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1
Kraut, Ludwig, Rainer Klein, and Rüdiger Mues. "Flavonoid Diversity In The Liverwort Genus Monoclea Hooker*." Zeitschrift für Naturforschung C 47, no. 11-12 (December 1, 1992): 794–99. http://dx.doi.org/10.1515/znc-1992-11-1203.
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Many samples of Monoclea gottschei from Central and South America and the Caribbean Islands have been compared for their flavonoids. The species exhibits the most diverse flavonoid pattern ever observed for a liverwort. From different chemotypes 28 flavones were isolated: 8 aglycones, 3 monoglycosides, 9 diglycosides, 6 triglycosides and 2 oligo- or polyglycosides. The chromatographic and spectroscopic data of previously unidentified compounds are presented. Samples of M . forsteri from New Zealand have been analyzed for flavonoids too, but their flavone patterns are much less diverse: 1 aglycone, 1 polyglycoside and 2 further mono-or-diglycosides were isolated. The differences in flavonoid production of both species are an additional feature for the distinction of the two Monoclea species
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Joshi, Kunjani. "Leaf Flavonoid Patterns in the Species of Stemonoporus (Dipterocarpaceae) and Their Taxonomic Significance." Journal of Natural History Museum 24 (October 9, 2009): 146–55. http://dx.doi.org/10.3126/jnhm.v24i1.2291.
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During the chemotaxonomic study of 16 species of Stemonoporus, three flavonoid aglycones (flavonol quercetin, flavonol kaempferol and flavone apigenin) and glycosides (quercetin 3- glucoside, quercetin 3-rutinoside and apigenin 5-glucoside) were isolated while flavonol myricetin, flavone luteolin and proanthcyanidin were not detected in any of the species surveyed. The isolated flavonoids can be used as chemotaxonomic markers. The species of Stemonoporus can be regarded as advanced in flavonoid pattern because of the absence of myricetin and loss of proanthocyanidins. The data of the flavonoid patterns and the outcome of cluster analysis are taxonomically useful to resolve the controversies over the systematic arrangement of the species and suggest the need for a revision of classification of the genus Stemonoporus. Key words: Dipterocarpaceae; Flavonols; Chemotaxonomy; Cluster analysis. Journal of Natural History MuseumVol. 24, 2009Page: 146-155
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Knüttel, Helge, and Konrad Fiedler. "Host-plant-derived variation in ultraviolet wing patterns influences mate selection by male butterflies." Journal of Experimental Biology 204, no. 14 (July 15, 2001): 2447–59. http://dx.doi.org/10.1242/jeb.204.14.2447.
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SUMMARY We report on the first case in which sequestered secondary plant compounds determine an insect’s external appearance in the ultraviolet spectrum and thereby influence visually mediated mate choice. Larvae of the common blue butterfly Polyommatus icarus specifically sequester flavonoids in different amounts and types, depending on the part or species of food plant. During late pupal development the majority of ultraviolet-absorbing flavonoids are deposited in the wing scales. The flavonoid content of the larval diet thereby determines ultraviolet wing patterns. In laboratory and field experiments, male butterflies clearly preferred flavonoid-rich, ultraviolet-absorbing female dummies. This preference is mediated visually by the ultraviolet pattern of the wings. Food-plant parts and species vary in value as a food source, so ultraviolet wing patterns may signal mate quality and are not a species-specific characteristic. We discuss the use of principal component analysis in analysing spectral data in the context of visual communication. We propose the alternative application of confidence intervals of averaged spectra as a novel straightforward statistical method for comparing groups of spectra in a manner that is independent of assumptions about the visual system of the receiver. In addition, they can be used to give confidence intervals to derived measures of colour such as quantum catch by photoreceptors.
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Li, Chengshuai, Lijing Zhang, Decao Niu, Shuzhen Nan, Xiumei Miao, Xiaowei Hu, and Hua Fu. "Investigation of flavonoid expression and metabolite content patterns during seed formation of Artemisia sphaerocephala Krasch." Seed Science Research 31, no. 2 (June 2021): 136–48. http://dx.doi.org/10.1017/s096025852100012x.
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AbstractFlavonoids are a group of phenolic secondary metabolites in plants that have important physiological, ecological and economic value. In this study, using the desert plant Artemisia sphaerocephala Krasch. as the sample material, the content and components of the total flavonoids in its seeds at seven different developmental stages were determined. In addition, the genes involved in flavonoid metabolism were identified by full-length transcriptome sequencing (third-generation sequencing technology based on PacBio RS II). Their expression levels were analysed by RNA-seq short reading sequencing, to reveal the patterns and regulation mechanisms of flavonoid accumulation during seed development. The key results were as follows: the content of total flavonoids in mature seeds was 15.05 mg g−1, including five subclasses: flavonols, chalcones, flavones, flavanones and proanthocyanidins, among which flavonols accounted for 45.78%. The period of rapid accumulation of flavonoids was 40–70 d following anthesis. The high expression of phenylalanine ammonia-lyase (PAL), 4-coumarate-CoA ligase (4CL) and UDP-glucose:flavonoids 3-o-glucosyltransferase (UF3GT) promoted the accumulation of total flavonoids, while the high expression of flavonoids 3′-hydroxylase (F3′H) and flavonols synthase (FLS) made flavanols the main component. Transcription factors such as the MYB-bHLH-WDR (MBW) complex and Selenium-binding protein (SBP) directly regulated the structural genes of flavonoid metabolism, while C2H2-type zinc finger (C2H2), Zinc-finger transcription factor (GATA), Dehydration-responsive element binding (DREB), Global Transcription factor Group E protein (GTE), Trihelix DNA-binding factors (Trihelix) and Phytochrome-interacting factor (PIF) indirectly promoted the synthesis of flavonoids through hormones such as brassinoidsteroids (BRs) and abscisic acid (ABA). These results provided valuable resources for the application of related genes in genetics and breeding.
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Qi, Zengxing, Ran Zhao, Jing Xu, Yanrui Ge, Ruofan Li, and Ruili Li. "Accumulation Pattern of Flavonoids during Fruit Development of Lonicera maackii Determined by Metabolomics." Molecules 26, no. 22 (November 16, 2021): 6913. http://dx.doi.org/10.3390/molecules26226913.
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Lonicera maackii (Caprifoliaceae) is a large, upright shrub with fruits that contain many bioactive compounds. Flavonoids are common active substances in L. maackii. However, there is a dearth of information about the accumulation of these flavonoids and their possible medicinal value. We used targeted metabolomics analysis based on ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) to analyze five developmental stages of L. maackii fruit. A total of 438 metabolites were identified in the five developmental stages, including 81 flavonoids and derivatives. The 81 flavonoids included 25 flavones and derivatives, 35 flavonols and derivatives, two isoflavones, three cyanidins and derivatives, eight procyanidins, and eight flavanones. In addition, we outlined the putative flavonoid biosynthesis pathway and screened their upstream metabolites. More importantly, we analyzed the accumulation patterns of several typical flavones and flavonols. The results reported here improved our understanding of the dynamic changes in flavonoids during fruit development and contributed to making full use of the medicinal value of L. maackii fruit.
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Fathoni, Ahmad, Alhady Nareswara Candraditya, and Tarso Rudiana. "Antioxidant activity and identification of flavonoid compounds in Patat leaves (Phrynium capitatum) ethyl acetate extract." Jurnal Pendidikan Kimia 14, no. 3 (December 30, 2022): 149–56. http://dx.doi.org/10.24114/jpkim.v14i3.40595.
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Flavonoids are the biggest compound from the phenolic group that has the function of antioxidants. One of the plants with flavonoids is patat (Phrynium capitatum), which is usually used as food wrapping material. This study aims to quantify total flavonoid content, antioxidant activity and identify flavonoids from patat leaves ethyl acetate extract. Patat leaves sample cleaned, dried, and grinded. Grinded patat leaves were macerated gradually for 2 × 24 hours with n-hexane, ethyl acetate, and methanol solvent. The extract undergoing total flavonoids test guided with AlCl3 and CH3COONa. Extract with the biggest flavonoids content proceed to antioxidant activity test by SOD (superoxide dismutase) method and analyzed for the flavonoid structure by UHPLC MS/MS (ORBITRAP HRMS). The biggest total flavonoids are ethyl acetate extract with 8.678 mg QE/g; then methanol extract with 5.296 mg QE/g; and n-hexane extract was not tested because of negative results in the qualitative test. The antioxidant activity of the ethyl acetate extract of patat leaves is classified as inactive, with an Ic50 value of 488.299 ppm. The low antioxidant activity is due to the sample, which is still a matrix containing many compounds. The flavonoid compounds identified by its fragmentation pattern were kaempferide, formononetin, and pinostrobin.
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Depeint*, F., J. M. Gee, G. Williamson, and I. T. Johnson. "Evidence for consistent patterns between flavonoid structures and cellular activities." Proceedings of the Nutrition Society 61, no. 1 (February 2002): 97–103. http://dx.doi.org/10.1079/pns2001133.
