title: A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine.
abstract: 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 IC50values (36.6 and 123 μM, respectively).
authors.affiliation: a Department of Organic Chemistry, Faculty of Science , University of Yaoundé I , Yaoundé , Cameroon.|c Faculty of Chemistry , Philipps-Universität Marburg , Marburg , Germany.
authors.forename: Norbert
authors.initials: N
authors.lastname: Mbabi Nyemeck
authors.affiliation: a Department of Organic Chemistry, Faculty of Science , University of Yaoundé I , Yaoundé , Cameroon.
authors.forename: Dominique
authors.initials: D
authors.lastname: Serge Ngono Bikobo
authors.affiliation: a Department of Organic Chemistry, Faculty of Science , University of Yaoundé I , Yaoundé , Cameroon.|b Department of Chemistry , Higher Training College, University of Yaoundé I , Yaoundé , Cameroon.
authors.forename: Auguste
authors.initials: A
authors.lastname: Abouem A Zintchem
authors.affiliation: d Institut für pharmazeutische Chemie , Philipps-Universität Marburg , Marburg , Germany.
authors.forename: Eva-Maria
authors.initials: EM
authors.lastname: Schäfer
authors.affiliation: e Department Chemie , Universität Fribourg , Fribourg , Switzerland.
authors.forename: Christian
authors.initials: C
authors.lastname: Bochet
authors.affiliation: a Department of Organic Chemistry, Faculty of Science , University of Yaoundé I , Yaoundé , Cameroon.
authors.forename: Dieudonné
authors.initials: D
authors.lastname: Emmanuel Pegnyemb
authors.affiliation: c Faculty of Chemistry , Philipps-Universität Marburg , Marburg , Germany.
authors.forename: Ulrich
authors.initials: U
authors.lastname: Koert
mesh_terms: D000962:Antimalarials / Q000737:chemistry* / Q000494:pharmacology; D044946:Biflavonoids / Q000737:chemistry* / Q000302:isolation & purification; D002392:Catechin / Q000737:chemistry*; D026121:Indole Alkaloids / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification / Q000493:pharmacokinetics; D020128:Inhibitory Concentration 50; D043842:Ochnaceae / Q000737:chemistry*; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects; D044945:Proanthocyanidins / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000962:Antimalarials; D044946:Biflavonoids; D026121:Indole Alkaloids; D007211:Indoles; D010936:Plant Extracts; D044945:Proanthocyanidins; C560343:decursivine; C531376:serotobenine; C479578:procyanidin B; C079168:agathisflavone; D002392:Catechin
keywords: Campylospermum zenkeri; Ochnaceae; antiplasmodial activity; flavonoids; hemisynthesis; serotobenine; zenkerinol