1, 2, 3, 5, 6, 7-六羟基-9, 10-蒽醌的合成及其抗氧化活性研究

doi:10.3969/j.issn.0253-2417.2022.06.009

摘要/Abstract

摘要：

以甲烷磺酸为催化剂, 没食子酸经Friedel-Crafts酰基化反应合成了1, 2, 3, 5, 6, 7-六羟基-9, 10-蒽醌, 通过紫外-可见光(UV-vis)光谱、傅里叶变换红外(FT-IR)光谱、核磁共振(NMR)波谱和液相色谱-质谱联用(LC-MS)等分析手段验证目标产物结构, 并从清除ABTS自由基(ABTS⁺·)、DPPH自由基(DPPH·)和超氧阴离子自由基(O₂^-·)能力评价了六羟基蒽醌的体外抗氧化活性。研究结果表明：1, 2, 3, 5, 6, 7-六羟基-9, 10-蒽醌在最大吸收波长293 nm处的摩尔吸光系数(ε_λmax)为3.25×10⁴ L/(cm·mol), 达到常用紫外吸收剂4-甲氧基肉桂酸-2-乙基己酯(OMC)的2倍多, 是一种性能优良的UVB波段紫外吸收剂；六羟基蒽醌清除ABTS⁺·、DPPH·、O₂^-·的半数抑制浓度(IC₅₀)分别为42.1、39.4和30.8 μmol/L, 其对ABTS⁺·、DPPH·的清除能力比Vc强, 比没食子酸稍弱；对O₂^-·的清除能力强于Vc和没食子酸。

关键词: Friedel-Crafts反应, 没食子酸, 1, 2, 3, 5, 6, 7-六羟基-9, 10-蒽醌, 体外抗氧化活性, 紫外吸收剂

Abstract:

1, 2, 3, 5, 6, 7-hexahydroxy-9, 10-anthraquinone was synthesized by Friedel-Crafts acylation reaction using gallic acid as raw material and methanesulfonic acid as catalyst. The structure of the target product was verified by ultraviolet-visible(UV-vis) spectroscopy, Fourier transform infrared(FT-IR) spectroscopy, nuclear magnetic resonance(NMR) spectroscopy, and liquid chromatography-mass spectrometry(LC-MS) spectroscopy. The antioxidant activities in vitro of hexahydroxy-anthraquinone were evaluated in terms of its scavenging abilities on ABTS radical (ABTS⁺·), DPPH radical(DPPH·) and superoxide anion radical (O₂^-·). The results showed that the molar absorbance coefficient(ε_λmax) of 1, 2, 3, 5, 6, 7-hexahydroxy-9, 10-anthraquinone at the maximum absorption wavelength of 293 nm was 3.25×10⁴ L/(cm·mol), which was two times higher than that of the commonly used UV absorber 4-methoxycinnamic acid-2-ethylhexyl ester(OMC), indicating that it was an excellent UV absorber in UVB band. The half-inhibitory concentrations(IC₅₀) of hexahydroxy-anthraquinone for the scavenging of ABTS⁺·, DPPH·, and O₂^-· were 42.1, 39.4, and 30.8 μmol/L, respectively. The scavenging ability of it on ABTS⁺· and DPPH· was stronger than that of Vc, but weaker than that of gallic acid, and the scavenging ability of it on O₂^-· was stronger than those of Vc and gallic acid.

Key words: Friedel-Crafts reaction, gallic acid, 1, 2, 3, 5, 6, 7-hexahydroxy-9, 10-anthraquinone, antioxidant activity in vitro, UV-absorber

中图分类号:

TQ35
TQ244.6

雷响, 张闽峰, 胡可欣, 柯宇, 郑德勇. 1, 2, 3, 5, 6, 7-六羟基-9, 10-蒽醌的合成及其抗氧化活性研究[J]. 林产化学与工业, 2022, 42(6): 64-68.

Xiang LEI, Minfeng ZHANG, Kexin HU, Yu KE, Deyong ZHENG. Synthesis and Antioxidant Activity of 1, 2, 3, 5, 6, 7-Hexahydroxy-9, 10-Anthraquinone[J]. Chemistry and Industry of Forest Products, 2022, 42(6): 64-68.

图/表 4

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