Acrolein (ACR) is classified as a Group 3 carcinogen by International Agency for Research on Cancer, part of the World Health Organization. To study the inhibitory activity and mechanism of alpinetin (ALP) and cardamonin (CAR) on acrolein (ACR) produced in food thermal processing, we first established a new liquid chromatography mass spectrometry method to determine ALP and CAR synchronously, and screened out that Alpinia katsumadai Hayata had the highest content of ALP and CAR in six kinds of cardamom spices. Then, we added A. katsumadai into meat floss and analyzed the inhibitory activity and mechanism of A. katsumadai on trapping ACR by using ultra-high performance liquid chromatography-electrospray secondary mass spectrometry (UPLC-ESI-MS/MS). The results showed that among the six spices, the content of ALP and CAR in A. katsumadai was the highest, reaching 3.30 and 5.53 mg/g, respectively. When the supplemental level of A. katsumadai into meat floss was up to 6%, the inhibition rate of ACR reached 47.87%. Meanwhile, ALP-ACR and CAR-ACR, the adducts of ACR conjugated with ALP/CAR, were also detected by using UPLC-MS/MS. It was demonstrated that ALP and CAR in A. katsumadai could inhibit ACR produced in high-temperature food processing by forming ACR adducts, thereby reducing the amount of ACR ingested by humans. This study has important practical significance and application value for effectively improving food safety production.
[1] QIU J Y, WU H Y, FENG F, et al.Metabolic profiling of alpinetin in rat plasma, urine, bile and feces after intragastric administration[J].Molecules (Basel, Switzerland), 2019, 24(19):3458.
[2] ZHANG T, GUO S, ZHU X Y, et al.Alpinetin inhibits breast cancer growth by ROS/NF-κB/HIF-1α axis[J].Journal of Cellular and Molecular Medicine, 2020, 24(15):8 430-8 440.
[3] WANG C L, XIA Y, QU L H, et al.Cardamonin inhibits osteogenic differentiation of human valve interstitial cells and ameliorates aortic valve calcification via interfering in the NF-κB/NLRP3 inflammasome pathway[J].Food & Function, 2021, 12(23):11 808-11 818.
[4] STEVENS J F, MAIER C S.Acrolein:Sources, metabolism, and biomolecular interactions relevant to human health and disease[J].Molecular Nutrition & Food Research, 2008, 52(1):7-25.
[5] LEDAUPHIN J, LE MILBEAU C, BARILLIER D, et al.Differences in the volatile compositions of French labeled brandies (Armagnac, Calvados, Cognac, and Mirabelle) using GC-MS and PLS-DA[J].Journal of Agricultural & Food Chemistry, 2010, 58(13):7 782-7 793.
[6] WANG J Q, LU Y L, ZHENG T S, et al.Scavenging of acrolein by food-grade antioxidant propyl gallate in a model reaction system and cakes[J].Journal of Agricultural and Food Chemistry, 2019, 67(31):8 520-8 526.
[7] ZIRAK M R, MEHRI S, KARIMANI A, et al.Mechanisms behind the atherothrombotic effects of acrolein, a review[J].Food and Chemical Toxicology, 2019, 129:38-53.
[8] LEE C H, CHEN K T, LIN J A, et al.Recent advances in processing technology to reduce 5-hydroxymethylfurfural in foods[J].Trends in Food Science & Technology, 2019, 93:271-280.
[9] FERREIRA D C, NICOLLI K P, SOUZA-SILVA É A, et al.Carbonyl compounds in different stages of vinification and exposure risk assessment through Merlot wine consumption[J].Food Additives & Contaminants:Part A, 2018, 35(12):2 315-2 331.
[10] GUTH S, HABERMEYER M, BAUM M, et al.Thermally induced process-related contaminants:The example of acrolein and the comparison with acrylamide[J].Molecular Nutrition & Food Research, 2013, 57(12):2 269-2 282.
[11] CAI J, BHATNAGAR A, PIERCE W M J R.Protein modification by acrolein:Formation and stability of cysteine adducts[J].Chemical Research in Toxicology, 2009, 22(4):708-716.
