-
International Journal of Medical... 2019The oil palm tree () from the family Arecaceae is a high oil-producing agricultural crop. A significant amount of vegetation liquor is discarded during the palm oil... (Review)
Review
The oil palm tree () from the family Arecaceae is a high oil-producing agricultural crop. A significant amount of vegetation liquor is discarded during the palm oil milling process amounting to 90 million tons per year around the world. This water-soluble extract is rich in phenolic compounds known as Oil Palm Phenolics (OPP). Several phenolic acids including the three isomers of caffeoylshikimic acid (CFA), -hydroxybenzoic acid (PHBA), protocatechuic acid (PCA) and hydroxytyrosol are among the primary active ingredients in the OPP. Previous investigations have reported several positive pharmacological potentials by OPP such as neuroprotective and atheroprotective effects, anti-tumor and reduction in Aβ deposition in Alzheimer's disease model. In the current review, the pharmacological potential for CFA, PHBA, PCA and hydroxytyrosol is carefully reviewed and evaluated.
Topics: Alzheimer Disease; Antioxidants; Arecaceae; Humans; Hydroxybenzoates; Palm Oil; Phenols
PubMed: 31217739
DOI: 10.7150/ijms.29934 -
Journal of Bacteriology Nov 2009Paenibacillus sp. (formerly Bacillus macerans) strain JJ-1b is able to grow on 4-hydroxybenzoate (4HB) as a sole source of carbon and energy and is known to degrade 4HB...
Paenibacillus sp. (formerly Bacillus macerans) strain JJ-1b is able to grow on 4-hydroxybenzoate (4HB) as a sole source of carbon and energy and is known to degrade 4HB via the protocatechuate (PCA) 2,3-cleavage pathway. However, none of the genes involved in this pathway have been identified. In this study, we identified and characterized the JJ-1b genes for the 4HB catabolic pathway via the PCA 2,3-cleavage pathway, which consisted of praR and praABEGFDCHI. Based on the enzyme activities of cell extracts of Escherichia coli carrying praI, praA, praH, praB, praC, and praD, these genes were found to code for 4HB 3-hydroxylase, PCA 2,3-dioxygenase, 5-carboxy-2-hydroxymuconate-6-semialdehyde decarboxylase, 2-hydroxymuconate-6-semialdehyde dehydrogenase, 4-oxalocrotonate (OCA) tautomerase, and OCA decarboxylase, respectively, which are involved in the conversion of 4HB into 2-hydroxypenta-2,4-dienoate (HPD). The praE, praF, and praG gene products exhibited 45 to 61% amino acid sequence identity to the corresponding enzymes responsible for the catabolism of HPD to pyruvate and acetyl coenzyme A. The deduced amino acid sequence of praR showed similarity with those of IclR-type transcriptional regulators. Reverse transcription-PCR analysis revealed that praABEGFDCHI constitute an operon, and these genes were expressed during the growth of JJ-1b on 4HB and PCA. praR-praABEGFDCHI conferred the ability to grow on 4HB to E. coli, suggesting that praEGF were functional for the conversion of HPD to pyruvate and acetyl coenzyme A. A promoter analysis suggested that praR encodes a repressor of the pra operon.
Topics: Bacillaceae; Bacterial Proteins; Base Sequence; Cloning, Molecular; Gene Expression Regulation, Bacterial; Hydroxybenzoates; Molecular Structure; Operon; RNA, Ribosomal, 16S; Transcription, Genetic
PubMed: 19717587
DOI: 10.1128/JB.00840-09 -
Biomolecules Jun 2020Biotechnological production of phenolic acids is attracting increased interest due to their superior antioxidant activity, as well as other antimicrobial, dietary, and... (Review)
Review
Biotechnological production of phenolic acids is attracting increased interest due to their superior antioxidant activity, as well as other antimicrobial, dietary, and health benefits. As secondary metabolites, primarily found in plants and fungi, they are effective free radical scavengers due to the phenolic group available in their structure. Therefore, phenolic acids are widely utilised by pharmaceutical, food, cosmetic, and chemical industries. A demand for phenolic acids is mostly satisfied by utilising chemically synthesised compounds, with only a low quantity obtained from natural sources. As an alternative to chemical synthesis, environmentally friendly bio-based technologies are necessary for development in large-scale production. One of the most promising sustainable technologies is the utilisation of microbial cell factories for biosynthesis of phenolic acids. In this paper, we perform a systematic comparison of the best known natural sources of phenolic acids. The advances and prospects in the development of microbial cell factories for biosynthesis of these bioactive compounds are discussed in more detail. A special consideration is given to the modern production methods and analytics of phenolic acids.
