Skip to main content

Advertisement

Log in

Tricin 4′-O-(erythro-β-guaiacylglyceryl) ether and tricin 4′-O-(threo-β-guaiacylglyceryl) ether isolated from Njavara (Oryza sativa L. var. Njavara), induce apoptosis in multiple tumor cells by mitochondrial pathway

  • Original Paper
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

Njavara is an important medicinal rice variety of Kerala, India widely used in Ayurveda for the treatment of rheumatoid arthritis, paralysis, neurodegenerative diseases and in rejuvenation therapy. The study evaluated, for the first time, antitumor effects of the two rare flavonolignans, tricin 4′-O-(erythro-β-guaiacylglyceryl) ether (compound 1) and tricin 4′-O-(threo-β-guaiacylglyceryl) ether (compound 2), isolated from ‘Njavara’ black. Both the compounds induced apoptosis in three cancer cell lines colon adenocarcinoma cell line HCT 116, ovarian cancer cell line SKOV3 and breast cancer cell line MCF-7. Chromatin condensation in the three cancer cell lines by Hoechst staining showed >50 % of apoptosis by compounds 1 and 2 at concentration 40 and 30 μg/ml, respectively after 48 h. Further studies substantiated that both the compounds targeted cancer cells through mitochondrial membrane potential loss and subsequent chromatin condensation. Both compounds significantly increased the Annexin V binding thus confirming compounds 1 and 2 to be potential apoptotic agents.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Kerr JFR, Winterford CM, Harmon BV (1994) Apoptosis: its significance in cancer and cancer therapy. Cancer 73:2013–2026

    Article  PubMed  CAS  Google Scholar 

  2. Hengartner MO (2000) The biochemistry of apoptosis. Nature 407:770–776

    Article  PubMed  CAS  Google Scholar 

  3. Harada H, Grant S (2003) Apoptosis regulators. Rev Clin Exp Hematol 7:117–138

    PubMed  CAS  Google Scholar 

  4. Ghobrial IM, Witzig TE, Adjei AA (2005) Targeting apoptosis pathways in cancer therapy. CA Cancer J Clin 55:178–194

    Article  PubMed  Google Scholar 

  5. Pan MH, Ho CT (2008) Chemopreventive effects of dietary compounds on cancer development. Chem Soc Rev 37:2558–2574

    Article  PubMed  CAS  Google Scholar 

  6. Cragg GM, Newman DJ (2009) Nature: a vital source of leads for anticancer drug development. Phytochem Rev 8:313–331

    Article  CAS  Google Scholar 

  7. Tansuwanwong S, yamamoto H, Imai K, Viniketkumnuen U (2009) Antiproliferation and apoptosis on RKO colon cancer by Millintonia hortensis. Plant Foods Hum Nutr 64:11–17

    Article  PubMed  Google Scholar 

  8. Mohanlal S, Parvathy R, Shalini V, Helen A, Jayalekshmy A (2011) Isolation, characterisation and quantification of tricin and flavonolignans in the medicinal rice Njavara (Oryza sativa L.) as compared to staple varieties. Plant Foods Hum Nutr 66:91–96

    Article  PubMed  CAS  Google Scholar 

  9. Rao AS, Reddy SG, Babu PP, Reddy AR (2010) The antioxidant and antiproliferative activities of methanolic extracts from Njavara rice bran. BMC Complement Altern Med 10:4

    Article  PubMed  Google Scholar 

  10. 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 Prev 9:1163–1170

    PubMed  CAS  Google Scholar 

  11. Karunagaran D, Rashmi R, SanthoshKumar TR (2005) Induction of apoptosis by curcumin and its implications for cancer therapy. Curr Cancer Drug Targ 5:117–129

    Article  CAS  Google Scholar 

  12. Sahai M, Harle J, Begum SA, Ray AB (2010) Nonconventional lignans: coumarinolignans, flavonolignans and stilbenolignans. Fortschritte der Chemie organischer Naturstoffe. Prog Chem Org Nat Prod (Progrès dans la chimie des substances organiques naturelles) 93:1–70

    Google Scholar 

  13. Dixit N, Baboota S, Kohli K, Ahmed S, Ali J (2007) Silymarin: a review of pharmacological aspects and bioavailability enhancement approaches. Indian J Pharmacol 39:172–179

    Article  CAS  Google Scholar 

  14. Duan W, Jin X, Li Q, Tashiro SI, Onodera S, Ikejima T (2010) Silibinin induced autophagic and apoptotic cell death in HT1080 cells through a reactive oxygen species pathway. J Pharmacol Sci 113:48–56

    Article  PubMed  CAS  Google Scholar 

  15. 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: 155–158)

    Google Scholar 

  16. Bouaziz M, Veitch NC, Grayer RJ, Simmonds MSJ, Damak M (2002) Flavonolignans from Hyparrhenia hirta. Phytochemistry 60:515–520

    Article  PubMed  CAS  Google Scholar 

  17. Wenzig E, Kunert O, Ferreira D, Schimid M, Schuhly W, Bauer R, Hiermann A (2005) Flavonolignans from Avena sativa. J Nat Prod 68:289–292

    Article  PubMed  CAS  Google Scholar 

  18. 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 73:1482–1488

    Article  PubMed  CAS  Google Scholar 

  19. Chang C, Wang G, Zhang L, Tsai W, Chen R, Wu Y, Kuo Y (2010) Cardiovascular protective flavonolignans and flavonoids from Calamus quiquesetinervius. Phytochemistry 71:271–279

    Article  PubMed  CAS  Google Scholar 

  20. Crompton M (1999) The mitochondrial permeability transition pore and its role in cell death. Biochem J 341:233–249

    Article  PubMed  CAS  Google Scholar 

  21. Elmore S (2007) Apoptosis: a review of programmed cell death. Toxicol Pathol 35:495–516

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

The authors (SM and AJ) are grateful for the funding assistance provided by Kerala State Council for Science, Technology and Environment (KSCSTE), Government of Kerala. The author (SM) 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, CSIR-NIIST and Director, Rajiv Gandhi Centre for Biotechnology (RGCB) for constant encouragement and support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ananthasankaran Jayalekshmy.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 15374 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mohanlal, S., Maney, S.K., Santhoshkumar, T.R. et al. Tricin 4′-O-(erythro-β-guaiacylglyceryl) ether and tricin 4′-O-(threo-β-guaiacylglyceryl) ether isolated from Njavara (Oryza sativa L. var. Njavara), induce apoptosis in multiple tumor cells by mitochondrial pathway. J Nat Med 67, 528–533 (2013). https://doi.org/10.1007/s11418-012-0710-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-012-0710-7

Keywords

Navigation