Dynamic Residual Complexity of the Isoliquiritigenin鈥揕iquiritigenin Interconversion During Bioassay

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• 作者：Charlotte Simmler ; Atieh Hajirahimkhan ; David C. Lankin ; Judy L. Bolton ; Tristesse Jones ; Djaja D. Soejarto ; Shao-Nong Chen ; Guido F. Pauli
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2013
• 出版时间：March 6, 2013
• 年：2013
• 卷：61
• 期：9
• 页码：2146-2157
• 全文大小：739K
• 年卷期：v.61,no.9(March 6, 2013)
• ISSN：1520-5118

文摘

Bioactive components in food plants can undergo dynamic processes that involve multiple chemical species. For example, 2鈥?hydroxychalcones can readily isomerize into flavanones. Although chemically well documented, this reaction has barely been explored in the context of cell-based assays. The present time-resolved study fills this gap by investigating the isomerization of isoliquiritigenin (a 2鈥?hydroxychalcone) and liquiritigenin (a flavanone) in two culture media (Dulbecco鈥檚 modified eagle medium and Roswell Park Memorial Institute medium) with and without MCF-7 cells, using high-performance liquid chromatography鈥揹iode array detector鈥揺lectrospray ionization/atmospheric pressure chemical ionization鈥搈ass spectrometry for analysis. Both compounds were isomerized and epimerized under all investigated biological conditions, leading to mixtures of isoliquiritigenin and R/S-liquiritigenin, with 19.6% R enantiomeric excess. Consequently, all three species can potentially modulate the biological responses. This exemplifies dynamic residual complexity and demonstrates how both nonchiral reactions and enantiomeric discrimination can occur in bioassay media, with or without cells. The findings highlight the importance of controlling in situ chemical reactivity, influenced by biological systems when evaluating the mode of action of bioactives.r>

Keywords:

bioassay; epimerization; isoliquiritigenin; isomerization; liquiritigenin; residual complexity