122271-47-0Relevant academic research and scientific papers
Stereocontrolled total syntheses of optically active furofuran lignans
Inai, Makoto,Ishikawa, Ryo,Yoshida, Naoto,Shirakawa, Nana,Akao, Yusuke,Kawabe, Yusuke,Asakawa, Tomohiro,Egi, Masahiro,Hamashima, Yoshitaka,Kan, Toshiyuki
, p. 3513 - 3521 (2015/11/17)
Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through l-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.
Anticancer effects of the metabolic products of the resveratrol analogue, DMU-212: Structural requirements for potency
Androutsopoulos, Vasilis P.,Ruparelia, Ketan C.,Papakyriakou, Athanasios,Filippakis, Harilaos,Tsatsakis, Aristeidis M.,Spandidos, Demetrios A.
experimental part, p. 2586 - 2595 (2011/06/21)
The methoxylated trans-stilbene resveratrol analogue, (E)-3,4,5,4′- tetramethoxystilbene (1), has shown promising antiproliferative activity in in vitro cell line and in vivo models. In vivo 1 gives rise to several metabolic products through demethylation or hydroxylation reactions at the stilbene moiety. In the present study we examined the anticancer activity of 1 and the metabolites (E)-3′-hydroxy-3,4,5,4′-tetramethoxystilbene (2), (E)-4′-hydroxy-3,4,5-trimethoxystilbene (3), (E)-4-hydroxy-3,5,4′- trimethoxystilbene (4) and (E)-3-hydroxy-4,5,4′-trimethoxystilbene (5) by means of cell viability testing, cell cycle analysis, immunostaining and Western blotting. Compounds 1 and 2 exhibited submicromolar toxicity in MCF-7 breast adenocarcinoma and HepG2 hepatoma cells, whereas 3, 4 and 5 were inactive in terms of inhibition of cellular proliferation. Incubation with 1 or 2 at 10 μM for 24 h induced apoptosis and G2/M cell cycle arrest in MCF-7 and HepG2 cells. Immunostaining of MCF-7 cells for β-tubulin in the presence of either 1 or 2 revealed shorter localization of the protein around the nucleus, as compared to control cells. Western blot analyses further demonstrated that treatment with either 1 or 2 at concentrations between 30 and 50 μM for 24 h caused a downregulation in the levels of β-tubulin and cyclin D1 expression and an upregulation in the levels of p53 expression in MCF-7 and HepG2 cells. 2 further increased the ratio of mRNA levels of the apoptosis-related genes Bax/Bcl-xL in both MCF-7 and HepG2 cells in a dose-dependent manner. We conclude that 2 inhibits HepG2 and MCF-7 cellular proliferation by inducing apoptosis and G2/M arrest through p53 and Bax/Bcl-xL upregulation. Our findings further demonstrate that trimethoxy substitutions along with the presence of a methoxy group at position 4′ are necessary for retaining the activity of 1.
Isolation, Structure, and Synthesis of Combretastatin C-1
Singh, Sheo Bux,Pettit, George R.
, p. 4105 - 4114 (2007/10/02)
A new cell growth inhibitory (PS ED50 2.2 μg/mL) phenanthraquinone designated combretastatin C-1 (2) has been isolated from the African tree Combretum caffrum.The structure (2) assigned combretastatin C-1 was based on high-resolution mass and NMR spectral analyses and confirmed by total syntheses.Synthetic routes 5b -> 6b -> 2 and especially 5c -> 6c -> 2 proved to be quite practical.
