Planta Med 2012; 78(7): 730-736
DOI: 10.1055/s-0031-1298310
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Evaluation of Alkaloids and Isoflavonoids from the Australian Tree Erythrina vespertilio

Mehrdad Iranshahi1 , 2 , Hoan Vu2 , Ngoc Pham2 , Dusan Zencak2 , Paul Forster3 , Ronald J. Quinn2
  • 1Biotechnology Research Center and School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran
  • 2Eskitis Institute, Griffith University, Brisbane, Australia
  • 3Queensland Herbarium, Department of Environment & Resource Management, Brisbane Botanic Gardens, Brisbane, Australia
Weitere Informationen

Publikationsverlauf

received Nov. 26, 2011 revised February 1, 2012

accepted February 2, 2012

Publikationsdatum:
21. Februar 2012 (online)

Abstract

A new glucoalkaloid, vespertilioside, together with three known alkaloids, including 11-β-methoxyglucoerysovine, erysotrine, and hypaphorine, were isolated from the fruits of E. vespertilio Benth. In addition, three known isoflavonoids, including phaseollin, alpiniumisoflavone, and phaseollidin, were identified from the plant stems. The structures of compounds were determined by 1D/2D NMR and mass experiments. The cytotoxic activity of all compounds was evaluated against a metastatic prostate cancer cell line (PC3) and neonatal foreskin fibroblast (NFF) using a real-time label-free cell analyser. Among the tested compounds, phaseollidin showed cytotoxic activities against PC3 (IC50 = 8.83 ± 1.87 µM) and NFF (0.64 ± 0.37 µM) cell lines.

Supporting Information

References

  • 1 Mbafor J T, Ndom J C, Fomum Z T. Erythrina studies 33. Triterpenoid saponins from Erythrina sigmoidea.  Phytochemistry. 1997;  44 1151-1155
  • 2 Tanaka H, Tanaka T, Etoh H. Three pterocarpans from Erythrina crista-galli.  Phytochemistry. 1997;  45 835-838
  • 3 Chawla A S, Jackson A H. Erythrina and related alkaloids.  Nat Prod Rep. 1984;  1 371-373
  • 4 Ozawa M, Kishida A, Ohsaki A. Erythrinan alkaloids from seeds of Erythrina velutina.  Chem Pharm Bull. 2011;  59 564-567
  • 5 Cui L, Ndinteh D T, Na M, Thuong P T, Silike-Muruumu J, Njamen D, Mbafor J T, Fomurn Z T, Ahn J S, Oh W K. Erythrina studies, part 51. Isoprenylated flavonoids from the stem bark of Erythrina abyssinica.  J Nat Prod. 2007;  70 1039-1042
  • 6 Innok P, Rukachaisirikul T, Suksamrarn A. Flavanoids and pterocarpans from the bark of Erythrina fusca.  Chem Pharm Bull. 2009;  57 993-996
  • 7 Chong P, Rashid P. Can we prevent prostate cancer?.  Aust Fam Physician. 2005;  34 265-267
  • 8 Grothaus P G, Cragg G M, Newman D J. Plant natural products in anticancer drug discovery.  Curr Org Chem. 2010;  14 1781-1791
  • 9 Jiang A H, Gao H, Kelley M R, Qiao X X. Inhibition of APE1/Ref-1 redox activity with APX3330 blocks retinal angiogenesis in vitro and in vivo.  Vision Res. 2011;  51 93-100
  • 10 Sianina H, Konig A, Claus H, Frosch M, Schubert-Unkmeir A. Real-time impedance analysis of host cell response to meningococcal infection.  J Microb Methods. 2011;  84 101-108
  • 11 Smout M J, Kotze A C, McCarthy J S, Loukas A. A novel high throughput assay for anthelmintic drug screening and resistance diagnosis by real-time monitoring of parasite motility.  PloS Negl Trop Dis. 2010;  4 e885
  • 12 Ungefroren H, Sebens S, Groth S, Gieseler F, Fandrich F. Differential roles of Src in transforming growth factor-beta regulation of growth arrest, epithelial-to-mesenchymal transition and cell migration in pancreatic ductal adenocarcinoma cells.  Int J Oncol. 2011;  38 797-805
  • 13 Urcan E, Haertel U, Styllou M, Hickel R, Scherthan H, Reichl F X. Real-time xCELLigence impedance analysis of the cytotoxicity of dental composite components on human gingival fibroblasts.  Dent Mater. 2010;  26 51-58
  • 14 Witkowski P T, Schuenadel L, Wiethaus J, Bourquain D R, Kurth A, Nitsche A. Cellular impedance measurement as a new tool for poxvirus titration, antibody neutralization testing and evaluation of antiviral substances.  Biochem Biophys Res Commun. 2010;  401 37-41
  • 15 Amer M E, Shamma M, Freyer A J. The tetracyclic Erythrina alkaloids.  J Nat Prod. 1991;  54 329-363
  • 16 Perrin D R, Whittle C P, Batterham T J. The structure of phaseollidin.  Tetrahedron Lett. 1972;  13 1673-1676
  • 17 Wanjala C C W, Majinda R R T. Two novel glucodienoid alkaloids from Erythrina latissima seeds.  J Nat Prod. 2000;  63 871-873
  • 18 Asomaning W A, Otoo E, Akoto O, Oppong I V, Addae-Mensah I, Waibel R, Achenbach H. Isoflavones and coumarins from Milletia thonningii.  Phytochemistry. 1999;  51 937-941
  • 19 Sarragiotto M H, Leitao H, Marsaioli A J. Erysotrine-N-oxide and erythrartine-N-oxide, two novel alkaloids from Erythrina mulungu.  Can J Chem. 1981;  59 2771-2775
  • 20 Dagne E, Leslie Gunatilaka A A, Kigston D G I, Alemu M, Hofmann G, Johnson R J. Two bioactive pterocarpans from Erythrina burana.  J Nat Prod. 1993;  56 1831-1834
  • 21 Perrin D R, Biggs D R, Cruickshank I A M. Phaseollidin, a phytoalexin from Phaseolus vulgaris: isolation, physiochemical properties and antifungal activity.  Aust J Chem. 1974;  27 1607-1611
  • 22 Innok P, Rukachaisirikul T, Suksamrarn A. Flavanoids and pterocarpans from the bark of Erythrina fusca.  Chem Pharm Bull. 2009;  57 993-996
  • 23 Watjen W, Kulawik A, Suckow-Schnitker A K, Chovolou Y, Rohrig R, Ruhl S, Kampkatter A, Addae-Kyereme J, Wright C W, Passreiter C M. Pterocarpans phaseollin and neorautenol isolated from Erythrina addisoniae induce apoptotic cell death accompanied by inhibition of ERK phosphorylation.  Toxicology. 2007;  242 71-79
  • 24 Rogers K L, Grice I D, Griffiths L R. Modulation of in vitro platelet 5-HT release by species of Erythrina and Cymbopogon.  Life Sci. 2001;  69 1817-1829

Mehrdad Iranshahi, PharmD, PhD, Associate Professor of Pharmacognosy

Department of Pharmacognosy
Pharmacy School
Mashhad University of Medical Sciences

Vakilabad Blvd.

Mashhad 91775-1365

Iran

Telefon: +98 51 18 82 32 55

Fax: +98 51 18 82 32 51

eMail: Iranshahim@mums.ac.ir