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

doi:10.1002/pca.2605

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

Strathclyde Institute Of Pharmacy And Biomedical Sciences

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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.

Original language	English
Pages (from-to)	107–115
Number of pages	9
Journal	Phytochemical Analysis
Volume	27
Issue number	2
Early online date	11 Dec 2015
DOIs	https://doi.org/10.1002/pca.2605
Publication status	Published - 31 Mar 2016

Keywords

prenylated flavonoids
benzofuran
pentamidine resistance
Nigerian Red Propolis

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Omar-etal-PA2015-chemical-characterisation-of-nigerian-res-propolisAccepted author manuscript, 0.99 MB

Libyan propolis raw data
Watson, D. (Creator), University of Strathclyde, 15 Apr 2016
DOI: 10.15129/0b549ed7-de92-4389-8fa0-a36549a3553b
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@article{0fe4a09f5e4f4b0f813005acbdad8d58,

title = "Chemical characterisation of Nigerian red propolis and its biological activity against Trypanosoma Brucei",

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. ",

keywords = "prenylated flavonoids, benzofuran, pentamidine resistance, Nigerian Red Propolis",

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

note = "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.",

year = "2016",

month = mar,

day = "31",

doi = "10.1002/pca.2605",

language = "English",

volume = "27",

pages = "107–115 ",

journal = "Phytochemical Analysis",

issn = "0958-0344",

number = "2",

}

TY - JOUR

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.

PY - 2016/3/31

Y1 - 2016/3/31

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.

KW - prenylated flavonoids

KW - benzofuran

KW - pentamidine resistance

KW - Nigerian Red Propolis

U2 - 10.1002/pca.2605

DO - 10.1002/pca.2605

M3 - Article

C2 - 26662866

SN - 0958-0344

VL - 27

SP - 107

EP - 115

JO - Phytochemical Analysis

JF - Phytochemical Analysis

IS - 2

ER -

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

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