Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells

AAF Mourad, S Nakamura, T Ueno, T Minami… - Bioorganic & medicinal …, 2013 - Elsevier
AAF Mourad, S Nakamura, T Ueno, T Minami, T Yagi, H Yasue, R Komatsu, M Yoshikawa…
Bioorganic & medicinal chemistry letters, 2013Elsevier
In a previous study, retrofractamide A from the fruit of Piper chaba was shown to promote
adipogenesis in 3T3-L1 cells. In the present study, retrofractamide A and its derivatives were
synthesized, and their adipogenetic effects in 3T3-L1 cells were examined. Among the
tested compounds, an amide composed of 9-(3′, 4′-methylenedioxyphenyl)-nona-2 E,
4E, 8E-trienoic acid and an n-butyl or n-pentyl amine showed strongest activity. Moreover,
the amide with the n-pentyl amine moiety significantly increased the uptake of 2 …
Abstract
In a previous study, retrofractamide A from the fruit of Piper chaba was shown to promote adipogenesis in 3T3-L1 cells. In the present study, retrofractamide A and its derivatives were synthesized, and their adipogenetic effects in 3T3-L1 cells were examined. Among the tested compounds, an amide composed of 9-(3′,4′-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid and an n-butyl or n-pentyl amine showed strongest activity. Moreover, the amide with the n-pentyl amine moiety significantly increased the uptake of 2-deoxyglucose into the cells, and also increased the mRNA levels of adiponectin, peroxisome proliferator-activated receptor γ2 (PPARγ2), glucose transporter 4 (GLUT4), fatty acid-binding protein (aP2), and CCAAT/enhancer-binding protein (C/EBP) α and β in a similar manner as the PPARγ agonist troglitazone, although it had less agonistic activity against PPARγ.
Elsevier
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