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Zeitschrift für Naturforschung C

A Journal of Biosciences

Editor-in-Chief: Seibel, Jürgen

Editorial Board: Aigner , Achim / Boland, Wilhelm / Bornscheuer, Uwe / Hoffmann, Klaus

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1865-7125
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Volume 73, Issue 9-10

Issues

Pobeguinine: a monoterpene indole alkaloid and other bioactive constituents from the stem bark of Nauclea pobeguinii

Jean J.K. Bankeu
  • Corresponding author
  • Department of Chemistry, Faculty of Science, The University of Bamenda, P.O. Box 39, Bambili, Cameroon, Phone: (+237) 677 95 56 30
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/ Stéphanie Madjouka
  • Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon
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/ Guy R.T. Feuya
  • Department of Chemistry, Faculty of Science, Scientific and Technical University of Masuku, Box 943, Franceville, Gabon
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/ Yannick S.F. Fongang
  • Department of Chemistry, Higher Teacher Training College, University of Maroua, P.O. Box 55, Maroua, Cameroon
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/ Sadaf Siddiqui
  • H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
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/ Iftikhar Ali
  • Department of Chemistry, Karakoram International University, 15100-Gilgit, Gilgit-Baltistan, Pakistan
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/ Lateef Mehreen
  • Pharmaceutical Research Centre of Pakistan, Council of Scientific and Industrial Research Laboratories Complex, Karachi 75280, Pakistan
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/ Bruno N. Lenta
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  • Department of Chemistry, Higher Teacher Training College, University of Yaoundé I, P.O. Box 47, Yaoundé, Cameroon, Phone: (+237) 675 097 561
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/ Sammer Yousuf
  • H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
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/ Didérot T. Noungoué
  • Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon
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/ Augustin S. Ngouela
  • Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon
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/ Muhammad S. Ali
  • H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
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Published Online: 2018-01-10 | DOI: https://doi.org/10.1515/znc-2017-0127

Abstract

Phytochemical investigation of dichloromethane neutral phase of stem bark of Nauclea pobeguinii led to the isolation of a new monoterpene indole alkaloid, pobeguinine 1 along with 14 known compounds including (−)-naucleofficine D (2a), (+)-naucleofficine D (2b), naucleidinal (3), quafrinoic acid (4), betulinic acid (5), ursolic acid (6), quinovic acid (7), quinovic acid 3-O-α-L-rhamnopyranoside (8a), quinovic acid 3-O-β-D-fucopyranoside (8b), β-sitosterol (9), β-sitosterol 3-O-β-D-glucopyranoside (10), benzoic acid (11), lacceroic acid (12) and n-heptacosane (13). The structure of compound 1 was unambiguously assigned on the basis of single-crystal X-ray diffraction technique. The Hirshfeld surface analysis was further carried out to quantitatively analyze the role of various types of hydrogen bonding in crystal stability. These structures were elucidated using spectroscopic methods. The isolates were evaluated for their radical scavenging properties as well as inhibitory activities against urease and tyrosinase enzymes with IC50 values ranging from 13.4 to 58.9, 46.0 to 86.7 and 39.4 to 87.1 μg/mL, respectively. Compound 6 exhibited maximum radical scavenging activity with IC50 13.4 μg/mL, while compound 4 exhibited maximum tyrosinase with IC50 39.4 μg/mL. All the isolates showed moderate urease inhibition.

This article offers supplementary material which is provided at the end of the article.

Keywords: monoterpene indole alkaloid; Nauclea pobeguinii; radical scavenging activities; single-crystal X-ray; tyrosinase inhibition; urease inhibition

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About the article

Received: 2017-07-12

Revised: 2017-11-02

Accepted: 2017-11-30

Published Online: 2018-01-10

Published in Print: 2018-09-25


Disclosure statement: The authors declare that there is no conflict of interest regarding the publication of this manuscript.


Citation Information: Zeitschrift für Naturforschung C, Volume 73, Issue 9-10, Pages 335–344, ISSN (Online) 1865-7125, ISSN (Print) 0939-5075, DOI: https://doi.org/10.1515/znc-2017-0127.

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