阿魏酸及其衍生物在食品添加剂领域研究进展
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摘要
阿魏酸及其衍生物抗氧化效果好、性质稳定,且多来自于自然植物,在食品、药品、化妆品领域都有很高的应用价值。本文对阿魏酸及其衍生物的来源、合成、结构和性质进行了简单介绍,并对其在食品添加剂中作为食品抗氧化剂、食品香料、食品交联剂的研究进展进行了综述,最后探讨了可能面临的问题并展望应用前景。
Ferulic acid and its derivatives have good antioxidative effect and are very stable. Most of them come from natural plants and has a wide application in the fields of food,medicine and cosmetics. In this paper,the source,synthesis and structure and properties of ferulic acid and its derivatives were briefly introduced. Also,the research progress in the field of food additives( such as antioxidants,food flavors,and food crosslinker)were reviewed. Finally,the possible problems and expectation about the application were discussed.
Ferulic acid and its derivatives have good antioxidative effect and are very stable. Most of them come from natural plants and has a wide application in the fields of food,medicine and cosmetics. In this paper,the source,synthesis and structure and properties of ferulic acid and its derivatives were briefly introduced. Also,the research progress in the field of food additives( such as antioxidants,food flavors,and food crosslinker)were reviewed. Finally,the possible problems and expectation about the application were discussed.
引文
[1]刘珂伟,傅茂润.阿魏酸的研究进展[J].江苏调味副食品,2016(1):7-10.
[2]Ghatak S B,Panchal S J.Ferulic Acid-An Insight Into Its Current Research and Future Prospects[J].Trends in Food Science&Technology,2010.
[3]尤新.植物种子皮壳中抗氧化剂阿魏酸与人体健康[J].食品与生物技术学报,2012,31(7):673-677.
[4]Grabber J H,Hatfield R J,Zon J,et al.FERULATECROSS-LINKING IN CELL WALLS ISOLATED FROMMAIZE CELL SUSPENSIONS[J].Phytochemistry,1995,40(4):1077-1082.
[5]H?kkinen S H,K?renlampi S O,Heinonen I M,et al.Content of the flavonols quercetin,myricetin,and kaempferol in 25edible berries.[J].Journal of Agricultural&Food Chemistry,1999,47(6):2274-9.
[6]欧仕益,张颖,张景,等.碱解麦麸制备阿魏酸的研究[J].食品科学,2002,23(8):162-165.
[7]Wang L,Zhang R,Ma Z,et al.A feruloyl esterase(FAE)characterized by relatively high thermostability from the edible mushroom Russula virescens[J].Applied Biochemistry&Biotechnology,2014,172(2):993-1003.
[8]Wang L,Ma Z,Du F,et al.Feruloyl esterase from the edible mushroom Panus giganteus:a potential dietary supplement.[J].J.Agric.Food Chem.,2014,62(31):7822-7827.
[9]莫若莹,邵国贤,朱丽莲,等.阿魏酸衍生物的合成[J].药学学报,1985(8).
[10]Chenault J,Dupin[J].Synthetic Communications,1984,14(11):1059-1065.
[11]何良波,雍晓华,朱从才,等.微波辅助阿魏酸合成的工艺研究[J].石河子大学学报(自然科学版),2010,28(6):754-756.
[12]子辉,李婉.含阿魏酸基的氟虫腈衍生物的合成与表征[J].有机氟工业,2017(4).
[13]潘万里.阿魏酸衍生物的设计、合成及多靶点抗AD生物活性研究[D].南阳师范学院,2017.
[14]高晓慧.阿魏酸衍生物的设计、合成及抑制乙酰胆碱酯酶的构效关系研究[D].湖南中医药大学,2017.
[15]刘策,魏一明,冉曼,等.4-羟基-3-甲氧基肉桂酸衍生物的合成及除草活性初步测定[C].全国杂草科学大会.2017.
[16]敖桂珍,程坚,贾佳,等.一种阿魏酸衍生物、制剂及其应用:,CN105693689A[P].2016.
