Chromatographic analysis with different detectors in the chemical characterisation and dereplication of African propolis

Zhang, Tong; Omar, Ruwida; Siheri, Weam; Mutairi, Sultan Al; Clements, Carol; Fearnley, James; Edrada-Ebel, RuAngelie; Watson, David

doi:10.1016/j.talanta.2013.11.094

Cited by 49 publications

(33 citation statements)

References 29 publications

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“…brucei . We were interested in the occurrence of guttiferone isomers, which we had observed in Rivers State propolis samples in our earlier study 5 and speculated that these might be responsible for the high anti-trypanosomal activity of the of the samples since we had previously observed very high activity for a phloroglucinone compound isolated from Cameroonian propolis 23 . However, as can be seen in the extracted ion traces shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…It has a complex chemical composition, which depends on the local flora at the site of collection as well as the season of collection, and this makes it difficult and challenging to standardise 3 . Chemometric methods are being increasingly applied in order to standardise complex samples 4 and have recently been applied to MS data obtained from propolis 5 . Since propolis consists of a wide range of organic compounds of varying polarity and ionisability, complementary techniques have been used in parallel to get a complete profile.…”

Section: Introductionmentioning

confidence: 99%

“…Since propolis consists of a wide range of organic compounds of varying polarity and ionisability, complementary techniques have been used in parallel to get a complete profile. In our previous work we examined propolis collected from many parts of Africa using a range of analytical methods 5 and observed that there was no clear geographic delineation for the classification of these African propolis samples. One sample from Rivers State, Nigeria stood out as having a unique chemical composition and strong anti-trypanosomal activity and we went on to isolate ten compounds from this sample, which all displayed some degree of anti-trypanosomal activity 6 .…”

Section: Introductionmentioning

confidence: 99%

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The Chemical Characterization of Nigerian Propolis samples and Their Activity Against Trypanosoma brucei

Omar

Igoli

Zhang

et al. 2017

Sci Rep

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Profiling of extracts from twelve propolis samples collected from eight regions in Nigeria was carried out using high performance liquid chromatography (LC) coupled with evaporative light scattering (ELSD), ultraviolet detection (UV) and mass spectrometry (MS), gas chromatography mass spectrometry (GC-MS) and nuclear magnetic resonance spectroscopy (NMR). Principal component analysis (PCA) of the processed LC-MS data demonstrated the varying chemical composition of the samples. Most of the samples were active against Trypanosoma b. brucei with the highest activity being in the samples from Southern Nigeria. The more active samples were fractionated in order to isolate the component(s) responsible for their activity using medium pressure liquid chromatography (MPLC). Three xanthones, 1,3,7-trihydroxy-2,8-di-(3-methylbut-2-enyl)xanthone, 1,3,7-trihydroxy-4,8-di-(3-methylbut-2-enyl)xanthone a previously undescribed xanthone and three triterpenes: ambonic acid, mangiferonic acid and a mixture of α-amyrin with mangiferonic acid (1:3) were isolated and characterised by NMR and LC-MS. These compounds all displayed strong inhibitory activity against T.b. brucei but none of them had higher activity than the crude extracts. Partial least squares (PLS) modelling of the anti-trypanosomal activity of the sample extracts using the LC-MS data indicated that high activity in the extracts, as judged from LCMS2 data, could be correlated to denticulatain isomers in the extracts.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Chemical Characterization of Nigerian Propolis samples and Their Activity Against Trypanosoma brucei

Omar

Igoli

Zhang

et al. 2017

Sci Rep

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“…Identified metabolites are mainly caffeic acid derivatives and triterpenoids. Indeed, diverse caffeic acid derivatives already described in propolis extracts from Brazil and sub-Saharan African countries [33, 34] have been detected as caffeic acid 4- O -arabinoside ( m/z = 311.0768), caffeic acid 4-O-xyloside ( m/z 311.0768), caffeoylquinic acid ( m/z = 353.0878), caffeic acid 4- O -glucoside ( m/z = 341.0868) and 3,4-dimethyl caffeic acid ( m/z = 207.0656). Herein it was not possible to distinguish caffeic acid 4- O -arabinoside from caffeic acid 4- O -glucoside that is why they were noted as caffeic acid pentoside.…”

