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Lubbers, R. J. M., A. Dilokpimol, J. Visser i R. P. de Vries. "Aspergillus niger uses the peroxisomal CoA-dependent β-oxidative genes to degrade the hydroxycinnamic acids caffeic acid, ferulic acid, and p-coumaric acid". Applied Microbiology and Biotechnology 105, nr 10 (maj 2021): 4199–211. http://dx.doi.org/10.1007/s00253-021-11311-0.
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Abstract Aromatic compounds are important molecules which are widely applied in many industries and are mainly produced from nonrenewable sources. Renewable sources such as plant biomass are interesting alternatives for the production of aromatic compounds. Ferulic acid and p-coumaric acid, a precursor for vanillin and p-vinyl phenol, respectively, can be released from plant biomass by the fungus Aspergillus niger. The degradation of hydroxycinnamic acids such as caffeic acid, ferulic acid, and p-coumaric acid has been observed in many fungi. In A. niger, multiple metabolic pathways were suggested for the degradation of hydroxycinnamic acids. However, no genes were identified for these hydroxycinnamic acid metabolic pathways. In this study, several pathway genes were identified using whole-genome transcriptomic data of A. niger grown on different hydroxycinnamic acids. The genes are involved in the CoA-dependent β-oxidative pathway in fungi. This pathway is well known for the degradation of fatty acids, but not for hydroxycinnamic acids. However, in plants, it has been shown that hydroxycinnamic acids are degraded through this pathway. We identified genes encoding hydroxycinnamate-CoA synthase (hcsA), multifunctional β-oxidation hydratase/dehydrogenase (foxA), 3-ketoacyl CoA thiolase (katA), and four thioesterases (theA-D) of A. niger, which were highly induced by all three tested hydroxycinnamic acids. Deletion mutants revealed that these genes were indeed involved in the degradation of several hydroxycinnamic acids. In addition, foxA and theB are also involved in the degradation of fatty acids. HcsA, FoxA, and KatA contained a peroxisomal targeting signal and are therefore predicted to be localized in peroxisomes. Key points • Metabolism of hydroxycinnamic acid was investigated in Aspergillus niger • Using transcriptome data, multiple CoA-dependent β-oxidative genes were identified. • Both foxA and theB are involved in hydroxycinnamate but also fatty acid metabolism.
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Yong, Huimin, Yunpeng Liu, Dawei Yun, Shuai Zong, Changhai Jin i Jun Liu. "Chitosan Films Functionalized with Different Hydroxycinnamic Acids: Preparation, Characterization and Application for Pork Preservation". Foods 10, nr 3 (5.03.2021): 536. http://dx.doi.org/10.3390/foods10030536.
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Hydroxycinnamic acids are one category of bioactive phenolic acids that are widely distributed in plants. In this study, chitosan (CS) was functionalized with three kinds of hydroxycinnamic acids (p-coumaric acid, caffeic acid and ferulic acid) through the carbodiimide-mediated grafting method. The obtained hydroxycinnamic-acid-grafted CSs (hydroxycinnamic acid-g-CSs) were further fabricated into food packaging films through solvent casting. For the first time, the functionalities of the different hydroxycinnamic acid-g-CS films were compared. Results showed the grafting ratio of p-coumaric acid-g-CS, caffeic acid-g-CS and ferulic acid-g-CS was 73.68, 129.42 and 91.75 mg/g, respectively. Instrumental analyses confirmed hydroxycinnamic acids conjugated with CS through amide and ester bonds. The functionalization of CS film with hydroxycinnamic acids produced a more compact microstructure and higher UV light barrier ability, mechanical strength, water vapor barrier ability, thermal stability and antioxidant and antimicrobial activities. Among the different hydroxycinnamic acid-g-CS films, caffeic acid-g-CS film presented the strongest barrier, mechanical, antioxidant and antimicrobial properties. Moreover, caffeic acid-g-CS film packaging effectively extended the shelf life of pork to 10 days at 4 °C. Our results suggest caffeic acid-g-CS film can be used in the active food packaging field.
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Bento-Silva, Andreia, Noélia Duarte, Elsa Mecha, Maria Belo, Maria Carlota Vaz Patto i Maria do Rosário Bronze. "Hydroxycinnamic Acids and Their Derivatives in Broa, a Traditional Ethnic Maize Bread". Foods 9, nr 10 (15.10.2020): 1471. http://dx.doi.org/10.3390/foods9101471.
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Maize is one of the most interesting dietary sources of hydroxycinnamic acids, widely known for their beneficial health effects, namely antioxidant properties. This work aims to identify hydroxycinnamic acids and their derivatives in broa, a Portuguese traditional ethnic maize bread, and corresponding maize flours. Soluble and insoluble phenolic fractions of diverse maize flours and corresponding broas were prepared and analysed by HPLC-DAD-MS/MS (high-performance liquid chromatography coupled with diode array detector and tandem mass spectrometry). Besides free hydroxycinnamic acids, mainly ferulic and p-coumaric acids, several structural isomers and stereoisomers of insoluble ferulic acid dehydrodimers (n = 18) and trimers (n = 11), were also identified. Hydroxycinnamic acid amides consisting of coumaroyl and feruloyl conjugates (n = 22) were present in both soluble and insoluble fractions of maize flours and breads, in different isomeric forms. A new compound was putatively identified as bis-N,N′-diferuloyl putrescine. Additionally, more complex and insoluble hydroxycinnamic acid amides, derived from ferulic acid dehydrodimers (n = 47) and trimers (n = 18), were also putatively identified for the first time, suggesting that hydroxycinnamic acid amides are also linked to maize cell walls. Since hydroxycinnamic derivatives were not only identified in maize flours, but also in broas, they can contribute to the antioxidant properties and beneficial health effects of maize-based foods.
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Filannino, Pasquale, Marco Gobbetti, Maria De Angelis i Raffaella Di Cagno. "Hydroxycinnamic Acids Used as External Acceptors of Electrons: an Energetic Advantage for Strictly Heterofermentative Lactic Acid Bacteria". Applied and Environmental Microbiology 80, nr 24 (26.09.2014): 7574–82. http://dx.doi.org/10.1128/aem.02413-14.
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ABSTRACTThe metabolism of hydroxycinnamic acids by strictly heterofermentative lactic acid bacteria (19 strains) was investigated as a potential alternative energy route.Lactobacillus curvatusPE5 was the most tolerant to hydroxycinnamic acids, followed by strains ofWeissellaspp.,Lactobacillus brevis,Lactobacillus fermentum, andLeuconostoc mesenteroides, for which the MIC values were the same. The highest sensitivity was found forLactobacillus rossiaestrains. During growth in MRS broth, lactic acid bacteria reduced caffeic,p-coumaric, and ferulic acids into dihydrocaffeic, phloretic, and dihydroferulic acids, respectively, or decarboxylated hydroxycinnamic acids into the corresponding vinyl derivatives and then reduced the latter compounds to ethyl compounds. Reductase activities mainly emerged, and the activities of selected strains were further investigated in chemically defined basal medium (CDM) under anaerobic conditions. The end products of carbon metabolism were quantified, as were the levels of intracellular ATP and the NAD+/NADH ratio. Electron and carbon balances and theoretical ATP/glucose yields were also estimated. When CDM was supplemented with hydroxycinnamic acids, the synthesis of ethanol decreased and the concentration of acetic acid increased. The levels of these metabolites reflected on the alcohol dehydrogenase and acetate kinase activities. Overall, some biochemical traits distinguished the common metabolism of strictly heterofermentative strains: main reductase activity toward hydroxycinnamic acids, a shift from alcohol dehydrogenase to acetate kinase activities, an increase in the NAD+/NADH ratio, and the accumulation of supplementary intracellular ATP. Taken together, the above-described metabolic responses suggest that strictly heterofermentative lactic acid bacteria mainly use hydroxycinnamic acids as external acceptors of electrons.
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Bichot, Lerosty, Geirnaert, Méchin, Carrère, Bernet, Delgenès i García-Bernet. "Soft Microwave Pretreatment to Extract P-Hydroxycinnamic Acids from Grass Stalks". Molecules 24, nr 21 (28.10.2019): 3885. http://dx.doi.org/10.3390/molecules24213885.
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The aim of this article is to provide an analysis of microwave effects on ferulic and coumaric acids (FA and CA, respectively) extraction from grass biomass (corn stalks and miscanthus). Microwave pretreatment using various solvents was first compared to conventional heating on corn stalks. Then, microwave operational conditions were extended in terms of incident power and treatment duration. Optimal conditions were chosen to increase p-hydroxycinnamic acids release. Finally, these optimal conditions determined on corn stalks were tested on miscanthus stalks to underlie the substrate incidence on p-hydroxycinnamic acids release yields. The optimal conditions—a treatment duration of 405 s under 1000 W—allowed extracting 1.38% FA and 1.97% CA in corn stalks and 0.58% FA and 3.89% CA in miscanthus stalks. The different bioaccessibility of these two molecules can explain the higher or lower yields between corn and miscanthus stalks.
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Sun, Wenli, i Mohamad Hesam Shahrajabian. "Therapeutic Potential of Phenolic Compounds in Medicinal Plants—Natural Health Products for Human Health". Molecules 28, nr 4 (15.02.2023): 1845. http://dx.doi.org/10.3390/molecules28041845.
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Phenolic compounds and flavonoids are potential substitutes for bioactive agents in pharmaceutical and medicinal sections to promote human health and prevent and cure different diseases. The most common flavonoids found in nature are anthocyanins, flavones, flavanones, flavonols, flavanonols, isoflavones, and other sub-classes. The impacts of plant flavonoids and other phenolics on human health promoting and diseases curing and preventing are antioxidant effects, antibacterial impacts, cardioprotective effects, anticancer impacts, immune system promoting, anti-inflammatory effects, and skin protective effects from UV radiation. This work aims to provide an overview of phenolic compounds and flavonoids as potential and important sources of pharmaceutical and medical application according to recently published studies, as well as some interesting directions for future research. The keyword searches for flavonoids, phenolics, isoflavones, tannins, coumarins, lignans, quinones, xanthones, curcuminoids, stilbenes, cucurmin, phenylethanoids, and secoiridoids medicinal plant were performed by using Web of Science, Scopus, Google scholar, and PubMed. Phenolic acids contain a carboxylic acid group in addition to the basic phenolic structure and are mainly divided into hydroxybenzoic and hydroxycinnamic acids. Hydroxybenzoic acids are based on a C6-C1 skeleton and are often found bound to small organic acids, glycosyl moieties, or cell structural components. Common hydroxybenzoic acids include gallic, syringic, protocatechuic, p-hydroxybenzoic, vanillic, gentistic, and salicylic acids. Hydroxycinnamic acids are based on a C6-C3 skeleton and are also often bound to other molecules such as quinic acid and glucose. The main hydroxycinnamic acids are caffeic, p-coumaric, ferulic, and sinapic acids.
