Spectroscopic Method Combined with Molecular Docking Technique to Study the Interaction of Limonin with Bovine Serum Albumin

LIANG Xinfu; DONG Qingliang

doi:10.13386/j.issn1002-0306.2023100285

Volume 45 Issue 21

Oct. 2024

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Science and Technology of Food Industry > 2024 > 45(21): 37-44. > DOI: 10.13386/j.issn1002-0306.2023100285

LIANG Xinfu, DONG Qingliang. Spectroscopic Method Combined with Molecular Docking Technique to Study the Interaction of Limonin with Bovine Serum Albumin[J]. Science and Technology of Food Industry, 2024, 45(21): 37−44. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2023100285.

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Spectroscopic Method Combined with Molecular Docking Technique to Study the Interaction of Limonin with Bovine Serum Albumin

LIANG Xinfu^{1, 2, 3,},
DONG Qingliang^{2, 3, ,}

1.
College of Light Industry and Food Engineering, Guangxi University, Nanning 530000, China
2.
Food Engineering College, Beibu Gulf University, Qinzhou 535000, China
3.
Guangxi College and University Key Laboratory of High-value Utilization of Seafood and Prepared Food in Beibu Gulf, Qinzhou 535000, China

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Received Date: November 02, 2023
Available Online: August 26, 2024

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Abstract

Abstract

In order to study the interaction between limonin (LM) and bovine serum albumin (BSA), in this paper, the interaction mechanism between LM and BSA was explored by ultraviolet (UV) spectroscopy, fluorescence spectroscopy and molecular docking technology. The results showed that LM could significantly quench the endogenous fluorescence of BSA, displaying a static quenching type. In addition, LM formed a binding site with BSA by hydrogen bonding and van der Waals forces, demonstrating a spontaneous interaction mechanism. Meanwhile, UV spectroscopy and synchronous fluorescence spectroscopy showed that the interaction between LM and BSA could increase the hydrophobicity of tyrosine (Tyr) and tryptophan (Trp) residue microenvironment on BSA. Through competition site experiments and molecular docking, it was found that the binding site between LM and BSA was near site Ⅰ, and LM could form hydrogen bonds with Trp-213 on BSA, and there were van der Waals forces between LM and Tyr-340/451 residues.
- limonin,
- bovine serum albumin,
- interaction,
- fluorescence spectrum,
- molecular docking

