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Molecules 2015, 20(2), 2034-2060; doi:10.3390/molecules20022034

The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides

State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China
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Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 26 December 2014 / Revised: 5 January 2015 / Accepted: 21 January 2015 / Published: 27 January 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [934 KB, uploaded 27 January 2015]   |  

Abstract

Twelve galloyl glucosides 112, 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, 112 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 112 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. View Full-Text
Keywords: galloyl glucoside; synthesis; antitumor activity galloyl glucoside; synthesis; antitumor activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Li, C.-W.; Dong, H.-J.; Cui, C.-B. The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides. Molecules 2015, 20, 2034-2060.

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