEAC:

Trolox Equivalent Antioxidant Capacity

References

  1. Halliwell B, Gutteridge JMC (1990) Role of free radicals and catalitic metal ions in human disease: an overview. Met Enzymol 186:1–85

    Article  CAS  Google Scholar 

  2. Panayiotidis M (2008) Reactive oxygen species (ROS) in multistage carcinogenesis. Cancer Lett 266:3–6

    Article  CAS  Google Scholar 

  3. Ferlay J, Autier P, Boniol M, Heanue M, Colombet M, Boyle P (2007) Estimates of the cancer incidence and mortality in Europe in 2006. Ann Oncol 18:581–592

    Article  CAS  Google Scholar 

  4. Newman DJ, Cragg GM (2007) Natural products as sources of new drugs over the last 25 years. J Nat Prod 70:461–477

    Article  CAS  Google Scholar 

  5. Butler MS (2008) Natural products to drugs: natural product-derived compounds in clinical trials. Nat Prod Rep 25:475–516

    Article  CAS  Google Scholar 

  6. Feher M, Schmidt JM (2003) Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry. J Chem Inf Comput Sci 43:218–227

    CAS  Google Scholar 

  7. Ortholand JY, Ganesan A (2004) Natural products and combinatorial chemistry- back to the future. Curr Opin Chem Biol 8:271–280

    Article  CAS  Google Scholar 

  8. Martínez-Rocha A, Puga R, Hernández-Sandoval L, Loarca-Piña G, Mendoza S (2008) Antioxidant and antimutagenic activities of Mexican oregano (Lippia graveolens Kunth). Plant Foods Hum Nutr 63:1–5

    Article  Google Scholar 

  9. Aparicio-Fernández X, Reynoso-Camacho R, Castaño-Tostado E, García-Gasca T, González de Mejía E, Guzmán-Maldonado SH, Elizondo G, Yousef GG, Lila MA, Loarca-Pina G (2008) Antiradical capacity and induction of apoptosis on HeLa cells by a Phaseolus vulgaris extract. Plant Foods Hum Nutr 63:35–40

    Article  Google Scholar 

  10. Ahmet FA, Kadioglu A (1998) Non volatile acid composition during fruit development of Diospyros lotus L. Turk J Bot 22:69–72

    Google Scholar 

  11. Ayaz FA, Kadioglu A, Hayirlioglu S (1995) Determination of some mono- and disaccharides in the fruits of Diospyros lotus L. using gas chromatography. Tr J Bot 19:493–495

    Google Scholar 

  12. Ayaz FA, Kadioglu A (1999) Fatty acid compositional changes in developing Persimmon (Diospyros lotus L.) fruit. New Zealand J Crop Hort Sci 27:257–261

    CAS  Google Scholar 

  13. Lee BB, Cha MR, Kim SY, Park E, Park HM, Lee SC (2007) Antioxidative and anticancer activity of extracts of cherry (Prunus serratula var. spontanea) blossoms. Plant Food Hum Nutr 62:79–84

    Article  CAS  Google Scholar 

  14. Benzie IF, Strains JJ (1996) The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Anal Biochem 239:70–76

    Article  CAS  Google Scholar 

  15. Dinis CP, Madeira VMC, Almeida LM (1994) Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Ach Biochem Biophys 315:161–169

    Article  CAS  Google Scholar 

  16. Chohan M, Forster-Wilkins G, Opara EI (2008) Determination of the antioxidant capacity of culinary herbs subjected to various cooking and storage processes using the ABTS(*+) radical cation assay. Plant Foods Hum Nutr 63:47–52

    Article  CAS  Google Scholar 

  17. Loizzo MR, Tundis R, Statti GA, Menichini F, Houghton PJ (2005) In vitro antiproliferative effects on human tumour cell lines of extracts and jacaranone from Senecio leucanthemifolius Poiret. J Pharm Pharmacol 57:897–901

    Article  CAS  Google Scholar 

  18. Foo LY (1993) Amarin, an di-dehydrohexahydroxydiphenol hydrolysable tannin from Phyllantus amarus. Phytochemistry 33:487–491

    Article  CAS  Google Scholar 

  19. Nawar MAM, Hussein SAM, Merfort I (1994) NMR spectral analysis of polyphenolics from Punica granatum. Phytochemistry 36:793–798

    Article  Google Scholar 

  20. Harborne JB, Mabry TJ (1982) The flavonoids: advances in research. Chapman and Hall, London, pp 24–132

    Google Scholar 

  21. Hong Y, Lin S, Jiang Y, Ashraf M (2008) Variation in contents of total phenolics and flavonoids and antioxidant activities in the leaves of 11 Eriobotrya species. Plant Foods Hum Nutr 63:200–204

