Ligand fishing based on tubular microchannel modified with monoamine oxidase B for screening of the enzyme's inhibitors from Crocus sativus and Edgeworthia gardneri.

bioactive compounds ligand fishing modified microchannel monoamine oxidase B screening

Journal

Journal of separation science
ISSN: 1615-9314
Titre abrégé: J Sep Sci
Pays: Germany
ID NLM: 101088554

Informations de publication

Date de publication:
Jul 2022
Historique:
revised: 24 03 2022
received: 20 01 2022
accepted: 17 04 2022
pubmed: 24 4 2022
medline: 30 7 2022
entrez: 23 4 2022
Statut: ppublish

Résumé

A novel strategy of performing ligand fishing with enzyme-modified open tubular microchannel was proposed for screening bioactive components present in medicinal plants. Monoamine oxidase B was immobilized onto the surface of the microchannel for the first time to specifically extract its ligands when the plant's extracts solution flows through the channel. The thermal and the storage stability of immobilized monoamine oxidase B were significantly enhanced after immobilization. Crocin I and Ⅱ were extracted from Crocus sativus, and tiliroside was extracted from Edgeworthia gardneri. All the three compounds were inhibitors of the enzyme with the half-maximal inhibitory concentration values of 26.70 ± 0.91, 19.88 ± 2.78, and 15.65 ± 0.85 μM, respectively. The enzyme inhibition kinetics and molecular docking were investigated. This is the first report on the inhibitory effects of tiliroside and crocin Ⅱ. The novel ligand fishing method proposed in this work possesses advantages of rapidness, high efficiency, and tiny sample consumption compared to routine ligand fishing, with promising potential for screening active natural products in complex mixtures.

Identifiants

pubmed: 35461190
doi: 10.1002/jssc.202200057
doi:

Substances chimiques

Ligands 0
Monoamine Oxidase EC 1.4.3.4
Plant Extracts 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

2394-2405

Subventions

Organisme : Chinese Academy of Sciences
ID : KFJ-BRP-008
Organisme : the US National Institutes of Health
ID : 1U54MD015929

Informations de copyright

© 2022 Wiley-VCH GmbH.

