Glabrene and Isoliquiritigenin as Tyrosinase Inhibitors from Licorice Roots
Tyrosinase is known to be a key enzyme in melanin biosynthesis, involved in determining the color of mammalian skin and hair. Various dermatological disorders, such as melasama, age spots, and sites of actinic damage, arise from the accumulation of an excessive level of epidermal pigmentation. The i...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2003-02, Vol.51 (5), p.1201-1207 |
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| creator | Nerya, Ohad Vaya, Jacob Musa, Ramadan Izrael, Sarit Ben-Arie, Ruth Tamir, Snait |
| description | Tyrosinase is known to be a key enzyme in melanin biosynthesis, involved in determining the color of mammalian skin and hair. Various dermatological disorders, such as melasama, age spots, and sites of actinic damage, arise from the accumulation of an excessive level of epidermal pigmentation. The inadequacy of current therapies to treat these conditions as well as high cytotoxicity and mutagenicity, poor skin penetration, and low stability of formulations led us to seek new whitening agents to meet the medical requirements for depigmenting agents. The inhibitory effect of licorice extract on tyrosinase activity was higher than that expected from the level of glabridin in the extract. This led us to test for other components that may contribute to this strong inhibitory activity. Results indicated that glabrene and isoliquiritigenin (2‘,4‘,4-trihydroxychalcone) in the licorice extract can inhibit both mono- and diphenolase tyrosinase activities. The IC50 values for glabrene and isoliquiritigenin were 3.5 and 8.1 μM, respectively, when tyrosine was used as substrate. The effects of glabrene and isoliquiritigenin on tyrosinase activity were dose-dependent and correlated to their ability to inhibit melanin formation in melanocytes. This is the first study indicating that glabrene and isoliquiritigenin exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, suggesting that isoflavenes and chalcones may serve as candidates for skin-lightening agents. Keywords: Tyrosinase; whitening agents; isoflavans; glabrene; chalcones |
| doi_str_mv | 10.1021/jf020935u |
| format | Article |
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Various dermatological disorders, such as melasama, age spots, and sites of actinic damage, arise from the accumulation of an excessive level of epidermal pigmentation. The inadequacy of current therapies to treat these conditions as well as high cytotoxicity and mutagenicity, poor skin penetration, and low stability of formulations led us to seek new whitening agents to meet the medical requirements for depigmenting agents. The inhibitory effect of licorice extract on tyrosinase activity was higher than that expected from the level of glabridin in the extract. This led us to test for other components that may contribute to this strong inhibitory activity. Results indicated that glabrene and isoliquiritigenin (2‘,4‘,4-trihydroxychalcone) in the licorice extract can inhibit both mono- and diphenolase tyrosinase activities. The IC50 values for glabrene and isoliquiritigenin were 3.5 and 8.1 μM, respectively, when tyrosine was used as substrate. The effects of glabrene and isoliquiritigenin on tyrosinase activity were dose-dependent and correlated to their ability to inhibit melanin formation in melanocytes. This is the first study indicating that glabrene and isoliquiritigenin exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, suggesting that isoflavenes and chalcones may serve as candidates for skin-lightening agents. 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Psychology ; General pharmacology ; Glycyrrhiza - chemistry ; Humans ; Isoflavones - analysis ; Isoflavones - pharmacology ; Kinetics ; Medical sciences ; Melanins - biosynthesis ; Melanocytes - drug effects ; Melanocytes - metabolism ; Monophenol Monooxygenase - metabolism ; Oxidoreductases ; Peptides - analysis ; Peptides - pharmacology ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Phenols - chemistry ; Phenols - pharmacology ; Plant Extracts - pharmacology ; Plant Roots - chemistry ; Structure-Activity Relationship ; Tyrosine - metabolism</subject><ispartof>Journal of agricultural and food chemistry, 2003-02, Vol.51 (5), p.1201-1207</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-4184694b7795f548389e80572b91a057b10a0d4b1f6ac17724c2f3c4a84ff02f3</citedby><cites>FETCH-LOGICAL-a379t-4184694b7795f548389e80572b91a057b10a0d4b1f6ac17724c2f3c4a84ff02f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf020935u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf020935u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14560632$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12590456$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nerya, Ohad</creatorcontrib><creatorcontrib>Vaya, Jacob</creatorcontrib><creatorcontrib>Musa, Ramadan</creatorcontrib><creatorcontrib>Izrael, Sarit</creatorcontrib><creatorcontrib>Ben-Arie, Ruth</creatorcontrib><creatorcontrib>Tamir, Snait</creatorcontrib><title>Glabrene and Isoliquiritigenin as Tyrosinase Inhibitors from Licorice Roots</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Tyrosinase is known to be a key enzyme in melanin biosynthesis, involved in determining the color of mammalian skin and hair. Various dermatological disorders, such as melasama, age spots, and sites of actinic damage, arise from the accumulation of an excessive level of epidermal pigmentation. The inadequacy of current therapies to treat these conditions as well as high cytotoxicity and mutagenicity, poor skin penetration, and low stability of formulations led us to seek new whitening agents to meet the medical requirements for depigmenting agents. The inhibitory effect of licorice extract on tyrosinase activity was higher than that expected from the level of glabridin in the extract. This led us to test for other components that may contribute to this strong inhibitory activity. Results indicated that glabrene and isoliquiritigenin (2‘,4‘,4-trihydroxychalcone) in the licorice extract can inhibit both mono- and diphenolase tyrosinase activities. The IC50 values for glabrene and isoliquiritigenin were 3.5 and 8.1 μM, respectively, when tyrosine was used as substrate. The effects of glabrene and isoliquiritigenin on tyrosinase activity were dose-dependent and correlated to their ability to inhibit melanin formation in melanocytes. This is the first study indicating that glabrene and isoliquiritigenin exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, suggesting that isoflavenes and chalcones may serve as candidates for skin-lightening agents. Keywords: Tyrosinase; whitening agents; isoflavans; glabrene; chalcones</description><subject>Analytical, structural and metabolic biochemistry</subject><subject>Biological and medical sciences</subject><subject>Cells, Cultured</subject><subject>Chalcone - analogs & derivatives</subject><subject>Chalcone - analysis</subject><subject>Chalcone - pharmacology</subject><subject>Chalcones</subject><subject>Dose-Response Relationship, Drug</subject><subject>Enzymes and enzyme inhibitors</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Glycyrrhiza - chemistry</subject><subject>Humans</subject><subject>Isoflavones - analysis</subject><subject>Isoflavones - pharmacology</subject><subject>Kinetics</subject><subject>Medical sciences</subject><subject>Melanins - biosynthesis</subject><subject>Melanocytes - drug effects</subject><subject>Melanocytes - metabolism</subject><subject>Monophenol Monooxygenase - metabolism</subject><subject>Oxidoreductases</subject><subject>Peptides - analysis</subject><subject>Peptides - pharmacology</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Phenols - chemistry</subject><subject>Phenols - pharmacology</subject><subject>Plant Extracts - pharmacology</subject><subject>Plant Roots - chemistry</subject><subject>Structure-Activity Relationship</subject><subject>Tyrosine - metabolism</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0L1OwzAUBWALgWgpDLwAysLAEPBv7Iyogra0AlQKA4vluDa4pEmxE4m-PUat2oXpDvfT0b0HgHMErxHE6GZhIYY5Ye0B6CKGYcoQEoegC-MyFSxDHXASwgJCKBiHx6CDMMshZVkXjAelKrypTKKqeTIKdem-W-dd4z5M5apEhWS29nVwlQomGVWfrnBN7UNifb1MJk7X3mmTTOu6CafgyKoymLPt7IHX-7tZf5hOngaj_u0kVYTnTUqRoFlOC85zZhkVRORGQMZxkSMVZ4GggnNaIJspjTjHVGNLNFWC2vioJT1wtcnV8bDgjZUr75bKryWC8q8QuSsk2ouNXbXF0sz3cttABJdboIJWpfWq0i7sXTQwIzi6dONcaMzPbq_8l8w44UzOnl_k43iaD98eiHzf5yod5KJufRUr-efAX0kcgsQ</recordid><startdate>20030226</startdate><enddate>20030226</enddate><creator>Nerya, Ohad</creator><creator>Vaya, Jacob</creator><creator>Musa, Ramadan</creator><creator>Izrael, Sarit</creator><creator>Ben-Arie, Ruth</creator><creator>Tamir, Snait</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20030226</creationdate><title>Glabrene and Isoliquiritigenin as Tyrosinase Inhibitors from Licorice Roots</title><author>Nerya, Ohad ; Vaya, Jacob ; Musa, Ramadan ; Izrael, Sarit ; Ben-Arie, Ruth ; Tamir, Snait</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-4184694b7795f548389e80572b91a057b10a0d4b1f6ac17724c2f3c4a84ff02f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Analytical, structural and metabolic biochemistry</topic><topic>Biological