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. 2024 Sep 4;25(17):9602.
doi: 10.3390/ijms25179602.

Isolation and Characterization of Novel Pueroside B Isomers and Other Bioactive Compounds from Pueraria lobata Roots: Structure Elucidation, α-Glucosidase, and α-Amylase Inhibition Studies

Affiliations

Isolation and Characterization of Novel Pueroside B Isomers and Other Bioactive Compounds from Pueraria lobata Roots: Structure Elucidation, α-Glucosidase, and α-Amylase Inhibition Studies

Wei Dai et al. Int J Mol Sci. .

Abstract

Pueraria lobata (Willd.) Ohwi is a traditional medicinal herb that has been extensively used in Chinese medicine for various therapeutic purposes. In this study, twelve chemical constituents were isolated from the roots of P. lobata, comprising three puerosides (compounds 1-3), six alkaloids (compounds 4-9), and three additional compounds (compounds 10-12). Notably, compound 1 (4R-pueroside B) was identified as a novel compound. The structures of all compounds were elucidated using a range of spectroscopic techniques, including CD spectroscopy for the first-time determination of the absolute configurations of pueroside B isomers (compounds 1 and 2). Enzyme inhibition assays revealed that, with the exception of compound 2, all isolated compounds exhibited varying degrees of α-glucosidase and α-amylase inhibitory activity. Remarkably, compound 12 demonstrated IC50 values of 23.25 μM for α-glucosidase inhibition and 27.05 μM for α-amylase inhibition, which are superior to those of the positive control, acarbose (27.05 μM and 36.68 μM, respectively). Additionally, compound 11 exhibited inhibitory activity against α-glucosidase and α-amylase comparable to the positive control, acarbose. Molecular docking studies indicated that compound 12 interacts with the active sites of the enzymes via hydrogen bonds, van der Waals forces, and hydrophobic interactions, which likely contribute to their inhibitory effects. These findings suggest that the chemical constituents of P. lobata could be potential natural sources of α-amylase and α-glucosidase inhibitors, with compound 12 being particularly promising for further investigation.

Keywords: 4R-pueroside B; Pueraria lobata; chemical constituents; molecular docking; α-amylase inhibition; α-glucosidase inhibition.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Structures of compounds 112.
Figure 2
Figure 2
Key HMBC, COSY, and NOESY correlations of compound 1.
Figure 3
Figure 3
CD spectra of compounds 1 (4R-pueroside B) and 2 (4S-pueroside B).
Figure 4
Figure 4
Probable mass spectrometric fragmentation pathway of pueroside B.
Figure 5
Figure 5
The molecular docking results of compound 12 with enzymes. (A) Compound 12 with α-glucosidase. (B) Compound 12 with α-amylase. The left side of each panel shows 3D macro views (upper and lower), the upper right corner presents a 3D local interaction visualization (with the small molecule compound ligand in red and the enzyme protein in blue), and the lower right corner shows a 2D interaction visualization. The PDB ID for α-glucosidase is 3W37, and for α-amylase, it is 2QV4.

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