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Bento-Silva, Andreia, Noélia Duarte, Elsa Mecha, Maria Belo, Ana Teresa Serra, Maria Carlota Vaz Patto i Maria Rosário Bronze. "Broa, an Ethnic Maize Bread, as a Source of Phenolic Compounds". Antioxidants 10, nr 5 (26.04.2021): 672. http://dx.doi.org/10.3390/antiox10050672.
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Maize is an important source of phenolic compounds, specially hydroxycinnamic acids, which are widely known for their antioxidant activity and associated health benefits. However, these effects depend on their bioaccessibility, which is influenced by the different techniques used for food processing. Several traditional products can be obtained from maize and, in Portugal, it is used for the production of an ethnic bread called broa. In order to evaluate the effect of processing on maize phenolic composition, one commercial hybrid and five open-pollinated maize flours and broas were studied. The total phenolic content and antioxidant activity were evaluated by the Folin-Ciocalteu and ORAC assays, respectively. The major phenolics, namely ferulic and p-coumaric acids (in their soluble-free, soluble-conjugated and insoluble forms), insoluble ferulic acid dimers and soluble hydroxycinnamic acid amides were quantitated. Results show that the total phenolic content, antioxidant activity and hydroxycinnamic acids resisted traditional processing conditions used in the production of broas. The content in soluble-free phenolics increased after processing, meaning that their bioaccessibility improved. Portuguese traditional broas, produced with open-pollinated maize varieties, can be considered an interesting dietary source of antioxidant compounds due to the higher content in hydroxycinnamic acids and derivatives.
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Kotsupii, Olga Viktorovna, i Tatyana Aleksandrovna Shemetova. "FEATURES OF ACCUMULATION OF PHENOLIC COMPOUNDS IN ENDEMIC SPECIES ASTRAGALUS IONAE PALIBIN AND A. PALIBINII POLOZHIJ GROWING ON THE TERRITORY OF THE REPUBLIC OF KHAKASIA". chemistry of plant raw material, nr 2 (23.05.2024): First. http://dx.doi.org/10.14258/jcprm.20240212441.
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The features of the accumulation of flavonoid glycosides and hydroxybenzoic and hydroxycinnamic acids have been studied in the leaves of endemic Astragalus ionae Palibin and A. palibinii Polozhij of different ecological and geographical growing conditions of the Republic of Khakasia by HPLC method. Luteolin-7-glucoside, rutin, kaempferol-3-O-β-rutinoside, and 3 quercetin glycosides were identified from 8 glycosides of flavonoids from the leaves of A. ionae plants. Six flavonoid glycosides were found in the leaves of A. palibinii, luteolin-7-glucoside, rutin, kaempferol-3-O-β-rutinoside, and isorhamnetin-3-O-β-rutinoside were identified. No differences were found in the composition of hydroxybenzoic and hydroxycinnamic acids in plants of the studied taxa. Gallic, p-hydroxybenzoic, neochlorogenic, chlorogenic, caffeic, p-coumaric, and ferulic acids were identified in the leaves of A. ionae and A. palibinii. The differences between these species in terms of the content of phenolic compounds are most pronounced in the fact that A. ionae plants accumulate more luteolin-7-glucoside, the sum of flavonoid glycosides, and hydroxybenzoic acids. The content of phenolic compounds in plants of different coenopopulations is influenced by ecological and coenotic factors. In arid xerophytic and petrophytic communities more characteristic of these species, more caffeic acid and rutin accumulate, as well as the amount of hydroxycinnamic acids.
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van Beek, Sylvie, i Fergus G. Priest. "Decarboxylation of Substituted Cinnamic Acids by Lactic Acid Bacteria Isolated during Malt Whisky Fermentation". Applied and Environmental Microbiology 66, nr 12 (1.12.2000): 5322–28. http://dx.doi.org/10.1128/aem.66.12.5322-5328.2000.
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ABSTRACT Seven strains of Lactobacillus isolated from malt whisky fermentations and representing Lactobacillus brevis,L. crispatus, L. fermentum, L. hilgardii, L. paracasei, L. pentosus, andL. plantarum contained genes for hydroxycinnamic acid (p-coumaric acid) decarboxylase. With the exception ofL. hilgardii, these bacteria decarboxylatedp-coumaric acid and/or ferulic acid, with the production of 4-vinylphenol and/or 4-vinylguaiacol, respectively, although the relative activities on the two substrates varied between strains. The addition of p-coumaric acid or ferulic acid to cultures ofL. pentosus in MRS broth induced hydroxycinnamic acid decarboxylase mRNA within 5 min, and the gene was also induced by the indigenous components of malt wort. In a simulated distillery fermentation, a mixed culture of L. crispatus and L. pentosus in the presence of Saccharomyces cerevisiae decarboxylated added p-coumaric acid more rapidly than the yeast alone but had little activity on added ferulic acid. Moreover, we were able to demonstrate the induction of hydroxycinnamic acid decarboxylase mRNA under these conditions. However, in fermentations with no additional hydroxycinnamic acid, the bacteria lowered the final concentration of 4-vinylphenol in the fermented wort compared to the level seen in a pure-yeast fermentation. It seems likely that the combined activities of bacteria and yeast decarboxylate p-coumaric acid and then reduce 4-vinylphenol to 4-ethylphenol more effectively than either microorganism alone in pure cultures. Although we have shown that lactobacilli participate in the metabolism of phenolic compounds during malt whisky fermentations, the net result is a reduction in the concentrations of 4-vinylphenol and 4-vinylguaiacol prior to distillation.
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Bergvinson, D. J., J. T. Arnason i L. N. Pietrzak. "Localization and quantification of cell wall phenolics in European corn borer resistant and susceptible maize inbreds". Canadian Journal of Botany 72, nr 9 (1.09.1994): 1243–49. http://dx.doi.org/10.1139/b94-152.
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Three maize inbreds (MBR 6796-15, B86, and CI31A) resistant to leaf feeding by the European corn borer Ostrinia nubilalis, and one susceptible inbred (MS72), were evaluated for insect resistance and phytochemical composition to gain a better understanding of maize-resistance mechanisms. Insect resistance was evaluated using laboratory bioassays that demonstrated that immature leaf tissue is the preferred feeding substrate. Phytochemical analyses were conducted for leaf protein, hydroxamic acid content, and hydroxycinnamic acids bound to the cell wall for both immature and mature leaf tissue. Hydroxycinnamic acid distribution in cell walls was examined using five stains, autofluorescence, and microspectrophotometry. Phloroglucinol, azure B, diazotized salts of p-nitroaniline and sulfanilic acid, and chlorine sulfite allowed visualization of phenolic localization but were not quantitative. Microspectrophotometer readings of epidermal, phloem, and xylem cell walls confirmed staining results, showing extremely low cell wall hydroxycinnamic acid levels in epidermal cell walls of immature leaf tissue. Foliar nitrogen content was not related to insect feeding preference. Hydroxycinnamic acid fortification of epidermal cell walls appears to correlate best with corn borer feeding preference, accounting for differential resistance between inbred lines and between tissue maturities. Microspectrophotometry may be useful as a technique for monitoring phytochemical resistance mechanisms in breeding programs. Key words: maize, Ostrinia nubilalis, phenolic, hydroxycinnamic acids, cell wall, microspectrophotometry, resistance.
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Kotsupiy, Olga, i Tatyana Shemetova. "Phenolic profiles of the endemic species Astragalus palibinii Polozhij". BIO Web of Conferences 38 (2021): 00063. http://dx.doi.org/10.1051/bioconf/20213800063.
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For the first time, the composition and content of phenolic compounds (PC) of plant leaves of an endemic rare species of the Xiphidium Bunge section of the genus Astragalus L. of Siberia – Astragalus palibinii Polozhij was studied by HPLC. 11 compounds of phenolic nature were identified in water-ethanol extracts of A. palibinii leaves: gallic, p-hydroxybenzoic, chlorogenic, caffeic, ferulic, trans-ferulic, cinnamic acids, isoquercitrin, rutin, isoramnetin-3-O-rutinoside and L-epicatechin. The composition of PC in the leaves of plants of three cenopopulations A. palibinii from Khakassia is the same, with the exception of one hydroxycinnamic acid in trace amounts. The content (mg per 100 g DW) of flavonol glycosides in the leaves of A. palibinii plants varies in the range of 0.442–0.907, the content of hydroxycinnamic and hydroxybenzoic acids in the range of 98.5–109.7 and 32.5–83.9, respectively. The quantitative profiles of all the studied groups of PC are characterized by significant variability in the content of individual components. The variability of the content of hydroxycinnamic acids, flavonoids and hydroxybenzoic acids was determined as very low, medium and increased, respectively.
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Lampíř, L. "Varietal differentiation of white wines on the basis of phenolic compounds profile". Czech Journal of Food Sciences 31, No. 2 (18.04.2013): 172–79. http://dx.doi.org/10.17221/270/2012-cjfs.
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The authenticity of grapevine varieties is a very important topic in the Czech Republic, where varietal wines is very important for wine drinkers. The wines from 7 grapevine varieties were investigated. Sixteen phenolic compounds belonging among hydroxybenzoic and hydroxycinnamic acids, stilbenes, and flavan-3-ols were analysed by HPLC method. The aim of this study was to find markers of varietal origin of wines among the phenolic compounds studied. The analytical parameters obtained were evaluated for this purpose by CVA (canonical varietal analysis) method. It proved to be successful in detecting the following grapevine variety authenticity markers: hydroxycinnamic acids (i.e. p-coutaric acid and caftaric acid), hydroxybenzoic acids (protocatechuic acid and syringic acid), and flavan-3-ols <br />((–)-epicatechin and (+)-catechin).
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Karimov, O. K., G. Y. Kolchina, G. A. Teptereva, I. A. Chetvertneva, E. K. Karimov i A. R. Badretdinov. "The reactivity of cinnamic acid derivatives as lignin precursors". Fine Chemical Technologies 15, nr 4 (12.09.2020): 7–13. http://dx.doi.org/10.32362/2410-6593-2020-15-4-7-13.