Topics: Biotechnology; Hydroxybenzoates; Molecular Structure
PubMed: 32517243
DOI: 10.3390/biom10060874 -
Genetics and Molecular Research : GMR Dec 2006Corynebacterium glutamicum is a gram-positive soil microorganism able to utilize a large variety of aromatic compounds as the sole carbon source. The corresponding... (Review)
Review
Corynebacterium glutamicum is a gram-positive soil microorganism able to utilize a large variety of aromatic compounds as the sole carbon source. The corresponding catabolic routes are associated with multiple ring-fission dioxygenases and among other channeling reactions, include the gentisate pathway, the protocatechuate and catechol branches of the beta-ketoadipate pathway and two potential hydroxyquinol pathways. Genes encoding the enzymatic machinery for the bioconversion of aromatic compounds are organized in several clusters in the C. glutamicum genome. Expression of the gene clusters is under specific transcriptional control, apparently including eight DNA-binding proteins belonging to the AraC, IclR, LuxR, PadR, and TetR families of transcriptional regulators. Expression of the gentisate pathway involved in the utilization of 3-hydroxybenzoate and gentisate is positively regulated by an IclR-type activator. The metabolic channeling of ferulate, vanillin and vanillate into the protocatechuate branch of the beta-ketoadipate pathway is controlled by a PadR-like repressor. Regulatory proteins of the IclR and LuxR families participate in transcriptional regulation of the branches of the beta-ketoadipate pathway that are involved in the utilization of benzoate, 4-hydroxybenzoate and protocatechuate. The channeling of phenol into this pathway may be under positive transcriptional control by an AraC-type activator. One of the potential hydroxyquinol pathways of C. glutamicum is apparently repressed by a TetR-type regulator. This global analysis revealed that transcriptional regulation of aromatic compound utilization is mainly controlled by single regulatory proteins sensing the presence of aromatic compounds, thus representing single input motifs within the transcriptional regulatory network of C. glutamicum.
Topics: Biodegradation, Environmental; Corynebacterium glutamicum; Gene Expression Regulation, Bacterial; Hydrocarbons, Aromatic; Hydroxybenzoates; Transcription, Genetic
PubMed: 17183485
DOI: No ID Found -
Nutrients Nov 2018Cereal grains represent one of the major sources of human food and nowadays, their production has increased to fulfill the needs of the world's population. Among whole... (Review)
Review
Cereal grains represent one of the major sources of human food and nowadays, their production has increased to fulfill the needs of the world's population. Among whole grains, wheat is the most popular and contributes significantly to the human diet. Whole grains possess great nutritional and bioactive properties due to their fractions, bran and germ, that comprise unique health-promoting bioactive components. The evidence of health benefits in human intervention studies, as well as a World Health Organization report for 2012⁻2016, supports the dietary consumption of whole grains and whole-grain foods. The inverse correlation between whole grain consumption and the reduced risk of chronic diseases and metabolic syndromes was underlined by several epidemiological studies. This article focuses on the bioactive components of whole grains and their fractions, namely phenolic acids, starting from their chemical structure, bioactivity and bioavailability. According to the conclusive evaluation of the human intervention studies conducted using cereal bran and whole grains intake, the assumption that the bioactive compounds determine health outcomes is illustrated. In the last part of the work, the functional potential and the health claims related to whole grains and bran intake are discussed, as well as new technologies and strategies to enhance their health potential by an increased bioavailability.
Topics: Biological Availability; Cardiovascular Diseases; Diet; Humans; Hydroxybenzoates; Whole Grains
PubMed: 30388881
DOI: 10.3390/nu10111615 -
Synergistic Effects of Butyl Para-Hydroxybenzoate and Mild Heating on Foodborne Pathogenic Bacteria.Journal of Food Protection Apr 2021Although high-temperature heat treatments can efficiently reduce pathogen levels, they also affect the quality and nutritional profile of foods and increase the cost of...
ABSTRACT
Although high-temperature heat treatments can efficiently reduce pathogen levels, they also affect the quality and nutritional profile of foods and increase the cost of processing. The food additive butyl para-hydroxybenzoate (BPB) was investigated for its potential to synergistically enhance thermal microbial inactivation at mild heating temperatures (54 to 58°C). Four foodborne pathogenic bacteria, Cronobacter sakazakii, Salmonella enterica Typhimurium, attenuated Escherichia coli O157:H7, and Listeria monocytogenes, were cultured to early stationary phase and then subjected to mild heating at 58, 55, 57, and 54°C, respectively, in a model food matrix (brain heart infusion [BHI]) containing low concentrations of BPB (≤125 ppm). The temperature used with each bacterium was selected based on the temperature that would yield an approximately 1- to 3-log reduction over 15 min of heating in BHI without BPB in a submerged coil system. The inclusion of BPB at ≤125 ppm resulted in significant enhancement of thermal inactivation, achieving 5- to >6-log reductions of the gram-negative strains with D-values of <100 s. A 3- to 4-log reduction of L. monocytogenes was achieved with a similar treatment. No significant microbial inactivation was noted in the absence of mild heating for the same time period. This study provides additional proof of concept that low-temperature inactivation of foodborne pathogens can be realized by synergistic enhancement of thermal inactivation by additives that affect microbial cell membranes.
