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 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.
School of Environmental Science and Engineering, Pohang University of Science and Technology (POSTECH), Pohang 790-784, Korea.
Jong-Rok
JR
Jeon
Eun-Ju
EJ
Kim
Kumarasamy
K
Murugesan
Hyo-Keun
HK
Park
Young-Mo
YM
Kim
Jung-Hee
JH
Kwon
Wang-Gi
WG
Kim
Ji-Yeon
JY
Lee
Yoon-Seok
YS
Chang
D002392:Catechin / Q000378:metabolism; D002396:Catechols / Q000378:metabolism; D002853:Chromatography, Liquid; D003116:Color; D003373:Coumaric Acids / Q000378:metabolism; D005707:Gallic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D006202:Hair Dyes / Q000378:metabolism*; D006801:Humans; D042845:Laccase / Q000378:metabolism*; D010636:Phenols / Q000302:isolation & purification / Q000378:metabolism*; D010944:Plants / Q000737:chemistry*; D011108:Polymers / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
D002396:Catechols; D003373:Coumaric Acids; D006202:Hair Dyes; D010636:Phenols; D011108:Polymers; D005707:Gallic Acid; D002392:Catechin; C004999:ferulic acid; C001945:syringic acid; D042845:Laccase; C034221:catechol
Pediatr Dermatol. 2002 Nov-Dec;19(6):498-502
12437549
Environ Sci Technol. 2008 Sep 1;42(17):6703-9
18800552
Microb Cell Fact. 2008 Nov 20;7:32
19019256
Arch Microbiol. 2003 Mar;179(3):145-50
12610719
Appl Microbiol Biotechnol. 2009 Feb;82(2):341-50
19130052
J Agric Food Chem. 2008 Jul 9;56(13):4916-22
18557619
Biomacromolecules. 2006 Jun;7(6):1845-54
16768406
Toxicol In Vitro. 2006 Sep;20(6):801-7
16469477
FEMS Microbiol Rev. 2006 Mar;30(2):215-42
16472305
Appl Microbiol Biotechnol. 2009 Mar;82(4):605-24
19183983
Appl Environ Microbiol. 2005 Apr;71(4):1775-84
15812000
J Bacteriol. 1999 Oct;181(20):6469-77
10515939
J Med Food. 2008 Jun;11(2):385-9
18598185
Appl Microbiol Biotechnol. 2008 Dec;81(4):783-90
18987855
Trends Biotechnol. 2006 May;24(5):219-26
16574262
Colloids Surf B Biointerfaces. 2009 Feb 15;69(1):129-34
19117735
Microb Biotechnol. 2009 Mar;2(2):164-77
21261911
Toxicol Lett. 2007 Apr 25;170(2):116-23
17403587
J Esthet Dent. 2000;12(5):258-63
11338492