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A wide variety of plant-derived compounds, including the polyphenolic flavonoids, is present in the human diet or is consumed for medicinal reasons. Epidemiological and animal studies tend to suggest a protective effect of flavonoids against cardiovascular diseases and some types of cancer. Although flavonoids have been studied for about 50 years, the cellular mechanisms involved in their biological activity are still largely unknown. Antioxidant properties of the flavonoids have been postulated as a mechanism for putative protective effect against cardiovascular disease. Nevertheless, these properties alone are not sufficient to explain the anti-carcinogenic potential of these polyphenols. The mechanisms by which the molecules interact with cells or are absorbed by them are very important for determining the intracellular concentration and distribution of the metabolites to internal organs. With the exception of the cells lining the gastrointestinal tract, all other cells in the body are only exposed to flavonoid metabolites and degradation products. No previous studies have addressed this aspect of cellular exposure, except for some methylated metabolites. Within the last decade, reports on flavonoid activities have been largely associated with enzyme inhibition and anti-proliferative activity. From our recent work on the human colon cancer cell line HT29 and comparison with published studies, structure–function relationships demonstrate that antioxidant, enzyme inhibitor or anti-proliferative activities are dependent on particular structure motifs. The present review also presents a summary of mechanistic data on a few selected compounds.
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Liu, Shengcai, Xiao Wang, and Liyun Peng. "Comparative Transcriptomic Analysis of the Metabolism of Betalains and Flavonoids in Red Amaranth Hypocotyl under Blue Light and Dark Conditions." Molecules 28, no. 15 (July 25, 2023): 5627. http://dx.doi.org/10.3390/molecules28155627.
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Amaranth plants contain abundant betalains and flavonoids. Anthocyanins are important flavonoids; however, they cannot coexist in the same plant with betalains. Blue light influences metabolite synthesis and hypocotyl elongation; accordingly, analyses of its effects on betalain and flavonoid biosynthesis in Amaranthus tricolor may provide insight into the distribution of these plant pigments. We analyzed the betalain and flavonoid content and transcriptome profiles in amaranth hypocotyls under blue light and dark conditions. Furthermore, we analyzed the expression patterns of key genes related to betalains and flavonoids. Amaranth hypocotyls were shorter and redder and showed higher betalain and flavonoid content under blue light than in dark conditions. Key genes involved in the synthesis of betalains and flavonoids were upregulated under blue light. The gene encoding DELLA was also upregulated. These results suggest that blue light favors the synthesis of both betalains and flavonoids via the suppression of bioactive gibberellin and the promotion of DELLA protein accumulation, which also suppresses hypocotyl elongation. The metabolite profiles differed between plants under blue light and dark conditions. These findings improve our understanding of the environmental cues and molecular mechanisms underlying pigment variation in Amaranthus.
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Tungmunnithum, Duangjai, Laurine Garros, Samantha Drouet, Natália Cruz-Martins, and Christophe Hano. "Extraction Kinetics and Reaction Rates of Sacred Lotus Stamen Tea Infusion-Derived Flavonoids in Relation with Its Antioxidant Capacity." Plants 11, no. 17 (August 29, 2022): 2234. http://dx.doi.org/10.3390/plants11172234.
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Stamen tea from Nelumbo nucifera Gaertn. (or the so-called sacred lotus) is widely consumed, and its flavonoids provide various human health benefits. The method used for tea preparation for consumption, namely the infusion time, may affect the levels of extractable flavonoids, ultimately affecting their biological effects. To date, there is no report on this critical information. Thus, this study aims to determine the kinetics of solid liquid extraction of flavonoid from sacred lotus stamen using the traditional method of preparing sacred lotus stamen tea. Phytochemical composition was also analyzed using high-performance liquid chromatography (HPLC). The antioxidant potential of stamen tea was also determined. The results indicated that the infusion time critically affects the concentrations of flavonoids and the antioxidant capacity of sacred lotus stamen tea, with a minimum infusion time of 5–12 min being required to release the different flavonoids from the tea. The extraction was modeled using second order kinetics. The rate of release was investigated by the glycosylation pattern, with flavonoid diglycosides, e.g., rutin and Kae-3-Rob, being released faster than flavonoid monoglycosides. The antioxidant activity was also highly correlated with flavonoid levels during infusion. Taken together, data obtained here underline that, among others, the infusion time should be considered for the experimental design of future epidemiological studies and/or clinical trials to reach the highest health benefits.
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Kim, Bo-Ram, Ah-Reum Han, and Ik-Soo Lee. "Microbial Transformation of Flavonoids in Cultures of Mucor hiemalis." Natural Product Communications 15, no. 12 (December 2020): 1934578X2097774. http://dx.doi.org/10.1177/1934578x20977743.
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Flavonoids are plant secondary metabolites that are well known for their health-promoting properties as nutraceuticals in diets. Bioavailability and biological activities of flavonoids vary among the individual subclasses with different patterns of substitution, inclusive of glycosylation, to their basic structures. Many flavonoids exist as glycosides in plants. This study investigated the possibility of glycosylation of flavonoids through biotransformation using filamentous fungi as whole-cell biocatalysts. Microbial transformations of ten flavonoids (four flavones, four flavonols, a flavanone, and an aurone) were performed in cultures of Mucor hiemalis KCTC 26779. As a result, a flavonoid glycoside was obtained which has not been described previously. The chemical structure of this product was elucidated as 6,2′-dimethoxyflavonol-3- O-β-d-glucopyranoside by analyzing 1-dimensional and 2-dimensional-nuclear magnetic resonance spectral and high-resolution electrospray ionization mass spectral data. This compound could be useful for further biological and bioavailability studies, as well as expanding the library of flavonoid derivatives.
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Gates, Paul J., and Norberto P. Lopes. "Characterisation of Flavonoid Aglycones by Negative Ion Chip-Based Nanospray Tandem Mass Spectrometry." International Journal of Analytical Chemistry 2012 (2012): 1–7. http://dx.doi.org/10.1155/2012/259217.
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Flavonoids are one of the most important classes of natural products having a wide variety of biological activities. There is wide interest in a range of medical and dietary applications, and having a rapid, reliable method for structural elucidation is essential. In this study a range of flavonoid standards are investigated by chip-based negative ion nanospray mass spectrometry. It was found that the different classes of flavonoid studied have a combination of distinct neutral losses from the precursor ion [M-H]−along with characteristic low-mass ions. By looking only for this distinct pattern of product ions, it is possible to determine the class of flavonoid directly. This methodology is tested here by the analysis of a green tea extract, where the expected flavonoids were readily identified, along with quercetin, which is shown to be present at only about 2% of the most intense ion in the spectrum.
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Yan, Heqin, Wei Zheng, Yong Wang, Yougen Wu, Jing Yu, and Pengguo Xia. "Integrative Metabolome and Transcriptome Analysis Reveals the Regulatory Network of Flavonoid Biosynthesis in Response to MeJA in Camelliavietnamensis Huang." International Journal of Molecular Sciences 23, no. 16 (August 19, 2022): 9370. http://dx.doi.org/10.3390/ijms23169370.
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Flavonoids are secondary metabolites widely found in plants, which perform various biological activities, such as antiinflammation, antioxidation, antitumor, and so on. Camellia vietnamensis Huang, a species of oil-tea Camellia tree, is an important woody oil crop species widely planted on Hainan Island, which provides health benefits with its high antioxidant activity and abundant flavonoid content. However, very little is known about the overall molecular mechanism of flavonoid biosynthesis in C. vietnamensis Huang. In this study, methyl jasmonate (MeJA) is used as an inducer to change the content of secondary metabolites in C. vietnamensis. Then, the potential mechanisms of flavonoid biosynthesis in C. vietnamensis leaves in response to MeJA were analyzed by metabolomics and transcriptomics (RNA sequencing). The results showed that metabolome analysis detected 104 flavonoids and 74 fatty acyls which showed different expression patterns (increased or decreased expression). It was discovered by KEGG analysis that three differentially accumulated metabolites (cinnamaldehyde, kaempferol and quercitrin) were annotated in the phenylpropanoid biosynthesis (ko00940), flavonoid biosynthesis (ko00941), and flavone and flavonol biosynthesis (ko00944) pathways. In the transcriptome analysis, 35 different genes involved in the synthesis of flavonoids were identified by MapMan analysis. The key genes (PAL, 4CL, CCR, CHI, CHS, C4H, FLS) that might be involved in the formation of flavonoid were highly expressed after 2 h of MeJA treatment. This study provides new insights and data supporting the molecular mechanism underlying the metabolism and synthesis of flavonoids in C. vietnamensis under MeJA treatment.
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Resende, Flávia Aparecida, Leonardo Gorla Nogueira, Tais Maria Bauab, Wagner Vilegas, and Eliana Aparecida Varanda. "Antibacterial potential of flavonoids with different hydroxylation patterns." Eclética Química Journal 40, no. 1 (September 26, 2015): 173. http://dx.doi.org/10.26850/1678-4618eqj.v40.1.2015.p173-179.
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The antibacterial activity of ten flavonoids, with variations in the hydroxylation pattern, was assayed in this study with the aim of investigating the influence of the hydroxyl groups of flavonoids on the evaluated activity. The evaluated degree of hydroxylation of the flavonoid molecules appears to have a crucial role in antibacterial effects. Kaempferol, the most active compound against Staphylococcus aureus, has a hydroxyl group in the B ring, a double bond between carbons 2 and 3 in conjunction with a 4-carbonyl group and hydroxyl groups at positions 3, 5 and 7, showing that the hydrophilic / lipophilic balance appears to be an important variable for antibacterial activity. With respect to the strain of Escherichia coli, the compounds evaluated did not inhibit completely bacterial growth; however they reduced the percentage of Gram-negative cells, under the conditions used in this work. These studies contribute to clarify the mechanisms by which these compounds act in the evaluated activity, since flavonoids can act through different mechanisms other than conventional antibiotics and could, therefore, be of use in the treatment of resistant bacteria.
