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Journal articles on the topic 'Para-coumaric acids'
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Mikhaylova, N.V., N.I. Belaya, A.V. Belyi, and V.A. Konailenko. "EFFECTS OF SUPERADDICTIVENESS OF COMPOSITIONS OF GALLIC AND PARA-COUMARIC ACIDS IN RADICAL OXIDATION REACTIONS." Вестник ДонНУ. Сер. А: Естественные науки, no. 1 (May 31, 2024): 75–84. https://doi.org/10.5281/zenodo.12532222.
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The kinetics and mechanism of the reaction of compositions of gallic and para-coumaric acids with the 2,2'-diphenyl-1-picrylhydrazyl radical in benzene were studied using photocolorimetry, NMR spectroscopy and quantum chemistry. The maximum antiradical synergistic effects were demonstrated by mixtures of gallic and para-coumaric acids in a ratio of 10 : 90 vol.%. A possible mechanism of synergy is the formation of phenolic dimers from the products of the primary transformation of phenolic acids (phenoxyl radicals), which can interact with the hydrazyl radical faster than the original antioxidants. Using the PM6 quantum-chemical semi-empirical method, it was established that the most probable is the formation of ortho, ortho-CC dimers, the molecules of which contain O–H groups with low energy of homolytic bond cleavage. <strong><em>Keywords: </em></strong>gallic acid, antiradical activity, synergism, 2,2'-diphenyl-1-picrylhydrazyl.
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Koster, Chris G. de, Gerard J. Niemann, and Wigger Heerma. "Fast Atom Bombardment Mass Spectrometry of Coumaric Acids." Zeitschrift für Naturforschung C 40, no. 7-8 (1985): 580–82. http://dx.doi.org/10.1515/znc-1985-7-823.
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Abstract The technique of positive fast atom bombardment mass spectrometry combined with collisional activation and metastable ion data has been shown to provide molecular mass and useful fragmentation information for discrimination between the coumaric acid isomers. In addition to the occurrence of an ortho-effect, also para and meta positions could be distinguished.
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Biela, Monika, Peter Poliak, Andrea Kleinová, Vladimír Lukeš, and Erik Klein. "ON THE THERMODYNAMICS OF ANTIOXIDANT ACTION OF NATURALLY OCCURRING HYDROXYDERIVATIVES OF CIS-CINNAMIC ACID." Journal of the Serbian Society for Computational Mechanics, Special (June 1, 2020): 26–36. http://dx.doi.org/10.24874/jsscm.2020.01.03.
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Antioxidant activity represents one of the important features of phenolic acids, such as hydroxyderivatives of cinnamic acid. However, in the case of cis-cinnamic acid derivatives, corresponding thermochemistry data can be still considered scarce. This work is focused on the two most relevant mechanisms of primary antioxidant action in gas-phase, non-polar benzene and in aqueous solution. Reaction enthalpies describing thermodynamics of Hydrogen Atom Transfer (HAT) and Sequential Proton-Loss – Electron Transfer (SPLET) mechanisms were theoretically investigated using (SMD) M06-2X/6-311++G(d,p) method for cis-ortho-coumaric, cis-meta-coumaric, cis-para-coumaric, cis-ferulic, cis-sinapic and cis-caffeic acid and their carboxylate anions. The effect of carboxyl COOH group deprotonation on the thermodynamics of studied mechanisms was assessed for the three environments.
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Baghestani, Ali, Claudel Lemieux, Gilles D. Leroux, Regis Baziramakenga, and Regis R. Simard. "Determination of allelochemicals in spring cereal cultivars of different competitiveness." Weed Science 47, no. 5 (1999): 498–504. http://dx.doi.org/10.1017/s0043174500092171.
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Competitive cereal cultivars are less susceptible than others to weed interference. Their characterization may provide selection criteria that can be used as guidelines to develop new, even more competitive cultivars. Root exudates are a potential means by which competitive cultivars reduce weed growth. The objectives of this study were to evaluate the effect of cereal root exudates onBrassica kaber(DC.) L. C. Wheeler growth, to isolate and characterize the allelochemical compounds released by spring cereal cultivars, and to determine if a relation exists between these allelochemicals and cultivar competitiveness. Highly competitive (HC) and lesser competitive (LC) cultivars of four crop kinds (Triticum aestivumL. [wheat],Avena sativaL. [wild oat], two- and six-rowedHordeum vulgareL. [barley]) were selected based on previous work. Exudates from undisturbed root systems ofB. kaberand cereals were collected and used in a bioassay test withB. kaber.Root exudates were analyzed for 16 common phenolic compounds using high-performance liquid chromatography (HPLC). Bioassays indicated that cereal exudates had no negative effect onB. kabergermination, but all concentrations of cereal root exudates inhibitedB. kaberroot and hypocotyl growth. As cereal root exudate concentration increased,B. kabergrowth decreased. For each crop kind,B. kabergrowth inhibition was greater with HC cultivars than with LC cultivars. The root exudates of all crop kinds and cultivars contained benzoic, caffeic, ferulic,o-coumaric, and vanillic acids as well as scopoletin. Para-hydroxybenzoic acid was found in exudates fromT. aestivum, A. sativa, and two-rowedH. vulgarecultivars. Para-coumaric acid was not identified in root exudates from LCH. vulgarecultivars. Gentisic acid was produced byA. sativaandH. vulgare.Vanillic ando-coumaric acids along with scopoletin may be responsible for the allelopathic effects ofH. vulgare, T. aestivum, andA. sativacultivars. These three compounds may be useful as possible indicators of allelopathic potential of genotypes under development and thus considered for use in breeding programs.
