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Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma

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Abstract

The aim of this study was to search for bioactive natural products from medicinal plants targeting vasorelaxant activity and we found the methanol extract from bark of Tabernaemontana dichotoma showed vasorelaxant activity on rat aorta. We isolated eight indole alkaloids including 10-methoxyalstonerine (1), a new macroline type indole alkaloid, from bark of T. dichotoma. These were respectively identified as 10-methoxyaffinisine (2), lochnerine (3), cathafoline (4), (−)-alstonerine (5), 19,20-dehydro-10-methoxytalcarpine (6), alstonisine (7), and alstonal (8) based on spectroscopic analysis. Among them, sarpagine type (2 and 3), akuammiline type (4), and macroline oxindole type (7 and 8) showed potent vasorelaxant activity. Mechanism of action on vasorelaxant activity of 10-methoxyaffinisine (2), cathafoline (4), and alstonisine (7) was clarified. Effects of 10-methoxyaffinisine (2), cathafoline (4), and alstonisine (7) were partially mediated the NO release from endothelial cells. Furthermore, 10-methoxyaffinisine (2) and alstonisine (7) attribute to the inhibitory effect of VDC and ROC, and cathafoline (4) have inhibitory effect on Ca2+ influx via ROC. In addition, 10-methoxyaffinisine (2) as a major compound from bark of T. dichotoma showed hypotensive effect on normotensive rats in vivo.

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Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and a grant from The Open Research Center Project in Hoshi University.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo, 142-8501, Japan

    Kazumasa Zaima, Ikumi Koga, Nobuhide Iwasawa, Takahiro Hosoya, Yusuke Hirasawa, Toshio Kaneda & Hiroshi Morita

  2. Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, Serdang, Malaysia

    Intan Safinar Ismail & Nordin Hj Lajis

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  1. Kazumasa Zaima
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  2. Ikumi Koga
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  9. Hiroshi Morita
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Correspondence to Hiroshi Morita.

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Zaima, K., Koga, I., Iwasawa, N. et al. Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma . J Nat Med 67, 9–16 (2013). https://doi.org/10.1007/s11418-012-0638-y

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  • DOI: https://doi.org/10.1007/s11418-012-0638-y

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