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Wollenweber, Eckhard, Marion Dörr, Abdolhossein Rustaiyan, James N. Roitman, and Earl H. Graven. "Notes: Exudate Flavonoids of Some Salvia and a Trichostema Species." Zeitschrift für Naturforschung C 47, no. 9-10 (October 1, 1992): 782–84. http://dx.doi.org/10.1515/znc-1992-9-1025.
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Seven species of Salvia and one species of Trichostema were analyzed for their exudate flavonoids. They were found to exhibit flavonoid aglycones in various numbers and different patterns. Most of these are flavones, in which 6-methoxy-substituted compounds predominate.
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Shui, Lanya, Kaisen Huo, Yan Chen, Zilin Zhang, Yanfang Li, and Jun Niu. "Integrated metabolome and transcriptome revealed the flavonoid biosynthetic pathway in developing Vernonia amygdalina leaves." PeerJ 9 (April 26, 2021): e11239. http://dx.doi.org/10.7717/peerj.11239.
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Background Vernonia amygdalina as a tropical horticultural crop has been widely used for medicinal herb, feed, and vegetable. Recently, increasing studies revealed that this species possesses multiple pharmacological properties. Notably, V. amygdalina leaves possess an abundance of flavonoids, but the specific profiles of flavonoids and the mechanisms of fl avonoid bi osynthesis in developing leaves are largely unknown. Methods The total flavonoids of V. amygdalina leaves were detected using ultraviolet spectrophotometer. The temporal flavonoid profiles of V. amygdalina leaves were analyzed by LC-MS. The transcriptome analysis of V. amygdalina leaves was performed by Illumina sequencing. Functional annotation and differential expression analysis of V. amygdalina genes were performed by Blast2GO v2.3.5 and RSEM v1.2.31, respectively. qRT-PCR analysis was used to verify the gene expressions in developing V. amygdalina leaves. Results By LC-MS analysis, three substrates (p-coumaric acid, trans-cinnamic acid, and phenylalanine) for flavonoid biosynthesis were identified in V. amygdalina leaves. Additionally, 42 flavonoids were identified from V. amygdalina leaves, including six dihydroflavones, 14 flavones, eight isoflavones, nine flavonols, two xanthones, one chalcone, one cyanidin, and one dihydroflavonol. Glycosylation and methylation were common at the hydroxy group of C3, C7, and C4’ positions. Moreover, dynamic patterns of different flavonoids showed diversity. By Illumina sequencing, the obtained over 200 million valid reads were assembled into 60,422 genes. Blast analysis indicated that 31,872 genes were annotated at least in one of public databases. Greatly increasing molecular resources makes up for the lack of gene information in V. amygdalina. By digital expression profiling and qRT-PCR, we specifically characterized some key enzymes, such as Va-PAL1, Va-PAL4, Va-C4H1, Va-4CL3, Va-ACC1, Va-CHS1, Va-CHI, Va-FNSII, and Va-IFS3, involved in flavonoid biosynthesis. Importantly, integrated metabolome and transcriptome data of V. amygdalina leaves, we systematically constructed a flavonoid biosynthetic pathway with regards to material supplying, flavonoid scaffold biosynthesis, and flavonoid modifications. Our findings contribute significantly to understand the underlying mechanisms of flavonoid biosynthesis in V. amygdalina leaves, and also provide valuable information for potential metabolic engineering.
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Perrino, P., G. Maruca, V. Linsalata, V. V. Bianco, R. N. Lester, and V. Lattanzio. "Flavonoid taxonomic analysis of Vicia species of section Faba." Canadian Journal of Botany 67, no. 12 (December 1, 1989): 3529–33. http://dx.doi.org/10.1139/b89-434.
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The flavonoids rutin, quercitrin, hyperoside, quercetin-3-arabinoside, kaempferol-3-rutinoside, and robinin were identified in leaves of six Vicia species of section Faba. Flavonoid glycosidic pattern was utilized to draw taxonomical relationships amongst the six species. The four botanical varieties of Vicia faba were found to be distinct from the narbonensis group and Vicia bithynica. Indeed, flavonoid fingerprints using high performance liquid chromatography show that the four botanical varieties of V. faba L. are closely related, whereas the wild species separate into three subgroups.
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Kasaj, Denata, Liselotte Krenn, Gottfried Reznicek, Sonja Prinz, Antje Hüfner, and Brigitte Kopp. "Flavonoids in Achillea collina." Scientia Pharmaceutica 69, no. 1 (March 30, 2001): 75–83. http://dx.doi.org/10.3797/scipharm.aut-01-09.
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In a detailed study on the flavonoid pattern of Achillea collina BECKER ten flavonoids were isolated from a methanolic extract of aerial parts of the plant. Their structures were determined by UV, ESI-MS, GC-MS and NMR spectroscopic methods including 2D-NMR. Apigenin-7-O-rutinoside was proven for the first time in the genus Achillea.
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Wollenweber, Eckhard, Yoshinori Asakawa, Detlef Schillo, Ulrich Lehmann, and Heidrun Weigel. "A Novel Caffeic Acid Derivative and Other Constituents of Populus Bud Excretion and Propolis (Bee-Glue)." Zeitschrift für Naturforschung C 42, no. 9-10 (October 1, 1987): 1030–34. http://dx.doi.org/10.1515/znc-1987-9-1004.
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Abstract The bud exudates of Populus nigra, P. trichocarpa, and P. grandidentata × tremuloides were analyzed for the presence of phenolics and flavonoids. A novel natural product, caffeic acid y.y-dimethylallyl ester, was identified from P. nigra, along with further phenolics such as ρ-hydroxy-acetophenone, dimethyl caffeic acid, cinnamoyl cinnamata and vanillin. The flavonoid aglycones correspond to those reported earlier. Propolis samples from the Sonoran Desert were shown to exhibit the flavonoid pattern that is typical for poplar bud exudates, thus confirming this material as the major source for bee-glue. Only a single flavonoid might originate from the leaf exudate of a desert shrub.
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Wollenweber, Eckhard, Marion Dörr, Diego Rivera, and James N. Roitman. "Externally Accumulated Flavonoids in Three Mediterranean Ononis Species." Zeitschrift für Naturforschung C 58, no. 11-12 (December 1, 2003): 771–75. http://dx.doi.org/10.1515/znc-2003-11-1202.
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Abstract The Mediterranean Ononis species, O. fruticosa, O. natrix subsp. ramosissima and O. tridentata, have been analyzed for their exudate flavonoids. More than 20 flavonoid aglycones were identified, some of which are rather rare natural compounds. One of them, namely hypolaetin- 8,3′,4′-trimethyl ether, had been found only once before. The results are presented in a table along with literature data, and the chemotaxonomic impact of the flavonoid patterns is discussed.
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Hou, Jiaqi, Yuhan Zhou, Liping Ran, Yanzhu Chen, Ting Zhang, Bowei Sun, Yimo Yang, Qianzi Sang, and Li Cao. "Transcriptome and Metabolome Analysis Reveal the Flavonoid Biosynthesis Mechanism of Abelmoschus manihot L. at Different Anthesis Stages." Metabolites 13, no. 2 (February 1, 2023): 216. http://dx.doi.org/10.3390/metabo13020216.
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Abelmoschus manihot L. (HSK) is a rare and endangered species in the wild that grows on the cliffs of deep mountains. As a natural plant, the chemical composition of HSK is relatively complex, which mainly includes flavonoids, organic acids, polysaccharides, and various trace elements with good effects of clearing away heat, anti-inflammatory, analgesic, and calming nerves, and inhibiting tumor cells. In this experiment, different developmental stages of HSK flowers were used for optimization of the flavonoid extraction and determining method. The antioxidant activities, flavonoid accumulation pattern, and synthesis regulatory network were analyzed using biochemistry, RNA-seq, and UPLC-MS/MS. The total content of flavonoids, vitexin rhamnoside, hyperoside, and rutin in HSK flowers at T3 stage (flower wilting) was significantly higher than in T2 (full flowering) and T1 (bud) stages. Compared with T1 and T2, the antioxidant capacity of the T3 flower alcohol extract was also the strongest, including the total reducing ability, DPPH clearance, OH clearance, O2− clearance, and total antioxidant capacity. A total of 156 flavonoids and 47,179 unigenes were detected by UPLC-MS/MS and RNA-Seq, respectively. The candidate genes and key metabolites involved in flavonoid biosynthesis were identified and the regulatory networks were also analyzed in this study. qRT-PCR test further proved that the gene expression level was consistent with the results of RNA sequence data. The relationship between the gene expression and flavonoid accumulation network provides a theoretical basis for the mining and regulation of functional genes related to the flavonoid biosynthesis and metabolism in Abelmoschus manihot L.
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Yu, Yanhao, Yinquan Qu, Shuyang Wang, Qian Wang, Xulan Shang, and Xiangxiang Fu. "An Integrative Analysis of Metabolome and Transcriptome Reveals the Molecular Regulatory Mechanism of the Accumulation of Flavonoid Glycosides in Different Cyclocarya paliurus Ploidies." Forests 14, no. 4 (April 9, 2023): 770. http://dx.doi.org/10.3390/f14040770.
