Action of tyrosinase on alpha and beta-arbutin: A kinetic study
The known derivatives from hydroquinone, α and β-arbutin, are used as depigmenting agents. In this work, we demonstrate that the oxy form of tyrosinase (oxytyrosinase) hydroxylates α and β-arbutin in ortho position of the phenolic hydroxyl group, giving rise to a complex formed by met-tyrosinase wit...
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| Veröffentlicht in: | PloS one 2017-05, Vol.12 (5), p.e0177330-e0177330 |
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| creator | Garcia-Jimenez, Antonio Teruel-Puche, Jose Antonio Berna, Jose Rodriguez-Lopez, José Neptuno Tudela, Jose Garcia-Canovas, Francisco |
| description | The known derivatives from hydroquinone, α and β-arbutin, are used as depigmenting agents. In this work, we demonstrate that the oxy form of tyrosinase (oxytyrosinase) hydroxylates α and β-arbutin in ortho position of the phenolic hydroxyl group, giving rise to a complex formed by met-tyrosinase with the hydroxylated α or β-arbutin. This complex could evolve in two ways: by oxidizing the originated o-diphenol to o-quinone and deoxy-tyrosinase, or by delivering the o-diphenol and met-tyrosinase to the medium, which would produce the self-activation of the system. Note that the quinones generated in both cases are unstable, so the catalysis cannot be studied quantitatively. However, if 3-methyl-2-benzothiazolinone hydrazone hydrochloride hydrate is used, the o-quinone is attacked, so that it becomes an adduct, which can be oxidized by another molecule of o-quinone, generating o-diphenol in the medium. In this way, the system reaches the steady state and originates a chromophore, which, in turn, has a high absorptivity in the visible spectrum. This reaction allowed us to characterize α and β-arbutin kinetically as substrates of tyrosinase for the first time, obtaining a Michaelis constant values of 6.5 ± 0.58 mM and 3 ± 0.19 mM, respectively. The data agree with those from docking studies that showed that the enzyme has a higher affinity for β-arbutin. Moreover, the catalytic constants obtained by the kinetic studies (catalytic constant = 4.43 ± 0.33 s-1 and 3.7 ± 0.29 s-1 for α and β-arbutin respectively) agree with our forecast based on 13 C NMR considerations. This kinetic characterization of α and β-arbutin as substrates of tyrosinase should be taken into account to explain possible adverse effects of these compounds. |
| doi_str_mv | 10.1371/journal.pone.0177330 |
| format | Article |
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H.</contributor><creatorcontrib>Garcia-Jimenez, Antonio ; Teruel-Puche, Jose Antonio ; Berna, Jose ; Rodriguez-Lopez, José Neptuno ; Tudela, Jose ; Garcia-Canovas, Francisco ; van Berkel, Willem J. H.</creatorcontrib><description>The known derivatives from hydroquinone, α and β-arbutin, are used as depigmenting agents. In this work, we demonstrate that the oxy form of tyrosinase (oxytyrosinase) hydroxylates α and β-arbutin in ortho position of the phenolic hydroxyl group, giving rise to a complex formed by met-tyrosinase with the hydroxylated α or β-arbutin. This complex could evolve in two ways: by oxidizing the originated o-diphenol to o-quinone and deoxy-tyrosinase, or by delivering the o-diphenol and met-tyrosinase to the medium, which would produce the self-activation of the system. Note that the quinones generated in both cases are unstable, so the catalysis cannot be studied quantitatively. However, if 3-methyl-2-benzothiazolinone hydrazone hydrochloride hydrate is used, the o-quinone is attacked, so that it becomes an adduct, which can be oxidized by another molecule of o-quinone, generating o-diphenol in the medium. In this way, the system reaches the steady state and originates a chromophore, which, in turn, has a high absorptivity in the visible spectrum. This reaction allowed us to characterize α and β-arbutin kinetically as substrates of tyrosinase for the first time, obtaining a Michaelis constant values of 6.5 ± 0.58 mM and 3 ± 0.19 mM, respectively. The data agree with those from docking studies that showed that the enzyme has a higher affinity for β-arbutin. Moreover, the catalytic constants obtained by the kinetic studies (catalytic constant = 4.43 ± 0.33 s-1 and 3.7 ± 0.29 s-1 for α and β-arbutin respectively) agree with our forecast based on 13 C NMR considerations. This kinetic characterization of α and β-arbutin as substrates of tyrosinase should be taken into account to explain possible adverse effects of these compounds.