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Objectives. Cinnamic acid derivatives belong to a large class of phenolic compounds, which are widely distributed in plants and have high potential for use in the medical and industrial fields. They have various useful practical properties, e.g., antioxidant, anti-inflammatory, antiplatelet, and anti-melanogenic properties. Hydroxycinnamic acids are of particular interest as phenylpropanoids, which are the starting compounds of lignin. The aim of this work was to study the electronic structure and analyze the reactivity of the simplest representatives of phenylpropanoids formed during the biosynthesis of the coumaric (p-hydroxycinnamic), caffeic (3,4-dihydroxycinnamic), ferulic (3-methoxy-4-hydroxycinnamic), sinapic (3,5-dimethoxy-4- hydroxycinnamic), and 3,4-dimethoxycinnamic acids. These acids are the biogenetic precursors of most other phenolic compounds (coumarins, melanins, lignins, and flavonoids) and are found in almost all higher plants.Methods. Calculations with full optimization of the geometric parameters were performed using the original Hartree–Fock theory and hybrid density functional method. All calculations were performed using the Firefly program. Results. A comparative quantum chemical calculation of the geometric parameters of hydroxycinnamic acid molecules was conducted via two methods, and the values of the charges on atoms according to Mulliken were determined. It was found that with the addition of hydroxyl and methoxy substituents at the meta and para positions relative to the carboxyl fragment, the electron density shifts toward the benzene ring, and the symmetry of the molecule decreases. Additionally, in these structures, there is π,π-conjugation of the carboxyl fragment of the –СН=СНСООН molecule with the aromatic ring, which significantly affects the geometric configuration of the molecule. The maximum positive charge is concentrated on the C9 atom, while the maximum negative charge is on the oxygen atoms belonging to the methoxy substituents and the hydroxyl group, which confirms the role of oxygen atoms in the chemical transformations of acids. Conclusions. Two different methods were used to calculate the geometric, electronic, and energy parameters and electrophilicity indices of the studied hydroxycinnamic acids in the gas phase. The obtained values were consistent (within the limits of error) with the experimental data as well as the results described in earlier works’ calculations by other methods.
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Kumar, Ch Ravi S., Anjali Jha i Sri Deepthi. "DFT Studies of Distinct Anilines with p-Hydroxycinnamic Acids for Antioxidant Profile". Medicinal Chemistry 17, nr 1 (29.12.2020): 60–70. http://dx.doi.org/10.2174/1573406416666200506085152.
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Background: Life style and jobs in current situations have generated increased free radicals such as hydroxyl (OH•) and superoxide (O2•) radicals, thereby increasing stress in humans. Interest in search of antioxidants that trap these free radicals has increased to relieve stress. β-carotene (provitamin A), ascorbic acid (vitamin C), tocopherol or vitamin E, Trolox; butyl hydroxy toluene and phenolic compounds are the well-known antioxidants. Several methods evaluate the antioxidant property existing in natural substances (medicinal plants and agri-food products) and synthetic compounds (2-methyl-3- (pyrrolidin-2-ylideneamino) quinazolin-4 (3H) –one and 3,3'- (1,4- phenylenebis (methanylylidene)) bis (azanylylidene) (2-methyl-quinazolin-4 (3H) -one). Objective: The objective of this study is to focus on complexes with p-hydroxycinnamic acids to trap free radicals in a greener way. Method: Spectroscopic shifts and structural studies were employed to attribute electronic properties responsible for antioxidant profile. Spectroscopic shifts in wavenumbers were attributed with Fourier Transform Infrared Spectra (FTIR) and Fourier Transform Raman spectra (FT Raman Spectra). Structural studies were performed with Gaussian package, electron density method the B3LYP method, basis set 6-31(d) for attributing electronic properties responsible for antioxidant profile. Result: Interpretation of FTIR spectra revealed spectroscopic shifts in wavenumbers in all the complexes responsible for bonding. Further, studies confirmed the formation of complex with reduced intensities in Raman spectra. Computational studies revealed enhancement in molecular and electronic properties responsible for antioxidant power. Conclusion: Studies revealed that complex with p-nitroaniline contribute to greater acceptor and donor power responsible for antioxidant power. These higher powers suggest the best antiradicals to trap free radicals.
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Camarero, Susana, Ana I. CaÑas, Paula Nousiainen, Eric Record, Anne Lomascolo, MarÍa JesÚs MartÍnez i Ángel T. MartÍnez. "p-Hydroxycinnamic Acids as Natural Mediators for Laccase Oxidation of Recalcitrant Compounds". Environmental Science & Technology 42, nr 17 (wrzesień 2008): 6703–9. http://dx.doi.org/10.1021/es8008979.
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Caparica, Rita, André Rolim Baby, Tânia Almeida i João Guilherme Costa. "In vitro cytotoxicity assessment of ferulic, caffeic and p-coumaric acids on human renal cancer cells". Biomedical and Biopharmaceutical Research Journal 17, nr 1 (marzec 2020): 1–12. http://dx.doi.org/10.19277/bbr.17.1.225.
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Bioactive compounds from natural sources have been extensively studied as potential therapeutic agents, due to their chemical, structural, and biological properties. Among them, hydroxycinnamic acids emerge with a very interesting pharmacological potential to prevent and treat several diseases, including cancer. However, while some studies support their anticancer activity, other reports indicate otherwise. Since the impact of these compounds on renal cancer is not well established, further studies are needed to better understand their biological effects and their potential therapeutic uses in this cancer. In this work, the cytotoxicity of three hydroxycinnamic acids: ferulic, caffeic and p-coumaric acids, was evaluated on 786-O human renal cancer cells by MTT and CV assays. At concentrations up to 250 µM, none of the studied natural compounds showed cytotoxic effects to 786-O cell line. At higher concentrations (500 and 1000 µM), while ferulic acid also did not significantly influence the cell viability of 786-O cells, p-coumaric and caffeic acids decreased the renal cancer cells viability. Nevertheless, further studies on the biological activity of these compounds, using other methodologies, as well as using other cancer cell models, should be performed.
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Júlio, Ana, Nádia Remtula, Marisa Nicolai i Tânia Santos de Almeida. "Ionic liquids as tools to improve gel formulations containing sparingly soluble phenolic acids". Journal Biomedical and Biopharmaceutical Research 19, nr 1 (czerwiec 2022): 1–15. http://dx.doi.org/10.19277/bbr.19.1.280.
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Hydroxycinnamic acids, namely caffeic and p-coumaric acids, have several pharmaceutical and cosmetic applications, but due to their low aqueous solubility, their applicability can be limited. Ionic liquids (ILs) have been shown to be a valuable tool to improve the solubility and assist in the incorporation of various phenolic compounds into delivery systems. Thus, this work aims to evaluate the impact of incorporating three choline-based ILs, namely (2-hydroxyethyl)-trimethylammonium-L-phenylalanine [Cho][Phe], (2-hydroxyethyl)-trimethylammonium-L-glutamate [Cho][Glu] and (2-hydroxyethyl)-trimethylammonium-glycinate [Cho][Gly], into an aqueous gel formulation containing the poorly soluble caffeic and p-coumaric acids. The results obtained confirm that the ILs not only increase the drug solubility, but also allow higher amounts of both studied drugs to be incorporated into the gels, without interfering with the stability of the aqueous gels. Moreover, the ILs altered the fluidity of the gels, both in the absence and presence of both phenolic acids, as they increase the viscosity of the formulations, contributing to higher flow resistance of the gel, which may be better accepted by the consumer. Keywords: Ionic liquids; Hydroxycinnamic acids; Poorly soluble drugs; Gels; Increased Viscosity
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Konovalova, Olena, Tetiana Omelkovets, Iryna Hurtovenko, Natalia Sydora, Mariia Kalista i Olha Shcherbakova. "Investigation of the polyphenol composition of red oak (Quercus rubra L.) raw materials". ScienceRise: Pharmaceutical Science, nr 2(42) (30.04.2023): 75–81. http://dx.doi.org/10.15587/2519-4852.2023.277969.
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The aim of the work was to determine the main groups of polyphenolic compounds in Quercus rubra L. raw materials.
Materials and methods. The leaves and annual shoots of Northern Red Oak used for research were collected in August in Lisnyky village of Obuhiv district of Kyiv Oblast (Ukraine). Determination of the component composition and quantitative content of flavonoids (including separately catechins), hydroxycinnamic acids, and phenolic acids were carried out in the samples of air-shade-dried crushed raw material to a particle size of 3 mm by the method of high-performance liquid chromatography (HPLC). Agilent Technologies 1200 liquid chromatograph was used for liquid chromatography.Results. Using the HPLC method, 18 polyphenolic compounds were identified in leaves and annual shoots of Northern Red Oak, in particular, flavonoids: rutin, quercetin-3-β-glucoside, luteolin, neohesperidin; catechins: catechin, epicatechin, epicatechin gallate, gallocatechin; hydroxycinnamic acids: chlorogenic, caffeic, trans-ferulic, trans-cinnamic, p-coumaric, hydroxyphenylacetic, benzoic, syringic, sinapic acids; phenolic acid is gallic acid. The dominant component among flavonoids is rutin (323.43 mg/100 g) (in the composition of catechins, epicatechin gallate (25.45 mg/100 g) prevails); among hydroxycinnamic acids in Northern Red Oak raw materials, chlorogenic acid (139.62 mg/100 g) and sinapic acid (74.64 mg/100 g) prevail.Conclusions. The obtained results point to the prospects of further phytochemical and pharmacological studies of Quercus rubra raw materials, with the aim of creating new plant substances based on it with antioxidant, anti-inflammatory, and antiviral activity
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Cao, Ana, Lana M. Reid, Ana Butrón, Rosa Ana Malvar, Xose C. Souto i Rogelio Santiago. "Role of Hydroxycinnamic Acids in the Infection of Maize Silks by Fusarium graminearum Schwabe". Molecular Plant-Microbe Interactions® 24, nr 9 (wrzesień 2011): 1020–26. http://dx.doi.org/10.1094/mpmi-03-11-0079.
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In the current study, the hydroxycinnamic acids in silks of diverse maize inbred lines differing in Fusarium resistance were determined at several times after inoculation with Fusarium graminearum or sterile water as control. The main objective was to determine the possible relationship between the hydroxycinnamic acid changes in silks and ear rot resistance. Several changes in the cell-wall-bound hydroxycinnamic acid concentrations were observed after inoculation with F. graminearum, although these changes were not directly correlated with genotypic resistance to this fungus. Ester-bound ferulic acid decreased, probably due to degradation of hemicellulose by hydrolytic enzymes produced by Fusarium spp., while p-coumaric acid and diferulates showed slight increases that, in conjunction, did not result in delayed F. graminearum progression through the silks. It is important to note that the decrease of ferulic acid in the F. graminearum treatment was faster in susceptible than in resistant genotypes, suggesting a differential hemicellulose degradation in silk tissues. Therefore, the ability of the maize genotypes to slow down that process through hemicellulose structural features or xylanase inhibitors needs to be addressed in future studies.
