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Anti-inflammatory terpenylated coumarins from the leaves of Zanthoxylum schinifolium with α-glucosidase inhibitory activity

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Abstract

Nine terpenylated coumarins, namely 7-[(E)-3′,7′-dimethyl-6′-oxo-2′,7′-octadienyl]oxy-coumarin (1), schinilenol (2), schinindiol (3), collinin (4), 7-[(E)-7′-hydroxy-3′,7′-dimethy-locta-2′,5′-dienyloxy]-coumarin (5), 8-methoxyanisocoumarin (6), 7-(6′R-hydroxy-3′,7′-dimethyl-2′E,7′-octadienyloxy)coumarin (7), (E)-4-methyl-6-(coumarin-7′-yloxy)hex-4-enal (8), and aurapten (9), along with a 4-quinolone alkaloid (10) and integrifoliodiol (11), were isolated from the leaves of Zanthoxylum schinifolium. Of the isolates, compounds 4 and 7 potentially inhibited NO production in lipopolysaccharide (LPS)-stimulated macrophage RAW264.7 cells, with IC50 values of 5.9 ± 0.8 and 18.2 ± 1.8 μM, respectively. Furthermore, compounds 4 and 7 dose-dependently reduced the LPS-induced iNOS expression. Moreover, pre-incubation of cells with 4 and 7 significantly suppressed LPS-induced COX-2 protein expression. In addition, compounds 4, 7, 8, and 10 showed strong α-glucosidase inhibitory effects, with IC50 values of 92.1 ± 0.7, 90.6 ± 0.9, 78.2 ± 0.2, and 82.4 ± 0.8 μM, respectively. Compounds 1, 5, and 11 displayed moderate effects with IC50 values of 161.6 ± 0.3, 164.4 ± 1.1, and 155.4 ± 0.9 μM, while acarbose, a positive control, possessed an IC50 value of 121.5 ± 1.0 μM. This is the first investigation on the α-glucosidase inhibitory effect of components from Zanthoxylum schinifolium. Further studies should be made on active compounds.

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Acknowledgments

This research was supported by the research grants funded by the Catholic University of Daegu in 2013. The authors are grateful to S.H. Kim and collaborators at the Korea Basic Science Institute (Daegu) for measuring the mass spectra.

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Authors and Affiliations

  1. College of Pharmacy, Catholic University of Daegu, Hayang, Gyeongbuk, 38430, Republic of Korea

    Phi-Hung Nguyen, Bing Tian Zhao, Byung Sun Min & Mi Hee Woo

  2. College of Natural Science, Kangwon National University, Kangwon, 24341, Republic of Korea

    Okhwa Kim & Jeong Hyung Lee

  3. Faculty of Food Science and Biotechnology, Pukyong National University, Busan, 48513, Republic of Korea

    Jae Sue Choi

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  1. Phi-Hung Nguyen
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Correspondence to Mi Hee Woo.

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Nguyen, PH., Zhao, B.T., Kim, O. et al. Anti-inflammatory terpenylated coumarins from the leaves of Zanthoxylum schinifolium with α-glucosidase inhibitory activity. J Nat Med 70, 276–281 (2016). https://doi.org/10.1007/s11418-015-0957-x

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  • DOI: https://doi.org/10.1007/s11418-015-0957-x

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