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Cyclocarya paliurus (Batal) Iljinskaja is mainly used for harvesting leaves as materials for tea production and ingredients for the food industry. As its most important component, the contents of its total or specific flavonoids are supposed to vary at different ploidy levels. In the present study, two ploidy levels of C. paliurus are used to study their metabolome and transcriptome profiles. Though the total content of the flavonoids in leaves that were collected in September (the main harvesting season) presented insignificant differences between the two ploidies, flavonoid glucuronides were significantly accumulated in the tetraploid C. paliurus. Several structural genes related to the biosynthesis of these flavonoid glucuronides were expressed differentially, including PAL, 4CL, CHS, and CpUGTs. A weighted gene co-expression network analysis (WGCNA) revealed that nine genes were highly correlated with the flavonoid glucuronide contents. Furthermore, 3 CpMYB39 and 3 CpUGT71 were highly associated with this accumulation of flavonoid glucuronides in tetraploid C. paliurus. These results can provide a new perspective on how different polyploid levels alter the quantitative and qualitative patterns of the secondary metabolite production in C. paliurus.
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Shang, Xiuhua, Guo Liu, Zhihua Wu, and Peijian Zhang. "Combined Transcriptomic and Metabolomic Analysis Reveals the Mechanism of Flavonoid Biosynthesis in Handroanthus chrysanthus (Jacq.) S.O.Grose." Forests 13, no. 8 (August 14, 2022): 1285. http://dx.doi.org/10.3390/f13081285.
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Handroanthus and Tabebuia are known for their ornamental and medicinal value, which are attributed to metabolites. However, the mechanisms underlying the synthesis of these metabolites are poorly understood. In this study, the expression levels of secondary metabolites and the mechanism of flavonoid biosynthesis in the bark and leaves of Handroanthus chrysantha (Jaq.) were examined using transcriptomic and metabolomic techniques. Metabolic analysis identified several differentially accumulated metabolites (DAMs), most of which were flavonoids, isoprenoids, and sterols. Additionally, 30 flavonoids were identified in the bark and leaves of H. chrysantha. Transcriptomic analysis identified 69 genes involved in flavonoid biosynthesis, among which 49 were significantly different between the bark and leaves. qRT-PCR analysis of eight genes involved in flavonoid biosynthesis showed that the expression patterns of the genes were consistent with the transcriptome sequencing data. Integrative transcriptomic and metabolomic analysis showed that 20 differentially expressed genes (DEGs) associated with flavonoid biosynthesis were strongly correlated with seven DAMs, confirming the involvement of the DEGs in flavonoid biosynthesis. These findings considerably contribute to the understanding of the biosynthesis of secondary metabolites in H. chrysantha and serve as a reference for further pharmacological studies.
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Uehara, Ayumi, Shinobu Akiyama, and Tsukasa Iwashina. "Foliar Flavonoids from Tanacetum vulgare var. boreale and their Geographical Variation." Natural Product Communications 10, no. 3 (March 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000307.
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Foliar flavonoids of Tanacetum vulgare var. boreale were isolated. Eight flavonoid glycosides, 7- O-glucosides of apigenin, luteolin, scutellarein and 6-hydroxyluteolin, and 7- O-glucuronides of apigenin, luteolin, chrysoeriol and eriodictyol were identified. Moreover, eight flavonoid aglycones, apigenin, luteolin, hispidulin, nepetin, eupatilin, jaceosidin, pectolinarigenin and axillarin were also isolated and identified. The flavonoid composition of two varieties of T. vulgare, i.e. var. boreale and var. vulgare, were compared. All samples of var. boreale and one sample of var. vulgare had the same flavonoid pattern, and could be distinguished from almost all the samples of var. vulgare. Thus, the occurrence of chemotypes, which are characterized by either the presence or absence of scutellarein 7- O-glucoside, eriodictyol 7- O-glucuronide and pectolinarigenin was shown in T. vulgare sensu lato.
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Bhandari, Shiva Ram, and Jun Gu Lee. "Ripening-Dependent Changes in Antioxidants, Color Attributes, and Antioxidant Activity of Seven Tomato (Solanum lycopersicumL.) Cultivars." Journal of Analytical Methods in Chemistry 2016 (2016): 1–13. http://dx.doi.org/10.1155/2016/5498618.
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To evaluate the ripening-dependent changes in phytonutrients, seven commercial cultivars (two general and five cherry) of tomatoes were cultivated under greenhouse conditions. Fruits were harvested at breaker, turning, pink, light red, and red stages of each cultivar, and antioxidant contents, color attributes, and antioxidant activities were measured. During ripening process, lycopene content increased from the breaker to red stage, while lutein displayed the reverse accumulation pattern, with higher values during the breaker stage. In contrast,β-carotene showed the highest levels of synthesis in pink and light red stages. Furthermore, flavonoids (quercetin, rutin, naringenin, and luteolin) also showed similar ripening-dependent changes, with higher quantities in pink and light red stages. Ascorbic acid showed continuously increasing patterns throughout ripening until the red stage, while the accumulation of total phenolics was cultivar-dependent. These results indicate that each antioxidant compound has a unique pattern of accumulation and degradation during the ripening process. “Unicon” exhibited highest total carotenoid (110.27 mg/100 g), total phenol (297.88 mg GAE/100 g) and total flavonoid content (273.33 mg/100 g), and consequently highest antioxidant activity (2552.4 μmol TE/100 g) compared to other cultivars. Throughout the ripening processes, total phenolics showed the highest correlation with antioxidant activity, followed byβ-carotene and total flavonoids. In conclusion, ripening in tomatoes is accompanied by incremental increases in various antioxidant compounds to some extent, as well as by concomitant increases in antioxidant activity.
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Bonvehí, Josep Serra, and Francesc Ventura Coll. "Phenolic Composition of Propolis from China and from South America." Zeitschrift für Naturforschung C 49, no. 11-12 (December 1, 1994): 712–18. http://dx.doi.org/10.1515/znc-1994-11-1204.
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Flavonoids and other phenolic compounds were determined in 15 samples of propolis originating from China, from Brazil, and from Uruguay. A total of 24 compounds were identified using mainly HPLC and a few other analytical methods. The most abundant compounds found were benzoic acid and benzaldehyde derivatives, flavones, flavonols. and flavanones. 80% of the samples contained at least 22 g/100 g of flavonoids, primarily acacetin, isorhamnetin, apigenin, and pinocembrin. The flavonoid patterns were sufficiently distinctive to permit discrimination between propolis from China, from Uruguay, and from Brazil.
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Ferreres, Federico, Francisco Tomás-Lorente, Francisco A. Tomás-Barberán, and Diego Rivera. "Biochemical Identification of Sideritis serrata X S. bourgaeana Hybrids by HPLC Analyses of Flavonoids." Zeitschrift für Naturforschung C 44, no. 7-8 (August 1, 1989): 568–72. http://dx.doi.org/10.1515/znc-1989-7-805.
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Abstract The existence of sympatric interspecific hybrids of Sideritis serrata Cav. ex Lag. and S. bou r gaeana Boiss. Reut, has been shown by HPLC analysis of the flavonoid glycosides accumulated in the cell sap, and by the methylated flavonoid aglycones exudated by the plants and deposited onto the plant surfaces. The hybrids tend to produce in a single plant the compounds characteristic of the parental taxa. This “complementation” effect in the hybrids permitted relatively easy detection of F1 hybrids. Generally, there was a close correlation between the biochemical results and a morphological analysis which used the Anderson’s index, although a specimen which morphologically was a hybrid, showed a flavonoid pattern as S. bourgaeana. The external flavonoids analysis has revealed that the activity of sideritoflavone O -methyltransferases is much more important in S. serrata than in S. bourgaeana, while the hybrids show intermediate values. M oreover, S. bourgaeana accumulates sideritoflavone 3′-m ethylether whereas S. serrata accum ulates the 4′-methylether. The hybrids produce both com pounds in similar amounts. In this study, external flavonoids have proved more useful than vacuolar flavonoid glycosides in the biochemical documentation of hybridization. This is probably due to the fact that methylated flavonoid aglycones are physiologically more stable as they are externally located and therefore preserved from the action of enzymes.
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Vieux, Florent, Matthieu Maillot, Colin D. Rehm, and Adam Drewnowski. "Flavonoid Intakes in the US Diet Are Linked to Higher Socioeconomic Status and to Tea Consumption: Analyses of NHANES 2011–16 Data." Journal of Nutrition 150, no. 8 (May 29, 2020): 2147–55. http://dx.doi.org/10.1093/jn/nxaa145.
