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Cytotoxic alkaloids against human colon adenocarcinoma cell line (HT-29) from the seed embryos of Nelumbo nucifera

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Abstract

Phytochemical investigation of the CHCl3 extract of the seed embryos of Nelumbo nucifera Gaertn resulted in the isolation of a new naturally occurring bisbenzylisoquinoline alkaloid, O-methylneferine (1), together with five known alkaloids, neferine (2), armepavine (3), (–)-(1R)-N-methylcoclaurine (4), nuciferine (5), and pronuciferine (6). The structures of these compounds were characterized by spectroscopic methods and comparison of physical properties with those reported in the literature. Among them, compounds 1 and 2 exhibited significant activity against human colon adenocarcinoma cell line (HT-29), with IC50 values of 0.70 and 1.61 µM, respectively, which were 8- and 3.5-fold higher than that of the reference anticancer drug, doxorubicin (IC50 5.63 µM). Moreover, compounds 1 and 2 displayed less cytotoxic activity against the non-cancerous HEK 239 cells with the IC50 values of 42.48 and 12.19 μM, respectively, whereas the cytotoxicity of doxorubicin against this cell line was 0.22 μM. The very potent cytotoxicity against HT-29 cell line and very high selectivity index (60.6-fold) of the alkaloid 1 is of particular significant; it could be considered as a promising structure lead for anti-colon cancer drug development.

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Acknowledgements

This work was supported by The Thailand Research Fund (grant no. DBG5980003) and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission.

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Authors and Affiliations

  1. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, 10240, Thailand

    Waraluck Chaichompoo, Boon-ek Yingyongnarongkul & Apichart Suksamrarn

  2. Department of Chemistry, School of Science, University of Phayao, Maeka, Muang, Phayao, 56000, Thailand

    Ratchanaporn Chokchaisiri

  3. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok, 10110, Thailand

    Nuttapon Apiratikul

  4. Department of Physiology, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand

    Arthit Chairoungdua

  5. School of Allied Health Sciences, Walailak University, Nakhon Si Thammarat, 80161, Thailand

    Warangkana Chunglok

  6. Department of Anatomy, Faculty of Medicine, Chiang Mai University, Chiang Mai, 50200, Thailand

    Chainarong Tocharus

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  1. Waraluck Chaichompoo
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  2. Ratchanaporn Chokchaisiri
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  8. Apichart Suksamrarn
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Correspondence to Apichart Suksamrarn.

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Chaichompoo, W., Chokchaisiri, R., Apiratikul, N. et al. Cytotoxic alkaloids against human colon adenocarcinoma cell line (HT-29) from the seed embryos of Nelumbo nucifera . Med Chem Res 27, 939–943 (2018). https://doi.org/10.1007/s00044-017-2115-3

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  • DOI: https://doi.org/10.1007/s00044-017-2115-3

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