Analysis of flavonoids and characterization of theOsFNS gene involved in flavone biosynthesis in Rice

  • Jeong Ho Kim
  • Young Min Cheon
  • Bong -Gyu Kim
  • Joong -Hoon Ahn
Article

Abstract

The major flavonoids in rice leaves were analyzed via LC-MS/MS after their total flavonoid extracts were hydrolyzed. The most abundant flavones were apigenin, luteolin, and tricetin. Of these, tricetin was methylated at its 3′ and 5′-hydroxyl group to form tricin, which was probablyO-glycosylated. Both 3′-O-methylated luteolin and luteolin were found in theC-glycosylated form while apigenin wasC-glycosylated. We also cloned and characterizedOsFNS, which catalyzes the reaction from flavanone (naringenin) to flavone (apigenin). Analysis of the reaction product with recombinant OsFNS showed that it indeed converts naringenin to apigenin.

Key words

flavones flavone synthase flavonoid analysis Oryza sativa 

Literature Cited

  1. Cai H, Hudson EA, Mann P, Verschoyle RD, Greaves P, Manson MM, Stepward WP, Gescher AJ (2004) Growth-inhibitory and cell cycle-arresting properties of the rice bran constituent in human-derived breast cancer cellsin vitro and in nude micein vivo. Brit J Cancer91: 1364–1371PubMedCrossRefGoogle Scholar
  2. Croteau R, Kutchan TM, Lewis NG (2000) Natural products (secondary metabolites).InBB Buchanan, G Gruissem, RL Jones, eds, Biochemistry and Molecular Biology of Plants. American Society of Plant Physiologists, Rockville, MD, USA, pp1250–1318Google Scholar
  3. Feldmann KA (2001) Cytochrome P450s as genes for crop improvement. Curr OpinPlant Biol4: 162–167CrossRefGoogle Scholar
  4. Ferreres F, Silva BM, Andrade PN, Seabra RM, Derreira MA (2003) Approach to the study of C-glycosyl flavones by ion trap HPLC-PAD-ESI/MS/MS: Application to seed of quince(Cydonia oblonga). Phytochem Anal14: 352–359PubMedCrossRefGoogle Scholar
  5. Hausinger RP (2004) Fe(II)/α-ketoglutarate-dependent hydroxylase and related enzymes. Crit Rev Biochem Mol Biol39: 21–68PubMedCrossRefGoogle Scholar
  6. Hudson EA, Dinh PA, Kokubun T, Simmonds MSJ, Gescher A (2000) Characterization of potentially chemopreventive phenols in extracts of brown rice that inhibit the growth of human breast and colon cancer cells. Cancer Epidemiol Biomarkers Prev9: 1163–1170PubMedGoogle Scholar
  7. Kim BG, Lee YJ, Park Y, Lim Y, Ahn J-H (2006a) Caffeic acid O-methyltransferase fromPopulus deltoides: Functional expression and characterization. J Plant Biol49: 55–60Google Scholar
  8. Kim BG, Lee Y, Hur H-G, Lim Y, Ahn J-H (2006b) Flavonoid 3′-O- methyltransferase from rice: cDNA cloning, characterization and functional expression. Phytochemistry67: 387–394PubMedCrossRefGoogle Scholar
  9. Kim BG, Kim JH, Min SY, Shin KH, Kim JH, Kim HI, Ryu SN, Ahn J-H (2007) Anthocyanin content in rice is related to expression level of anthocyanin biosynthetic genes. J Plant Biol50: 156–160CrossRefGoogle Scholar
  10. Ko JH, Kim BG, Hur H-G, Lim Y, Ahn J-H (2006) Molecular cloning, expression and characterization of a glycosyltransferase from rice. Plant Cell Rep25: 141–146CrossRefGoogle Scholar
  11. Markham KR (1982a) Ultraviolet-visible absorption spectroscopyIn Techniques of Flavonoid Identification. Academic Press, London, pp 36–51Google Scholar
  12. Markham KR (1982b) Hydrolysis and the analysis of glycosides,In Techniques of Flavonoid Identification. Academic Press, London, pp 52–57Google Scholar
  13. Martens S, Mithõfer A (2005) Flavones and flavones synthases. Phytochemistry66: 2399–2407PubMedCrossRefGoogle Scholar
  14. Miyahisa I, Kaneko M, Funa N, Kawasaki H, Kojirma H, Ohnishi Y, Horinouchi S (2006) Efficient production of (2S)-flavones byEscherichia coli containing an artificial biosynthetic gene cluster. Appl Microbiol Biotechnol68: 498–504CrossRefGoogle Scholar
  15. Stevenson PC, Kimmins FM, Grayer RJ, Raveendranath S (1996) Schaftosides from rice phloem as feeding inhibitors and resistance factors to brown planthoppers,Niaparvata lugens. Entomol Exp Appl80: 246–249CrossRefGoogle Scholar
  16. Tahara S (2007) A journey of twenty-five years through the ecological biochemistry of flavonoids. Biosci Biotechnol Biochem71: 1387–1404PubMedCrossRefGoogle Scholar
  17. Turnbull J, Nakajima J, Welford RWD, Yamazaki M, Saito K, Schofield, CJ (2004) Mechanistic studies on three 2-oxoglut-arate-dependent oxygenases of flavonoid biosynthesis: Anthocyanidin synthase, flavonol synthase and flavanone 3â-hydroxylase. J Biol Chem279: 1206–1216PubMedCrossRefGoogle Scholar

Copyright information

© The Botanical Society of Korea 2008

Authors and Affiliations

  • Jeong Ho Kim
    • 1
  • Young Min Cheon
    • 1
  • Bong -Gyu Kim
    • 1
  • Joong -Hoon Ahn
    • 1
  1. 1.Department of Bioscience and BiotechnologyBio/Molecular Informatics Center, Konkuk UniversitySeoulKorea

Personalised recommendations