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木犀草素在亲水性有机溶剂中的糖基化及木犀草素糖苷的结构-抗氧化关系

Glycosylation of luteolin in hydrophilic organic solvents and structure-antioxidant relationships of luteolin glycosides.

作者信息

Xu Tingting, Wang Chen, Jiang Sijie, Yang Tingting, Wu Xueming

机构信息

School of Medicine & Holistic Integrative Medicine, Nanjing University of Chinese Medicine Nanjing 210023 China.

State Key Laboratory Cultivation Base for TCM Quality and Efficacy, School of Pharmacy, Nanjing University of Chinese Medicine Nanjing 210023 China

出版信息

RSC Adv. 2022 Jun 22;12(28):18232-18237. doi: 10.1039/d2ra03300c. eCollection 2022 Jun 14.

DOI:10.1039/d2ra03300c
PMID:35800321
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9214715/
Abstract

An effective approach was developed to biotransform luteolin glycosides in hydrophilic organic solvents. A46 cells showed high activity and stability in 5-20% (v/v) DMSO with 90-98% conversion rates of luteolin glycosides. Five glycosides of luteolin 7--β-glucoside, luteolin 4'--β-glucoside, luteolin 3'--β-glucoside, luteolin 7,3'-di--β-glucoside and luteolin 7,4'-di--β-glucoside were obtained. The addition of DMSO greatly promoted the solubility of luteolin and further regulated the formation of the main products from five luteolin glycosides to luteolin 7--β-glucoside (931.2 μM). Fourteen flavonoids and anthraquinones were used as tentative substrates. Glycosylation positions were located at the C-7, C-3' or C4' hydroxyl groups of flavonoids and C-5 hydroxyl group of anthraquinones. The 3',4'-dihydroxy arrangement played the key role for the antioxidant activity of luteolin.

摘要

开发了一种在亲水性有机溶剂中生物转化木犀草素糖苷的有效方法。A46细胞在5-20%(v/v)二甲基亚砜中表现出高活性和稳定性,木犀草素糖苷的转化率为90-98%。得到了木犀草素的五种糖苷,即木犀草素7-β-葡萄糖苷、木犀草素4'-β-葡萄糖苷、木犀草素3'-β-葡萄糖苷、木犀草素7,3'-二-β-葡萄糖苷和木犀草素7,4'-二-β-葡萄糖苷。二甲基亚砜的添加极大地促进了木犀草素的溶解度,并进一步调节了主要产物从五种木犀草素糖苷到木犀草素7-β-葡萄糖苷(931.2μM)的形成。使用了十四种类黄酮和蒽醌作为试验底物。糖基化位置位于类黄酮的C-7、C-3'或C4'羟基以及蒽醌的C-5羟基上。3',4'-二羟基排列对木犀草素的抗氧化活性起关键作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9396/9214715/cfda62beb28b/d2ra03300c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9396/9214715/3faa6f470dd5/d2ra03300c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9396/9214715/48fef6b71f48/d2ra03300c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9396/9214715/cfda62beb28b/d2ra03300c-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9396/9214715/3faa6f470dd5/d2ra03300c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9396/9214715/48fef6b71f48/d2ra03300c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9396/9214715/cfda62beb28b/d2ra03300c-f3.jpg

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