</description><identifier>ISSN: 1932-6203</identifier><identifier>EISSN: 1932-6203</identifier><identifier>DOI: 10.1371/journal.pone.0177330</identifier><identifier>PMID: 28493937</identifier><language>eng</language><publisher>United States: Public Library of Science</publisher><subject>Absorptivity ; Agaricales - enzymology ; Arbutin - chemistry ; Arbutin - pharmacology ; Ascorbic acid ; Benzothiazoles - pharmacology ; Biochemistry ; Biology and Life Sciences ; Biosynthesis ; Biotechnology ; Catalase ; Catalysis ; Chemical research ; Chemistry ; Chromophores ; Comparative studies ; Computer applications ; Computer programs ; Cosmetics ; Crustaceans ; Crystal structure ; Cytotoxicity ; Dihydroxyphenylalanine ; Diphenols ; Dopachrome isomerase ; Ellagic acid ; Energy charge ; Enzyme Inhibitors - pharmacology ; Enzymes ; Food ; Fungi ; Glycosides ; Hydrazones ; Hydrazones - pharmacology ; Hydrogen peroxide ; Hydrogen Peroxide - pharmacology ; Hydroquinone ; Hydroxyl groups ; Inactivation ; Inhibition ; Inhibitors ; Kinetics ; Medicine and Health Sciences ; Melanoma ; Membranes ; Molecular biology ; Molecular Docking Simulation ; Monophenol Monooxygenase - antagonists & inhibitors ; Monophenol Monooxygenase - metabolism ; NMR ; Nuclear magnetic resonance ; Nucleic acids ; Organic chemistry ; Organoleptic properties ; Oxidases ; Oxidation ; Oxygen ; Oxygen Consumption - drug effects ; Peptides ; Phenols ; Physical Sciences ; Pigmentation ; Properties ; Quinones ; Side effects ; Skin ; Skin cancer ; Structure-activity relationships (Biochemistry) ; Studies ; Substrate Specificity - drug effects ; Time Factors ; Tyrosinase ; Ultraviolet radiation ; Visible spectrum</subject><ispartof>PloS one, 2017-05, Vol.12 (5), p.e0177330-e0177330</ispartof><rights>COPYRIGHT 2017 Public Library of Science</rights><rights>2017 Garcia-Jimenez et al. This is an open access article distributed under the terms of the Creative Commons Attribution License: http://creativecommons.org/licenses/by/4.0/ (the “License”), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2017 Garcia-Jimenez et al 2017 Garcia-Jimenez et al</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c688t-48f7a5d087b21466831d0e350ada12c8c753062af4078d80520e97ece97ee9373</citedby><cites>FETCH-LOGICAL-c688t-48f7a5d087b21466831d0e350ada12c8c753062af4078d80520e97ece97ee9373</cites><orcidid>0000-0002-8869-067X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5426667/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5426667/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,2102,2928,23866,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28493937$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><contributor>van Berkel, Willem J. H.</contributor><creatorcontrib>Garcia-Jimenez, Antonio</creatorcontrib><creatorcontrib>Teruel-Puche, Jose Antonio</creatorcontrib><creatorcontrib>Berna, Jose</creatorcontrib><creatorcontrib>Rodriguez-Lopez, José Neptuno</creatorcontrib><creatorcontrib>Tudela, Jose</creatorcontrib><creatorcontrib>Garcia-Canovas, Francisco</creatorcontrib><title>Action of tyrosinase on alpha and beta-arbutin: A kinetic study</title><title>PloS one</title><addtitle>PLoS One</addtitle><description>The known derivatives from hydroquinone, α and β-arbutin, are used as depigmenting agents. In this work, we demonstrate that the oxy form of tyrosinase (oxytyrosinase) hydroxylates