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References

[1]	晏敏, 周宇, 贺肖寒, 等. 柑橘籽中柠檬苦素及类似物的生物活性研究进展[J]. 食品与发酵工业,2018,44(2):290−296. [YAN M, ZHOU Y, HE X H, et al. Research progress on the biological activity of limonin and its analogues in citrus seeds[J]. Food and Fermentation Industry,2018,44(2):290−296.] YAN M, ZHOU Y, HE X H, et al. Research progress on the biological activity of limonin and its analogues in citrus seeds[J]. Food and Fermentation Industry, 2018, 44（2）: 290−296.
[2]	李韶静, 汤建华. 木果楝属柠檬苦素类似物及其生物活性的研究进展[J]. 中草药,2022,53(10):3178−3194. [LI S J, TANG J H. Research progress on limonin analogues of the genus Melia and their biological activities[J]. Chinese Herbal Medicine,2022,53(10):3178−3194.] doi: 10.7501/j.issn.0253-2670.2022.10.029 LI S J, TANG J H. Research progress on limonin analogues of the genus Melia and their biological activities[J]. Chinese Herbal Medicine, 2022, 53（10）: 3178−3194. doi: 10.7501/j.issn.0253-2670.2022.10.029
[3]	罗喜荣, 任荣, 钱志瑶, 等. HPLC法测定柠檬苦素的平衡溶解度和表观油水分配系数[J]. 药物分析杂志,2013,33(10):1711−1714. [LUO X R, REN R, QIAN Z Y, et al. HPLC determination of equilibrium solubility and apparent oil/water partition coefficient of limonin[J]. Chinese Journal of Pharmaceutical Analysis,2013,33(10):1711−1714.] LUO X R, REN R, QIAN Z Y, et al. HPLC determination of equilibrium solubility and apparent oil/water partition coefficient of limonin[J]. Chinese Journal of Pharmaceutical Analysis, 2013, 33（10）: 1711−1714.
[4]	吕艳芳, 梁倩倩, 郭雨晴, 等. 分子对接和光谱法研究原儿茶醛和阿魏酸与牛血清白蛋白的互作机理[J]. 食品科学,2021,42(14):24−31. [LÜ Y F, LIANG Q Q, GUO Y Q, et al. Molecular docking and spectroscopic studies on the interaction mechanism between protocatechualdehyde and ferulic acid with bovine serum albumin[J]. Food Science,2021,42(14):24−31.] doi: 10.7506/spkx1002-6630-20200618-251 LÜ Y F, LIANG Q Q, GUO Y Q, et al. Molecular docking and spectroscopic studies on the interaction mechanism between protocatechualdehyde and ferulic acid with bovine serum albumin[J]. Food Science, 2021, 42（14）: 24−31. doi: 10.7506/spkx1002-6630-20200618-251
[5]	GELAMO E L, SILVA C H T P, IMASATO H, et al. Interaction of bovine (BSA) and human (HSA) serum albumins with ionic surfactants:Spectroscopy and modelling[J]. Biochimica et Biophysica Acta,2002,1594(1):84−99. doi: 10.1016/S0167-4838(01)00287-4
[6]	MARUYAMA T, LIN C C, YAMASAKI K, et al. Binding of suprofen to human serum albumin. Role of the suprofen carboxyl group[J]. Biochem Pharmacol,1993,45(5):1017−1026. doi: 10.1016/0006-2952(93)90245-R
[7]	李琳, 婺鸣, 李冰, 等. 杂环胺与牛血清白蛋白的相互作用研究[J]. 华南理工大学学报(自然科学版),2020,48(11):123−130. [LI L, WU M, LI B, et al. Interaction studies between heterocyclic amines and bovine serum albumin[J]. Journal of South China University of Technology (Natural Science Edition),2020,48(11):123−130.] doi: 10.12141/j.issn.1000-565X.200285 LI L, WU M, LI B, et al. Interaction studies between heterocyclic amines and bovine serum albumin[J]. Journal of South China University of Technology （Natural Science Edition）, 2020, 48（11）: 123−130. doi: 10.12141/j.issn.1000-565X.200285
[8]	KUMARI M, MAURYA J K, TASLEEM M, et al. Probing HSA-ionic liquid interactions by spectroscopic and molecular docking methods[J]. Journal of Photochemistry and Photobiology B:Biology,2014,138:27−35. doi: 10.1016/j.jphotobiol.2014.05.009
[9]	ZHANG Z, YANG M, YI J, et al. Comprehensive insights into the interactions of two emerging bromophenolic DBPs with human serum albumin by multispectroscopy and molecular docking[J]. ACS Omega,2019,4(1):563−572. doi: 10.1021/acsomega.8b03116
[10]	LI T, HU P, DAI T, et al. Comparing the binding interaction between beta-lactoglobulin and flavonoids with different structure by multi-spectroscopy analysis and molecular docking[J]. Spectrochim Acta A Mol Biomol Spectrosc,2018,201:197−206. doi: 10.1016/j.saa.2018.05.011
[11]	王会镇, 赵雨, 姚小军, 等. 1-(4-甲氧基苯基)-3-(2-噻吩基)-2-丙烯酮与牛血清白蛋白的相互作用研究[J]. 化学试剂,2021,43(11):1569−1574. [WANG H Z, ZHAO Y, YAO X J, et al. Interaction of 1-(4-methoxyphenyl)-3-(2-thienyl)-2-propenone with bovine serum albumin[J]. Chemical Reagents,2021,43(11):1569−1574.] WANG H Z, ZHAO Y, YAO X J, et al. Interaction of 1-（4-methoxyphenyl）-3-（2-thienyl）-2-propenone with bovine serum albumin[J]. Chemical Reagents, 2021, 43（11）: 1569−1574.
