Skip to main content
SpringerLink
Log in

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

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

Abstract

Two chalcone derivatives, 2′-hydroxychalcone (1) and desmethylinfectocaryone (2), together with five known phenolic compounds infectocaryone (3), cryptocaryone (4), kurzichalcolactone A (5), pinocembrin (6) and trans-N-feruloyltyramine (7), were isolated from the methanol extract of the wood of Cryptocarya konishii. The structures of the new compounds were determined based on the analysis of spectroscopic data, including UV, IR, 1D and 2D NMR, and mass spectra. Evaluation of the cytotoxic and tyrosine kinase inhibitory activities of compounds 1–7 showed that compounds 2–4 strongly inhibited the growth of murine leukemia P-388 cells, whereas compound 4 significantly inhibited the enzyme.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Cronquist A (1981) An integrated system of classification of flowering plants. Columbia University Press, New York, pp 74–78

    Google Scholar 

  2. Awang K, Hadi AHA, Saidi N, Mukhtar MR, Morita H, Litaudon M (2008) New phenantrene alkaloids from Cryptocarya crassinervia. Fitoterapia 79:308–310

    Google Scholar 

  3. Toribio A, Bonfils A, Delannay E, Prost E, Harakat D, Henon E, Richard B, Litaudon M, Nuzillard J-M, Renault J-H (2006) Novel seco-dibenzopyrrocoline alkaloid from Cryptocarya oubatchensis. Org Lett 8:3825–3828

    Article  CAS  PubMed  Google Scholar 

  4. Lin F-W, Wang J-J, Wu T-S (2002) New pavine N-oxide alkaloids from the stem bark of Cryptocarya chinensis Hemsl. Chem Pharm Bull 50:157–159

    Article  CAS  PubMed  Google Scholar 

  5. Dumontet V, Van Hung N, Adeline M-T, Riche C, Chiaroni A, Sevenet T, Gueritte F (2004) Cytotoxic flavonoids and α-pyrones from Cryptocarya obovata. J Nat Prod 67:858–862

    Article  CAS  PubMed  Google Scholar 

  6. Chan Y-Y, Wu C-H, Wu S-J, Wu T-S (2002) The constituents and synthesis of cryptamygin-A from the stem bark of Cryptocarya amygdalina. J Chin Chem Soc 49:263–268

    CAS  Google Scholar 

  7. Schmeda-Hirschmann G, Astudillo L, Bastida J, Codina C, De Arias AR, Ferreira ME, Inchaustti A, Yaluff G (2001) Cryptofolione derivatives from Cryptocarya alba fruits. J Pharm Pharmacol 53:563–567

    Article  CAS  PubMed  Google Scholar 

  8. Juliawaty LD, Kitajima M, Takayama H, Achmad SA, Aimi N (2000) A 6-substituted-5,6-dihydro-2-pyrone from Cryptocarya strictifolia. Phytochemistry 54:989–993

    Article  CAS  PubMed  Google Scholar 

  9. Usman H, Hakim EH, Harlim T, Jalaluddin MN, Syah YM, Achmad SA, Takayama H (2006) Cytotoxic chalcones and flavanones from the tree bark of Cryptocarya costata. Z Naturforsch 61c:184–188

    Google Scholar 

  10. Dumontet V, Gaspard C, Van Hung N, Fahy J, Tchertanov L, Sevenet T, Gueritte F (2001) New cytotoxic flavonoids from Cryptocarya infectoria. Tetrahedron 57:6189–6196

    Article  CAS  Google Scholar 

  11. Lu S-T (1966) Alkaloids of Formosan lauraceous plants. IX. Alkaloids of Cryptocarya chinensis and C. konishii. Yakugaku Zasshi 86:296–299

    CAS  PubMed  Google Scholar 

  12. Lu S-T (1967) Alkaloids of Formosan lauraceous plants. XII. Alkaloids of Cryptocarya konishii and Machilus acuminatissimus. Yakugaku Zasshi 87:1278–1281

    CAS  PubMed  Google Scholar 

  13. Lee SS, Lin YJ, Chen CK, Liu KCS, Chen CH (1993) Quaternary alkaloids from Litsea cubeba and Cryptocarya konishii. J Nat Prod 56:1971–1976

    Article  CAS  Google Scholar 

  14. Govindachari TR, Parthasarathy PC, Desai HK, Shanbhag MN (1973) Structure of cryptocaryone. Constituent of Cryptocarya bourdilloni. Tetrahedron 29:3091–3094

    Article  CAS  Google Scholar 

  15. Wagner H, Chari VM, Sonnenbichler J (1976) 13C-NMR-spektren naturlich vorkommender flavonoide. Tetrahedron Lett 17:1799–1802

    Article  Google Scholar 

  16. Fu X, Sevenet T, Hamid A, Hadi A, Remy F, Pais M (1993) Kurzilactone from Cryptocarya kurzii. Phytochemistry 33:1272–1274

    Article  CAS  Google Scholar 

  17. Yoshihara T, Yamaguchi K, Takamatsu S, Sakamura S (1981) A new lignan amide, grossamide, from bell pepper (Capsicum annuum var. grossum). Agric Biol Chem 45:2593–2598

    CAS  Google Scholar 

  18. Sahidin HEH, Juliawaty LD, Syah YM, Din LB, Ghisalberti EL, Latip J, Said IM, Achmad SA (2005) Cytotoxic properties of oligostilbenoids from the tree bark of Hopea dryobalanoides. Z Naturforsch 60c:723–727

    Google Scholar 

Download references

Acknowledgments

This study was supported by a JSPS (The Japan Society for the Promotion of Science) grant to one of us (FK) through Meiji Pharmaceutical University Asia/Africa Centre for Drug Discovery Program, Japan. Financial assistance from a Doctoral Research Grant, Higher Education Bureau, National Education Department of Republic Indonesia, is also gratefully acknowledged. We thank Cibodas Botanical Garden, West Java, Indonesia, for supplying and identifying the sample.

Author information

Authors and Affiliations

  1. Natural Products Research Group, Department of Chemistry, Bandung Institute of Technology, Jalan Ganeca 10, Bandung, 40132, Indonesia

    Fera Kurniadewi, Lia D. Juliawaty, Yana M. Syah, Sjamsul A. Achmad & Euis H. Hakim

  2. Department of Pharmacognosy and Phytochemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan

    Kiyotaka Koyama, Kaoru Kinoshita & Kunio Takahashi

Authors
  1. Fera Kurniadewi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lia D. Juliawaty
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yana M. Syah
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sjamsul A. Achmad
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Euis H. Hakim
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Kiyotaka Koyama
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Kaoru Kinoshita
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Kunio Takahashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Euis H. Hakim.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kurniadewi, F., Juliawaty, L.D., Syah, Y.M. et al. Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties. J Nat Med 64, 121–125 (2010). https://doi.org/10.1007/s11418-009-0368-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-009-0368-y

Keywords

Search

Navigation