ArticleMolecules (Basel, Switzerland)2015
The synthesis and antitumor activity of twelve galloyl glucosides.
Article in Molecules (Basel, Switzerland), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 36 citations in OpenAlex.
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- Probing into the chemopreventive properties of synthetic 1,3,6-tri-O-galloyl-α-D-glucose (α-TGG) against glioblastoma and triple-negative breast cancer-derived cell models.Current research in pharmacology and drug discovery · 2025Article
- New Hydrolyzable Tannin with Potent Antioxidant andFoods (Basel, Switzerland) · 2023Article
- From Hamamelitannin Synthesis to the Study of Enzymatic Acylations of D-Hamamelose.Biomolecules · 2023Article
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- Structural Characterization and Assessment of Anti-Inflammatory Activities of Polyphenols and Depsidone Derivatives fromMolecules (Basel, Switzerland) · 2022Article
- Digalloyl Glycoside: A Potential Inhibitor of Trypanosomal PFK fromPlants (Basel, Switzerland) · 2022Article
- Both d- and l-Glucose Polyphosphates Mimic d-Journal of medicinal chemistry · 2020Article
- Functional Characterization of the ycjQRS Gene Cluster from Escherichia coli: A Novel Pathway for the Transformation of d-Gulosides to d-Glucosides.Biochemistry · 2019Article
- A tannin compound fromChinese medicine · 2019Article
- Separation, Identification, and Bioactivities of the Main Gallotannins of Red Sword Bean (Frontiers in chemistry · 2018Article
- Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-α-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-α-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-β-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-β-D-glucopyranose (1), 1,4,6-tri-O-galloyl-β-D-glucopyranose (2), 1,2-di-O-galloyl-β-D-glucopyranose (3), 1,3-di-O-galloyl-β-D-glucopyranose (4), 1,2,3-tri-O-galloyl-α-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-α-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 μg/mL, and their IC50 values were determined to be varied in 17.2-124.7 μM on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 μg/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control.
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