Lignin-Derived Compounds As Efficient Laccase Mediators For
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PEER-REVIEWED REVIEW ARTICLE bioresources.com A CONCISE REVIEW OF THE NATURAL EXISTANCE, SYNTHESIS, PROPERTIES, AND APPLICATIONS OF SYRINGALDEHYDE Mohamad Nasir Mohamad Ibrahim,* R. B. Sriprasanthi, Shaharuddin Shamsudeen, Farook Adam, and Showkat A. Bhawani Syringaldehyde is a promising aromatic aldehyde that no longer deserves to remain in obscurity. It possesses worthy bioactive properties and is, therefore, used in pharmaceuticals, food, cosmetics, textiles, pulp and paper industries, and even in biological control applications. Mostly, the synthetic form of syringaldehyde is being used. This review serves as an appraisal of potential research and commercialization of naturally occurring syringaldehyde beyond the scope of the food and cosmetic industries. This article also provides a comprehensive account of the various conventional extraction and chromatographic techniques used in the separation, isolation, and quantification of syringaldehyde. Further, to understand this unique compound, a brief outline on the natural formation of syringaldehyde in lignin is accentuated in this article. Keywords: Syringaldehyde; Bioactive properties; Separation and extraction; Lignin Contact information: a: Lignocellulosic Research Group, School of Chemical Sciences, Universiti Sains Malaysia, 11800 Penang, Malaysia *Corresponding author: [email protected] INTRODUCTION The ever-increasing safety concerns over synthetic antioxidants and the harmful side effects of chemo-therapeutic drugs, coupled with their high costs (Goodwin and Shepherd 1998; Sacristán et al. 2000; Vergnenegre 2001), have created a new path for the development of cheaper, sustainable, and most crucially, natural anti-oxidants, drugs, and food additives (Garrote et al. 2004). Syringaldehyde, a compound found only in a minute quantity in nature, is believed to be a promising source that matches the above- mentioned requisites. -
Wound Induced Plant Phenolic Compounds And
WOUND INDUCED PLANT PHENOLIC COMPOUNDS AND VIRULENCE GENE EXPRESSION IN AGROBACTERIUM SPECIES by PAUL ANTHONY SPENCER B.Sc, The University of Victoria, 1985 M.Sc, The University of British Columbia, 1988 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF " ^. THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY in THE FACULTY OF GRADUATE STUDIES (Department of Botany) We accept this thesis as conforming to the required standard: THE UNIVERSITY OF BRITISH COLUMBIA April 1991 © Paul Anthony Spencer, 1991 In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree that permission for extensive copying of this thesis for scholarly purposes may be granted by the head of my department or by his or her representatives. It is understood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. Department of The University of British Columbia Vancouver, Canada DE-6 (2/88) Abstract Crown gall disease of plants is caused by introduction of foreign DNA into susceptible plant cells by strains of Agrobacterium tumefaciens. The expression of bacterial virulence genes is triggered by chemicals present in plant wound exudates. The exudates contain a number of phenolic compounds which act as chemical signals inducing expression of a number of genes directing the DNA transfer process. These are the virulence or vir genes, and virv.lac reporter gene fusions have been widely used to assay vir gene induction in Agrobacterium tumefaciens strains. -
Relationship Between the Molecular Composition, Visible Light Absorption, and Health-Related Properties of Smoldering Woodsmoke Aerosols
Atmos. Chem. Phys., 20, 539–559, 2020 https://doi.org/10.5194/acp-20-539-2020 © Author(s) 2020. This work is distributed under the Creative Commons Attribution 4.0 License. Relationship between the molecular composition, visible light absorption, and health-related properties of smoldering woodsmoke aerosols Lam Kam Chan1, Khanh Q. Nguyen1, Noreen Karim1, Yatian Yang1,a, Robert H. Rice1, Guochun He1, Michael S. Denison1, and Tran B. Nguyen1 1Department of Environmental Toxicology, University of California Davis, Davis, CA 95616, USA anow at: Department of Biochemistry and Molecular Medicine, UC Davis School of Medicine, Sacramento, CA, USA Correspondence: Tran B. Nguyen ([email protected]) Received: 