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Wang, Zi-Ying, Ying Yin, Dong-Ni Li, Dan-Yue Zhao i Jun-Qing Huang. "Biological Activities of p-Hydroxycinnamic Acids in Maintaining Gut Barrier Integrity and Function". Foods 12, nr 13 (7.07.2023): 2636. http://dx.doi.org/10.3390/foods12132636.
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It is well established that p-Hydroxycinnamic acids (HCAs), including ferulic, caffeic, sinapic, and p-coumaric acids, possess a characteristic phenylpropanoid C6-C3 backbone and account for about one-third of the phenolic compounds in our diet. HCAs are typically associated with various plant cell wall components, including mono-, di-, and polysaccharides, sterols, polyamines, glycoproteins, and lignins. Interestingly, enzymes produced by intestinal microbes liberate HCAs from these associations. HCAs are completely absorbed in their free form upon ingestion and undergo specific reactions upon absorption in the small intestine or liver. The gut epithelium, composed of intestinal epithelial cells (IECs), acts as a physical barrier against harmful bacteria and a site for regulated interactions between bacteria and the gut lumen. Thus, maintaining the integrity of the epithelial barrier is essential for establishing a physiochemical environment conducive to homeostasis. This review summarizes the protective effects of HCAs on the intestinal barrier, achieved through four mechanisms: preserving tight junction proteins (TJPs), modulating pro-inflammatory cytokines, exerting antioxidant activity, and regulating the intestinal microbiota.
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Meyer, Thibault, Sébastien Renoud, Armelle Vigouroux, Aurélie Miomandre, Vincent Gaillard, Isabelle Kerzaon, Claire Prigent-Combaret i in. "Regulation of Hydroxycinnamic Acid Degradation Drives Agrobacterium fabrum Lifestyles". Molecular Plant-Microbe Interactions® 31, nr 8 (sierpień 2018): 814–22. http://dx.doi.org/10.1094/mpmi-10-17-0236-r.
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Regulatory factors are key components for the transition between different lifestyles to ensure rapid and appropriate gene expression upon perceiving environmental cues. Agrobacterium fabrum C58 (formerly called A. tumefaciens C58) has two contrasting lifestyles: it can interact with plants as either a rhizosphere inhabitant (rhizospheric lifestyle) or a pathogen that creates its own ecological niche in a plant tumor via its tumor-inducing plasmid (pathogenic lifestyle). Hydroxycinnamic acids are known to play an important role in the pathogenic lifestyle of Agrobacterium spp. but can be degraded in A. fabrum species. We investigated the molecular and ecological mechanisms involved in the regulation of A. fabrum species-specific genes responsible for hydroxycinnamic acid degradation. We characterized the effectors (feruloyl-CoA and p-coumaroyl-CoA) and the DNA targets of the MarR transcriptional repressor, which we named HcaR, which regulates hydroxycinnamic acid degradation. Using an hcaR-deleted strain, we further revealed that hydroxycinnamic acid degradation interfere with virulence gene expression. The HcaR deletion mutant shows a contrasting competitive colonization ability, being less abundant than the wild-type strain in tumors but more abundant in the rhizosphere. This supports the view that A. fabrum C58 HcaR regulation through ferulic and p-coumaric acid perception is important for the transition between lifestyles.
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Medeiros, Jacob, Shufen Xu, Gary J. Pickering i Belinda S. Kemp. "Influence of Caffeic and Caftaric Acid, Fructose, and Storage Temperature on Furan Derivatives in Base Wine". Molecules 27, nr 22 (15.11.2022): 7891. http://dx.doi.org/10.3390/molecules27227891.
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The aim of this study was to determine the influence of caffeic and caftaric acid, fructose, and storage temperature on the formation of furan-derived compounds during storage of base wines. Base wines produced from Chardonnay grapes were stored at 15 and 30 °C for 90 days with additions of fructose, caffeic acid, and caftaric acid independently or in combinations. Wines were analyzed following 90 days of storage for: total hydroxycinnamic acids, degree of browning, caffeic acid and caftaric acid concentrations, and nine furan-derived compounds. Caffeic and caftaric acid additions increased homofuraneol concentration by 31% and 39%, respectively, at 15 °C (p < 0.05). Only the addition of caffeic acid increased furfural by 15% at 15 °C (p < 0.05). Results demonstrate that some furan derivatives over 90 days at 15 °C increased slightly with 5 mg/L additions of caffeic and caftaric acid. This is the first time the influence of hydroxycinnamic acids on furan-derived compounds has been reported during short-term aging of base wine at cellar temperature.
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Peyrot, Cédric, Aurélien A. M. Peru, Louis M. M. Mouterde i Florent Allais. "Proline-Mediated Knoevenagel–Doebner Condensation in Ethanol: A Sustainable Access to p-Hydroxycinnamic Acids". ACS Sustainable Chemistry & Engineering 7, nr 10 (18.04.2019): 9422–27. http://dx.doi.org/10.1021/acssuschemeng.9b00624.
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Mkabayi, Lithalethu, Samkelo Malgas, Brendan S. Wilhelmi i Brett I. Pletschke. "Evaluating Feruloyl Esterase—Xylanase Synergism for Hydroxycinnamic Acid and Xylo-Oligosaccharide Production from Untreated, Hydrothermally Pre-Treated and Dilute-Acid Pre-Treated Corn Cobs". Agronomy 10, nr 5 (13.05.2020): 688. http://dx.doi.org/10.3390/agronomy10050688.
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Agricultural residues are considered the most promising option as a renewable feedstock for biofuel and high valued-added chemical production due to their availability and low cost. The efficient enzymatic hydrolysis of agricultural residues into value-added products such as sugars and hydroxycinnamic acids is a challenge because of the recalcitrant properties of the native biomass. Development of synergistic enzyme cocktails is required to overcome biomass residue recalcitrance, and achieve high yields of potential value-added products. In this study, the synergistic action of two termite metagenome-derived feruloyl esterases (FAE5 and FAE6), and an endo-xylanase (Xyn11) from Thermomyces lanuginosus, was optimized using 0.5% (w/v) insoluble wheat arabinoxylan (a model substrate) and then applied to 1% (w/v) corn cobs for the efficient production of xylo-oligosaccharides (XOS) and hydroxycinnamic acids. The enzyme combination of 66% Xyn11 and 33% FAE5 or FAE6 (protein loading) produced the highest amounts of XOS, ferulic acid, and p-coumaric acid from untreated, hydrothermal, and acid pre-treated corn cobs. The combination of 66% Xyn11 and 33% FAE6 displayed an improvement in reducing sugars of approximately 1.9-fold and 3.4-fold for hydrothermal and acid pre-treated corn cobs (compared to Xyn11 alone), respectively. The hydrolysis product profiles revealed that xylobiose was the dominant XOS produced from untreated and pre-treated corn cobs. These results demonstrated that the efficient production of hydroxycinnamic acids and XOS from agricultural residues for industrial applications can be achieved through the synergistic action of FAE5 or FAE6 and Xyn11.
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Felgines, Catherine, Didier Fraisse, Catherine Besson, Marie-Paule Vasson i Odile Texier. "Bioavailability of lemon verbena (Aloysia triphylla) polyphenols in rats: impact of colonic inflammation". British Journal of Nutrition 111, nr 10 (11.02.2014): 1773–81. http://dx.doi.org/10.1017/s0007114514000026.
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Lemon verbena (Aloysia triphylla) infusion, a widely consumed herbal tea, contains significant amounts of polyphenols such as flavone diglucuronides and phenylpropanoid glycosides (mainly verbascoside). We have recently shown that lemon verbena infusion offers beneficial effects against dextran sodium sulphate (DSS)-induced colonic inflammation in rats. The present study aimed to evaluate the bioavailability and intestinal absorption of polyphenols derived from lemon verbena infusion in both healthy and colitic rats. For this purpose, lemon verbena infusion was given to rats ad libitum for 14 d, and then 4 % DSS was added to the infusion for 7 d. Before and after DSS administration, 24 h urinary excretion of polyphenols was determined. Flavones were excreted in the urine as conjugated aglycones, and their excretion was not significantly altered by colonic inflammation. Only trace amounts of verbascoside were excreted in the urine, but various metabolites (hydroxycinnamic acids) were detected. The urinary excretion of hydroxycinnamic acids, particularly that of caffeic acid, increased after DSS administration (P< 0·05). Only flavone aglycones (luteolin and diosmetin) were excreted in the faeces in small proportions (3·2 % of ingested flavones). Intestinal absorption of lemon verbena polyphenols was examined using an in situ intestinal perfusion model. Intestinal absorption of verbascoside and flavone diglucuronides did not significantly differ between the healthy and colitic rats. Collectively, these results show that intestinal absorption and urinary excretion of lemon verbena flavone diglucuronides were not altered by colonic inflammation, but that urinary excretion of hydroxycinnamic acids derived from verbascoside was affected in a colitic situation.
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Boegge, Sabine C., Adolf Nahrstedt, Michael Linscheid i Walter Nigge. "Distribution and Stereochemistry of Hydroxycinnamoylmalic Acids and of Free Malic Acids in Papaveraceae and Fumariaceae". Zeitschrift für Naturforschung C 50, nr 9-10 (1.10.1995): 608–15. http://dx.doi.org/10.1515/znc-1995-9-1003.
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Abstract The distribution of hydroxycinnamoylmalic acids (HCM acids) in 25 species and 2 subspecies of Papaveraceae and Fumariaceae representing 14 genera was investigated by HPLC and subsequent diode array detection (DAD). In case of similar chromatographic and UV-spectrometric behavior of HCM acids and other hydroxycinnamic acid derivatives liquid chromatography-thermospray/mass spectrometry (LC-TSP/MS) was used for positive identification. Ten of the species were found to contain caffeoyl-, p-coumaroyl-. and feruloylmalic acid whereas Chelidonium majus only showed the presence of caffeoylmalic acid. Sinapoylmalic acid could not be detected. The quantitative determ ination by HPLC at 330 nm yielded the highest content of caffeoylmalic acid for Fumciria officinalis and F. capreolata, and the lowest for Chelidonium majus. Isolated HCM acids showed positive optical rotation for members of the Papaveraceae and negative values for m em bers of the Fum ariaceae. This points to an esterification of hydroxycinnam ic acids with (-)-ʟ -malic acid for the Papaveraceae and with (+)-ᴅ-malic acid for the Fumariaceae. For plants containing HCM acids the contents of free l - and ᴅ-malic acid w ere determ ined enzym atically Yields of ʟ-malic acid were higher for Papaveraceae than for Fum ariaceae; ᴅ-malic acid was detectable only in traces for all investigated species. The Fum ariaceae showed a ca. 1:1 relationship between free ʟ-malate and esterified ᴅ-malate. This suggests an enzym atic racem ization of the original ʟ-malate and a subsequent esterification of the intermediate ᴅ-malate with hydroxycinnamic acids
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Ramphinwa, Maanea L., Godwin R. A. Mchau, Ntakadzeni E. Madala, Ndamulelo Nengovhela, John B. O. Ogola i Fhatuwani N. Mudau. "Response of Plant Growth and Development, and Accumulation of Hydroxyl-cinnamoyl Acid Derivatives to Selected Shade Nets and Seasonality of Field-grown Bush Tea (Athrixia phylicoides DC.)". HortScience 57, nr 1 (styczeń 2022): 87–96. http://dx.doi.org/10.21273/hortsci16171-21.