[17]石翛然.DCC/DMAP催化制备乙酰阿魏酸乙酯[J].广州化工,2014(23):106-107.
[18]刘强,刘文彬,黄珍辉,等.三乙胺催化合成乙酰阿魏酸丹皮酚酯[J].湖南中医药大学学报,2015,35(3):34-36.
[19]李泉荟,辛嘉英,王艳,等.非水相脂肪酶催化阿魏酸淀粉酯的合成[J].精细化工,2016,33(11):1266-1271.
[20]何粉霞,聂小伟.有机相脂肪酶催化合成阿魏酸葡萄糖酯的工艺研究[J].粮食与油脂,2018(1):89-91.
[21]陈林林,李伟,辛嘉英.非水相酶促合成阿魏酸酯及其对自由基的清除[J].中国粮油学报,2016,31(7):120-125.
[22]刘强,刘文彬,黄珍辉,等.三乙胺催化合成乙酰阿魏酸丹皮酚酯[J].湖南中医药大学学报,2015,35(3):34-36.
[23]马逢时,李家明,李传润,等.阿魏酸衍生物及其生物活性[J].药学进展,2008,32(8):345-350.
[24]Liu S,Wei W,Li Y,et al.Design,synthesis,biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents[J].European Journal of Medicinal Chemistry,2015,95:473-482.
[25]张海龙.阿魏酸及其衍生物的合成研究[D].合肥工业大学,2017.
[26]Liu H R,Liu L B,Gao X H,et al.Novel ferulic amide derivatives with tertiary amine sidechain as acetylcholine sterase and butyrylchol inesterase inhibitors:The influence ofcarbon spacer length,alkylamine and aromatic group.European Journal of MedicinalChemistry,2017,126,(1):810-822.
[27]Wang Z,Xie D,Gan X,et al.Synthesis,antiviral activity,and molecular docking study of trans-ferulic acid derivatives containing acylhydrazone moiety[J].Bioorganic&Medicinal Chemistry Letters,2017,27(17).
[28]杨采风.壳聚糖羟基肉桂酸衍生物的制备及其抑菌活性的研究[D].江苏科技大学,2016.
[29]中华人民共和国食品安全法[S].北京:中国法制出版社,2009.
[30]尤新.植物种子皮壳中抗氧化剂阿魏酸与人体健康[J].食品与生物技术学报,2012,31(7):673-677.
[31]辛嘉英,赵冠里,郑妍.阿魏酸及其衍生物对食用油脂抗氧化效果的评价[J].食品研究与开发,2006,27(2):167-170.
[32]谢先吉,王临润,吴文娟.经通口服液中阿魏酸含量测定方法的研究[J].药物分析杂志,2005(8):992-993.
[33]胡森科,于燕,张敬华,等.健脾补血片中阿魏酸的质量浓度测定[J].西安交通大学学报(医学版),2006,27(3):304-306.
[34]夏秀东,王英,刘小莉,等.添加外源阿魏酸和茶多酚对蓝莓渣干粉功能成分的影响[J].江西农业学报,2017,29(2):74-78.
[35]姜瑞平,李颖,李博琦,等.阿魏酸在蒸煮香肠中对亚硝酸盐残留量的影响[J].通化师范学院学报,2013,34(6):56-57.
[36]Lesage-Meessen L,Delattre M,Haon M,et al.A two-step bioconversion process for vanillin production from ferulic acid combining Aspergillus niger and Pycnoporus cinnabarinus[J].Journal of Biotechnology,1996,50(2/3):107-113.
[37]Hua D L,Ma C Q,Song L F,et al.Enhanced vanillin production from ferulic acid using adsorbent resin[J].Applied Microbiology and Biotechnology,2007,74(4):783-790.
[38]Fleige C,Meyer F,Steinbüchel A.Metabolic engineering of the actinomycete Amycolatopsis sp.ATCC 39116towards enhanced production of natural vanillin[J].Applied&Environmental Microbiology,2016,82(11):AEM.00802-16.
