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Search Results (1,451)

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19 pages, 9721 KiB  
Article
Unveiling the Molecular Mechanisms of Browning in Camellia hainanica Callus through Transcriptomic and Metabolomic Analysis
by Kunlin Wu, Yanju Liu, Yufen Xu, Zhaoyan Yu, Qiulin Cao, Han Gong, Yaodong Yang, Jianqiu Ye and Xiaocheng Jia
Int. J. Mol. Sci. 2024, 25(20), 11021; https://doi.org/10.3390/ijms252011021 - 14 Oct 2024
Viewed by 252
Abstract
Camellia hainanica is one of the camellia plants distributed in tropical regions, and its regeneration system and genetic transformation are affected by callus browning. However, the underlying mechanism of Camellia hainanica callus browning formation remains largely unknown. To investigate the metabolic basis and [...] Read more.
Camellia hainanica is one of the camellia plants distributed in tropical regions, and its regeneration system and genetic transformation are affected by callus browning. However, the underlying mechanism of Camellia hainanica callus browning formation remains largely unknown. To investigate the metabolic basis and molecular mechanism of the callus browning of Camellia hainanica, histological staining, high-throughput metabolomics, and transcriptomic assays were performed on calli with different browning degrees (T1, T2, and T3). The results of histological staining revealed that the brown callus cells had obvious lignification and accumulation of polyphenols. Widely targeted metabolomics revealed 1190 differentially accumulated metabolites (DAMs), with 53 DAMs annotated as phenylpropanoids and flavonoids. Comparative transcriptomics revealed differentially expressed genes (DEGs) of the T2 vs. T1 associated with the biosynthesis and regulation of flavonoids and transcription factors in Camellia hainanica. Among them, forty-four enzyme genes associated with flavonoid biosynthesis were identified, including phenylalaninase (PAL), 4-coumaroyl CoA ligase (4CL), naringenin via flavanone 3-hydroxylase (F3H), flavonol synthase (FLS), Chalcone synthase (CHS), Chalcone isomerase (CHI), hydroxycinnamoyl-CoA shikimate transferase (HCT), Dihydroflavonol reductase (DFR), anthocyanin reductase (LAR), anthocyanin synthetase (ANS), and anthocyanin reductase (ANR). Related transcription factors R2R3-MYB, basic helix-loop-helix (bHLH), and WRKY genes also presented different expression patterns in T2 vs. T1. These results indicate that the browning of calli in Camellia hainanica is regulated at both the transcriptional and metabolic levels. The oxidation of flavonoids and the regulation of related structural genes and transcription factors are crucial decisive factors. This study preliminarily revealed the molecular mechanism of the browning of the callus of Camellia hainanensis, and the results can provide a reference for the anti-browning culture of Camellia hainanica callus. Full article
(This article belongs to the Section Molecular Plant Sciences)
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<p>Classification and histological observation of callus browning in <span class="html-italic">Camellia hainanica</span>. (<b>A</b>) Unbrowning callus (T1) morphology, safranin O-fast green- and toluidine blue-stained sections. (<b>B</b>) Browning callus (T2) morphology, safranin O-fast green, and toluidine blue-stained sections. (<b>C</b>) Severe browning callus (T3) morphology, safranin O-fast green- and toluidine blue-stained sections. Note: In the stained safranin O-fast green sections, arrows indicate red-stained lignified matter; in the toluidine blue-stained sections, arrows indicate the accumulation of green-colored polyphenolic materials.</p>
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<p>Metabolome profiling in <span class="html-italic">Camellia hainanica</span> callus at different browning stages. (<b>A</b>) PCA of metabolites in the T1, T2, and T3 phases of the camellia callus; (<b>B</b>) Proportions of all metabolic components identified in the callus; (<b>C</b>) Cluster heatmaps of all differentially abundant metabolites.</p>
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<p>Differential expression of metabolites in <span class="html-italic">Camellia hainanica</span> callus. (<b>A</b>) Histogram of DAMs up- and downregulated in different groups. (<b>B</b>) Venn diagram of the DAMs for different groups. (<b>C</b>) KEGG enrichment analysis of DAMs in the T2 vs. T1 comparison. (<b>D</b>) KEGG enrichment analysis of DAMs in the T3 vs. T2 comparison. (<b>E</b>) Fold changes in the 40 most up- or downregulated DAMs in the T2 vs. T1 comparison. (<b>F</b>) Fold changes in the top 20 most up- or downregulated DAMs in the T3 vs. T2 comparison. Note: The most upregulated and downregulated DAMs are shown in red and blue, respectively.</p>
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<p>Correlation study of metabolites of <span class="html-italic">Camellia hainanica</span> callus via WGCNA. (<b>A</b>) Cluster dendrogram of each sample. (<b>B</b>) Module–trait relationship heatmap; each cell contains the corresponding correlation and <span class="html-italic">p</span> value. The table is color-coded by correlation according to the color legend.</p>
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<p>Integrated transcriptomic analysis of <span class="html-italic">Camellia hainanica</span> calli at different browning stages. (<b>A</b>) Numbers of upregulated and downregulated DEGs for each comparison. (<b>B</b>) KEGG enrichment analysis of DEGs in the T2 vs. T1 comparison. (<b>C</b>) GO enrichment analysis of DEGs in the T2 vs. T1 comparison.</p>
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<p>DEGs in the T2 vs. T1 comparison group for reference regulation and flavonoid biosynthesis. (<b>A</b>) Schematic representation of the relative expression levels of structural genes in the flavonoid biosynthesis pathway. The two columns of heatmaps from top to bottom represent the T2 and T1 stages, respectively. The lines of the heatmap represent different gene copies, and the diagonal arrows represent multistep enzyme reactions. (<b>B</b>) Thermograms of <span class="html-italic">MYB</span>, <span class="html-italic">bHLH</span>, and <span class="html-italic">WRKY</span> transcription factors with differential expression; red and blue indicate significant up–down and down–down, respectively.</p>
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<p>T2 vs. T1 metabolites and gene correlation analysis diagram. (<b>A</b>) Nine-quadrant map of metabolites and gene regulation of T2 vs. T1. (<b>B</b>) Metabolic pathway map of T2 vs. T1 metabolites and gene regulation.</p>
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14 pages, 517 KiB  
Article
Green Extraction of Bioactive Compounds from Apple Pomace from the Cider Industry
by Rosa Pando Bedriñana, Roberto Rodríguez Madrera, María Dolores Loureiro Rodríguez, Karelmar López-Benítez and Anna Picinelli Lobo
Antioxidants 2024, 13(10), 1230; https://doi.org/10.3390/antiox13101230 - 14 Oct 2024
Viewed by 426
Abstract
The cider-making industry in Asturias generates between 9000 and 12,000 tons of apple pomace per year. This by-product, the remains of the apple pressing, and made up of peel, flesh, seeds and stems, is a valuable material, containing substantial amounts of antioxidant compounds [...] Read more.
The cider-making industry in Asturias generates between 9000 and 12,000 tons of apple pomace per year. This by-product, the remains of the apple pressing, and made up of peel, flesh, seeds and stems, is a valuable material, containing substantial amounts of antioxidant compounds associated with healthy properties. Polyphenols such as dihydrochalcones and quercetin glycosides, and triterpenic acids, among which ursolic acid is a major compound, are the main antioxidant families described in apple pomace. The simultaneous recovery of those families has been accomplished by low frequency ultrasound-assisted extraction. Working extraction conditions were optimised by response surface methodology (RSM): time, 5.1 min; extractant composition, 68% ethanol in water; solid/liquid ratio, 1/75 and ultrasonic wave amplitude, 90%. This procedure was further applied to analyse those components in the whole apple pomace (WAP), apple peel (AP) and apple flesh (AF). On average, dry WAP contained almost 1300 µg/g of flavonols, 1200 µg/g of dihydrochalcones and 4200 µg/g of ursolic acid. These figures increased in the apple peel to, respectively 2500, 1400 and 8500 µg/g dry matter. Two linear multivariate regression models allowed the antioxidant activity of apple by-products to be predicted on the basis of their bioactive composition. The results derived from this study confirm the potential of industrial cider apple pomace as a source of high-value bioactive compounds, and the feasibility of the ultrasound-assisted extraction technique to recover those components in a simple and efficient way. Full article
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<p>Response surfaces calculated from experimental data: (<b>a</b>) Ursolic acid content (area/mg ratio); (<b>b</b>) Total phenolic content (TPC, mg gallic acid/g dry weight). Mass sample: 0.4 g and amplitude of sonication: 90%.</p>
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12 pages, 259 KiB  
Protocol
A Versatile Ultra-High-Performance Liquid Chromatography-Full-Scan High-Resolution Mass Spectrometry Method to Quantify Wine Polyphenols
by Damien Flores, Emmanuelle Meudec, Aécio Luís de Sousa Dias and Nicolas Sommerer
Methods Protoc. 2024, 7(5), 82; https://doi.org/10.3390/mps7050082 - 10 Oct 2024
Viewed by 407
Abstract
Polyphenols are responsible for wine colour and astringency, and, as antioxidants, they also have beneficial health properties. In this work, we developed a robust full-scan high-resolution mass spectrometry method for the quantification of 90 phenolic compounds in wine samples (either red, rosé, or [...] Read more.
Polyphenols are responsible for wine colour and astringency, and, as antioxidants, they also have beneficial health properties. In this work, we developed a robust full-scan high-resolution mass spectrometry method for the quantification of 90 phenolic compounds in wine samples (either red, rosé, or white wine), using a UHPLC-OrbitrapTM system. With this method, we could conduct a detailed analysis of phenolic compounds in red, rosé, and white wines with great selectivity due to sub-ppm mass accuracy. Moreover, accessing the full-scan spectrum enabled us to monitor all the other compounds detected in the sample, facilitating the adaptability of this method to new phenolic compounds if needed. Full article
(This article belongs to the Section Biochemical and Chemical Analysis & Synthesis)
24 pages, 4488 KiB  
Article
Integrated Metabolome and Transcriptome Analyses Reveal the Mechanisms Regulating Flavonoid Biosynthesis in Blueberry Leaves under Salt Stress
by Bin Ma, Yan Song, Xinghua Feng, Pu Guo, Lianxia Zhou, Sijin Jia, Qingxun Guo and Chunyu Zhang
Horticulturae 2024, 10(10), 1084; https://doi.org/10.3390/horticulturae10101084 - 9 Oct 2024
Viewed by 398
Abstract
The flavonoids play important roles in plant salt tolerance. Blueberries (Vaccinium spp.) are extremely sensitive to soil salt increases. Therefore, improving the salt resistance of blueberries by increasing the flavonoid content is crucial for the development of the blueberry industry. To explore [...] Read more.
