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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 JR, Kim EJ, Murugesan K, Park HK, Kim YM, Kwon JH, Kim WG, Lee JY, Chang YS - Microb Biotechnol (2009)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: School of Environmental Science and Engineering, Pohang University of Science and Technology (POSTECH), Pohang 790-784, Korea.

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(A) Distribution of E* value differences by the presence of additional monomers with respect to E* values of single monomers. (B) Standard deviation of the E* value differences. (C) Linear regression analysis to fit the standard deviation of the E* value differences with six variables obtained from each monomer colouration (L*, P < 0.05; a*, P > 0.05; b*, P > 0.05; (L*)2, P < 0.05; (a*)2, P > 0.05; (b*)2, P > 0.05). E* value integrating all three colour parameters, L*, a* and b*, was calculated using the formula: [(L*)2 + (a*)2 + (b*)2]1/2. AS, acetosyringone; VA, vanillic acid; SA, syringic acid; GA, gallic acid; HA, homovanillyl alcohol; PCA, p‐coumaric acid; VN, vanillin; SAH, syringaldehyde; AV, acetovanillone; GAC, guaiacol; FA, ferulic acid; CA, catechin; SCA, salicylic acid; TA, tyramine; CAC, catechol.
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f2: (A) Distribution of E* value differences by the presence of additional monomers with respect to E* values of single monomers. (B) Standard deviation of the E* value differences. (C) Linear regression analysis to fit the standard deviation of the E* value differences with six variables obtained from each monomer colouration (L*, P < 0.05; a*, P > 0.05; b*, P > 0.05; (L*)2, P < 0.05; (a*)2, P > 0.05; (b*)2, P > 0.05). E* value integrating all three colour parameters, L*, a* and b*, was calculated using the formula: [(L*)2 + (a*)2 + (b*)2]1/2. AS, acetosyringone; VA, vanillic acid; SA, syringic acid; GA, gallic acid; HA, homovanillyl alcohol; PCA, p‐coumaric acid; VN, vanillin; SAH, syringaldehyde; AV, acetovanillone; GAC, guaiacol; FA, ferulic acid; CA, catechin; SCA, salicylic acid; TA, tyramine; CAC, catechol.

Mentions: Colour values (a*, b* and L*) of natural phenolic compounds in aqueous solution were very similar to those of distilled water, indicating that phenolic compounds are poor absorbers of visible light. However, addition of laccase to samples containing single monomers or pairs of monomers resulted in visible colour generation (see Fig. S1). In general, L* (luminosity) values were evenly distributed ranging from 0 (black) to 100 (white), but a* and b* values were usually positive, suggesting that blue or green polymers are hardly achieved by laccase‐based polymerization of the naturally occurring phenols tested in the present work (Fig. 1 and Fig. S1). We also plotted L* values against a*/b* values to evaluate colour diversity, as shown in Fig. 1. The plot clearly shows that polymer colours after two‐monomer polymerizations were more diverse than seen when single‐monomer solutions were polymerized. We next evaluated the extent of colour parameter differences by monomer blending with respect to colour parameters of single monomer‐based colourations to confirm which monomers are prone to generating diverse colours with other monomers. Figure 2A shows that the extent of distribution of E* value {a representative colour value calculated from the three colour parameters using the formula: [(L*)2 + (a*)2 + (b*)2]1/2} differences by the presence of other kinds of natural phenols is narrow in cases of gallic acid and catechol although the E* value differences with the single monomers (gallic acid and catechol) were observed. These results indicate that visible colours generated from gallic acid or catechol can be changed with little colour diversity by other monomers. On the other hand, tyramine and salicylic acid show a much more broad distribution of E* value differences with other monomers (Fig. 2A), suggesting that the natural phenols can act as effective ingredients that induce colour diversity during polymeric dye synthesis. This biased tendency of each monomer for colour differentiation with other monomers raises the question whether the tendency is predictable with respect to three colour parameters of each monomer. To answer the question, first a representative value of each monomer describing the extent of colour differentiation was obtained by the standard deviation calculation from the values shown in Fig. 2A (Fig. 2B). Linear regression analysis was then performed using six variables, i.e. L*, a*, b* (L*)2 (a*)2 and (b*)2 of each monomer. The best fit is a model equation:


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 JR, Kim EJ, Murugesan K, Park HK, Kim YM, Kwon JH, Kim WG, Lee JY, Chang YS - Microb Biotechnol (2009)

(A) Distribution of E* value differences by the presence of additional monomers with respect to E* values of single monomers. (B) Standard deviation of the E* value differences. (C) Linear regression analysis to fit the standard deviation of the E* value differences with six variables obtained from each monomer colouration (L*, P < 0.05; a*, P > 0.05; b*, P > 0.05; (L*)2, P < 0.05; (a*)2, P > 0.05; (b*)2, P > 0.05). E* value integrating all three colour parameters, L*, a* and b*, was calculated using the formula: [(L*)2 + (a*)2 + (b*)2]1/2. AS, acetosyringone; VA, vanillic acid; SA, syringic acid; GA, gallic acid; HA, homovanillyl alcohol; PCA, p‐coumaric acid; VN, vanillin; SAH, syringaldehyde; AV, acetovanillone; GAC, guaiacol; FA, ferulic acid; CA, catechin; SCA, salicylic acid; TA, tyramine; CAC, catechol.
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Related In: Results  -  Collection

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getmorefigures.php?uid=PMC3815374&req=5

f2: (A) Distribution of E* value differences by the presence of additional monomers with respect to E* values of single monomers. (B) Standard deviation of the E* value differences. (C) Linear regression analysis to fit the standard deviation of the E* value differences with six variables obtained from each monomer colouration (L*, P < 0.05; a*, P > 0.05; b*, P > 0.05; (L*)2, P < 0.05; (a*)2, P > 0.05; (b*)2, P > 0.05). E* value integrating all three colour parameters, L*, a* and b*, was calculated using the formula: [(L*)2 + (a*)2 + (b*)2]1/2. AS, acetosyringone; VA, vanillic acid; SA, syringic acid; GA, gallic acid; HA, homovanillyl alcohol; PCA, p‐coumaric acid; VN, vanillin; SAH, syringaldehyde; AV, acetovanillone; GAC, guaiacol; FA, ferulic acid; CA, catechin; SCA, salicylic acid; TA, tyramine; CAC, catechol.
Mentions: Colour values (a*, b* and L*) of natural phenolic compounds in aqueous solution were very similar to those of distilled water, indicating that phenolic compounds are poor absorbers of visible light. However, addition of laccase to samples containing single monomers or pairs of monomers resulted in visible colour generation (see Fig. S1). In general, L* (luminosity) values were evenly distributed ranging from 0 (black) to 100 (white), but a* and b* values were usually positive, suggesting that blue or green polymers are hardly achieved by laccase‐based polymerization of the naturally occurring phenols tested in the present work (Fig. 1 and Fig. S1). We also plotted L* values against a*/b* values to evaluate colour diversity, as shown in Fig. 1. The plot clearly shows that polymer colours after two‐monomer polymerizations were more diverse than seen when single‐monomer solutions were polymerized. We next evaluated the extent of colour parameter differences by monomer blending with respect to colour parameters of single monomer‐based colourations to confirm which monomers are prone to generating diverse colours with other monomers. Figure 2A shows that the extent of distribution of E* value {a representative colour value calculated from the three colour parameters using the formula: [(L*)2 + (a*)2 + (b*)2]1/2} differences by the presence of other kinds of natural phenols is narrow in cases of gallic acid and catechol although the E* value differences with the single monomers (gallic acid and catechol) were observed. These results indicate that visible colours generated from gallic acid or catechol can be changed with little colour diversity by other monomers. On the other hand, tyramine and salicylic acid show a much more broad distribution of E* value differences with other monomers (Fig. 2A), suggesting that the natural phenols can act as effective ingredients that induce colour diversity during polymeric dye synthesis. This biased tendency of each monomer for colour differentiation with other monomers raises the question whether the tendency is predictable with respect to three colour parameters of each monomer. To answer the question, first a representative value of each monomer describing the extent of colour differentiation was obtained by the standard deviation calculation from the values shown in Fig. 2A (Fig. 2B). Linear regression analysis was then performed using six variables, i.e. L*, a*, b* (L*)2 (a*)2 and (b*)2 of each monomer. The best fit is a model equation:

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: School of Environmental Science and Engineering, Pohang University of Science and Technology (POSTECH), Pohang 790-784, Korea.

Show MeSH
Related in: MedlinePlus