[39]Dulong V,Kouassi M C,Labat B,et al.Antioxidant properties and bioactivity of Carboxymethylpullulan grafted with ferulic acid and of their hydrogels obtained by enzymatic reaction[J].Food Chemistry,2018.
[40]贾潇,赵谋明,贾春晓,等.大米蛋白与阿魏酸酶法交联物的乳化特性和抗氧化稳定性[J].食品科学,2017,38(13):131-137.
[41]肖乃玉,卢曼萍,陈少君,等.阿魏酸-胶原蛋白抗菌膜在腊肠保鲜中的应用[J].食品与发酵工业,2014,40(4):210-215.
[42]陈达佳.胶原蛋白-壳聚糖可食用复合膜的制备、改性及应用[D].江西科技师范大学,2014.
[2]Ghatak S B,Panchal S J.Ferulic Acid-An Insight Into Its Current Research and Future Prospects[J].Trends in Food Science&Technology,2010.
[3]尤新.植物种子皮壳中抗氧化剂阿魏酸与人体健康[J].食品与生物技术学报,2012,31(7):673-677.
[4]Grabber J H,Hatfield R J,Zon J,et al.FERULATECROSS-LINKING IN CELL WALLS ISOLATED FROMMAIZE CELL SUSPENSIONS[J].Phytochemistry,1995,40(4):1077-1082.
[5]H?kkinen S H,K?renlampi S O,Heinonen I M,et al.Content of the flavonols quercetin,myricetin,and kaempferol in 25edible berries.[J].Journal of Agricultural&Food Chemistry,1999,47(6):2274-9.
[6]欧仕益,张颖,张景,等.碱解麦麸制备阿魏酸的研究[J].食品科学,2002,23(8):162-165.
[7]Wang L,Zhang R,Ma Z,et al.A feruloyl esterase(FAE)characterized by relatively high thermostability from the edible mushroom Russula virescens[J].Applied Biochemistry&Biotechnology,2014,172(2):993-1003.
[8]Wang L,Ma Z,Du F,et al.Feruloyl esterase from the edible mushroom Panus giganteus:a potential dietary supplement.[J].J.Agric.Food Chem.,2014,62(31):7822-7827.
[9]莫若莹,邵国贤,朱丽莲,等.阿魏酸衍生物的合成[J].药学学报,1985(8).
[10]Chenault J,Dupin[J].Synthetic Communications,1984,14(11):1059-1065.
[11]何良波,雍晓华,朱从才,等.微波辅助阿魏酸合成的工艺研究[J].石河子大学学报(自然科学版),2010,28(6):754-756.
[12]子辉,李婉.含阿魏酸基的氟虫腈衍生物的合成与表征[J].有机氟工业,2017(4).
[13]潘万里.阿魏酸衍生物的设计、合成及多靶点抗AD生物活性研究[D].南阳师范学院,2017.
[14]高晓慧.阿魏酸衍生物的设计、合成及抑制乙酰胆碱酯酶的构效关系研究[D].湖南中医药大学,2017.
[15]刘策,魏一明,冉曼,等.4-羟基-3-甲氧基肉桂酸衍生物的合成及除草活性初步测定[C].全国杂草科学大会.2017.
[16]敖桂珍,程坚,贾佳,等.一种阿魏酸衍生物、制剂及其应用:,CN105693689A[P].2016.
[17]石翛然.DCC/DMAP催化制备乙酰阿魏酸乙酯[J].广州化工,2014(23):106-107.
[18]刘强,刘文彬,黄珍辉,等.三乙胺催化合成乙酰阿魏酸丹皮酚酯[J].湖南中医药大学学报,2015,35(3):34-36.
[19]李泉荟,辛嘉英,王艳,等.非水相脂肪酶催化阿魏酸淀粉酯的合成[J].精细化工,2016,33(11):1266-1271.
[20]何粉霞,聂小伟.有机相脂肪酶催化合成阿魏酸葡萄糖酯的工艺研究[J].粮食与油脂,2018(1):89-91.
