Mechanism of Creaming Down Based on Chemical Characterization of a Complex of Caffeine and Tea Catechins
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- Ishizu Takashi
- Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University
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- Tsutsumi Hiroyuki
- Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University
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- Sato Takashi
- Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University
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The component of a precipitate resulting from creaming down, which was made from caffeine and a catechin mixture, was determined by an integrated value of H2 proton signals of tea catechins in the quantitative 1H-NMR spectrum. The results showed that gallate-type catechins formed a precipitate by creaming down more predominantly than non-gallate-type catechins. X-ray crystallographic analysis showed that the gallate-type catechin (−)-epigallocatechin-3-O-gallate (EGCg), (−)-epicatechin-3-O-gallate (ECg) formed 2 : 2 and 2 : 4 complexes with caffeine, respectively, and the non-gallate-type catechin (−)-epicatechin (EC) and caffeine formed a 1 : 1 complex. The 2 : 2, 2 : 4 complexes of caffeine and EGCg, ECg formed a hydrophobic space with three aromatic A, B, and B′ rings of two EGCg, ECg molecules, and one caffeine molecule was captured in this hydrophobic space. However, no such hydrophobic space in the 1 : 1 complex of caffeine and EC formed. It was thought that the hydrophobicity of the 2 : 2, 2 : 4 complexes of caffeine and EGCg, ECg was stronger than that of the 1 : 1 complex of caffeine and EC, with the result that the 2 : 2, 2 : 4 complexes of caffeine and EGCg, ECg precipitated by creaming down more predominantly than the 1 : 1 complex of caffeine and EC in an aqueous solution. Furthermore, the molecular capture of various heterocyclic compounds by formation of the 2 : 2 complex of EGCg from the aqueous solution was investigated using the quantitative 1H-NMR spectrum.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 64 (7), 676-686, 2016
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204179158784
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- NII論文ID
- 130005160080
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 027451364
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- PubMed
- 27373623
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可