Section: Resultsmentioning

confidence: 99%

Ethanol-extracted Cameroonian propolis exerts estrogenic effects and alleviates hot flushes in ovariectomized Wistar rats

Zingue

Nde

Michel

et al. 2017

BMC Complement Altern Med

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BackgroundSince the biological properties of propolis depend to the plants that can be found in a specific region, propolis from unexplored regions attracts the attention of scientists. Ethanolic extract of Cameroonian propolis (EEP) is used to treat various ailments including gynecological problems and amenorrhea. Since there were no scientific data to support the above claims, the present study was therefore undertaken to assess estrogenic properties of Cameroonian propolis.MethodsTo achieve our goal, the ability of EEP to induce MCF-7 cells proliferation in E-screen assay as well as to activate estrogen receptors α (ERα) and β (ERβ) in cell-based reporter gene assays using human embryonic kidney cells (HEK293T) transfected with ERs was tested. Further, a 3-day uterotrophic assay was performed and the ability of EEP to alleviate hot flushes in ovariectomized adult rats was evaluated.ResultsIn vitro, EEP showed an antiestrogenic activity in both HEK293T ER-α and ER-β cells. In vivo, EEP induced a significant increase in a bell shape dose response manner of the uterine wet weight, the total protein levels in the uterus, the uterine and vaginal epithelium height and acini border cells of mammary gland with the presence of abundant eosinophil secretions. Moreover, EEP induced a significant decrease in the total number, average duration as well as frequency of hot flushes after 3 days of treatment in rat (equivalent to a month in woman). The dose of 150 mg/kg exhibited the most potent estrogenic effects among all the tested doses. The UPLC-HRMS analysis showed the presence of caffeic acid derivatives and trirtepernoids in EEP, which are well known endowed with estrogenic properties.ConclusionThese results suggest that Ethanolic extract of Cameroonian propolis has estrogen-like effects in vivo and may alleviate some menopausal problems such as vaginal dryness and hot flushes.Graphical abstractEthanol-extracted Cameroobian propolis exhibited in vitro and in vivo estrogen-like effects. This extract may contain promising phytoestrogens.

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“…Testing was carried out for the other isolated compounds against a wild‐type strain and against two resistant strains (Table ) of T. brucei . The compounds showed strong anti‐trypanosomal activity with EC 50 values (typical curves shown in Supporting Information S5) against a standardised strain ranging from 4.2 µg/mL for the crude RSN fraction to 16.6 µg/mL for riverinol ( 6 ), confirming the previously observed high activity of the crude extract when compared with other African propolis samples (Zhang et al ., ). Of the purified compounds, 8‐prenylnarigenin ( 8 ) was the most active against the wild‐type strain at 6.1 ± 0.1 µg/mL but macarangin ( 10 ) and vestitol ( 4 ) displayed very similar activities.…”

Section: Resultsmentioning

confidence: 99%

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

Omar

Igoli

Gray

et al. 2015

Phytochemical Analysis

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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‐MSn. 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. Copyright © 2015 John Wiley & Sons, Ltd.

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Chromatographic analysis with different detectors in the chemical characterisation and dereplication of African propolis

Cited by 49 publications

References 29 publications

The Chemical Characterization of Nigerian Propolis samples and Their Activity Against Trypanosoma brucei

The Chemical Characterization of Nigerian Propolis samples and Their Activity Against Trypanosoma brucei

Ethanol-extracted Cameroonian propolis exerts estrogenic effects and alleviates hot flushes in ovariectomized Wistar rats

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

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