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Horticultural practices and quality of bush tea (Athrixia phylicoides DC.) are critical for herbal tea industrialization. The objective of the current study was to determine the effect of selected shade nets and seasonal variation on plant growth and development, and hydroxycinnamic acid content of field-grown bush tea. The trial was laid out in a randomized complete block design consisting of three shade nets (black, green, and white) and control or full sunlight with three different light intensities (40%, 50%, and 80%) replicated three times. Proportion of intercepted radiation by the canopy, chlorophyll content, plant height, and fresh and dry mass were measured, and hydroxycinnamic acid accumulation was determined. In addition, hydroxycinnamic acid composition was determined using liquid chromatography linked to mass spectrometry (LC-MS). The application of shade nets resulted in plant growth and yield reduction as compared with the plants exposed to full sunlight during summer followed by white shade net. The accumulation of hydroxycinnamic acid was higher in 80% white shade net plots compared with unshaded plants (control) and the other shade nets. Therefore, lack of shading provides a conducive environment to enhance plant growth and development of bush tea. The white shade net (80%) was an effective microclimate tool to enhance accumulation of caffeoylquinic acid (m/z 353), p-coumaric acids (m/z 337), dicaffeoylquinic acid (m/z 515), and tricaffeoylquinic acids of bush tea. This study is the first to demonstrate light as a determining factor for production of chlorogenates in bush tea plants. Future studies will be conducted to determine the effect of light on extracts of the bush tea using different solvents.
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Sydora, Natalia, Volodymyr Yakovenko, Oleksandr Ochkur, Anna Rudnyk, Oleksandr Honcharov, Svetlana Zuikina, Kateryna Romas i Mykhailo Marchenko. "Technology of obtaining and chemical profiles of dry extracts from leaves of prospective species of the hawthorn genus". ScienceRise: Pharmaceutical Science, nr 1(41) (28.02.2023): 58–66. http://dx.doi.org/10.15587/2519-4852.2023.274772.
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The aim of the work was to develop a technology for obtaining dry extracts from leaves of non-pharmacopoeia species of hawthorn and establishing their chemical profiles. Materials and methods. Leaves of Crataegus mollis Sarg., Crataegus submollis Sarg. and Crataegus arnoldiana Sarg., used to obtain the dry extracts, were harvested in the Botanical Garden of the National University named after M. N. Karazina in August 2021. To determine the chemical profiles of the obtained dry extracts, the spectrophotometric method and the high-performance liquid chromatography (HPLC) method were used. Results. A technological scheme for obtaining dry extracts of hawthorn leaves has been developed. The content of flavonoids and hydroxycinnamic acids in dry extracts of the leaves of C. mollis Sarg., C. submollis Sarg. and C. arnoldiana Sarg. was determined. The content of free amino acids in extracts ranges from 0.70 % to 0.99 %. The content of flavonoids ranged from 7.25 %±0.04 to 8.43 %±0.01, of hydroxycinnamic acids - from 2.35 %±0.02 to 2.85 %±0.03. Rutin, kaempferol-3-O-glycoside, epicatechin and chlorogenic acid were identified in all extracts by the HPLC method. In dry leaf extracts of C. arnoldiana Sarg. and C. mollis identified p-coumaric acid; C. arnoldiana Sarg. – quercetin; C. arnoldiana Sarg. and C. submollis Sarg. – ferulic acid; C. submollis Sarg. and C. mollis Sarg. – quercetin-3-O-rhamnoside. Conclusions. Dry leaf extracts of C. mollis Sarg., C. submollis Sarg. and C. arnoldiana Sarg. were obtained. For the first time, the content of flavonoids and hydroxycinnamic acids in the extracts was determined by HPLC. It was established that the chemical profile of the obtained extracts is formed by rutin, chlorogenic acid and kaempferol-3-O-glycoside, which can be used in further standardization of these substances. In addition, a comparative study of the amino acid composition of the obtained extracts was carried out for the first time
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Peng, Fei, Habibu Aliyu, André Delavault, Ulrike Engel i Jens Rudat. "Computational-Designed Enzyme for β-Tyrosine Production in Lignin Valorization". Catalysts 11, nr 11 (29.10.2021): 1310. http://dx.doi.org/10.3390/catal11111310.
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Lignin is an underutilized sustainable source of aromatic compounds. To valorize the low-value lignin monomers, we proposed an efficient strategy, involving enzymatic conversion from trans-p-hydroxycinnamic acids to generate valued-added canonical and non-canonical aromatic amino acids. Among them, β-amino acids are recognized as building blocks for bioactive natural products and pharmaceutical ingredients due to their attractive antitumor properties. Using computational enzyme design, the (R)-β-selective phenylalanine aminomutase from Taxus chinensis (TchPAM) was successfully mutated to accept β-tyrosine as the substrate, as well as to generate the (R)-β-tyrosine with excellent enantiopurity (ee > 99%) as the unique product from trans-p-hydroxycinnamic acid. Moreover, the kinetic parameters were determined for the reaction of four Y424 enzyme variants with the synthesis of different phenylalanine and tyrosine enantiomers. In the ammonia elimination reaction of (R)-β-tyrosine, the variants Y424N and Y424C displayed a two-fold increased catalytic efficiency of the wild type. In this work, a binding pocket in the active site, including Y424, K427, I431, and E455, was examined for its influence on the β-enantioselectivity of this enzyme family. Combining the upstream lignin depolymerization and downstream production, a sustainable value chain based on lignin is enabled. In summary, we report a β-tyrosine synthesis process from a monolignol component, offering a new way for lignin valorization by biocatalyst modification.
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Peyrot, Cédric, Matthieu M. Mention, Fanny Brunissen, Patrick Balaguer i Florent Allais. "Innovative Bio-Based Organic UV-A and Blue Light Filters from Meldrum’s Acid". Molecules 25, nr 9 (6.05.2020): 2178. http://dx.doi.org/10.3390/molecules25092178.
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Faced with the ban of some organic UV filters such as octinoxate or avobenzone, especially in Hawaii, it became essential to offer new alternatives that are both renewable and safe for humans and the environment. In this context, a class of bio-based molecules displaying interesting UV filter properties and great (photo)stability has been developed from Meldrum’s acid and bio-based and synthetic p-hydroxycinnamic acids, furans and pyrroles. Moreover, p-hydroxycinnamic acid-based Meldrum’s derivatives possess valuable secondary activities sought by the cosmetic industry such as antioxidant and anti-tyrosinase properties. The evaluation of the properties of mixture of judiciously chosen Meldrum’s acid derivatives highlighted the possibility to modulate secondary activity while maintaining excellent UV protection. Meldrum’s acid derivatives are not only competitive when benchmarked against organic filters currently on the market (i.e., avobenzone), but they also do not exhibit any endocrine disruption activity.
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Suodkolae, Massoumeh, Teimouri Yansari i Yadollah Chashnidel. "Effects of hydroxycinnamic acids (Ferulic and p-coumaric acids) in barley cultivars on cell wall components degradability in rumen". Biotehnologija u stocarstvu 33, nr 3 (2017): 271–89. http://dx.doi.org/10.2298/bah1703271s.
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Barley grain contains hydroxycinnamic acids especially Ferulic (FA) and p-Coumaric acid (pCA) become cross-linked to cell wall polysaccharids as lignification commences that are the major inhibiting factors of biodegradability of plant cell walls in the rumen. Chemical characteristics, FA and pCA content of 11 Iranian barley cultivars determined. Using 3 fistulated ewes, the effects of FA and pCA content on ruminal degradation of dry matter (DM), neutral and acid detergent fiber (NDF and ADF) and lignin were studied. In barley cultivars, DM varied from 82.52 to 90.90 %; NDF varied from 9.64 to 27.34 % DM; ADF varied from 2.03 to 8.13 % DM and lignin varied from 0.87 to 3.03 % DM. The FA content ranged from 151.2 to 354.2 ?g/g; and pCA content ranged from 114.5 to 444.4 ?g/g of DM. Ruminal degradation parameters for DM, NDF, ADF and lignin were different between barley cultivars. The soluble fraction, slowly degradable, potential degradable, and undegradable fraction of DM were 2.92 to 56.33%; 42.64 to 91.45%; 65.68 to 98.97%, and 1.02 to 34.31%, respectively. The rate of ruminal degradation for DM varied among barley cultivars from 3.64 to 27.81% h-1. The FA was related to rumen indigestible DM, NDF, ADF and lignin, while pCA correlated with ADF. Using multi-regression, FA and pCA were inhibiting factors of ruminal degradability for DM and cell wall components; and FA was the most effective factor to predict DM degradability, while both FA and pCA affected NDF and ADF ruminal degradability.
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Azzini, E., R. Bugianesi, F. Romano, D. Di Venere, S. Miccadei, A. Durazzo, M. S. Foddai, G. Catasta, V. Linsalata i G. Maiani. "Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads ofCynara scolymusL. (cultivar Violetto di Provenza) in human subjects: a pilot study". British Journal of Nutrition 97, nr 5 (maj 2007): 963–69. http://dx.doi.org/10.1017/s0007114507617218.
