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在碱性条件下通过化学氧化对天然原花青素低聚物和聚合物进行改性

Modification of Natural Proanthocyanidin Oligomers and Polymers Via Chemical Oxidation under Alkaline Conditions.

作者信息

Imran Iqbal Bin, Karonen Maarit, Salminen Juha-Pekka, Engström Marica T

机构信息

Natural Chemistry Research Group, Department of Chemistry, University of Turku, Turku FI-20014, Finland.

出版信息

ACS Omega. 2021 Feb 9;6(7):4726-4739. doi: 10.1021/acsomega.0c05515. eCollection 2021 Feb 23.

DOI:10.1021/acsomega.0c05515
PMID:33644580
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7906247/
Abstract

We tested the susceptibility of 102 proanthocyanidin (PA)-rich plant extracts to oxidation under alkaline conditions and the possibility to produce chemically modified PAs via oxidation. Both the nonoxidized and the oxidized extracts were analyzed using group-specific ultrahigh-performance liquid chromatography-diode array detection-tandem mass spectrometry (UHPLC-DAD-MS/MS) methods capable of detecting procyanidin (PC) and prodelphinidin (PD) moieties along the two-dimensional (2D) chromatographic fingerprints of plant PAs. The results indicated different reactivities for PCs and PDs. When detected by UHPLC-DAD only, most of the PC-rich samples exhibited only a subtle change in their PA content, but the UHPLC-MS/MS quantitation showed that the decrease in the PC content varied by 0-100%. The main reaction route was concluded to be intramolecular. The PD-rich and galloylated PAs showed a different pattern with high reductions in the original PA content by both ultraviolet (UV) and MS/MS quantitation, accompanied by the shifted retention times of the chromatographic PA humps. In these samples, both intra- and intermolecular reactions were indicated.

摘要

我们测试了102种富含原花青素（PA）的植物提取物在碱性条件下的氧化敏感性以及通过氧化产生化学修饰PA的可能性。使用能够沿植物PA的二维（2D）色谱指纹图谱检测原花青素（PC）和原飞燕草素（PD）部分的组特异性超高效液相色谱 - 二极管阵列检测 - 串联质谱（UHPLC-DAD-MS/MS）方法对未氧化和氧化的提取物进行分析。结果表明PC和PD具有不同的反应活性。仅通过UHPLC-DAD检测时，大多数富含PC的样品其PA含量仅表现出细微变化，但UHPLC-MS/MS定量显示PC含量的降低幅度在0 - 100%之间变化。主要反应途径被认为是分子内的。富含PD和没食子酰化的PA表现出不同的模式，通过紫外（UV）和MS/MS定量，原始PA含量大幅降低，同时色谱PA峰的保留时间发生偏移。在这些样品中，表明存在分子内和分子间反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/28ecb7acb3fb/ao0c05515_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/8769a9dffe9d/ao0c05515_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/f80fbaa9753d/ao0c05515_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/41d36a949798/ao0c05515_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/c065c68b1b5e/ao0c05515_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/28ecb7acb3fb/ao0c05515_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/8769a9dffe9d/ao0c05515_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/f80fbaa9753d/ao0c05515_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/41d36a949798/ao0c05515_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/c065c68b1b5e/ao0c05515_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a98/7906247/28ecb7acb3fb/ao0c05515_0006.jpg

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