Analysis of 5-hydroxyisoflavones by surface-enhanced Raman spectroscopy : genistein and methoxy derivatives

Sekine, Ryo, Vongsvivut, Jitraporn, Robertson, Evan G., Spiccia, Leone and McNaughton, Don 2011, Analysis of 5-hydroxyisoflavones by surface-enhanced Raman spectroscopy : genistein and methoxy derivatives, Journal of physical chemistry b, vol. 115, no. 47, pp. 13943-13954.

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Title Analysis of 5-hydroxyisoflavones by surface-enhanced Raman spectroscopy : genistein and methoxy derivatives
Author(s) Sekine, Ryo
Vongsvivut, Jitraporn
Robertson, Evan G.
Spiccia, Leone
McNaughton, Don
Journal name Journal of physical chemistry b
Volume number 115
Issue number 47
Start page 13943
End page 13954
Total pages 12
Publisher American Chemical Society
Place of publication Washington D.C.
Publication date 2011
ISSN 1520-6106
1520-5207
Keyword(s) physical chemistry
isoflavones
nanoparticle
solubility
Summary 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.
Language eng
Field of Research 030101 Analytical Spectrometry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1 Refereed article in a scholarly journal
Copyright notice ©2011, American Chemical Society
Persistent URL http://hdl.handle.net/10536/DRO/DU:30038955

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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