Advertisement

Plant Foods for Human Nutrition

, Volume 66, Issue 1, pp 91–96 | Cite as

Isolation, Characterization and Quantification of Tricin and Flavonolignans in the Medicinal Rice Njavara (Oryza sativa L.), as Compared to Staple Varieties

  • Smitha Mohanlal
  • Rathnam Parvathy
  • Vasantha Shalini
  • Antony Helen
  • Ananthasankaran Jayalekshmy
ORIGINAL PAPER

Abstract

Njavara is an important medicinal rice variety of Kerala, India, widely used in Ayurveda as a ‘health food’ and in the treatment of rheumatoid arthritis, paralysis, neurodegenerative diseases and in rejuvenation therapy. Phytochemical investigations and spectroscopic studies of the diethyl ether fraction of methanolic extract of Njavara Black (NB) rice bran gave three important compounds namely, tricin and two rare flavonolignans- tricin 4′-O-(erythro-β-guaiacylglyceryl) ether and tricin 4′-O-(threo-β-guaiacylglyceryl) ether. The EC50 values of these compounds in DPPH system were 90.39, 352.04 and 208.1 μg/ml, respectively. Quantification of the compounds by HPLC in NB and staple, non-medicinal rice varieties Sujatha (SJ) and Palakkadan Matta (PM) showed that tricin is present 39.64 and 16.12 fold higher in NB, compared to SJ and PM, respectively. This is the first report on the occurrence of tricin at significantly higher levels in Njavara and occurrence of the two flavonolignans in Oryza sativa species. Of the three compounds, tricin and the threo- form of flavonolignan showed anti-inflammatory effect of >65% after 5 h, at 2 mg/kg, in carrageenan-induced, paw edema experiments in rats. The results of the study corroborate with the preferential use of Njavara in indigenous medicine, over staple varieties.

Keywords

Flavonolignans Njavara Rice bran Tricin Tricin 4′-O-(erythro-β- guaiacylglyceryl) ether Tricin 4′-O-(threo-β-guaiacylglyceryl) ether 

Abbreviations

COX

cyclooxygenase

DPPH

2, 2- diphenyl-1-picrylhydrazyl

EC50

amount of extract or compound needed to decrease the initial DPPH concentration by 50%

HPLC-PDA

high performance liquid chromatograph-photodiode array

IR

infra red

MS

mass spectrometry

NB

Njavara Black

ND

not detected

NMR

nuclear magnetic resonance

NO

nitric oxide

NSAIDs

non-steroidal anti-inflammatory drugs

PM

Palakkadan Matta

RAW 264.7

cell line of mouse macrophages

ROS

reactive oxygen species

SD

standard deviation

SEM

standard error mean

SJ

Sujatha

SPSS/PC+

statistical programme software

UV–VIS

ultra violet-visible

Notes

Acknowledgements

The authors are grateful for the funding assistance provided by Kerala State Council for Science, Technology and Environment (KSCSTE), Government of Kerala. The author Smitha Mohanlal wishes to thank Council of Scientific and Industrial Research (CSIR), India for the financial support as Senior Research Fellowship (SRF). Thanks are also due to Director, NIIST, CSIR and Head, Department of Biochemistry for constant encouragement and support.

Supplementary material

11130_2011_217_MOESM1_ESM.doc (1 mb)
ESM 1 (DOC 1067 kb)

