Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis

M. N. Kardar, T. Zhang, G. D. Coxon, D. G. Watson, J. Fearnley, V. Seidel

Research output: Contribution to journalArticle

11 Citations (Scopus)
128 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)156-163
Number of pages8
JournalPhytochemistry
Volume106
Early online date4 Aug 2014
DOIs
Publication statusPublished - 1 Oct 2014

Fingerprint

Propolis
Triterpenes
propolis
triterpenoids
Lipids
Acids
acids
lipids
lupeol
Unsaturated compounds
Derivatives
resorcinol
Cameroon
Phenol
Biological Products
Chain length
phenol
Carbon
sampling
carbon

Keywords

  • alk(en)ylphenols
  • alk(en)ylresorcinols
  • Cameroonian propolis
  • phenolic lipids
  • triterpenes

Cite this

@article{8c5a5d5268c543aabcde3ee21aafc089,
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.",
keywords = "alk(en)ylphenols, alk(en)ylresorcinols, Cameroonian propolis, phenolic lipids, triterpenes",
author = "Kardar, {M. N.} and T. Zhang and Coxon, {G. D.} and Watson, {D. G.} and J. Fearnley and V. Seidel",
year = "2014",
month = "10",
day = "1",
doi = "10.1016/j.phytochem.2014.07.016",
language = "English",
volume = "106",
pages = "156--163",
journal = "Phytochemistry",
issn = "0031-9422",

}

Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis. / Kardar, M. N.; Zhang, T.; Coxon, G. D.; Watson, D. G.; Fearnley, J.; Seidel, V.

In: Phytochemistry, Vol. 106, 01.10.2014, p. 156-163.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Characterisation of triterpenes and new phenolic lipids in Cameroonian propolis

AU - Kardar, M. N.

AU - Zhang, T.

AU - Coxon, G. D.

AU - Watson, D. G.

AU - Fearnley, J.

AU - Seidel, V.

PY - 2014/10/1

Y1 - 2014/10/1

N2 - 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.

AB - 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.

KW - alk(en)ylphenols

KW - alk(en)ylresorcinols

KW - Cameroonian propolis

KW - phenolic lipids

KW - triterpenes

UR - http://www.scopus.com/inward/record.url?scp=84906944126&partnerID=8YFLogxK

UR - http://www.sciencedirect.com/science/article/pii/S0031942214002866

U2 - 10.1016/j.phytochem.2014.07.016

DO - 10.1016/j.phytochem.2014.07.016

M3 - Article

VL - 106

SP - 156

EP - 163

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

ER -