Research advances in the analytical techniques and biological activities of alkylresorcinols
ZOU Yanyu1,2, FAN Fengjiao2*, FANG Yong2, LI Peng2, HUANG Qinqin2, WANG Kaituo1
1(College of Biology and Food Engineering, Chongqing Three Gorges University, Chongqing 404000, China) 2(College of Food Science and Engineering, Nanjing University of Finance and Economics, Nanjing 210023, China)
Abstract: Alkylresorcinols are special amphiphilic phenolic lipids found in wheat, rye and other grains. Alkylresorcinols are biomarkers of whole grains, which can be used as important indexes to evaluate the quality of whole grains. Alkylresorcinols have many kinds of biological activities and are getting more and more researcher′s attention. This review firstly introduced the separation and extraction methods of alkylresorcinols, and then summarized the quantitative and qualitative analysis methods and their physiological activities. Finally, the analytical and research methods of alkylresorcinols and future developments were proposed. This review provides scientific references for the green extraction of alkylresorcinols and the further study of its potential activities.
邹燕羽,樊凤娇,方勇,等. 烷基间苯二酚分析技术及其生理活性研究进展[J]. 食品与发酵工业, 2020, 46(18): 272-278.
ZOU Yanyu,FAN Fengjiao,FANG Yong,et al. Research advances in the analytical techniques and biological activities of alkylresorcinols[J]. Food and Fermentation Industries, 2020, 46(18): 272-278.
[1] KOZUBEK A, TYMAN J H P. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activity[J]. Chemical Reviews, 1999, 99(1):1-26. [2] KOZUBEK A, TYMAN J H P. Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains[J]. Chemistry and Physics of Lipids, 1995, 78(1): 29-35. [3] RIGHETTI L, CIRLINI M, FOLLONI S, et al. 5-n-alkylresorcinols but not hydroxycinnamic acids are directly related to a lower accumulation of deoxynivalenol and its glucoside in Triticum spp. genotypes with different ploidity levels[J]. Journal of Cereal Science, 2019, 85: 214-220. [4] 黎鹏. 产烷基间苯二酚的酿酒酵母工程菌株的构建及代谢改造[D]. 镇江:江苏科技大学, 2019. [5] KNODLER M, BERARDINI N, KAMMERER D R, et al. Characterization of major and minor alk(en)ylresorcinols from mango (Mangifera indica L.) peels by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry[J]. Rapid Communications in Mass Spectrometry, 2007, 21(6): 945-951. [6] CHEN Y, ROSS A B, ÅMAN P, et al. Alkylresorcinols as markers of whole grain wheat and rye in cereal products[J]. Journal of Agricultural and Food Chemistry, 2004, 52(26): 8 242-8 246. [7] 周厚德, 刘玉环, 李瑞贞, 等. 全麦中烷基间苯二酚的研究概述[J]. 食品科学, 2008, 29(8): 680-684. [8] PARIKKA K, ROWLAND I R, WELCH R W, et al. In vitro antioxidant activity and antigenotoxicity of 5-n-alkylresorcinols[J]. Journal of Agricultural and Food Chemistry, 2006, 54(5): 1 646-1 650. [9] ORIENTEA M, DIAZ-DE-CERIOB E, VERARDOB V, et al. Assessment of phytochemical compounds in functional couscous: Determination of free and bound phenols and alkylresorcinols[J]. Food Research International, 2020, 130: 108 970. [10] ROSS A B, ÅMAN P, KAMAL-ELDIN A. Identification of cereal alkylresorcinol metabolites in human urine-potential biomarkers of wholegrain wheat and rye intake[J]. Journal of Chromatography B, 2004, 809(1): 125-130. [11] LS/T 3244—2015全麦粉[S]. 