and medical sciences</topic><topic>Cells, Cultured</topic><topic>Chalcone - analogs & derivatives</topic><topic>Chalcone - analysis</topic><topic>Chalcone - pharmacology</topic><topic>Chalcones</topic><topic>Dose-Response Relationship, Drug</topic><topic>Enzymes and enzyme inhibitors</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Glycyrrhiza - chemistry</topic><topic>Humans</topic><topic>Isoflavones - analysis</topic><topic>Isoflavones - pharmacology</topic><topic>Kinetics</topic><topic>Medical sciences</topic><topic>Melanins - biosynthesis</topic><topic>Melanocytes - drug effects</topic><topic>Melanocytes - metabolism</topic><topic>Monophenol Monooxygenase - metabolism</topic><topic>Oxidoreductases</topic><topic>Peptides - analysis</topic><topic>Peptides - pharmacology</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Phenols - chemistry</topic><topic>Phenols - pharmacology</topic><topic>Plant Extracts - pharmacology</topic><topic>Plant Roots - chemistry</topic><topic>Structure-Activity Relationship</topic><topic>Tyrosine - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nerya, Ohad</creatorcontrib><creatorcontrib>Vaya, Jacob</creatorcontrib><creatorcontrib>Musa, Ramadan</creatorcontrib><creatorcontrib>Izrael, Sarit</creatorcontrib><creatorcontrib>Ben-Arie, Ruth</creatorcontrib><creatorcontrib>Tamir, Snait</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nerya, Ohad</au><au>Vaya, Jacob</au><au>Musa, Ramadan</au><au>Izrael, Sarit</au><au>Ben-Arie, Ruth</au><au>Tamir, Snait</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Glabrene and Isoliquiritigenin as Tyrosinase Inhibitors from Licorice Roots</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2003-02-26</date><risdate>2003</risdate><volume>51</volume><issue>5</issue><spage>1201</spage><epage>1207</epage><pages>1201-1207</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Tyrosinase is known to be a key enzyme in melanin biosynthesis, involved in determining the color of mammalian skin and hair. Various dermatological disorders, such as melasama, age spots, and sites of actinic damage, arise from the accumulation of an excessive level of epidermal pigmentation. The inadequacy of current therapies to treat these conditions as well as high cytotoxicity and mutagenicity, poor skin penetration, and low stability of formulations led us to seek new whitening agents to meet the medical requirements for depigmenting agents. The inhibitory effect of licorice extract on tyrosinase activity was higher than that expected from the level of glabridin in the extract. This led us to test for other components that may contribute to this strong inhibitory activity. Results indicated that glabrene and isoliquiritigenin (2‘,4‘,4-trihydroxychalcone) in the licorice extract can inhibit both mono- and diphenolase tyrosinase activities. The IC50 values for glabrene and isoliquiritigenin were 3.5 and 8.1 μM, respectively, when tyrosine was used as substrate. The effects of glabrene and isoliquiritigenin on tyrosinase activity were dose-dependent and correlated to their ability to inhibit melanin formation in melanocytes. This is the first study indicating that glabrene and isoliquiritigenin exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, suggesting that isoflavenes and chalcones may serve as candidates for skin-lightening agents. Keywords: Tyrosinase; whitening agents; isoflavans; glabrene; chalcones</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12590456</pmid><doi>10.1021/jf020935u</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 2003-02, Vol.51 (5), p.1201-1207 |
| issn | 0021-8561 1520-5118 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Analytical, structural and metabolic biochemistry Biological and medical sciences Cells, Cultured Chalcone - analogs & derivatives Chalcone - analysis Chalcone - pharmacology Chalcones Dose-Response Relationship, Drug Enzymes and enzyme inhibitors Fundamental and applied biological sciences. Psychology General pharmacology Glycyrrhiza - chemistry Humans Isoflavones - analysis Isoflavones - pharmacology Kinetics Medical sciences Melanins - biosynthesis Melanocytes - drug effects Melanocytes - metabolism Monophenol Monooxygenase - metabolism Oxidoreductases Peptides - analysis Peptides - pharmacology Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Phenols - chemistry Phenols - pharmacology Plant Extracts - pharmacology Plant Roots - chemistry Structure-Activity Relationship Tyrosine - metabolism |
| title | Glabrene and Isoliquiritigenin as Tyrosinase Inhibitors from Licorice Roots |
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