α and β-arbutin in ortho position of the phenolic hydroxyl group, giving rise to a complex formed by met-tyrosinase with the hydroxylated α or β-arbutin. This complex could evolve in two ways: by oxidizing the originated o-diphenol to o-quinone and deoxy-tyrosinase, or by delivering the o-diphenol and met-tyrosinase to the medium, which would produce the self-activation of the system. Note that the quinones generated in both cases are unstable, so the catalysis cannot be studied quantitatively. However, if 3-methyl-2-benzothiazolinone hydrazone hydrochloride hydrate is used, the o-quinone is attacked, so that it becomes an adduct, which can be oxidized by another molecule of o-quinone, generating o-diphenol in the medium. In this way, the system reaches the steady state and originates a chromophore, which, in turn, has a high absorptivity in the visible spectrum. This reaction allowed us to characterize α and β-arbutin kinetically as substrates of tyrosinase for the first time, obtaining a Michaelis constant values of 6.5 ± 0.58 mM and 3 ± 0.19 mM, respectively. The data agree with those from docking studies that showed that the enzyme has a higher affinity for β-arbutin. Moreover, the catalytic constants obtained by the kinetic studies (catalytic constant = 4.43 ± 0.33 s-1 and 3.7 ± 0.29 s-1 for α and β-arbutin respectively) agree with our forecast based on 13 C NMR considerations. This kinetic characterization of α and β-arbutin as substrates of tyrosinase should be taken into account to explain possible adverse effects of these compounds.</description><subject>Absorptivity</subject><subject>Agaricales - enzymology</subject><subject>Arbutin - chemistry</subject><subject>Arbutin - pharmacology</subject><subject>Ascorbic acid</subject><subject>Benzothiazoles - pharmacology</subject><subject>Biochemistry</subject><subject>Biology and Life Sciences</subject><subject>Biosynthesis</subject><subject>Biotechnology</subject><subject>Catalase</subject><subject>Catalysis</subject><subject>Chemical research</subject><subject>Chemistry</subject><subject>Chromophores</subject><subject>Comparative studies</subject><subject>Computer applications</subject><subject>Computer programs</subject><subject>Cosmetics</subject><subject>Crustaceans</subject><subject>Crystal structure</subject><subject>Cytotoxicity</subject><subject>Dihydroxyphenylalanine</subject><subject>Diphenols</subject><subject>Dopachrome isomerase</subject><subject>Ellagic acid</subject><subject>Energy charge</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Enzymes</subject><subject>Food</subject><subject>Fungi</subject><subject>Glycosides</subject><subject>Hydrazones</subject><subject>Hydrazones - pharmacology</subject><subject>Hydrogen peroxide</subject><subject>Hydrogen Peroxide - pharmacology</subject><subject>Hydroquinone</subject><subject>Hydroxyl groups</subject><subject>Inactivation</subject><subject>Inhibition</subject><subject>Inhibitors</subject><subject>Kinetics</subject><subject>Medicine and Health Sciences</subject><subject>Melanoma</subject><subject>Membranes</subject><subject>Molecular biology</subject><subject>Molecular Docking Simulation</subject><subject>Monophenol Monooxygenase - antagonists & inhibitors</subject><subject>Monophenol Monooxygenase - metabolism</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Nucleic acids</subject><subject>Organic chemistry</subject><subject>Organoleptic properties</subject><subject>Oxidases</subject><subject>Oxidation</subject><subject>Oxygen</subject><subject>Oxygen Consumption - drug effects</subject><subject>Peptides</subject><subject>Phenols</subject><subject>Physical Sciences</subject><subject>Pigmentation</subject><subject>Properties</subject><subject>Quinones</subject><subject>Side effects</subject><subject>Skin</subject><subject>Skin cancer</subject><subject>Structure-activity relationships (Biochemistry)</subject><subject>Studies</subject><subject>Substrate Specificity - drug