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Миронов, А. М., М. Ю. Акимов, В. А. Кольцов, Т. В. Жидехина, Д. М. Брыксин, and Н. В. Хромов. "ESTIMATION OF HYDROXYCINNAMIC ACIDS CONTENT IN BERRY FRUITS." За Мичуринское плодоводство, no. 1(1) (October 23, 2023): 32–35. http://dx.doi.org/10.34751/fnc-mich.2023.1.1.003.
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Продукция с высоким содержанием гидроксикоричных кислот благотворно воздействует на здоровье человека. В связи с этим возрастает научный интерес к оценке содержания гидроксикоричных кислот в плодах ягодных культур. Количественное определение гидрокискоричных кислот проводили с помощью метода обращенно-фазовой высокоэффективной жидкостной хроматографии. В качестве стандартов использовали: хлорогеновую кислоту (Fluka), кофейную кислоту (Fluka), para-кумаровую кислоту (Sigma), тrans-коричную кислоту (Aldrich), цикориевую кислоту (Sigma), тrans-феруловую кислоту (Sigma). Объектами исследования служили плоды различных сортов ягодных культур (жимолость, ирга, кизил, крыжовник, малина, смородина красная, смородина черная). Наиболее высоким содержанием хлорогеновой кислоты характеризовались плоды смородины черной сортов Тамерлан (64,29 мг/100 г) и Чернавка (61,89 мг/100 г), кофейной кислоты — смородины черной сорта Зеленая дымка (9,36 мг/100 г), р-кумаровой кислоты — смородины черной сорта Тамерлан (8,41 мг/100 г), цикориевой кислоты — кизила сорта Аббат (1,23 мг/100 г), транс-феруловой кислоты — крыжовника сорта Kuršu Dzintars (0,89 мг/100 г), т-коричной кислоты — кизила сорта Волгоградский грушевидный (1,03 мг/100 г). Products with a high content of hydroxycinnamic acids have beneficial effects on human health. In this regard, scientific interest in the evaluation of hydroxycinnamic acids content in berry fruits is increasing.Quantitative determination of hydroxycinnamic acids was carried out using reversed-phase high-performance liquid chromatography. Chlorogenic acid (Fluka), caffeic acid (Fluka), para-coumaric acid (Sigma), tranes-cinnamic acid (Aldrich), cichoric acid (Sigma), tranes-ferulic acid (Sigma) were used as standards. Fruit of berry crops (honeysuckle, honeysuckle, honeysuckle, cotoneaster, gooseberry, raspberry, red currant, black currant) served as objects of the study. The highest content of chlorogenic acid was observed in black currant fruits of Tamerlan (64.29 mg/100 g) and Chernavka (61.89 mg/100 g) varieties, caffeic acid — in black currant fruits of Green Smoke variety (9.36 mg/100 g), p-coumaric acid — black currant fruits of Tamerlan variety (8.41 mg/100 g), cichoric acid — in kizil Abbat berries (1.23 mg/100 g), trans-ferulic acid — gooseberry fruits of Kuršu Dzintars variety (0.89 mg/100 g), t-cinnamic acid — Volgograd pear-shaped kizil (1.03 mg/100 g).
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Wells, J. E., E. D. Berry, and V. H. Varel. "Effects of Common Forage Phenolic Acids on Escherichia coli O157:H7 Viability in Bovine Feces." Applied and Environmental Microbiology 71, no. 12 (2005): 7974–79. http://dx.doi.org/10.1128/aem.71.12.7974-7979.2005.
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ABSTRACT Ruminant animals are carriers of Escherichia coli O157:H7, and the transmission of E. coli O157:H7 from cattle to the environment and to humans is a concern. It is unclear if diet can influence the survivability of E. coli O157:H7 in the gastrointestinal system or in feces in the environment. Feces from cattle fed bromegrass hay or corn silage diets were inoculated with E. coli O157:H7, and the survival of this pathogen was analyzed. When animals consumed bromegrass hay for <1 month, viable E. coli O157:H7 was not recovered after 28 days postinoculation, but when animals consumed the diet for >1 month, E. coli O157:H7 cells were recovered for >120 days. Viable E. coli O157:H7 cells in feces from animals fed corn silage were detected until day 45 and differed little with the time on the diet. To determine if forage phenolic acids affected the viability of E. coli O157:H7, feces from animals fed corn silage or cracked corn were amended with common forage phenolic acids. When 0.5% trans-cinnamic acid or 0.5% para-coumaric acid was added to feces from silage-fed animals, the E. coli O157:H7 death rate was increased significantly (17-fold and 23-fold, respectively) compared to that with no addition. In feces from animals fed cracked corn, E. coli O157:H7 death rates were increased significantly with the addition of 0.1% and 0.5% trans-cinnamic acid (7- and 13-fold), 0.1% and 0.5% p-coumaric acid (3- and 8-fold), and 0.5% ferulic acid (3-fold). These data suggest that phenolic acids common to forage plants can decrease viable counts of E. coli O157:H7 shed in feces.
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Szwed, Magdalena, Joanna Mitrus, Wiesław Wiczkowski, Henryk Dębski, and Marcin Horbowicz. "The allelopathic properties of decomposing buckwheat residues are not directly related to phenolic compounds in soil." Plant, Soil and Environment 66, No. 5 (2020): 200–206. http://dx.doi.org/10.17221/124/2020-pse.
