14.77，4888，14.60，24.40，18.67，686,1640mmol•L-1，II i则不具有清除DPPH·的能力。
用无水乙醇配制4个浓度的阿魏酸及其类似物的乙醇溶液，以CuSO4-phen-Vc-H2O2为OH·发生系统，用化学发光分析仪测定OH·发生系统所产生的光强，并观察加入阿魏酸或其类似物溶液后对发光强度的影响，综合数据后求得各个化合物对OH·的清除能力。
结果：FA，II a～II h的IC50分别是3.64，23.45，1.59，23.64，2.05，3.07，
北京市人口与计划生育条例修正案2.77，16.33，24.17 mmol•L-1，II i则不具有清除OH·的能力。
四、阿魏酸及其类似对心肌细胞缺氧/复氧损伤的保护作用 建立心肌细胞缺氧－复氧模型，培养细胞随机分成对照组、溶剂组、缺氧组、加药组，加药组中加入阿魏酸或其类似物的DMSO溶液 (100 mmol·L-1) ，以肌酸激酶（CK）、超氧化物歧化酶（SOD）、乳酸脱氢酶（LDH）、丙二醛（MDA）为观察指标，考察阿魏酸及其类似物对心肌细胞缺氧－复氧损伤的保护作用。
结果：与缺氧/复氧组比较，阿魏酸及部分其类似物可以明显减少因缺氧/复氧损伤所造成的CK、LDH的渗出（P<0.01），CK的减少量介于34.73%－85.56%，而LDH的减少量介于70.11％－72.38％。同时阿魏酸及部分其类似物也可以减轻SOD的酶活力的下降（P<0.01），幅度介于20.43%－70.79。
结论：阿魏酸及其类似物苯环上3，5位取代基可以明显地影响此类化合物抗氧化活性，甲氧基和乙氧基可明显提高活性，溴次之，硝基则降低活性。
关键词：阿魏酸；类似物；抗氧化剂；DPPH·；羟自由基；化学发光；自由基；药物合成；缺氧/复氧；
Synthesis and Evaluation of Ferulic Acid and Its Analogs as
Antioxidants
Master Degree Candidate: Huayong Huang
Tutor：Prof. Jinhong Zheng
ABSTRACT
泡花碱
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid, also named as Ferulic acid (FA) , which widely distributed in plants. FA is one of the strongest bioactive compounds in angelica, equisetum, and other Chinese herbal medicine. Because of its strong antioxidant activity, FA was widely used in medicine, cosmetic and health food. Recently, FA’s biological activity has been extensively studied, and found many its related compounds also have the antioxidant activity. At present, the structure modifications to FA are mainly focused on the carboxyl group. FA’s ester, acyl and salt form were reported. But the modification to FA’s aromatic ring was seldom reported, so we synthesize a series of hydroxycinnamic acid derivatives. The antioxidant activities in vitro were evaluated by the level of scavenging DPPH radicals and hydroxyl radicals. Using the myocardial cell hypoxia/reoxygenation (H/R) model investigate the effect of defending the injury induced by H/R.
1 Synthesize Ferulic Acid and Its Analogs
Synthesize the related substituted 4-hydroxybenzaldehyde, and d ifferent substituted 4-hydroxybenzaldehyde was reacted with maloic acid to synthesize Ferulic acid and its analogs. Their chemical structures were determined by IR, 1HNMR, MS and elemental analysis.无政府主义
Result: Target compounds were white or yellow crystal, melting point were about 200~230℃. Data of Elemental Analysis and Spectroscopy were coincident with character of chemical structure.
2 Scavenging DPPH·activity of Ferulic Acid and Its Analogs
民族论坛Target compounds were prepared to five different level DMSO solution, and
then determined the scavenging rate to DPPH·by spectrophotometry. The scavenging activities of tested compounds were measured as decrease in absorbance of the DPPH·expressed as a percentage of the absorbance of a control DPPH·solution without test compounds. IC50 values were obtained from the probit module in SPSS, which is one professional statistical analysis system.
Result: The IC50 of scavenging activity on DPPH·of target compounds (FA, II a～II h) were 24.40，444618，14.77，4888，14.60，24.40，18.67，686,1640mmol •L-1.Compound II i have no effect on DPPH·.
3 Scavenging OH·activity of Ferulic Acid and Its Analogs
Target compounds were prepared to four different level alcohol solution. Produce OH·by CuSO4-phen-Vc-H2O2 system. The amount of OH·was Evaluated by determining the intensity of chemiluminescence. Different compounds alcohol solution were added to the system, recorded the intensity of chemiluminescence. The scavenging activities of tested compounds were measured as decrease in intensity of chemiluminescence of the OH·expressed as a percentage of the intensity of a control CuSO4-phen-Vc-H2O2 system without test compounds. IC50values were obtained from the probit module in SPSS, which is one professional statistical analysis system.
Result: The IC50 of scavenging activity on DPPH·of target compounds (FA, II a～II h) were 3.64，23.45，1.59，23.64，2.05，3.07，2.77，16.33，24.17 mmol•L-1.Compound II i have no effect on OH·.
4 Protective effect of Ferulic Acid and Its Analogs on myocardial cell ischemia and reperfusion injury
Cultured myocardial cells and divided into four group: control group, solution group, I/R group and drug group. Drug groups were added the DMSO solution of target compounds to the culture fluid, reoxygenation of 1 h following anoxia of 3 h. The activity of LDH and CK in culture, the contents of intracelluar MDA, the activity of SOD of the cultured myocardial cell were measured at the end of experiment.
Result: Compared with Control group, anoxia/reoxygenation caused great increases of levels of LDH, CK, MDA, decreases of activity of SOD; FA and some its analogs significantly attenuated these increase and decreases.
Conclusion: 3 and 5 substituted group on benzene ring of Ferulic acid and its analogs could obviously influence the antioxidant activities, that could be increased by methoxyl , oxethyl or bromine on benzene ring, whereas decreased by nitryl.
Key words: Ferulic acid; antioxidant; DPPH; Hydroxyl radicals; chemiluminescence;
free radicals; drug synthesis; anoxia/reoxygenation
缩略语
英文缩写英文全称中文全称
FA Ferulic acid 阿魏酸
ROS Reactive oxygen species 活性氧
SOD Superoxide dismutase 超氧化物岐化酶
CAT Catalse 过氧化氢酶
CK Creatine Kinase 肌酸激酶
关于进一步规范地方政府举债融资行为的通知GSH-Px Glutathione peroxidase 谷胱甘肽过氧化物酶MDA Malondialdehyde 丙二醛
DPPH Di-Phehcryl Picryl Hydrazal 1,1-二苯基苦基苯肼
自由基
DMSO Dimethyl sulfoxide 二甲基亚砜教师节感恩卡
Phen 1,10-Phenanthroline monohydrate 邻菲罗啉
XOD Xantine oxidase 黄嘌呤氧化酶
XD Xanthine dehydrogenase 黄嘌呤脱氧氢酶ATP Adenosine Trphosphate 三磷酸腺苷
NOS Nitric oxide synthase 一氧化氮酶
cNOS Constitutive NOS 结构型一氧化氮酶PMNs Polymorphonuclear neutrophils 多核型中性粒细胞NADPH Triphosphopyridine nucleotide, 还原型烟酰胺腺嘌呤reduce form 二核苷酸磷酸
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