北京:中国标准出版社, 2015. [12] WIERZBICKA R, WU H, FRANEK M, et al. Determination of alkylresorcinols and their metabolites in biological samples by gas chromatography-mass spectrometry[J]. Journal of Chromatography B, 2015, 1 000: 120-129. [13] SHAH I, SHAH M A, NAWAZ M A, et al. Analysis of other phenolics (capsaicin, gingerol, and alkylresorcinols)[J]. Recent Advances in Natural Products Analysis, 2020, 6: 255-271. [14] ROSS A B. Analysis of alkylresorcinols in cereal grains and products using ultrahigh-pressure liquid chromatography with fluorescence, ultraviolet, and coul array electrochemical detection[J]. Journal of Agricultural and Food Chemistry, 2012, 60(36): 8 954-8 962. [15] LANDBERG R, ANDERSSON R, ÅMAN P, et al. Comparison of GC and colorimetry for the determination of alkylresorcinol homologues in cereal grains and products[J]. Food Chemistry, 2009, 113(4): 1 363-1 369. [16] LANDBERG R, KAMAL-ELDIN A, ANDERSSON R, et al. Alkylresorcinol content and homologue composition in durum wheat (Triticum durum) kernels and pasta products[J]. Journal of Agricultural and Food Chemistry, 2006, 54(8): 3 012-3 014. [17] 彭田园, 赵仁勇, 王香玉. 超声波辅助提取全麦粉中烷基间苯二酚的工艺优化[J]. 河南工业大学学报(自然科学版), 2017, 38(4): 14-19. [18] 汤卫国, 管福琴, 赵友谊, 等. 五种小麦麸皮烷基酚类化合物体外抗肿瘤作用及初步的机制研究[J]. 食品工业科技, 2014, 35(15): 352-355. [19] 赵广河, 张瑞芬, 苏东晓, 等.全谷物酚类物质及其抗氧化活性研究进展[J]. 中国食品学报, 2017, 17(8): 183-196. [20] GENG P, HARNLY J M, CHEN P. Differentiation of bread made with whole grain and refined wheat (T. aestivum) flour using LC/MS-based chromatographic fingerprinting and chemometric approaches[J]. Journal of Food Composition and Analysis, 2016, 47: 92-100. [21] KNODLER M, KAISER A, CARLE R, et al. Profiling of alk(en)ylresorcinols in cereals by HPLC-DAD-APcI-MSn[J]. Analytical and Bioanalytical Chemistry, 2008, 391(1): 221-228. [22] 吴素仪, 丘泰球, 范晓丹. 超声波在中草药有效成分提取应用中的研究进展[J]. 江苏中医药, 2008, 40(7): 93-94. [23] 李雪萌, 姜宝杰, 张雅, 等. 超临界CO2萃取技术在食品中的应用[J]. 粮食与油脂, 2020, 33(1):18-20. [24] 赵茹.超临界流体萃取技术在天然药物提取中的应用分析[J]. 化工管理, 2019(36): 17-18. [25] GUNENC A, HADINEZHAD M, FARAH I, et al. Impact of supercritical CO2 and traditional solvent extraction systems on the extractability of alkylresorcinols, phenolic profile and their antioxidant activity in wheat bran[J]. Journal of Functional Foods, 2015, 12: 109-119. [26] KOSEOGLU K, ULUSOY H I, YILMAZ E, et al. Simple and sensitive determination of vitamin A and E in the milk and egg yolk samples by using dispersive solid phase extraction with newly synthesized polymeric material[J/OL]. Journal of Food Composition and Analysis, 2020. https://doi.org/10.1016/j.jfca.2020.103482. [27] 傅若农. 近年国内固相萃取-色谱分析的进展[J]. 分析试验室, 2007, 26(2): 100-122. [28] MARKLUND M, LANDBERG R, ÅMAN P, et al. Comparison of gas chromatography-mass spectrometry and high-performance liquid chromatography with coulometric electrode array detection for determination of alkylresorcinol metabolites in human urine[J]. Journal of Chromatography B, 2011, 879(9): 647-651. [29] 郭亚洲. 麸皮中烷基间苯二酚对HepG2细胞抗肿瘤机理研究[D]. 镇江:江苏大学, 2019. [30] PATZKE H, SCHULZE-KAYSERS N, SCHIEBER A. Separation and isolation of saturated and unsaturated 5-n-alk(en)ylresorcinols from rye bran[J]. Journal of Chromatography A, 2016, 1 438: 39-45. [31] LIANG J, HE J, ZHU S, et al. Preparation of main iridoid glycosides in fructus corni by macroporous resin column chromatography and countercurrent chromatography[J]. Journal of Liquid Chromatography & Related Technologies, 2013, 36(8): 983-999. [32] LIU J, HAO Y, WANG Z, et al. Identification, quantification, and anti-inflammatory activity of 5-n-alkylresorcinols from 21 different wheat varieties[J]. Journal of Agricultural and Food Chemistry, 2018, 66(35): 9 241-9 247. [33] WANG Z, HAO Y, WANG Y, et al. Wheat alkylresorcinols protect human retinal pigment epithelial cells against H2O2-induced oxidative damage through Akt-dependent Nrf2/HO-1 signaling[J]. Food & Function, 