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标题：Development of High-Order Functions Using (−)-Epigallocatechin-3-O-gallate in Water
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作者：Takashi Ishizu
期刊名称：Chemical and Pharmaceutical Bulletin
印刷版ISSN：0009-2363
电子版ISSN：1347-5223
出版年度：2020
卷号：68
期号：12
页码：1143-1154
DOI：10.1248/cpb.c20-00197
出版社：The Pharmaceutical Society of Japan
摘要：The high-order functions of molecular capture and chiral recognition of tea gallated catechins (−)-epigallocatechin-3- O -gallate (EGCg) in water were investigated. A solution of equimolar amounts of a variety of heterocyclic compounds and EGCg in water afforded adhesive precipitates containing the heterocyclic compounds and EGCg at a molar ratio of 1 : 1, based on the integrated value of NMR proton signals. The molecular capture abilities of a variety of heterocyclic compounds using EGCg from the aqueous solutions were evaluated with the ratios of the heterocyclic compounds included in the precipitates of EGCg complex to the total heterocyclic compounds used. In the 1 H-NMR spectrum of a solution containing cyclo(L-Pro-Gly), cyclo(D-Pro-Gly), and EGCg in a D 2 O solution, a difference in the chemical shift of the 1 H-NMR signal for some protons of the Pro residue was observed. Judging from the crystal structures of the 2 : 2 EGCg complexes of cyclo(L-Pro-Gly), cyclo(D-Pro-Gly), the difference in the chemical shift derived mainly from a magnetic anisotropic shielding effect by the ring current from the B ring of EGCg.In the 1 H-NMR spectrum of a solution containing the pharmaceuticals racemic ( R , S )-propranolol, ( R , S )-diprophylline, ( R , S )-proxyphylline and EGCg in D 2 O, splitting of the 1 H-NMR signals of the pharmaceuticals was observed. It was suggested that the pharmaceuticals formed diastereomers of EGCg complexes, as a result chirality of the pharmaceuticals was recognized by EGCg in the D 2 O solution.
关键词：(−)-epigallocatechin-3-O-gallate;propranolol;diprophylline;proxyphylline;quantitative 1H-NMR;X-ray crystallographic analysis