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Previous studies have shown that residues of common buckwheat roots (BRR) (but not entire common buckwheat plants, BPR) in the soil inhibited the growth of barnyardgrass (Echinochloa crus-galli L.). The objective of the study was to determine how both the residues affect the content of free phenolics, their esters and glycosides in the soil. The aqueous extracts were used to analyse of unbound phenolic compounds, while those bound to the soil were extracted with sodium citrate. Moreover, an in vitro test was used to assess the allelopathic effect of phenolic compounds present in the soil against barnyardgrass. Among the analysed phenolic compounds after 7 days of BPR and BRR decomposition, only ortho-, meta- and para-coumaric acids and apigenin were found in measurable amounts in the soil. The concentrations of free phenolic compounds were very low. Much higher contents occurred for the esters of these compounds, while no glycosides were found. The contents of phenolic compounds bound to soil were many times higher than unbound ones. The 37-day decomposition period resulted in an increase in bound phenolics, while the content of unbound changed slightly. Overall, the levels of phenolic compounds in the soil with the BRR-amended soil and no-buckwheat residue control were low, and significantly higher in the soil with BPR. An in vitro test showed that m-, p-coumaric acids and apigenin added to growth medium at a concentration higher than in the soil did not affect barnyardgrass shoot growth. Since the levels of phenolic compounds in the soil containing BRR and control soil were low and similar, phenolic compounds cannot be directly responsible for the allelopathic properties caused by the presence of BRR.
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Du, L., and P. Yu. "Effect of barley variety and growth year on ferulic and para-coumaric acids, and their ratio in the seed and hull." Cereal Research Communications 38, no. 4 (2010): 521–32. http://dx.doi.org/10.1556/crc.38.2010.4.9.
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Гурина, Д. Л., М. Л. Антипова, Е. Г. Одинцова, and В. Е. Петренко. "SOLVATION OF HYDROXYBENZOIC AND HYDROXYCINNAMIC ACIDS IN SUPERCRITICAL CARBON DIOXIDE. PECULIARITIES OF HYDROGEN BONDING WITH A POLAR COSOLVENT." Сверхкритические Флюиды: Теория и Практика 13, no. 2(2) (2020): 24–39. http://dx.doi.org/10.34984/scftp.2018.13.2.003.
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С использованием метода классической молекулярной динамики исследована селективная сольватация молекул гидроксибензойных кислот (орто-, мета- и пара-гидроксибензойной, протокатеховой, галловой, сиреневой) и гидроксикоричных кислот (пара-кумаровой, кофейной) полярным сорастворителем (метанол) в среде сверхкритического диоксида углерода при температуре 318 K., плотности 0,7 г/см и концентрации метанола 3,5 мольн. %. Предметом изучения являются локализация сорастворителя в ближайшем окружении растворенного вещества, образование кластеров сорастворителя вокруг растворенного вещества, число и характер водородных связей между молекулами растворенного вещества и сорастворителя, особенности структуры водородносвязанных комплексов, связанные с молекулярным строением растворенного вещества (количеством и расположением гидроксильных групп, замещением гидроксильных водородов метальными фрагментами, наличием этиленовой группы). Selective solvation of hydroxybenzoic (ortho-, meta- and para-hydroxybenzoic, protocatechuic, gallic, syringic) acids and hydroxycinnamic (para-coumaric, caffeic) acids by polar cosolvent (methanol) in supercritical carbon dioxide at temperature 318 K., solvent density 0.7 g/cm and methanol concentration 3.5 mol. % is studied using molecular dynamics method. The subject of the study is the formation of cosolvent clusters around solute, the solute - cosolvent hydrogen bonding, the structural features of hydrogen-bonded complexes associated with the molecular structure of solute (the number and location of hydroxyl groups, the substitution of hydroxyl hydrogens by methyl groups, and the presence of ethylene group between carboxyl group and benzene ring).
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Tian, Wenfei, Fengju Wang, Kaijie Xu, et al. "Accumulation of Wheat Phenolic Acids under Different Nitrogen Rates and Growing Environments." Plants 11, no. 17 (2022): 2237. http://dx.doi.org/10.3390/plants11172237.
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The health benefits of whole wheat grains are partially attributed to their phenolic acid composition, especially that of trans-ferulic acid (TFA), which is a powerful natural antioxidant. Breeders and producers are becoming interested in wheat with enhanced health-promoting effects. This study investigated the effects of different nitrogen (N) application rates (0, 42, 84, 126, and 168 N kg ha−1) on the phenolic acid composition of three wheat varieties in four locations for two years. The results indicate that the different N rates did not affect the TFA concentration but that they significantly affected the concentrations of para-coumaric acid, sinapic acid, and cis-ferulic acid in the wheat grains. A statistical analysis suggested that the wheat phenolic acid composition was predominantly determined by wheat variety, though there existed some interaction effect between the wheat variety and environments. The TFA concentration of the variety Jimai 22 was generally higher (with a mean value of 726.04 µg/g) but was easily affected by the environment, while the TFA concentration of the variety Zhongmai 578 (with a mean value of 618.01 µg/g) was more stable across the different environments. The results also suggest that it is possible to develop new wheat varieties with high yield potential, good end-use properties, and enhanced nutraceutical values.
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Karimov, O. K., G. Y. Kolchina, G. A. Teptereva, I. A. Chetvertneva, E. K. Karimov, and A. R. Badretdinov. "The reactivity of cinnamic acid derivatives as lignin precursors." Fine Chemical Technologies 15, no. 4 (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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Blinova, Irina P., Tatiana E. Nuzhnykh, Victor I. Deineka, Ludmila A. Deineka, and Anh Van Nguyen. "DETERMINATION OF ANTIOXIDANT PROPERTIES OF SUBSTANCES USING REDUCTION OF IRON (III) COMPLEX WITH 2,2′-DIPYRIDINE." ChemChemTech 68, no. 6 (2025): 6–14. https://doi.org/10.6060/ivkkt.20256806.7182.
