Journal article
Analysis of 5-hydroxyisoflavones by surface-enhanced raman spectroscopy: Genistein and methoxy derivatives
Journal of Physical Chemistry B, Vol.115(47), pp.13943-13954
2011
PMID: 22010824
Abstract
A series of 5-hydroxy-isoflavones-genistein, biochanin A, prunetin, and 4′,7-dimethoxygenistein-have been studied by surface-enhanced Raman spectroscopy (SERS). Citrate reduced silver colloids were employed as a standard technique to measure SER spectra over a range of pH and concentrations. Density functional theory calculations were used to assist in determining the mode of interaction of isoflavones with the silver nanoparticles. It is revealed that biochanin A and prunetin interact with the silver nanoparticles upon deprotonation of the 7- and the 4′-OH groups, respectively, to show SERS activity. Correlations of their spectra with SERS of genistein strongly support the presence of multiple interaction modes involving both of the OH groups in genistein, in a similar manner to daidzein. Surprisingly, however, under these conditions, the 5-OH group was found to be noninteractive as revealed by attempts to measure SERS of 4′,7-dimethoxygenistein. This was attributed partly to the low solubility and, more importantly, to the influence of steric hindrance, caused by the position of the pendant phenyl ring, which prevented interaction with the Ag colloid surface. These results complement recent work on daidzein and formononetin and provide further insight into understanding the SER spectra of isoflavones.
Details
- Title
- Analysis of 5-hydroxyisoflavones by surface-enhanced raman spectroscopy: Genistein and methoxy derivatives
- Authors
- Ryo Sekine (Author) - Monash UniversityJitraporn Vongsvivut (Author) - Deakin UniversityEvan G Robertson (Author) - La Trobe UniversityLeone Spiccia (Author) - Monash UniversityDon McNaughton (Author) - Monash University
- Publication details
- Journal of Physical Chemistry B, Vol.115(47), pp.13943-13954
- Publisher
- American Chemical Society
- Date published
- 2011
- DOI
- 10.1021/jp207730g
- ISSN
- 1520-6106; 1520-5207; 1520-6106
- PMID
- 22010824
- Organisation Unit
- University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering
- Language
- English
- Record Identifier
- 99513873002621
- Output Type
- Journal article
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- Chemistry, Physical
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