title: Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis.
abstract: Chemical investigation of a sample of propolis originating from North-Western Cameroon led to the isolation of thirteen alk(en)ylphenols (1-13) (inseparable mixture) along with α-amyrin (14), β-amyrin (15), lupeol (16), cycloartenol (17), mangiferonic acid (18), ambonic acid (19), mangiferolic acid (20), ambolic acid (21), isomangiferolic acid (22) and nine alk(en)ylresorcinols (23-31) (inseparable mixture). All compounds were identified following analysis of their spectroscopic data and comparison with previously published reports. Compounds (8), (12), (13) and (30) are new natural products. GC-MS analysis carried out on the alk(en)ylphenol and alk(en)ylresorcinol mixtures (dimethyl disulphide trimethylsilyl derivatives) revealed the presence of saturated and mono-unsaturated compounds with side chain lengths ranging from C11 to C19 and C15 to C19, respectively. The position of the double bond in mono-unsaturated derivatives was established from the characteristic fragments resulting from the cleavage of the bond between the two methylthio-substituted carbons. The most abundant compound in each mixture was 3-(12'Z-heptadecenyl)-phenol (10) and 5-(12'Z-heptadecenyl)-resorcinol (29). This study is the first to report the presence of triterpenes (except for lupeol) and phenolic lipids, including eighteen compounds previously unreported in bee glue, in an African sample.
authors.affiliation: Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow G4 0RE, Scotland, UK.
authors.forename: M N
authors.initials: MN
authors.lastname: Kardar
authors.affiliation: Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow G4 0RE, Scotland, UK.
authors.forename: T
authors.initials: T
authors.lastname: Zhang
authors.affiliation: Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow G4 0RE, Scotland, UK.
authors.forename: G D
authors.initials: GD
authors.lastname: Coxon
authors.affiliation: Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow G4 0RE, Scotland, UK.
authors.forename: D G
authors.initials: DG
authors.lastname: Watson
authors.affiliation: Apiceutical Research Centre, Whitby, North Yorkshire, UK.
authors.forename: J
authors.initials: J
authors.lastname: Fearnley
authors.affiliation: Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow G4 0RE, Scotland, UK. Electronic address: veronique.seidel@strath.ac.uk.
authors.forename: V
authors.initials: V
authors.lastname: Seidel
mesh_terms: D002163:Cameroon; D008401:Gas Chromatography-Mass Spectrometry; D008055:Lipids / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification; D011429:Propolis / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry / Q000302:isolation & purification; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D008055:Lipids; D010636:Phenols; D012118:Resorcinols; D014315:Triterpenes; D011429:Propolis
keywords: Alk(en)ylphenols; Alk(en)ylresorcinols; Cameroonian propolis; Phenolic lipids; Triterpenes