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Int. J. Mol. Sci. 2017, 18(3), 512; doi:10.3390/ijms18030512

Tentative Characterization of Polyphenolic Compounds in the Male Flowers of Phoenix dactylifera by Liquid Chromatography Coupled with Mass Spectrometry and DFT

1
Department of Chemistry, College of Science & Arts at Al-Rass, Qassim University, P.O. 53, 51921 Al-Rass, Saudi Arabia
2
Physico-Chimie des Matériaux à l’état condensé, Department of Chemistry, Faculty of Sciences, University Tunis El Manar, 2092 Tunis, Tunisia
3
Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation, State of Research Institute, ul. CzatRoryskich 8, 24-100 Pulawy, Poland
4
Phytochemistry Laboratory, Department of Botany, Faculty of Science, Aswan University, 81528 Aswan, Egypt
*
Authors to whom correspondence should be addressed.
Academic Editors: Nuno Mateus and Iva Fernandes
Received: 28 December 2016 / Revised: 15 February 2017 / Accepted: 20 February 2017 / Published: 2 March 2017
(This article belongs to the Special Issue Anthocyanins)
View Full-Text   |   Download PDF [2354 KB, uploaded 2 March 2017]   |  

Abstract

Phoenix dacylifera is an ancient palm species rich in (poly)phenols. These phenolic compounds were tentatively identified by using liquid chromatography coupled with ion spray mass spectrometry in tandem mode (LC/MS/MS) with negative ion detection. Negative identification of the compounds was based on their retention times and mass spectra in full scan mode (MS), and in different MS/MS modes. For the first time, complete hypothesis, and routs for both p-coumaroylshikimic acids (CoSA) and caffeoylshikimic acids (CSA) were suggested and confirmed by Density Fonctional Theory (DFT) study. Notably, of the 53 compounds characterized, 19 hydroxycinnamates derivatives were tentativelycharacterized in male flowers of date palm and 15 of them were recorded for the first time. In addition, five organic acids, six B-type proanthocyanidins, two anthocyanidin and 21 flavonoid derivatives have been tentatively characterized. Identification of B-type proanthocyanidins were based on the diagnostic ions resulting from heterocyclic ring fission (HRF) and retro-Diels-Alder (RDA) reaction of flavan-3-ol provided information on the hydroxylation pattern and the type of inter-flavan bond proanthocyanidins. The sequence of proanthocyanidins was detected through ions extracted from quinone methide (QM) cleavage of the inter-flavan bond. View Full-Text
Keywords: Phoenix dactylifera; electrospray ionization; mass spectrometry; p-coumaroylshikimic acids; caffeoylshikimic acids; Density Fonctional Theory (DFT) Phoenix dactylifera; electrospray ionization; mass spectrometry; p-coumaroylshikimic acids; caffeoylshikimic acids; Density Fonctional Theory (DFT)
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Ben Said, R.; Hamed, A.I.; Mahalel, U.A.; Al-Ayed, A.S.; Kowalczyk, M.; Moldoch, J.; Oleszek, W.; Stochmal, A. Tentative Characterization of Polyphenolic Compounds in the Male Flowers of Phoenix dactylifera by Liquid Chromatography Coupled with Mass Spectrometry and DFT. Int. J. Mol. Sci. 2017, 18, 512.

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