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Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack

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Abstract

Two new sarpagine-type indole alkaloids (1 and 2), together with five known alkaloids; 12-methoxy-4-methylvoachalotine (3), 16-demethoxycarbonylvoacamine (4), isositsirikine (5), affinisine (6), affinine (7), were isolated from the bark of Tabernaemontana macrocarpa Jack. The structures of these alkaloids were determined based on spectroscopic data, chemical correlation, and comparison with the literature. 16-Demethoxycarbonylvoacamine (4) showed antiplasmodial activities against Plasmodium falciparum 3D7 and cytotoxic activities against human cell line, HepG2 cells.

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Acknowledgments

We thank Masatsugu Kimura (Osaka City University, Osaka, Japan) for the kind gift of the 3D7 strain and Dr. Toru Okamoto and Prof. Yoshiharu Matsuura (Osaka University, Osaka, Japan) for kindly providing HepG2 cells. We also thank Mr. Yuji Toya and Dr. Kinya Uchihashi (Sysmex, Kobe, Japan) for the setting of the XN-30 analyzer and Ms. Toshie Ishisaka and Ms. Sawako Itagaki for their technical assistance. We also thank the Centre for Plant Conservation Botanic Gardens, Bogor, Indonesia, for providing and determining the plant materials. This research was partially supported by the Ministry of Education, Culture, Sport, Science and Technology, Grant-in-Aid for Young Scientist (B) to AEN and YH (grant numbers 17K15472 and 15K18890, respectively), Grants-in-Aid for Scientific Research (C) to TT (grant number 16K08759) and by Sysmex Corporation to TH.

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Authors and Affiliations

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

    Puteri Amelia, Alfarius Eko Nugroho, Yusuke Hirasawa, Toshio Kaneda & Hiroshi Morita

  2. Department of Pharmacy, Faculty of Medical Sciences, Universitas Islam Negeri (UIN) Syarif Hidayatullah, Jakarta, 15412, Indonesia

    Puteri Amelia

  3. Department of Molecular Protozoology, Research Institute for Microbial Diseases, Osaka University, 3-1 Yamadaoka, Suita, Osaka, 565-0871, Japan

    Takahiro Tougan & Toshihiro Horii

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  1. Puteri Amelia
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  2. Alfarius Eko Nugroho
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  3. Yusuke Hirasawa
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  4. Toshio Kaneda
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  5. Takahiro Tougan
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Correspondence to Hiroshi Morita.

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Amelia, P., Nugroho, A.E., Hirasawa, Y. et al. Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. J Nat Med 73, 820–825 (2019). https://doi.org/10.1007/s11418-019-01317-4

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