Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei

Ruwida M K Omar, John Igoli, Alexander I Gray, Godwin Unekwuojo Ebiloma, Carol Clements, James Fearnley, Ru Angeli Edrada Ebel, Tong Zhang, Harry P De Koning, David G Watson

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

INTRODUCTION: A previous study showed the unique character of Nigerian red propolis from Rivers State, Nigeria (RSN), with regards to chemical composition and activity against Trypanosoma brucei in comparison with other African propolis.

OBJECTIVE: To carry out fractionation and biological testing of Nigerian propolis in order to isolate compounds with anti-trypanosomal activity. To compare the composition of the RSN propolis with the composition of Brazilian red propolis.

METHODOLOGY: Profiling was carried out using HPLC-UV-ELSD and HPLC-Orbitrap-FTMS on extracts of two samples collected from RSN with data extraction using MZmine software. Isolation was carried out by normal phase and reversed phase MPLC. Elucidation of the compounds with a purity > 95% was performed by 1D/2D NMR HRMS and HRLC-MS(n) .

RESULTS: Ten phenolic compounds were isolated or in the case of liquiritigenin partially purified. Data for nine of these correlated with literature reports of known compounds i.e. one isoflavanone, calycosin (1); two flavanones, liquiritigenin (2) and pinocembrin (5); an isoflavan, vestitol (3); a pterocarpan, medicarpin (4); two prenylflavanones, 8-prenylnaringenin (7) and 6-prenylnaringenin (8); and two geranyl flavonoids, propolin D (9) and macarangin (10). The tenth was elucidated as a previously undescribed dihydrobenzofuran (6). The isolated compounds were tested against Trypanosoma brucei and displayed moderate to high activity. Some of the compounds tested had similar activity against wild type T. brucei and two strains displaying pentamidine resistance.

CONCLUSION: Nigerian propolis from RSN has some similarities with Brazilian red propolis. The propolis displayed anti-trypanosomal activity at a potentially useful level. 

LanguageEnglish
Pages107–115
Number of pages9
JournalPhytochemical Analysis
Volume27
Issue number2
Early online date11 Dec 2015
DOIs
Publication statusPublished - 31 Mar 2016

Fingerprint

Propolis
Trypanosoma brucei
Trypanosoma brucei brucei
propolis
Bioactivity
bioactive properties
Nigeria
Rivers
rivers
Pterocarpans
isoflavans
Chemical analysis
medicarpin
High Pressure Liquid Chromatography
Flavanones
Pentamidine
flavanones
Fractionation
Flavonoids
purity

Keywords

  • prenylated flavonoids
  • benzofuran
  • pentamidine resistance
  • Nigerian Red Propolis

Cite this

Omar, Ruwida M K ; Igoli, John ; Gray, Alexander I ; Ebiloma, Godwin Unekwuojo ; Clements, Carol ; Fearnley, James ; Edrada Ebel, Ru Angeli ; Zhang, Tong ; De Koning, Harry P ; Watson, David G. / Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei. In: Phytochemical Analysis. 2016 ; Vol. 27, No. 2. pp. 107–115 .
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Omar, RMK, Igoli, J, Gray, AI, Ebiloma, GU, Clements, C, Fearnley, J, Edrada Ebel, RA, Zhang, T, De Koning, HP & Watson, DG 2016, 'Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei' Phytochemical Analysis, vol. 27, no. 2, pp. 107–115 . https://doi.org/10.1002/pca.2605

Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei. / Omar, Ruwida M K; Igoli, John; Gray, Alexander I; Ebiloma, Godwin Unekwuojo; Clements, Carol; Fearnley, James; Edrada Ebel, Ru Angeli; Zhang, Tong; De Koning, Harry P; Watson, David G.

In: Phytochemical Analysis, Vol. 27, No. 2, 31.03.2016, p. 107–115 .

