Skip to main content
SpringerLink
Log in

Potential antimalarial derivatives from astraodorol

  • Research Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Astraodorol, a major lanostane-type triterpene isolated from the edible mushroom Astraeus odoratus, was subjected to chemical modifications. Ten derivatives have been synthesized and their biological activities were evaluated. Compounds 5, 6, 7a, 7c, 7e, 7f, and 7 g exhibited strong antimalarial activity with IC50 values of 4.85, 4.48, 4.16, 4.46, 3.45, 3.23, and 3.41 µg/mL, respectively. Compounds 7a, 7c, and 7e showed moderate cytotoxicity against NCI-H187 with IC50 values of 23.36, 34.28, and 9.84 µg/mL. Compound 7e demonstrated moderate cytotoxicity against KB, MCF-7, and Vero cell lines with IC50 values of 16.94, 49.60, and 26.48 µg/mL, respectively.

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

Scheme 1
Scheme 2

Similar content being viewed by others

References

  • Arpha, K., C. Phosri, N. Suwannasai, W. Mongkolthananruk, and S. Sodngam. 2013. Astraodoric acids A–D: new lanostane triterpenes from edible mushroom Astraeus odoratus and their anti-Mycobacterium tuberculosis H37Ra and cytotoxicity. Journal of Agricultural and Food Chemistry 60: 9834–9841.

    Article  Google Scholar 

  • Babar, Z.U., A. Ata, and M.H. Meshkatalsadat. 2006. New bioactive steroidal alkaloids from Buxus hyrcana. Steroids 71: 1045–1051.

    Article  Google Scholar 

  • Batista, R., A. De Jesus Silva Junior, and B. De Oliveira. 2009. Plant-derived antimalarial agents: new leads and efficient phytomedicines. Part II. Non-alkaloidal natural products. Molecules 14: 3037–3072.

    Article  CAS  PubMed  Google Scholar 

  • Brien, J.O., I. Wilson, T. Orton, and F. Opognan. 2000. Investigation of the alamar blue (resazurin) fluorescent for the assessment of mammalian cell cytotoxicity. European Journal of Biochemistry 267: 5421–5426.

    Article  Google Scholar 

  • Desjardins, R.E., C.J. Canfield, J.D. Haynes, and J.D. Chulay. 1979. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrobial Agents and Chemotherapy 16: 710–718.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Devkova, K.P., B.N. Lenta, J.D. Wansi, M.I. Choudhary, D.P. Kisangau, N.Q. Samreen, and N. Sewald. 2008. Bioactive 5α-Pregnane-type steroidal alkaloids from Sarcococca hookeriana. Journal of Natural Products 71: 1481–1484.

    Article  Google Scholar 

  • Dondorp, A.M., F. Nosten, P. Yi, et al. 2009. Artemisinin resistance in Plasmodium falciparum malaria. New England Journal of Medicine 361: 455–467.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Enserink, M. 2008. Lower malaria numbers reflect better estimates and a glimmer of hope. Science 321: 1620.

    Article  CAS  PubMed  Google Scholar 

  • Foley, M., and L. Tilley. 1997. Quinoline antimalarials: mechanisms of action and resistance. International Journal for Parasitology 27: 231–240.

    Article  CAS  PubMed  Google Scholar 

  • Glaziou, P., K. Floyd, and M. Raviglione. 2009. Global burden and epidemiology of tuberculosis. Clinics in Chest Medicine 30: 621–636.

    Article  PubMed  Google Scholar 

  • Gupta, C., S. Prasad, M. Sahai, T. Asai, N. Hara, Y. Fujimoto, and A.-E. Artabotryols. 2010. New lanostane triterpenes from the seeds of Artabotrys odoratissimus. Helvetica Chimica Acta 93: 1925–1932.

    Article  CAS  Google Scholar 

  • Hunt, L., M. Jordan, M. De Jesus, and F.M. Wurm. 1999. GFP-expressing mammalian cells for fast, sensitive, noninvasive cell growth assessment in a kinetic mode. Biotechnology and Bioengineering 65: 201–205.

    Article  CAS  PubMed  Google Scholar 

  • Kaur, K., M. Jain, T. Kuar, and R. Jain. 2009. Antimalarials from nature. Bioorganic Medicinal Chemistry 17: 3229–3256.

    Article  CAS  PubMed  Google Scholar 

  • Noedl, H., Y. Se, K. Schaecher, B.L. Smith, D. Socheat, and M.M. Fukuda. 2008. Evidence of Artemisinin-resistant malaria in western Cambodia. New England Journal of Medicine 359: 2619–2620.

    Article  CAS  PubMed  Google Scholar 

  • Rathore, D., D. Jani, R. Nagarkatti, and S. Kumar. 2006. Heme detoxification and antimalarial drugs-known mechanisms and future prospects. Drug Discovery Today 3: 153–158.

    Article  Google Scholar 

  • Seo, H.W., T.M. Hung, M. Na, et al. 2009. Steroids and triterpenes from the fruiting bodies of Ganoderma lucidum and their anti-complement activity. Archives of Pharmacal Research 32: 1573–1579.

    Article  CAS  PubMed  Google Scholar 

  • Skinner-Adams, T.S., C.M. Stack, K.R. Trenholme, C.L. Brown, J. Grembecka, J. Lowther, A. Mucha, M. Drag, P. Kafarski, S. Mcgowan, J.C. Whisstock, D.L. Gardiner, and J.P. Dalton. 2009. Plasmodium falciparum neutral aminopeptidases: new targets for anti-malarials. Trends in Biochemical Sciences 35: 53–61.

    Article  PubMed  Google Scholar 

  • Stanikunaite, R., M.M. Rawan, J.M. Trappe, F. Fronzeck, and S.A. Ross. 2008. Lanostane-type triterpenes from the mushroom Astraeus pteridis with antituberculosis activity. Journal of Natural Products 71: 2077–2079.

    Article  CAS  PubMed  Google Scholar 

  • Trager, W., and J.B. Jensen. 1976. Human malaria parasites in continuous culture. Science 193: 673–675.

    Article  CAS  PubMed  Google Scholar 

  • WHO. 2013. World malaria report. Geneva: World Health Organization. 2013.

    Google Scholar 

  • WHO. 2010. Guidelines for the treatment of malaria, 2nd ed. Geneva: World Health Organization.

    Google Scholar 

Download references

Acknowledgments

This work was supported by the office of the National Research Council of Thailand (NRCT), the Centre of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education and Graduate School of Khon Kaen University.

Author information

Authors and Affiliations

  1. Natural Products Research Unit, Centre of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, 40002, Thailand

    Pitak Nasomjai, Kittibhorn Arpha & Sirirath Sodngam

  2. School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Liverpool, L3 3AF, UK

    Simon D. Brandt

Authors
  1. Pitak Nasomjai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kittibhorn Arpha
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sirirath Sodngam
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Simon D. Brandt
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Pitak Nasomjai.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2097 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nasomjai, P., Arpha, K., Sodngam, S. et al. Potential antimalarial derivatives from astraodorol. Arch. Pharm. Res. 37, 1538–1545 (2014). https://doi.org/10.1007/s12272-014-0393-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-014-0393-6

Keywords

Search

Navigation