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

Danny A. Van Elswijk, Uwe P. Schobel, Ephraim P. Lansky, Hubertus Irth, Jan Van Der Greef

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)233-241
Number of pages9
JournalPhytochemistry
Volume65
Issue number2
DOIs
StatePublished - Jan 2004
Externally publishedYes

Keywords

  • On-line biochemical detection-mass spectrometry
  • Phytoestrogens
  • Pomegranate
  • Punica granatum

ASJC Scopus subject areas

  • Horticulture
  • Molecular Biology
  • Biochemistry
  • Plant Science

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