81053-26-1

Usage

InChI:InChI=1/C38H61NO8/c1-21(41)39-28-30(43)29(42)24(20-40)46-31(28)47-27-12-13-35(6)25(34(27,4)5)11-14-37(8)26(35)10-9-22-23-19-33(2,3)15-17-38(23,32(44)45)18-16-36(22,37)7/h9,23-31,40,42-43H,10-20H2,1-8H3,(H,39,41)(H,44,45)/t23-,24+,25-,26+,27-,28+,29+,30+,31-,35-,36+,37+,38-/m0/s1

Upstream product

• 908835-49-4 28-O-benzyl 3-O-[3′,4′,6′-tri-O-acetyl-2′-deoxy-2′-phthalimido-β-D-glucopyranosyl] oleanolic ester 
• 146728-55-4 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-(α/β)-D-glucopyranosyl trichloroacetimidate 
• 172847-90-4 p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 303114-51-4 oleanolic acid benzyl ester 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 81053-27-2 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside oleanolic acid 

Relevant academic research and scientific papers

Design, synthesis and cytotoxic activity of N-Modified oleanolic saponins bearing A glucosamine

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.

Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

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

Entada Saponins (ES) II and IV from the Bark of Entada phaseoloides

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