The flavonoids play important roles in plant salt tolerance. Blueberries (Vaccinium spp.) are extremely sensitive to soil salt increases. Therefore, improving the salt resistance of blueberries by increasing the flavonoid content is crucial for the development of the blueberry industry. To explore the underlying molecular mechanism, we performed an integrated analysis of the metabolome and transcriptome of blueberry leaves under salt stress. We identified 525 differentially accumulated metabolites (DAMs) under salt stress vs. control treatment, primarily including members of the flavonoid class. We also identified 20,920 differentially expressed genes (DEGs) based on transcriptome data; of these, 568 differentially expressed transcription factors (TFs) were annotated, and bHLH123, OsHSP20, and HSP20 TFs might be responsible for blueberry leaf salt tolerance. DEGs involved in the flavonoid biosynthesis pathway were significantly enriched at almost all stages of salt stress. Salt treatment upregulated the expression of most flavonoid biosynthetic pathway genes and promoted the accumulation of flavonols, flavonol glycosides, flavans, proanthocyanidins, and anthocyanins. Correlation analysis suggested that 4-coumarate CoA ligases (4CL5 and 4CL1) play important roles in the accumulation of flavonols (quercetin and pinoquercetin) and flavan-3-ol (epicatechin and prodelphinidin C2) under salt stress, respectively. The flavonoid 3′5′-hydroxylases (F35H) regulate anthocyanin (cyanidin 3-O-beta-D-sambubioside and delphinidin-3-O-glucoside chloride) biosynthesis, and leucoanthocyanidin reductases (LAR) are crucial for the biosynthesis of epicatechin and prodelphinidin C2 during salt stress. Taken together, it is one of the future breeding goals to cultivate salt-resistant blueberry varieties by increasing the expression of flavonoid biosynthetic genes, especially 4CL, F35H, and LAR genes, to promote flavonoid content in blueberry leaves. Full article
(This article belongs to the Special Issue Advances in Developmental Biology in Tree Fruit and Nut Crops)
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<p>Metabolomic substances in blueberry leaves in response to salt stress identified by non-targeted metabolomic profiling in positive and negative ion mode. (<b>a</b>) Number of metabolomic substances in positive (Pos) and negative (Neg) ion modes. (<b>b</b>) Classification of the detected metabolomic substances.</p>
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<p>Differentially accumulated metabolites (DAMs) in blueberry leaves in response to salt stress identified by non-targeted metabolomic profiling in positive and negative ion mode. (<b>a</b>) Number of DAMs detected in positive (Pos) and negative (Neg) ion mode and total number of DAMs. (<b>b</b>) Venn diagram showing the extent of overlap between DAMs across pairwise comparisons. Pink, DAMs for 6 h vs. 0 h; yellow, DAMs for 12 h vs. 0 h; green, DAMs for 24 h vs. 0 h; blue, DAMs for 48 h vs. 0 h. (<b>c</b>) Classification of the DAMs.</p>
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<p>Enriched KEGG pathways of differentially accumulated metabolites (DAMs) in blueberry leaves in response to salt stress revealed by non-targeted metabolomic profiling. (<b>a</b>) Venn diagram of significantly enriched KEGG pathways of the DAMs. Pink, DAMs for 0 h vs. 6 h; yellow, DAMs for 0 h vs. 12 h; green, DAMs for 0 h vs. 24 h; blue, DAMs for 0 h vs. 48 h. (<b>b</b>) The number of significantly enriched KEGG pathways among the DAMs. (<b>c</b>) The top 20 enriched KEGG pathways among the DAMs, and rich factors in different comparison groups.</p>
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<p>Enriched KEGG pathways of differentially accumulated metabolites (DAMs) in blueberry leaves in response to salt stress revealed by non-targeted metabolomic profiling. (<b>a</b>) Venn diagram of significantly enriched KEGG pathways of the DAMs. Pink, DAMs for 0 h vs. 6 h; yellow, DAMs for 0 h vs. 12 h; green, DAMs for 0 h vs. 24 h; blue, DAMs for 0 h vs. 48 h. (<b>b</b>) The number of significantly enriched KEGG pathways among the DAMs. (<b>c</b>) The top 20 enriched KEGG pathways among the DAMs, and rich factors in different comparison groups.</p>
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<p>Differentially expressed genes (DEGs) in blueberry leaves in response to salt stress identified by transcriptome deep sequencing (RNA-seq). (<b>a</b>) Number of DEGs in response to salt stress. Up-regulated, upregulated DEGs; Down-regulated, downregulated DEGs; Total, total DEGs. (<b>b</b>) Venn diagram showing the extent of overlap between DEGs across pairwise comparisons. Pink, DEGs for 0 h vs. 6 h; yellow, DEGs for 0 h vs. 12 h; green, DEGs for 0 h vs. 24 h; blue, DEGs for 0 h vs. 48 h.</p>
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<p>GO and KEGG pathway enrichment analysis of differentially expressed genes (DEGs) in blueberry leaves in response to salt stress identified by transcriptome deep sequencing (RNA-seq). (<b>a</b>) Venn diagrams of GO terms and significantly enriched KEGG pathways among the DEGs. Pink, DEGs for 0 h vs. 6 h; yellow, DEGs for 0 h vs. 12 h; green, DEGs for 0 h vs. 24 h; blue, DEGs for 0 h vs. 48 h. (<b>b</b>) GO terms of DEGs in different comparison groups. Green bar, biological process; blue bar, molecular function; red bar, cellular component. (<b>c</b>) The top 20 enriched KEGG pathways of DEGs in different comparison groups.</p>
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<p>GO and KEGG pathway enrichment analysis of differentially expressed genes (DEGs) in blueberry leaves in response to salt stress identified by transcriptome deep sequencing (RNA-seq). (<b>a</b>) Venn diagrams of GO terms and significantly enriched KEGG pathways among the DEGs. Pink, DEGs for 0 h vs. 6 h; yellow, DEGs for 0 h vs. 12 h; green, DEGs for 0 h vs. 24 h; blue, DEGs for 0 h vs. 48 h. (<b>b</b>) GO terms of DEGs in different comparison groups. Green bar, biological process; blue bar, molecular function; red bar, cellular component. (<b>c</b>) The top 20 enriched KEGG pathways of DEGs in different comparison groups.</p>
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<p>Differentially expressed transcription factors (TF) in blueberry leaves in response to salt stress identified by transcriptome deep sequencing (RNA-seq).</p>
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<p>Phenylpropanoid and flavonoid KEGG biosynthetic pathways in blueberry leaves under salt stress. Red and magenta fonts indicate upregulated and downregulated metabolites or genes, respectively; blue fonts indicate both upregulated and downregulated metabolites or genes; and black fonts indicate no significant changes in response to salt stress. Heatmaps show the expression of DEGs or the accumulation of DAMs. Colored bars on the upper right indicate low expression (pink) or high expression (blue) of differentially accumulated metabolites (DAM) based on log<sub>10</sub> (peak intensity). Colored bars on the right indicate low expression (green) or high expression (red) of differentially expressed genes (DEGs) based on scale normalized log<sub>10</sub> (FPKM). PAL, phenylalanine ammonia-lyase; C4H, cinnamate 4-hydroxylase; 4CL, 4-coumarate CoA ligase; HCT, shikimate O-hydroxycinnamoyltransferase; CSE, caffeoyl shikimate esterase; COMT, caffeic acid 3-O-methyltransferase; CHS, chalcone synthase; CHI, chalcone isomerase; F3H, flavanone 3-hydroxylase; F3′H, flavonoid 3′-hydroxylase; F3′5′H, flavonoid 3′5′-hydroxylase; FLS, flavonol synthase; DFR, dihydroflavonol 4-reductase; ANS, anthocyanidin synthase; ANR, anthocyanidin reductase; LAR, leucoanthocyanidin reductase; UFGT, UDP-glucose flavonoid 3-O-glucosyl transferase; UGT, UDP-glycosyltransferase.</p>
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15 pages, 1399 KiB  
Article
Bioactives in Berry Fruits with Emphasis on In Vitro Bioaccessibility for Human Nutrition
by Iulia Varzaru, Arabela Elena Untea, Alexandra Gabriela Oancea, Mihaela Saracila and Petru Alexandru Vlaicu
Separations 2024, 11(10), 286; https://doi.org/10.3390/separations11100286 - 6 Oct 2024
Viewed by 357
Abstract
This study aimed to investigate the bioaccessibility and biostability of carotenoids, vitamin E isomers, and individual polyphenolic compounds after the in vitro gastrointestinal digestion of two types of berries (raspberry and blackberry fruits). The results of the polyphenols analysis showed that raspberry fruits [...] Read more.
