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

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タイトル: Association of Tannins and Related Polyphenols with the Cyclic Peptide Gramicidin S
著者: Zhang, Ying-Jun / Tanaka, Takashi / Betsumiya, Yayoi / Kusano, Rie / Matsuo, Atsushi / Ueda, Toshihisa / Kouno, Isao
発行日: 2002年 2月
出版者: Pharmaceutical Society of Japan
引用: Chemical & Pharmaceutical Bulletin v.50(2) p.258-262, 2002
抄録: 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.
キーワード: 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
関連リンク : http://dx.doi.org/10.1248/cpb.50.258
資料タイプ: Journal Article
原稿種類: publisher
出現コレクション:050 学術雑誌論文

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



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