Download PDF
Planta Med 2004; 70(6): 496-501
DOI: 10.1055/s-2004-827147
Original Paper
Pharmacology
© Georg Thieme Verlag KG Stuttgart · New York

Anti-Inflammatory Isoflavonoids from the Stems of Derris scandens

Pisamai Laupattarakasem1 , 2 , Peter J. Houghton1 , J. Robin S. Hoult3 , 4
  • 1Department of Pharmacy, King’s College London, London, U.K.
  • 2Current address: Pharmacology Department, Faculty of Medicine, Khon Kaen University, Khon Kaen, Thailand
  • 3Messengers and Signalling Research Group, GKT School of Biomedical Sciences, King’s College London, London, U.K.
  • 4Deceased 24th April 2001
Our grateful thanks to Faculty of Medicine, Khon Khaen University, Thailand for a PhD scholarship for Dr Laupattarakasem.
Further Information

Publication History

Received: November 11, 2003

Accepted: February 15, 2004

Publication Date:
01 July 2004 (online)

Also available at
    Permissions and Reprints

Abstract

Fractionation of the aqueous extract of Derris scandens stems extract using tests for eicosanoid inhibition resulted in the isolation of three isoflavonoids, genistein, its 7-O-α-rhamno(1→6)-β-glucosyl glycoside, a new compound, and two known isoprenyl derivatives 3′-γ,γ-dimethylallylweighteone and scandenin. The isoprenylated compounds showed a high inhibitory effect on eicosanoid production in vitro but HPLC analysis showed that the genistein accounted for most of the activity of the total extract. Antioxidant studies showed that genistein and the isoprenylated compounds showed activity comparable to standard antioxidants. Genistein and its glycoside demonstrated no cytotoxicity in the MTT test but the prenylated compounds showed some toxicity and also increased LDH release from polymorphonucleocytes, at concentrations much greater than would be encountered in an aqueous extract of D. scandens.

Key words

Derris scandens - Leguminosae - isoflavonoids - eicosanoid inhibition - antioxidant - anti-inflammatory

References

  • 1 Laupattarakasem P, Houghton P J, Hoult J RS, Itharat A. An evaluation of the activity related to inflammation of four plants used in Thailand to treat arthritis.  Journal of Ethnopharmacology. 2003;  85 207-15
    CrossrefPubMedSearch in Google Scholar
  • 2 De las Heras B, Hoult J RS. Non-cytotoxic inhibition of macrophage eicosanoid biosynthesis and effects on leukocyte functions and reactive oxygen species of two novel anti-inflammatory plant diterpenoids.  Planta Medica. 1994;  60 501-6
    PubMedSearch in Google Scholar
  • 3 Scott K F, Bryant K J, Bidgood M J. Functional coupling and differential regulation of the phospholipase A2-cycloxygenase pathways in inflammation.  Journal of Leukocyte Biology. 1999;  66 535-41
    PubMedSearch in Google Scholar
  • 4 Bauer R. Cycloxygenase and 5-lipoxygenase as targets for medicinal plant research. in: Bohlin L, Bruhn JG (Eds.) Bioassay Methods in Natural Products Research and Drug Development. Kluwer Academic Dordrecht, Netherlands; 1999: pp 119-42
    Search in Google Scholar
  • 5 Cuzzocrea S, Riley D P, Caputi A P, Salvemini D. Antioxidant therapy: A new pharmacological approach in shock, inflammation and ischemia/reperfusion injury.  Pharmacology Reviews. 2001;  53 135-9
    PubMedSearch in Google Scholar
  • 6 Hoult J RS, Pang L -H, Bland-Ward P, Forder R, Williams C, Harborne J B. Inhibition of leukocyte 5-lipoxygenase and cyclooxygenase but not constitutive nitric oxide synthase by tanetin, a novel flavonoid derived from feverfew, Tanacetum parthenium .  Pharmaceutical Sciences. 1995;  1 71-4
    PubMedSearch in Google Scholar
  • 7 Fridovitch I. Superoxide dismutase: an adaptation to a paramagnetic gas.  Journal of Biological Chemistry. 1989;  264 7761-4
    PubMedSearch in Google Scholar
  • 8 Aruoma O I. Assessment of potential prooxidant and antioxidant actions.  Journal of the American Oil Chemists Society. 1996;  73 1617-25
    PubMedSearch in Google Scholar
  • 9 Paya M, Halliwell B, Hoult J RS. Interaction of a series of coumarins with reactive oxygen species.  Biochemical Pharmacology. 1992;  44 205-14
    CrossrefPubMedSearch in Google Scholar
  • 10 Mosmann T. Rapid colourimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  Journal of Immunological Methods. 1983;  65 55-63
    CrossrefPubMedSearch in Google Scholar
  • 11 van de Casteele K, Geiger H, van Sumere C. Separation of flavonoids by high-performance liquid chromatography.  Journal of Chromatography. 1982;  240 81-94
    CrossrefPubMedSearch in Google Scholar
  • 12 Mabry T, Markham K, Thomas M. The systematic identification of flavonoids. New York; Springer 1970: p 55
    Search in Google Scholar
  • 13 Slimestad R, Andersen Ø M, Francis G W, Marston A, Hostettmann K. Syringetin 3-O-(6′′-acetyl)-β-glucopyranoside and other flavonols from needles of Norway spruce, Picea abies .  Phytochemistry. 1995;  40 1537-42
    CrossrefPubMedSearch in Google Scholar
  • 14 Singhal A, Sharma R, Thyagarajan G, Herz W, Govindan S. New prenylated isoflavones and a prenylated dihydroflavonol from Millettia pachycarpa .  Phytochemistry. 1980;  19 929-34
    CrossrefPubMedSearch in Google Scholar
  • 15 Rao M, Krupadanam G, Srimannarayana G. Four isoflavones and two 3-arylcoumarins from stems of Derris scandens .  Phytochemistry. 1994;  37 267-9
    CrossrefPubMedSearch in Google Scholar
  • 16 Johnson A, Pelter A, Stainton P. The extractives from Derris scandens. Part I. The structures of scandenin and lonchocarpic acid. Journal of the Chemical Society C 1969: 192-202
    Search in Google Scholar
  • 17 Kniss D, Zimmerman P, Su H, Fertal R. Genistein suppresses EGF-induced prostaglandin synthesis by a mechanism independent of EGF receptor tyrosine kinase inhibition.  Prostaglandins. 1996;  57 87-105
    PubMedSearch in Google Scholar
  • 18 Ozaki Y, Yatomi Y, Jinnai Y, Kume S. Effects of genistein, a tyrosine kinase inhibitor, on platelet functions.  Biochemical Pharmacology. 1993;  46 395-403
    CrossrefPubMedSearch in Google Scholar
  • 19 Kusunoki T, Higashi H, Hosoi S, Hata D, Sugie K, Mayumi M, Mikawa H. Tyrosine phosphorylation and its possible role in superoxide production by human neutrophils stimulated with fMLP and IgG.  Biochemical and Biophysics Research Communications. 1992;  183 789-96
    PubMedSearch in Google Scholar
  • 20 Bruggiser R, van Daeniken K, Jundt G, Schaffner W, Tullberg-Reinert H. Interference of plant extracts, phytoestrogens and antioxidants with the MTT tetrazolium assay.  Planta Medica. 2002;  68 445-8
    Thieme ConnectPubMedSearch in Google Scholar

Prof. Peter J. Houghton

Department of Pharmacy

King’s College London

Franklin-Wilkins Building

150 Stamford Street

London, SE1 9NN

U.K.

Fax: +44-20-7848-4800

Email: peter.houghton@kcl.ac.uk