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The current growing interest for natural antioxidants has led to a renewed scientific attention for artichoke, due not only to its nutritional value, but, overall, to its polyphenolic content, showing strong antioxidant properties. The major constituents of artichoke extracts are hydroxycinnamic acids such as chlorogenic acid, dicaffeoylquinic acids caffeic acid and ferulic acid, and flavonoids such as luteolin and apigenin glycosides.Invitrostudies, using cultured rat hepatocytes, have shown its hepatoprotective functions andin vivostudies have shown the inhibition of cholesterol biosynthesis in human subjects. Several studies have shown the effect on animal models of artichoke extracts, while information on human bioavailability and metabolism of hydroxycinnamates derivatives is still lacking. Results showed a plasma maximum concentration of 6·4 (sd 1.8) ng/ml for chlorogenic acid after 1 h and its disappearance within 2 h (P < 0·05). Peak plasma concentrations of 19·5 (sd6·9) ng/ml for total caffeic acid were reached within 1 h, while ferulic acid plasma concentrations showed a biphasic profile with 6·4 (sd1·5) ng/ml and 8·4 (sd4·6) ng/ml within 1 h and after 8 h respectively. We observed a significant increase of dihydrocaffeic acid and dihydroferulic acid total levels after 8 h (P < 0·05). No circulating plasma levels of luteolin and apigenin were present. Our study confirms the bioavailability of metabolites of hydroxycinnamic acids after ingestion of cooked edibleCynara scolymusL. (cultivar Violetto di Provenza).
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Schefe, C. R., i K. Tymms. "Phased addition of organic and phenolic acids with phosphate fertiliser increases P availability in an acid soil". Soil Research 51, nr 5 (2013): 437. http://dx.doi.org/10.1071/sr13126.
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The role of carboxylic acids in increasing soil phosphorus (P) availability has been well established, using both organic and phenolic acids. However, the practical application of this knowledge in farming systems is still a developing research area. This study determined the amount of carboxylic acid required per unit P fertiliser for increased solution P concentrations and the optimum order of application, with carboxylic acids applied before (phased addition), or in conjunction with (co-addition), the P fertiliser. Two inorganic P fertilisers (potassium dihydrogen phosphate, KH2PO4; diammonium phosphate, DAP) were applied to an acid soil in conjunction with seven carboxylic acids (oxalic, malic, citric, 4-hydroxybenzoic, protocatechuic, 4-hydroxycinnamic, and caffeic acids) in a series of short-term adsorption and desorption experiments. When the carboxylic acids were applied to soil without P, they all increased solution P concentrations. When applied with P fertiliser, the highest solution P concentrations were measured when solutions of oxalic, citric, or protocatechuic acids were equilibrated with soil before the addition of DAP fertiliser (phased addition). In comparison, phased addition of KH2PO4 fertiliser with malic or citric acids resulted in the greatest potential for subsequent desorption of P from the soil. It is proposed that coating of DAP fertiliser granules with an organic/phenolic acid blend may enhance P fertiliser efficiency in acidic cropping soil through reduced P loss via adsorption onto soil surfaces.
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Basaraba, Roksolana, Alona Savych, Svitlana Marchyshyn, Nataliіa Muzyka i Pavlina Ilashchuk. "HPLC-DAD assay of phenols profile in Antennaria dioica (L.) Gaertn". Pharmacia 69, nr 2 (10.05.2022): 393–99. http://dx.doi.org/10.3897/pharmacia.69.e81654.
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Antennaria dioica (Asteraceae family) – is a perennial herb, commonly found in dry grasslands and sandy or stony places from Eurasian areas. It is known in traditional medicine as antioxidant, diuretic, choleretic and anti-inflammatory remedy. This species should be reconsidered as possible sources of phenols, mainly flavonoids and hydroxycinnamic acids. Thus, the aim of this study was to validate a chromatographic method for detection of phenols and their identification in A. dioica herb. HPLC-DAD method was evaluated in terms of linearity, precision, repeatability, accuracy, LOD and LOQ. The calibration curves of thirteen reference substances were linear (R2 > 0.99) over the range of 5–400 µg/mL, the LODs and the LOQs were in the range of 0.1–0.3 µg/mL and 0.2–1.0 µg/mL, respectively. During HPLC-DAD assay two flavones – luteolin, apigenin; flavonol – quercetin and three its glycosides – rutin, hyperoside and isoquercitrin; coumarins: coumarin and umbelliferone; five hydroxycinnamic acids – chlorogenic, caffeic, p-coumaric, trans-ferulic and rosmarinic were identified in A. dioica herb. This phytochemical study of A. dioica confirms that this plant material is a rich source of phenolic compounds.
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Salazar-López, Norma Julieta, Gustavo A. González-Aguilar, Guadalupe Loarca-Piña, Francisco J. Cinco-Moroyoqui, Ofelia Rouzaud-Sández, J. Abraham Domínguez-Avila i Maribel Robles-Sánchez. "Contribution and Interactions of Hydroxycinnamic Acids Found in Bran and Wholegrain Sorghum (Sorghum bicolorL. Moench): Effects on the Antioxidant Capacity and Inhibition of Human Erythrocyte Hemolysis". Oxidative Medicine and Cellular Longevity 2017 (2017): 1–8. http://dx.doi.org/10.1155/2017/8219023.
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An imbalance between free radicals and antioxidants is known as oxidative stress, and it promotes cellular aging and the development of chronic noncommunicable diseases. The bioactive compounds present in food play an important role in preventing oxidative stress. The aim of this study was to determine the contributions and interactions of the hydroxycinnamic acids found in the bran and whole grain of sorghum and to evaluate their effects on the antioxidant capacity and inhibition of the hemolysis of human erythrocytes. Results showed that the caffeic acid,p-coumaric acid, and ferulic acid found in sorghum contributed to the scavenging of DPPH and ABTS radicals in various proportions. Ferulic acid, which was present in bound form in the bran and wholegrain sorghum, significantly inhibited the AAPH radical-induced oxidation of the erythrocyte membranes by 78.0 and 4.3%, respectively. Combinations of two, three, or four hydroxycinnamic acids may interact in an antagonistic or synergistic manner, thereby altering each other’s bioactivities. The various interactions between the different sorghum bioactives can have a significant impact on their potential bioactivities. These results can be useful in the design of functional foods that aim to deliver bioactives to mitigate cellular aging or noncommunicable diseases.
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Bebek Markovinović, Anica, Predrag Putnik, Paula Bičanić, Dora Brdar, Boris Duralija, Branimir Pavlić, Sanja Milošević, Gabriele Rocchetti, Luigi Lucini i Danijela Bursać Kovačević. "A Chemometric Investigation on the Functional Potential in High Power Ultrasound (HPU) Processed Strawberry Juice Made from Fruits Harvested at two Stages of Ripeness". Molecules 28, nr 1 (24.12.2022): 138. http://dx.doi.org/10.3390/molecules28010138.
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This work aimed to investigate the influence of high-power ultrasound (HPU) technology on the stability of bioactive compounds in strawberry juices obtained from fruits with different stages of ripeness (75% vs. 100%) and stored at 4 °C for 7 days. HPU parameters were amplitude (25, 50, 75, and 100%), pulses (50 vs. 100%) and treatment time (5 vs. 10 min). Amplitude and pulse had a significant effect (p ≤ 0.05) on all bioactive compounds except flavonols and hydroxycinnamic acids. The treatment duration of 5 min vs. 10 min had a significant positive impact on the content of anthocyanins, flavonols and condensed tannins, while the opposite was observed for total phenols, whereas no statistically significant effect was observed for hydroxycinnamic acids. The temperature changes during HPU treatment correlated positively with almost all HPU treatment parameters (amplitude, pulse, energy, power, frequency). Optimal parameters of HPU were obtained for temperature changes, where the highest content of a particular group of bioactive compounds was obtained. Results showed that by combining fruits with a certain ripeness and optimal HPU treatment, it would be possible to produce juices with highly preserved bioactive compounds, while HPU technology has prospects for application in functional food products.
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Yu, P., J. J. McKinnon, D. D. Maenz, V. J. Racz i D. A. Christensen. "The interactive effects of enriched sources of Aspergillus ferulic acid esterase and Trichoderma xylanase on the quantitative release of hydroxycinnamic acids from oat hulls". Canadian Journal of Animal Science 82, nr 2 (1.06.2002): 251–57. http://dx.doi.org/10.4141/a01-035.
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Oat hulls contain relatively high amounts of hydroxycinnamic acids, mainly ferulic (4-hydroxy-3-methoxycinnamic) and p-coumaric acids (4-hydroxy-cinnamic), which are inhibitory to cell wall biodegradability by rumen microorganisms. In this paper, a study of the interactive effects of enriched sources of Aspergillus ferulic acid esterase (A-FAE) and Trichoderma xylanase (T-XYL) at different levels on the quantitative release of ferulic acid and p-coumaric acid from oat hulls was carried out. The results show that relative to A-FAE alone, the combined action of A-FAE and T-XYL was superior in causing the release of ferulic acid [up to 41.0% (± 2.1%)], indicating that T-XYL is important in acting with A-FAE in the degradation of feruloyl-polysaccharides of oat hulls. There was no effect of A-FAE alone, but a significant effect of A-FAE in combination with T-XYL on the release of p-coumaric acid from oat hulls. However, there was no extensive release of p-coumaric acid [(maximum release of 9.0% (± 0.7%)] by A-FAE in the presence of T-XYL, indicating a specificity of A-FAE for feruloyl groups, which only efficiently releases ferulic acid and not p-coumaric acid from oat hulls. This study suggests that A-FAE with T-XYL has an interactive effect to be able to break the ester linkage between ferulic acid and the attached sugar, releasing a significant proportion of the ferulic acid from oat hulls. This action, which causes disruption of crosslinks, has the potential to improve hydrolysis of the remaining polysaccharides by rumen microorganisms, which, in turn, would improve rumen degradability of oat hulls. Key words: Ferulic acid esterase, oat hulls, hydroxycinnamic acids, biodegradation
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Furia, Emilia, Amerigo Beneduci, Luana Malacaria, Alessia Fazio, Chiara La Torre i Pierluigi Plastina. "Modeling the Solubility of Phenolic Acids in Aqueous Media at 37 °C". Molecules 26, nr 21 (28.10.2021): 6500. http://dx.doi.org/10.3390/molecules26216500.
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In this work, the solubility of vanillic, gallic, syringic, p-coumaric, ferulic and caffeic acids was determined at 37 °C under different conditions, namely pure water and two different ionic media, NaCl(aq) and NaClO4(aq), at different ionic strengths (i.e., 0.16, 0.50, 1.0, 2.0 and 3.0 M). The solubility in water of all the acids was found to be higher than that in both of the ionic media. Moreover, the solubility of hydroxycinnamic acids was lower than that of hydroxybenzoic acids. The activity coefficients of neutral species were calculated from these data; this knowledge is necessary when modeling the dependence of equilibrium constants on the ionic strength. Results obtained in this work can be useful for further studies regarding complex formation equilibria between these ligands and bioavailable metal cations.
