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非酚类氨基香豆素的非典型抗氧化活性。

Atypical antioxidant activity of non-phenolic amino-coumarins.

作者信息

Zúñiga-Núñez Daniel, Barrias Pablo, Cárdenas-Jirón Gloria, Ureta-Zañartu M Soledad, Lopez-Alarcón Camilo, Morán Vieyra F Eduardo, Borsarelli Claudio D, Alarcon Emilio I, Aspée Alexis

机构信息

Facultad de Química y Biología, Universidad de Santiago de Chile (USACH) Casilla 40, Correo 33 Santiago Chile

Departamento de Química Física, Facultad de Química, Pontificia Universidad Católica de Chile Av. Vicuña Mackenna 4860 Santiago Macul Chile.

出版信息

RSC Adv. 2018 Jan 9;8(4):1927-1933. doi: 10.1039/c7ra12000a. eCollection 2018 Jan 5.

DOI:10.1039/c7ra12000a
PMID:35542595
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9077249/
Abstract

Coumarin compounds have been described as anti-inflammatories, and chemotherapeutic agents as well as antioxidants. However, the origin of the antioxidant activity of non phenolic coumarins remains obscure. In the present report, we demonstrate that non-phenolic 7-dialkyl-aminocoumarins may also have significant antioxidant properties against free radicals derived from 2,2'-azobis(2-amidinopropane) dihydrochloride under aerobic conditions. This atypical behaviour is due to the presence of traces of very reactive hydroxycinnamic acid-type compounds. Changing functional groups at the C-3 and C-4 positions shifts the reactivity of the compounds from peroxyl to alkoxyl free radicals. Kinetic and theoretical studies based on Density Functional Theory support the formation of reactive hydroxycinnamic acid and directly link the antioxidant behaviour of the compounds to hydrogen atom transfer.

摘要

香豆素类化合物已被描述为具有抗炎、化疗以及抗氧化作用的药剂。然而，非酚类香豆素的抗氧化活性来源仍不清楚。在本报告中，我们证明了非酚类7-二烷基氨基香豆素在有氧条件下对2,2'-偶氮二异丁脒二盐酸盐产生的自由基也可能具有显著的抗氧化性能。这种非典型行为是由于存在痕量的高反应性羟基肉桂酸型化合物。改变C-3和C-4位的官能团会使化合物的反应性从过氧自由基转变为烷氧自由基。基于密度泛函理论的动力学和理论研究支持了活性羟基肉桂酸的形成，并将化合物的抗氧化行为直接与氢原子转移联系起来。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/407c883b85d5/c7ra12000a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/28af1e9969d0/c7ra12000a-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/c187c6830cf9/c7ra12000a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/ddb807cb0b81/c7ra12000a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/cfdc73654238/c7ra12000a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/99c38a8aaa7c/c7ra12000a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/4d1d696ef51b/c7ra12000a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/407c883b85d5/c7ra12000a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/28af1e9969d0/c7ra12000a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/0a3bc7081bca/c7ra12000a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/c187c6830cf9/c7ra12000a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/ddb807cb0b81/c7ra12000a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/cfdc73654238/c7ra12000a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/99c38a8aaa7c/c7ra12000a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/4d1d696ef51b/c7ra12000a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c454/9077249/407c883b85d5/c7ra12000a-s5.jpg

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