This study aimed to investigate the bioaccessibility and biostability of carotenoids, vitamin E isomers, and individual polyphenolic compounds after the in vitro gastrointestinal digestion of two types of berries (raspberry and blackberry fruits). The results of the polyphenols analysis showed that raspberry fruits contained higher concentrations of hydroxybenzoic acids, hydroxycinnamic acids, flavanols, and flavonols compared to blackberry fruits, but exhibited the lowest bioaccessibility values for all the studied polyphenol classes. Ellagic acid represented 13.63% and 2.65% of the hydroxybenzoic acids in raspberry and blackberry fruits. The hydroxybenzoic acids exhibited the highest bioaccessibility index in the intestinal phase of both types of berries, and gallic acid emerged as one of the most bioaccessible phenolic compounds. The bioaccessibility of carotenoids ranged between 15.7 and 17.30% for lutein, 5.52 and 7.56% for astaxanthin, and 7.85 and 9.93% for canthaxanthin, with elevated values being observed in raspberry fruits. Although vitamin E and carotenoids follow a similar path for absorption, the bioaccessibility of vitamin E isomers was higher than that of carotenoids, with γ-tocopherol being the most bioaccessible isomer in both raspberries and blackberries. Knowing the bioaccessibility of food constituents during digestion is crucial, as the potential effectiveness of bioactives for human health largely depends on the bioavailability of these molecules. Full article
(This article belongs to the Special Issue Isolation and Identification of Biologically Active Natural Compounds)
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<p>Chromatograms of the phenolic compounds in raspberry fruits (<b>a</b>) and blackberry fruits before digestion. (<b>b</b>) Peaks identification: 1—gallic acid, 2—epigallocatechin, 3—catechin, 4—chlorogenic acid, 5—vanillic acid, 6—caffeic acid, 7—syringic acid, 8—epicatechin, 9—3-hydroxybenzoic acid, 10—rutin, 11—coumaric acid, 12—ellagic acid, 13—methoxycinnamic acid, 14—ferulic acid, 15—protocatechuic acid, 16—resveratrol, 17—quercetin, and 18—cinnamic acid.</p>
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<p>Bioaccessibility of the polyphenols classes in the intestinal phase of the analyzed berries. RF represents raspberry fruits; BF represents blackberry fruits. The results are expressed as mean ± standard deviation (n = 3). Significant differences were considered at <span class="html-italic">p</span> &lt; 0.05.</p>
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<p>Bioaccessibility of carotenoids in the intestinal phase of the analyzed berries. RF represents raspberry fruits; BF represents blackberry fruits. The results are expressed as mean ± standard deviation (n = 3). Significant differences were considered at <span class="html-italic">p</span> &lt; 0.05.</p>
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<p>Biostability of carotenoids in the intestinal phase of the analyzed berries. RF represents raspberry fruits; BF represents blackberry fruits. The results are expressed as mean ± standard deviation (n = 3). Significant differences were considered at <span class="html-italic">p</span> &lt; 0.05.</p>
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<p>Bioaccessibility of vitamin E isomers in the intestinal phase of the analyzed berries. RF represents raspberry fruits; BF represents blackberry fruits. The results are expressed as mean ± standard deviation (n = 3). Significant differences were considered at <span class="html-italic">p</span> &lt; 0.05.</p>
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<p>Biostability of vitamin E isomers in the intestinal phase of the analyzed berries. RF represents raspberry fruits; BF represents blackberry fruits. The results are expressed as mean ± standard deviation (n = 3). Significant differences were considered at <span class="html-italic">p</span> &lt; 0.05.</p>
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18 pages, 1660 KiB  
Article
Comparative Evaluation of the Phytochemical Composition of Fruits of Ten Haskap Berry (Lonicera caerulea var. kamtschatica Sevast.) Cultivars Grown in Poland
by Natalia Żurek, Stanisław Pluta, Łukasz Seliga, Sabina Lachowicz-Wiśniewska and Ireneusz Tomasz Kapusta
Agriculture 2024, 14(10), 1734; https://doi.org/10.3390/agriculture14101734 - 1 Oct 2024
Viewed by 742
Abstract
The aim of this study was to investigate the qualitative and quantitative fruit profiles of ten cultivars (cvs.) of haskap berry (Lonicera caerulea var. kamtschatica Sevast.) to determine their antioxidant activity (ABTS test, CUPRAC test, ability to capture superoxide (O2˙ [...] Read more.
The aim of this study was to investigate the qualitative and quantitative fruit profiles of ten cultivars (cvs.) of haskap berry (Lonicera caerulea var. kamtschatica Sevast.) to determine their antioxidant activity (ABTS test, CUPRAC test, ability to capture superoxide (O2˙) and hydroxyl radicals (OH˙)), cytotoxic activity (against cancer cell lines breast, MCF-7; colon, HT-29; and melanoma, SK-Mel-28) and physicochemical properties. Most of the selected cultivars had not previously been analyzed for these properties. A total of 19 polyphenolic compounds were identified in the fruits of the tested genotypes, with a quantitative range of 2166.3–3597.0 µg/g. The polyphenol profile was dominated by anthocyanins (90.0–92.4%), and the remaining classes occurred in the following order: phenolic acids > flavonols > flavan-3-ols. The highest concentrations of these polyphenol groups were found in the cultivars ‘Honeybee’, ‘Sinij Uties’ and ‘Usłada’. The fruits of these cultivars were also characterized by the highest antioxidant activity (546.6–683.5 µg/mL for O2˙ and 541.2–652.1 µg/mL for OH˙) and cytotoxic activity (103.6–649.2 µg/mL). The data obtained indicate that the fruits of the new haskap cultivars are a good source of bioactive compounds with possible health-promoting properties. Full article
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<p>The content of individual classes of polyphenols (anthocyanins, phenolic acids, flavan-3-ols, flavonols) estimated by the UPLC-PDA-MS/MS method in fruits of ten haskap berry cultivars: <b>1</b>. ‘Boreal Beauty’; <b>2</b>. ‘Boreal Beast’; <b>3</b>. ‘Boreal Blizzard’; <b>4</b>. ‘Aurora’; <b>5</b>. ‘Honeybee’; <b>6</b>. ‘Vostorg’; <b>7</b>. ‘Jugana’; <b>8</b>. ‘Usłada’; <b>9</b>. ‘Lawina’; <b>10</b>. ‘Sinij Uties’. Values are presented as mean and SD. Measurements were made in 3 repetitions. Statistical analysis (a–c) was performed using Duncan’s test (<span class="html-italic">p</span> &lt; 0.05).</p>
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<p>Pearson’s correlation index for fruits of haskap berry cultivars, showing the strength of the relationship between variables such as antioxidant activity (ABTS, CUPRAC, O<sub>2</sub>˙<sup>−</sup>, OH˙), cytotoxic activity (MCF-7, HT-29, SK-Mel-28), classes of individual polyphenols assessed spectrophotometrically (TPC, TFC, TAC) and chromatographically (anthocyanins, other polyphenols), and compounds identified at the highest concentrations (cyanidin 3-<span class="html-italic">O</span>-glucoside, cyanidin 3,5-<span class="html-italic">O</span>-diglucoside, cyanidin 3-<span class="html-italic">O</span>-rutinoside, chlorogenic acid, quercetin 3-<span class="html-italic">O</span>-rutinoside, procyanidin dimer B-type). A red color indicates a positive correlation and blue indicates a negative correlation. Antioxidant and cytotoxic activity was mainly dependent on the content of anthocyanins, especially cyanidin 3-<span class="html-italic">O</span>-glucoside.</p>
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<p>Principal component analysis of data regarding the physicochemical properties, content of phenolic compounds and health-promoting activity of haskap berries. The cultivars ‘Honeybee’, ‘Sinij Uties’ and ‘Usłada’ were characterized by the highest values for antioxidant and cytotoxic activity and phenolic compound content.</p>
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12 pages, 2498 KiB  
Article
Identification of Sinapic Acid Derivatives from Petit Vert Leaves and Their Effects on Glucose Uptake in C2C12 Murine Myoblasts
by Shizuo Yamada, Tsutomu Warashina, Osamu Shirota, Yoshihisa Kato and Toshiyuki Fukuda
Biomolecules 2024, 14(10), 1246; https://doi.org/10.3390/biom14101246 - 1 Oct 2024
Viewed by 456
Abstract
Petit vert (scientific name: Brassica oleracea var. gemmifera DC. × Brassica oleracea var. acephala DC.) is a new variety of vegetable created by crossbreeding kale and brussel sprouts (Brassica oleracea species). The present study aimed to identify biologically active compounds in extracts of [...] Read more.
Petit vert (scientific name: Brassica oleracea var. gemmifera DC. × Brassica oleracea var. acephala DC.) is a new variety of vegetable created by crossbreeding kale and brussel sprouts (Brassica oleracea species). The present study aimed to identify biologically active compounds in extracts of the outer leaves of Petit vert by purification and to examine their biological activities. The dried and powdered outer leaves of Petit vert were extracted, fractionated, and purified to isolate active compounds. Mass spectrometry (MS) was used to identify the compounds, and nuclear magnetic resonance (NMR) spectroscopy was performed to elucidate their structures. The compounds isolated from Petit vert leaves were glycosides that contained kaempferol, quercetin (flavonol), or sinapic acid (phenylpropanoid). Glucose uptake in cultured C2C12 murine myoblasts in the absence of insulin was significantly increased by these compounds, kaempferol, sinapic acid, and ferulic acid, while uptake in the presence of insulin was also significantly increased by compounds 3 and 4, kaempferol, and sinapic acid. The effect was not necessarily concentration-dependent, and some agents decreased the glucose uptake at higher concentrations. The present study reports for the first time the isolation of five compounds containing sinapic acid from the outer leaves of Petit vert and their stimulation of glucose uptake in cultured C2C12 murine myoblasts. The results obtained herein suggest the potential of these compounds to effectively attenuate hyperglycemia and maintain muscle strength by promoting glucose metabolism in muscle cells. Full article
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<p>Petit vert (scientific name: <span class="html-italic">Brassica oleracea var. gemmifera</span> DC. × <span class="html-italic">Brassica oleracea</span> var. <span class="html-italic">acephala</span> DC.). (<b>1</b>) Petit vert. (<b>2</b>) Side shoots. (<b>3</b>) Leaf.</p>
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<p>Observed key <sup>1</sup>H-<sup>1</sup>H COSY, HMBC, and ROE correlations of compound <b>2</b>.</p>
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<p>Structures of compounds <b>1</b>–<b>10</b>.</p>
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<p>HPLC profiles of MeOH extracts from Petit vert leaf (<b>a</b>) and Petit vert side shoots (<b>b</b>). HPLC conditions [column: Cosmosil 2.5Cholester (2.5 µm), i.d. 3.0 × 100 mm (NACALAI TESQUE, INC.); mobile phase: A 0.1%TFA in water, B CH<sub>3</sub>CN, gradient, 0–20 min: 6–11% B linear, 20–36 min: 11–27% B linear, 36–45 min: 27% B; and flow rate: 0.75 mL/min; Detection: UV 330 nm; [Column temperature: 40 ℃].</p>
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12 pages, 1743 KiB  
Article
Protective Effects of Wild Sulla coronaria (Fabaceae) Flowers Phytocomplex in Human Dermal Fibroblasts Stimulated with Interleukin-1β
by Giuseppe Antonio Malfa, Simone Bianchi, Vivienne Spadaro, Ekaterina Kozuharova, Pasquale Marino, Francesco Pappalardo, Claudia Di Giacomo and Rosaria Acquaviva
Plants 2024, 13(19), 2748; https://doi.org/10.3390/plants13192748 - 30 Sep 2024
Viewed by 417
Abstract
Sulla coronaria is indigenous to the Mediterranean region. It is grown as fodder in southern Italy because it contains various secondary metabolites with beneficial activities on animals. Recently, its potential use in cosmeceutical treatments for skin problems was reported. In this scenario, to [...] Read more.