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ABSTRACT Background Many of the health benefits of tea have been attributed to its flavonoid content. Tea consumption in US adults varies by socioeconomic status (SES). Objectives The present objective was to explore intakes of total flavonoids and flavonoid subclasses by participant sociodemographics and by patterns of tea consumption. Methods The present analyses were based on 2 d of dietary recalls for 17,506 persons aged >9 y in the 2011–2016 NHANES. The What We Eat in America nutrient composition database was merged with the USDA Expanded Flavonoid database, which included total flavonoids and flavan-3-ols (including catechins), flavanones, flavonols, anthocyanidins, flavones, and isoflavones. Flavonoid intakes were compared by sex, age, race/ethnicity, education, and income-to-poverty ratio (IPR) in univariate analyses. Flavonoid intakes of children and adults were also compared by tea consumption status. Time trends in flavonoid intakes were also examined. Results Mean total flavonoid intake was 219 mg/d, of which flavan-3-ols provided 174 mg/d, or 79%. The highest total flavonoid intakes were found in adults aged 51–70 y (293 mg/d), non-Hispanic whites (251 mg/d) and in groups with college education (251 mg/d) and higher income (IPR >3.5: 249 mg/d) (P < 0.001 for all). The socioeconomic gradient was significant for anthocyanidins, flavonols, and flavones (P < 0.001 for all) but not for flavan-3-ols, and persisted across 3 cycles of NHANES. Adult tea consumers had higher intakes of total flavonoids (610 mg/d compared with 141 mg/d) and flavan-3-ols (542 mg/d compared with 97.8 mg/d) than did nonconsumers (P < 0.001). Time trend analyses showed that both tea consumption and flavonoid intakes were unchanged from 2011 to 2016. Conclusions Flavonoid intakes in children and adults in the NHANES 2011–16 sample were associated with higher SES and were largely determined by tea consumption. Studies of diet and disease risk need to take sociodemographic gradients and eating and drinking habits into account.
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Wang, Tao, Fengjiao Zhang, Weibing Zhuang, Xiaochun Shu, and Zhong Wang. "Metabolic Variations of Flavonoids in Leaves of T. media and T. mairei Obtained by UPLC-ESI-MS/MS." Molecules 24, no. 18 (September 12, 2019): 3323. http://dx.doi.org/10.3390/molecules24183323.
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The needles of Taxus species contain a large number of bioactive compounds, such as flavonoids. In the present study, the total flavonoid content in leaves of Taxus media and Taxus mairei was 19.953 and 14.464 mg/g, respectively. A total of 197 flavonoid metabolites (70 flavones, 42 flavonols, 26 flavone C-glycosides, 20 flavanones, 15 anthocyanins, 13 isoflavones, 6 flavonolignans, and 5 proanthocyanidins) were identified for the first time by a widely targeted Ultra Performance Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry (UPLC-ESI-MS/MS) method within the two Taxus species, containing 160 common metabolites, with 37 unique metabolites merely determined in T. mairei or T. media. Moreover, 42 differential flavonoid metabolites were screened in the two Taxus species, which showed specific metabolic patterns in isoflavonoid biosynthesis, anthocyanin biosynthesis, and flavone and flavonol biosynthesis pathways. Compared to T. mairei, a more activated phenylpropanoid pathway was found in T. media, which could be responsible for the higher content of total flavonoids in T. media. Our results provide new insights into the diversity of flavonoid metabolites between T. mairei and T. media, and provide a theoretical basis for the sufficient utilization of Taxus species and the development of novel drugs.
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Ichino, Takuji, Kazuki Maeda, Ikuko Hara-Nishimura, and Tomoo Shimada. "Arabidopsis ECHIDNA protein is involved in seed coloration, protein trafficking to vacuoles, and vacuolar biogenesis." Journal of Experimental Botany 71, no. 14 (March 23, 2020): 3999–4009. http://dx.doi.org/10.1093/jxb/eraa147.
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Abstract Flavonoids are a major group of plant-specific metabolites that determine flower and seed coloration. In plant cells, flavonoids are synthesized at the cytosolic surface of the endoplasmic reticulum and are sequestered in the vacuole. It is possible that membrane trafficking, including vesicle trafficking and organelle dynamics, contributes to flavonoid transport and accumulation. However, the underlying mechanism has yet to be fully elucidated. Here we show that the Arabidopsis ECHIDNA protein plays a role in flavonoid accumulation in the vacuole and protein trafficking to the vacuole. We found defective pigmentation patterns in echidna seed, possibly caused by reduced levels of proanthocyanidins, which determine seed coloration. The echidna mutant has defects in protein sorting to the protein storage vacuole as well as vacuole morphology. These findings indicate that ECHIDNA is involved in the vacuolar trafficking pathway as well as the previously described secretory pathway. In addition, we found a genetic interaction between echidna and green fluorescent seed 9 (gfs9), a membrane trafficking factor involved in flavonoid accumulation. Our findings suggest that vacuolar trafficking and/or vacuolar development, both of which are collectively regulated by ECHIDNA and GFS9, are required for flavonoid accumulation, resulting in seed coat pigmentation.
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Dong, Yongzhe, Jingya Ruan, Zhijuan Ding, Wei Zhao, Mimi Hao, Ying Zhang, Hongyu Jiang, Yi Zhang, and Tao Wang. "Phytochemistry and Comprehensive Chemical Profiling Study of Flavonoids and Phenolic Acids in the Aerial Parts of Allium Mongolicum Regel and Their Intestinal Motility Evaluation." Molecules 25, no. 3 (January 29, 2020): 577. http://dx.doi.org/10.3390/molecules25030577.
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To clarify whether flavonoids and phenols in Allium mongolicum Regel have the effect of improving gastrointestinal function and analyze its quality, this study was designed to isolate and identify them from the aerial parts of A. mongolicum by using various chromatographic and spectrophotometric methods, a bioassay on motility of mouse isolated intestine tissue, as well as qualitative analysis using liquid chromatography/mass spectrometry (LC-MS) analysis. As a result, 31 flavonoids and phenolic acids were obtained and identified, including six new flavonoid glycosides, mongoflavonosides A1 (1), A2 (2), A3 (3), A4 (4), B1 (5), B2 (6), and four new phenolic acid glycosides, mongophenosides A1 (7), A2 (8), A3 (9), B (10). Among them, eleven flavonoids and three phenolic acids showed significant increase in the height of mouse small intestinal muscle. It was a first systematic bioactive constituents’ study for A. mongolicum on gastrointestinal tract. Furthermore, according to the retention time (tR) and the exact mass-to-charge ratio (m/z), thirty-one compounds were unambiguously identified by comparing to the standard references by using LC-MS. Then, on the basis of generalized rules of MS/MS fragmentation pattern, chromatographic behaviors, as well as biosynthetic laws of the 31 isolates, five flavonoid glycosides and one phenolic acid glycoside were tentatively speculated. On the basis of the study, a fast analysis method for flavonoids and phenolic acids in A. mongolicum was established.
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Ferraz, Camila R., Thacyana T. Carvalho, Marília F. Manchope, Nayara A. Artero, Fernanda S. Rasquel-Oliveira, Victor Fattori, Rubia Casagrande, and Waldiceu A. Verri. "Therapeutic Potential of Flavonoids in Pain and Inflammation: Mechanisms of Action, Pre-Clinical and Clinical Data, and Pharmaceutical Development." Molecules 25, no. 3 (February 10, 2020): 762. http://dx.doi.org/10.3390/molecules25030762.
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Pathological pain can be initiated after inflammation and/or peripheral nerve injury. It is a consequence of the pathological functioning of the nervous system rather than only a symptom. In fact, pain is a significant social, health, and economic burden worldwide. Flavonoids are plant derivative compounds easily found in several fruits and vegetables and consumed in the daily food intake. Flavonoids vary in terms of classes, and while structurally unique, they share a basic structure formed by three rings, known as the flavan nucleus. Structural differences can be found in the pattern of substitution in one of these rings. The hydroxyl group (–OH) position in one of the rings determines the mechanisms of action of the flavonoids and reveals a complex multifunctional activity. Flavonoids have been widely used for their antioxidant, analgesic, and anti-inflammatory effects along with safe preclinical and clinical profiles. In this review, we discuss the preclinical and clinical evidence on the analgesic and anti-inflammatory proprieties of flavonoids. We also focus on how the development of formulations containing flavonoids, along with the understanding of their structure-activity relationship, can be harnessed to identify novel flavonoid-based therapies to treat pathological pain and inflammation.
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Corley, Janie, Janet A. M. Kyle, John M. Starr, Geraldine McNeill, and Ian J. Deary. "Dietary factors and biomarkers of systemic inflammation in older people: the Lothian Birth Cohort 1936." British Journal of Nutrition 114, no. 7 (September 7, 2015): 1088–98. http://dx.doi.org/10.1017/s000711451500210x.
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Epidemiological studies have reported inverse associations between various single healthy diet indices and lower levels of systemic inflammation, but rarely are they examined in the same sample. The aim of the present study was to investigate the potential relationships between biomarkers of systemic inflammation (C-reactive protein (CRP) and fibrinogen) and overall foods (dietary patterns), single foods (fruits and vegetables), and specific nutritive (antioxidants) and non-nutritive (flavonoids) food components in the same narrow-age cohort of older adults. The dietary intake of 792 participants aged 70 years from the Lothian Birth Cohort 1936 was assessed using a 168-item FFQ. Models were adjusted for age, sex, childhood cognitive ability, lifestyle factors and history of disease. Using logistic regression analyses, CRP (normal v. elevated) was favourably associated (at P< 0·05) with the ‘health-aware’ (low-fat) dietary pattern (unstandardised β = (0·200, OR 0·82, 95 % CI 0·68, 0·99) and fruit intake (unstandardised β = (0·100, OR 0·91, 95 % CI 0·82, 0·99), including flavonoid-rich apples (unstandardised β = (0·456, OR 0·63, 95 % CI 0·439, 0·946). Using linear regression analyses, fibrinogen (continuous) was inversely associated (at P< 0·05) with the Mediterranean dietary pattern (standardised β = (0·100), fruit intake (standardised β = (0·083), and combined fruit and vegetable intake (standardised β = (0·084). We observed no association between food components (antioxidant nutrients or specific flavonoid subclasses) and inflammatory markers. In the present cross-sectional study, nutrient-dense dietary patterns were associated with lower levels of systemic inflammation in older people. The results are consistent with dietary guidelines that promote a balanced diet based on a variety of plant-based foods.
