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. 2012;13(3):2846-2862.
doi: 10.3390/ijms13032846. Epub 2012 Mar 5.

Astragalin from Cassia alata induces DNA adducts in vitro and repairable DNA damage in the yeast Saccharomyces cerevisiae

Samuel Saito  1 , Givaldo Silva  1 , Regineide Xavier Santos  1 , Grace Gosmann  2 , Cristina Pungartnik  1 , Martin Brendel  1
Affiliations

Astragalin from Cassia alata induces DNA adducts in vitro and repairable DNA damage in the yeast Saccharomyces cerevisiae

Samuel Saito et al. Int J Mol Sci. 2012.

Abstract

Reverse phase-solid phase extraction from Cassia alata leaves (CaRP) was used to obtain a refined extract. Higher than wild-type sensitivity to CaRP was exhibited by 16 haploid Saccharomyces cerevisiae mutants with defects in DNA repair and membrane transport. CaRP had a strong DPPH free radical scavenging activity with an IC(50) value of 2.27 μg mL(-1) and showed no pro-oxidant activity in yeast. CaRP compounds were separated by HPLC and the three major components were shown to bind to DNA in vitro. The major HPLC peak was identified as kampferol-3-O-β-d-glucoside (astragalin), which showed high affinity to DNA as seen by HPLC-UV measurement after using centrifugal ultrafiltration of astragalin-DNA mixtures. Astragalin-DNA interaction was further studied by spectroscopic methods and its interaction with DNA was evaluated using solid-state FTIR. These and computational (in silico) docking studies revealed that astragalin-DNA binding occurs through interaction with G-C base pairs, possibly by intercalation stabilized by H-bond formation.

Keywords: Cassia alata; DNA binding; FTIR; Saccharomyces cerevisiae; antioxidant; astragalin.

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Figures

Figure 1
Figure 1
Kaempferol-3-O-β-d-glucopyranoside (astragalin).
Figure 2
Figure 2
Sensitivity to CaRP of haploid yeast strains.
Figure 3
Figure 3
Bio fingerprinting chromatograms for CaRP at 254 nm using 50 μL CaRP (400 μg mL−1) (black line) and the mixed CaRP-DNA solution (red line) at a final concentration of 510 μg mL−1 in BPES buffer. Peaks are numbered according to the LC-microfractionation.
Figure 4
Figure 4
Semi-preparative LC chromatogram of CaRP. F11 is equivalent to peak 11 in the analytical method (HPLC DNA binding).
Figure 5
Figure 5
(a) 1H-NMR and (b) 13C-NMR (APT) of astragalin in MeOD.
Figure 6
Figure 6
Fourier transform intra-red spectroscopy (FTIR) spectra of free DNA (top), DNA-AST (middle) and free astragalin (AST) (bottom).
Figure 7
Figure 7
Docking structure between d(CGCGAATTCGCG)2 (PDB ID:1D30) and AST. (A) Surface representation of d(CGCGAATTCGCG)2 complexes with AST (Display sideways); (B) Close up view of d(CGCGAATTCGCG)2 complexes with AST represented in the stick style. Hydrogen bonds between d(CGCGAATTCGCG)2 and AST were calculated by Chimera software and are drawn in blue lines; (C) Surface representation of d(CGCGAATTCGCG)2 complexes with AST (Display top).
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