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Molecular Plant Jan 2015Plant benzoic acids (BAs) are building blocks or important structural elements for numerous primary and specialized metabolites, including plant hormones, cofactors,... (Review)
Review
Plant benzoic acids (BAs) are building blocks or important structural elements for numerous primary and specialized metabolites, including plant hormones, cofactors, defense compounds, and attractants for pollinators and seed dispersers. Many natural products derived from plant BAs or containing benzoyl/benzyl moieties are also of medicinal or nutritional value to humans. Biosynthesis of BAs in plants is a network involving parallel and intersecting pathways spread across multiple subcellular compartments. In this review, a current overview on the metabolism of plant BAs is presented with a focus on the recent progress made on isolation and functional characterization of genes encoding biosynthetic enzymes and intracellular transporters. In addition, approaches for deciphering the complex interactions between pathways of the BAs network are discussed.
Topics: Benzoates; Metabolic Networks and Pathways; Plants; Propanols; Salicylic Acid
PubMed: 25578274
DOI: 10.1016/j.molp.2014.12.001 -
Nature Communications Nov 2022Plasmonic hot carriers have the advantage of focusing, amplifying, and manipulating optical signals via electron oscillations which offers a feasible pathway to...
Plasmonic hot carriers have the advantage of focusing, amplifying, and manipulating optical signals via electron oscillations which offers a feasible pathway to influence catalytic reactions. However, the contribution of nonmetallic hot carriers and thermal effects on the overall reactions are still unclear, and developing methods to enhance the efficiency of the catalysis is critical. Herein, we proposed a new strategy for flexibly modulating the hot electrons using a nonmetallic plasmonic heterostructure (named WO-nanowires/reduced-graphene-oxides) for isopropanol dehydration where the reaction rate was 180-fold greater than the corresponding thermocatalytic pathway. The key detail to this strategy lies in the synergetic utilization of ultraviolet light and visible-near-infrared light to enhance the hot electron generation and promote electron transfer for C-O bond cleavage during isopropanol dehydration reaction. This, in turn, results in a reduced reaction activation barrier down to 0.37 eV (compared to 1.0 eV of thermocatalysis) and a significantly improved conversion efficiency of 100% propylene from isopropanol. This work provides an additional strategy to modulate hot carrier of plasmonic semiconductors and helps guide the design of better catalytic materials and chemistries.
Topics: Humans; 2-Propanol; Dehydration; Light; Catalysis; Semiconductors
PubMed: 36379947
DOI: 10.1038/s41467-022-34738-z -
Journal of the American Chemical Society Apr 2019Tailored ruthenium(IV) complexes can catalyze the isomerization of allylic alcohols into saturated carbonyl derivatives under physiologically relevant conditions, and...
Tailored ruthenium(IV) complexes can catalyze the isomerization of allylic alcohols into saturated carbonyl derivatives under physiologically relevant conditions, and even inside living mammalian cells. The reaction, which involves ruthenium-hydride intermediates, is bioorthogonal and biocompatible, and can be used for the "in cellulo" generation of fluorescent and bioactive probes. Overall, our research reveals a novel metal-based tool for cellular intervention, and comes to further demonstrate the compatibility of organometallic mechanisms with the complex environment of cells.
Topics: Catalysis; HeLa Cells; Humans; Ketones; Molecular Structure; Oxidation-Reduction; Propanols; Ruthenium; Stereoisomerism
PubMed: 30892889
DOI: 10.1021/jacs.9b00837 -
Aesthetic Surgery Journal Sep 2021Hypochlorous acid (HA) has both anti-microbial and wound-healing properties with a growing role for utilization in pre-procedural care on the face.
BACKGROUND
Hypochlorous acid (HA) has both anti-microbial and wound-healing properties with a growing role for utilization in pre-procedural care on the face.
OBJECTIVES
The authors sought to compare the antiseptic property of 0.01% HA solution, 5% povidone iodine (PI), 4% chlorhexidine gluconate (CHG), and 70% isopropyl alcohol (IPA) antiseptic on facial skin.
METHODS
This was a prospective single-center clinical trial.
