Rapid dereplication of estrogenic compounds in pomegranate ( Punica granatum) using on-line biochemical detection coupled to mass spectrometry

During recent years, phytoestrogens have been receiving an increasing amount of interest, as several lines of evidence suggest a possible role in preventing a range of diseases, including the hormonally dependent cancers. In this context, various parts of the pomegranate fruit ( Punica granatum; Pun...

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Published in:	Phytochemistry (Oxford) Vol. 65; no. 2; pp. 233 - 241
Main Authors:	van Elswijk, Danny A, Schobel, Uwe P, Lansky, Ephraim P, Irth, Hubertus, van der Greef, Jan
Format:	Journal Article
Language:	English
Published:	Amsterdam Elsevier Ltd 2004 Elsevier
Subjects:	acid hydrolysis bioactive properties Biological and medical sciences Chemical constitution Chromatography, High Pressure Liquid - instrumentation Chromatography, High Pressure Liquid - methods Estrogens, Non-Steroidal - isolation & purification Flavonoids - isolation & purification fruit trees Fundamental and applied biological sciences. Psychology Glycosylation Kaempferols - isolation & purification Luteolin Lythraceae mass spectrometry Mass Spectrometry - methods On-line biochemical detection–mass spectrometry Phytoestrogens plant estrogens plant extracts Plant Extracts - chemistry Plant physiology and development Pomegranate pomegranates Punica granatum Punicaceae - chemistry Quercetin - isolation & purification spectral analysis Punica granatum Phytoestrogens On-line biochemical detection–mass spectrometry Pomegranate Antineoplastic agent Fruit Molecular structure In vitro On-line biochemical detection-mass spectrometry Biological activity Medicinal plant Phytoestrogen Dicotyledones Angiospermae Quercetin Isolation Punicaceae Spermatophyta Fruit tree Luteolin
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Summary:	During recent years, phytoestrogens have been receiving an increasing amount of interest, as several lines of evidence suggest a possible role in preventing a range of diseases, including the hormonally dependent cancers. In this context, various parts of the pomegranate fruit ( Punica granatum; Punicaceae), e.g. seed oil, juice, fermented juice and peel extract, have been shown to exert suppressive effects on human breast cancer cells in vitro. On-line biochemical detection coupled to mass spectrometry (LC-BCD–MS) was applied to rapidly profile the estrogenic activity in the pomegranate peel extract. The crude mixture was separated by HPLC, after which the presence of biologically active compounds, known or unknown, was detected by means of an on-line β-estrogen receptor (ER) bioassay. Chemical information, such as molecular weight and MS/MS fingerprint, was obtained in real time by directing part of the HPLC effluent towards a mass spectrometer. Using this approach in total three estrogenic compounds, i.e. luteolin, quercetin and kaempferol, were detected and identified by comparing the obtained molecular weights and negative ion APCI MS/MS spectra with the data of an estrogenic compound library. Although well known in literature and widely distributed in nature, the presence of these phytoestrogenic compounds in pomegranate peel extract was not reported previously. Compared to traditional screening approaches of complex mixtures, often characterized by a repeating cycle of HPLC fractionation and biological screening, LC-BCD–MS was shown to profoundly accelerate the time required for compound description and identification. Bioactive compounds, such as kaempferol ( see displayed structure) are rapidly detected and identified in compex mixtures such as natural product extracts.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0031-9422 1873-3700
DOI:	10.1016/j.phytochem.2003.07.001