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Antioxidant and inhibitory activities of thioflavanones against nitric oxide production

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Abstract

The antioxidant and suppressive activities of thioflavanone derivatives against production of nitric oxide were investigated. Thioflavanone derivatives were prepared with methoxy, methyl, nitro, hydroxyl, chloro, and fluoro substituents at different positions. 3′-Hydroxythioflavanone with a hydroxy group at the 3′-position of thioflavanone had a 15–43× higher antioxidant activity than unmodified thioflavanone. Among thioflavanones, 3′-nitrothioflavanone and 3′-hydroxythioflavanone showed increased inhibitory activities against nitric oxide (NO) production, compared to unmodified thioflavanone in a lipopolysaccharide stimulated culture of macrophages cells. 3′-Hydroxy-thioflavanone with a functional group at the 3′-position is a potent antioxidant with an increased inhibitory activity against NO production, compared to unmodified thioflavanone compounds.

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Refrerences

  1. Kanaze FI, Bounartzi MI, Georgarakis M, Niopas I. Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects. Eur. J. Clin. Nutr. 61: 472–477 (2007)

    CAS  Google Scholar 

  2. Crespo ME, Galvez J, Cruz T, Ocete MA, Zarzuelo A. Antiinflammatory activity of diosmin and hesperidin in rat colitis induced by TNBS. Planta Med. 65: 651–653 (1999)

    Article  CAS  Google Scholar 

  3. Miyake Y, Yamamoto K, Tsujihara N, Osawa T. Protective effects of lemon flavonoids on oxidative stress in diabetic rats. Lipids 33: 689–695 (1998)

    Article  CAS  Google Scholar 

  4. Montforte MT, Trovato A, Kirjavainen S, Forestieri AM, Galati EM, Lo Cutro RB. Biological effects of hesperidin a citrus flavonoid hypolipidemic activity on experimental hypercholesterolemia in rat. Farmaco 50: 595–599 (1995)

    Google Scholar 

  5. Tanaka T, Makita H, Kawabata K, Mori H, Kakumoto M, Satoh K, Hara A, Sumida T, Tanaka T, Ogawa H. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin. Carcinogenesis 18: 957–965 (1997)

    Article  CAS  Google Scholar 

  6. Lin HY, Shen SC, Chen YC. Anti-inflammatory effect of heme oxygenase 1: Glycosylation and nitric oxide inhibition in macrophages. J. Cell. Physiol. 202: 579–590 (2005)

    Article  CAS  Google Scholar 

  7. Lee JI. A new synthesis of thioflavanones from thiosalicylic acid. Bull. Korean Chem. Soc. 29: 1263–1265 (2008)

    Article  CAS  Google Scholar 

  8. Nathan C. Nitric oxide as a secretory product of mammalian cells. FASEB J. 6: 3051–3064 (1992)

    CAS  Google Scholar 

  9. Marletta MA. Nitric oxide synthase structure and mechanism. J. Biol. Chem. 268: 12231–12234 (1993)

    CAS  Google Scholar 

  10. Lala PK, Chakraborty C. Role of nitric oxide in carcinogenesis and tumor progression. Lancet Oncol. 2: 149–156 (2001)

    Article  CAS  Google Scholar 

  11. Thaipong K, Boonprako U, Crosby K, Cisneros-Zevallos L, Byrne DH. Comparison of ABTS, DPPH, FRAP, and ORAC assays for estimating antioxidant activity from guava fruit extracts. J. Food Compos. Anal. 19: 669–675 (2006)

    Article  CAS  Google Scholar 

  12. Číž M, Čížová H, Denev P, Kratchanova M, Slavov A, Lojek A. Different methods for control and comparison of the antioxidant properties of vegetables. Food Control 21: 518–523 (2010)

    Article  Google Scholar 

  13. Gomes A, Fernandes E, Lima JLFC. Fluorescence probes used for detection of reactive oxygen species. J. Biochem. Bioph. Meth. 65: 45–80 (2005)

    Article  CAS  Google Scholar 

  14. Ou BX, Huang DJ, Hampsch-Woodill M, Flanagan JA, Deemer EK. Analysis of antioxidant activities of common vegetables employing oxygen radical absorbance capacity (ORAC) and ferric reducing antioxidant power (FRAP) assays: A comparative study. J. Agr. Food Chem. 50: 3122–3128 (2002)

    Article  CAS  Google Scholar 

  15. Lee JH, Jeong CS, Kim GH. Antioxidant and suppressive effects of ethanolic extract fractions from safflower (Carthamus tinctorius L.) flower on the biosynthesis of inflammatory mediators from LPSstimulated RAW 264.7 cells. Food Sci. Biotechnol. 18: 143–149 (2009)

    Google Scholar 

  16. Sutherland H, Khundkar R, Zolle O, McArdle A, Simpson AWM, Jarvis JC, Salmons S. A fluorescence-based method for measuring nitric oxide in extracts of skeletal muscle. Nitric Oxide 5: 475–481 (2001)

    Article  CAS  Google Scholar 

  17. Rice-Evans C, Miller N, Paganga G. Antioxidant properties of phenolic compounds. Trends Plant Sci. 2: 152–159 (1997)

    Article  Google Scholar 

  18. Lopaczynski W, Zeisel SH. Antioxidant, programmed cell death, and cancer. Nutr. Res. 21: 295–307 (2001)

    Article  CAS  Google Scholar 

  19. Carlo GD, Mascolo N, Izzo AA, Capasso F. Minireview-flavonoids: Old and new aspects of a class of natural therapeutic drugs. Life Sci. 65: 337–353 (1999)

    Article  Google Scholar 

  20. Halliwell B, Hoult JR, Blake DR. Oxidants, inflammation, and antiinflammatory drugs. FASEB J. 2: 2867–2873 (1988)

    CAS  Google Scholar 

  21. Kaplan HB, Edelson HS, Korchak HM, Given WP, Abramson S, Weissmann G. Effects of non-steroidal anti-inflammatory agents on human neutrophil functions in vitro and in vivo. Biochem. Pharmacol. 33: 371–378 (1984)

    Article  CAS  Google Scholar 

  22. Hurst NP, French JK, Gorjatschko L, Betts WH. Chloroquine and hydroxychloroquine inhibit multiple sites in metabolic pathways leading to neutrophil superoxide release. J. Rheumatol. 15: 23–27 (1988)

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Duksung Women’s University, Seoul, 132-714, Korea

    Jae In Lee

  2. Department of Food and Nutrition, Kongju National University, Chungnam, 340-702, Korea

    Je-Hyuk Lee

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  1. Jae In Lee
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  2. Je-Hyuk Lee
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Correspondence to Je-Hyuk Lee.

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Lee, J.I., Lee, JH. Antioxidant and inhibitory activities of thioflavanones against nitric oxide production. Food Sci Biotechnol 23, 957–963 (2014). https://doi.org/10.1007/s10068-014-0129-x

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  • DOI: https://doi.org/10.1007/s10068-014-0129-x

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