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It has been shown that to obtain reliable results when determining antioxidant properties using the iron-reducing technique in samples for measuring optical density, it is necessary to create a ratio of the molar concentrations of iron (III) ions to the concentration of dipyridine in a molar ratio of about 1: 6.4. This is due to the low rate of ligand exchange for intraorbital low-spin octahedic complexes with configurations (t2g)5 and (t2g)6, for the initial iron (III) complex and the final reduction product, since product of reduction coordinats three dipyridine molecules instead of one or two in the case of the original complex. It has been experimentally established that the transfer of this ligand from the initial particle to the reduction product ([Fe(dipy)3]2+) occurs slowly. A simple calibration of the oxidant-antioxidant system in this case allows one to recalculate the antioxidant property by the number of moles of electrons lost by one mole of antioxidant. This in turn allows us to estimate the depth of transformation - the number of successive oxidation stages, i.e. antioxidant capacity of the original antioxidant. An analysis of the antioxidant capacity of some substances taken to express antioxidant properties as reference substances was performed. It has been established that one mole of ascorbic acid in this version of determining antioxidant properties quickly loses two moles of electrons, and the reaction practically ends. Caffeic acid also loses two electrons but much more slowly, and the process continues through the second stage. In this case, para-coumaric acid oxidizes extremely slowly compared to caffeic acid. The addition of the ortho position from the hydroxyl group of coumaric acid the methoxy group accelerates oxidation, and the addition of two methoxy groups at both ortho positions results in oxidation activity even greater than that of caffeic acid. In this case, ferulic, caffeic and sinapic acids can be used as substances to compare the antioxidant properties of slowly oxidizing (after an initial rapid period) mixture of substances in real extracts. When using caffeic acid as a comparison sample when determining the antioxidant properties of coffee (drink), obtained results are only slightly dependent on the exposure time of the reaction mixtures, even with constantly changing optical density. For citation: Blinova I.P., Nuzhnykh T.E., Deineka V.I., Denyeka L.A., Anh Van Nguyen Determination of antioxidant properties of substances using reduction of iron (III) complex with 2,2′-dipyridine. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2025. V. 68. N 6. P. 6-14. DOI: 10.6060/ivkkt.20256806.7182.
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Galeana-López, José Andrés, Crisantema Hernández, Nayely Leyva-López, Cynthia Esmeralda Lizárraga-Velázquez, Erika Yazmín Sánchez-Gutiérrez, and José Basilio Heredia. "Corn husk extracts as an antioxidant additive in diets for Nile tilapia (Oreochromis niloticus) fingerlings: Effect on growth performance, feed intake and toxicity//Extractos de hoja de mazorca de maíz como aditivo antioxidante en dietas para juveniles de tilapia del Nilo (Oreochromis niloticus): Efectos sobre el crecimiento, el consumo de alimento y la toxicidad." Biotecnia 22, no. 2 (2020): 147–54. http://dx.doi.org/10.18633/biotecnia.v22i2.1256.
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Corn stover, a corn harvest by-product, can be used to add value to feeds for farmed fish through their extracts, which are rich in phenolic compounds (PCs) and could confer antioxidant properties and possible health benefits to fish. In this study, PCs from corn husk extracts (CHE) were identified by ultra performance liquid chromatography-electrospray ionization-quadrupole time of fly-mass spectroscopy (UPLCESI-Q-ToF-MS/MS), and used to provide antioxidant potential to diets for Nile tilapia fingerlings. Three experimental diets for tilapia were formulated with 0, 100 and 200 mg PCs from CHE/kg feed and their antioxidant capacity was determined by DPPH• and ORAC assays. A total of 180 Nile tilapia fingerlings (0.35 ± 0.06 g) were fed for 14 days to determine the effect of experimental diets on feed intake and growth performance. PCs from CHE such as ferulic, p-coumaric and chlorogenic acids were the most abundant. The inclusion of PCs into tilapia diets increases linearly (p < 0.05) their antioxidant capacity (DPPH and ORAC). Growth performance and feed intake increased linearly (p < 0.05) as the level of CHE inclusion increased. Results suggest that the CHE can provide antioxidant potential to tilapia diets, promote growth performance and feed intake without toxic effects.RESUMENLa mazorca de maíz, un subproducto de la cosecha de maíz, puede usarse para agregar valor a los alimentos para peces de cultivo a través de sus extractos, que son ricos en compuestos fenólicos (PCs) y los cuales podrían conferir propiedades antioxidantes y posibles beneficios a la salud de los peces. En este estudio, las PCs de los extractos de cáscara de maíz (CHE) se identificaron mediante cromatografía líquida de ultra resolución-tiempo de vuelo con cuadrupolo acoplado a espectrometría de masas con ionización por electrospray (UPLC-ESI-Q-ToF-MS/MS), y se utilizaron para proporcionar potencial antioxidante a las dietas para alevines de tilapia del Nilo. Se formularon tres dietas experimentales para tilapia con 0, 100 y 200 mg de PCs de CHE/kg de alimento y su capacidad antioxidante se determinó mediante ensayos DPPH• y ORAC. Se alimentaron un total de 180 alevines de tilapia del Nilo (0.35 ± 0.06 g) durante 14 días para determinar el efecto de las dietas experimentales, sobre el consumo de alimento y el crecimiento. Los PCs de CHE como los ácidos ferúlico, p-cumárico y clorogénico fueron las más abundantes. La inclusión de PCs en las dietas para tilapia, aumenta linealmente (p <0.05) su capacidad antioxidante (DPPH• y ORAC). El crecimiento y el consumo de alimento aumentaron linealmente (p <0.05) a medida que aumentó el nivel de inclusión de CHE. Los resultados sugieren que el CHE puede proporcionar potencial antioxidante a las dietas para tilapia y promover el crecimiento y el consumo de alimento de esta especie sin efectos tóxicos.