effects</subject><subject>Time Factors</subject><subject>Tyrosinase</subject><subject>Ultraviolet radiation</subject><subject>Visible spectrum</subject><issn>1932-6203</issn><issn>1932-6203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>DOA</sourceid><recordid>eNqNkluL1DAUx4so7kW_gWhBEH2YMWmaJvVBGRYvAwsL3l7DaXo6k7GTjE26ON_edKe7TGUfpNCWk9_5n0v-SfKMkjllgr7duL6z0M53zuKcUCEYIw-SU1qybFZkhD08-j9JzrzfEMKZLIrHyUkm85KVTJwmHxY6GGdT16Rh3zlvLHhMYwDa3RpSsHVaYYAZdFUfjH2XLtJfxmIwOvWhr_dPkkcNtB6fjt_z5Menj98vvswurz4vLxaXM11IGWa5bATwmkhRZTQvCsloTZBxAjXQTEstOCNFBk1OhKwl4RnBUqAeXhgbZefJi4PurnVejbN7RWUpZJyLZpFYHojawUbtOrOFbq8cGHUTcN1KQRf7blEhpahFhVTHglxUVUV5SXiOPBavSx213o_V-mqLtUYbOmgnotMTa9Zq5a4Vz7OiKIZ2X48Cnfvdow9qa7zGtgWLrr_pu6SExz1E9OU_6P3TjdQK4gDGNi7W1YOoWuQl5SwvxaA1v4eKT41bo6NRGhPjk4Q3k4TIBPwTVtB7r5bfvv4_e_Vzyr46YtcIbVh71_aD1_wUzA-gjubzHTZ3S6ZEDT6_3YYafK5Gn8e058cXdJd0a2z2F-_A9gk</recordid><startdate>20170511</startdate><enddate>20170511</enddate><creator>Garcia-Jimenez, Antonio</creator><creator>Teruel-Puche, Jose Antonio</creator><creator>Berna, Jose</creator><creator>Rodriguez-Lopez, José Neptuno</creator><creator>Tudela, Jose</creator><creator>Garcia-Canovas, Francisco</creator><general>Public Library of Science</general><general>Public Library of Science (PLoS)</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>IOV</scope><scope>ISR</scope><scope>3V.</scope><scope>7QG</scope><scope>7QL</scope><scope>7QO</scope><scope>7RV</scope><scope>7SN</scope><scope>7SS</scope><scope>7T5</scope><scope>7TG</scope><scope>7TM</scope><scope>7U9</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>KB0</scope><scope>KL.</scope><scope>L6V</scope><scope>LK8</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>M7S</scope><scope>NAPCQ</scope><scope>P5Z</scope><scope>P62</scope><scope>P64</scope><scope>PATMY</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>RC3</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-8869-067X</orcidid></search><sort><creationdate>20170511</creationdate><title>Action of tyrosinase on alpha and beta-arbutin: A kinetic study</title><author>Garcia-Jimenez, Antonio ; Teruel-Puche, Jose Antonio ; Berna, Jose ; Rodriguez-Lopez, José Neptuno ; Tudela, Jose ; Garcia-Canovas, Francisco</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c688t-48f7a5d087b21466831d0e350ada12c8c753062af4078d80520e97ece97ee9373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Absorptivity</topic><topic>Agaricales - enzymology</topic><topic>Arbutin - chemistry</topic><topic>Arbutin - pharmacology</topic><topic>Ascorbic acid</topic><topic>Benzothiazoles - pharmacology</topic><topic>Biochemistry</topic><topic>Biology and Life Sciences</topic><topic>Biosynthesis</topic><topic>Biotechnology</topic><topic>Catalase</topic><topic>Catalysis</topic><topic>Chemical research</topic><topic>Chemistry</topic><topic>Chromophores</topic><topic>Comparative studies</topic><topic>Computer applications</topic><topic>Computer programs</topic><topic>Cosmetics</topic><topic>Crustaceans</topic><topic>Crystal structure</topic><topic>Cytotoxicity</topic><topic>Dihydroxyphenylalanine</topic><topic>Diphenols</topic><topic>Dopachrome isomerase</topic><topic>Ellagic acid</topic><topic>Energy charge</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Enzymes</topic><topic>Food</topic><topic>Fungi</topic><topic>Glycosides</topic><topic>Hydrazones</topic><topic>Hydrazones - pharmacology</topic><topic>Hydrogen peroxide</topic><topic>Hydrogen Peroxide - 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Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>PloS one</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Garcia-Jimenez, Antonio</au><au>Teruel-Puche, Jose Antonio</au><au>Berna, Jose</au><au>Rodriguez-Lopez, José Neptuno</au><au>Tudela, Jose</au><au>Garcia-Canovas, Francisco</au><au>van Berkel, Willem J. H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Action of tyrosinase on alpha and beta-arbutin: A kinetic study</atitle><jtitle>PloS