Sulla coronaria is indigenous to the Mediterranean region. It is grown as fodder in southern Italy because it contains various secondary metabolites with beneficial activities on animals. Recently, its potential use in cosmeceutical treatments for skin problems was reported. In this scenario, to contribute to a possible cosmeceutical application, we characterized the phytochemical profile of Sulla coronaria flowers’ hydroalcoholic extract by HPLC-DAD, Folin-Ciocalteu, Aluminum Chloride methods, DPPH assay, and, for the first time, we evaluated the antioxidant and anti-inflammatory activities on dermal fibroblasts. The phytochemical analysis confirmed the significant content of phenolic compounds (TPC 69.8 ± 0.6 mg GAE/g extract, TFC 15.07 mg CE/g extract) and the remarkable presence of rutin, quercetin, and isorhamnetin derivatives that give to the phytocomplex a good antioxidant activity as highlighted by the DPPH assay (IC50 of 8.04 ± 0.5 µg/mL). Through the reduction in NO• and ROS levels in human dermal fibroblasts, the biological tests demonstrated both the safety of the extract and its ability to counteract the inflammatory state generated by Interleukin-1β exposure. Our findings indicate that the antioxidant activities of the phytocomplex are strictly related to the anti-inflammatory action of the Sulla coronaria flowers extract, confirming that this plant could be a valuable source of bioactive molecules for cosmeceutical and nutraceutical applications. Full article
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<p>Blooming of wild <span class="html-italic">Sulla coronaria</span> plant at the collection site (Corleone, Palermo, Italy).</p>
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<p>HPLC-DAD phytochemical fingerprint of <span class="html-italic">Sulla coronaria</span> flower hydroalcoholic extract. Column: Ascentis Express C18, 15 cm × 4.6 mm, 2.7 µm d.p. The numbers indicating peaks refer to the identified compounds reported in <a href="#plants-13-02748-t002" class="html-table">Table 2</a>.</p>
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<p>Aglycone chemical structures of the identified compounds in <span class="html-italic">Sulla coronaria</span> flower hydroalcoholic extract.</p>
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<p>Cytotoxic effect of <span class="html-italic">Sulla coronaria</span> flower hydroalcoholic extract on HDF cells. An MTT test was performed on HDFs treated with different concentrations of extract (from 10 to 1000 µg/mL) for 24 h. Data are represented as the means ± S.D. of three independent experiments. Confidence intervals calculated by one-way ANOVA test: * Significant vs. untreated control cells.</p>
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<p>ROS production in HDF untreated cells (Ctr), treated for 12 h with IL-1β (10 ng/mL), and pre-treated for 24 h with the extract (50–100–200 μg/mL). Results are expressed as the percentage of the intensity of fluorescence (I.F.) <span class="html-italic">vs</span> Ctr. Values are the mean ± S.D. of three experiments in triplicate. Confidence intervals calculated by one-way ANOVA test: * Significant vs. untreated control cells: <span class="html-italic">p</span> &lt; 0.05; # Significant vs. IL-1β-Stimulated cells: <span class="html-italic">p</span> &lt; 0.05.</p>
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<p>Effect of <span class="html-italic">Sulla coronaria</span> flower extract on NO• production in HDF cells. A Griess assay was performed on the supernatant of IL-1β-stimulated cells non-treated and treated with the extract (50, 100, and 200 µg/mL) for 24 h. Data are represented as the means ± SD of three independent experiments. Confidence intervals calculated by one-way ANOVA test: * Significant vs. untreated control cells: <span class="html-italic">p</span> &lt; 0.05; # Significant vs. IL-1β-Stimulated cells: <span class="html-italic">p</span> &lt; 0.05.</p>
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14 pages, 4987 KiB  
Article
FtMYB163 Gene Encodes SG7 R2R3-MYB Transcription Factor from Tartary Buckwheat (Fagopyrum tataricum Gaertn.) to Promote Flavonol Accumulation in Transgenic Arabidopsis thaliana
by Hanmei Du, Jin Ke, Xiaoqian Sun, Lu Tan, Qiuzhu Yu, Changhe Wei, Peter R. Ryan, An’hu Wang and Hongyou Li
Plants 2024, 13(19), 2704; https://doi.org/10.3390/plants13192704 - 27 Sep 2024
Viewed by 306
Abstract
Tartary buckwheat (Fagopyrum tataricum Gaertn.) is a coarse grain crop rich in flavonoids that are beneficial to human health because they function as anti-inflammatories and provide protection against cardiovascular disease and diabetes. Flavonoid biosynthesis is a complex process, and relatively little is [...] Read more.
Tartary buckwheat (Fagopyrum tataricum Gaertn.) is a coarse grain crop rich in flavonoids that are beneficial to human health because they function as anti-inflammatories and provide protection against cardiovascular disease and diabetes. Flavonoid biosynthesis is a complex process, and relatively little is known about the regulatory pathways involved in Tartary buckwheat. Here, we cloned and characterized the FtMYB163 gene from Tartary buckwheat, which encodes a member of the R2R3-MYB transcription factor family. Amino acid sequence and phylogenetic analysis indicate that FtMYB163 is a member of subgroup 7 (SG7) and closely related to FeMYBF1, which regulates flavonol synthesis in common buckwheat (F. esculentum). We demonstrated that FtMYB163 localizes to the nucleus and has transcriptional activity. Expression levels of FtMYB163 in the roots, stems, leaves, flowers, and seeds of F. tataricum were positively correlated with the total flavonoid contents of these tissues. Overexpression of FtMYB163 in transgenic Arabidopsis enhanced the expression of several genes involved in early flavonoid biosynthesis (AtCHS, AtCHI, AtF3H, and AtFLS) and significantly increased the accumulation of several flavonoids, including naringenin chalcone, naringenin-7-O-glucoside, eriodictyol, and eight flavonol compounds. Our findings demonstrate that FtMYB163 positively regulates flavonol biosynthesis by changing the expression of several key genes in flavonoid biosynthetic pathways. Full article
(This article belongs to the Section Plant Molecular Biology)
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<p>Multiple sequence alignment of FtMYB163. The transcription factors were FeMYBF1 (LC369592) from common buckwheat, FtMYB6 (QPC96978) from Tartary buckwheat, AtMYB12 (AEC10843) from Arabidopsis, VvMYBF1 (FJ948477) from grape, and CsMYBF1 (KT727073) from citrus. Identical (100%), conservative (75–99%), and blocks (50–74%) of similar amino acid residues are shaded in deep blue, cherry red, and cyan, respectively. The R2/R3 SANT domain and SG7 motif1/2 are indicated in the red line and red box, respectively.</p>
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<p>Phylogenetic analysis of FtMYB163. GeneBack accession numbers are listed as follows: AtMYB58 (NP_173098), AtMYB63 (NP_001321204), LlMYB1 (ADY38393), ZmMYB31 (NP_001105949), ZmMYB42 (NP_001106009), MdMYB3 (AEX08668), AtMYB7 (NP_179263), AtMYB4 (AAC83582), AtMYB8 (NP_849749), AtMYB32 (NP_195225), AtMYB3 (NP_564176), FtMYB2 (AEC32976), FaMYB11 (USN17649), FaMYB9 (USN17648), MdMYB9 (NP_001280749), PtMYB134 (ACR83705), VvMYBPA1 (NP_001268160), VvMYBPA2 (NP_001267953), PpMYB10 (ADK73605), AN2 (BAP28593), ANT1 (WDP81135), IbMYB1 (BAG68211), AtMYB113 (NP_176811), AtMYB114 (NP_176812), GtMYBP3 (AB733016), MdMYB22 (DQ074470), AtMYB111 (AAK97396), AtMYB11 (NP_191820), MsMYB (AQR58379), CcMYB12 (AXF92691), AtMYB90 (AAG42002), AtPAP1 (NP_172830), AtMYB75 (NP_176057), AtMYB43 (NP_197163), AtMYB20 (NP_176797), FtMYB1 (AEC32973), FtMYB31 (AIZ97491). FtMYB163 is highlighted with a red dot.</p>
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<p>Subcellular localization and transcription activation activities of FtMYB163. (<b>A</b>) Subcellular localization of FtMYB163-GFP fusion protein in <span class="html-italic">Nicotiana benthamiana</span> leaves. GFP: Green fluorescent protein; DAPI: 4′,6-diamidino-2-phenylindole stain; 16318-hGFP was used as the control. Scale bar: 20 μm. (<b>B</b>) Transcription activation analysis of FtMYB163 in yeast AH109 cells. The transformed cells were plated on an (<b>a</b>) SD/-Leu/-Trp, (<b>b</b>) SD/-Ade/-His/-Leu/-Trp, and (<b>c</b>) SD/-Ade/-His/-Leu/-Trp/x-α-gal medium and incubated in an incubator at 30 °C for 3~5 d. pGBKT7, negative control; pGBKT7-<span class="html-italic">53</span>, positive control.</p>
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<p>Expression pattern of <span class="html-italic">FtMYB163</span> and the total flavonoid content in Tartary buckwheat. The expression of <span class="html-italic">FtMYB163</span> in (<b>A</b>) R (roots), ST (stems), L (leaves), and F (flowers) at sprouts, six-leaf stage, and maturation stage and (<b>B</b>) in seeds at different developmental stages. (<b>C</b>) Gene expression clustering heat map of <span class="html-italic">FtMYB163</span> and Tartary buckwheat flavonoid biosynthesis structure. (<b>D</b>) <span class="html-italic">FtMYB163</span> expression analysis and (<b>E</b>) the total flavonoid content detection in each tissue at the corresponding period (as in (<b>C</b>)). (<b>F</b>) The correlation between the <span class="html-italic">FtMYB163</span> expression in different tissues and the content of total flavonoids. D4~D30, the seeds 4~30 days after flowering; L1, top one leaf of adult plants; L2, top three leaves of adult plants; S1, seeds before grouting; S2, seeds at filling stage; S3, mature seeds. Blue asterisks indicated the structural genes co-expressed with <span class="html-italic">FtMYB163</span> during the three seed development periods. The expression levels were evaluated by the 2<sup>−ΔΔCT</sup> method, and <span class="html-italic">FtActin7</span> was used as a reference gene. The values are represented as mean ± SD (n = 5) and marked with different letters to indicate statistically significant differences at <span class="html-italic">p</span> &lt; 0.05 (Tukey’s test).</p>