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Busto, Eduardo, Michaela Gerstmann, Felix Tobola, Edmund Dittmann, Birgit Wiltschi, and Wolfgang Kroutil. "Systems biocatalysis: para-alkenylation of unprotected phenols." Catalysis Science & Technology 6, no. 22 (2016): 8098–103. http://dx.doi.org/10.1039/c6cy01947a.
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Commercially available phenol derivatives were transformed with pyruvate to form a new C–C bond leading to the correspondingpara-coumaric acids and only one molecule of water as an innocent side product in buffer.
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Mahmoudi, Maher, Fayçal Boughalleb, Mahmoud Mabrouk, and Raoudha Abdellaoui. "Phytochemical profile, antioxidant properties and protein contents of Astragalus tenuifoliosus seeds." Journal of the Mexican Chemical Society 67, no. 1 (2023): 24–32. http://dx.doi.org/10.29356/jmcs.v67i1.1854.
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Fabaceae seeds are reported to be used for varying medicinal and pharmaceutical purposes. However, knowledge of the nutritive value of Astragalus tenuifoliosus seeds is largely based on very limited data and remains unexplored, we report here the protein content, phenolics as well as the antioxidant potential of plant seeds to give adequate information on its suitability as a new source of natural bioactive compounds. The protein content was determined using the Kjeldahl and Bradford assays. The phytochemical contents were evaluated, and the extracts were further subjected to high-performance liquid chromatography-electrospray ionization – mass spectrometry (HPLC-ESI-MS) analysis. The antioxidant potential was evaluated using the total antioxidant capacity and the free DPPH radical scavenging activity. The results obtained from the protein analysis showed that the total content was 59.43 % of the dry matter basis. The globulins constituted the dominant fraction and followed by albumins, glutelins, and prolamins. The phytochemical investigation showed considerable amounts of polyphenol, flavonoid and condensed tannin amounts. The LC-ESI/MS analysis revealed the presence of 18 phenolics including 8 phenolic acids and 10 flavonoids mostly predominated by quinic acid (255.4 µg g-1 DW), p-coumaric acid (65.39 µg g-1 DW), quercetin (97.21 µg g-1 DW), and cirsiliol (29 µg g-1 DW). The seeds possessed strong antioxidant potential evidenced by their DPPH radical scavenging activities and total antioxidant capacity. The obtained findings contribute to the limited bibliographic information concerning A. tenuifoliosus seeds and represent a starting point to evaluate its potential as a valuable source of proteins, natural antioxidants, and safe bioactive compounds. Resumen. Las semillas de las Fabaceae se utilizan para diversos fines medicinales y farmacéuticos. Sin embargo, el conocimiento del valor nutritivo de las semillas de Astragalus tenuifoliosus se basa en gran medida en datos muy limitados y sigue sin explorarse. Aquí se reporta el contenido de proteínas, fenoles y el potencial antioxidante de las semillas de plantas para brindar información adecuada sobre su idoneidad como nueva fuente de compuestos bioactivos naturales. El contenido de proteína se determinó utilizando los ensayos de Kjeldahl y Bradford. Se evaluaron los contenidos fitoquímicos y los extractos se sometieron a análisis de cromatografía líquida de alto rendimiento, ionización por electropulverización y espectrometría de masas (HPLC-ESI-MS). El potencial antioxidante se evaluó utilizando la capacidad antioxidante total y la actividad de captación de radicales libres DPPH. Los resultados obtenidos del análisis de proteína mostraron que el contenido total fue de 59.43% con base en el peso seco. Las globulinas constituyeron la fracción dominante, seguidas por las albúminas, las glutelinas y las prolaminas. La investigación fitoquímica mostró cantidades considerables de polifenoles, flavonoides y taninos condensados. El análisis medinate LC-ESI/MS reveló la presencia de 18 fenoles, incluidos 7 ácidos fenólicos y 11 flavonoides, predominando en su mayoría el ácido quínico (255.4 µg g-1 DW), el ácido p-cumárico (65.39 µg g-1 DW), la quercetina (97.21 µg g-1 DW), y el cirsiliol (29 µg g-1 DW). Las semillas poseen un fuerte potencial antioxidante, evidenciado por sus actividades de eliminación de radicales DPPH y su capacidad antioxidante total. Los hallazgos obtenidos contribuyen a la limitada información bibliográfica sobre las semillas de A. tenuifoliosus y representan un punto de partida para evaluar su potencial como fuente valiosa de proteínas, antioxidantes naturales y compuestos bioactivos seguros.
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Szeląg, Małgorzata, Alicja Urbaniak, and Hans A. R. Bluyssen. "A theoretical antioxidant pharmacophore for natural hydroxycinnamic acids." Open Chemistry 13, no. 1 (2015). http://dx.doi.org/10.1515/chem-2015-0001.
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AbstractThe structure-activity relationship analysis has been performed for trans- and cis-hydroxycinnamic acids, to determine their theoretical antioxidant pharmacophore. Based on the detailed conformational studies, the most stable rotamers have been selected. We have analyzed the descriptors of four antioxidant mechanisms important in free radical scavenging: hydrogen atom transfer, sequential proton loss electron transfer, single electron transfer - proton transfer and transition metal chelation, based on the B3LYP/6-311++G(2d,2p) calculations in vacuum and polar media. The results explain the activity difference between cinnamic acid and its derivatives. The descending order of antioxidant potential is as follows: caffeic > sinapinic ~ ferulic > p-coumaric > o-coumaric > m-coumaric ~ phenol. The results have shown that transisomers indicate higher reactivity than cis- and may be considered as good antioxidants. It has been determined that the highest antioxidant ability is related to the hydroxyl group in para position, supported by planar structure and stability of radical forms. π-Type delocalization of unpaired electron on aromatic ring, double bond and para O-atom is the key to radical stabilization. The ortho-dihydroxy substitution in benzene ring positively influences the ability to neutralize free radicals and makes caffeic acid the antioxidant pharmacophore of hydroxycinnamic acids.