one</jtitle><addtitle>PLoS One</addtitle><date>2017-05-11</date><risdate>2017</risdate><volume>12</volume><issue>5</issue><spage>e0177330</spage><epage>e0177330</epage><pages>e0177330-e0177330</pages><issn>1932-6203</issn><eissn>1932-6203</eissn><abstract>The known derivatives from hydroquinone, α and β-arbutin, are used as depigmenting agents. In this work, we demonstrate that the oxy form of tyrosinase (oxytyrosinase) hydroxylates α and β-arbutin in ortho position of the phenolic hydroxyl group, giving rise to a complex formed by met-tyrosinase with the hydroxylated α or β-arbutin. This complex could evolve in two ways: by oxidizing the originated o-diphenol to o-quinone and deoxy-tyrosinase, or by delivering the o-diphenol and met-tyrosinase to the medium, which would produce the self-activation of the system. Note that the quinones generated in both cases are unstable, so the catalysis cannot be studied quantitatively. However, if 3-methyl-2-benzothiazolinone hydrazone hydrochloride hydrate is used, the o-quinone is attacked, so that it becomes an adduct, which can be oxidized by another molecule of o-quinone, generating o-diphenol in the medium. In this way, the system reaches the steady state and originates a chromophore, which, in turn, has a high absorptivity in the visible spectrum. This reaction allowed us to characterize α and β-arbutin kinetically as substrates of tyrosinase for the first time, obtaining a Michaelis constant values of 6.5 ± 0.58 mM and 3 ± 0.19 mM, respectively. The data agree with those from docking studies that showed that the enzyme has a higher affinity for β-arbutin. Moreover, the catalytic constants obtained by the kinetic studies (catalytic constant = 4.43 ± 0.33 s-1 and 3.7 ± 0.29 s-1 for α and β-arbutin respectively) agree with our forecast based on 13 C NMR considerations. This kinetic characterization of α and β-arbutin as substrates of tyrosinase should be taken into account to explain possible adverse effects of these compounds.</abstract><cop>United States</cop><pub>Public Library of Science</pub><pmid>28493937</pmid><doi>10.1371/journal.pone.0177330</doi><tpages>e0177330</tpages><orcidid>https://orcid.org/0000-0002-8869-067X</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1932-6203 |
| ispartof | PloS one, 2017-05, Vol.12 (5), p.e0177330-e0177330 |
| issn | 1932-6203 1932-6203 |
| language | eng |
| recordid | cdi_plos_journals_1897800512 |
| source | MEDLINE; DOAJ Directory of Open Access Journals; Public Library of Science (PLoS) Journals Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Absorptivity Agaricales - enzymology Arbutin - chemistry Arbutin - pharmacology Ascorbic acid Benzothiazoles - pharmacology Biochemistry Biology and Life Sciences Biosynthesis Biotechnology Catalase Catalysis Chemical research Chemistry Chromophores Comparative studies Computer applications Computer programs Cosmetics Crustaceans Crystal structure Cytotoxicity Dihydroxyphenylalanine Diphenols Dopachrome isomerase Ellagic acid Energy charge Enzyme Inhibitors - pharmacology Enzymes Food Fungi Glycosides Hydrazones Hydrazones - pharmacology Hydrogen peroxide Hydrogen Peroxide - pharmacology Hydroquinone Hydroxyl groups Inactivation Inhibition Inhibitors Kinetics Medicine and Health Sciences Melanoma Membranes Molecular biology Molecular Docking Simulation Monophenol Monooxygenase - antagonists & inhibitors Monophenol Monooxygenase - metabolism NMR Nuclear magnetic resonance Nucleic acids Organic chemistry Organoleptic properties Oxidases Oxidation Oxygen Oxygen Consumption - drug effects Peptides Phenols Physical Sciences Pigmentation Properties Quinones Side effects Skin Skin cancer Structure-activity relationships (Biochemistry) Studies Substrate Specificity - drug effects Time Factors Tyrosinase Ultraviolet radiation Visible spectrum |
| title | Action of tyrosinase on alpha and beta-arbutin: A kinetic study |
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