Références

Atanasov AG, Waltenberger B, Pferschy-Wenzig EM, Linder T, Wawrosch C, Uhrin P, Temml GV, Wang L, Schwaiger S, Heiss EH, Rollinger JM, Schuster D, Breuss GJM, Bochov V, Mihovilovic MD, Kopp B, Bauer R, Dirsch VM, Stuppner H. Discovery and resupply of pharmacologically active plant-derived natural products: a review. Biotechnol Adv. 2015;33:1582-614.
Liu YB, Kakani R, Nair MG. Compounds in functional food fenugreek spice exhibit anti-inflammatory and antioxidant activities. Food Chem. 2012;131:1187-92.
Neelam K, Dey S, Sim R, Lee J, Eong KGA. Fructus lycii: A natural dietary supplement for amelioration of retinal diseases. Nutrients 2021;13:246.
Roy MC, Anguenot R, Fillion C, Beaulieu M, Berube J, Richard D. Effect of a commercially-available algal phlorotannins extract on digestive enzymes and carbohydrate absorption in vivo. Food Res Int. 2011;44:3026-9.
Kotwal P, Dogra A, Sharma A, Bhatt S, Gour A, Sharma S, Wazir P, Singh PP, Kumar A, Nandi U. Effect of natural phenolics on pharmacokinetic modulation of bedaquiline in rat to assess the likelihood of potential food-drug interaction. J Agric Food Chem. 2020;68:1257-65.
Bhandari MR, Jong-Anurakkun N, Hong G, Kawabata J. Alpha-glucosidase and alpha-amylase inhibitory activities of Nepalese medicinal herb Pakhanbhed (Bergenia ciliata Haw.). Food Chem. 2008;106:247-52.
Potterat O, Hamburger M. Concepts and technologies for tracking bioactive compounds in natural product extracts: generation of libraries, and hyphenation of analytical processes with bioassays. Nat Prod Rep. 2013;30:546-64.
De Boer AR, Bruyneel B, Krabbe JG, Lingeman H, Niessen WMA, Irth H. A microfluidic-based enzymatic assay for bioactivity screening combined with capillary liquid chromatography and mass spectrometry. Lab Chip. 2005;5:1286-92.
Haginaka J. Selectivity of affinity media in solid-phase extraction of analytes. Trac-Trends Anal Chem. 2005;24:407-15.
Pero-Gascon R, Gimenez E, Sanz-Nebot V, Benavente F. Enrichment of histidine containing peptides by on-line immobilised metal affinity solid-phase extraction capillary electrophoresis-mass spectrometry. Microchem J. 2020;157:105013.
Liu DM, Dong C. Recent advances in nano-carrier immobilized enzymes and their applications. Process Biochem. 2020;92:464-75.
Ansari SA, Husain Q. Potential applications of enzymes immobilized on/in nano materials: a review. Biotechnol Adv. 2012;30:512-23.
Yuan YC, Bai XL, Liu YM, Tang XY, Yuan H, Liao X. Ligand fishing based on cell surface display of enzymes for inhibitor screening. Anal Chim Acta. 2021;1156:338359.
Seger C, Sturm S, Stuppner H. Mass spectrometry and NMR spectroscopy: modern high-end detectors for high resolution separation techniques - state of the art in natural product HPLC-MS, HPLC-NMR, and CE-MS hyphenations. Nat Prod Rep. 2013;30:970-87.
Queiroz LHK, Queiroz DPK, Dhooghe L, Ferreira AG, Giraudeau P. Real-time separation of natural products by ultrafast 2D NMR coupled to on-line HPLC. Analyst 2012;137:2357-61.
Garcia E, Hasenbank MS, Finlayson B, Yager P. High-throughput screening of enzyme inhibition using an inhibitor gradient generated in a microchannel. Lab Chip. 2007;7:249-55.
Li L, Fan ML, Li YN, Huang YX, Liu XF, Liu JH. A rapid strategy for screening high-efficiency PCSK9 inhibitors from Ginkgo biloba leaves by ligand fishing, HPLC-Q-TOF-MS and interdisciplinary assay. J Food Drug Anal. 2020;28:79-88.
He Z, Zhang Q, Wang H, Li Y. Continuous high-throughput phosphopeptide enrichment using microfluidic channels modified with aligned ZnO/TiO(2) nanorod arrays. Biomed Microdevices. 2011;13:865-75.
Phillips JA, Xu Y, Xia Z, Fan ZH, Tan WH. Enrichment of cancer cells using aptamers immobilized on a microfluidic channel. Anal Chem. 2009;81:1033-9.
Kawai Y, Idegami K, Sueyoshi K, Endo T, Hisamoto H. Single-step trypsin inhibitor assay on a microchannel array device immobilizing enzymes and fluorescent substrates by inkjet printing. Anal Sci. 2021;37:1473-6.
Tripathi RKP, Ayyannan SR. Monoamine oxidase-B inhibitors as potential neurotherapeutic agents: an overview and update. Med Res Rev. 2019;39:1603-706.
Meiser J, Weindl D, Hiller K. Complexity of dopamine metabolism. Cell Commun Signal. 2013;11:34.
Caccia C, Maj R, Calabresi M, Maestroni S, Faravelli L, Curatolo L, Salvati P, Fariello R. Safinamide-from molecular targets to a new anti-Parkinson drug. Neurology 2006;67:S18-23.
Wang X, Liang XB, Li FQ, Zhou HF, Liu XY, Wang JJ, Wang XM. Therapeutic strategies for Parkinson's disease: the ancient meets the future - traditional Chinese herbal medicine, electroacupuncture, gene therapy and stem cells. Neurochem Res. 2008;33:1956-63.
Linardaki ZI, Orkoula MG, Kokkosis AG, Lamari FN, Margarity M. Investigation of the neuroprotective action of saffron (Crocus sativus L.) in aluminum-exposed adult mice through behavioral and neurobiochemical assessment. Food Chem Toxicol. 2013;52:163-70.
