Cytotoxic property of ultraviolet-induced rice phytoalexins to human colon carcinoma HCT-116 cells

  • Jong-Hwa Park
  • Yuan-Yuan Fu
  • In Sik Chung
  • Tae-Ryong Hahn
  • Man-Ho Cho
Short Communication

Abstract

Exposure to ultraviolet (UV) radiation increased the cytotoxic effect of rice leaf extract on human colon carcinoma HCT-116 cells, suggesting that the production of cytotoxic compounds in rice leaves are induced by UV treatment. To identify cytotoxic agents in UV-treated rice leaves, the phenolic compound peaks prominently increased by UV treatment were isolated using reversed phase high performance liquid chromatography (HPLC). The isolated compounds were identified as N-trans-cinnamoyltyramine, N-benzoyltryptamine, and sakuranetin using NMR and mass spectrometric techniques. N-Benzoyltryptamine and sakuranetin were previously reported as rice phytoalexins, and N-trans-cinnamoyltyramine was first isolated from rice. N-Benzoyltryptamine and sakuranetin were found to inhibit the growth of HCT-116 cells with IC50 values of 89.2±4.8 and 68.8±5.2 μg/mL, respectively, indicating that these phytoalexins are cytotoxic agents in the UV-treated rice leaves. These results suggest that rice phytoalexins are potent anti-cancer agents and UV-treated rice leaves are valuable source for therapeutic agents.

Keywords

anti-cancer property N-benzoyltryptamine N-trans-cinnamoyltyramine rice phytoalexin sakuranetin ultraviolet radiation 

