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Molecular Mechanism by Which Tea Catechins Decrease the Micellar Solubility of Cholesterol
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DOI：10.1021/acs.jafc.9b02265.png)
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Tea polyphenols lower the levels of cholesterol in the blood by decreasing the cholesterol micellar solubility. To clarify this mechanism, the interactions between taurocholic acid and (-)-epigallocatechin gallate (EGCg) and its derivatives were investigated. C-13 NMR studies revealed remarkable chemical-shift changes for the carbonyl carbon atom and the 1 ''- and 4 ''-positions in the galloyl moiety. Furthermore, H-1 NMR studies using (-)-EGCg derivatives showed that the number of hydroxyl groups on the B ring did not affect these interactions, whereas the carbonyl carbon atom and the aromatic ring of the galloyl moiety had remarkable effects. The configuration at the 2- and 3-positions of the catechin also influenced these interactions, with the trans-configuration resulting in stronger inhibition activity than the cis-configuration. Additionally, a 1:1 component ratio for the catechin-taurocholic acid complex was determined by electrospray ionization-mass spectrometry. These molecular mechanisms contribute to the development of cholesterol-absorption inhibitors.
Keyword:
tea (Camellia sinensis)
catechin
cholesterol
micellar solubility
taurocholic acid
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6.2
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4.5W
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15.3W
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