[12]	吴明火, 李尚春, 王丽梅, 等. 邻苯二甲酸二环己酯与牛血清白蛋白相互作用研究[J]. 分析科学学报,2022,38(3):321−326. [WU M H, LI S C, WANG L M, et al. Study on the interaction between dicyclohexyl phthalate and bovine serum albumin[J]. Journal of Analytical Science,2022,38(3):321−326.] WU M H, LI S C, WANG L M, et al. Study on the interaction between dicyclohexyl phthalate and bovine serum albumin[J]. Journal of Analytical Science, 2022, 38（3）: 321−326.
[13]	RAHMAN N, KHALIL N. Characterization of sulfasalazine-bovine serum albumin and human serum albumin interaction by spectroscopic and theoretical approach[J]. Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2023,300:122865. doi: 10.1016/j.saa.2023.122865
[14]	ABUBAKAR M, KANDANDAPANI S, MOHAMED S B, et al. Shedding light on the molecular interaction between the Hepatitis B virus inhibitor, clevudine, and human serum albumin:Thermodynamic, spectroscopic, microscopic, and in silico analyses[J]. Journal of Molecular Liquids,2022,368:120737. doi: 10.1016/j.molliq.2022.120737
[15]	吕艳芳, 张紫卿, 梁倩倩, 等. 光谱法和分子对接研究高儿茶酚与牛血清白蛋白的相互作用[J]. 中国食品学报,2022,22(12):72−81. [LÜ Y F, ZHANG Z Q, LIANG Q Q, et al. Spectroscopy and molecular docking to study the interaction of catechols with bovine serum albumin[J]. Journal of Chinese Institute of Food Science and Technology,2022,22(12):72−81.] LÜ Y F, ZHANG Z Q, LIANG Q Q, et al. Spectroscopy and molecular docking to study the interaction of catechols with bovine serum albumin[J]. Journal of Chinese Institute of Food Science and Technology, 2022, 22（12）: 72−81.
[16]	HU Y, LIU Y, ZHAO R, et al. Spectroscopic studies on the interaction between methylene blue and bovine serum albumin[J]. Journal of Photochemistry and Photobiology A:Chemistry,2006,179(3):324−329. doi: 10.1016/j.jphotochem.2005.08.037
[17]	POLET H, STEINHARDT J. Binding-induced alterations in ultraviolet absorption of native serum albumin[J]. Biochemistry (Easton),1968,7(4):1348−1356. doi: 10.1021/bi00844a015
[18]	李阳, 安琪, 宋悦, 等. HPLC法测定不同产地柑橘第一次生理落果中活性成分的含量[J]. 食品工业科技,2022,43(19):364−371. [LI Y, AN Q, SONG Y, et al. HPLC was used to determine the content of active ingredients in the first physiological fruit drop of citrus from different origins[J]. Science and Technology of Food Industry,2022,43(19):364−371.] LI Y, AN Q, SONG Y, et al. HPLC was used to determine the content of active ingredients in the first physiological fruit drop of citrus from different origins[J]. Science and Technology of Food Industry, 2022, 43（19）: 364−371.
[19]	孟鹏, 郑宝东. 超高效液相色谱法快速并同时检测金柑中柠檬苦素和诺米林[J]. 中国食品学报,2013,13(2):177−181. [MENG P, ZHENG B D. Ultra-performance liquid chromatography (UPLC) was used for the rapid and simultaneous detection of limonin and nomiline in kumquats[J]. Journal of Chinese Institute of Food Science and Technology,2013,13(2):177−181.] MENG P, ZHENG B D. Ultra-performance liquid chromatography （UPLC） was used for the rapid and simultaneous detection of limonin and nomiline in kumquats[J]. Journal of Chinese Institute of Food Science and Technology, 2013, 13（2）: 177−181.
[20]	顾佳丽, 王思宇, 杨丹, 等. 光谱法研究甲苯达唑与牛血清白蛋白的相互作用[J]. 分析科学学报,2020,36(6):857−862. [GU J L, WANG S Y, YANG D, et al. The interaction between mebendazole and bovine serum albumin was studied by spectroscopy[J]. Journal of Analytical Science,2020,36(6):857−862.] GU J L, WANG S Y, YANG D, et al. The interaction between mebendazole and bovine serum albumin was studied by spectroscopy[J]. Journal of Analytical Science, 2020, 36（6）: 857−862.
[21]	LIU B, XUE C, WANG J, et al. Study on the competitive reaction between bovine serum albumin and neomycin with ponceau S as fluorescence probe[J]. Journal of Luminescence,2010,130(11):1999−2003. doi: 10.1016/j.jlumin.2010.05.017
[22]	GU J, LIU H, HUANG X, et al. Investigation of the separate and simultaneous bindings of warfarin and fenofibrate to bovine serum albumin[J]. International Journal of Biological Macromolecules,2023,236:123978. doi: 10.1016/j.ijbiomac.2023.123978
[23]	焦安妮, 于敏, 关玥, 等. 大叶冬青皂苷与牛血清蛋白的相互作用研究[J]. 食品工业科技,2021,42(19):8−14. [JIAO A N, YU M, GUANG Y, et al. Study on the interaction between saponins from Ilex magnolia and bovine serum proteins[J]. Science and Technology of Food Industry,2021,42(19):8−14.] JIAO A N, YU M, GUANG Y, et al. Study on the interaction between saponins from Ilex magnolia and bovine serum proteins[J]. Science and Technology of Food Industry, 2021, 42（19）: 8−14.