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References

  1. Ahuja I, Kissen R, and Bones AM (2012) Phytoalexins in defense against pathogens. Trends Plant Sci 17, 73–90.CrossRefGoogle Scholar
  2. Anunciato TP and da Rocha Filho PA (2012) Carotenoids and polyphenols in nutricosmetics, nutraceuticals, and cosmeceuticals. J Cosmet Dermatol 11, 51–54.CrossRefGoogle Scholar
  3. Boue SM, Cleveland TE, Carter-Wientjes C, Shih BY, Bhatnagar D, McLachlan JM et al. (2009) Phytoalexin-enriched functional foods. J Agric Food Chem 57, 2614–2622.CrossRefGoogle Scholar
  4. Buer CS, Imin N, and Djordjevic MA (2010) Flavonoids: new roles for old molecules. J Integr Plant Biol 52, 98–111.CrossRefGoogle Scholar
  5. Cartwright D, Langcake P, Pryce RJ, Leworthy DP, and Ride JP (1977) Chemical activation of host defense mechanisms as a basis for crop protection. Nature 267, 511–513.CrossRefGoogle Scholar
  6. Cartwright DW, Langcake P, Pryce RJ, Leworthy DP, and Ride JP (1981) Isolation and characterization of two phytoalexins from rice as momilactones A and B. Phytochemistry 20, 535–537.CrossRefGoogle Scholar
  7. Daniel O, Meier MS, Schlatter J, and Frischknecht P (1999) Selected phenolic compounds in cultivated plants: ecologic functions, health implications, and modulation by pesticides. Environ Health Perspect 107, 109–114.Google Scholar
  8. Dewanto V, Wu X, Adom KK, and Liu RH (2002) Thermal processing enhances the nutritional value of tomatoes by increasing total antioxidant activity. J Agric Food Chem 50, 3010–3014.CrossRefGoogle Scholar
  9. Freitas MO, Ponte FA, Lima MAS, and Silveira ER (2008) Flavonoids and triterpenes from the nest of the stingless bee Trigona spinipes. J Braz Chem Soc 19, 532–535.CrossRefGoogle Scholar
  10. Hifnawy MS, Vaquette J, Sévenet T, Pousset JL, and Cavé A (1977) Produits neutres et alcaloides de Myrtopsis macrocarpa, M. myrtoidea, M. novaecaledoniae et M. sellingii. Phytochemistry 16, 1035–1039.CrossRefGoogle Scholar
  11. Ho BT, An R, Noel MB, and Tansey LW (1971) Central nervous system depressive activity of some amides of tryptamine. J Med Chem 14, 553–554.CrossRefGoogle Scholar
  12. Ibrahim AR, Galal AM, Ahmed MS, and Mossa GS (2003) O-Demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans. Chem Pharm Bull 51, 203–206.CrossRefGoogle Scholar
  13. Kato H, Kodama O, and Akatsuka T (1994) Oryzalexin F, a diterpene phytoalexin from UV-irradiated rice leaves. Phytochemistry 36, 299–301.CrossRefGoogle Scholar
  14. Kodama O, Miyakawa J, Akatsuka T, and Kiyosawa S (1992) Sakuranetin, a flavanone phytoalexin from ultraviolet-irradiated rice leaves. Phytochemistry 31, 3807–3809.CrossRefGoogle Scholar
  15. Kodama O, Suzuki T, Miyakawa J, and Akatsuka T (1988) Ultravioletinduced accumulation of phytoalexins in rice leaves. Agric Biol Chem 52, 2469–2473.CrossRefGoogle Scholar
  16. Ogawa Y, Oku H, Iwaoka E, Iinuma M, and Ishiguro K (2007) Allergypreventive flavonoids from Xanthorrhoea hastilis. Chem Pharm Bull 55, 675–678.CrossRefGoogle Scholar
  17. Okada A, Shimizu T, Okada K, Kuzuyama T, Koga J, Shibuya N et al. (2007) Elicitor induced activation of the methylerythritol phosphate pathway toward phytoalexins biosynthesis in rice. Plant Mol Biol 65, 177–187.CrossRefGoogle Scholar
  18. Peng Y, Hao X, Fan J, Zhou L, Zuo G, and Wang B (2002) (China Agriculture Univ. Peop. Rep. China) Preparation of acyltryptamine phytoalexins as fungicides. Chinese Patent CN 1365971 A, 2002.Google Scholar
  19. Peters RJ (2006) Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants. Phytochemistry 67, 2307–2317.CrossRefGoogle Scholar
  20. Roangnolo DF, Davis CD, and Milner JA (2012) Phytoalexins in cancer prevention. Front Biosci 17, 2035–2058.CrossRefGoogle Scholar
  21. Saito T, Abe D, and Sekiya K (2008) Sakuranetin induces adipogenesis of 3T3-L1 cells through enhanced expression of PPARγ2. Biochem Biophys Res Commun 372, 835–839.CrossRefGoogle Scholar
  22. Taiz L and Zeiger E (2006) Secondary metabolites and plant defense. In Plant Physiology, Taiz L and Zeiger E (4th ed.), pp. 315–344, Sinauer Associates, Inc., USA.Google Scholar
  23. Winkel-Shirley B (2002) Biosynthesis of flavonoids and effects of stress. Curr Opin Plant Biol 5, 218–223.CrossRefGoogle Scholar
  24. Yang Y, Song ZG, and Liu ZQ (2011) Synthesis and antioxidant capacities of hydroxyl derivatives of cinnamoylphenethylamine in protecting DNA and scavenging radicals. Free Radic Res 45, 445–453.CrossRefGoogle Scholar
  25. Yoo KH, Park JH, Cui EJ, Kim KI, Kim JY, Kim J et al. (2012) 3-OAcetyloleanolic acid induces apoptosis in human colon carcinoma HCT-116 cells. Phytother Res 26, 1541–1546.CrossRefGoogle Scholar
  26. Zhang L, Kong Y, Wu D, Zhang H, Wu J, Chen J et al. (2008) Three flavonoids targeting the β-hydroxyacyl-acyl carrier protein dehydratase from Helicobacter pylori: crystal structure characterization with enzymatic inhibition assay. Protein Sci 17, 1971–1978.CrossRefGoogle Scholar
  27. Zhang WJ and Björn LO (2009) The effect of ultraviolet radiation on the accumulation of medicinal compounds in plants. Fitoterapia 80, 207–218.CrossRefGoogle Scholar

Copyright information

© The Korean Society for Applied Biological Chemistry 2013

Authors and Affiliations

  • Jong-Hwa Park
    • 1
  • Yuan-Yuan Fu
    • 1
  • In Sik Chung
    • 1
  • Tae-Ryong Hahn
    • 1
  • Man-Ho Cho
    • 1
  1. 1.Graduate School of Biotechnology and Plant Metabolism Research CenterKyung Hee UniversityYonginRepublic of Korea

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