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.
Highlights
Compounds 1–12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at
In the course of our studies on bioactive natural products [30,31,32,33,34,35,36,37,38,39,40,41,42,43,44], we have reported the isolation of some phenolic compounds with antitumor, anti-hypoxia, and anti-bacterial activities, including several galloyl glucosides with one to four galloyl groups, from a medicinal plant, Choerospondias axillaries, which is used as a traditional herbal medicine in China [41,42,43,44]
In [4] an isolated galloyl glucoside was recorded as methyl 3,6-di-Ogalloyl-α-D-glucopyranoside (9) in the Abstract and Section 2.1, but the structure of the compound given in the text, coupled with the cited literature [49] for identification without data, indicated that the name of this compound in the literature [4] was a miswriting of the correct name methyl 3,6-di-Ogalloyl-β-D-glucopyranoside [49], and no more reports so far have mentioned 9
Summary
A kind of plant polyphenolics, display various important, diverse biological and pharmacological activities, such as virustatic [1], anti-oxidant and free radical scavenging [2,3,4], interaction with protein [5] and enzyme inhibitory [6,7], anti-inflammatory [8], neuronal cell protecting [9], transient global ischemia/reperfusion-induced brain injury protecting [10], keratinocyte proliferation and mitochondrial activity stimulating [11], anti-diabetic [12], cisplatin-induced nephrotoxicity protecting [13] and antitumor [14,15,16,17,18] activities, and so on. The synthesis of some galloyl glucosides has been reported [25,26,27,28,29], in view of their diverse and important biological activities, it is still worthwhile to synthesize other galloyl glucosides with less galloyl groups than. In the course of our studies on bioactive natural products [30,31,32,33,34,35,36,37,38,39,40,41,42,43,44], we have reported the isolation of some phenolic compounds with antitumor, anti-hypoxia, and anti-bacterial activities, including several galloyl glucosides with one to four galloyl groups, from a medicinal plant, Choerospondias axillaries, which is used as a traditional herbal medicine in China [41,42,43,44]. The synthesis and antitumor activity of 1–12 were reported in detail in this paper
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