Identification of p-hydroxybenzyl alcohol, tyrosol, phloretin and its derivate phloridzin as tyrosinase substrates.
In recent years, the hydroxyalkylphenols p-hydroxybenzyl alcohol and tyrosol, and the compound phloretin and its derivate phloridzin have been described as inhibitors of the enzyme tyrosinase. When the monophenolase and the diphenolase activities of tyrosinase on its physiological substrates l-dopa and/or l-tyrosine are measured in the presence of these compounds, the rate of action of the enzyme decreases. These findings led to the identification of these compounds as inhibitors. However, these molecules show an unusual behavior as inhibitors of the enzyme indeed, in this study, we demonstrate that they are not true inhibitors but alternative substrates of the enzyme.
GENZ: Grupo de Investigacion de Enzimologia, Departamento de Bioquimica y Biologia Molecular-A, Facultad de Biologia, Campus de Excelencia Internacional 'Mare Nostrum', Universidad de Murcia, E-30100, Espinardo, Murcia, Spain.
Carmen Vanessa
CV
Ortiz-Ruiz
Grupo de Quimica Organica Sintetica, Departamento de Quimica Organica, Facultad de Quimica, Campus de Excelencia Internacional 'Mare Nostrum', Universidad de Murcia, E-30100, Espinardo, Murcia, Spain.
Jose
J
Berna
GENZ: Grupo de Investigacion de Enzimologia, Departamento de Bioquimica y Biologia Molecular-A, Facultad de Biologia, Campus de Excelencia Internacional 'Mare Nostrum', Universidad de Murcia, E-30100, Espinardo, Murcia, Spain.
Maria Del Mar
Mdel M
Garcia-Molina
GENZ: Grupo de Investigacion de Enzimologia, Departamento de Bioquimica y Biologia Molecular-A, Facultad de Biologia, Campus de Excelencia Internacional 'Mare Nostrum', Universidad de Murcia, E-30100, Espinardo, Murcia, Spain.
Jose
J
Tudela
Departamento de Quimica Analitica, Facultad de Quimica, Campus de Excelencia Internacional 'Mare Nostrum', Universidad de Murcia, E-30100, Espinardo, Murcia, Spain.
Virginia
V
Tomas
GENZ: Grupo de Investigacion de Enzimologia, Departamento de Bioquimica y Biologia Molecular-A, Facultad de Biologia, Campus de Excelencia Internacional 'Mare Nostrum', Universidad de Murcia, E-30100, Espinardo, Murcia, Spain. Electronic address: canovasf@um.es.
Francisco
F
Garcia-Canovas
D001592:Benzyl Alcohols / Q000737:chemistry*; D057075:Enzyme Assays; D004791:Enzyme Inhibitors / Q000737:chemistry; D005656:Fungal Proteins / Q000037:antagonists & inhibitors / Q000737:chemistry*; D007700:Kinetics; D007980:Levodopa / Q000737:chemistry; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000737:chemistry*; D010648:Phenylacetates / Q000737:chemistry; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000737:chemistry; D010693:Phloretin / Q000737:chemistry*; D010695:Phlorhizin / Q000737:chemistry*; D013379:Substrate Specificity; D014443:Tyrosine / Q000737:chemistry
D001592:Benzyl Alcohols; D004791:Enzyme Inhibitors; D005656:Fungal Proteins; D010648:Phenylacetates; C018966:4-hydroxybenzyl alcohol; C011867:4-hydroxyphenylethanol; D014443:Tyrosine; D007980:Levodopa; D010695:Phlorhizin; D014442:Monophenol Monooxygenase; C025136:phenylacetic acid; D010626:Phenylethyl Alcohol; D010693:Phloretin
Alternative substrate; Phloretin; Phloridzin; Tyrosinase; Tyrosol; p-Hydroxybenzyl alcohol