Abstract
In the present study, Lactobacillus plantarum glycolipid (GL1) molecule in β-configuration and its fatty acid analogues were synthesized using trichloroacetimidate methodology. The β-configuration of the GL1 molecule was unambiguously assigned by NMR studies using 2D-ROESY (NOE) and J-coupling analysis. Dihydrosterculic acid was synthesized using Furukawa's reagent and the selective esterification of dihydrosterculic acid at C-3 position of glycerol was achieved with EDC-HCl at 0 °C. In vitro cytotoxicity of the GL1 molecule and its fatty acid analogues was evaluated against DU145, A549, SKOV3 and MCF7 cell lines. Among all the synthesized molecules, the GL1 molecule and compound 7d showed moderate activity, while the compound 7b showed promising activity against all the tested cell lines with IC50 values of 20.1, 18.2, 19.1 and 17.6 μM, respectively. In addition, all tested compounds showed poor cytotoxicity against normal HUVEC cells. The MCF7 cells when treated with compound 7b showed lower bromodeoxyuridine incorporation levels as compared to untreated cells, suggesting that the compound 7b was highly effective and inhibited the cell proliferation. In addition, the compounds showed significant increase in caspases 3 and 9 l...Continue Reading
References
Jan 1, 1973·Antonie van Leeuwenhoek·J H Huis in 't Veld, J M Willers
Dec 16, 1983·Journal of Immunological Methods·T Mosmann
Sep 1, 1993·Chemical & Pharmaceutical Bulletin·H ShirahashiA Iwashima
Jun 24, 1996·Cancer Letters·H TokudaJ Sakakibara
May 14, 1998·Chemistry & Biology·N A Thornberry
Feb 5, 2000·Bioorganic & Medicinal Chemistry·R KatochR S Phadke
May 2, 2000·Journal of Biochemistry·K Nakata
Mar 20, 2003·Bioorganic & Medicinal Chemistry Letters·Akito Tanaka, Tomoyuki Nishizaki
Nov 6, 2003·Phytochemistry·Wicharn JanwitayanuchitTirayut Vilaivan
Jan 12, 2005·European Journal of Medicinal Chemistry·Diego ColomboHarukuni Tokuda
Jan 22, 2005·Journal of Medicinal Chemistry·Hao ChengPeng George Wang
Jul 1, 2006·Lipids·Gerhard Knothe
May 15, 2007·European Journal of Medicinal Chemistry·Francesca CateniElena Banfi
Feb 6, 2008·The Journal of Cell Biology·Geertrui DeneckerWim Declercq
Jun 24, 2008·Journal of Natural Products·Eric H AndrianasoloPaul Falkowski
Feb 10, 2010·Chemistry : a European Journal·Gunthard StübsJörg Rademann
May 24, 2011·Carbohydrate Research·Vince PozsgayRachel Schneerson
Sep 20, 2011·Organic & Biomolecular Chemistry·Shenglou DengPaul B Savage
Jun 12, 2012·Carbohydrate Research·Janelle SauvageauMattie S M Timmer
Apr 10, 2013·The Journal of Organic Chemistry·Naoki MichihataHidetoshi Yamada