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3',8″-二聚体增强黄酮类化合物的抗氧化能力：来自白杨素和黄豆黄素的证据。

3',8″-Dimerization Enhances the Antioxidant Capacity of Flavonoids: Evidence from Acacetin and Isoginkgetin.

机构信息

School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China.

Innovative Research & Development Laboratory of TCM, Guangzhou University of Chinese Medicine, Waihuan East Road No. 232, Guangzhou Higher Education Mega Center, Guangzhou 510006, China.

出版信息

Molecules. 2019 May 28;24(11):2039. doi: 10.3390/molecules24112039.

DOI:10.3390/molecules24112039
PMID:31142008
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6600363/
Abstract

To probe the effect of 3',8″-dimerization on antioxidant flavonoids, acacetin and its 3',8″-dimer isoginkgetin were comparatively analyzed using three antioxidant assays, namely, the O scavenging assay, the Cu reducing assay, and the 2,2'-azino bis(3-ethylbenzothiazolin-6-sulfonic acid) radical scavenging assay. In these assays, acacetin had consistently higher IC values than isoginkgetin. Subsequently, the acacetin was incubated with 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxy radicals (4-methoxy-TEMPO) and then analyzed by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-ESI-Q-TOF-MS) technology. The results of the UHPLC-ESI-Q-TOF-MS analysis suggested the presence of a dimer with / 565, 550, 413, 389, 374, 345, 330, and 283 peaks. By comparison, standard isoginkgetin yielded peaks at / 565, 533, 518, 489, 401, 389, 374, and 151 in the mass spectra. Based on these experimental data, MS interpretation, and the relevant literature, we concluded that isoginkgetin had higher electron transfer potential than its monomer because of the 3',8″-dimerization. Additionally, acacetin can produce a dimer during its antioxidant process; however, the dimer is not isoginkgetin.

摘要

为了探究 3',8″-二聚化对抗氧化黄酮类化合物的影响，使用三种抗氧化测定法（O 清除测定法、Cu 还原测定法和 2,2'-联氮双-3-乙基苯并噻唑啉-6-磺酸自由基清除测定法）对芹黄素及其 3',8″-二聚体异银杏素进行了比较分析。在这些测定法中，芹黄素的 IC 值始终高于异银杏素。随后，将芹黄素与 4-甲氧基-2,2,6,6-四甲基哌啶-1-氧基自由基（4-甲氧基-TEMPO）孵育，然后通过超高效液相色谱-电喷雾电离四极杆飞行时间串联质谱（UHPLC-ESI-Q-TOF-MS）技术进行分析。UHPLC-ESI-Q-TOF-MS 分析结果表明存在一个二聚体，其质荷比（m/z）为 565、550、413、389、374、345、330 和 283。相比之下，标准异银杏素在质谱中产生的峰的质荷比（m/z）为 565、533、518、489、401、389、374 和 151。基于这些实验数据、MS 解释和相关文献，我们得出结论，由于 3',8″-二聚化，异银杏素的电子转移电位高于其单体。此外，芹黄素在其抗氧化过程中可以产生二聚体，但该二聚体不是异银杏素。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5f1/6600363/807575e47d45/molecules-24-02039-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5f1/6600363/1b266c12f8c4/molecules-24-02039-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5f1/6600363/fbc44ec7145c/molecules-24-02039-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5f1/6600363/807575e47d45/molecules-24-02039-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5f1/6600363/1b266c12f8c4/molecules-24-02039-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5f1/6600363/fbc44ec7145c/molecules-24-02039-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b5f1/6600363/807575e47d45/molecules-24-02039-g003.jpg

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