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Issue 11, 2016
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Concise synthesis of a new triterpenoid saponin from the roots of Gypsophila oldhamiana and its derivatives as α-glucosidase inhibitors

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Abstract

The first synthesis of the triterpenoid saponin 1 and its derivatives 2–3 was efficiently achieved in an efficient and practical strategy with an odourless 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside and a N-phenyltrifluoroacetimidate donor as a key step, and their inhibitory activities against α-glucosidase and α-amylase were evaluated in vitro. The preliminary structure–activity relationship studies demonstrated that C4–CHO and C4–CH2OH were not essential to α-glucosidase inhibitory activity. Among the three compounds, compound 3 exhibited remarkably potent inhibitory activity against α-glucosidase with an IC50 value of 9.17 μM. According to Ki determined at 9.35 μM from the intercept on a Dixon plot, the more potent saponin 3 against α-glucosidase may be a noncompetitive inhibition pattern. In parallel, the lipophilicity of compounds 1–3 was calculated as a prediction for pharmacological potency. According to the predicted log P values, lipophilicity may correlate with the evaluated biological potency.

Graphical abstract: Concise synthesis of a new triterpenoid saponin from the roots of Gypsophila oldhamiana and its derivatives as α-glucosidase inhibitors

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Publication details

The article was received on 24 May 2016, accepted on 24 Sep 2016, published on 26 Sep 2016 and first published online on 26 Sep 2016


Article type: Paper
DOI: 10.1039/C6NJ01602B
Citation: New J. Chem., 2016,40, 9537-9549
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    Concise synthesis of a new triterpenoid saponin from the roots of Gypsophila oldhamiana and its derivatives as α-glucosidase inhibitors

    Q. Liu, T. Guo, F. Li and D. Li, New J. Chem., 2016, 40, 9537
    DOI: 10.1039/C6NJ01602B

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