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<p>Characterization of T<sub>3</sub> transgenic <span class="html-italic">Arabidopsis</span> lines expressing <span class="html-italic">FtMYB163.</span> (<b>A</b>) Relative expression levels of <span class="html-italic">FtMYB163</span> in independent homozygous T<sub>3</sub> lines using qRT-PCR. <span class="html-italic">AtACT2</span> was used as a reference gene. Data show the mean ± SD of three biological replicates. Different letters indicate significant differences at <span class="html-italic">p</span> &lt; 0.05 (Student’s <span class="html-italic">t</span>-test). (<b>B</b>) Total flavonoid content of WT <span class="html-italic">Arabidopsis</span> and three transgenic T<sub>3</sub> lines expressing <span class="html-italic">FtMYB163</span> (OE-2, OE-5, and OE-7). Values are mean ± SD (n = 10), and different letters indicate significant differences at <span class="html-italic">p</span> &lt; 0.01 (Tukey’s test).</p>
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<p>Assessing how the expression of <span class="html-italic">FtMYB163</span> in <span class="html-italic">Arabidopsis</span> leaves affects the expression of endogenous genes in the flavonoid synthesis pathway. The relative expression of Arabidopsis genes (<b>A</b>) flavonol synthase (<span class="html-italic">AtFLS</span>), (<b>B</b>) chalcone synthase (<span class="html-italic">AtCHS</span>), (<b>C</b>) chalcone isomerase (<span class="html-italic">AtCHI</span>), (<b>D</b>) flavonoid 3-hydroxylase (<span class="html-italic">AtF3H</span>), (<b>E</b>) flavonoid 3′-hydroxylase (<span class="html-italic">AtF3′H</span>), (<b>F</b>) dihydroflavonol 4-reductase (<span class="html-italic">AtDFR</span>), and (<b>G</b>) anthocyanidin reductase (<span class="html-italic">AtANS</span>) were measured in WT and transgenic lines (OE-2, OE-5, and OE-7). Gene expression in the WT was set to 1.0 to provide fold changes in expression. The <span class="html-italic">AtACT2</span> gene was used as a reference. Values represent mean ± SD (n = 5), and different letters indicate significant differences (<span class="html-italic">p</span> &lt; 0.01) (Tukey’s test).</p>
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14 pages, 1616 KiB  
Article
Impacts of Electrolyzed Water Treatments on Bioactive Compounds and Microbial and Visual Quality of Minimally Processed ‘Granny Smith’ Apples
by Nandi E. Nyamende, Gunnar Sigge, Zinash A. Belay, Buhle Mpahleni and Oluwafemi J. Caleb
Appl. Sci. 2024, 14(19), 8696; https://doi.org/10.3390/app14198696 - 26 Sep 2024
Viewed by 471
Abstract
Ready-to-eat fresh-cut apples deteriorate rapidly in visual quality due to browning, leading to consumer rejection and food waste. In addition, minimal processing induces tissue damage and releases organic substrates, which could accelerate microbial growth. The present study evaluated the impacts of alkaline and [...] Read more.
Ready-to-eat fresh-cut apples deteriorate rapidly in visual quality due to browning, leading to consumer rejection and food waste. In addition, minimal processing induces tissue damage and releases organic substrates, which could accelerate microbial growth. The present study evaluated the impacts of alkaline and acidic electrolyzed water (AIEW and AEW) on natural microbial load and bioactive compounds on fresh-cut ‘Granny Smith’ apples. Minimally processed apples were dipped for 10 min in AEW and AIEW solutions (200 mg L−1), packed in PET containers with lids, and stored for 9 days at 2 °C. Overall, fresh-cut ‘Granny Smith’ apples treated with AEW significantly (p < 0.05) maintained higher total phenolics (99.4 ± 4.3 mg GAE L−1) and antioxidant capacity (79.5 ± 6.5 mg VitCE L−1) compared to the non-treated control samples (42.9 ± 5.1 mg GAE L−1, 31.9 ± 8.1 mg GAE L−1, respectively). Similarly, pretreatment with AIEW maintained the highest total flavonol content (55.71 ± 1.5 mg QE L−1) compared to the AEW-treated samples and control (p < 0.05). AEW pretreatment led to a 2 Log and a 1 Log decline in total aerobic mesophilic bacteria and yeasts and moulds, respectively. The best visual quality and highest visual score was maintained by AEW and followed by AIEW. This study further demonstrated the effectiveness of electrolyzed water treatments in minimizing browning and enhancing bioactive compounds in fresh-cut ‘Granny Smith’ apples. Full article
(This article belongs to the Special Issue Novel Approaches for Food Processing and Preservation)
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<p>(<b>A</b>) Visual scoring for colour changes and surface appearance (dryness) of treated and untreated samples during storage at 2 °C for 9 days and (<b>B</b>) picture of minimally processed ‘Granny Smith’ apples treated with AEW = acidic electrolyzed water (200 mg L<sup>−1</sup>); AIEW = alkaline electrolyzed water (200 mg L<sup>−1</sup>); and CO = control (untreated) after 9 days at 2 °C. Colour graphics only available online.</p>
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<p>Total phenolics concentration for treated (AEW and AIEW) and non-treated minimally processed ‘Granny Smith’ apples during storage at 2 °C and 95% RH for 9 days. Error bars represent standard deviation (SD) of mean values of treatments (<span class="html-italic">n</span> = 3) tested using Duncan multi-range test at 95% confident interval (<span class="html-italic">p</span> ≤ 0.05) and different lower-case letter indicate significant difference in means (<span class="html-italic">p</span> &lt; 0.05). Similar lower-case letters are not significantly different. Continuous dashed line indicates baseline measurement. Descriptions of treatments: AEW = acidic electrolyzed water (200 mg L<sup>−1</sup>); AIEW = alkaline electrolyzed water (200 mg L<sup>−1</sup>); and Control = non-treated.</p>
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<p>Effects of AEW and AIEW on total flavonol concentration of fresh-cut ‘Granny Smith’ apples during storage at 2 °C and 95% RH for 9 days. Error bars represent standard deviation (SD) of mean values of treatments (n = 3) tested using Duncan multi-range test at 95% confident interval (<span class="html-italic">p</span> ≤ 0.05) and different lower-case letter indicate significant difference in means (<span class="html-italic">p</span> &lt; 0.05). Similar lower-case letters are not significantly different. Continuous dashed line indicates baseline measurement. The descriptions of treatments: AEW = acidic electrolyzed water (200 mg L<sup>−1</sup>); AIEW = alkaline electrolyzed water (200 mg L<sup>−1</sup>).</p>
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<p>Effects of AEW and AIEW on fresh-cut ‘Granny Smith’ apples. Ferric reducing antioxidant power (FRAP) during storage at 2 °C and 95% RH for 9 days. Error bars represent standard deviation (SD) of mean values of treatments (n = 3) tested using the Duncan multi-range test at 95% confident interval (<span class="html-italic">p</span> ≤ 0.05) and different lower-case letters indicate significant difference in means (<span class="html-italic">p</span> &lt; 0.05). Similar lower-case letters are not significantly different. Continuous dashed line indicates baseline measurement. The descriptions of treatments: AEW = acidic electrolyzed water (200 mg L<sup>−1</sup>); AIEW = alkaline electrolyzed water (200 mg L<sup>−1</sup>).</p>
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<p>Effects of AEW and AIEW treatments on the fresh-cut ‘Granny Smith’ apple surface microbial load: (<b>A</b>) total aerobic mesophilic bacteria and (<b>B</b>) yeast and moulds, during storage at 2 °C, 95% RH for 9 days. Error bars represent standard deviation (SD) of mean values of treatments (n = 3) tested using the Duncan multi-range test at 95% confident interval (<span class="html-italic">p</span> ≤ 0.05) and different lower-case letters indicate significant difference in means (<span class="html-italic">p</span> &lt; 0.05). Similar lower-case letters are not significantly different. Continuous dashed line indicates baseline measurement. The descriptions of treatments: AEW = acidic electrolyzed water (200 mg L<sup>−1</sup>); AIEW = alkaline electrolyzed water (200 mg L<sup>−1</sup>).</p>
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<p>Correlation analysis of antioxidant capacity (FRAP), total flavonoids, and poly-phenol content of fresh-cut ‘Granny Smith’ apples. The red line indicates the trend line which shows the correlation of the variables. The blue dots represent the coefficient estimates from the trend line. Histogram highlights the variance and mean squared error.</p>
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41 pages, 3391 KiB  
Review
A Comprehensive Review of Molecular Mechanisms, Pharmacokinetics, Toxicology and Plant Sources of Juglanin: Current Landscape and Future Perspectives
by Magdalena Rutkowska, Martyna Witek and Monika A. Olszewska
Int. J. Mol. Sci. 2024, 25(19), 10323; https://doi.org/10.3390/ijms251910323 - 25 Sep 2024
Viewed by 681
Abstract
Juglanin (kaempferol 3-O-α-L-arabinofuranoside) is a flavonol glycoside occurring in many plants, including its commercial sources Juglans regia, Polygonum aviculare and Selliguea hastata. Recent extensive studies have explored the potential of using juglanin in various pathological conditions, including cardiovascular disorders, [...] Read more.