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Brinkmeier, Elke, Hans Geiger, and Hans Dietmar Zinsmeister. "The Cooccurrence of Different Biflavonoid Types in Pilotrichella flexilis§." Zeitschrift für Naturforschung C 55, no. 11-12 (December 1, 2000): 866–69. http://dx.doi.org/10.1515/znc-2000-11-1202.
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From Pilotrichella flexilis various flavonoids have been isolated. This species contains in contrast to P. cuspidata not only 3′,3‴-binaringenin and related compounds, but also some hitherto unknown biflavonoids based on eriodictyol and aureusidin. The structures of two new compounds are elucidated spectroscopically. Possible causes for the differences of the flavonoid patterns between the two species of the genus Pilotrichella are discussed.
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Zamora-Ros, Raul, Viktoria Knaze, Leila Luján-Barroso, Isabelle Romieu, Augustin Scalbert, Nadia Slimani, Anette Hjartåker, et al. "Differences in dietary intakes, food sources and determinants of total flavonoids between Mediterranean and non-Mediterranean countries participating in the European Prospective Investigation into Cancer and Nutrition (EPIC) study." British Journal of Nutrition 109, no. 8 (September 14, 2012): 1498–507. http://dx.doi.org/10.1017/s0007114512003273.
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A greater adherence to the traditional Mediterranean (MED) diet is associated with a reduced risk of developing chronic diseases. This dietary pattern is based on higher consumption of plant products that are rich in flavonoids. We compared the total flavonoid dietary intakes, their food sources and various lifestyle factors between MED and non-MED countries participating in the EPIC study. Flavonoid intakes and their food sources for 35 628 subjects, aged 35–74 years and recruited between 1992 and 2000, in twenty-six study centres were estimated using standardised 24 h dietary recall software (EPIC-Soft®). An ad hoc food composition database on flavonoids was compiled using analytical data from the United States Department of Agriculture and Phenol-Explorer databases. Moreover, it was expanded to include using recipes, estimations of missing values and flavonoid retention factors. No significant differences in total flavonoid mean intake between non-MED countries (373·7 mg/d) and MED countries (370·2 mg/d) were observed. In the non-MED region, the main contributors were proanthocyanidins (48·2 %) and flavan-3-ol monomers (24·9 %) and the principal food sources were tea (25·7 %) and fruits (32·8 %). In the MED region, proanthocyanidins (59·0 %) were by far the most abundant contributor and fruits (55·1 %), wines (16·7 %) and tea (6·8 %) were the main food sources. The present study shows similar results for total dietary flavonoid intakes, but significant differences in flavonoid class intakes, food sources and some characteristics between MED and non-MED countries. These differences should be considered in studies about the relationships between flavonoid intake and chronic diseases.
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Guo, Peng, Ziqi Huang, Xinke Li, Wei Zhao, and Yihan Wang. "Transcriptome Sequencing of Broussonetia papyrifera Leaves Reveals Key Genes Involved in Flavonoids Biosynthesis." Plants 12, no. 3 (January 26, 2023): 563. http://dx.doi.org/10.3390/plants12030563.
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Broussonetia papyrifera is rich in flavonoids, which have significant antioxidant, antibacterial, and anti-inflammatory activities and certain pharmacological activities. Nevertheless, scarce transcriptome resources of B. papyrifera have impeded further study regarding the process of its production and accumulation. In this study, RNA-seq was utilized to evaluate the gene expression of B. papyrifera leaves at three distinct developmental phases (T1: young leaves, T3: immature leaves, T4: matured leaves). We obtained 2447 upregulated and 2960 downregulated DEGs, 4657 upregulated and 4804 downregulated DEGs, and 805 upregulated and 484 downregulated DEGs from T1 vs. T3, T1 vs. T4, and T3 vs. T4, respectively. Further research found that the following variables contributed to the formation of flavonoids in the leaves of B. papyrifera: Several important enzyme genes involved in flavonoid production pathways have been discovered. The results demonstrated that the dynamic changing trend of flavonoid contents is related to the expression pattern of the vast majority of essential genes in the biosynthetic pathway. Genes associated in energy and glucose metabolism, polysaccharide, cell wall and cytoskeleton metabolism, signal transduction, and protein and amino acid metabolism may affect the growth and development of B. papyrifera leaves, and eventually their flavonoid content. This study’s results offer a strong platform for future research into the metabolic pathways of B. papyrifera.
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Zhu, Wencan, Hongxia Wu, Chengkun Yang, Xiaowen Wang, Bin Shi, Bin Zheng, Xiaowei Ma, Minjie Qian, Aiping Gao, and Kaibing Zhou. "Transcription Regulation of Anthocyanins and Proanthocyanidins Accumulation by Bagging in ‘Ruby’ Red Mango: An RNA-seq Study." Horticulturae 9, no. 8 (July 31, 2023): 870. http://dx.doi.org/10.3390/horticulturae9080870.
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The biosynthesis of anthocyanins and proanthocyanidins (PAs), components of two main flavonoids in plants, is regulated by environmental factors such as light. We previously found that bagging significantly repressed the biosynthesis of anthocyanins in red ‘Ruby’ mango fruit peel, but induced the accumulation of PAs. However, the molecular mechanism remains unclear. In the current study, transcriptome sequencing was used for screening the essential genes responsible for the opposite accumulation pattern of anthocyanins and PAs by bagging treatment. According to weighted gene co-expression network analysis (WGCNA), structural genes and transcription factors highly positively correlated to anthocyanins and PAs were identified. One flavanone 3-hydroxylase (F3H) and seven structural genes, including one chalcone synthase (CHS), one flavonoid 3’-hydroxylase (F3’H), one anthocyanidin synthesis (ANS), three leucoanthocyanidin reductase (LARs), and one UDP glucose: flavonoid 3-O-glucosyltransferase (UFGT), are crucial for anthocyanin and PA biosynthesis, respectively. In addition to MYB and bHLH, ERF, C2H2, HD-ZIP, and NAC are important transcription factors that participate in the regulation of anthocyanin and PA biosynthesis in ‘Ruby’ mango fruit peel by bagging treatment. Our results are helpful for revealing the transcription regulation mechanism of light-regulated mango anthocyanin and PA biosynthesis, developing new technologies for inducing flavonoid biosynthesis in mangos, and breeding mango cultivars containing high concentrations of flavonoids.
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Liu, Jianyu, Naveed Ahmad, Yingqi Hong, Meihua Zhu, Shah Zaman, Nan Wang, Na Yao, and Xiuming Liu. "Molecular Characterization of an Isoflavone 2′-Hydroxylase Gene Revealed Positive Insights into Flavonoid Accumulation and Abiotic Stress Tolerance in Safflower." Molecules 27, no. 22 (November 18, 2022): 8001. http://dx.doi.org/10.3390/molecules27228001.
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Flavonoids with significant therapeutic properties play an essential role in plant growth, development, and adaptation to various environments. The biosynthetic pathway of flavonoids has long been studied in plants; however, its regulatory mechanism in safflower largely remains unclear. Here, we carried out comprehensive genome-wide identification and functional characterization of a putative cytochrome P45081E8 gene encoding an isoflavone 2′-hydroxylase from safflower. A total of 15 CtCYP81E genes were identified from the safflower genome. Phylogenetic classification and conserved topology of CtCYP81E gene structures, protein motifs, and cis-elements elucidated crucial insights into plant growth, development, and stress responses. The diverse expression pattern of CtCYP81E genes in four different flowering stages suggested important clues into the regulation of secondary metabolites. Similarly, the variable expression of CtCYP81E8 during multiple flowering stages further highlighted a strong relationship with metabolite accumulation. Furthermore, the orchestrated link between transcriptional regulation of CtCYP81E8 and flavonoid accumulation was further validated in the yellow- and red-type safflower. The spatiotemporal expression of CtCYP81E8 under methyl jasmonate, polyethylene glycol, light, and dark conditions further highlighted its likely significance in abiotic stress adaption. Moreover, the over-expressed transgenic Arabidopsis lines showed enhanced transcript abundance in OE-13 line with approximately eight-fold increased expression. The upregulation of AtCHS, AtF3′H, and AtDFR genes and the detection of several types of flavonoids in the OE-13 transgenic line also provides crucial insights into the potential role of CtCYP81E8 during flavonoid accumulation. Together, our findings shed light on the fundamental role of CtCYP81E8 encoding a putative isoflavone 2′-hydroxylase via constitutive expression during flavonoid biosynthesis.
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Djordjevic, M. A., U. Mathesius, T. Arioli, J. J. Weinman, and E. Gärtner. "Chalcone Synthase Gene Expression in Transgenic Subterranean Clover Correlates with Localised Accumulation of Flavonoids." Functional Plant Biology 24, no. 2 (1997): 119. http://dx.doi.org/10.1071/pp96095.
