title: The Effect of Secoisolariciresinol on 3T3-L1 Adipocytes and the Relationship between Molecular Structure and Activity.
abstract: As we have reported, flaxseed lignan, (+)-secoisolariciresinol (SECO), (-)-SECO, and meso-SECO were stereoselectively synthesized and their biological functions were evaluated. In the present study, we focused on the effects of SECOs on the regulation of 3T3-L1 adipocytes, and identified the structure-activity relationships. Optically active SECO and meso-SECO were tested for their effects on lipid metabolism in 3T3-L1 adipocytes. (-)-SECO accelerated adiponectin production of 3T3-L1 adipocytes. On the other hand, (+)- and meso-SECO suppressed the production of adiponectin. In addition, triglyceride (TG) accumulation in 3T3-L1 adipocytes was significantly suppressed by all three SECOs tested here, as was 17beta-estradiol, when the SECOs were added to the medium during induction of 3T3-L1 preadipocytes to adipocytes. Especially, (-)-SECO strongly reduced TG accumulation. It is well-known that SECO has estrogen-like activity. Hence the estrogen-like activity of each SECO compound was assessed. Only (-)-SECO had estrogen-like activity.
authors.affiliation: Faculty of Agriculture, Ehime University.
authors.forename: Shiori
authors.initials: S
authors.lastname: Tominaga
authors.forename: Takuya
authors.initials: T
authors.lastname: Sugahara
authors.forename: Sogo
authors.initials: S
authors.lastname: Nishimoto
authors.forename: Manami
authors.initials: M
authors.lastname: Yamawaki
authors.forename: Yuki
authors.initials: Y
authors.lastname: Nakashima
authors.forename: Taro
authors.initials: T
authors.lastname: Kishida
authors.forename: Koichi
authors.initials: K
authors.lastname: Akiyama
authors.forename: Masafumi
authors.initials: M
authors.lastname: Maruyama
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
mesh_terms: D041721:3T3-L1 Cells; D017667:Adipocytes / Q000166:cytology / Q000187:drug effects*; D052242:Adiponectin / Q000096:biosynthesis; D000818:Animals; D002072:Butylene Glycols / Q000494:pharmacology*; D004967:Estrogens; D017705:Lignans / Q000494:pharmacology*; D050356:Lipid Metabolism / Q000187:drug effects; D051379:Mice; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014280:Triglycerides / Q000096:biosynthesis
chemical_list: D052242:Adiponectin; D002072:Butylene Glycols; D004967:Estrogens; D017705:Lignans; D014280:Triglycerides; C060283:secoisolariciresinol