[24]	胡夏恬, 倪帅帅, 焦安妮, 等. 苦丁皂苷L、苦丁皂苷N与牛血清白蛋白的相互作用研究[J]. 食品工业科技,2020,41(9):55−60. [HU X T, NI S S, JIAO A N, et al. Study on the interaction between kudingsaponin L, kudingsaponin N and bovine serum albumin[J]. Science and Technology of Food Industry,2020,41(9):55−60.] HU X T, NI S S, JIAO A N, et al. Study on the interaction between kudingsaponin L, kudingsaponin N and bovine serum albumin[J]. Science and Technology of Food Industry, 2020, 41（9）: 55−60.
[25]	韩忠保, 吴雨杭, 米媛媛, 等. 荧光光谱法结合分子对接研究人血清白蛋白对齐墩果酸与熊果酸的异构体识别作用[J]. 光谱学与光谱分析,2019,39(7):2190−2195. [HAN Z B, WU Y H, MI Y Y, et al. Fluorescence spectroscopy combined with molecular docking study on the recognition of isomers of oleanolic acid and ursolic acid by human serum albumin[J]. Spectroscopy and Spectral Analysis,2019,39(7):2190−2195.] HAN Z B, WU Y H, MI Y Y, et al. Fluorescence spectroscopy combined with molecular docking study on the recognition of isomers of oleanolic acid and ursolic acid by human serum albumin[J]. Spectroscopy and Spectral Analysis, 2019, 39（7）: 2190−2195.
[26]	WARE W R. Oxygen quenching of fluorescence in solution:An experimental study of the diffusion process[J]. Journal of Physical Chemistry (1952),1962,66(3):455−458. doi: 10.1021/j100809a020
[27]	杨雯雁, 马秀兰, 张宇. 荧光光谱法结合分子对接研究邻苯二甲酸单环己酯与牛血清白蛋白的相互作用[J]. 分析试验室,2023,42(9):1236−1241. [YANG Y W, MA X L, ZHANG Y. Fluorescence spectroscopy combined with molecular docking study on the interaction between monocyclohexyl phthalate and bovine serum albumin[J]. Analysis Laboratory,2023,42(9):1236−1241.] YANG Y W, MA X L, ZHANG Y. Fluorescence spectroscopy combined with molecular docking study on the interaction between monocyclohexyl phthalate and bovine serum albumin[J]. Analysis Laboratory, 2023, 42（9）: 1236−1241.
[28]	HU Y, OUYANG Y, DAI C, et al. Site-selective binding of human serum albumin by palmatine:Spectroscopic approach[J]. Biomacromolecules,2010,11(1):106−112. doi: 10.1021/bm900961e
[29]	ROSS P D, SUBRAMANIAN S. Thermodynamics of protein association reactions:Forces contributing to stability[J]. Biochemistry,1981,20(11):3096−3102. doi: 10.1021/bi00514a017
[30]	AZIMI O, EMAMI Z, SALARI H, et al. Probing the interaction of human serum albumin with norfloxacin in the presence of high-frequency electromagnetic fields:Fluorescence spectroscopy and circular dichroism investigations[J]. Molecules,2011,16(12):9792−9818. doi: 10.3390/molecules16129792
[31]	赵旭红, 夏彩芬, 周紫薇, 等. 花青素对牛血清白蛋白的光谱特性及构象的影响[J]. 食品工业科技,2021,42(7):57−62. [ZHAO X H, XIA C F, ZHOU Z W, et al. Effect of anthocyanins on the spectral characteristics and conformation of bovine serum albumin[J]. Science and Technology of Food Industry,2021,42(7):57−62.] ZHAO X H, XIA C F, ZHOU Z W, et al. Effect of anthocyanins on the spectral characteristics and conformation of bovine serum albumin[J]. Science and Technology of Food Industry, 2021, 42（7）: 57−62.
[32]	刘晓娟, 邓培渊, 范春丽, 等. 环氧虫啶与人血清白蛋白的相互作用[J]. 农药学学报,2024,26(1):160−167. [LIU X J, DENG P Y, FAN C L, et al. Studies of the interaction between cycloxaprid and human serum albumin[J]. Chinese Journal of Pesticide Science,2024,26(1):160−167.] LIU X J, DENG P Y, FAN C L, et al. Studies of the interaction between cycloxaprid and human serum albumin[J]. Chinese Journal of Pesticide Science, 2024, 26（1）: 160−167.
[33]	WANG T, WANG N, YU Y, et al. Study of soybean protein isolate-tannic acid non-covalent complexes by multi-spectroscopic analysis, molecular docking, and interfacial adsorption kinetics[J]. Food Hydrocolloids,2023,137:108330. doi: 10.1016/j.foodhyd.2022.108330
[34]	HU Y, XU S, ZHU X, et al. Study on the interaction between methyl violet and bovine serum albumin by spectral analyses[J]. Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2009,74(2):526−531. doi: 10.1016/j.saa.2009.06.054

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Science and Technology of Food Industry

Spectroscopic Method Combined with Molecular Docking Technique to Study the Interaction of Limonin with Bovine Serum Albumin

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