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Synthesis and Bioactivity
Astragalin
 3-O-glucoside of kaempferol
 Shows anti-oxidant, anti-tumor, anti-human
immunodeficiency virus (HIV), and anti-inflammatory
effects
 Low water solubility of astragalin limits its use.
 Cyclodextrin glucanotransferase (CGTase) enzyme with
maltose (G2) is used to improve AS water solubility and
physiochemical properties
Choung et al., 2017
Do-decyl-α-D-mannopyranoside
 Antimicrobial activity against gram positive bacteria
Staphylococcus aureus
 MIC value (min. inhibitory conc.) is 78 μg/mL
R= O(CH2)11CH3
a= SnCl4, alcohol, CH2Cl2, 16h
b= MeONa, MeOH, 16h
Yield=90%
Bilkova et al., 2015
Triazole-O-glycosides
 They are used as
 Fluorescence probes
 Anti-HIV
 Anti-allergic
 Anti-bacterial
 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl
trichloroacetimidate was used as the glycosyl donor
S. Dutta et al., 2016
Koenigs-knorr Synthesis
 C3-O-neoglycosides of digoxigenin are synthesized by 1-bromo
glycosyl donor and digoxigenin aglycone
 Anti-cancer activity
Li et al., 2017
Phyllanthusmin D
Anti-tumoral activity
Acetylmananthoside B
Liu et al., 2017
Anti-tuberculosis agent
2-((4-((2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyloxy)methyl)-1H-
1,2,3-triazol-1-yl)methyl)-quinoline
Dutta et al., 2016
References
 Choung, W. J., Hwang, S. H., Ko, D. S., Kim, S. B., Kim, S. H.,
Jeon, S. H., ... & Shim, J. H. (2017). Enzymatic synthesis of a novel
kaempferol-3-O-β-d-glucopyranosyl-(1→ 4)-O-α-d-glucopyranoside
using cyclodextrin glucanotransferase and its inhibitory effects on
aldose reductase, inflammation, and oxidative stress. Journal of
agricultural and food chemistry, 65(13), 2760-2767.
 Bilková, A., Paulovičová, E., Paulovičová, L., & Poláková, M.
(2015). Antimicrobial activity of mannose-derived
glycosides. Monatshefte für Chemie-Chemical Monthly, 146(10),
1707-1714.
References
 trifluoromethanesulfonate and metallic copper mediated syntheses of
1, 2, 3-triazole-O-and triazolyl glycoconjugates: consecutive
glycosylation and cyclization under one-pot condition. Tetrahedron
Letters, 57(29), 3086-3090.
 Ren, Y. C., Bao, Y. Z., Liu, J., Zhang, X. K., Zhang, Y. W., Sun, X.
L., ... & Tang, J. S. (2018). Synthesis of C3-Neoglycosides of
digoxigenin and their anticancer activities. European journal of
medicinal chemistry, 145, 252-262.
 Liu, L., Hu, Y., Liu, H., Liu, D. Y., Xia, J. H., & Sun, J. S. (2017).
First Total Synthesis of the Bioactive Arylnaphthyl Lignan
4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside
B. European Journal of Organic Chemistry, 2017(25), 3674-3680.
 Dutta, S., Gupta, S. J., & Sen, A. K. (2016). Silver

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O glycosides

  • 1.
  • 3. Astragalin  3-O-glucoside of kaempferol  Shows anti-oxidant, anti-tumor, anti-human immunodeficiency virus (HIV), and anti-inflammatory effects  Low water solubility of astragalin limits its use.  Cyclodextrin glucanotransferase (CGTase) enzyme with maltose (G2) is used to improve AS water solubility and physiochemical properties Choung et al., 2017
  • 4.
  • 5. Do-decyl-α-D-mannopyranoside  Antimicrobial activity against gram positive bacteria Staphylococcus aureus  MIC value (min. inhibitory conc.) is 78 μg/mL R= O(CH2)11CH3 a= SnCl4, alcohol, CH2Cl2, 16h b= MeONa, MeOH, 16h Yield=90% Bilkova et al., 2015
  • 6. Triazole-O-glycosides  They are used as  Fluorescence probes  Anti-HIV  Anti-allergic  Anti-bacterial  2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl trichloroacetimidate was used as the glycosyl donor
  • 7. S. Dutta et al., 2016
  • 8. Koenigs-knorr Synthesis  C3-O-neoglycosides of digoxigenin are synthesized by 1-bromo glycosyl donor and digoxigenin aglycone  Anti-cancer activity
  • 9. Li et al., 2017
  • 10.
  • 13. References  Choung, W. J., Hwang, S. H., Ko, D. S., Kim, S. B., Kim, S. H., Jeon, S. H., ... & Shim, J. H. (2017). Enzymatic synthesis of a novel kaempferol-3-O-β-d-glucopyranosyl-(1→ 4)-O-α-d-glucopyranoside using cyclodextrin glucanotransferase and its inhibitory effects on aldose reductase, inflammation, and oxidative stress. Journal of agricultural and food chemistry, 65(13), 2760-2767.  Bilková, A., Paulovičová, E., Paulovičová, L., & Poláková, M. (2015). Antimicrobial activity of mannose-derived glycosides. Monatshefte für Chemie-Chemical Monthly, 146(10), 1707-1714.
  • 14. References  trifluoromethanesulfonate and metallic copper mediated syntheses of 1, 2, 3-triazole-O-and triazolyl glycoconjugates: consecutive glycosylation and cyclization under one-pot condition. Tetrahedron Letters, 57(29), 3086-3090.  Ren, Y. C., Bao, Y. Z., Liu, J., Zhang, X. K., Zhang, Y. W., Sun, X. L., ... & Tang, J. S. (2018). Synthesis of C3-Neoglycosides of digoxigenin and their anticancer activities. European journal of medicinal chemistry, 145, 252-262.  Liu, L., Hu, Y., Liu, H., Liu, D. Y., Xia, J. H., & Sun, J. S. (2017). First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside B. European Journal of Organic Chemistry, 2017(25), 3674-3680.  Dutta, S., Gupta, S. J., & Sen, A. K. (2016). Silver