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Bio-Assay Guided Isolation of Flavonoids from Scutellaria barbata D. Don and Their Mechanism of α-Glucosidase Inhibition

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Pharmaceutical Chemistry Journal Aims and scope

Inhibition of α-glucosidase is a therapeutic approach that slows down the hydrolysis of oligosaccharides and disaccharides to glucose. Therefore, delaying the digestion and absorption of carbohydrates by inhibiting α-glucosidase can reduce blood glucose levels. Herein, the methanol extract of Scutellaria barbata D. Don was screened for α-glucosidase inhibitors using an in vitro inhibition assay and chromatographic techniques (column chromatography, TLC, and HPLC). Six known flavonoids were isolated, including chrysin (1), wogonin (2), apigenin (3), hispidulin (4), pinocembrin (5) and 6-methoxyaringenin (6), and their structures were identified by spectroscopic methods (NMR and MS) and by comparing their spectral data to reported values. Compounds 1 – 6 exhibited higher inhibitory activities against α-glucosidase with IC50 values between 17 μM and 192 μM compared to the reference drug acarbose (1463.0 ± 29.5 μM). The kinetic analysis showed that flavonoid 1 was a competitive inhibitor, flavonoids 2 and 4 were mixed-type inhibitors, while flavonoids 3, 5 and 6 were noncompetitive inhibitors of α-glucosidase. Computer modeling showed that the primary amino acid residue interacted with the flavonoids primarily through hydrogen bonding, with binding energies ranging from –5.44 to –1.85 kcal/mol. These results indicate that compounds 1 – 6 are potential α-glucosidase inhibitors.

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Acknowledgements

We thank Ms Shu-Chi Lin and Ms Lih-Mei Sheu for their technical assistance with the MS measurements in the Instrumentation Centre at National Tsing Hua University and National Chung Hsing University. The nuclear magnetic resonance spectrometer (NMR) was conducted in the Precision Instruments Centre of National Pingtung University of Science and Technology.

FUNDING

This work was supported by the Ministry of Science and Technology of Taiwan (Grant MOST 105-2320-B-020- 002-MY3 and MOST 108-2320-B-020-003) and NPUST-KMU Joint Research Project (KP109005 and NPUST-KM-109-P006).

SUPPLEMENTARYMATERIAL

The 1H and 13C NMR spectra of compounds 1 – 6 are available as supplementary material by request from the authors.

CONFLICT OF INTEREST

The authors declare that they have no conflicts of interest.

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Authors and Affiliations

  1. Department of Tropical Agriculture and International Cooperation, National Pingtung University of Science and Technology, Pingtung, 91201, Taiwan

    Bongani Sicelo Dlamini

  2. Department of Life Science, National Taitung University, Taitung, 95002, Taiwan

    Chiy-Rong Chen

  3. Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung, 40402, Taiwan

    Yueh-Hsiung Kuo

  4. Department of Biotechnology, Asia University, Taichung, 41354, Taiwan

    Yueh-Hsiung Kuo

  5. Chinese Medicine Research Center, China Medical University, Taichung, 40402, Taiwan

    Yueh-Hsiung Kuo

  6. Department of Food Science, National Pingtung University of Science and Technology, Pingtung, 91201, Taiwan

    Yu-Kuo Chen

  7. Department of Biological Science and Technology, National Pingtung University of Science and Technology, Pingtung, 91201, Taiwan

    Jue-Liang Hsu & Chi-I Chang

  8. Research Centre for Austronesian Medicine and Agriculture, National Pingtung University of Science and Technology, Pingtung, 91201, Taiwan

    Jue-Liang Hsu

  9. Research Centre for Tropic Agriculture, National Pingtung University of Science and Technology, Pingtung, 91201, Taiwan

    Jue-Liang Hsu

  10. Research Centre for Active Natural Products Development, National Pingtung University of Science and Technology, Pingtung, 91201, Taiwan

    Chi-I Chang

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  1. Bongani Sicelo Dlamini
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  2. Chiy-Rong Chen
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Dlamini, B.S., Chen, CR., Kuo, YH. et al. Bio-Assay Guided Isolation of Flavonoids from Scutellaria barbata D. Don and Their Mechanism of α-Glucosidase Inhibition. Pharm Chem J 56, 683–691 (2022). https://doi.org/10.1007/s11094-022-02695-y

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  • DOI: https://doi.org/10.1007/s11094-022-02695-y

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