- Design, synthesis and cytotoxic activity of N-Modified oleanolic saponins bearing A glucosamine
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A series of N-acyl, N-alkoxycarbonyl, and N-alkylcarbamoyl derivatives of 2′-deoxy-glucosyl bearing oleanolic saponins were synthesized and evaluated against HL-60, PC-3, and HT29 tumor cancer cells. The SAR studies revealed that the activity increased in order of conjugation of 2′ -amino group with carbamate > amide > urea derivatives. Lengthening the alkyl chain increased the cytotoxicity, the peak activity was found to around heptyl to nonyl substitutions. 2′-N-heptoxycarbonyl derivative 56 was found to be the most cytotoxic (IC50 = 0.76 μM) against HL-60 cells. Due to the interesting SARs of alkyl substitutions, we hypothesized that their location in the cell was different, and pursued a location study using 2′-(4″-pentynoylamino) 2′-deoxy-glucosyl OA, which suggested that these compounds distributed mainly in the cytosol.
- Lin, You-Yu,Chan, She-Hung,Juang, Yu-Pu,Hsiao, Hsin-Min,Guh, Jih-Hwa,Liang, Pi-Hui
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p. 1942 - 1958
(2017/11/16)
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- Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins
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Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-β-d-glucosamine, and (1→4)-linked and (1→6)-linked N-acetyl-β-d-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by
- Wang, Peng,Wang, Jun,Guo, TianTian,Li, Yingxia
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experimental part
p. 607 - 620
(2010/09/20)
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- Entada Saponins (ES) II and IV from the Bark of Entada phaseoloides
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The structures of entada saponins II and IV, isolated from the bark of Entada phaseoloides (L.) Merrill (Leguminosae), were elucidated as 3-O-2)-α-L-arabinopyranosyl-(1->6)>4)>-2-acetamido-2-deoxy-β-D-glucopyranosyl-28-O-3)-β-D-xylopyranosyl(1->2)>4)>-6-O-((6R)-6-hydroxy-2,6-dimethyl-(2E)-2,7-octadienoyl)-β-D-glucopyranosyl olenolic acid (1) and entagenic acid (3).Keywords - Entada phaseoloides; Leguminosae; triterpene saponin; 13C-NMR chemical shift; entada saponin II; entada saponin IV
- Okada, Yoshihito,Shibata, Shoji,Javellana, Ana M. J.,Kamo, Osamu
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p. 1264 - 1269
(2007/10/02)
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