Juglanin (kaempferol 3-O-α-L-arabinofuranoside) is a flavonol glycoside occurring in many plants, including its commercial sources Juglans regia, Polygonum aviculare and Selliguea hastata. Recent extensive studies have explored the potential of using juglanin in various pathological conditions, including cardiovascular disorders, central nervous and skeletal system disorders, metabolic syndrome, hepatic injury, and cancers. The results indicated a wide range of effects, like anti-inflammatory, anti-oxidant, anti-fibrotic, anti-thrombotic, anti-angiogenic, hepatoprotective, hypolipidemic, hypoglycemic, anti-apoptotic (normal cells), and pro-apoptotic (cancer cells). The health-promoting properties of juglanin can be attributed to its influence on many signaling pathways, associated with SIRT1, AMPK, Nrf2, STING, TLR4, MAPKs, NF-κB, AKT, JAK, and their downstream genes. This review primarily summarizes the current knowledge of molecular mechanisms, pharmacokinetics, biocompatibility, and human use safety of juglanin. In addition, the most promising new plant sources and other existing challenges and prospects have also been reviewed and discussed, aiming to provide direction and rationale for the further development and broader pharmaceutical application of juglanin. Full article
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<p>The chemical structure of juglanin.</p>
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<p>The mechanism of fibrosis with potential grip points for juglanin activity. Abbreviations: collagen type I alpha 1 (COL1A1); collagen type I alpha 2 (COL1A2); connective tissue growth factor (CTGF); chemokine C-X-C motif ligand 1 (CXCL1); extracellular matrix (ECM); fibronectin 1 (FN1); interleukin 17 (IL-17); interleukin 18 (IL-18); interleukin 1β (IL-1β); interleukin 6 (IL-6); mitogen activated protein kinase (MAPK); matrix metalloproteinase 9 (MMP-9); nuclear factor-κB (NF-κB); stimulator of interferon genes (STING); transforming growth factor β1 (TGF-β1); tissue inhibitor of metalloproteinase 1 (TIMP-1); toll-like receptor 4 (TLR4); tumor necrosis factor-α (TNF-α); α-smooth muscle actin (α-SMA).</p>
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<p>The effects of juglanin on metabolic syndrome. Abbreviations: acetyl-CoA carboxylase α (ACCα); AMP-activated protein kinase (AMPK); carnitine-palmitoyl transferase 1α (CPT-1); CCAAT-enhancer-binding protein α/β (C/EBP α/β); fatty acid synthase (FAS); fatty acid-binding protein 4 (FABP4); glucose transporter 4 (GLUT4); high-density lipoprotein (HDL); nuclear factor-κB (NF-κB); peroxisome proliferator-activated receptor α (PPAR-α); peroxisome proliferator-activated receptor γ (PPAR-γ); sirtuin 1 (SIRT1); stearoyl-CoA desaturase 1 (SCD1); sterol regulatory-element binding proteins 1c (SREBP-1c); triglycerides (TG); tumor necrosis factor-α (TNF-α); uncoupling protein 2 (UCP-2). ↑ increase; ↓ decrease; − not changed.</p>
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<p>The potential mechanisms of juglanin hepatoprotective activity. Abbreviations: B-cell lymphoma-extra large (Bcl-xL); bcl-2-like protein 4 (Bax); catalase (CAT); glutamate-cysteine ligase subunits (GCLC, GCLM); glutathione peroxides (GPx); interferon β (IFN-β); interleukin 1β (IL-1β); interleukin 6 (IL-6); mitogen-activated protein kinase (MAPK); NAD(P)H quinone dehydrogenase 1 (NQO-1); nuclear factor erythroid 2-related factor 2 (Nrf2); oxygenase 1 (HO-1); phosphorylated signal transducer and activator of transcription (p-STAT); phosphorylated c-Jun N-terminal kinase (p-JNK); phosphorylated extracellular signal-regulated kinase (p-ERK); phosphorylated inhibitor κB-α (p-IκBα); phosphorylated IκB kinase α (p-IKKα); phosphorylated Janus Kinase 2 gene (p-JAK2); phosphorylated nuclear factor-κB (p-NF-κB); phosphorylated TANK-binding kinase 1 (p-TBK1); toll-like receptor 4 (TLR4); reactive oxygen species (ROS); superoxide dismutase (SOD); suppressor of IKKepsilon (SIKE); tumor necrosis factor-α (TNF-α).</p>
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<p>The potential mechanisms of juglanin activity in the cardiovascular system. Abbreviations: AMP-activated protein kinase (AMPK); endothelial nitric oxide synthase (eNOS); high mobility group box 1 (HMGB1); interleukin 1β (IL-1β); interleukin 6 (IL-6); kruppel-like factor 2 (KLF-2); mitogen-activated protein kinase (MAPK); monocyte chemoattractant protein 1 (MCP-1); NADPH oxidase 2 (NOX-2); nitrogen oxide (NO); nuclear factor erythroid 2-related factor 2 (Nrf2); nuclear factor-κB (NF-κB); oxygenase 1 (HO-1); phosphorylated c-Jun N-terminal kinase (p-JNK); phosphorylated extracellular signal-regulated kinase (p-ERK); reactive oxygen species (ROS); receptor for advanced glycation end products (RAGE); superoxide dismutase (SOD); toll-like receptor 4 (TLR4); tryptophan hydroxylase-1 (TPH-1); tumor necrosis factor-α (TNF-α); vascular cellular adhesion molecule-1 (VCAM-1); vascular endothelial growth factor (VEGF); vascular endothelial growth factor receptor 2 (VEGFR2); zonula occludens-1 (ZO-1).</p>
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<p>The potential pathways of juglanin activity in the central nervous system. Abbreviations: AMP-activated protein kinase (AMPK); B-cell lymphoma 2 (Bcl-2); Bcl-2-like protein 4 (Bax); beta-amyloid (Aβ); cluster of differentiation 11b (CD11b); cluster of differentiation 14 (CD14); cyclooxygenase 2 (COX-2); enhanced neurotrophic factor (BDNF); glial fibrillary acidic protein (GFAP); inducible nitric oxide synthase (iNOS); interleukin 18 (IL-18); interleukin 1β (IL-1β); interleukin 6 (IL-6); ionized calcium-binding adaptor molecule 1 (Iba1); monocyte chemoattractant protein 1 (MCP-1); myeloid differentiation primary response 88 (MyD88); nuclear factor-κB (NF-κB); phosphoinositide 3-kinase (PI3K); phosphorylated inhibitor κB-α (p-IκBα); phosphorylated IκB kinase α (p-IKKα); phosphorylated microtubule-associated protein (p-Tau); poly-ADP-ribose polymerase (PARP); protein kinase B (AKT); toll-like receptor 4 (TLR4); tumor necrosis factor-α (TNF-α).</p>
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<p>The potential pathways of juglanin activity in the skeletal system. Abbreviations: apoptosis-associated Speck-like protein containing a caspase activation and recruitment domain (ASC); cysteine cathepsin K (CTSK); disintegrin and metalloproteinase with thrombospondin motifs (ADAMTS); factor matrix metalloproteinase (MMP); factor matrix metalloproteinase 9 (MMP-9); glutathione (GSH); interleukin 1 (IL-1); interleukin 1β (IL-1β); interleukin 6 (IL-6); malondialdehyde (MDA); NADPH oxidase 4 (NOX-4); nitrogen oxide (NO); nucleotide-binding domain, leucine-rich–containing family, pyrin domain–containing-3 (NLRP3); nuclear factor-κB (NF-κB); phosphorylated inhibitor κB-α (p-IκBα); phosphorylated IκB kinase (p-IKK); prostaglandin E2 (PGE2); reactive oxygen species (ROS); receptor activator for nuclear factor κ B (RANK); receptor activator for nuclear factor κ B ligand (RANKL); sirtuin 1 (SIRT1); superoxide dismutase (SOD); thioredoxin-interacting protein (TxNIP); transcription factor nuclear factor of activated T cells c1 (NFATc1); Fos proto-oncogene (c-Fos); transforming growth factor β (TGF-β); translating ribosome affinity purification (TRAP); tumor necrosis factor receptor-associated factor 6 (TRAF6); tumor necrosis factor-α (TNF-α).</p>
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<p>The potential metabolic pathways of juglanin anti-cancer activity. Abbreviations: ataxia telangiectasia mutated (ATM); autophagy protein 7, 3 (ATG-7, ATG-3); B-cell lymphoma 2 (Bcl-2); B-cell lymphoma-extra large (Bcl-xL); bcl-2-like protein 4 (Bax); BH3 domain-containing protein (Bad); cyclin-dependent kinase 1 (CDK1); death receptor 4 (DR4); death receptor 5 (DR5); FAS-associated death domain protein (FADD); gap 2 phase/mitosis phase in the cell cycle (G2/M); interleukin 18 (IL-18); interleukin 1β (IL-1β); microtubule-associated protein light chain 3 (LC3); nuclear factor-κB (NF-κB); phosphatidylinositol 3-kinase catalytic subunit type 3 (PIK3C3); phosphoinositide 3-kinase (PI3K); phosphorylated cell division cycle 2 (p-Cdc2); phosphorylated cell division cycle 25C (p-Cdc25C); phosphorylated checkpoint kinase 2 (p-Chk2); phosphorylated c-Jun N-terminal kinase (p-JNK); phosphorylated extracellular signal-regulated kinase 1/2 (p-ERK 1/2); phosphorylated inhibitor κB-α (p-IκBα); phosphorylated mammalian target of rapamycin (p-mTOR); poly-ADP-ribose polymerase (PARP); protein kinase B (AKT); reactive oxygen species (ROS); TNF-related apoptosis-inducing ligand (TRAIL); tumor necrosis factor-α (TNF-α).</p>
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<p>Summary of the potential pathways of juglanin’s biological activity. Abbreviations: AMP-activated protein kinase (AMPK); high mobility group box 1 (HMGB1); Janus kinase gene/signal transducer and activator of transcription (JAK/STAT); Kruppel-like factor 2 (KLF-2); mitogen-activated protein kinase (MAPK); nuclear factor erythroid 2-related factor 2 (Nrf2); nuclear factor-κB (NF-κB); nucleotide-binding domain, leucine-rich-containing family, pyrin domain-containing-3 (NLRP3); phosphoinositide 3-kinase/protein kinase B (PI3K/AKT); sirtuin 1 (SIRT1); stimulator of interferon genes (STING); toll-like receptor 4 (TLR4); transforming growth factor β1 (TGF- β1).</p>
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18 pages, 7282 KiB  
Article
Delineating Molecular Regulatory of Flavonoids Indicated by Transcriptomic and Metabolomics Analysis during Flower Development in Chrysanthemum morifolium ‘Boju’
by Zhuannan Chu, Rui Xiong, Xingxing Peng, Guangsheng Cui, Ling Dong and Weiwen Li
Int. J. Mol. Sci. 2024, 25(19), 10261; https://doi.org/10.3390/ijms251910261 - 24 Sep 2024
Viewed by 598
Abstract
Flavonoids are pharmacologically active compounds in flowers of Chrysanthemum morifoliumBoju’ (C. morifolium); however, the molecular regulatory network governing flower development remains largely elusive. Flower samples were collected at four stages, namely budding (BD), bud breaking (BB), early blooming (EB), [...] Read more.
