Structural modifications of plumieride isolated from Plumeria bicolor and the effect of these modifications on in vitro anticancer activity

The Journal of Organic Chemistry
Mahabeer P DobhalR K Pandey

Abstract

Plumieride was isolated as one of the major components from the biologically active methanolic extract of the bark of Plumeria bicolor (family Apocynaceae). For investigating the effect of substituents on cytotoxic activity it was modified into a series of compounds. Replacing the methyl ester functionality of plumieride with alkyl amides of variable carbon units improved the cytotoxic activity, and a correlation between overall lipophilicity and cytotoxic activity was observed. In plumieride, the glucose moiety was converted into a di- and trisaccharide by following the protection and deprotection approach, and the resulting compounds produced enhanced cytotoxicity. However, these compounds were found to be less effective than plumeiride containing a dodecyl (12 carbon units) amide group. Among all of the derivatives, the naturally occurring plumieride showed the least cytotoxicity (50% cell kill = 49.5 microg/mL), and the dodecyl amide analogue of plumieridepentaacetate produced the best efficacy (50% cell kill = 11.8 microg/mL). The di- and trisaccharide analogues were found to be slightly less effective than the dodecyl derivative (50% cell kill = 15-17 microg/mL). The in vitro cytotoxicity of the plumieride analogues was d...Continue Reading

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Citations

Dec 27, 2011·The Indian Journal of Medical Research·Umakant SharmaSarman Singh
Jan 1, 2014·Antioxidants·Dharmendra SinghRadhey Shyam Gupta
Jun 23, 2011·Journal of Ethnopharmacology·Sebastião de Oliveira RebouçasAlexandre de B F Ferraz
Dec 29, 2006·Chemistry & Biodiversity·Brigitta ElsässerTibor Kurtán
Mar 16, 2013·Chemistry & Biodiversity·Nisha AgrawalMahabeer P Dobhal
Apr 9, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Olga WesołowskaKamila Środa-Pomianek
May 2, 2018·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Thaise BoeingSérgio Faloni de Andrade

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