The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides
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-d...
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doaj-5512032b172543019d87fda17333d7f02020-11-24T22:16:44ZengMDPI AGMolecules1420-30492015-01-012022034206010.3390/molecules20022034molecules20022034The Synthesis and Antitumor Activity of Twelve Galloyl GlucosidesChang-Wei Li0Hua-Jin Dong1Cheng-Bin Cui2State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, ChinaState Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, ChinaState Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, ChinaTwelve 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.http://www.mdpi.com/1420-3049/20/2/2034galloyl glucosidesynthesisantitumor activity |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Chang-Wei Li Hua-Jin Dong Cheng-Bin Cui |
spellingShingle |
Chang-Wei Li Hua-Jin Dong Cheng-Bin Cui The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides Molecules galloyl glucoside synthesis antitumor activity |
author_facet |
Chang-Wei Li Hua-Jin Dong Cheng-Bin Cui |
author_sort |
Chang-Wei Li |
title |
The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides |
title_short |
The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides |
title_full |
The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides |
title_fullStr |
The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides |
title_full_unstemmed |
The Synthesis and Antitumor Activity of Twelve Galloyl Glucosides |
title_sort |
synthesis and antitumor activity of twelve galloyl glucosides |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2015-01-01 |
description |
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. |
topic |
galloyl glucoside synthesis antitumor activity |
url |
http://www.mdpi.com/1420-3049/20/2/2034 |
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