Flavonoids are pharmacologically active compounds in flowers of Chrysanthemum morifoliumBoju’ (C. morifolium); however, the molecular regulatory network governing flower development remains largely elusive. Flower samples were collected at four stages, namely budding (BD), bud breaking (BB), early blooming (EB), and full blooming (FB), for omics analysis. We revealed distinct transcriptional regulation patterns at these four stages of the flower from the perspective of differentially expressed unigenes (DEGs). There are 152 DEGs shared among the three comparative groups (BD vs. BB, BB vs EB, EB vs FB), wherein the expression of 44 DEGs (including AtADT6, MDL3, and ROMT) continues to be upregulated, and 85 DEGs (including CYP81E, TPS-Cin-1, and TPS-Cin-2) showed persistent downregulation with flower development. Flavonoid-targeted metabolomics identified 118 differentially abundant metabolites (DAMs) in the FB group compared to the BD stage; the top three upregulated and downregulated metabolites are Cyanidin-3-O-(6″-O-malonyl)glucoside-5-O-glucoside, Luteolin-7-O-(6″-caffeoyl)rhamnoside, Kaempferol-3-O-(6″-p-coumaroyl)glucoside and Chrysoeriol-6,8-di-C-glucoside-7-O-glucoside, Kaempferol, Kaempferol-3,7-O-dirhamnoside, respectively. These DAMs were predominantly enriched in “flavonoid biosynthesis”, “isoflavonoid biosynthesis”, and “flavone and flavonol biosynthesis” pathways. AtADT6, MDL3, ROMT, CYP81E, TPS-Cin-1, and TPS-Cin-2 were correlated with kaempferol. Our findings provide a new idea for interfering with flavonoid production, especially kaempferol, in flowers. Full article
(This article belongs to the Section Bioactives and Nutraceuticals)
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<p>Transcriptomic profiles of four developmental stages of C. <span class="html-italic">morifolium</span> flower. (<b>A</b>) Representative images of C. <span class="html-italic">morifolium</span> flowers at four different stages of development. (<b>B</b>) Statistical pie charts of transcript sequences mapped to different species in the NR database. (<b>C</b>) Principal component analysis plot of all samples in the transcriptome. B1, B2, B3, and B4 means BD, BB, EB, and FB, respectively.</p>
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<p>Flowers of C. <span class="html-italic">morifolium</span> exhibit differential transcriptomic profiles at four different stages. Volcano map of differentially expressed unigenes in the comparison groups of BD vs. BB (<b>A</b>), BB vs. EB (<b>B</b>), BB vs. FB (<b>C</b>). Red indicates up-regulated genes, green indicates down-regulated genes, and blue indicates non-significant genes. (<b>D</b>) The hierarchical clustering heatmap of all differentially expressed unigenes. Bubble plot of KEGG enrichment of differentially expressed unigenes in the comparison groups of BD vs. BB (<b>E</b>), BB vs. EB (<b>F</b>), BB vs. FB (<b>G</b>).</p>
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<p>Identification of common differentially expressed unigenes in all the comparison groups. (<b>A</b>) A Venn diagram of intersected differentially expressed unigenes from the three comparative groups. (<b>B</b>) Kmeans_clustering analysis of differentially expressed unigenes in four groups. (<b>C</b>) Bubble plot of KEGG enrichment of 44 common upregulated differentially expressed unigenes. (<b>D</b>) Bubble plot of KEGG enrichment of 85 common downregulated differentially expressed unigenes.</p>
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<p>The metabolic landscape of flavonoid compounds in the flowers undergoes significant changes, particularly in the early and mature stages. (<b>A</b>) Scores of OPLS-DA plot and OPLS-DA model in the comparison groups of BD vs. FB. M1, M2, M3, and M4 means BD, BB, EB, and FB, respectively. (<b>B</b>) The hierarchical clustering heatmap of differentially abundance metabolites between BD vs. FB. (<b>C</b>) Histogram of the top 20 differentially abundance metabolites between BD vs. FB. (<b>D</b>) Histogram of KEGG enrichment pathway of differentially abundance metabolites between BD vs. FB.</p>
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<p>Four candidate metabolites from metabolome data were verified by LC-MS detection. ns means <span class="html-italic">p</span> &gt; 0.05, * means <span class="html-italic">p</span> &lt; 0.05.</p>
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<p>Integrative analyses of transcriptome and metabolome reveal the molecular mechanism underlying variation in flavonoids during flower development of <span class="html-italic">C</span>. <span class="html-italic">morifolium</span>. (<b>A</b>) A nine-quadrant volcano plot of Pearson correlation coefficients between genes and metabolites. (<b>B</b>) Genes and metabolites exhibiting a consistent regulatory trend were visualized in a hierarchical clustering heatmap. (<b>C</b>) The canonical correlation analysis (CCA) plot in flavonoid biosynthesis pathway. (<b>D</b>) The CCA plot in flavone and flavonol biosynthesis pathway.</p>
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<p>KEGG map of flavone and flavonol biosynthesis. Red and green circles indicate differentially abundance metabolites that are up-regulated and down-regulated in BD vs. FB, respectively. The blue boxes indicate genes that are up-regulated or down-regulated.</p>
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17 pages, 5128 KiB  
Article
Solid-State Fermentation-Assisted Extraction of Flavonoids from Grape Pomace Using Co-Cultures
by Arturo Siller-Sánchez, Cristóbal N. Aguilar, Mónica L. Chávez-González, Juan A. Ascacio-Valdés, Deepak Kumar Verma and Miguel Aguilar-González
Processes 2024, 12(9), 2027; https://doi.org/10.3390/pr12092027 - 20 Sep 2024
Viewed by 1370
Abstract
Eighty percent of grape production is destined for the wine industry, which generates various types of waste, of which grape pomace is the main one, accounting for 50–60% of waste created during processing. This waste could be a promising source of bioactive compounds [...] Read more.
Eighty percent of grape production is destined for the wine industry, which generates various types of waste, of which grape pomace is the main one, accounting for 50–60% of waste created during processing. This waste could be a promising source of bioactive compounds (e.g., flavonoids and tannin), which are known for their antioxidant properties. Although these byproducts pose disposal challenges, they can be utilized as a substrate for solid-state fermentation bioprocess using co-cultures, where different microorganisms can interact and complement each other, improving the efficiency of metabolite production or substrate degradation. This study investigates the extraction of phenolic compounds and the antioxidant activity of the compounds from grape pomace in the solid-state fermentation bioprocess, comparing fungal and yeast monocultures, and then exploring the use of two co-cultures (P. stipites/A. niger GH1 and S. cerevisiae/A. niger) on the flavonoid extractive process. Fermentation kinetics were evaluated over 120 h, with sampling done every 12 h. Initially, yeasts were used to reduce the content of simple sugars in the medium, and fungus was added at 24 h into the process due to its ability to produce a broad spectrum of extracellular enzymes, allowing a higher efficiency in substrate degradation. Competition or antagonism during co-culture leads to significantly higher production of compounds, which are recovered using different solvents. The evaluation included phenolic compounds (total polyphenols, condensed tannins, and total flavonoids), antioxidant activity (DPPH●/FRAP), molecular characterization (HPLC-MS), and structural microscopy during the bioprocess. The highest titers obtained were 62.46 g/L for total flavonoids and 32.04 g/L for condensed tannins, using acetone as the solvent in co-culture with P. stipitis after 120 h of fermentation. Characterization identified 38 compounds, highlighting families of flavonols, hydroxybenzoic acids, and hydroxycinnamic acids. The co-culture of P. stipitis and A. niger GH1 significantly improved the extraction yield of bioactive compounds through solid-state fermentation. Full article
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<p>Microscopy images throughout the fermentation kinetics with <span class="html-italic">A. niger</span> GH1. (<b>a</b>) 0 h, (<b>b</b>) 60 h, (<b>c</b>) 120 h.</p>
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<p>Fermentation kinetics for total flavonoids, hydrolyzable tannins, condensed tannins, and FRAP and DPPH activity with <span class="html-italic">A. niger</span> GH1. (<b>a</b>) Bioactive compounds using ethanol as a solvent. (<b>b</b>) Antioxidant potential using ethanol as a solvent. (<b>c</b>) Bioactive compounds using acetone as a solvent. (<b>d</b>) Antioxidant potential using acetone as a solvent.</p>
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<p>Total sugar content throughout the fermentation kinetics of grape pomace with yeast.</p>
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<p>Fermentation kinetics for total flavonoids, hydrolyzable tannins, condensed tannins, FRAP activity, and DPPH activity with co-culture. (<b>a</b>) Co-culture <span class="html-italic">S. cerevisae</span>-<span class="html-italic">A. niger</span> solvent for extraction ethanol. (<b>b</b>) Co-culture <span class="html-italic">P. stipitis</span>-<span class="html-italic">A. niger</span> solvent for extraction ethanol. (<b>c</b>) Co-culture <span class="html-italic">S. cerevisae</span>-<span class="html-italic">A. niger</span> solvent for extraction ethanol. (<b>d</b>) Co-culture <span class="html-italic">P. stipitis</span>-<span class="html-italic">A. niger</span> solvent for extraction ethanol. (<b>e</b>) Co-culture <span class="html-italic">S. cerevisae</span>-<span class="html-italic">A. niger</span> solvent for extraction acetone. (<b>f</b>) Co-culture <span class="html-italic">P. stipitis</span>-<span class="html-italic">A. niger</span> solvent for extraction acetone. (<b>g</b>) Co-culture <span class="html-italic">S. cerevisae</span>-<span class="html-italic">A. niger</span> solvent for extraction acetone. (<b>h</b>) Co-culture <span class="html-italic">P. stipitis</span>-<span class="html-italic">A. niger</span> solvent for extraction acetone.</p>
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<p>Fermentation kinetics for total flavonoids, hydrolyzable tannins, condensed tannins, FRAP activity, and DPPH activity with co-culture. (<b>a</b>) Co-culture <span class="html-italic">S. cerevisae</span>-<span class="html-italic">A. niger</span> solvent for extraction ethanol. (<b>b</b>) Co-culture <span class="html-italic">P. stipitis</span>-<span class="html-italic">A. niger</span> solvent for extraction ethanol. (<b>c</b>) Co-culture <span class="html-italic">S. cerevisae</span>-<span class="html-italic">A. niger</span> solvent for extraction ethanol. (<b>d</b>) Co-culture <span class="html-italic">P. stipitis</span>-<span class="html-italic">A. niger</span> solvent for extraction ethanol. (<b>e</b>) Co-culture <span class="html-italic">S. cerevisae</span>-<span class="html-italic">A. niger</span> solvent for extraction acetone. (<b>f</b>) Co-culture <span class="html-italic">P. stipitis</span>-<span class="html-italic">A. niger</span> solvent for extraction acetone. (<b>g</b>) Co-culture <span class="html-italic">S. cerevisae</span>-<span class="html-italic">A. niger</span> solvent for extraction acetone. (<b>h</b>) Co-culture <span class="html-italic">P. stipitis</span>-<span class="html-italic">A. niger</span> solvent for extraction acetone.</p>
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<p>Microscopy images throughout the fermentation kinetics of the <span class="html-italic">Aspergillus-Pichia</span> co-culture. (<b>a</b>) 0 h, (<b>b</b>) 24 h, (<b>c</b>) 72 h.</p>
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31 pages, 4064 KiB  
Article
Genus Ribes: Ribes aureum, Ribes pauciflorum, Ribes triste, and Ribes dikuscha—Comparative Mass Spectrometric Study of Polyphenolic Composition and Other Bioactive Constituents
by Mayya P. Razgonova, Muhammad Amjad Nawaz, Andrey S. Sabitov and Kirill S. Golokhvast
Int. J. Mol. Sci. 2024, 25(18), 10085; https://doi.org/10.3390/ijms251810085 - 19 Sep 2024
Viewed by 493
Abstract
This study presents the metabolomic profiles of the four Ribes species (Ribes pauciflorum Turcz., Ribes triste Pall., Ribes dicuscha Fisch., and Ribes aureum Purch.). The plant material was collected during two expeditions in the Russian Far East. Tandem mass spectrometry was used [...] Read more.
