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LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata

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Abstract

Phytochemical investigation of leaves and stem bark extracts of Clausena anisata monitored by liquid chromatography high-resolution mass spectrometry (LC-HR-MS) analysis led to the isolation and characterization of twenty-one secondary metabolites: four carbazole alkaloids (1–4) including one new name clausamine H (1), fourteen coumarins (5–18), two porphyrin derivatives (19–20), and one limonoid (21). Crude extracts were analyzed first by LC-HR-MS, and target compounds were isolated by a multi-step separation procedure using column chromatography and preparative high-performance liquid chromatography (prep-HPLC) monitored by LC-HR-MS analysis. The structures of isolates were determined by means of spectroscopic and spectrometric data, as well as by comparison with literature values. The isolates showed weak to high antibacterial activities with imperatorin (14) being the most active one. Cytotoxic activities against HeLa and monkey Vero cells were also investigated, and murrayamine-A (4), 3-(1,1-dimethyl allyl) xanthyletin (5) gravelliferone (7), excavatin D (10), 7-[(E)-7-hydroxy-3,7-dimethylocta-2,5-dienyloxyl]-coumarin (13), phellopterin (15), and 1-O-methylclausenolide (21) were found active with LC50 values ranged from 1.14 to 3.26 µg/mL and a good selectivity index values (SI 38.20–231.58) against the HeLa cells. However, these compounds were non-toxic to normal cells indicating their high potential to be used as anticancer drug.

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Acknowledgments

This work was supported by the German Academic Exchange Service (DAAD), grant A/13/00965 to SJNT for two months research stay in Germany. The authors gratefully acknowledge the strong support of the DAAD through its initiative “Welcome to Africa” and the Ministry of Innovation, Science, Research and Technology of the State of North Rhine, Westphalia, Germany and the German Research Foundation (DFG) for funding a high-resolution mass spectrometer. We thank Cornelia Stolle, Jana Gaskow, and Gabriele Hardes for excellent technical assistance. JDT acknowledges funding from the Indian Ministry of Education and Research through their CV Raman fellowship grant. We also thank CAS (UGC) for providing partial contingency support at the Department of Biochemistry, University of Calcutta.

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Authors and Affiliations

  1. Department of Chemistry, Higher Teachers’ Training College, University of Maroua, P.O. Box 55, Maroua, Cameroon

    Simplice Joel Ndendoung Tatsimo & Alain Meli Lannang

  2. Department of Biochemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon

    Jean-De-Dieu Tamokou

  3. Institute of Environmental Research (INFU) of the Faculty of Chemistry and Chemical Biology, TU Dortmund, Otto-Hahn-Str.6, 44221, Dortmund, Germany

    Marc Lamshöft, Ferdinand Talontsi Mouafo & Michael Spiteller

  4. Department of Biochemistry, University of Calcutta, 35 Ballygunge Circular Road, Kolkota, 700 019, India

    Prodipta Sarkar & Prasanta Kumar Bag

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  1. Simplice Joel Ndendoung Tatsimo
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  2. Jean-De-Dieu Tamokou
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Correspondence to Simplice Joel Ndendoung Tatsimo.

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Tatsimo, S.J.N., Tamokou, JDD., Lamshöft, M. et al. LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata . Med Chem Res 24, 1468–1479 (2015). https://doi.org/10.1007/s00044-014-1233-4

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  • DOI: https://doi.org/10.1007/s00044-014-1233-4

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