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Relationship between the biological activities of methylated derivatives of (-)-epigallocatechin-3-O-gallate (EGCG) and their cell surface binding activities. 2007

Satomi Yano, and Yoshinori Fujimura, and Daisuke Umeda, and Toshio Miyase, and Koji Yamada, and Hirofumi Tachibana
Laboratory of Food Chemistry, Division of Applied Biological Chemistry, Department of Bioscience and Biotechnology, Faculty of Agriculture, Kyushu University, 6-10-1 Hakozaki, Fukuoka, Japan.

It was previously reported that (-)-epigallocatechin-3-O-gallate (EGCG) suppresses the expression of the high-affinity IgE receptor FcepsilonRI in human basophilic cells and that this suppressive effect is associated with EGCG binding to the cell surface. This study examined the effects of five methylated derivatives of EGCG, (-)-epigallocatechin-3-O-(3-O-methyl)gallate (EGCG 3' 'Me), (-)-epigallocatechin-3-O-(4-O-methyl)gallate (EGCG 4' 'Me), (-)-4'-O-methyl-epigallocatechin-3-O-gallate (EGCG 4'Me), (-)-epigallocatechin-3-O-(3,4-O-methyl)gallate (EGCG 3' '4' 'diMe), and (-)-4'-O-methyl-epigallocatechin-3-O-(4-O-methyl)gallate (EGCG 4'4' 'diMe) on FcepsilonRI expression and ERK1/2 phosphorylation, and each of their cell surface binding activities was measured. Of these five methylated derivatives, three that are methylated at the 3' '- and/or 4' '-position, EGCG 3' 'Me, EGCG 4' 'Me, and EGCG 3' '4' 'diMe, suppressed FcepsilonRI expression and ERK1/2 phosphorylation, although the suppressive effects were lower than that of EGCG. EGCG 4'Me and EGCG 4'4' 'diMe, both of which are methylated at the 4'-position, did not demonstrate a suppressive effect. Furthermore, it was found that EGCG 3' 'Me, EGCG 4' 'Me, EGCG 3' '4' 'diMe, and EGCG 4'Me, which are methylated at the 3' '- and/or 4' '-positions or the 4'-position, could bind to the cell surface even though their binding activities were lower than that of EGCG. Only EGCG 4'4' 'diMe, which is methylated at both the 4'- and 4' '-positions, could not bind. These results suggest that the trihydroxyl structure of the B ring is essential for EGCG to exert the suppressive effects and that the hydroxyl groups on both the 4'-position in the B ring and the 4' '-position in the gallate are crucial for the cell surface binding activity of EGCG.

UI MeSH Term Description Entries
D008745 Methylation Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed) Methylations
D010766 Phosphorylation The introduction of a phosphoryl group into a compound through the formation of an ester bond between the compound and a phosphorus moiety. Phosphorylations
D002392 Catechin An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Catechinic Acid,Catechuic Acid,(+)-Catechin,(+)-Cyanidanol,(+)-Cyanidanol-3,(-)-Epicatechin,(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol,2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)-,3,3',4',5,7-Flavanpentol,Catergen,Cianidanol,Cyanidanol-3,Epicatechin,KB-53,Z 7300,Zyma,Cyanidanol 3,KB 53,KB53
D002460 Cell Line Established cell cultures that have the potential to propagate indefinitely. Cell Lines,Line, Cell,Lines, Cell
D002462 Cell Membrane The lipid- and protein-containing, selectively permeable membrane that surrounds the cytoplasm in prokaryotic and eukaryotic cells. Plasma Membrane,Cytoplasmic Membrane,Cell Membranes,Cytoplasmic Membranes,Membrane, Cell,Membrane, Cytoplasmic,Membrane, Plasma,Membranes, Cell,Membranes, Cytoplasmic,Membranes, Plasma,Plasma Membranes
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D001491 Basophils Granular leukocytes characterized by a relatively pale-staining, lobate nucleus and cytoplasm containing coarse dark-staining granules of variable size and stainable by basic dyes. Basophil
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D048052 Mitogen-Activated Protein Kinase 3 A 44-kDa extracellular signal-regulated MAP kinase that may play a role the initiation and regulation of MEIOSIS; MITOSIS; and postmitotic functions in differentiated cells. It phosphorylates a number of TRANSCRIPTION FACTORS; and MICROTUBULE-ASSOCIATED PROTEINS. Extracellular Signal-Regulated Kinase 1,ERK1 Kinase,MAPK3 Mitogen-Activated Protein Kinase,Meiosis-Activated Myelin Basic Protein Kinase p44(mpk),Microtubule-Associated Protein-2 Kinase,PSTkinase p44mpk,Protein-Serine-Threonine Kinase p44(mpk),p44 MAPK,Extracellular Signal Regulated Kinase 1,Kinase, ERK1,Kinase, Microtubule-Associated Protein-2,MAPK3 Mitogen Activated Protein Kinase,Microtubule Associated Protein 2 Kinase,Mitogen Activated Protein Kinase 3,p44mpk, PSTkinase
D019950 Mitogen-Activated Protein Kinase 1 A proline-directed serine/threonine protein kinase which mediates signal transduction from the cell surface to the nucleus. Activation of the enzyme by phosphorylation leads to its translocation into the nucleus where it acts upon specific transcription factors. p40 MAPK and p41 MAPK are isoforms. Extracellular Signal-Regulated Kinase 2,MAP Kinase 2,Mitogen-Activated Protein Kinase 2,p42 MAP Kinase,p42 MAPK,p42(Mitogen-Activated Protein Kinase),MAPK1 Mitogen-Activated Protein Kinase,MAPK2 Mitogen-Activated Protein Kinase,p42(Mapk),p42(Mapk) Kinase,Extracellular Signal Regulated Kinase 2,MAP Kinase, p42,MAPK1 Mitogen Activated Protein Kinase,MAPK2 Mitogen Activated Protein Kinase,Mitogen Activated Protein Kinase 1,Mitogen Activated Protein Kinase 2

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