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Poveda, Jorge, Pablo Velasco, Antonio de Haro, Tor J. Johansen, Alex C. McAlvay, Christian Möllers, Jørgen A. B. Mølmann, Elena Ordiales i Víctor M. Rodríguez. "Agronomic and Metabolomic Side-Effects of a Divergent Selection for Indol-3-Ylmethylglucosinolate Content in Kale (Brassica oleracea var. acephala)". Metabolites 11, nr 6 (14.06.2021): 384. http://dx.doi.org/10.3390/metabo11060384.
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Brassica oleracea var. acephala (kale) is a cruciferous vegetable widely cultivated for its leaves and flower buds in Europe and a food of global interest as a “superfood”. Brassica crops accumulate phytochemicals called glucosinolates (GSLs) which play an important role in plant defense against biotic stresses. Studies carried out to date suggest that GSLs may have a role in the adaptation of plants to different environments, but direct evidence is lacking. We grew two kale populations divergently selected for high and low indol-3-ylmethylGSL (IM) content (H-IM and L-IM, respectively) in different environments and analyzed agronomic parameters, GSL profiles and metabolomic profile. We found a significant increase in fresh and dry foliar weight in H-IM kale populations compared to L-IM in addition to a greater accumulation of total GSLs, indole GSLs and, specifically, IM and 1-methoxyindol-3-ylmethylGSL (1MeOIM). Metabolomic analysis revealed a significant different concentration of 44 metabolites in H-IM kale populations compared to L-IM. According to tentative peak identification from MS interpretation, 80% were phenolics, including flavonoids (kaempferol, quercetin and anthocyanin derivates, including acyl flavonoids), chlorogenic acids (esters of hydroxycinnamic acids and quinic acid), hydroxycinnamic acids (ferulic acid and p-coumaric acid) and coumarins. H-IM kale populations could be more tolerant to diverse environmental conditions, possibly due to GSLs and the associated metabolites with predicted antioxidant potential.
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Fási, Laura, Ahmed Dhahir Latif, István Zupkó, Sándor Lévai, Miklós Dékány, Zoltán Béni, Árpád Könczöl, György Tibor Balogh i Attila Hunyadi. "AAPH or Peroxynitrite-Induced Biorelevant Oxidation of Methyl Caffeate Yields a Potent Antitumor Metabolite". Biomolecules 10, nr 11 (11.11.2020): 1537. http://dx.doi.org/10.3390/biom10111537.
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Hydroxycinnamic acids represent a versatile group of dietary plant antioxidants. Oxidation of methyl-p-coumarate (pcm) and methyl caffeate (cm) was previously found to yield potent antitumor metabolites. Here, we report the formation of potentially bioactive products of pcm and cm oxidized with peroxynitrite (ONOO¯), a biologically relevant reactive nitrogen species (RNS), or with α,α′-azodiisobutyramidine dihydrochloride (AAPH) as a chemical model for reactive oxygen species (ROS). A continuous flow system was developed to achieve reproducible in situ ONOO¯ formation. Reaction mixtures were tested for their cytotoxic effect on HeLa, SiHa, MCF-7 and MDA-MB-231 cells. The reaction of pcm with ONOO¯ produced two fragments, an o-nitrophenol derivative, and a new chlorinated compound. Bioactivity-guided isolation from the reaction mixture of cm with AAPH produced two dimerization products, including a dihydrobenzofuran lignan that exerted strong antitumor activity in vitro, and has potent in vivo antimetastatic activity which was previously reported. This compound was also detected from the reaction between cm and ONOO¯. Our results demonstrate the ROS/RNS dependent formation of chemically stable metabolites, including a potent antitumor agent (5), from hydroxycinnamic acids. This suggests that diversity-oriented synthesis using ROS/RNS to obtain oxidized antioxidant metabolite mixtures may serve as a valid natural product-based drug discovery strategy.
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Fabroni, Simona, Angela Trovato, Gabriele Ballistreri, Susanna Aurora Tortorelli, Paola Foti, Flora Valeria Romeo i Paolo Rapisarda. "Almond [Prunus dulcis (Mill.) DA Webb] Processing Residual Hull as a New Source of Bioactive Compounds: Phytochemical Composition, Radical Scavenging and Antimicrobial Activities of Extracts from Italian Cultivars (‘Tuono’, ‘Pizzuta’, ‘Romana’)". Molecules 28, nr 2 (6.01.2023): 605. http://dx.doi.org/10.3390/molecules28020605.
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In this study we developed a new extract, by the use of conventional solid-solvent extraction and a food-grade hydroalcoholic solvent, rich in phenolic and triterpenoid components from almon hull to be employed as functional ingredient in food, pharma and cosmetic sectors. Two autochthonous Sicilian cultivars (‘Pizzuta’ and ‘Romana’) and an Apulian modern cultivar (‘Tuono’) have been tested for the production of the extract. Results showed that the two Sicilian varieties, and in particular the ‘Romana’ one, present the best characteristics to obtain extracts rich in triterpenoids and hydroxycinnamic acids, useful for the production of nutraceutical supplements. About triterpenoids, the performance of the hydroalcoholic extraction process allowed to never go below 46% of recovery for ‘Pizzuta’ samples, with significantly higher percentages of recovery for ‘Tuono’ and ‘Romana’ extracts (62.61% and 73.13%, respectively) while hydroxycinnamic acids were recovered at higher recovery rate (84%, 89% and 88% for ‘Pizzuta’, ‘Romana’ and ‘Tuono’ extracts, respectively). Invitro antioxidant and antimicrobial activities exerted by the extracts showed promising results with P. aeruginosa being the most affected strain, inhibited up to the 1/8 dilution with ‘Romana’ extract. All the three tested extracts exerted an antimicrobial action up to 1/4 dilutions but ‘Romana’ and ‘Pizzuta’ extracts always showed the greatest efficacy.
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Jeon, Sangeun, Jisub Hwang, Hackwon Do, Ly Thi Huong Luu Le, Chang Woo Lee, Wanki Yoo, Min Ju Lee i in. "Feruloyl Esterase (LaFae) from Lactobacillus acidophilus: Structural Insights and Functional Characterization for Application in Ferulic Acid Production". International Journal of Molecular Sciences 24, nr 13 (6.07.2023): 11170. http://dx.doi.org/10.3390/ijms241311170.
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Ferulic acid and related hydroxycinnamic acids, used as antioxidants and preservatives in the food, cosmetic, pharmaceutical and biotechnology industries, are among the most abundant phenolic compounds present in plant biomass. Identification of novel compounds that can produce ferulic acid and hydroxycinnamic acids, that are safe and can be mass-produced, is critical for the sustainability of these industries. In this study, we aimed to obtain and characterize a feruloyl esterase (LaFae) from Lactobacillus acidophilus. Our results demonstrated that LaFae reacts with ethyl ferulate and can be used to effectively produce ferulic acid from wheat bran, rice bran and corn stalks. In addition, xylanase supplementation was found to enhance LaFae enzymatic hydrolysis, thereby augmenting ferulic acid production. To further investigate the active site configuration of LaFae, crystal structures of unliganded and ethyl ferulate-bound LaFae were determined at 2.3 and 2.19 Å resolutions, respectively. Structural analysis shows that a Phe34 residue, located at the active site entrance, acts as a gatekeeper residue and controls substrate binding. Mutating this Phe34 to Ala produced an approximately 1.6-fold increase in LaFae activity against p-nitrophenyl butyrate. Our results highlight the considerable application potential of LaFae to produce ferulic acid from plant biomass and agricultural by-products.
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Mironov, M. A., M. Yu Akimov, V. A. Koltsov i R. E. Bogdanov. "Investigation of the complex of phenolic compounds in fruits of the domestic plum (Prunus domestica L.) in conditions of Tambov Region". Rossiiskaia selskokhoziaistvennaia nauka, nr 3 (15.06.2023): 25–30. http://dx.doi.org/10.31857/s2500262723030055.
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The fruits of Prunus domestica L. are a valuable source of phenolic compounds, in particular hydroxycinnamic acids and their esters. Hybrid origin of Prunus domestica hexaploid species, a huge variety of varieties and di erent growing areas do not allow scientists to make a de nitive conclusion about certain phenolic compounds in plum fruits. The purpose of our research is to determine and identify the phenolic composition of fruits of Prunus domestica L. growing in the Tambov region of the Russian Federation. Eight varieties of universal and table plum were taken as objects of research. Experimental plantations were planted in 2014 according to the scheme of 6x3 m. SVG 11-19 was used as a rootstock. The study of phenolic components of plum fruits was performed by HPLC using a Thermo Ultimate 3000 liquid chromatograph equipped with a DAD-3000. Separation was performed on a Hypersil Gold C18 column (4.6 × 250 mm, 5 μm). The binary mobile phase gradient was phosphate and acetonitrile. For the analysis, plum fruits were extracted with 70 % aqueous methanol. The levels of hydroxycinnamic acids in the plum fruits studied were determined: 4-ca eoylquinic acid-5.33…181.54 mg/100 g, 5- ca eoylquinic acid - 1.69…31.73 mg/100 g, 3-p-coumaroylquinic acid - 0.54…5.77 mg/100 g, 3- ca eoylquinic acid-0.04…0.63 mg/100 g. Among avonols, the predominant component is quercitin-3-rutinoside - 0.77…9.17 mg/100 g. Three anthocyanins were identi ed in the studied plum fruits: cyanidin-3-glucoside, cyanidin-3-rutinoside and peonidin-3-glucoside. In the structural composition of plum fruit anthocyanins, cyanidin-3-glucoside dominates, accounting for 60 to 90 % of the total anthocyanin content. The obtained data on the content of phenolic components in fruits of isolated plum varieties (Prunus domestica L.) indicate the promise of their further study for breeding studies and as a source of hydroxycinnamic acids, anthocyanins and avonols in the diet of the population
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Mv, Melnyk, Vodoslavskyi Vm i Obodianskyi Ma. "RESEARCH OF PHENOLIC COMPOUNDS OF RUTA GRAVEOLENS L. AND STELLARIA MEDIA (L.) VILL". Asian Journal of Pharmaceutical and Clinical Research 11, nr 9 (7.09.2018): 152. http://dx.doi.org/10.22159/ajpcr.2018.v11i9.25920.