Mykhailenko O, Ivanauskas L, Bezruk I, Marksa M, Borodina O, Georgiyants V. Effective and simple approach for colchicine determination in saffron parts. Food Chem. 2022;368:130862.
Hosseinzadeh H, Nassiri-Asl M. Avicenna's (Ibn Sina) the canon of medicine and saffron (Crocus sativus): a review. Phytother Res. 2013;27:475-83.
Zhang Y, Yan LS, Ding Y, Cheng BCY, Luo G, Kong J, Liu GTH, Zhang SF. Edgeworthia gardneri (Wall.) Meisn. Water extract ameliorates palmitate induced insulin resistance by regulating IRS1/GSK3β/FoxO1 signaling pathway in human HepG2 hepatocytes. Fron Pharmacol. 2020;10:1666.
Ma YY, Zhao DG, Zhou AY, Zhang Y, Du ZY, Zhang K. Alpha-glucosidase inhibition and antihyperglycemic activity of phenolics from the flowers of Edgeworthia gardneri. J Agric Food Chem. 2015;63:8162-9.
Wu GF, Jiang XL, Gong YZ, Hu YD, Bai XL, Liao X. Ligand fishing of anti-neurodegenerative components from Lonicera japonica using magnetic nanoparticles immobilised with monoamine oxidase B. J Sep Sci. 2019;42:1289-98.
Huang GL, Zhu F, Chen YH, Chen SQ, Liu ZH, Li X, Gan L, Zhang GL, Yu Y. A spectrophotometric assay for monoamine oxidase activity with 2,4-dinitrophenylhydrazine as a derivatized reagent. Anal Biochem. 2016;512:18-25.
Mostert S, Petzer A, Petzer JP. Indanones as high-potency reversible inhibitors of monoamine oxidase. ChemMedChem. 2015;10:862-73.
Liang Y, Liang B, Chen W, Wu XR, Liu-Huo WS, Zhao LZ. Potential mechanism of dingji fumai decoction against atrial fibrillation based on network pharmacology, molecular docking, and experimental verification integration strategy. Front Cardiovasc Med. 2021;8:712398.
Lee H, Rho J, Messersmith PB. Facile conjugation of biomolecules onto surfaces via mussel adhesive protein inspired coatings. Adv Mater. 2009;21:431-4.
Zhang L, Guo XF, Song YY, Tang N, Cheng PG, Xiang J, Du W. Bioadhesive immobilize agarase on magnetic ferriferous by polydopamine. Mater Sci Eng C-Mater Biol Appl. 2018;93:218-25.
Bernklau I, Neusser C, Moroni AV, Gysler C, Spagnolello A, Chung W, Jekle M, Becker T. Structural, textural and sensory impact of sodium reduction on long fermented pizza. Food Chem. 2017;234:398-407.
Yushkova ED, Nazarova EA, Matyuhina AV, Noskova AO, Shavronskaya DO, Vinogradov VV, Skvortsova N, Krivoshapkina EF. Application of immobilized enzymes in food industry. J Agric Food Chem. 2019;67:11553-67.
Rodrigues RC, Ortiz C, Berenguer-Murcia A, Torres R, Fernandez-Lafuente R. Modifying enzyme activity and selectivity by immobilization. Chem Soc Rev. 2013;42:6290-307.
Zhou LY, Jiang YJ, Ma L, He Y, Gao J. Immobilization of glucose oxidase on polydopamine-functionalized graphene oxide. Appl Biochem Biotechnol. 2015;175:1007-17.
Magsumov T, Li ZY, Sedov I. Comparative study of the protein denaturing ability of different organic cosolvents. Int J Biol Macromol. 2020;160:880-8.
Pieczykolan A, Pietrzak W, Nowak R, Pielczyk J, Lamacz K. Optimization of extraction conditions for determination of Tiliroside in Tilia L. flowers using an LC-ESI-MS/MS method. J Anal Methods Chem. 2019;2019:9052425.
Zhao LL, Ciallella HL, Aleksunes LM, Zhu H. Advancing computer-aided drug discovery (CADD) by big data and data-driven machine learning modeling. Drug Discov Today. 2020;25:1624-38.
Wei N, Zhao J, Wu GM, Cao WJ, Luo P, Zhang ZF, Chen G, Wen L. Rapid screening and identification of antitumor ingredients from the mangrove endophytic fungus using an enzyme-immobilized magnetic nanoparticulate system. Molecules 2021;26:2255.
Zhang SS, Wu DD, Li H, Zhu JH, Hu WP, Lu MH, Liu X. Rapid identification of alpha-glucosidase inhibitors from Dioscorea opposita Thunb peel extract by enzyme functionalized Fe3O4 magnetic nanoparticles coupled with HPLC-MS/MS. Food Funct. 2017;8:3219-27.
Liu J, Zhang HX, Shi YP. Lipase immobilization on magnetic cellulose microspheres for rapid screening inhibitors from traditional herbal medicines. Talanta 2021;231:122374.
Chen XL, Xue S, Lin YL, Luo JG, Kong LY. Immobilization of porcine pancreatic lipase onto a metal-organic framework, PPL@MOF: A new platform for efficient ligand discovery from natural herbs. Anal Chim Acta. 2020;1099:94-102.

Auteurs

Xu-Wei Qi (XW)

Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China.
University of Chinese Academy of Sciences, Beijing, P. R. China.

Yi-Ming Liu (YM)

Department of Chemistry and Biochemistry, Jackson State University, Jackson, Mississippi, USA.

Yi-Kao Hu (YK)

Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China.
University of Chinese Academy of Sciences, Beijing, P. R. China.

Hao Yuan (H)

Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China.
University of Chinese Academy of Sciences, Beijing, P. R. China.

Emmanuel Ayodeji Ayeni (EA)

Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China.
University of Chinese Academy of Sciences, Beijing, P. R. China.

Xun Liao (X)

Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China.

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