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Editors, Smujo, AUGUSTU A.M. DOLLY, AHMAD CHEIKHYOUSSEF, and MARTHA KANDAWA-SCHULZ. "Phenolic compounds from selected Namibian leafy vegetables: Extraction and characterization." Biofarmasi Journal of Natural Product Biochemistry 17, no. 1 (2019). http://dx.doi.org/10.13057/biofar/f170101.
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Abstract. Dolly AAM, Cheikhyoussef A, Kandawa-Schulz M. 2018. Phenolic compounds from selected Namibia leafy vegetables: Extraction and characterization. Biofarmasi J Nat Prod Biochem 16: 1-16. The objective of this project was to study the antioxidant potential of selected Namibian Leafy Vegetables (NLV). We measured Total Phenolic Content (TPC), Total Flavonoid contents (TFC), antioxidant activity against Diphenyl-1-picrylhydrazyl (DPPH), 2,2-azino- bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), as well as Reducing Power (RP) assays. The study further detects and characterize eight phenolic acids (4- hydroxybenzoic, trans-ferulic, gallic, vanillic, sinapic, syringic, and para-coumaric acids) using Gas Chromatography-Mass Spectrometry (GC-MS). Thirteen leafy vegetables taken from Kavango East Region were known as Hibiscus sabdariffa, Hibiscus cannabinus, Aeschynomene nambalensis, Oxygonum delagoense, Amaranthus hypochondriacus, Amaranthus thunbergii, Vigna unguiculata, Cucurbita maxima, Cleome gynandra, Lagenaria siceraria, Aeschynomene fluitans, Citrullus lanatus, and Corchorus tridens. The leaves were extracted using aqueous methanol, ethanol and acetone solvents. Acid and Base hydrolyzes for extraction of bound phenolic acids which were analyzed by GC-MS. The best results for each assay were as follows: TPC in methanol: 333.8±2.7µgGAE/g in H. sabdariffa. TFC in methanol: 166.0±0.6µgQE/g in A. nambalensis. DPPH assay in methanol: 79.3±0.6% in H. cannabinus. ABTS assay in ethanol: 98.8±0.2% in H. sabdariffa. RP assay in ethanol: 1227.5±106.2% of L. siceraria. The GC-MS detected phenolic acids in twenty extracts of Base Hydrolysed Samples (BHS), seven extracts of Acid Hydrolysed Samples (AHS) and thirteen extracts of Non-Hydrolysed Samples (NHS). BHS yielded the most significant amount of phenolic acids among the three extraction methods, with highest yields of p-coumaric acid in A. nambalensis (53.1µg/g). Results obtained from the TPC, TFC, and antioxidant assays demonstrated that the selected NLVs are potential sources of phenolic compounds and antioxidants. GC-MS analysis suggests that this tool is useful for characterizing phenolic acids. These findings have contributed to our understanding of the phytochemical contents of the selected NLVs, and further studies are necessary for the possible industrial application of the identified phenolic acids.
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Banerjee, Biswajit, Tripti Sharma, Sabyasachi Banerjee, Subhasis Banerjee, and Arijit Mondal. "Synthesis and Anticancer Activity of Metformin‐Phenolic Acid Conjugates." Chemistry & Biodiversity, February 16, 2025. https://doi.org/10.1002/cbdv.202403199.
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The leading cause of death worldwide is cancer. Several studies suggest phenolic acids and metformin as potential cancer treatment options because of their biological and therapeutic properties. So, we synthesized some novel metformin‐phenolic acid conjugates. We used an acid‐base neutralization method to extract the metformin‐free base. N, N`‐dicyclohexylcarbodiimide (DCC)‐4‐dimethylaminopyridine (DMAP) coupling of phenolic/aromatic acids (benzoic acid, cinnamic acid, caffeic acid, ferulic acid, gallic acid, para‐hydroxybenzoic acid, para coumaric acid, protocatechuic acid, salicylic acid, and vanillic acid) with metformin was performed to produce metformin phenolic acid conjugates (M1‐M10). We evaluated the structures using 1H‐NMR, 13C‐NMR, FT‐IR, and MS. All newly synthesized metformin phenolic acid conjugates were evaluated for their in vitro anti‐cancer activity. Metformin phenolic acid conjugates were synthesized and showed a range of inhibitory effects. The metformin‐caffeic acid conjugate [(E)‐3‐(3,4‐dihydroxyphenyl)‐N‐(N,N‐dimethylcarbamimidoyl)carbamimidoyl)acrylamide] (M3) (IC50: 5.47±2.72 μg/ml and 4.42±2.15 μg/ml) showed the best anticancer activity against MDA‐MB‐468 and A549 cancer cell lines.
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Myrtollari, Kamela, Andrea M. Chánique, Daniel Kracher, et al. "Engineering substrate acceptance of Resveratrol O‐Methyltransferase from Vitis vinifera for the selective synthesis of O‐methyl protected biobased hydroxystyrenes." ChemCatChem, April 24, 2025. https://doi.org/10.1002/cctc.202402027.
