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Potent α-glucosidase and protein tyrosine phosphatase 1B inhibitors from Artemisia capillaris

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Abstract

As a part of our ongoing effort to identify anti-diabetic constituents from natural sources, we examined the inhibitory activity of the methanol extracts of 12 species of the genus Artemisia, against α-glucosidase and protein tyrosine phosphatase 1B (PTP1B). The methanol extracts of different species exhibited promising α-glucosidase and PTP1B inhibitory activities. Since the methanol extract of Artemisia capillaris exhibited the highest α-glucosidase inhibitory activity together with significant PTP1B inhibitory activity, it was selected for further investigation. Repeated column chromatography based on bioactivity guided fractionation yielded 10 coumarins (esculetin, esculin, scopolin, isoscopolin, daphnetin, umbelliferone, 7-methoxy coumarin, scoparone, scopoletin, 6-methoxy artemicapin C), 8 flavonoids (hyperoside, quercetin, isorhamnetin, cirsilineol, arcapillin, isorhamnetin 3-robinobioside, linarin, isorhamnetin 3-glucoiside), 6 phenolic compounds (1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid methyl ester, 4,5-dicaffeoylquinic acid, 3-caffeoylquinic acid), and one chromone (capillarisin). Among these compounds, esculetin, scopoletin, quercetin, hyperoside, isorhamnetin, 3,5-dicaffeoylquinic acid methyl ester, 3,4-dicaffeoylquinic acid, and 1,5-dicaffeoylquinic acid exhibited potent α-glucosidase inhibitory activity when compared to the positive control acarbose. In addition, esculetin and 6-methoxy artemicapin C displayed PTP1B inhibitory activity. Interestingly, all isolated dicaffeoylquinic acids showed significant PTP1B inhibitory activity. Therefore, the results of the present study clearly demonstrate the potential of the A. capillaris extract to inhibit α-glucosidase and PTP1B. These inhibitory properties can be largely attributed to a combination of different chemical structures, including coumarins, flavonoids, and dicaffeoylquinic acids, which could be further explored to develop therapeutic or preventive agents for the treatment of diabetes.

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Acknowledgments

This research was also supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF), which is funded by the Ministry of Education, Science and Technology (2011-0012539), and by a Grant from the Food & Drug Administration, South Korea (2010).

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Authors and Affiliations

  1. Department of Food Science and Nutrition, Pukyong National University, Busan, 608-737, Republic of Korea

    Md. Nurul Islam & Jae Sue Choi

  2. Department of Food Science and Human Nutrition and Research Institute of Human Ecology, Chonbuk National University, Jeonju, 561-756, Republic of Korea

    Hyun Ah Jung, Hee Sook Sohn & Hye Mi Kim

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  1. Md. Nurul Islam
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Correspondence to Hyun Ah Jung or Jae Sue Choi.

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Nurul Islam, M., Jung, H.A., Sohn, H.S. et al. Potent α-glucosidase and protein tyrosine phosphatase 1B inhibitors from Artemisia capillaris . Arch. Pharm. Res. 36, 542–552 (2013). https://doi.org/10.1007/s12272-013-0069-7

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