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Triterpenoids, Steroids, and Other Constituents from the Roots of Codonopsis pilosula var. modesta

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Abstract

One new tirucallane-type triterpenoid, codopitirol A (1), has been isolated from the roots of Codonopsis pilosula var. modesta (Nannf.) L. D. Shen, together with fourteen known compounds, including four triterpenoids (2–5), five steroids (6–10), one eudesmane-type sesquiterpenoid (11), one phenylpropanoid (12), one coumarin (13), and two other compounds (14 and 15). The structure of the new compound (1) was determined by HR-ESI-MS and extensive spectroscopic analyses, particularly 1D and 2D NMR, and IR. In addition, compounds 1, 2, and 14 exhibited potential α-glucosidase inhibitory activities with IC50 values of 28.3 ± 2.7, 5.5 ± 0.5, 27.4 ± 1.5 μM, respectively.

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  • Y P Jiang
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