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  

Synthesis and Antioxidant Activity of 1,2,3,5,6,7-Hexahydroxy-9,10-Anthraquinone

作　　者：雷响 张闽峰 胡可欣 柯宇 郑德勇[1] LEI Xiang;ZHANG Minfeng;HU Kexin;KE Yu;ZHENG Deyong(College of Material Engineering,Fujian Agriculture and Forestry University,Fuzhou 350002,China)

机构地区：[1]福建农林大学材料工程学院,福建福州350002

出　　处：《林产化学与工业》2022年第6期64-68,共5页Chemistry and Industry of Forest Products

基　　金：福建农林大学科技创新专项基金资助(CXZX2017036);中央财政林业科技推广示范项目资助(闽[2019]TG17号)。

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(O_(2)^(-)·)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3.25×10^(4) 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·、O_(2)^(-)·的半数抑制浓度(IC_(50))分别为42.1、39.4和30.8μmol/L,其对ABTS^(+)·、DPPH·的清除能力比Vc强,比没食子酸稍弱;对O_(2)^(-)·的清除能力强于Vc和没食子酸。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(O_(2)^(-)·).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 3.25×10^(4) 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(IC 50)of hexahydroxy-anthraquinone for the scavenging of ABTS^(+)·,DPPH·,and O_(2)^(-)·were 42.1,39.4,and 30.8μmol/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 O_(2)^(-)·was stronger than those of Vc and gallic acid.

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 

分 类 号：TQ35[化学工程] TQ244.6