This study presents the metabolomic profiles of the four Ribes species (Ribes pauciflorum Turcz., Ribes triste Pall., Ribes dicuscha Fisch., and Ribes aureum Purch.). The plant material was collected during two expeditions in the Russian Far East. Tandem mass spectrometry was used to detect target analytes. A total of 205 bioactive compounds (155 compounds from polyphenol group and 50 compounds from other chemical groups) were tentatively identified from the berries and extracts of the four Ribes species. For the first time, 29 chemical constituents from the polyphenol group were tentatively identified in the genus Ribes. The newly identified polyphenols include flavones, flavonols, flavan-3-ols, lignans, coumarins, stilbenes, and others. The other newly detected compounds in Ribes species are the naphthoquinone group (1,8-dihydroxy-anthraquinone, 1,3,6,8-tetrahydroxy-9(10H)-anthracenone, 8,8′-dihydroxy-2,2′-binaphthalene-1,1′,4,4′-tetrone, etc.), polyhydroxycarboxylic acids, omega-3 fatty acids (stearidonic acid, linolenic acid), and others. Our results imply that Ribes species are rich in polyphenols, especially flavanols, anthocyanins, flavones, and flavan-3-ols. These results indicate the utility of Ribes species for the health and pharmaceutical industry. Full article
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<p>Global metabolome profile of <span class="html-italic">Ribes</span> species. (<b>A</b>) No. of compounds detected in each compound class in all species. (<b>B</b>) No. of compounds detected in each <span class="html-italic">Ribes</span> species. The circle size indicates the number of compounds. (<b>B</b>) was prepared in TBtools [<a href="#B21-ijms-25-10085" class="html-bibr">21</a>].</p>
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<p>(<b>A</b>) CID spectrum of formononetin from <span class="html-italic">R. aureum</span>, <span class="html-italic">m</span>/<span class="html-italic">z</span> 269.18. The chemical structures correspond to panel A of the figure. The formulas were obtained from the PubChem database of the National Library of Medicine, National Center for Biotechnology Information. (<b>B</b>) CID spectrum of acacetin from <span class="html-italic">R. triste</span>, <span class="html-italic">m</span>/<span class="html-italic">z</span> 285.31. (<b>C</b>) CID spectrum of isovitexin from extract of <span class="html-italic">R. aureum</span>, <span class="html-italic">m</span>/<span class="html-italic">z</span> 431.42. (<b>D</b>) CID spectrum of kaempferol from extract of <span class="html-italic">R. pauciflorum</span>, <span class="html-italic">m</span>/<span class="html-italic">z</span> 287.12.</p>
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<p>(<b>A</b>) CID spectrum of quercetin from extract of <span class="html-italic">R. triste</span>, <span class="html-italic">m</span>/<span class="html-italic">z</span> 303.17. (<b>B</b>) CID spectrum of gallocatechin from extracts of <span class="html-italic">R. triste</span>, <span class="html-italic">m</span>/<span class="html-italic">z</span> 307.12. (<b>C</b>) CID spectrum of anthocyanin delphinidin 3,5-dihexoside from berries of <span class="html-italic">R. dikuscha</span>, <span class="html-italic">m</span>/<span class="html-italic">z</span> 626.69. (<b>D</b>) CID spectrum of anthocyanin petunidin-3-<span class="html-italic">O</span>-glucoside from berries of <span class="html-italic">R. dikuscha</span>, <span class="html-italic">m</span>/<span class="html-italic">z</span> 479.16.</p>
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<p>(<b>A</b>) Venn diagram showing similarities and differences in the presence of the polyphenol group, (<b>B</b>) anthocyanins, and (<b>C</b>) flavones and flavonols in <span class="html-italic">Ribes</span> species. Bi-iv panels (x-axis) indicate the type of anthocyanins detected in each <span class="html-italic">Ribes</span> species.</p>
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<p>Plant samples used in this study. (<b>A</b>) <span class="html-italic">Ribes dicuscha</span> (the vicinity of the Kolyma River, N = 59°4141′960 E = 151°16′17.620). (<b>B</b>) <span class="html-italic">Ribes pauciflorum</span>, (<b>C</b>) <span class="html-italic">Ribes triste</span>, (<b>D</b>) <span class="html-italic">Ribes aureum</span> (Seymchansky District, the vicinity of the Kolyma River, N = 62°55′51.017 E = 151°16′17.620. (<b>E</b>) Map of the route and collection of plant material in the Magadan region, Russian Federation (N 58–61°, E 150–153°).</p>
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19 pages, 920 KiB  
Article
Pelargonium graveolens: Towards In-Depth Metabolite Profiling, Antioxidant and Enzyme-Inhibitory Potential
by Reneta Gevrenova, Gokhan Zengin, Vessela Balabanova, Anna Szakiel and Dimitrina Zheleva-Dimitrova
Plants 2024, 13(18), 2612; https://doi.org/10.3390/plants13182612 - 19 Sep 2024
Viewed by 557
Abstract
Pelargonium graveolens L’Hèr. (Geraniaceae) is renowned for its traditional use as a flavor, ornamental and medicinal plant. This work aimed at an in-depth study of the phytochemical profiling and in vitro antioxidant and enzyme inhibition assessment of a methanol-aqueous extract from P. graveolens [...] Read more.
Pelargonium graveolens L’Hèr. (Geraniaceae) is renowned for its traditional use as a flavor, ornamental and medicinal plant. This work aimed at an in-depth study of the phytochemical profiling and in vitro antioxidant and enzyme inhibition assessment of a methanol-aqueous extract from P. graveolens leaves. A UHPLC-HRMS analysis revealed more than 110 secondary metabolites, including 8 acyltartaric and 11 acylcitric/acylisocitric acids; 8 gallotannins; 36 flavonols, flavanones and methoxylated flavonoids together with 17 phenolic and aliphatic acids; and 21 phenolic acid glycosides. For the first time, acylcitric acids along with feruloyl- and coumaroyltartaric acids are reported in the species. The leaf extract actively scavenged 2,2-diphenyl-1-picrylhydrazyl DPPH (273.45 mg trolox equivalent (TE/g)) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) radicals (531.97 mgTE/g) and showed a high reducing power: 431.32 mg TE/g Cupric reducing antioxidant capacity (CUPRAC) and 292.21 mg TE/g Ferric reducing antioxidant power (FRAP). It possessed a metal chelating capacity (13.44 ethylenediaminetetraacetic acid equivalent (EDTAE)/g) and contained 2.71 mmol TE/g in the phosphomolybdenum assay. The rose geranium extract exhibited high inhibition towards acetyl- and butyrylcholinesterase (2.80 and 2.20 mg galantamine equivalent (GALAE)/g, respectively) and tyrosinase (75.49 mg kojic acid equivalent (KAE)/g). It inhibited α-glucosidase and α-amylase (3.75 mmol and 0.79 acarbose equivalent (ACAE)/g, respectively) and lipase (28.91 mg orlistat equivalent (OE)/g). This study sheds light into the future potential application of the rose geranium in pharmaceutical and nutraceutical products. Full article
(This article belongs to the Section Phytochemistry)
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<p>The workflow for the essential aspects in qualitative plant metabolite profiling, including critical review of previous literature (<b>I</b>); cultivated material documented by vouchers in public herbaria (<b>II</b>); gentle extraction procedure avoiding artefacts (<b>III</b>); state-of-the-art chemical analysis (<b>IV</b>); careful chemical data interpretation to obtain extracted ion chromatograms (<b>V</b>); analyzing MS/MS fragmentation pathway of each compound (<b>VI</b>); parallel comparison of tR, exact high-resolution mass and MS/MS spectra with reference standards (<b>VII</b>) or comparison with previous scientific knowledge (<b>VIII</b>); and metabolite identification assigning reliable confidence levels (<b>IX</b>).</p>
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<p>MS/MS spectra of feruloyltartaric acid (<b>57</b>) (<b>A</b>), coumaroylcitric/coumaroylisocitric acid (<b>63</b>) (<b>B</b>), tetragalloyl hexoside (<b>75</b>) (<b>C</b>) and kaempferol dimethyl ether (<b>111</b>) (<b>D</b>).</p>
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