Spectroscopic analyses of the biofuels-critical phytochemical coniferyl alcohol and its enzyme-catalyzed oxidation products

Molecules

Volumn 14, Issue 11, 2009, Pages 4758-4778

  Achyuthan, Komandoor Elayavalli ^a,b   Adams, Paul David ^a,c   Simmons, Blake Alexander ^a,d   Singh, Anup Kumar ^a,d  

^a JOINT BIOENERGY INSTITUTE   (United States)

^b SANDIA NATIONAL LABORATORIES   (United States)

^c LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^d SANDIA NATIONAL LABORATORIES   (United States)

Author keywords

Absorption spectroscopy; Biofuels; Coniferyl alcohol; High throughput screening; Monolignols

Indexed keywords

BIOFUEL; CONIFERYL ALCOHOL; LACCASE; LIGNIN; PEROXIDASE; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION;

BIOFUELS; CATALYSIS; LACCASE; LIGNIN; OXIDATION-REDUCTION; PEROXIDASES; PHENOLS;

EID: 73349109467     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14114758     Document Type: Article

References (39)

1. Campbell, M. M.; Sederoff, R. R. Variation in lignin content and composition. Plant Physiol. 1996, 110, 3-13.
2. Tzfira, T.; Zuker, A.; Altman, A. Forest-tree biotechnology: genetic transformation and its application to future forests. Trends Biotechnol. 1998, 16, 439-446.
3. Simmons, B. A.; Loque, D.; Blanch, H. W. Next-generation biomass feedstocks for biofuel production. Genome Biol. 2008, 9, 242:1-242:6.
4. Anterola, A. M.; Lewis, N. G. Trends in lignin modification: a comprehensive analysis of the effects of genetic manipulations/mutations on lignifications and vascular integrity. Phytochemistry 2002, 61, 221-294.
5. Taherzadeh, M. J.; Karimi, K. Pretreatment of lignocellulosic wastes to improve ethanol and biogas production: a review. Int. J. Mol. Sci. 2008, 9, 1621-1651.
6. Ferraz, A.; Rodriguez, J.; Freer, J.; Baeza, J. Biodegradation of Pinus radiata softwood by whiteand brown-rot fungi. World J. Microbiol. Biotechnol. 2001, 17, 31-34.
7. Leonowicz, A.; Cho, N. S.; Luterek, J.; Wilkolazka, A.; Wojtaswasilewska, M.; Matuszewska, A.; Hofrichter, M.; Wesenberg, D.; Rogalski, J. Fungal laccase: Properties and activity on lignin. J. Basic Microbiol. 2001, 41, 183-225.
8. Hernandez Fernaud, J. R.; Carnicero, A.; Perestelo, F.; Hernandez Cutuli, M.; Arias, E.; Falconi, M. A. Upgrading of an industrial lignin by using laccase produced by Fusarium proliferatum and different laccase-mediator systems. Enz. Microb. Technol. 2006, 38, 40-48.
9. Ruiz-Duenas, F. J.; Martinez, A. T. Microbial degradation of lignin: how a bulky recalcitrant polymer is efficiently recycled in nature and how we can take advantage of this. Microb. Biotechnol. 2009, 2, 164-177.
10. Achyuthan, K. E.; McClain, J. L.; Raj, D. Orthogonal spectroscopic high-throughput screening of laccase-catalyzed p-cresol oxidation. Comb. Chem. High Throughput Screen. 2009, 12, 678-689.
11. Harper, J. C.; Brozik, S. M.; Flemming, J. H.; McClain, J. L.; Polsky, R.; Raj, D.; Ten Eyck, G. A.; Wheeler, D. R.; Achyuthan, K. E. Fabrication and testing of a microneedles sensor array for p cresol detection with potential biofuel applications. ACS Appl. Mater. Interfaces 2009, 1, 1591-1598.
12. Fourand, D.; Cathala, B.; Lapierre, C. Initial steps of the peroxidase-catalyzed polymerization of coniferyl alcohol and/or sinapyl aldehyde: capillary zone electrophoresis study of pH effect. Phytochemistry 2003, 62, 139-146.
13. Madzak, C.; Mimmi, M. C.; Caminde, E.; Brault, A.; Baumberger, S.; Briozzo, P.; Mougin, C.; Jolivalt, C. Shifting the optimal pH of activity for a laccase from the fungus Trametes versicolor by structure-based mutagenesis. Protein Eng. Des. Sel. 2006, 19, 77-84.
14. Cathala, B.; Aguie-Beghin, V.; Douillard, R. Coniferyl alcohol reactivity at the air/water interface. C. R. Biol. 2004, 327, 777-784.
15. Savidge, R. A.; Forster, H. Coniferyl alcohol metabolism in conifers-II. Coniferyl alcohol and dihydroconiferyl alcohol biosynthesis. Phytochemistry 2001, 57, 1095-1103.
16. Bao, W.; O'Malley, D. M.; Whetten, R.; Sederoff, R. R. A laccase associated with lignifications in Loblolly Pine xylem. Science 1993, 260, 672-674.
17. Castle, L. A.; Smith, K. D.; Morris, R. O. Cloning and sequencing of an Agrobacterium tumefaciens β-glucosidase gene involved in modifying a vir-inducing plant signal molecule. J. Bacteriol. 1992, 174, 1478-1486.
18. Bhuiya, M. W.; Liu, C. J. A cost-effective colorimetric assay for phenolic O-methyl transferases and characterization of caffeate 3-O-methyl transferases from Populus trichocarpa. Anal. Biochem. 2009, 384, 151-158.
