半胱氨酸消减丙烯酰胺的机理及消减工艺在薯条中的应用  

Mechanism of Acrylamide Elimination by Cysteine and Its Application in Potato Chips

作　　者：黄才欢[1] 李丹[1] 龙成艳 郑洁[1] 龚启宙 欧隽滢 HUANG Caihuan;LI Dan;LONG Chengyan;ZHENG Jie;GONG Qizhou;OU Juanying(Department of Food Science and Engineering,Jinan University,Guangzhou 510632,China;Zhongshan Hongli Health Food Industry Research Institute Co.,Ltd.,Zhongshan 528430,China;Institute of Food Safety and Nutrition,Jinan University,Guangzhou 510632,China)

机构地区：[1]暨南大学食品科学与工程系,广东广州510632 [2]中山洪力健康食品产业研究院有限公司,广东中山528430 [3]暨南大学食品安全与营养研究院,广东广州510632

出　　处：《食品工业科技》2022年第22期287-295,共9页Science and Technology of Food Industry

基　　金：广东省自然科学基金(2018A030313064);广州市民生科技攻关计划项目(201903010004);中山火炬现代产业工程技术研究院创新中心项目(2019CYY01002)。

摘　　要：L-半胱氨酸在模拟体系中可显著降低丙烯酰胺的含量,并形成新物质。本研究旨在制备出高纯度的半胱氨酸-丙烯酰胺加合物,阐明半胱氨酸消减丙烯酰胺的机理,并探索该消减工艺在薯片加工中的应用。首先通过优化反应条件,制备目标加合物,使用反相柱层析法分离纯化出高纯度加合物,综合运用质谱、核磁共振和紫外光谱等现代波谱分析技术解析加合物结构,阐析半胱氨酸消减丙烯酰胺的机理;以Caco-2细胞体外实验评估加合物的细胞毒性,通过UPLC-MS检测不同浓度半胱氨酸溶液预处对薯片中丙烯酰胺的消减作用。结果表明:半胱氨酸与丙烯酰胺的物料比为1:3,120℃反应3 h,可获得目标加合物最大生成量;色谱分离可得到纯度达95%的加合物,其紫外最大吸收波长为196 nm,相对分子量为192.0641,分子式为C_(6)H_(9)NO_(3)S,是由半胱氨酸的巯基与丙烯酰胺的烯基通过迈克尔加成反应形成;加合物培养Caco-2细胞24和48 h后,其细胞毒性明显低于丙烯酰胺;在油炸前浸泡薯片的半胱氨酸溶液浓度为3和5 g/L时,薯片中丙烯酰胺的消减率均高于83%,并检测出一定量的加合物。可见,半胱氨酸可通过与丙烯酰胺形成加合物显著降低油炸薯片中的丙烯酰胺含量。L-cysteine can significantly reduce the content of acrylamide and form new substances.To clarify the reduction mechanism and apply it in potato chip processing,a high purity cysteine-acrylamide adduct was prepared.The target adduct was synthesized by optimizing the reaction conditions,followed by reversed-phase column chromatography for separation and purification.Its structure was identified by mass spectrometry,nuclear magnetic resonance and ultraviolet spectroscopy,and the reduction mechanism was correspondingly elucidated.The cytotoxicity of adducts was evaluated with Caco-2 cell line.Furthermore,potato chips were pretreated with cysteine solutions and the reduction of acrylamide was detected by UPLC-MS.The results showed that the adduct with 95%purity could be obtained when the optimum reaction ratio of cysteine and acrylamide was 1:3 at 120℃for 3 h.Its molecular formula was C_(6)H_(9)NO_(3)S,with relative molecular weight of 192.0641 and maximum UV absorption wavelength of 196 nm.It was formed by Michael addition reaction between the sulfhydryl group of cysteine and the alkenyl group of acrylamide.Compared to acrylamide,the cytotoxicity of the adduct was significantly lower after 24 and 48 h treatment.Potato chips soaked in cysteine solutions of 3 and 5 g/L before frying obtained over 83%of acrylamide reduction rate.In addition,a certain amount of adduct was detected in such potato chips,indicating that cysteine could significantly reduce the acrylamide content in fried potato chips by forming acrylamide adduct.

关 键 词：丙烯酰胺 半胱氨酸 加合物 消减作用 细胞毒性 

分 类 号：TS201.2[轻工技术与工程—食品科学]