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Expression patterns of two clover chalcone synthase promoters (TsCHS1 and TsCHS3) were examined in transgenic Trifolium subterraneum plants to investigate flavonoid gene regulation and to determine if there is differential regulation of these promoters from the CHS multigene family. The CHS1 and CHS3 genes occur as part of a tightly linked cluster of tandemly orientated genes in subterranean clover. The CHS promoters were fused to the β-glucuronidase (GUS) reporter gene and reintroduced into subterranean clovers. Analysis of the expression of the reporter genes showed that near-identical expression patterns occurred in the transgenic plants containing either the CHS1:GUS or the CHS3:GUS fusions. Both promoters responded rapidly to wounding of the shoot. Distinct changes in the expression patterns of both promoters occurred during the development of leaves and flowers. In young shoots, expression occurred throughout the tissues and was restricted to the cambium and xylem parenchyma in mature tissue. Roots possessed the highest activity levels, which were primarily located in the meristematic tissues of the tap root, lateral root and nodule. Epifluorescent localisation of flavonoids using diphenylboric acid-2-aminoethylester correlated with the site of GUS activity in most tissues. These results indicate that histochemical detection of CHS expression in various root meristems and flower parts is correlated with localised flavonoid accumulation in these cells. Our studies suggest a physiological role for flavonoids at those sites.
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Ranabahu, Priyanganie, and Jeffrey B. Harborne. "The flavonoids of the genus Lathyrus and a comparison of flavonoid patterns within the tribe vicieae." Biochemical Systematics and Ecology 21, no. 6-7 (September 1993): 715–22. http://dx.doi.org/10.1016/0305-1978(93)90077-5.
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Prado, Yolanda, Cesar Echeverría, Carmen G. Feijóo, Claudia A. Riedel, Claudio Cabello-Verrugio, Juan F. Santibanez, and Felipe Simon. "Effect of Dietary Supplements with ω-3 Fatty Acids, Ascorbic Acid, and Polyphenolic Antioxidant Flavonoid on Gene Expression, Organ Failure, and Mortality in Endotoxemia-Induced Septic Rats." Antioxidants 12, no. 3 (March 7, 2023): 659. http://dx.doi.org/10.3390/antiox12030659.
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Sepsis syndrome develops through enhanced secretion of pro-inflammatory cytokines and the generation of reactive oxygen species (ROS). Sepsis syndrome is characterized by vascular hyperpermeability, hypotension, multiple organ dysfunction syndrome (MODS), and increased mortality, among others. Endotoxemia-derived sepsis is an important cause of sepsis syndrome. During endotoxemia, circulating endotoxin interacts with endothelial cells (ECs), inducing detrimental effects on endothelium function. The endotoxin induces the conversion of ECs into fibroblasts, which are characterized by a massive change in the endothelial gene-expression pattern. This downregulates the endothelial markers and upregulates fibrotic proteins, mesenchymal transcription factors, and extracellular matrix proteins, producing endothelial fibrosis. Sepsis progression is modulated by the consumption of specific nutrients, including ω-3 fatty acids, ascorbic acid, and polyphenolic antioxidant flavonoids. However, the underlying mechanism is poorly described. The notion that gene expression is modulated during inflammatory conditions by nutrient consumption has been reported. However, it is not known whether nutrient consumption modulates the fibrotic endothelial gene-expression pattern during sepsis as a mechanism to decrease vascular hyperpermeability, hypotension, MODS, and mortality. Therefore, the aim of this study was to investigate the impact of the consumption of dietary ω-3 fatty acids, ascorbic acid, and polyphenolic antioxidant flavonoid supplements on the modulation of fibrotic endothelial gene-expression patterns during sepsis and to determine the effects on sepsis outcomes. Our results indicate that the consumption of supplements based on ω-3 fatty acids and polyphenolic antioxidant flavonoids was effective for improving endotoxemia outcomes through prophylactic ingestion and therapeutic usage. Thus, our findings indicated that specific nutrient consumption improves sepsis outcomes and should be considered in treatment.
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Rui, Wen, Hongyuan Chen, Yuzhi Tan, Yanmei Zhong, and Yifan Feng. "Rapid Analysis of the Main Components of the Total Glycosides of Ranunculus japonicus by UPLC/Q-TOF-MS." Natural Product Communications 5, no. 5 (May 2010): 1934578X1000500. http://dx.doi.org/10.1177/1934578x1000500521.
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A rapid method for the analysis of the main components of the total glycosides of Ranunculus japonicus (TGOR) was developed using ultra-performance liquid chromatography with quadrupole-time-of-flight mass spectrometry (UPLC/Q-TOF-MS). The separation analysis was performed on a Waters Acquity UPLC system and the accurate mass of molecules and their fragment ions were determined by Q-TOF MS. Twenty compounds, including lactone glycosides, flavonoid glycosides and flavonoid aglycones, were identified and tentatively deduced on the basis of their elemental compositions, MS/MS data and relevant literature. The results demonstrated that lactone glycosides and flavonoids were the main constituents of TGOR. Furthermore, an effective and rapid pattern was established allowing for the comprehensive and systematic characterization of the complex samples.
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Ticona, Juan C., Pablo Bilbao-Ramos, Ángel Amesty, Ninoska Flores, M. Auxiliadora Dea-Ayuela, Isabel L. Bazzocchi, and Ignacio A. Jiménez. "Flavonoids from Piper Species as Promising Antiprotozoal Agents against Giardia intestinalis. Structure-Activity Relationship and Drug-Likeness Studies." Pharmaceuticals 15, no. 11 (November 10, 2022): 1386. http://dx.doi.org/10.3390/ph15111386.
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Diarrhea diseases caused by the intestinal protozoan parasite Giardia intestinalis are a major global health burden. Moreover, there is an ongoing need for novel anti-Giardia drugs due to drawbacks with currently available treatments. This paper reports on the isolation and structural elucidation of six new flavonoids (1–6), along with twenty-three known ones (7–29) from the Piper species. Their structures were established by spectroscopic and spectrometric techniques. Flavonoids were tested for in vitro antiprotozoal activity against Giardia intestinalis trophozoites. In addition, structure-activity relationship (SAR) and in silico ADME studies were performed to understand the pharmacophore and pharmacokinetic properties of these natural compounds. Eight flavonoids from this series exhibited remarkable activity in the micromolar range. Moreover, compound 4 was identified as having a 40-fold greater antiparasitic effect (IC50 61.0 nM) than the clinical reference drug, metronidazole (IC50 2.5 µM). This antiprotozoal potency was coupled with an excellent selectivity index (SI 233) on murine macrophages and in silico drug-likeness. SAR studies revealed that the substitution patterns, type of functional group, and flavonoid skeleton played an essential role in the activity. These findings highlight flavonoid 4 as a promising candidate to develop new drugs for the treatment of Giardia infections.
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Bergonci, Tábata, Inge S. Fomsgaard, Katrine H. Kjaer, and Ivan A. Paponov. "Hormone–Flavonoid Patterns in Two Genotypes of Campanula portenschlagiana with Distinct Adventitious Rooting Competence." Horticulturae 9, no. 1 (January 16, 2023): 121. http://dx.doi.org/10.3390/horticulturae9010121.
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In horticulture and floriculture, plants are predominantly propagated vegetatively from stem cuttings. Consequently, the success of propagation depends on a plant’s capacity to form adventitious roots (AR) at the basal part of the cutting, and AR formation depends on the interaction between flavonoids and plant hormones in the basal part. In ornamental plants, flavonoid accumulation is important for flower color and can interact with plant hormone activity. In this study, we used an aeroponic system to culture two Campanula portenschlagiana genotypes contrasting in flower color to estimate cultivar differences in AR formation, flavonoid concentrations, and hormone composition. We found a greater accumulation of flavonols and flavones in petals in a blue-flowered genotype than in a white-flowered genotype. The blue-flowered genotype also accumulated more flavonols and flavones in the basal part of cuttings and showed better AR formation. The better AR formation in the blue-colored genotype was related to a greater accumulation of auxin and a lower accumulation of ABA in the basal part of the cuttings. In conclusion, higher flavonoid levels in the basal part of cuttings may interact with hormone action to affect excision-induced AR formation during the vegetative propagation of Campanula.
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Bonvehí, Josep Serra, and Francesc Ventura Coll. "Study on Propolis Quality from China and Uruguay." Zeitschrift für Naturforschung C 55, no. 9-10 (October 1, 2000): 778–84. http://dx.doi.org/10.1515/znc-2000-9-1017.
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Abstract The composition, bacteriostatic and ROO• -scavenging potential activities of fifteen propolis samples from various botanic and geographic origins were determined to obtain objective information related to propolis quality. Variance analysis showed significant differences (p ≤ 0.05) in the contents of polyphenols, flavonoids and active components between fresh and aged propolis. The state of the product (fresh or aged) could be differentiate by using flavonoid pattern and biological activities. A minimum propolis concentration of 80 μg/ml was required inhibit Bacillus subtilis and Staphylococcus aureus while 800 μg/ml was required to inhibit Escherichia coli using fresh propolis. Aged propolis inhibit B. subtilis and S. aureus at concentration of 100 μg/ml and E. coli at 1000 μg/ml. A minimum flavonoids percentage of 18 g/100 g and a maximum ROO• -scavenging potential activity of 4.3 μg/ml were determined in fresh propolis. Flavonoids levels in aged propolis were approximately 20% lower than in fresh propolis. A maximum flavonoids percentage of 19.8 g/100 g and a ROO•-scavenging potential activity between 5.7 to 6.4 μg/ml in aged propolis were quantified. Another objective was to assess the use of ROO•-scavenging potential activity in propolis quality.
