title: O-methylated theaflavins suppress the intracellular accumulation of triglycerides from terminally differentiated human visceral adipocytes.
abstract: A known O-methylated theaflavin, theaflavin 3-O-(3-O-methyl)gallate (3MeTF3G), and the new theaflavin 3-O-(3,5-di-O-methyl)gallate (3,5diMeTF3G) were synthesized via the O-methylation of theaflavin 3-O-gallate (TF3G). Both 3MeTF3G and 3,5diMeTF3G are more stable than TF3G at pH 7.5 in the order 3,5diMeTF3G > 3MeTF3G > TF3G. The inhibitory effects of these compounds on the intracellular accumulation of triglycerides from terminally differentiated human visceral adipocytes were investigated. Compound 3MeTF3G exhibited an inhibitory effect similar to that of TF3G at 3 μM and a slightly lower effect than that of TF3G at 10 μM. The result suggested that the degradants and oxidatively polymerized products of TF3G may also have inhibitory effects. For cells treated with 3,5diMeTF3G at 3 and 10 μM, intracellular triglyceride accumulation was dose dependent and significantly lower compared with that for other compounds. It was suggested that the higher effect of 3,5diMeTF3G was due to its higher stability and likely improved absorption owing to di-O-methylation.
authors.affiliation: Research Laboratories for Fundamental Technology of Food, Asahi Group Holdings, Limited, 1-21 Midori 1-chome, Moriya-shi, Ibaraki 302-0106, Japan.
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Tanaka
authors.forename: Masanobu
authors.initials: M
authors.lastname: Kirita
authors.forename: Satoshi
authors.initials: S
authors.lastname: Miyata
authors.forename: Yuko
authors.initials: Y
authors.lastname: Abe
authors.forename: Motoyuki
authors.initials: M
authors.lastname: Tagashira
authors.forename: Tomomasa
authors.initials: T
authors.lastname: Kanda
authors.forename: Mari
authors.initials: M
authors.lastname: Maeda-Yamamoto
mesh_terms: D017667:Adipocytes / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism*; D044946:Biflavonoids / Q000737:chemistry / Q000494:pharmacology*; D002392:Catechin / Q000737:chemistry / Q000494:pharmacology*; D002454:Cell Differentiation; D015536:Down-Regulation / Q000187:drug effects; D006801:Humans; D050152:Intra-Abdominal Fat / Q000166:cytology* / Q000378:metabolism; D008745:Methylation; D014280:Triglycerides / Q000378:metabolism*
chemical_list: D044946:Biflavonoids; D014280:Triglycerides; C056068:theaflavin; D002392:Catechin