Research output: Contribution to journalArticle

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T1 - Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei

AU - Omar, Ruwida M K

AU - Igoli, John

AU - Gray, Alexander I

AU - Ebiloma, Godwin Unekwuojo

AU - Clements, Carol

AU - Fearnley, James

AU - Edrada Ebel, Ru Angeli

AU - Zhang, Tong

AU - De Koning, Harry P

AU - Watson, David G

N1 - This is the peer reviewed version of the following article: Omar, R. M. K., Igoli, J., Gray, A. I., Ebiloma, G. U., Clements, C., Fearnley, J., ... Watson, D. G. (2016). Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei. Phytochemical Analysis., which has been published in final form at hhtp://www.dx.doi.org/10.1002/pca.2605. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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N2 - INTRODUCTION: A previous study showed the unique character of Nigerian red propolis from Rivers State, Nigeria (RSN), with regards to chemical composition and activity against Trypanosoma brucei in comparison with other African propolis.OBJECTIVE: To carry out fractionation and biological testing of Nigerian propolis in order to isolate compounds with anti-trypanosomal activity. To compare the composition of the RSN propolis with the composition of Brazilian red propolis.METHODOLOGY: Profiling was carried out using HPLC-UV-ELSD and HPLC-Orbitrap-FTMS on extracts of two samples collected from RSN with data extraction using MZmine software. Isolation was carried out by normal phase and reversed phase MPLC. Elucidation of the compounds with a purity > 95% was performed by 1D/2D NMR HRMS and HRLC-MS(n) .RESULTS: Ten phenolic compounds were isolated or in the case of liquiritigenin partially purified. Data for nine of these correlated with literature reports of known compounds i.e. one isoflavanone, calycosin (1); two flavanones, liquiritigenin (2) and pinocembrin (5); an isoflavan, vestitol (3); a pterocarpan, medicarpin (4); two prenylflavanones, 8-prenylnaringenin (7) and 6-prenylnaringenin (8); and two geranyl flavonoids, propolin D (9) and macarangin (10). The tenth was elucidated as a previously undescribed dihydrobenzofuran (6). The isolated compounds were tested against Trypanosoma brucei and displayed moderate to high activity. Some of the compounds tested had similar activity against wild type T. brucei and two strains displaying pentamidine resistance.CONCLUSION: Nigerian propolis from RSN has some similarities with Brazilian red propolis. The propolis displayed anti-trypanosomal activity at a potentially useful level. 

AB - INTRODUCTION: A previous study showed the unique character of Nigerian red propolis from Rivers State, Nigeria (RSN), with regards to chemical composition and activity against Trypanosoma brucei in comparison with other African propolis.OBJECTIVE: To carry out fractionation and biological testing of Nigerian propolis in order to isolate compounds with anti-trypanosomal activity. To compare the composition of the RSN propolis with the composition of Brazilian red propolis.METHODOLOGY: Profiling was carried out using HPLC-UV-ELSD and HPLC-Orbitrap-FTMS on extracts of two samples collected from RSN with data extraction using MZmine software. Isolation was carried out by normal phase and reversed phase MPLC. Elucidation of the compounds with a purity > 95% was performed by 1D/2D NMR HRMS and HRLC-MS(n) .RESULTS: Ten phenolic compounds were isolated or in the case of liquiritigenin partially purified. Data for nine of these correlated with literature reports of known compounds i.e. one isoflavanone, calycosin (1); two flavanones, liquiritigenin (2) and pinocembrin (5); an isoflavan, vestitol (3); a pterocarpan, medicarpin (4); two prenylflavanones, 8-prenylnaringenin (7) and 6-prenylnaringenin (8); and two geranyl flavonoids, propolin D (9) and macarangin (10). The tenth was elucidated as a previously undescribed dihydrobenzofuran (6). The isolated compounds were tested against Trypanosoma brucei and displayed moderate to high activity. Some of the compounds tested had similar activity against wild type T. brucei and two strains displaying pentamidine resistance.CONCLUSION: Nigerian propolis from RSN has some similarities with Brazilian red propolis. The propolis displayed anti-trypanosomal activity at a potentially useful level. 

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KW - benzofuran

KW - pentamidine resistance

KW - Nigerian Red Propolis

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