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DOI: 10.1055/s-0031-1298310
© Georg Thieme Verlag KG Stuttgart · New York
Cytotoxic Evaluation of Alkaloids and Isoflavonoids from the Australian Tree Erythrina vespertilio
Publication History
received Nov. 26, 2011
revised February 1, 2012
accepted February 2, 2012
Publication Date:
21 February 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.
Key words
Erythrina vespertilio Benth. - Fabaceae - PC3 - prostate cancer - vespertilioside - xCELLigence
References
- 1
Mbafor J T, Ndom J C, Fomum Z T.
Erythrina studies 33. Triterpenoid saponins from Erythrina sigmoidea.
Phytochemistry.
1997;
44
1151-1155
MissingFormLabel
- 2
Tanaka H, Tanaka T, Etoh H.
Three pterocarpans from Erythrina crista-galli.
Phytochemistry.
1997;
45
835-838
MissingFormLabel
- 3
Chawla A S, Jackson A H.
Erythrina and related alkaloids.
Nat Prod Rep.
1984;
1
371-373
MissingFormLabel
- 4
Ozawa M, Kishida A, Ohsaki A.
Erythrinan alkaloids from seeds of Erythrina velutina.
Chem Pharm Bull.
2011;
59
564-567
MissingFormLabel
- 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
MissingFormLabel
- 6
Innok P, Rukachaisirikul T, Suksamrarn A.
Flavanoids and pterocarpans from the bark of Erythrina fusca.
Chem Pharm Bull.
2009;
57
993-996
MissingFormLabel
- 7
Chong P, Rashid P.
Can we prevent prostate cancer?.
Aust Fam Physician.
2005;
34
265-267
MissingFormLabel
- 8
Grothaus P G, Cragg G M, Newman D J.
Plant natural products in anticancer drug discovery.
Curr Org Chem.
2010;
14
1781-1791
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 15
Amer M E, Shamma M, Freyer A J.
The tetracyclic Erythrina alkaloids.
J Nat Prod.
1991;
54
329-363
MissingFormLabel
- 16
Perrin D R, Whittle C P, Batterham T J.
The structure of phaseollidin.
Tetrahedron Lett.
1972;
13
1673-1676
MissingFormLabel
- 17
Wanjala C C W, Majinda R R T.
Two novel glucodienoid alkaloids from Erythrina latissima seeds.
J Nat Prod.
2000;
63
871-873
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 22
Innok P, Rukachaisirikul T, Suksamrarn A.
Flavanoids and pterocarpans from the bark of Erythrina fusca.
Chem Pharm Bull.
2009;
57
993-996
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
Mehrdad Iranshahi, PharmD, PhD, Associate Professor of Pharmacognosy
Department of Pharmacognosy
Pharmacy School
Mashhad University of Medical Sciences
Vakilabad Blvd.
Mashhad 91775-1365
Iran
Phone: +98 51 18 82 32 55
Fax: +98 51 18 82 32 51
Email: Iranshahim@mums.ac.ir