Topics: Colony Count, Microbial; Escherichia coli O157; Food Microbiology; Heating; Hydroxybenzoates; Listeria monocytogenes
PubMed: 33159441
DOI: 10.4315/JFP-20-175 -
Nutrients Sep 2021Seven derivatives of plant-derived hydroxybenzoic acid (HBA)-including 2,3-dihydroxybenzoic (2,3-DHB, pyrocatechuic), 2,4-dihydroxybenzoic (2,4-DHB, β-resorcylic),...
Plant-Derived and Dietary Hydroxybenzoic Acids-A Comprehensive Study of Structural, Anti-/Pro-Oxidant, Lipophilic, Antimicrobial, and Cytotoxic Activity in MDA-MB-231 and MCF-7 Cell Lines.
Seven derivatives of plant-derived hydroxybenzoic acid (HBA)-including 2,3-dihydroxybenzoic (2,3-DHB, pyrocatechuic), 2,4-dihydroxybenzoic (2,4-DHB, β-resorcylic), 2,5-dihydroxybenzoic (2,5-DHB, gentisic), 2,6-dihydroxybenzoic (2,6-DHB, γ-resorcylic acid), 3,4-dihydroxybenzoic (3,4-DHB, protocatechuic), 3,5-dihydroxybenzoic (3,5-DHB, α-resorcylic), and 3,4,5-trihydroxybenzoic (3,4,5-THB, gallic) acids-were studied for their structural and biological properties. Anti-/pro-oxidant properties were evaluated by using DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), FRAP (ferric-reducing antioxidant power), CUPRAC (cupric-reducing antioxidant power), and Trolox oxidation assays. Lipophilicity was estimated by means of experimental (HPLC) and theoretical methods. The antimicrobial activity against (), (), (), (), (), and () was studied. The cytotoxicity of HBAs in MCF-7 and MDA-MB-231 cell lines was estimated. Moreover, the structure of HBAs was studied by means of experimental (FTIR, H, and C NMR) and quantum chemical DFT methods (the NBO and CHelpG charges, electrostatic potential maps, and electronic parameters based on the energy of HOMO and LUMO orbitals). The aromaticity of HBA was studied based on the calculated geometric and magnetic aromaticity indices (HOMA, Aj, BAC, I6, NICS). The biological activity of hydroxybenzoic acids was discussed in relation to their geometry, the electronic charge distribution in their molecules, their lipophilicity, and their acidity. Principal component analysis (PCA) was used in the statistical analysis of the obtained data and the discussion of the dependency between the structure and activity (SAR: structure-activity relationship) of HBAs. This work provides valuable information on the potential application of hydroxybenzoic acids as bioactive components in dietary supplements, functional foods, or even drugs.
Topics: Anti-Infective Agents; Antioxidants; Cell Line, Tumor; Cytotoxins; Humans; Hydroxybenzoates; MCF-7 Cells; Plant Extracts; Reactive Oxygen Species; Structure-Activity Relationship
PubMed: 34578985
DOI: 10.3390/nu13093107 -
Microbial Cell Factories May 2018Hydroxybenzoic acids are industrially relevant aromatic compounds, which also play key roles in the microbial carbon metabolism, e.g., as precursors for the synthesis of...
BACKGROUND
Hydroxybenzoic acids are industrially relevant aromatic compounds, which also play key roles in the microbial carbon metabolism, e.g., as precursors for the synthesis of cofactors or metal-chelating molecules. Due to its pronounced resistance to aromatics Corynebacterium glutamicum represents an interesting platform for production of these compounds. Unfortunately, a complex catabolic network for aromatic molecules prevents application of C. glutamicum for microbial production of aromatic compounds other than aromatic amino acids, which cannot be metabolized by this microorganism.
RESULTS
We completed the construction of the platform strain C. glutamicum DelAro, in which the deletion of altogether 27 genes in five gene clusters abolished most of the peripheral and central catabolic pathways for aromatic compounds known in this microorganism. The obtained strain was subsequently applied for the production of 2-hydroxybenzoate (salicylate), 3-hydroxybenzoate, 4-hydroxybenzoate and protocatechuate, which all derive from intermediates of the aromatic amino acid-forming shikimate pathway. For an optimal connection of the designed hydroxybenzoate production pathways to the host metabolism, C. glutamicum was additionally engineered towards increased supply of the shikimate pathway substrates erythrose-4-phosphate and phosphoenolpyruvate by manipulation of the glucose transport and key enzymatic activities of the central carbon metabolism. With an optimized genetic background the constructed strains produced 0.01 g/L (0.07 mM) 2-hydroxybenzoate, 0.3 g/L (2.2 mM) 3-hydroxybenzoate, 2.0 g/L (13.0 mM) protocatechuate and 3.3 g/L (23.9 mM) 4-hydroxybenzoate in shaking flasks.