2019, 10(5): 2 797-2 804. [34] GAJDA A, KULAWINEK M, KOZUBEK A. An improved colorimetric method for the determination of alkylresorcinols in cereals and whole-grain cereal products[J]. Journal of Food Composition and Analysis, 2008, 21(5): 428-434. [35] SAMPIETRO D A, JIMENEZ C M, BELIZAN M M, et al. Development and validation of a micromethod for fast quantification of 5-n-alkylresorcinols in grains and whole grain products[J]. Food Chemistry, 2013, 141(4): 3 546-3 551. [36] LANDBERG R, ANDERSSON R, ÅMAN P, et al. Comparison of GC and colorimetry for the determination of alkylresorcinol homologues in cereal grains and products[J]. Food Chemistry, 2009, 113(4): 1 363-1 369. [37] ROSS A B, KAMAL-ELDIN A, JUNG C, et al. Gas chromatographic analysis of alkylresorcinols in rye (Secale cereale L) grains[J]. Journal of the Science of Food and Agriculture, 2001, 81(14): 1 405-1 411. [38] ROSS A B, SHEPHERD M J, SCHUPPHAUS M, et al. Alkylresorcinols in cereals and cereal products[J]. Journal of Agricultural and Food Chemistry, 2003, 51(14): 4 111-4 118. [39] MARKLUND M, LANDBERG R, ÅMAN P, et al. Determination of alkylresorcinol metabolites in human urine by gas chromatography-mass spectrometry[J]. Journal of Chromatography B, 2010, 878(11): 888-894. [40] MARKLUND M, LANDBERG R, ÅMAN P, et al. Comparison of gas chromatography-mass spectrometry and high-performance liquid chromatography with coulometric electrode array detection for determination of alkylresorcinol metabolites in human urine[J]. Journal of Chromatography B, 2011, 879(9): 647-651. [41] ROSS A B, SVELANDER C, KARLSSON G, et al. Identification and quantification of even and odd chained 5-n-alkylresorcinols, branched chain-alkylresorcinols and methylalkylresorcinols in Quinoa (Chenopodium quinoa)[J]. Food Chemistry, 2017, 220: 344-351. [42] FERNANDES A S, PETRY F C, MERCADANTE A Z, et al. HPLC-PDA-MS/MS as a strategy to characterize and quantify natural pigments from microalgae[J]. Current Research in Food Science, 2020, 3: 100-112. [43] ZHU J, YI X, LIU W, et al. Immobilized fusion protein affinity chromatography combined with HPLC-ESI-Q-TOF-MS/MS for rapid screening of PPARγ ligands from natural products[J]. Talanta, 2017, 165: 508-515. [44] MULLIN W J, WOLYNETZ M S, EMERY J P. A comparison of methods for the extraction and quantitation of alk(en)ylresorcinols[J]. Journal of Food Composition and Analysis, 1992, 5(3): 216-223. [45] KNODLER M, BERARDINI N, KAMMERER D R, et al. Characterization of major and minor alk(en)ylresorcinols from mango (Mangifera indica L.) peels by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry[J]. Rapid Communications in Mass Spectrometry, 2007, 21(6): 945-951. [46] ROSS A B, KOCHHAR S. Rapid and sensitive analysis of alkylresorcinols from cereal grains and products using HPLC-coularray-based electrochemical detection[J]. Journal of Agricultural and Food Chemistry, 2009, 57(12): 5 187-5 193. [47] CHEN J P, ZHU L J, SU X X, et al. New alkylresorcinols from the fruits of Embelia ribes[J]. Fitoterapia, 2018, 128: 66-72. [48] HLADYSZOWSKI J, ZUBIK L, KOZUBEK A. Quantum mechanical and experimental oxidation studies of pentadecylresorcinol, olivetol, orcinol and resorcinol[J]. Free Radical Research, 1998, 28(4): 359-368. [49] BITKOV V V, NENASHEV V A, PRIDACHINA N N, et al. Membrane-structuring properties of bacterial long-chain alkylresorcinols[J]. Biochimica et Biophysica Acta (BBA)-Biomembranes, 1992, 1 108(2): 224-232. [50] ERIN A N, DAVITASHVILI N G, PRILIPKO L L, et al. Effect of alkylresorcin on biological