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Aporphine Alkaloids from Triclisia dictyophylla Diels by pH-Zone Refining Countercurrent Chromatography

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Abstract

A new dimeric aporphine alkaloid, biscocsarmine, 2, together with lirioferine, 1, and cocsarmine, 3, were isolated from the ethanol extract of the stems of Triclisia dictyophylla Diels (Menispermaceae) using a preparative pH-zone refining CCC in a single step. The first solvent system family tested for this fractionation was hexane–ethyl acetate–methanol–water (HEMWat) at a series of solvent ratios, and hydrochloric acid and triethylamine at 5 mM as eluter/retainer. None of these HEMWat ratios, however, gave suitable K for the target alkaloids. Ethyl acetate–n-butanol–water (EBuWat) was tested instead and the selected solvent system was composed of ethyl acetate–n-butanol–water 5:5:10 (v/v), where triethylamine (60 mM) was added to the upper organic stationary phase as a retainer and hydrochloric acid (5 mM) to the aqueous mobile phase as an eluter. The chemical structures of the isolated compounds were elucidated based on comprehensive spectroscopic and spectrometric techniques. This is the first report of aporphine alkaloids in this plant species.

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Abbreviations

EBuWat:

Ethyl acetate–n-butanol–water

HEMWa:

Hexane–ethyl acetate–methanol–water

TEA:

Trimethylamine

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Acknowledgements

We are grateful to CNPq/TWAS post-doctoral fellowship (ELDK) and FAPERJ for financial support. GGL is indebted for the opportunity of presenting this work at CCC2016 Conference in Chicago, USA.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon

    Eutrophe Le Doux Kamto, Eric Robert Tiam & Dieudonné Emmanuel Pegnyemb

  2. Instituto de Pesquisas de Produtos Naturais, Centro de Ciencias da Saúde, Bl. H, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro, RJ, 21.941-902, Brazil

    Eutrophe Le Doux Kamto, Simony C. Mendonça & Gilda Guimarães Leitão

  3. Department of Chemistry, Higher Teacher Training College, University of Yaounde 1, Yaounde, Cameroon

    Auguste Abouem A Zintchem

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  1. Eutrophe Le Doux Kamto
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  2. Simony C. Mendonça
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  3. Auguste Abouem A Zintchem
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Correspondence to Eutrophe Le Doux Kamto or Gilda Guimarães Leitão.

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Kamto, E.L.D., Mendonça, S.C., Abouem A Zintchem, A. et al. Aporphine Alkaloids from Triclisia dictyophylla Diels by pH-Zone Refining Countercurrent Chromatography. Chromatographia 84, 13–20 (2021). https://doi.org/10.1007/s10337-020-03977-x

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