RESULTS
A total of 21 participants were recruited. Bacterial growth was seen in CHG (10%), IPA (71%), PI (81%), and HA (95%) of specimens (P < 0.001). CHG had less growth compared with HA (P = <0.001), IPA (P = <0.001), and PI (P = <0.001). No difference in bacterial growth was noted between HA and IPA (P = 0.063) or HA and PI (P = 0.25). Significant differences in mono-microbial and poly-microbial growth were seen between HA and IPA (P = 0.046) and HA and CHG (P = <0.001). Staphylococcus epidermidis grew less frequently in CHG (10%), followed by IPA (29%), PI (71%), and HA (71%). Staphylococcus capitis grew less frequently in CHG (0%), followed by PI (14%), HA (24%), and IPA (29%).
CONCLUSIONS
CHG reduced the bacterial growth compared with HA, PI, and IPA. However, HA, PI, and IPA had insignificant differences in bactericidal effects. Our study provides a supporting role of HA to be considered as an antiseptic.
Topics: 2-Propanol; Anti-Infective Agents, Local; Chlorhexidine; Dermatologic Agents; Humans; Hypochlorous Acid; Povidone-Iodine; Prospective Studies; Skin
PubMed: 33247899
DOI: 10.1093/asj/sjaa322 -
International Journal of Pharmaceutics Mar 2024Dandruff, or pityriasis capitis simplex, is a common scalp condition associated with excessive flaking and scaling of the epidermal tissue. Other features include...
Dandruff, or pityriasis capitis simplex, is a common scalp condition associated with excessive flaking and scaling of the epidermal tissue. Other features include irregular corneocyte turnover, irritation, itching and an impaired skin barrier function. Previously we reported the characterization of climbazole (CBZ), an antifungal agent used in the management of dandruff. Skin permeation of CBZ from neat solvents was also investigated. In the present work we evaluated CBZ permeation in human skin in vitro from more complex formulations that better represent products used by consumers. The various systems studied were composed of propylene glycol (PG), Transcutol®P (TC), octyl salicylate (OSal) and isopropyl alcohol (IPA). As well as measurement of skin uptake and penetration of CBZ, where possible, the skin retention and permeation of the various solvents was also determined. All vehicles promoted skin permeation of CBZ but no significant differences in amount permeated were evident between the binary vehicles (PG:TC, TC:OSal) and the ternary vehicle studied (PG:IPA:OSal). The binary vehicles generally promoted more skin uptake of CBZ compared with the neat solvents (PG, TC, OSal) studied previously. Permeation and skin extraction of CBZ from the PG:TC vehicles increased with increasing PG content; a similar trend was evident for the PG:IPA:OSal systems. New methods were developed and validated for measurement of PG, TC and OSal. Analysis of the individual solvents indicated that PG permeation was also independent of the amounts of other solvents in the binary or ternary systems. Consistent with previous findings higher proportions of TC permeated compared with PG for the PG:TC binary systems; TC also permeated the skin more rapidly than PG from these vehicles. For OSal, skin extraction was generally higher for TC:OSal compared with the PG:IPA:OSal vehicle. However, increasing the content of OSal did not appear to influence CBZ skin uptake nor permeation. Interestingly, the effects of the various PG:TC vehicles on CBZ skin delivery contrast with results we previous reported for the same systems for a different active. This confirms that with reference to skin permeation, formulation effects and/or skin penetration enhancement should be expected to vary and may not be predicted for specific vehicles.
Topics: Humans; Administration, Cutaneous; Dandruff; Skin; Solvents; Propylene Glycol; 2-Propanol; Permeability; Imidazoles
PubMed: 38331330
DOI: 10.1016/j.ijpharm.2024.123886 -
Journal of Dairy Science Jan 2021This study examined the effect of 3-nitrooxypropanol (3-NOP), an investigational substance, on enteric methane emission, milk production, and composition in Holstein...
