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Association of Tannins and Related Polyphenols with the Cyclic Peptide Gramicidin S

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Title: Association of Tannins and Related Polyphenols with the Cyclic Peptide Gramicidin S
Authors: Zhang, Ying-Jun / Tanaka, Takashi / Betsumiya, Yayoi / Kusano, Rie / Matsuo, Atsushi / Ueda, Toshihisa / Kouno, Isao
Issue Date: Feb-2002
Publisher: Pharmaceutical Society of Japan
Citation: Chemical & Pharmaceutical Bulletin v.50(2) p.258-262, 2002
Abstract: The association of 10 different tannins and related polyphenols with gramicidin S, a cyclic peptide having a rigid β-turn structure, has been examined using 1H-NMR spectroscopy. In the presence of pentagalloylglucose and epigallocatechin-3-O-gallate, the proton signals due to proline and the adjacent phenylalanine moieties selectively shifted to up field, suggesting a regioselective association with the β-turn structure. The association was also supported by the observation of intermolecular nuclear Overhauser effects between epigallocatechin-3-O-gallate and the peptide. In contrast, ellagitannins, biogenetically derived from pentagalloylglucose, showed small and non-selective chemical shift changes, suggesting that interaction with these tannins is relatively weak. The hydrophobicity of the tannin molecules and the steric hindrance of the interaction site are thought to be important in the association.
Keywords: polyphenol / β-turn / hydrophobic / tannin / peptide / epigallocatechin 3-O-gallate
URI: http://hdl.handle.net/10069/8407
ISSN: 00092363
DOI: 10.1248/cpb.50.258
PubMed ID: 11848219
Relational Links: http://dx.doi.org/10.1248/cpb.50.258
Type: Journal Article
Text Version: publisher
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/8407

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