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Lupea, Alfa Xenia, Mariana Pop, and Svetlana Cacig. "Structure-Radical Scavenging Activity Relationships of Flavonoids from Ziziphus and Hydrangea Extracts." Revista de Chimie 59, no. 3 (April 9, 2008): 309–13. http://dx.doi.org/10.37358/rc.08.3.1754.
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Methanol extracts prepared from Ziziphus and Hydrangea fruits and leaves were examined for their antioxidant activity. Antioxidative activities were studied in sunflower oil at 980C, by measuring peroxide value, and with the spectrophotometric method, which uses 1, 1 diphenyl-2-picrylhydrazyl (DPPH) free radicals. The relationship between the structural characteristics of pure four flavonoids and their antioxidant activity was also studied. The obtained results suggest that the free radical scavenger potential of these polyphenolic compounds closely depends on the particular substitution pattern of free hydroxyl groups on the flavonoid skeleton.
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Chen, Jing, Yaliang Shi, Yicheng Zhong, Zhimin Sun, Juan Niu, Yue Wang, Tianxin Chen, Jianhua Chen, and Mingbao Luan. "Transcriptome Analysis and HPLC Profiling of Flavonoid Biosynthesis in Citrus aurantium L. during Its Key Developmental Stages." Biology 11, no. 7 (July 19, 2022): 1078. http://dx.doi.org/10.3390/biology11071078.
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Citrus aurantium L. (sour orange) is a significant Chinese medicinal and fruit crop rich in flavonoids. However, the pathways and genes involved in flavonoid biosynthesis at the key developmental stages of Citrus aurantium L. are not fully understood. This study found that the total flavonoid concentration gradually decreased as the fruit developed. Additionally, it showed that neohesperidin was the main flavonoid in the early stages of sour orange fruit development. However, as the development stage progressed, naringin content increased rapidly and emerged as the main flavonoid component. From 27 cDNA libraries, RNA sequencing yielded 16.64 billion clean bases, including 8989 differentially expressed genes. We identified 74 flavonoid related unigenes mapped to the phenylalanine, tyrosine, and phenylpropanoid biosynthesis pathways. A total of 152 UDP-glucuronosyltransferase genes (UGTs) were identified from C. aurantium L. transcriptome database, in which 22 key flavonoid-correlated UGTs were divided into five main AtGT groups: E, G, I, L, M. We observed that the ethylene responsive factors (ERF) and myeloblastosis (MYB) family mainly regulated the key genes involved in flavonoid biosynthesis. Overall, our study generated extensive and detailed transcriptome data on the development of C. aurantium L. and characterized the flavonoid biosynthesis pattern during its fruit developmental stages. These results will benefit genetic modification or selection to increase the flavonoid content in sour oranges.
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Pallauf, Kathrin, Nils Duckstein, Mario Hasler, Lars-Oliver Klotz, and Gerald Rimbach. "Flavonoids as Putative Inducers of the Transcription Factors Nrf2, FoxO, and PPARγ." Oxidative Medicine and Cellular Longevity 2017 (2017): 1–11. http://dx.doi.org/10.1155/2017/4397340.
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Dietary flavonoids have been shown to extend the lifespan of some model organisms and may delay the onset of chronic ageing-related diseases. Mechanistically, the effects could be explained by the compounds scavenging free radicals or modulating signalling pathways. Transcription factors Nrf2, FoxO, and PPARγpossibly affect ageing by regulating stress response, adipogenesis, and insulin sensitivity. Using Hek-293 cells transfected with luciferase reporter constructs, we tested the potency of flavonoids from different subclasses (flavonols, flavones, flavanols, and isoflavones) to activate these transcription factors. Under cell-free conditions (ABTS and FRAP assays), we tested their free radical scavenging activities and usedα-tocopherol and ascorbic acid as positive controls. Most of the tested flavonoids, but not the antioxidant vitamins, stimulated Nrf2-, FoxO-, and PPARγ-dependent promoter activities. Flavonoids activating Nrf2 also tended to induce a FoxO and PPARγresponse. Interestingly, activation patterns of cellular stress response by flavonoids were not mirrored by their activities in ABTS and FRAP assays, which depended mostly on hydroxylation in the flavonoid B ring and, in some cases, extended that of the vitamins. In conclusion, the free radical scavenging properties of flavonoids do not predict whether these molecules can stimulate a cellular response linked to activation of longevity-associated transcription factors.
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Auguy, Florence, Khalid Abdel-Lateif, Patrick Doumas, Pablo Badin, Vanessa Guerin, Didier Bogusz, and Valérie Hocher. "Activation of the isoflavonoid pathway in actinorhizal symbioses." Functional Plant Biology 38, no. 9 (2011): 690. http://dx.doi.org/10.1071/fp11014.
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We investigated the involvement of flavonoids in the actinorhizal nodulation process resulting from the interaction between the tropical tree Casuarina glauca Sieb. ex Spreng. and the actinomycete Frankia. Eight C. glauca genes involved in flavonoid biosynthesis: chalcone synthase (CHS), chalcone isomerase (CHI), isoflavone reductase (IFR), flavonoid-3-hydroxylase (F3H), flavonoid 3′-hydroxylase (F3′H), flavonoid 3′,5′ hydroxylase (F3′5′H), dihydroflavonol 4-reductase (DFR) and flavonol synthase (FLS), were identified from a unigene database and gene expression patterns were monitored by quantitative real-time PCR (qRT–PCR) during the nodulation time course. Results showed that FLS and F3′5′H transcripts accumulated in mature nodules whereas CHI and IFR transcripts accumulated preferentially early after inoculation with Frankia. Comparison of IFR and CHI expression in inoculated plants and in control plants cultivated with or without nitrogen confirmed that early expression of IFR is specifically linked to symbiosis. Taken together, these data suggest for the first time that isoflavonoids are implicated in actinorhizal nodulation.
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CHENG, Shuiyuan, Feng XU, Linling LI, Hua CHENG, and Weiwei ZHANG. "Seasonal Pattern of Flavonoid Content and Related Enzyme Activities in Leaves of Ginkgo biloba L." Notulae Botanicae Horti Agrobotanici Cluj-Napoca 40, no. 1 (May 14, 2012): 98. http://dx.doi.org/10.15835/nbha4017262.
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The contents of flavonoids and other related components, in addition to the activities of related enzymes, such as phenylalanine ammonia-lyase (PAL), peroxidase (POD), chalcone synthase (CHS), and UDP-glucose:flavonoid 3-O-glucosyltransferase (UFGT), were determined in Ginkgo biloba L. leaves during leaf development. The results indicated that POD activity increased gradually in the early stages and reached its first activity peak in the beginning of Jul., the second one in late Aug., and the third one (the highest peak) in the middle of Oct. The changes in POD activity were irregular, and its activity was maintained at a low level in the early stages. However, it increased rapidly from the middle of Sep., and reached its highest value in the middle of Oct. Three peaks were obtained for PAL activity. The first peak, with the highest value was in early to middle Jul. The second one, with the lowest value, was in late Aug., and the last one, with a higher value and the longest period, was after the middle of Sep. UFGT activity had a speedy increase in the early stages and continued to increase after May. However, the net increase remained low. CHS activity was enhanced during all stages and showed two obvious peaks. The first time was in early Jul., and the other, with a higher value, was in the middle of Nov. Although PAL activity had a close relationship with the flavonoid content, no notable correlation could be identified between them. A significant correlation between CHS activity and the flavonoid content showed that CHS was one of the key enzymes involved in flavonoid biosynthesis. The relationship between flavonoid content and other related enzymes is discussed in this study.
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Reninta, R., W. Nawfetrias, A. Tanjung, R. N. Utami, D. P. Handayani, and D. Pinardi. "Effect of extraction method on the flavonoid content of potential medicinal plant Phyllanthus niruri L." IOP Conference Series: Earth and Environmental Science 1114, no. 1 (December 1, 2022): 012073. http://dx.doi.org/10.1088/1755-1315/1114/1/012073.
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Abstract The extraction process in herbal plants maintains the quality of herb extracts by reducing the water content to prevent the growth of microorganisms and minimize the alteration of metabolites in plants. In this study, we investigate the effect of drying methods and incubation temperature on the flavonoid content of Phyllanthus niruri. Herb samples were fresh, oven-dried, and air-dried. Air-dried sample produced the highest total flavonoid level compared to other drying methods incubating at -20 degrees Celcius and 27-30 degrees Celcius. Air-dried samples incubated at room temperature had the highest total flavonoid content compared to other methods, followed by oven-dried and fresh samples. Fresh samples produced the highest yield compared to other drying methods on incubation at room temperature and -20 degrees Celcius. Various drying methods show a similar result of total flavonoids on incubation at -20 degrees Celsius, despite air-dried samples having the highest flavonoid content. Incubation temperatures have no significant difference in yield and flavonoid content, but the drying method shows otherwise. There is no interaction between the drying method and incubation temperature. Air-dried and oven-dried samples incubated at room temperature produce higher yield and flavonoid content than those incubated at -20 degrees Celcius, having a similar pattern.