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Enzymatic decarboxylation of phenolic acids enables the production of biobased phenolic styrenes under mild reaction conditions. However, the free para‐phenolic group can lead to undesirable side products during polymerization, giving protection of the free phenolic OH group critical importance for the application in adhesives. Here we present a one‐pot two‐step cascade reaction, in which phenolic acid decarboxylase from Bacillus subtilis (BsPAD) catalyzes the decarboxylation of coumaric acid, caffeic acid, ferulic acid, and sinapic acid, followed by O‐methylation of the intermediate phenolic styrenes by resveratrol O‐methyltransferase from Vitis vinifera (VvROMT). The reaction sequence avoids the isolation and purification of the reactive intermediate hydroxystyrenes. Characterization of variants with amino acid substitution in the active‐site cavity led to the identification of mutants without activity towards the four phenolic acids. This avoids undesired O‐methylation of the starting material, which is not desirable since the decarboxylase does not convert the formed p‐methoxyphenolic acids. Furthermore, variation of amino acids in the active site led to the identification of mutants with improved activity for all four phenolic styrenes. The results constitute an important step towards the synthesis of biomass‐derived methoxy styrene derivatives whose photopolymerization yields polymers with outstanding adhesion properties.
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Ebadi, Mostafa, Fatemeh Ahmadi, Hossein Tahmouresi, Mohammad Pazhang, and Saeed Mollaei. "Investigation the biological activities and the metabolite profiles of endophytic fungi isolated from Gundelia tournefortii L." Scientific Reports 14, no. 1 (2024). http://dx.doi.org/10.1038/s41598-024-57222-8.
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AbstractEndophytic fungi are microorganisms that are considered as a potential source of natural compounds, and can be applied in various industries. The aims of this research were molecular identification of endophytic fungi isolated from the Gundelia tournefortii stems, and investigation their biological activities as well as phenolic and fatty acid profile. Surface sterilized stems of G. tournefortii were placed on potato dextrose agar (PDA) to isolate the fungal endophytes. Genomic DNA was extracted by CTAB method, and PCR amplification was performed by ITS 1 and ITS 4 as primers. The enzyme production of endophytic fungi was determined based on the formation of a clear zone that appeared around the colonies of fungus. The anti-oxidant activity was evaluated by measuring the amount of free radicals DPPH. Also, the total phenol and flavonoid contents were measured obtained by Folin-Ciocalteu and aluminum chloride colorimetric methods, respectively. Moreover, the separation and identification of phenolic acids and fatty acids were done by HPLC and GC, respectively. Phylogenetic analysis was done based on the Internal Transcribed Spacer (ITS) region, and five isolates were identified as following: Aspergillus niger, Penicillium glabrum, Alternaria alternata, A. tenuissima, and Mucor circinelloides. Evaluation of the enzymatic properties showed that P. gabrum (31 ± 1.9 mm), and A. niger (23 ± 1.7) had more ability for producing pectinase and cellulase. The anti-oxidant activity of isolates showed that A. alternata extract (IC50 = 471 ± 29 µg/mL) had the highest anti-oxidant properties, followed by A. tenuissima extract (IC50 = 512 ± 19 µg/mL). Also, the extract of A. alternata had the greatest amount of total phenols and flavonoids contents (8.2 ± 0.4 mg GAL/g and 2.3 ± 0.3 mg QE/g, respectively). The quantification analysis of phenolic acid showed that rosmarinic acid, para-coumaric acid, and meta-coumaric acid (42.02 ± 1.31, 7.53 ± 0.19, 5.41 ± 0.21 mg/g, respectively) were the main phenolic acids in the studied fungi. The analysis of fatty acids confirmed that, in all fungi, the main fatty acids were stearic acid (27.9–35.2%), oleic acid (11.3–17.3%), palmitic acid (16.9–23.2%), linoleic acid (5.8–11.6%), and caprylic acid (6.3–10.9%). Our finding showed that endophytic fungi are a source of bioactive compounds, which could be used in various industries. This is the first report of endophytic fungi associated with G. tournefortii, which provides knowledge on their future use on biotechnological processes.
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Burhanoğlu, Tülin, Zehra Seda Halbutoğulları, Gulseren Turhal, and Asuman Demiroglu-Zergeroglu. "Evaluation of the anticancer effects of hydroxycinnamic acid isomers on breast cancer stem cells." Medical Oncology 42, no. 3 (2025). https://doi.org/10.1007/s12032-025-02618-3.
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Abstract Research on breast cancer stem cells (BCSCs) is crucial for improving our understanding of their roles in tumor resistance, metastasis, and relapse. This study investigated the anti-cancer effects of two isomers of hydroxycinnamic acids (HCA): para-coumaric acid (PCA) and ortho-coumaric acid (OCA) on breast cancer stem cells (BCSCs). The isolated and characterized stem cells contained CD44 + /CD24 surface markers, exhibited high levels of aldehyde dehydrogenase activity, and were able to form mammospheres. The evaluation of HCAs on stem cell proliferation, cell cycle, and apoptosis was conducted by comparing them with MCF-7, the luminal breast cancer cell line. The viability and immunoblot analyses demonstrated that HCA applications resulted in a dose-dependent decrease in the number of viable cells and inhibited phosphorylation of Extracellular regulated kinases 1/2 (ERK1/2). These findings were supported by the detection of suppressed colony formation and delayed wound-healing in HCA-exposed cells. E-cadherin expression increased in OCA-treated cells. Additionally, the arrest of G1/S phase progression and the downregulation of Cyclin D1 expression exhibited that OCA and PCA-induced cytostatic effects in BSCS cells. After treatment, the increased Annexin-V/7-AAD staining, along with elevated expression of caspase-3/7 and a decreased Bcl-2/Bax ratio, indicated apoptosis mediated by the activation of Janus kinase (JNK) and p38 Mitogen-activated kinase (p38 MAPK). In conclusion, both OCA and PCA exhibit anti-carcinogenic potential on BCSCs; However, OCA has a stronger effect and is becoming a promising candidate for further research.
