Tentative Characterization of Polyphenolic Compounds in the Male Flowers of Phoenix dactylifera by Liquid Chromatography Coupled with Mass Spectrometry and DFT.
Tentative Characterization of Polyphenolic Compounds in the Male Flowers of Phoenix dactylifera by Liquid Chromatography Coupled with Mass Spectrometry and DFT.
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DOI：
10.3390/ijms18030512
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发表时间：
2017-03-02
影响因子：
5.6
通讯作者：
Stochmal A
中科院分区：
文献类型：
--
作者：
Ben Said R;Hamed AI;Mahalel UA;Al-Ayed AS;Kowalczyk M;Moldoch J;Oleszek W;Stochmal A
凤凰是一种古老的棕榈物种，富含（多）酚。这些酚类化合物进行了初步鉴定，采用液相色谱-离子喷雾质谱串联模式（LC/MS/MS）与负离子检测器。化合物的阴性鉴别基于其保留时间和全扫描模式（MS）和不同MS/MS模式下的质谱。首次提出了对香豆酰莽草酸（CoSA）和咖啡酰莽草酸（CSA）的完整假设和路线，并通过密度泛函理论（DFT）研究得到证实。其中19个羟基肉桂酸酯衍生物在枣椰雄花中初步鉴定，其中15个为首次发现。此外，还初步鉴定了5种有机酸、6种B型原花青素、2种花青素和21种黄酮类化合物。基于黄烷-3-醇的杂环断裂（HRF）和反Diels-桤木（RDA）反应产生的诊断离子鉴定B型原花青素，提供了关于羟基化模式和黄烷间键合原花青素类型的信息。通过醌甲基化物（QM）提取的离子断裂黄烷间的键来检测原花青素的序列。
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.