Tyrosinase is a key enzyme in browning and melanin biosynthesis of fruit and vegetable, and tyrosinase inhibitors are of great significance in the field of fruit and vegetable preservation, skin whitening and medicine. In this study, ribavirin was first evaluated for its anti-tyrosinase activity and application in the preservation of Gong pear. The results of enzyme kinetics experiments indicated that ribavirin was an efficient [IC50 (0.3±0.05) mmol/L], reversible, and competitive type inhibitor of tyrosinase. Nonradiative energy transfer analysis and fluorescence quenching assays demonstrated that ribavirin formed ribavirin-enzyme complex with tyrosinase through one binding site, and accompanied by the change of enzyme conformation and nonradiative energy transfer. The results of molecular docking showed that ribavirin could enter the active center of tyrosinase and form hydrogen bonds with its six amino acid residues (Lys379, Gln356, Gln307, Asp312, Val313, Asn310) on the B chain. The experiment of Gong pears preservation showed that ribavirin could effectively reduce the weight-loss rate of fresh-cut pears and the browning degree of pear juice. The results provided theoretical and practical basis for the development of novel fruit and vegetable preservatives.
[1] DECKER H, TUCZEK F.Tyrosinase/catecholoxidase activity of hemocyanins:Structural basis and molecular mechanism[J].Trends in Biochemical Sciences, 2000, 25(8):392-397.
[2] SANCHEZ-FERRER A, RODRIGUEZ-LOPEZ J N, GARCIA-CANOVAS F, et al.Tyrosinase:A comprehensive review of its mechanism[J].Biochimica Et Biophysica Acta, 1995, 1247(1):1-11.
[3] HUANG X H, CHEN Q X, YOU M S, et al.Inhibitory effects of fluorobenzaldehydes on the activity of mushroom tyrosinase[J].Journal of Enzyme Inhibition and Medicinal Chemistry, 2006, 21(4):413-418.
[4] SOLOMON E I, SUNDARAM U M, MACHONKIN T E.Multicopper oxidases and oxygenases[J].Chemical Reviews, 1996, 96(7):2 563-2 606.
[5] YI W, WU X, CAO R, et al.Biological evaluations of novel vitamin C esters as mushroom tyrosinase inhibitors and antioxidants[J].Food Chemistry, 2009, 117(3):381-396.
[6] ASHIDA M, BREY P T.Role of the integument in insect defense:Pro-phenol oxidase cascade in the cuticular matrix[J].Proceedings of the National Academy of Sciences of the United States of America, 1995, 92(23):10 698-10 702.
[7] 景临林, 范小飞, 贾正平.糖基化三氮唑香草酸衍生物的合成及酪氨酸酶抑制活性研究[J].化学试剂, 2014, 36(1):9-12.
JING L L, FAN X F, JIA Z P.Synthesis and tyrosinase inhibitory activity of vanillic acid derivatives linked with glycosyltriazole[J].Chemical Reagents, 2014, 36(1):9-12.
[8] YU F, JIA Y L, WANG H F, et al.Synthesis of triazole schiff's base derivatives and their inhibitory kinetics on tyrosinase activity[J].PLoS One, 2015, 10(9).DOI:10.1371/jouynal.pone.0138578.
[9] 张鲁斌, 贾志伟, 洪克前, 等.一种用于芒果贮藏保鲜的方法:中国, CN104430827A[P].2015-03-25.
ZHANG L B, JIA Z W, HONG K Q, et al.A method for storing and keeping fresh mango:China, CN104430827A[P].2015-03-25
[10] BURROWS F S, CARLOS L M, BENZIMRA M, et al.Oral ribavirin for respiratory syncytial virus infection after lung transplantation:Efficacy and cost-efficiency[J].The Journal of Heart and Lung Transplantation:The official publication of the International Society for Heart Transplantation, 2015, 34(7):958-962.
[11] CHAI W M, HUANG Q, LIN M Z, et al.Condensed tannins from Longan Bark as inhibitor of tyrosinase:Structure, activity, and mechanism[J].Journal of Agricultural and Food Chemistry, 2018, 66(4):908-917.
