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Structural Features of Procyanidin Interactions with Salivary Proteins
Abstract
Procyanidin dimers and trimer C1 were synthesized, whereas (-)-epicatechin O-gallate and B2-3"-O-gallate were isolated from grape seeds. Human saliva was separated into two fractions. One of these was mainly alpha-amylase and the other mainly proline-rich proteins (PRPs). The procyanidin compounds were combined with each of the saliva protein fractions and with bovine serum albumin. The protein-polyphenol interactions were observed using nephelometry. (+)-Catechin had a higher tannin specific activity (TSA) for PRPs than (-)-epicatechin (1.45 versus 0.65 nephelos turbidity units/mg of polyphenol). This indicated the effect of the stereochemistry of flavan-3-ols on their interaction with proteins. Procyanidin dimers linked through a C(4)-C(8) interflavanoid bond had consistently greater TSA than their counterparts with a C(4)-C(6) linkage. Esterification of a galloyl group to the C(3) hydroxyl function of (-)-epicatechin or to the epicatechin moiety of procyanidin dimer B2 increased TSA. This was not as strong an effect for the dimer, probably as a result of the expected "closed" structure of B2-3"-O-gallate.
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Cited by
Biological Activities of Polyphenols from Grapes
Xia, E.-Q., Deng, G.-F., Guo, Y.-J., & Li, H.-B. (2010) · International Journal of Molecular Sciences · doi:10.3390/ijms11020622 · Cited by 1,063
Interactions between Polyphenols and Macromolecules: Quantification Methods and Mechanisms
Le Bourvellec, C., & Renard, C. M. G. C. (2012) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408398.2010.499808 · Cited by 853
Yilmazer-Musa, M., Griffith, A. M., Michels, A. J., Schneider, E., & Frei, B. (2012) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf301147n · Cited by 411
Orosensory-Directed Identification of Astringent Mouthfeel and Bitter-Tasting Compounds in Red Wine
Hufnagel, J. C., & Hofmann, T. (2008) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf073031n · Cited by 324
A review on astringency and bitterness perception of tannins in wine
Ma, W., Guo, A., Zhang, Y., Wang, H., Liu, Y., & Li, H. (2014) · Trends in Food Science & Technology · doi:10.1016/j.tifs.2014.08.001 · Cited by 306
Metadata
- Authors
- de Freitas, V., & Mateus, N.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-01-17
- Volume
- 49
- Issue
- 2
- Pages
- 940-945
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2055584325
- Cited by
- 383
- References
- 0
- FWCI
- 2.61
- Type
- journal article
- Language
- en
- Open access
- closed
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