    Article  CAS  Google Scholar 

  22. Rice-Evans CA, Miller NT, Paganga G (1997) Antioxidant properties of phenolic compounds. Trends Plant Sci 4:304–309

    Google Scholar 

  23. Scambia G, Panici PB, Ranelletti FO, Ferrandina G, De Vincenzo R, Piantelli M, Masciullo V, Bonanno G, Isola G, Mancuso S (1994) Quercetin enhances transforming growth factor beta 1 secretion by human ovarian cancer cells. Int J Cancer 57:211–215

    Article  CAS  Google Scholar 

  24. Agullo G, Gamet L, Besson C, Demigne C, Remesy C (1994) Quercetin exerts a preferential cytotoxic effect on active dividing colon carcinoma HT29 and CaCO2 cells. Cancer Lett 87:55–63

    Article  CAS  Google Scholar 

  25. Plaumann B, Fritsche M, Rimpler H, Brandner G, Hess RD (1996) Flavonoids activate wild type p53. Oncogene 13:1605–1614

    CAS  Google Scholar 

  26. Csokay B, Pradja N, Weber G, Olah E (1997) Molecular mechanisms in the antiproliferative action of quercetin. Life Sci 60:2157–2163

    Article  CAS  Google Scholar 

  27. Narayanan BA, Geoffroy O, Willingham MC, Re GG, Nixon DW (1999) p53/p21 WAF1/CIP1 expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells. Cancer Lett 136:215–221

    Article  CAS  Google Scholar 

  28. Uddin S, Choudhry MA (1995) Quercetin, a bioflavonoid, inhibits the DNA synthesis of human leukemia cells. Biochem Mol Biol Int 36:545–550

    CAS  Google Scholar 

  29. Verma AK, Johnson JA, Gould MN, Tanner MA (1988) Inhibition of induced rat mammary cancer by dietary flavonol quercetin. Cancer Res 48:5754–5758

    CAS  Google Scholar 

  30. Khanduja KL, Gandhi RK, Pathania V, Syal N (1999) Prevention of nitrosodiethylamine-induced lung tumorigenesis by ellagic acid and quercetin in mice. Food Chem Toxicol 37:313–318

    Article  CAS  Google Scholar 

  31. Maas JL, Galletta GJ, Stoner GD (1991) Ellagic acid, an anticarcinogen in fruits, especially in strawberries: a review. Hort Sci 26:10–14

    Google Scholar 

  32. Han DH, Lee MJ, Kim JH (2006) Antioxidant and apoptosis-inducing activities of ellagic acid. Anticancer Res 26:3601–3606

    CAS  Google Scholar 

  33. Kuo SM (1996) Antiproliferative potency of structurally distinct dietary flavonoids on human colon cancer cells. Cancer Lett 110:41–48

    Article  CAS  Google Scholar 

  34. Elangovan V, Sekar N, Govindasamy S (1994) Chemopreventive potential of dietary bioflavonoids against 20-methylcholanthrene-induced tumorigenesis. Cancer Lett 87:107–113

    Article  CAS  Google Scholar 

  35. Duthie GG, Duthie SJ, Kyle JA (2000) Plant polyphenols in cancer and heart disease: implications as nutritional antioxidants. Nutr Res Rev 13:79–106

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors are grateful to Dr. V. Filippelli, Faculty of Pharmacy, Nutrition and Health Science, University of Calabria, for English revision of the manuscript.

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Authors and Affiliations

  1. Department of Pharmaceutical Sciences, Faculty of Pharmacy, Nutrition and Health Sciences, University of Calabria, 87036, Rende, CS, Italy

    Monica Rosa Loizzo, Rosa Tundis, Federica Menichini & Francesco Menichini

  2. Pharmacognosy Department, National Research Centre, Dokki, Giza, Egypt

    Ataa Said & Khaled Rashed

  3. Phytochemistry and Plant Systematic Department, National Research Centre, Dokki, Giza, Egypt

    Usama W. Hawas

  4. Department of Food Science, Politecnica delle Marche University, via Brecce Bianche, 60131, Ancona, Italy

    Natale Giuseppe Frega

Authors
  1. Monica Rosa Loizzo
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  2. Ataa Said
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  3. Rosa Tundis
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  4. Usama W. Hawas
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  5. Khaled Rashed
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  6. Federica Menichini
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  7. Natale Giuseppe Frega
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  8. Francesco Menichini
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Correspondence to Monica Rosa Loizzo.

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Loizzo, M.R., Said, A., Tundis, R. et al. Antioxidant and Antiproliferative Activity of Diospyros lotus L. Extract and Isolated Compounds. Plant Foods Hum Nutr 64, 264–270 (2009). https://doi.org/10.1007/s11130-009-0133-0

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  • DOI: https://doi.org/10.1007/s11130-009-0133-0

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