membranes during activation of lipid peroxidation[J]. Biokhimiia (Moscow, Russia), 1987, 52(7): 1 180-1 185. [51] ZUBIK L, HLADYSZOWSKI J, CZUCHA B, et al. The effect of resorcinolic lipids on peroxidation of liposomal phospholipids. Experimental and molecular modeling studies[C].Wroclaw:Mejbaum-Katzenellenbogen′s seminars in molecular biology, 1996:24. [52] KOZUBEK A, NIENARTOWICZ B. Cereal grain resorcinolic lipids inhibit H2O2-induced peroxidation of biological membranes[J]. Acta Biochimica Polonica, 1995, 42(3): 309-315. [53] KORYCINSKA M, CZELNA K, JAROMIN A, et al. Antioxidant activity of rye bran alkylresorcinols and extracts from whole-grain cereal products[J]. Food Chemistry, 2009, 116(4): 1 013-1 018. [54] 陈志雄, 曾爱林, 胡雅琴, 等.糖尿病前期患者焦虑现状调查及影响因素分析[J]. 中国全科医学, 2019, 22(20): 2 411-2 415. [55] ÅBERG S, MANN J, NEUMANN S, et al. Whole-grain processing and glycemic control in type 2 diabetes: A randomized crossover trial[J]. Diabetes Care, 2020, https://doi.org/10.2337/dc20-0 263. [56] 袁蒲, 孙经, 杨丽, 等. 全谷物食品对糖尿病的干预控制研究进展[J]. 糖尿病新世界, 2017, 20(14): 193-194 [57] ANDERSSON U, DEY E S, HOLM C, et al. Rye bran alkylresorcinols suppress adipocyte lipolysis and hormone-sensitive lipase activity[J]. Molecular Nutrition & Food Research, 2011, 55(2): 290-293. [58] BISKUP I, KYRO C, MARKLUND M, et al. Plasma alkylresorcinols, biomarkers of whole-grain wheat and rye intake, and risk of type 2 diabetes in Scandinavian men and women[J]. The American Journal of Clinical Nutrition, 2016, 104(1):88-96. [59] 韩梅, 陈艳, 张雨燕. 探讨我国预防控制肥胖的策略[J]. 中国医药指南, 2016, 14(10): 279-280. [60] 唐静静, 孙璐. 肥胖问题与营养标签制度研究[J]. 中国食品药品监管, 2020 (2): 90-98. [61] OISHI K, YAMAMOTO S, ITOH N, et al. Wheat alkylresorcinols suppress high-fat, high-sucrose diet-induced obesity and glucose intolerance by increasing insulin sensitivity and cholesterol excretion in male mice[J]. The Journal of Nutrition, 2015, 145(2): 199-206. [62] REJMAN J, KOZUBEK A. Inhibitory effect of natural phenolic lipids upon NAD-dependent dehydrogenases and on triglyceride accumulation in 3T3-L1 cells in culture[J]. Journal of Agricultural and Food Chemistry, 2004(52): 246-250. [63] ROSS A B, CHEN Y, FRANK J, et al. Cereal alkylresorcinols elevate gamma-tocopherol levels in rats and inhibit gamma-tocopherol metabolism in vitro[J]. The Journal of Nutrition, 2004, 134(3): 506-510. [64] TU J, CHEN J, ZHU S, et al. Inhibition of wheat bran and it′s active components on alpha-glucosidase in vitro[J]. Pharmacogn Mag, 2013,9: 309-314. [65] 杨春, 李恒, 李海, 等. 5-烷基间苯二酚诱导人结直肠癌细胞凋亡的机制探讨[J]. 世界华人消化杂志, 2017(29):2 621-2 630. [66] FU J, SOROKA D N, ZHU Y, et al. Whole grain alkylresorcinols induce apoptosis and cause cell cycle arrest in human colon cancer cells by activating p53 pathway[J]. Journal of Agricultural and Food Chemistry, 2018, 66(45): 11 935-11 942. [67] WANG L, YANG S, CAO J, et al. Microencapsulation of ginger volatile oil based on gelatin/sodium alginate polyelectrolyte complex[J]. Chemical & Pharmaceutical Bulletin, 2016, 64(1): 21-26. [68] 刘文超. 基于PC12细胞模型分析大豆蛋白酶解物对神经元氧化损伤的保护作用[D]. 长春:吉林大学, 2016. [69] 寇贝贝. 苯海索对H2O2介导的PC12细胞损伤的保护作用研究[D]. 开封:河南大学, 2018. [70] WEI Y, LIU D, ZHENG Y, et al. Neuroprotective effects of kinetin against glutamate-induced oxidative cytotoxicity in HT22 cells: Involvement of Nrf2 and heme oxygenase-1[J]. Neurotoxicity Research, 2018, 33(4): 725-737. [71] FERRERES F, GROSSO C, GIL-IZQUIERDO A, et al. Phenolic compounds from Jacaranda caroba (Vell.) A. DC.: Approaches to neurodegenerative disorders[J]. Food and Chemical Toxicology, 2013, 57: 91-98.
2020, Vol. 46 
