Laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: Enzymatic colourations driven by homo‐ or hetero‐polymer synthesis
Laccase efficiently catalyses polymerization of phenolic compounds. However, knowledge on applications of polymers synthesized in this manner remains scarce. Here, the potential of laccase‐catalysed polymerization of natural phenols to form products useful in hair dyeing was investigated. All 15 tes...
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| Format: | Online |
| Language: | English |
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Blackwell Publishing Ltd
2010
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| Online Access: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815374/ |
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pubmed-38153742014-02-12 Laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: Enzymatic colourations driven by homo‐ or hetero‐polymer synthesis Jeon, Jong‐Rok Kim, Eun‐Ju Murugesan, Kumarasamy Park, Hyo‐Keun Kim, Young‐Mo Kwon, Jung‐Hee Kim, Wang‐Gi Lee, Ji‐Yeon Chang, Yoon‐Seok Research Articles Laccase efficiently catalyses polymerization of phenolic compounds. However, knowledge on applications of polymers synthesized in this manner remains scarce. Here, the potential of laccase‐catalysed polymerization of natural phenols to form products useful in hair dyeing was investigated. All 15 tested phenols yielded coloured products after laccase treatment and colour diversity was attained by using mixtures of two phenolic monomers. After exploring colour differentiation pattern of 120 different reactions with statistical regression analysis, three monomer combinations, namely gallic acid and syringic acid, catechin and catechol, and ferulic acid and syringic acid, giving rise to brown, black, and red materials, respectively, were further characterized because such colours are commercially important for grey hair dyeing. Selected polymers could strongly absorb visible light and their hydrodynamic sizes ranged from 100 to 400 nm. Analyses of enzyme kinetic constants, liquid chromatography and electrospray ionization‐mass spectrometry (ESI‐MS) coupled with collision‐induced dissociation MS/MS indicate that both monomers in reactions involving catechin and catechol, and ferulic acid and syringic acid, are coloured by heteropolymer synthesis, but the gallic acid/syringic acid combination is based on homopolymer mixture formation. Comparison of colour parameters from these three reactions with those of corresponding artificial homopolymer mixtures also supported the idea that laccase may catalyse either hetero‐ or homo‐polymer synthesis. We finally used selected materials to dye grey hair. Each material coloured hair appropriately and the dyeing showed excellent resistance to conventional shampooing. Our study indicates that laccase‐catalysed polymerization of natural phenols is applicable to the development of new cosmetic pigments. Blackwell Publishing Ltd 2010-05 2010-04-20 /pmc/articles/PMC3815374/ /pubmed/21255331 http://dx.doi.org/10.1111/j.1751-7915.2009.00153.x Text en Copyright© 2009 The Authors. Journal compilation © 2009 Society for Applied Microbiology and Blackwell Publishing Ltd |
| repository_type |
Open Access Journal |
| institution_category |
Foreign Institution |
| institution |
US National Center for Biotechnology Information |
| building |
NCBI PubMed |
| collection |
Online Access |
| language |
English |
| format |
Online |
| author |
Jeon, Jong‐Rok Kim, Eun‐Ju Murugesan, Kumarasamy Park, Hyo‐Keun Kim, Young‐Mo Kwon, Jung‐Hee Kim, Wang‐Gi Lee, Ji‐Yeon Chang, Yoon‐Seok |
| spellingShingle |
Jeon, Jong‐Rok Kim, Eun‐Ju Murugesan, Kumarasamy Park, Hyo‐Keun Kim, Young‐Mo Kwon, Jung‐Hee Kim, Wang‐Gi Lee, Ji‐Yeon Chang, Yoon‐Seok Laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: Enzymatic colourations driven by homo‐ or hetero‐polymer synthesis |
| author_facet |
Jeon, Jong‐Rok Kim, Eun‐Ju Murugesan, Kumarasamy Park, Hyo‐Keun Kim, Young‐Mo Kwon, Jung‐Hee Kim, Wang‐Gi Lee, Ji‐Yeon Chang, Yoon‐Seok |
| author_sort |
Jeon, Jong‐Rok |
| title |
Laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: Enzymatic colourations driven by homo‐ or hetero‐polymer synthesis |
| title_short |
Laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: Enzymatic colourations driven by homo‐ or hetero‐polymer synthesis |
| title_full |
Laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: Enzymatic colourations driven by homo‐ or hetero‐polymer synthesis |
| title_fullStr |
Laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: Enzymatic colourations driven by homo‐ or hetero‐polymer synthesis |
| title_full_unstemmed |
Laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: Enzymatic colourations driven by homo‐ or hetero‐polymer synthesis |
| title_sort |
laccase‐catalysed polymeric dye synthesis from plant‐derived phenols for potential application in hair dyeing: enzymatic colourations driven by homo‐ or hetero‐polymer synthesis |
| description |
Laccase efficiently catalyses polymerization of phenolic compounds. However, knowledge on applications of polymers synthesized in this manner remains scarce. Here, the potential of laccase‐catalysed polymerization of natural phenols to form products useful in hair dyeing was investigated. All 15 tested phenols yielded coloured products after laccase treatment and colour diversity was attained by using mixtures of two phenolic monomers. After exploring colour differentiation pattern of 120 different reactions with statistical regression analysis, three monomer combinations, namely gallic acid and syringic acid, catechin and catechol, and ferulic acid and syringic acid, giving rise to brown, black, and red materials, respectively, were further characterized because such colours are commercially important for grey hair dyeing. Selected polymers could strongly absorb visible light and their hydrodynamic sizes ranged from 100 to 400 nm. Analyses of enzyme kinetic constants, liquid chromatography and electrospray ionization‐mass spectrometry (ESI‐MS) coupled with collision‐induced dissociation MS/MS indicate that both monomers in reactions involving catechin and catechol, and ferulic acid and syringic acid, are coloured by heteropolymer synthesis, but the gallic acid/syringic acid combination is based on homopolymer mixture formation. Comparison of colour parameters from these three reactions with those of corresponding artificial homopolymer mixtures also supported the idea that laccase may catalyse either hetero‐ or homo‐polymer synthesis. We finally used selected materials to dye grey hair. Each material coloured hair appropriately and the dyeing showed excellent resistance to conventional shampooing. Our study indicates that laccase‐catalysed polymerization of natural phenols is applicable to the development of new cosmetic pigments. |
| publisher |
Blackwell Publishing Ltd |
| publishDate |
2010 |
| url |
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815374/ |
| _version_ |
1612022784285736960 |