The Effect of Secoisolariciresinol on 3T3-L1 Adipocytes and the Relationship between Molecular Structure and Activity.
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.
Tominaga
Shiori
S
Faculty of Agriculture, Ehime University.
Sugahara
Takuya
T
Nishimoto
Sogo
S
Yamawaki
Manami
M
Nakashima
Yuki
Y
Kishida
Taro
T
Akiyama
Koichi
K
Maruyama
Masafumi
M
Yamauchi
Satoshi
S
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
D052242:Adiponectin; D002072:Butylene Glycols; D004967:Estrogens; D017705:Lignans; D014280:Triglycerides; C060283:secoisolariciresinol