CONCLUSION
By abolishing its natural catabolic network for aromatic compounds, C. glutamicum was turned into a versatile microbial platform for aromatics production, which could be exemplarily demonstrated by rapidly engineering this platform organism towards producing four biotechnologically interesting hydroxybenzoates. Production of these compounds was optimized following different metabolic engineering strategies leading to increased precursor availability. The constructed C. glutamicum strains are promising hosts for the production of hydroxybenzoates and other aromatic compounds at larger scales.
Topics: Corynebacterium glutamicum; Hydroxybenzoates; Metabolic Engineering
PubMed: 29753327
DOI: 10.1186/s12934-018-0923-x -
Applied and Environmental Microbiology May 2021A novel gene cluster involved in the degradation of lignin-derived monoaromatics such as -hydroxybenzoate, vanillate, and ferulate has been identified in the...
A novel gene cluster involved in the degradation of lignin-derived monoaromatics such as -hydroxybenzoate, vanillate, and ferulate has been identified in the thermophilic nitrate reducer JL-2. Based on conserved domain analyses and metabolic pathway mapping, the cluster was classified into upper- and peripheral-pathway operons. The upper-pathway genes, responsible for the degradation of -hydroxybenzoate and vanillate, are located on a 0.27-Mb plasmid, whereas the peripheral-pathway genes, responsible for the transformation of ferulate, are spread throughout the plasmid and the chromosome. In addition, a lower-pathway operon was also identified in the plasmid that corresponds to the cleavage pathway of catechol. Spectrophotometric and gene induction data suggest that the upper and lower operons are induced by -hydroxybenzoate, which the strain can degrade completely within 4 days of incubation, whereas the peripheral genes are expressed constitutively. The upper degradation pathway follows a less common route, proceeding via the decarboxylation of protocatechuate to form catechol, and involves a novel thermostable γ-carboxymuconolactone decarboxylase homolog, identified as protocatechuate decarboxylase based on gene deletion experiments. This gene cluster is conserved in only a few members of the and shows traces of vertical expansion of catabolic pathways in these organisms toward lignoaromatics. High-temperature steam treatment of lignocellulosic biomass during the extraction of cellulose and hemicellulose fractions leads to the release of a wide array of lignin-derived aromatics into the natural ecosystem, some of which can have detrimental effects on the environment. Not only will identifying organisms capable of using such aromatics aid in environmental cleanup, but thermostable enzymes, if characterized, can also be used for efficient lignin valorization. However, no thermophilic lignin degraders have been reported thus far. The present study reports JL-2 as a thermophilic bacterium with the potential to use lignin-derived aromatics. The identification of a novel thermostable protocatechuate decarboxylase gene in the strain further adds to its significance, as such an enzyme can be efficiently used in the biosynthesis of ,-muconate, an important intermediate in the commercial production of plastics.
Topics: Coumaric Acids; Genes, Bacterial; Lignin; Multigene Family; Parabens; Thermus; Vanillic Acid
PubMed: 33741620
DOI: 10.1128/AEM.01589-20 -
Marine Drugs Jul 2022A series of phenolic acid chitooligosaccharide (COS) derivatives synthesized by two mild and green methods were illuminated in this paper. Seven phenolic acids were...
A series of phenolic acid chitooligosaccharide (COS) derivatives synthesized by two mild and green methods were illuminated in this paper. Seven phenolic acids were selected to combine two kinds of COS derivatives: the phenolic acid chitooligosaccharide salt derivatives and the phenolic-acid-acylated chitooligosaccharide derivatives. The structures of the derivatives were characterized by FT-IR and H NMR spectra. The antioxidant experiment results in vitro (including DPPH-radical scavenging activity, superoxide-radical scavenging activity, hydroxyl-radical scavenging ability, and reducing power) demonstrated that the derivatives exhibited significantly enhanced antioxidant activity compared to COS. Moreover, the study showed that the phenolic acid chitooligosaccharide salts had stronger antioxidant activity than phenolic-acid-acylated chitooligosaccharide. The cytotoxicity assay of L929 cells in vitro indicated that the derivatives had low cytotoxicity and good biocompatibility. In conclusion, this study provides a possible synthetic method for developing novel and nontoxic antioxidant agents which can be used in the food and cosmetics industry.
Topics: Antioxidants; Chitosan; Hydroxybenzoates; Oligosaccharides; Spectroscopy, Fourier Transform Infrared
PubMed: 36005492
DOI: 10.3390/md20080489