[12] CHEN X X, ZHANG J, CHAI W M, et al.Reversible and competitive inhibitory kinetics of amoxicillin on mushroom tyrosinase[J].International Journal of Biological Macromolecules, 2013, 62(7):26-33.
[13] WU Z, SHEN L, HAN Q, et al.Mechanism and nature of inhibition of trypsin by ligupurpuroside A, a Ku-Ding tea extract, studied by spectroscopic and docking methods[J].Food Biophysics, 2016, 12(1):78-87.
[14] CHAI W M, LIN M Z, FENG H L, et al.Proanthocyanidins purified from fruit pericarp of Clausena lansium (Lour.) Skeels as efficient tyrosinase inhibitors:Structure evaluation, inhibitory activity and molecular mechanism[J].Food & Function, 2017, 8(3):1 043-1 051.
[15] PENG X, WANG X, QI W, et al.Deciphering the binding patterns and conformation changes upon the bovine serum albumin-rosmarinic acid complex[J].Food & Function, 2015, 6(8):2 712-2 726.
[16] LASKAR K, ALAM P, KHAN R H, et al.Synthesis, characterization and interaction studies of 1, 3, 4-oxadiazole derivatives of fatty acid with human serum albumin (HSA):A combined multi-spectroscopic and molecular docking study[J].European Journal of Medicinal Chemistry, 2016, 122(7):2-8.
[17] HUANG Q, CHAI W M, MA Z Y, et al.Antityrosinase mechanism of ellagic acid in vitro and its effect on mouse melanoma cells[J].Journal of Food Biochemistry, 2019, 43(11).DOI:10.11/jfbc.12996.
[18] LIN M Z, CHAI W M, ZHENG Y L, et al.Inhibitory kinetics and mechanism of rifampicin on alpha-glucosidase:Insights from spectroscopic and molecular docking analyses[J].International Journal of Biological Macromolecules, 2019, 122(12):44-52.
[19] LIN M Z, CHAI W M, OU-YANG C, et al.Antityrosinase mechanism of omeprazole and its application on the preservation of fresh-cut Fuji apple[J].International Journal of Biological Macromolecules, 2018, 117:538-45.
[20] 刘云芬, 廖玲燕, 段振华, 等.不同处理对鲜切莴苣褐变及贮藏品质的影响[J].保鲜与加工, 2020, 20(4):15-20.
LIU Y F, LIAO L Y, DUAN Z H, et al.Effects of different agents on browning and storage quality of fresh-cut lettuce[J].Storage and Process, 2020, 20(4):15-20.
[21] MAEDA K, FUKUDA M.Arbutin:mechanism of its depigmenting action in human melanocyte culture[J].The Journal of Pharmacology and Experimental Therapeutics, 1996, 276(2):765-769.
[22] KIM D, PARK J, KIM J, et al.Flavonoids as mushroom tyrosinase inhibitors:A fluorescence quenching study[J].Journal of Agricultural and Food Chemistry, 2006, 54(3):935-941.
[23] CHAI W M, OUYANG C, HUANG Q, et al.Antityrosinase and antioxidant properties of mung bean seed proanthocyanidins:Novel insights into the inhibitory mechanism[J].Food Chemistry, 2018, 260(2):27-36.
[24] MIAO M, JIANG B, JIANG H, et al.Interaction mechanism between green tea extract and human alpha-amylase for reducing starch digestion[J].Food Chemistry, 2015, 186(3):20-25.
[25] XIAO F, GU M, LIANG Y, et al.Spectroscopic investigation on the interaction of hyperbranched poly (amine) ester with model plasma protein:Effect on the structural and conformational changes[J].Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy, 2014, 118(1):106-112.
[26] KANDAGAL P B, SHAIKH S M T, MANJUNATHA D H, et al.Spectroscopic studies on the binding of bioactive phenothiazine compounds to human serum albumin[J].Journal of Photochemistry and Photobiology A:Chemistry, 2007, 189(1):121-127.