This study examined the effect of 3-nitrooxypropanol (3-NOP), an investigational substance, on enteric methane emission, milk production, and composition in Holstein dairy cows. Following a 3-wk covariate period, 48 multi- and primiparous cows averaging (± standard deviation) 118 ± 28 d in milk, 43.4 ± 8 kg/d milk yield, and 594 ± 57 kg of body weight were blocked based on days in milk, milk yield, and enteric methane emission and randomly assigned to 1 of 2 treatment groups: (1) control, no 3-NOP, and (2) 3-NOP applied at 60 mg/kg feed dry matter. Inclusion of 3-NOP was through the total mixed ration and fed for 15 consecutive weeks. Cows were housed in a freestall barn equipped with a Calan Broadbent Feeding System (American Calan Inc., Northwood, NH) for monitoring individual dry matter intake and fed ad libitum once daily. Enteric gaseous emissions (methane, carbon dioxide, and hydrogen) were measured using 3 GreenFeed (C-Lock Inc., Rapid City, SD) units. Dry matter intake, cow body weight, and body weight change were not affected by 3-NOP. Compared with the control group, 3-NOP applied at 60 mg/kg feed dry matter decreased daily methane emission, emission yield, and emission intensity by 26, 27, and 29%, respectively. Enteric emission of carbon dioxide was not affected, and hydrogen emission was increased 6-fold by 3-NOP. Administration of 3-NOP had no effect on milk and energy-corrected milk yields and feed efficiency, increased milk fat and milk urea nitrogen concentrations, and increased milk fat yield but had no other effects on milk components. Concentration of C6:0 and C8:0 and the sum of saturated fatty acids in milk fat were increased by 3-NOP. Total trans fatty acids and the sum of polyunsaturated fatty acids were decreased by 3-NOP. In this experiment, 3-NOP decreased enteric methane daily emission, yield, and intensity without affecting dry matter intake and milk yield, but increased milk fat in high-producing dairy cows.
Topics: Animals; Cattle; Diet; Fatty Acids; Female; Gastrointestinal Tract; Lactation; Lipids; Methane; Milk; Nitrogen; Propanols
PubMed: 33131815
DOI: 10.3168/jds.2020-18908 -
Molecules (Basel, Switzerland) Jun 2021The -methoxycinnamic acid (-MCA) is one of the most studied phenylpropanoids with high importance not only in the wide spectrum of therapeutic activities but also its... (Review)
Review
The -methoxycinnamic acid (-MCA) is one of the most studied phenylpropanoids with high importance not only in the wide spectrum of therapeutic activities but also its potential application for the food industry. This natural compound derived from plants exhibits a wide range of biologically useful properties; therefore, during the last two decades it has been extensively tested for therapeutic and nutraceutical applications. This article presents the natural sources of -MCA, its metabolism, pharmacokinetic properties, and safety of its application. The possibilities of using this dietary bioactive compound as a nutraceutical agent that may be used as functional food ingredient playing a vital role in the prevention and treatment of many chronic diseases is also discussed. We present the antidiabetic, anticancer, antimicrobial, hepato-, and neuroprotective activities of -MCA and methods of its lipophilization that have been developed so far to increase its industrial application and bioavailability in the biological systems.
Topics: Anti-Infective Agents; Antineoplastic Agents; Cinnamates; Dietary Supplements; Hypoglycemic Agents; Liver; Neuroprotective Agents; Polyphenols; Propanols
PubMed: 34201697
DOI: 10.3390/molecules26133827 -
ChemistryOpen May 2020Two new families of -nucleoside analogues containing the anthracene moiety introduced through the nitrosocarbonyl ene reaction with allylic alcohols were prepared. The...
Two new families of -nucleoside analogues containing the anthracene moiety introduced through the nitrosocarbonyl ene reaction with allylic alcohols were prepared. The core structure is an isoxazolidine heterocycle that introduces either atom either a phenyl ring or dimethyl moiety at the C3 carbon. Different heterobases were inserted at the position 5 of the heterocyclic ring. One of the synthesized compounds demonstrated a good capacity to induce cell death and an appreciable nuclear fragmentation was evidenced in treated cells.
Topics: Anthracenes; Apoptosis; Humans; Models, Molecular; Molecular Structure; Nucleosides; Oxazoles; Propanols; Structure-Activity Relationship; U937 Cells
PubMed: 32373422
DOI: 10.1002/open.202000034 -
Journal of Hazardous Materials Mar 20213-Monochloropropane-1,2-diol (3-MCPD), 2,3-epoxy-1-propanol (glycidol), and their esters are well-known food contaminants mainly formed by the heat processing of certain...