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Objective: The results of the determination of the phenolic compounds in Ruta graveolens L. and Stellaria media (L.) Vill. herb by the method of high-performance liquid chromatography (HPLC) with ultraviolet (UV)-detection are presented in the article.Method: The qualitative composition and quantitative content of the phenolic compounds were studied by HPLC on the Agilent 1200 chromatograph using methanolic extracts of R. graveolens L. and S. media (L.) Vill. herb. The components of hydroxycinnamic acids were determined at wavelengths of 320 nm and 330 nm; flavonoids at 255 nm and 340 nm; and tannins at 255 nm and 280 nm.Results: On the basis of the analysis conducted by the method of HPLC in the herb of R. graveolens L., 16 substances were identified: 6 flavonoids (apigenin, rutin, quercetin, luteolin, isoquercetin, and hyperoside), 4 hydroxycinnamic acids (chlorogenic, rosmarinic, caffeic, and p-coumaric), and 6 tannins (gallic and ellagic acids, gallocatechin, epigallocatechin, epicatechin, and epicatechin gallate). In the herb of S. media (L.) Vill., chlorogenic acid, flavone aglycones: Luteolin and apigenin, and flavonol glycosides: Isoquercetin and rutin were identified.Conclusion: According to the results of the research, it was established that the dominant components of R. graveolens L. and S. media (L.) Vill. herb are chlorogenic acid and a flavonoid component apigenin, which has anti-inflammatory activity. Thus, the obtained results point to the prospect of further research with the aim of creating of herbal substances with a certain pharmacological action.
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Daquino, Carmelo, i Mario C. Foti. "Coupling and fast decarboxylation of aryloxyl radicals of 4-hydroxycinnamic acids with formation of stable p-quinomethanes". Tetrahedron 62, nr 7 (luty 2006): 1536–47. http://dx.doi.org/10.1016/j.tet.2005.11.010.
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Ferrara, M., A. Gallo, R. Lo Scalzo, M. Haidukowski, V. Picchi i G. Perrone. "Inhibition of ochratoxin A production in Aspergillus carbonarius by hydroxycinnamic acids from grapes". World Mycotoxin Journal 8, nr 3 (1.01.2015): 283–89. http://dx.doi.org/10.3920/wmj2014.1753.
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Hydroxycinnamic acids (HCAs), phenolic components of wine, are known to have antimicrobial properties. Aspergillus carbonarius is one of the most important ochratoxin A (OTA) producing fungi in wine. Strategies for the control and prevention of A. carbonarius contamination are important for the maintenance of wine safety. This study sought to determine the potential of HCAs, such as caffeic, p-coumaric and ferulic acids, as antifungal natural compounds for the control of A. carbonarius growth and OTA production. The HCAs were tested at the increasing concentrations of 0.30, 0.65 and 1.10 mg/ml in minimal medium (MM) and grape juice. Germination of conidia was not affected in neither of the two media in presence of HCAs. At all the concentrations tested, OTA biosynthesis in MM was reduced and the dose effect was more evident for p-coumaric and ferulic acids; in grape juice the reduction trend was confirmed, and ferulic acid showed the highest inhibitory effect. Moreover, the expression level of genes encoding a polyketide synthase (AcOTApks) and a nonribosomal peptide synthetase (AcOTAnrps) involved in OTA biosynthesis, was evaluated by real-time PCR in A. carbonarius grown in presence of 0.65 mg/ml of HCAs. From gene expression analysis only the AcOTApks gene showed a marked reduction of transcription level in presence of p-coumaric and ferulic acids. On the contrary, caffeic acid seemed to not influence the expression levels of the genes analysed in this study, suggesting a different mechanism of action on the regulation of OTA biosynthesis.
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Bizjak, Jan, Nika Weber, Maja Mikulic-Petkovsek, Ana Slatnar, Franci Stampar, Zobayer Alam, Karl Stich, Heidi Halbwirth i Robert Veberic. "Influence of Phostrade Ca on Color Development and Anthocyanin Content of ‘Braeburn’ Apple (Malus domestica Borkh.)". HortScience 48, nr 2 (luty 2013): 193–99. http://dx.doi.org/10.21273/hortsci.48.2.193.
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The influence of two foliar applications of Phostrade Ca, which contains high concentrations of phosphorus and minor amounts of calcium and nitrogen, on color development and selected primary and secondary metabolites was investigated during advanced maturation of ‘Braeburn’ apple. Changes of hydroxycinnamic acids, flavanols, dihydrochalcones, flavonols, and anthocyanins were monitored six times during the advanced ripening until technological maturity of the fruits. Additionally, the changes in the chromatic values a*, h°, and the lightness coefficient L* were recorded weekly. The colorimetric parameters showed a significant difference in the intensity of red coloration between the treated and untreated apples. Spraying with Phostrade Ca also resulted in a significant increase in most individual sugars, total sugars, and concentration of anthocyanins and flavonols. Moreover, the amount of phosphorus (P) in the treated leaves was increased. However, the total phenolic content and accumulation of other classes of flavonoids such as hydroxycinnamic acids, flavonols, and dihydrochalcones were not influenced. Phostrade Ca treatment significantly increased dihydroflavonol 4-reductase (DFR) and slightly flavanone-3-hydroxylase (FHT) activity, which were correlated with anthocyanin synthesis but had no effect on phenylalanine ammonia lyase (PAL) and chalcone synthase/chalcone isomerase (CHS/CHI) activity. The results indicate that two foliar applications of Phostrade Ca late in the growing season represent an effective way to improve the color of ‘Braeburn’ apples at commercial harvest.
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Chen, Zhi-Yi, Yao-Sheng Lin, Xue-Ming Liu, Jing-Rong Cheng i Chun-Ying Yang. "Chemical Composition and Antioxidant Activities of Five Samples of Prunus mume Umezu from Different Factories in South and East China". Journal of Food Quality 2017 (2017): 1–7. http://dx.doi.org/10.1155/2017/4878926.
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This paper investigated chemical composition and antioxidant activities of umezu, pickling liquid of Prunus mume, from different factories in South and East China. The organic acid and phenolic acid profiles were also analyzed. Results showed that umezu was rich in organic acids and extremely sour as P. mume fruit in addition to its high NaCl level (≥20%). Total acid in umezu was more than 43.78 g/L in which main organic acids were citric acid and malic acid. Umezu contained more than 250.54 mg GAE/L total phenolic in which dominant phenolic acids were hydroxycinnamic acid derivatives. Umezu exhibited powerful antioxidant activities in ORAC, ABTS, DPPH, and FRAP assays. Reducing sugar, phenolic compounds, and antioxidant activities of umezu were affected by sample origins and fruit cultivars. Given its rich flavor components and high antioxidant activity, umezu could serve as a new dietary supplement or a natural preservative in food industry.
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Мазулін, О. В., Л. А. Фуклева i Г. В. Мазулін. "Study of the polyphenolic compounds accumulation in Thymus serpyllum L. herb during the flowering period". Farmatsevtychnyi zhurnal, nr 2 (26.04.2023): 58–66. http://dx.doi.org/10.32352/0367-3057.2.23.07.
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The Thymus serpyllum L. is a widespread in the steppe bioсenosеs of southern and eastern Ukraine. It is well cultivated in specialized farms. A promising direction of modern phytochemical research of wild and cultivated Thymus L. species is the determination of the accumulation of biologically active polyphenolic compounds that exhibit pronounced biological activity.
The purpose of the work is to determine the accumulation of polyphenolic compounds in Thymus serpyllum L. herb at the flowering using TLC and HPLC methods.
The Thymus serpyllum L. herb was harvested in steppe biocenoses of southern and eastern Ukraine at the flowering, during the period of biologically active polyphenolic compounds maximum accumulation. For experimental studies, alcohol extracts from Thymus serpyllum L. herb (1:100) were used. The substances component composition was studied by TLC method Biostep CD 60 densitometer (Germany) and HPLC Agilent 1260 Infinity HPLC System Open LABCDS Software (Japan).
TLC and HPLC methods revealed up to 25 polyphenolic compounds. Experimentally were determined 13 flavonoids and 12 hydroxycinnamic acids. All these biologically active compounds are well known in modern phytotherapy for their pronounced antimicrobial, anti-inflammatory and antioxidant activity. During the flowering period up to 25 polyphenolic compounds were identified and quantified in the ethanolic extract (1:100) obtained from Thymus serpyllum L. herbal raw material. Of these, 13 compounds were attributed to flavonoids with a defined total content (0.3 mg/100 mg) and 12 to hydroxycinnamic acids (0.9 mg/100 mg). The highest accumulation of hydroxycinnamic acids in the Thymus serpyllum L. herbal raw material were characterized by rosmarinic acid (12.77 + 1.19%), chlorogenic acid (8.55 + 0.79%) and p-coumaric acid (7.41 + 0.69%). Of flavonoids, the highest content were established for rutin (8.45 + 0.79%), luteolin (3.87 + 0.37%), luteolin-7-O-β-D-glucopyranoside (3.86 ± 0.33%), apigenin-7,4'-diglucoside (3.86 ± 0.32%), quercetin (3.85 ± 0.34%) and apigenin (3.81 ± 0.36%).
The results obtained by TLC and HPLC methods indicate the perspective of polyphenolic compounds research for the purpose of determining the biological activity of extracts and carrying out the standardization of Thymus serpyllum L. herb. The study of the polyphenolic compounds accumulation in the Thymus serpyllum L. plant raw materials is important for this standardization and obtaining effective phytopreparations.
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Marcucci, Maria Cristina, Federico Ferreres, Angela Ramalho Custódio, Marcia M. C. Ferreira, Vassya Stefanova Bankova, Cristina García-Viguera i Walter Antonio Bretz. "Evalution of Phenolic Compounds in Brazilian Propolis from Different Geographic Regions". Zeitschrift für Naturforschung C 55, nr 1-2 (1.02.2000): 76–81. http://dx.doi.org/10.1515/znc-2000-1-215.
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Abstract Chemometrics has been shown quite efficient to uncover relationships between chemical composition of a sample and its geographical origin. Forty propolis samples originated from the the South and South East of Brazil were analyzed by HPLC and 18 compounds of interest were studied which included: caffeic, p-coumaric and ferulic acids, and some of their derivatives, pinobanksin, a derivative of kaempferol and five phenolic compounds (assigned as 3-prenyl-4-hydroxycinnamic acid (PHCA ); 2,2-dimethyl-6-carboxyethnyl-2H-l-benzopyran (DCBE); 3,5-diprenyl-4-hydroxycinnamic acid (DHCA ); compound E (still unknown) and 6-propenoic-2,2-dimethyl-8-prenyl-2H-l-benzopyran acid (DPB). Principal Component Analysis (PCA) indicated three different groups of propolis samples, having the same typical chromatogram, evaluated by HPLC. Samples from the South East group were rich in derivatives of kaempferol. Samples from the South group I had a high content of DPB compound, but a low concentration of kaempferol derivatives and of DCBEN compound. Samples from the South group II were characterized by a high concentration of DCBEN , DHCA , p-coum-aric and DPB compounds. Therefore, the identification of new compounds in Brazilian propolis can give useful information about the plant sources of a given geographic region.