21 August 2019 – Discussion started: 10 September 2019 Revised: 22 November 2019 – Accepted: 8 December 2019 – Published: 17 January 2020 Abstract. Organic aerosols generated from the smoldering biological and optical properties of the smoldering WSA are combustion of wood critically impact air quality and health not attributed to PAHs. Syringyl compounds tend to correlate for billions of people worldwide; yet, the links between with cell toxicity, while the more conjugated molecules (in- the chemical components and the optical or biological ef- cluding several compounds assigned to dimers) have higher fects of woodsmoke aerosol (WSA) are still poorly under- AhR activity and MACvis. The negative correlation between stood. In this work, an untargeted analysis of the molecu- cell toxicity and AhR activity suggests that the toxicity of lar composition of smoldering WSA, generated in a con- smoldering WSA to cells is not mediated by the AhR. Both trolled environment from nine types of heartwood fuels mass-normalized biological outcomes have a statistically sig- (African mahogany, birch, cherry, maple, pine, poplar, red nificant dependence on the degree of combustion of the oak, redwood, and walnut), identified several hundred com- wood. -
Bioresources.Com
PEER-REVIEWED ARTICLE bioresources.com FORMATION OF VANILLIN AND SYRINGALDEHYDE IN AN OXYGEN DELIGNIFICATION PROCESS Zhaojiang Wong, Kefu Chen, and Jun Li * The formation of vanillin and syringaldehyde during an oxygen delignification process was evaluated. The cleavage of conjugated Cα-Cβ bonds in phenolic lignin caused by the attack of oxygen leads to the formation of aromatic aldehydes and ketones. The formation mechanism was confirmed by the organic compounds identified in the spent liquor by GC/MS. Additionally, the formation of aromatic aldehydes and ketones of hardwood, softwood, and grass was investigated. The results showed that the formed aromatic aldehydes and ketones were related to the units of lignin structure. Among the aromatic aldehydes and ketones present in the spent liquor from oxygen delignification, vanillin and syringaldehyde are of high content, making the spent liquor a potential resource for vanillin and syringaldehyde production. Key words: Formation; Oxygen delignification; Syringaldehyde; Vanillin Contact information: State Key Laboratory of Pulp & Paper Engineering South China University of Technology, Tianhe District, Guangzhou City, China. Post code: 510640. *Corresponding author: [email protected] INTRODUCTION Vanillin and syringaldehyde are widely used aromatic molecules in the food, pharmaceutical, and cosmetic industries. At present, there are two commercial ways to carry out synthetic vanillin and syringaldehyde production, i.e. synthesis based on either petroleum-derived compounds or biomass. It is reported that up to 85% of the production is highly dependent on petroleum-derived compounds (Sales et al. 2004; Cortez and Roberto 2010; Xiang and Lee 2001). Stimulated by an awareness of energy and resources shortages, the concept of a biorefinery has attracted much attention and gained great popularity. -
Effects of Phenolic Compounds on Agrobacterium Vir Genes and Gene
Plant Science 162 (2002) 733Á/743 www.elsevier.com/locate/plantsci Effects of phenolic compounds on Agrobacterium vir genes and gene transfer induction*/a plausible molecular mechanism of phenol binding protein activation Philippe Joubert a, Daniel Beaupe`re b, Philippe Lelie`vre b, Anne Wadouachi b, Rajbir S. Sangwan a,*, Brigitte S. Sangwan-Norreel a a UPRES EA 2084, Laboratoire Androgene`se et Biotechnologie, Faculte des Sciences, Universite´ de Picardie Jules Verne, 33 rue Saint-Leu, 80039 Amiens Cedex, France b Laboratoire de Chimie Organique, Universite´ de Picardie Jules Verne, 33 rue Saint-Leu, 80039 Amiens Cedex, France Received 31 October 2001; received in revised form 8 January 2002; accepted 8 January 2002 Abstract We have studied the effects of nine new phenolic compounds: 4-(4-hydroxy-3-methoxyphenyl)-but-3-en-2-one 4, 4-(4-hydroxy-3- methoxyphenyl)-but-3-en-2-one 5, 4-hydroxy-3,5-dimethoxycinnamyl alcohol or sinapyl alcohol 6, 4-hydroxy-3,5-dimethoxy-N,N- dimethylcinnamamide 7, N-ethyl-4-hydroxy-3,5-dimethoxycinnamamide 8, 1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxy-3,5- dimethoxyphenyl)-prop-2-en-1-one 11, 1-(4-hydroxyphenyl)-3-(4-hydroxyphenyl)-prop-2-en-1-one 12, 4-(4-hydroxy-3,5-dimethox- yphenyl)-butan-2-one 13, and 1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)-propan-1-one 14,onAgrobacterium virulence gene induction, on Agrobacterium-mediated gene transfer, and on both transient and stable transformation rates on Petunia and tobacco. We confirmed that virulence induction and transformation rates are increased by the use of phenolic vir inducers bearing an unsaturated lateral chain. -