3-Monochloropropane-1,2-diol (3-MCPD), 2,3-epoxy-1-propanol (glycidol), and their esters are well-known food contaminants mainly formed by the heat processing of certain refined oils and coexist in various kinds of foodstuffs. However, the combined health effect and the underlying mechanism of 3-MCPD and glycidol coexposure are not well-understood. In this study, we investigated the systemic toxicity effects and the nephrotoxicity mechanisms of 3-MCPD and glycidol coexposure with in vitro and in vivo models, and next-generation sequencing (NGS) analysis. It was found that 3-MCPD and glycidol coexposure for 28 days synergistically induced toxicity in the kidney, lung, testis, and heart in C57BL/6 mice. Kidney was the most sensitive organ to coexposure, and the coexposure had a synergistic effect on inflammation and cytotoxicity through activation of the NLRP3 inflammasome, and the induction of necroptosis, and autophagic cell death in NRK-52E cells. Moreover, the NGS results revealed the genes changes associated with nephrotoxicity, inflammation and with the broad toxicity effects induced by 3-MCPD or glycidol alone or in combination, which were consistent with the results of in vitro and in vivo models. In summary, we report for the first time of the comprehensive toxicity effects and the mechanisms caused by 3-MCPD and glycidol coexposure.
Topics: Animals; Autophagic Cell Death; Epoxy Compounds; Esters; Food Contamination; Inflammasomes; Male; Mice; Mice, Inbred C57BL; NLR Family, Pyrin Domain-Containing 3 Protein; Necroptosis; Propanols; alpha-Chlorohydrin
PubMed: 33187795
DOI: 10.1016/j.jhazmat.2020.124241 -
BMC Microbiology Feb 2021Degradation of acetone by aerobic and nitrate-reducing bacteria can proceed via carboxylation to acetoacetate and subsequent thiolytic cleavage to two acetyl residues. A...
BACKGROUND
Degradation of acetone by aerobic and nitrate-reducing bacteria can proceed via carboxylation to acetoacetate and subsequent thiolytic cleavage to two acetyl residues. A different strategy was identified in the sulfate-reducing bacterium Desulfococcus biacutus that involves formylation of acetone to 2-hydroxyisobutyryl-CoA.
RESULTS
Utilization of short-chain ketones (acetone, butanone, 2-pentanone and 3-pentanone) and isopropanol by the sulfate reducer Desulfosarcina cetonica was investigated by differential proteome analyses and enzyme assays. Two-dimensional protein gel electrophoresis indicated that D. cetonica during growth with acetone expresses enzymes homologous to those described for Desulfococcus biacutus: a thiamine diphosphate (TDP)-requiring enzyme, two subunits of a B-dependent mutase, and a NAD-dependent dehydrogenase. Total proteomics of cell-free extracts confirmed these results and identified several additional ketone-inducible proteins. Acetone is activated, most likely mediated by the TDP-dependent enzyme, to a branched-chain CoA-ester, 2-hydroxyisobutyryl-CoA. This compound is linearized to 3-hydroxybutyryl-CoA by a coenzyme B-dependent mutase followed by oxidation to acetoacetyl-CoA by a dehydrogenase. Proteomic analysis of isopropanol- and butanone-grown cells revealed the expression of a set of enzymes identical to that expressed during growth with acetone. Enzyme assays with cell-free extract of isopropanol- and butanone-grown cells support a B-dependent isomerization. After growth with 2-pentanone or 3-pentanone, similar protein patterns were observed in cell-free extracts as those found after growth with acetone.
CONCLUSIONS
According to these results, butanone and isopropanol, as well as the two pentanone isomers, are degraded by the same enzymes that are used also in acetone degradation. Our results indicate that the degradation of several short-chain ketones appears to be initiated by TDP-dependent formylation in sulfate-reducing bacteria.
Topics: 2-Propanol; Acetone; Deltaproteobacteria; Ketones; Oxidation-Reduction; Proteome; Proteomics; Sulfates
PubMed: 33593288
DOI: 10.1186/s12866-021-02112-6