[12] LOPACHIN R M, GAVIN T, PETERSEN D R, et al.Molecular mechanisms of 4-hydroxy-2-nonenal and acrolein toxicity:Nucleophilic targets and adduct formation[J].Chemical Research in Toxicology, 2009, 22(9):1 499-1 508.
[13] GREK C L, TEW K D.Redox metabolism and malignancy[J].Current Opinion in Pharmacology, 2010, 10(4):362-368.
[14] 朱梦旭. 白酒中易挥发的有毒有害小分子醛及其结合态化合物研究[D].无锡:江南大学, 2016.
ZHU M X.Volatile, toxic and small molecular aldehydes and their derivatives in Chinese liquor[D].Wuxi:Jiangnan University, 2016.
[15] ZAMORA R, AGUILAR I, GRANVOGL M, et al.Toxicologically relevant aldehydes produced during the frying process are trapped by food phenolics[J].Journal of Agricultural and Food Chemistry, 2016, 64(27):5 583-5 589.
[16] WANG W X, QI Y J, ROCCA J R, et al.Scavenging of toxic acrolein by resveratrol and hesperetin and identification of adducts[J].Journal of Agricultural and Food Chemistry, 2015, 63(43):9 488-9 495.
[17] HUANG Q J, ZHU Y D, LV L S, et al.Translating in vitro acrolein-trapping capacities of tea polyphenol and soy genistein to in vivo situation is mediated by the bioavailability and biotransformation of individual polyphenols[J].Molecular Nutrition & Food Research, 2020, 64(1):e1900274.
[18] LU Y, LIU J, TONG A Q, et al.Interconversion and acrolein-trapping capacity of cardamonin/alpinetin and their metabolites in vitro and in vivo[J].Journal of Agricultural and Food Chemistry, 2021, 69(40):11 926-11 936.
[19] GOSETTI F, CHIUMINATTO U, MAZZUCCO E, et al.Simultaneous determination of thirteen polycyclic aromatic hydrocarbons and twelve aldehydes in cooked food by an automated on-line solid phase extraction ultra high performance liquid chromatography tandem mass spectrometry[J].Journal of Chromatography A, 2011, 1 218(37):6 308-6 318.
[20] 刘孟健. 香辛料风味成分及微生物群落对烧鸡食用品质的影响[D].郑州:河南工业大学, 2014.
LIU M J.The effects of spice on flavor and quality in carbonado chicken[D].Zhengzhou:Henan University of Technology, 2014.
[21] JIANG X Y, LV H F, LU Y, et al.Trapping of acrolein by curcumin and the synergistic inhibition effect of curcumin combined with quercetin[J].Journal of Agricultural and Food Chemistry, 2021, 69(1):294-301.
[22] 张静, 祁兴普, 姚芳, 等.基于美拉德反应制备香酥肉松的研究[J].肉类工业, 2018(5):29-32.
ZHANG J, QI X P, YAO F, et al.Study on crisp fried dried meat floss prepared by Maillard reaction[J].Meat Industry, 2018(5):29-32.
[23] 邓锐, 邹毓兰, 吕海涛.微波辅助提取草豆蔻中山姜素和小豆蔻明工艺研究[J].食品工业, 2015, 36(10):184-186.
DENG R, ZOU Y L, LYU H T.Study on microwave extraction technique for alpinetin and cardamonin in Alpinia katsumadai Hayata[J].The Food Industry, 2015, 36(10):184-186.
[24] 邹毓兰, 吕海涛.草豆蔻中山姜素和小豆蔻明的HPLC测定及提取工艺优化[J].中成药, 2011, 33(1):145-148.
ZOU Y L, LYU H T.Determination of alpinetin and cardamonin in Alpinia katsumadai Hayata by HPLC and optimization of extraction technology[J].Chinese Traditional Patent Medicine, 2011, 33(1):145-148.
[25] ZHANG D M, JIANG X Y, XIAO L B, et al.Mechanistic studies of inhibition on acrolein by myricetin[J].Food Chemistry, 2020, 323:126788.