Phenolic Compounds in Naoh Extracts of UK Soils and Their Contribution to Antioxidant Capacity
Phenolic compounds in NaOH extracts of UK soils and their contribution to antioxidant capacity David L. Rimmer and Geoffrey D. Abbott School of Civil Engineering and Geosciences, Newcastle University, Newcastle upon Tyne NE1 7RU, UK, E-mail [email protected] Abstract Antioxidants are released during the extraction of soils with NaOH, which also releases phenolic compounds from plant and soil material. This raises the possibility that phenolics are important contributors to the antioxidant capacity (AOC) of soils. Both the AOCs and the concentrations of 12 phenolic compounds were measured in NaOH extracts of a range of UK soils. Samples of surface and subsurface horizons were taken from 24 sites representing the major soil types (brown soils, gleys, podzols, peats and lithomorphic soils). The internal standards method was used to quantify the phenolics, which were detected by gas chromatography. The AOC of the extracts was measured using the ABTS free radical method. There were differences in the phenolic distributions extracted from soils with different land uses/plant inputs, as well as differences between surface and subsurface samples. A linear relationship was found between the AOCs of the extracts and the sum of the phenolic compounds. The AOCs of the individual phenolic compounds were also measured. The calculated contribution of the individual phenolics to the AOC of the extracts was small and less than 10% of the total AOC in all cases. Thus the measured phenolic compounds were not important contributors to the AOCs, and other unidentified antioxidant compounds were probably present. Key Words Soil organic matter mineralization Introduction Phenolic compounds in soils have been studied for at least 50 years and much of the work related to podzolization processes (Bloomfield, 1952; Vance et al., 1986). -
Top Value-Added Chemicals from Biomass
PNNL-16983 Top Value-Added Chemicals from Biomass Volume II—Results of Screening for Potential Candidates from Biorefinery Lignin 1 JE Holladay 2 JJ Bozell 1 JF White 3 D Johnson 1 Pacific Northwest National Laboratory 2 University of Tennessee 3 National Renewable Energy Laboratory October 2007 Prepared for the U.S. Department of Energy under Contract DE-AC05-76RL01830 DISCLAIMER This report was prepared as an account of work sponsored by an agency of the United States Government. Neither the United States Government nor any agency thereof, nor Battelle Memorial Institute, nor any of their employees, makes any warranty, express or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by trade name, trademark, manufacturer, or otherwise does not necessarily constitute or imply its endorsement, recommendation, or favoring by the United States Government or any agency thereof, or Battelle Memorial Institute. The views and opinions of authors expressed herein do not necessarily state or reflect those of the United States Government or any agency thereof. PACIFIC NORTHWEST NATIONAL LABORATORY operated by BATTELLE for the UNITED STATES DEPARTMENT OF ENERGY under Contract DE-AC05-76RL01830 Printed in the United States of America Available to DOE and DOE contractors from the Office of Scientific and Technical Information, P.O. Box 62, Oak Ridge, TN 37831-0062; ph: (865) 576-8401 fax: (865) 576-5728 email: [email protected] Available to the public from the National Technical Information Service, U.S. -
Synthesis of Biobased Phloretin Analogues: an Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications
antioxidants Article Synthesis of Biobased Phloretin Analogues: An Access to Antioxidant and Anti-Tyrosinase Compounds for Cosmetic Applications Laurène Minsat 1,2 ,Cédric Peyrot 1,* , Fanny Brunissen 1 , Jean-Hugues Renault 2 and Florent Allais 1,* 1 URD Agro-Biotechnologies Industrielles (ABI), CEBB (Centre Européen de Biotechnologie et de Bioéconomie), AgroParisTech, 51110 Pomacle, France; [email protected] (L.M.); [email protected] (F.B.) 2 Université de Reims Champagne-Ardenne, CNRS, ICMR 7312, 51097 Reims, France; [email protected] * Correspondence: [email protected] (C.P.); fl[email protected] (F.A.) Abstract: The current cosmetic and nutraceutical markets are characterized by a strong consumer demand for a return to natural products that are less harmful to both the consumers and the environment than current petrosourced products. Phloretin, a natural dihydrochalcone (DHC) found in apple, has been widely studied for many years and identified as a strong antioxidant and anti- tyrosinase ingredient for cosmetic formulations. Its low concentration in apples does not allow it to be obtained by direct extraction from biomass in large quantities to meet market volumes and prices. Moreover, its remarkable structure prevents its synthesis through a green process. To overcome these issues, the synthesis of phloretin analogs appears as an alternative to access valuable compounds that Citation: Minsat, L.; Peyrot, C.; are potentially more active than phloretin itself. Under such considerations, 12 chalcones (CHs) and Brunissen, F.; Renault, J.-H.; Allais, F. 12 dihydrochalcones (DHCs) were synthesized through a green Claisen–Schmidt condensation using Synthesis of Biobased Phloretin bio-based reagents. -
Analytical Py-GC/MS of Genetically Modified Poplar for the Increased
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Ghent University Academic Bibliography Computational and Structural Biotechnology Journal 17 (2019) 599–610 Contents lists available at ScienceDirect journal homepage: www.elsevier.com/locate/csbj Analytical Py-GC/MS of Genetically Modified Poplar for the Increased Production of Bio-aromatics Gorugantu SriBala a, Hilal Ezgi Toraman a, Steffen Symoens a, Annabelle Déjardin b, Gilles Pilate b, Wout Boerjan c,d, Frederik Ronsse e, Kevin M. Van Geem a,⁎, Guy B. Marin a a Ghent University, Laboratory for Chemical Technology, Technologiepark 125, 9052 Ghent, Belgium b Institut National de la Recherche Agronomique (INRA), Unité de Recherche 0588, Amélioration, Génétique et Physiologie Forestières, 45075 Orléans,France c Ghent University, Department of Plant Biotechnology and Bioinformatics, Technologiepark 71, 9052 Ghent, Belgium. d VIB Center for Plant Systems Biology, Technologiepark 71, 9052 Ghent, Belgium e Ghent University, Department of Biosystems Engineering, Coupure Links 653, 9000 Ghent, Belgium article info abstract Article history: Genetic engineering is a powerful tool to steer bio-oil composition towards the production of speciality chemicals Received 20 December 2018 such as guaiacols, syringols, phenols, and vanillin through well-defined biomass feedstocks. Our previous work Received in revised form 11 April 2019 demonstrated the effects of lignin biosynthesis gene modification on the pyrolysis vapour compositions obtained Accepted 12 April 2019 from wood derived from greenhouse-grown poplars. In this study, field-grown poplars downregulated in the Available online 25 April 2019 genes encoding CINNAMYL ALCOHOL DEHYDROGENASE (CAD), CAFFEIC ACID O-METHYLTRANSFERASE Keywords: (COMT) and CAFFEOYL-CoA O-METHYLTRANSFERASE (CCoAOMT), and their corresponding wild type were Genetically modified poplar pyrolysed in a Py-GC/MS. -
Monomers and Polymers
RSC Advances This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. This Accepted Manuscript will be replaced by the edited, formatted and paginated article as soon as this is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/advances Page 1 of 44Journal Name RSC Advances Dynamic Article Links ► Cite this: DOI: 10.1039/c0xx00000x www.rsc.org/xxxxxx ARTICLE TYPE Naturally Occurring Phenolic Sources: Monomers and Polymers Bimlesh Lochab, *a Swapnil Shukla a and Indra K. Varma b Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX DOI: 10.1039/b000000x 5 Exploration of sustainable alternative to chemicals derived from petro-based industries is the current challenge for maintaining the balance between needs of changing world while preserving the nature. The major source for sustainable chemicals is either the natural existing plant sources or waste generated from agro-based industries.