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The impact of human metabolism on the bioactivity of anthocyanins

Published online by Cambridge University Press:  19 October 2012

C. Czank ,
R. De Ferrars ,
H. Amin ,
P. A. Kroon ,
Q. Zhang ,
K. Kalowole ,
N. Botting ,
A. Cassidy  and
C. D. Kay
C. Czank
Affiliation:
Department of Nutrition, Norwich Medical School, University of East Anglia, Norwich, NR47TJ
R. De Ferrars
Affiliation:
Department of Nutrition, Norwich Medical School, University of East Anglia, Norwich, NR47TJ
H. Amin
Affiliation:
Department of Nutrition, Norwich Medical School, University of East Anglia, Norwich, NR47TJ
P. A. Kroon
Affiliation:
Institute of Food Research, Norwich, NR47UA
Q. Zhang
Affiliation:
School of Chemistry, University of St Andrews, KY1 69AJ, Scotland, UK
K. Kalowole
Affiliation:
School of Chemistry, University of St Andrews, KY1 69AJ, Scotland, UK
N. Botting
Affiliation:
School of Chemistry, University of St Andrews, KY1 69AJ, Scotland, UK
A. Cassidy
Affiliation:
Department of Nutrition, Norwich Medical School, University of East Anglia, Norwich, NR47TJ
C. D. Kay
Affiliation:
Department of Nutrition, Norwich Medical School, University of East Anglia, Norwich, NR47TJ
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Abstract

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Proceedings of the Nutrition Society , Volume 71 , Issue OCE2: Summer Meeting hosted by the Irish Section, 16–19 July 2012, Translational nutrition: integrating research, practice and policy , 2012 , E181
Copyright
Copyright © The Authors 2012

Diet derived anthocyanins (ACN) such as cyanidin-3-glucoside (C3G) are believed to reduce the risk of cardiovascular disease (CVD)( Reference Cassidy, O'Reilly and Kay 1 , Reference Hooper, Kroon and Rimm 2 ) despite their apparent low bioavailability( Reference Kay 3 ). However, given that ACN are likely to degrade following ingestion, their degradation products and metabolites are likely to contribute to their bioactivity( Reference Kay, Kroon and Cassidy 4 ).

In our recently completed human feeding study in which stable isotope labelled C3G was fed to healthy male participants (500 mg bolus of 13C5–C3G; n=8), a total of 22 metabolites were identified. This included protocatachuic acid (PCA) which had a CMax of 0.23±0.12 μM and its methylated derivative vanillic acid (VA) which had a CMax of 0.66±0.41 μM. We explored the bioactivity of these metabolites on vascular health by measuring the effects on mediators of nitric oxide bioavailability including endothelial nitric oxide synthase (eNOS), NADPH oxidase (NOX4) and superoxide. Protein expression of eNOS was measured by ELISA and NOX4 by western blotting, while superoxide was measured indirectly via ferrocytochrome C oxidation (A550) in cultured human umbilical cord vascular endothelial cells treated with either 0.1, 1 or 10 μM of C3G, PCA or VA.

Values are given as percentage relative to control and are the mean of 3 independent experiments *P<0.05 (ANOVA with Tukey Kramer test, n=3).

C3G significantly increased eNOS at a concentration of 10 μM and significantly decreased superoxide at 0.1 and 1 μM but had no effect on NOX4 protein expression. PCA signficantly decreased eNOS protein at all concentrations tested, reduced NOX4 protein at 1 μM and decreased superoxide at 0.1 and 10 μM. VA significantly increased eNOS at 0.1 and 10 μM, but did not affect NOX4 expression or superoxide production. These studies provide early evidence that metabolites of anthocyanins may exhibit greater bioactivity than the parent molecule. In addition, these activities are apparent at relatively low and dietary achievable concentrations.

This work was supported by Biotechnology and Biological Sciences Research Council Diet and Health Industry Club.

References

1. Cassidy, A, O'Reilly, A, Kay, C et al. (2011) Am Soc Nutrition 93, 338–47.Google Scholar
2. Hooper, L, Kroon, PA, Rimm, EB et al. (2008) Am Soc Nutrition 88, 38–46.Google Scholar
3. Kay, CD (2006) Nutr Res Rev 19, 137–46.CrossRefGoogle Scholar
4. Kay, CD, Kroon, PA, Cassidy, A (2009) Mol Nutr Food Res 53, S92–S101.CrossRefGoogle Scholar