References

  1. 1.
    Finkel T, Holbrook NJ (2000) Oxidants, oxidative stress and biology of aging. Nature 408:239–247CrossRefGoogle Scholar
  2. 2.
    Caili F, Huan S, Quanhong L (2006) A review on pharmacological activities and utilization technologies of pumpkin. Plant Foods Hum Nutr 61:73–80CrossRefGoogle Scholar
  3. 3.
    Arora S, Kaur K, Kaur S (2003) Indian medicinal plants as a reservoir of protective phytochemicals. Teratog Carcinog Mutagen Suppl 1:295–300CrossRefGoogle Scholar
  4. 4.
    Lopez V, Akerreta S, Casanova E, Garcia-Mina JM, Cavero RY, Calvo MI (2007) In vitro antioxidant and antirhizopus activities of Lamiaceae herbal extracts. Plant Foods Hum Nutr 62:151–155CrossRefGoogle Scholar
  5. 5.
    Deepa G, Venkatachalam L, Bhagyalakshmi N, Shashidhar HE, Singh V, Naidu KA (2009) Physicochemical and genetic analysis of an endemic rice variety, Njavara (Oryza sativa L.), in comparison to two popular south Indian cultivars, Jyothi (PTB 39) and IR 64. J Agric Food Chem 57:11476–11483CrossRefGoogle Scholar
  6. 6.
    Deepa G, Singh V, Naidu KA (2008) Nutrient composition and physicochemical properties of Indian medicinal rice-Njavara. Food Chem 106:165–171CrossRefGoogle Scholar
  7. 7.
    Simi CK, Abraham TE (2008) Physicochemical rheological and thermal properties of Njavara rice (Oryza sativa) starch. J Agric Food Chem 56:12105–12113CrossRefGoogle Scholar
  8. 8.
    Sanchez-Moreno C, Larrauri JA, Sauro-Calixto F (1998) A procedure to measure antiradical efficiency of polyphenols. J Sci Food Agric 76:270–276CrossRefGoogle Scholar
  9. 9.
    Ghosh MN, Singh H (1974) Inhibitory effect of a pyralizidine alkaloid, crotalaburnine, on rat paw oedema and cotton pellet granuloma. Br J Pharmacol 51:503–508Google Scholar
  10. 10.
    Winter CA, Risley EA, Nuss GV (1962) Carrageenin-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs. Proc Soc Exp Biol Med 111:544–547Google Scholar
  11. 11.
    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 Biomark Prev 9:1163–1170Google Scholar
  12. 12.
    Bouaziz M, Veitch NC, Grayer RJ, Simmonds MSJ, Damak M (2002) Flavonolignans from Hyparrhenia hirta. Phytochemistry 60:515–520CrossRefGoogle Scholar
  13. 13.
    Wenzig E, Kunert O, Ferreira D, Schimid M, Schuhly W, Bauer R, Hiermann A (2005) Flavonolignans from Avena sativa. J Nat Prod 68:289–292CrossRefGoogle Scholar
  14. 14.
    Cuzzocrea S, Nocentini G, Di Paola R, Agostini M, Mazzon E, Ronchetti S, Crisafulli C, Esposito E, Caputi AP, Riccardi C (2006) Proinflammatory role of glucocorticoid-induced TNF receptor-related gene in acute lung inflammation. J Immunol 177:631–641Google Scholar
  15. 15.
    Mazzon E, Esposito E, Di Paola R, Muia C, Crisafulli C, Genovese T, Caminiti R, Meli R, Bramanti P, Cuzzocrea S (2008) Effect of tumour necrosis factor-alpha receptor 1 genetic deletion on carrageenan-induced acute inflammation: A comparison with etanercept. Clin Exp Immunol 153:136–149CrossRefGoogle Scholar
  16. 16.
    Moscatelli V, Hnatyszyn O, Acevedo C, Megias J, Alcaraz MJ, Ferraro G (2006) Flavanoids from Artemisia copa with anti-inflamatory activity. Planta Med 72:72–74CrossRefGoogle Scholar
  17. 17.
    Chang C, Zhang L, Chen RY, Kuo LY, Huang J, Huang H, Lee K, Wu Y, Kuo Y (2010) Antioxidant and anti-inflammatory phenylpropanoid derivatives from Calamus quiquesetinervius. J Nat Prod 73:1482–1488CrossRefGoogle Scholar
  18. 18.
    Syrchina AI, Gorshkov AG, Shcherbakov VV, Zinchenko SV, Vereshchagin AL, Zaikov KL, Semenov AA (1992) Flavonolignans of Salsola collina. Khim Prir Soed 2:182–186, Engl. Trans., Chem Nat Compd 28:155–158Google Scholar
  19. 19.
    Zhou J, Ibrahim RK (2010) Tricin-a potential multifunctional nutraceutical. Phytochem Rev 9:413–424CrossRefGoogle Scholar
  20. 20.
    Verschoyle RD, Greaves P, Cai H, Borkhardt BM, D’Incalci M, Riccio E, Doppalapudi R, Kapetanovic IM, Steward WP, Gescher AJ (2006) Preliminary safety evaluation of the putative cancer chemopreventive agent tricin, a naturally occurring flavone. Cancer Chemother Pharmacol 57:1–6CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Smitha Mohanlal
    • 1
  • Rathnam Parvathy
    • 1
  • Vasantha Shalini
    • 2
  • Antony Helen
    • 2
  • Ananthasankaran Jayalekshmy
    • 1
  1. 1.Chemical Sciences & Technology DivisionNational Institute for Interdisciplinary Science and Technology (NIIST), CSIRThiruvananthapuramIndia
  2. 2.Department of BiochemistryUniversity of KeralaThiruvananthapuramIndia

Personalised recommendations