[21]陈林林,李伟,辛嘉英.非水相酶促合成阿魏酸酯及其对自由基的清除[J].中国粮油学报,2016,31(7):120-125.
[22]刘强,刘文彬,黄珍辉,等.三乙胺催化合成乙酰阿魏酸丹皮酚酯[J].湖南中医药大学学报,2015,35(3):34-36.
[23]马逢时,李家明,李传润,等.阿魏酸衍生物及其生物活性[J].药学进展,2008,32(8):345-350.
[24]Liu S,Wei W,Li Y,et al.Design,synthesis,biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents[J].European Journal of Medicinal Chemistry,2015,95:473-482.
[25]张海龙.阿魏酸及其衍生物的合成研究[D].合肥工业大学,2017.
[26]Liu H R,Liu L B,Gao X H,et al.Novel ferulic amide derivatives with tertiary amine sidechain as acetylcholine sterase and butyrylchol inesterase inhibitors:The influence ofcarbon spacer length,alkylamine and aromatic group.European Journal of MedicinalChemistry,2017,126,(1):810-822.
[27]Wang Z,Xie D,Gan X,et al.Synthesis,antiviral activity,and molecular docking study of trans-ferulic acid derivatives containing acylhydrazone moiety[J].Bioorganic&Medicinal Chemistry Letters,2017,27(17).
[28]杨采风.壳聚糖羟基肉桂酸衍生物的制备及其抑菌活性的研究[D].江苏科技大学,2016.
[29]中华人民共和国食品安全法[S].北京:中国法制出版社,2009.
[30]尤新.植物种子皮壳中抗氧化剂阿魏酸与人体健康[J].食品与生物技术学报,2012,31(7):673-677.
[31]辛嘉英,赵冠里,郑妍.阿魏酸及其衍生物对食用油脂抗氧化效果的评价[J].食品研究与开发,2006,27(2):167-170.
[32]谢先吉,王临润,吴文娟.经通口服液中阿魏酸含量测定方法的研究[J].药物分析杂志,2005(8):992-993.
[33]胡森科,于燕,张敬华,等.健脾补血片中阿魏酸的质量浓度测定[J].西安交通大学学报(医学版),2006,27(3):304-306.
[34]夏秀东,王英,刘小莉,等.添加外源阿魏酸和茶多酚对蓝莓渣干粉功能成分的影响[J].江西农业学报,2017,29(2):74-78.
[35]姜瑞平,李颖,李博琦,等.阿魏酸在蒸煮香肠中对亚硝酸盐残留量的影响[J].通化师范学院学报,2013,34(6):56-57.
[36]Lesage-Meessen L,Delattre M,Haon M,et al.A two-step bioconversion process for vanillin production from ferulic acid combining Aspergillus niger and Pycnoporus cinnabarinus[J].Journal of Biotechnology,1996,50(2/3):107-113.
[37]Hua D L,Ma C Q,Song L F,et al.Enhanced vanillin production from ferulic acid using adsorbent resin[J].Applied Microbiology and Biotechnology,2007,74(4):783-790.
[38]Fleige C,Meyer F,Steinbüchel A.Metabolic engineering of the actinomycete Amycolatopsis sp.ATCC 39116towards enhanced production of natural vanillin[J].Applied&Environmental Microbiology,2016,82(11):AEM.00802-16.
[39]Dulong V,Kouassi M C,Labat B,et al.Antioxidant properties and bioactivity of Carboxymethylpullulan grafted with ferulic acid and of their hydrogels obtained by enzymatic reaction[J].Food Chemistry,2018.
[40]贾潇,赵谋明,贾春晓,等.大米蛋白与阿魏酸酶法交联物的乳化特性和抗氧化稳定性[J].食品科学,2017,38(13):131-137.
[41]肖乃玉,卢曼萍,陈少君,等.阿魏酸-胶原蛋白抗菌膜在腊肠保鲜中的应用[J].食品与发酵工业,2014,40(4):210-215.
[42]陈达佳.胶原蛋白-壳聚糖可食用复合膜的制备、改性及应用[D].江西科技师范大学,2014.