19. Achyuthan, K. E.; Whitten, D. G. Design considerations for high-throughput screening and in vitro diagnostic assays. Comb. Chem. High Throughput Screen. 2007, 10, 399-412.
20. Aoyama, W.; Sasaki, S.; Matsumara, S.; Mitsunaga, T.; Hirai, H.; Tsutsumi, Y.; Nishida, T. Sinapyl alcohol-specific peroxidase isoenzyme catalyzes the formation of the dehydrogenative polymer from sinapyl alcohol. J. Wood Sci. 2002, 48, 497-504.
21. Koutaniemi, S.; Toikka, M. M.; Karkonen, A.; Mustonen, M.; Lundell, T.; Simola, L. K.; Kilpelainen, I. A.; Teeri, T. H. Characterization of basic p-coumaryl and coniferyl alcohol oxidizing peroxidases from a lignin-forming Picea abies suspension culture. Plant Mol. Biol. 2005, 58, 141-157.
22. Lee, B. R.; Kim, K. Y.; Jung, W. J.; Avice, J. C.; Ourry, A.; Kim, T. H. Peroxidases and lignifications in relation to the intensity of water-deficit stress in white clover (Trifolium repens L.). J. Exp. Bot. 2007, 58, 1271-1279.
23. Quiroga, M.; de Forchetti, S. M.; Taleisnik, E.; Tigier, H. Tomato root peroxidase isoenzymes: kinetic studies of the coniferyl alcohol peroxidase activity, immunological properties and role in response to salt stress. J. Plant Physiol. 2007, 158, 1007-1013.
24. Talano, M. A.; Agostini, E.; Oller, A. L. W.; Medina, M. I.; de Forchetti, S. R. M. Modulator role of ascorbic acid on coniferyl alcohol oxidation by a basic peroxidase from tomato hairy roots. Plant Sci. 2008, 175, 724-730.
25. Jin, J.; Mazon, H.; van den Heuvel, R. H. H.; Janssen, D. B.; Fraaije, M. W. Discovery of a eugenol oxidase from Rhodococcus sp. Strain RHA1. FEBS J. 2007, 274, 2311-2321.
26. Mitchell, H. J.; Hall, J. L.; M. S. Barber, M. S. Elicitor-induced cinnamyl alcohol dehydrogenase activity in lignifying wheat (Triticum aestivum L.) leaves. Plant Physiol. 1994, 104, 551-556.
27. De Ascensao, A. R.; Dubery, I. A. Panama disease: Cell wall reinforcement in banana roots in response to elicitors from Fusarium oxysporum f. sp. cubense Race Four. Phytopathology 2000, 90, 1173-1180.
28. Overhage, J.; Steinbuchel, A.; Priefert, H. Biotransformation of eugenol to ferulic acid by a recombinant strain of Ralstonia cutropha H16. Appl. Environ. Microbiol. 2002, 68, 4315-4321.
29. Wallace, G.; Fry, S. C. Action of diverse peroxidases and laccases on six cell wall-related phenolic compounds. Phytochemistry 1999, 52, 769-773.
30. Ragnar, M.; Lindgren, C. T.; Nilvebrant, N. O. pKa-values of guaiacyl and syringyl phenols related to lignin. J. Wood Chem. Technol. 2000, 20, 277-305.
31. Fraaije, M. W.; Veeger, C.; van Berkel, W. J. H. Substrate specificity of flavin-dependent vanillylalcohol oxidase from Penicillium simplicissimum. Evidence for the production of 4-hydroxycinnamyl alcohols from 4-allylphenols. Eur. J. Biochem. 1995, 234, 271-277.
32. Haghighi, B.; Gorton, L.; Ruzgas, T.; Jonsson, L. J. Characterization of graphite electrodes modified with laccase from Trametes versicolor and their use for bioelectrochemical monitoring of phenolic compounds in flow injection analysis. Anal. Chim. Acta 2003, 487, 3-14.
33. Jarosz-Wilkolazka, A.; Ruzgas, T.; Gorton, L. Amperometric detection of mono-and diphenols at Cerrena unicolor laccase-modified graphite electrode: correlation between sensitivity and substrate structure. Talanta 2005, 66, 1219-1224.
34. van der Hage, E. R. E.; Boon, J. J. On-line Curie-point pyrolysis-high-performance liquid chromatographic-mass spectrometric analysis of lignin polymers. J. Chromatogr. A 1996, 736, 61-75.
35. Watt, D. K.; Ono, H.; Hayashi, K. Agrobacterium tumefaciens β-glucosidase is also an effective β-xylosidase, and has a high transglycosylation activity in the presence of alcohols. Biochim. Biophys. Acta 1998, 1385, 78-88.
36. Escamilla-Trevino, L. L.; Chen, W.; Card, M. L.; Shih, M. C.; Cheng, C. L.; Poulton, J. E. Arabidopsis thaliana β-glucosidases BGLU45 and BGLU46 hydrolyse monolignol glucosides. Phytochemistry 2006, 67, 1651-1660.
37. Labudzinska, A.; Gorczynska, K. The UV difference spectra as a characteristic feature of phenols and aromatic amines. J. Mol. Struct. 1995, 349, 469-472.
38. Calderon, A. A.; Munoz, R.; Morales, M.; Ros Barcelo, A. A comparative study of two spectrophotometric methods for measuring coniferyl alcohol oxidation catalysed by peroxidase. Phytochem. Anal. 1992, 3, 238-240.
39. Shiba, T.; Xiao, L.; Miyakoshi, T.; Chen, C. L. Oxidation of isoeugenol and coniferyl alcohol catalyzed by laccases isolated from Rhus vernicifera Stokes and Pycnoporus coccineus. J. Mol. Catal. B Enzym. 2000, 10, 605-615. © 2009