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A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

  • Mbabi Nyemeck II, Norbert Department of Organic chemistry, Faculty of Science, University of Yaoundé I, Cameroon - Faculty of Chemistry, Philipps-Universität Marburg, Marburg, Germany
  • Ngono Bikobo, Dominique Serge Department of Organic chemistry, Faculty of Science, University of Yaoundé I, Cameroon
  • Zintchem, Auguste Abouem A. Department of Organic chemistry, Faculty of Science, University of Yaoundé I, Cameroon - Department of Chemistry, Higher Training College, University of Yaoundé I, Yaoundé, Cameroon
  • Schäfer, Eva-Maria Institut für pharmazeutische Chemie, Philipps- Universität Marburg, Marburg, Germany
  • Bochet, Christian G. Department Chemie, Universität Fribourg, Switzerland
  • Pegnyemb, Dieudonné Emmanuel Department of Organic chemistry, Faculty of Science, University of Yaoundé I, Cameroon
  • Koert, Ulrich Faculty of Chemistry, Philipps-Universität Marburg, Marburg, Germany
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    17.12.2017
Published in:
  • Natural Product Research. - 2017, vol. 31, no. 24, p. 2875-2884
Campylospermum zenkeri
Ochnaceae
zenkerinol
flavonoids
serotobenine
hemisynthesis
antiplasmodial activity
English Phytochemical investigation of the stem bark of Campylospermum zenkeri led to the isolation of five known compounds: (Z,Z)-9,12-octadecadienoic acid (1), serotobenine (2), agathisflavone (3), lophirone A (4) and lophirone F (5), together with a new derivative of procyanidin B, a catechin dimer named zenkerinol (6). Serotobenine (2) is structurally related to decursivine which shows moderate activity against D6 and W2 strains of Plasmodium falciparum. For a better understanding of structure-activity relationships, three new semi-synthetic derivatives of serotobenine (2) have been prepared. These are: serotobenine monopropionate (2a), serotobenine monopivalate (2b) and serotobenine cyclohexyl ether (2c) respectively. Two of them (2a) and (2b), were evaluated for their antiplasmodial activity against P. falciparum 3D7 strain in a parasite lactate-dehydrogenase (pLDH) assay. Compound 2b was more active than compound 2a based on their IC50 values (36.6 and 123 μM, respectively).
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Analytical chemistry
License
License undefined
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Persistent URL
https://folia.unifr.ch/unifr/documents/306141
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