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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
chemistry
Structure-oriented UHPLC-LTQ Orbitrap-based approach as a dereplication strategy for the identification of isoflavonoids from Amphimas pterocarpoides crude extract
Journal of Mass Spectrometry, Volume 48, No. 5, Year 2013
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Description
Hyphenated techniques and especially ultra-high performance liquid chromatography-mass spectrometry (UHPLC-MS) are nowadays widely employed in natural products research. However, the complex nature of plant extracts complicates considerably the analysis and the identification of their constituents. Nevertheless, new MS analyzers with increased resolving power and accuracy such as the orbital trap (Orbitrap) could facilitate drastically this process. The objective of this study is the development of a new structure-oriented approach based on fast UHPLC-high-resolution (HR)MS and HRMS/MS methodologies for the identification of isoflavonoids in crude extracts. In addition, aims to assist dereplication procedures, to decrease the laborious isolation steps and orient the focused isolation of compounds of interest. As a proof of concept, the methanol extract of the stem bark of Amphimas pterocarpoides (Leguminosae) was selected. Based on chromatographic (retention time, polarity) and spectrometric features (ultraviolet spectra, accurate m/z, proposed elemental composition, ring double bond equivalent, and relative isotopic abundance) as well as HRMS/MS spectra, several isoflavonoids were identified. In order to verify the proposed structures, 11 isoflavonoids were selectively isolated and unambiguously identified using 1&2D nuclear magnetic resonance techniques. Moreover, the isolated isoflavonoids were studied in HRMS/MS level, employing electrospray ionization and atmospheric pressure chemical ionization sources, in both modes. Useful information regarding their fragmentation patterns was obtained, and characteristic diagnostic ions were defined for the identification of methoxylated isoflavones, dihydroisoflavones and 5-hydroxylated isoflavonoids. Based on the current results, the proposed dereplication strategy was verified and could comprise a novel approach for the analysis of crude extracts in the future not only for isoflavonoids but also for other chemical classes of natural products. Copyright © 2013 John Wiley & Sons, Ltd.
Authors & Co-Authors
Tchoumtchoua, Job
Greece, Athens
National and Kapodistrian University of Athens
Cameroon, Yaounde
Université de Yaoundé I
Njamen, Dieudonné
Cameroon, Yaounde
Université de Yaoundé I
Mbanya, J. C.
Cameroon, Yaounde
Université de Yaoundé I
Skaltsounis, Alexios Leandros
Greece, Athens
National and Kapodistrian University of Athens
Halabalaki, Maria
Greece, Athens
National and Kapodistrian University of Athens
Statistics
Citations: 47
Authors: 5
Affiliations: 2
Identifiers
Doi:
10.1002/jms.3167
ISSN:
10765174
e-ISSN:
10969888
Research Areas
Cancer