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Möller, Svenning R., Christopher S. Lancefield, Nicola C. Oates, et al. "CRISPR/Cas9 suppression of OsAT10, a rice BAHD acyltransferase, reduces p-coumaric acid incorporation into arabinoxylan without increasing saccharification." Frontiers in Plant Science 13 (July 22, 2022). http://dx.doi.org/10.3389/fpls.2022.926300.
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Ester-linked hydroxycinnamic acids ferulic acid (FA) and para-coumaric acid (p-CA) play important roles in crosslinking within cell wall arabinoxylans (AX) and between AX and lignin in grass cell walls. The addition of hydroxycinnamates to AX, is mediated by the Mitchell clade of BAHD acyl-coenzyme A-utilizing transferases. Overexpression of OsAT10 (a Mitchell clade BAHD acyl transferase) in rice, has previously been shown to increase p-CA content in AX in leaves and stems, leading to increased cell wall digestibility, potentially associated with a concomitant decrease in FA content. To investigate the physiological role of OsAT10 we established CRISPR/Cas9 rice knock-out mutants devoid of OsAT10. Our analysis of hydroxycinnamic acid content in wild type plants revealed that AX associated p-CA is found almost exclusively in rice husks, with very little found in other tissues. Mutant plants were essentially devoid of ester-linked p-CA associated with AX, indicating that OsAT10 represents the major enzyme responsible for the addition of p-CA to arabinoxylan in rice plants. We found no change in the digestibility of rice husk lacking AX-associated p-CA, suggesting that the changes in digestibility seen in OsAT10 overexpressing plants were solely due to compensatory decreases in AX-associated FA.
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El Amri, Nidal, Rachida Chabir, Rabie Kachkoul, and Abdellatif Bour. "Phenolic Composition and Phytochemical Analysis of Moroccan Raw and Processed Capparis spinosa Buds and Berries." Chemistry & Biodiversity, May 22, 2025. https://doi.org/10.1002/cbdv.202500443.
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ABSTRACTCapparis spinosa, also known as spiny caper, is a widely distributed plant in Mediterranean regions, valued for its nutritional and medicinal properties. Its richness in bioactive compounds, particularly polyphenols, makes it a subject of interest for various therapeutic applications. This study aims to characterize the phenolic compounds present in raw and processed caper buds and berries and evaluate their antioxidant potential. The identification of phenolic compounds, performed by ultra‐high‐performance liquid chromatography coupled with mass spectrometry, revealed the presence of flavonoids, mainly flavonols (rutin, quercetin, kaempferol, myricetin, and isorhamnetin), as well as phenolic acids such as sinapic acid, para‐coumaric acid, ferulic acid, and vanillic acid. The results of the spectrophotometric quantification of total polyphenols and total flavonoids showed that raw capers contain the highest concentrations of polyphenols and flavonoids, with values ranging between 86.19 mg gallic acid equivalent/g DW and 31.29 mg quercetin equivalent/g DW, respectively. Fermented caperberries present the lowest concentrations. The evaluation of the antioxidant potential, performed by in vitro 2,2‐diphenyl‐1‐picrylhydrazyl and ferric reducing antioxidant power tests, demonstrated strong antioxidant activity in different extracts, particularly in raw capers, which is correlated with their high content of phenolic compounds. These findings highlight the potential of Moroccan C. spinosa as a natural source of antioxidants, with possible applications in the development of functional foods, nutraceuticals, and natural health products.
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Anjum, Varisha, Faraat Ali, Sweta Joshi, Areefa Anjum, and Asad Ali. "Synergistic effect of myricetin and phenolic acid derivatives on reversal of dengue fever related thrombocytopenia and its pharmacokinetics study in Plasma by using HPLC and UPLC-Q-TOF." Current Drug Metabolism 21 (November 10, 2020). http://dx.doi.org/10.2174/1389200221666201110155119.
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Background: Carica papaya L. is consumed worldwide because of its high nutritional and medicinal benefits due to the presence of polyphenols. Objective: The present study was undertaken to investigate the effects of polyphenols present in C. papaya in dengue fever against cyclophosphamide (CP) induced thrombocytopenia in balb/c mice. Method: Platelet count (PC), total leukocyte count (TLC), activated partial thromboplastin time (aPTT), prothrombin time (PT), anti-platelet antibodies IgG and IgM were analysed in blood/serum of animals treated for 21 days with standardized C. papaya leaf juice (CPLJ) and its bioactivity guided selected fractions (SFs). A new HPLC-PDA method was developed to study pharmacokinetic (PK) profile of phytoconstituents in plasma of bioactive butanol fraction (BBF) and CPLJ treated mice. CPLJ and BBF were metabolically distinguished by UPLC-qTOF/MS for metabolite signature. Results: Animals orally treated with BBF elicited significant reduction in blood/serum levels of aPTT, PT, AST, ALT and antibodies IgG and IgM. However, thrombocyte count was significantly (p<0.01) increased. A total of 12 and 9 metabolites were tentatively identified using UPLC-qTOF/MS in BBF and CPLJ, respectively. PK parameters evaluated by noncompartmental model showed Cmax of plant flavonoids and phenolic acids including caffeic acid, para-coumaric acid, vanillic acid, myricetin and trans-ferulic acid (0.10, 0.49, 0.61, 5.97, 36.29 µg/mL, respectively) and half-life (24, 6, 26, 15 and 13 h), respectively. Conclusion: Collectively, our data suggest that the polyphenol enriched fraction of CPLJ might reverse acute thrombocytopenia by accelerating the platelets regeneration from megakaryocytes, providing strong rational for its use in the treatment of dengue fever-related thrombocytopenia. Thus, the BBF can be used as phytopharmaceuticals for the enhancement of platelets by using as adjuvants or alone.