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Flavones and flavonols are important classes of flavonoids with nutraceutical and pharmacological value, and their production by fermentation with recombinant microorganisms promises to be a scalable and economically favorable alternative to extraction from plant sources. Flavones and flavonols have been produced recombinantly in a number of microorganisms, with Saccharomyces cerevisiae typically being a preferred production host for these compounds due to higher yields and titers of precursor compounds, as well as generally improved ability to functionally express cytochrome P450 enzymes without requiring modification to improve their solubility. Recently, a rapid prototyping platform has been developed for high-value compounds in E. coli, and a number of gatekeeper (2S)-flavanones, from which flavones and flavonols can be derived, have been produced to high titers in E. coli using this platform. In this study, we extended these metabolic pathways using the previously reported platform to produce apigenin, chrysin, luteolin and kaempferol from the gatekeeper flavonoids naringenin, pinocembrin and eriodictyol by the expression of either type-I flavone synthases (FNS-I) or type-II flavone synthases (FNS-II) for flavone biosynthesis, and by the expression of flavanone 3-dioxygenases (F3H) and flavonol synthases (FLS) for the production of the flavonol kaempferol. In our best-performing strains, titers of apigenin and kaempferol reached 128 mg L−1 and 151 mg L−1 in 96-DeepWell plates in cultures supplemented with an additional 3 mM tyrosine, though titers for chrysin (6.8 mg L−1) from phenylalanine, and luteolin (5.0 mg L−1) from caffeic acid were considerably lower. In strains with upregulated tyrosine production, apigenin and kaempferol titers reached 80.2 mg L−1 and 42.4 mg L−1 respectively, without the further supplementation of tyrosine beyond the amount present in the rich medium. Notably, the highest apigenin, chrysin and luteolin titers were achieved with FNS-II enzymes, suggesting that cytochrome P450s can show competitive performance compared with non-cytochrome P450 enzymes in prokaryotes for the production of flavones.

Anthocyanins are responsible for the color spectrum of both ornamental and natural flowers. However, not all plant species produce all colors. For example, roses are not blue because they do not naturally possess a hydroxylase that opens the pathway for delphinidin and its derivatives. It is more intriguing why some plants do not carry orange or scarlet red flowers with anthocyanins based on pelargonidin, because the precursor for these anthocyanins should be available if anthocyanins are made at all. The key to this is the substrate specificity of dihydroflavonol 4-reductase (DFR), an enzyme located at the branch point between flavonols and anthocyanins. The most common example is petunia, which does not bear orange flowers unless the enzyme is complemented by biotechnology. We changed a few amino acids in the active site of the enzyme and showed that the mutated petunia DFR started to favor dihydrokaempferol, the precursor to orange pelargonidin, in vitro. When transferred to petunia, it produced an orange hue and dramatically more pelargonidin-based anthocyanins in the flowers. [ABSTRACT FROM AUTHOR]

Allium (A.) species are one of the most widespread plants in the world, which have played a special role in terms of nutrition, treatment, and economy since long ago. This study is the first report on the phytochemical and biological activities of A. colchicifolium. Five flavonoids, including isorhamnetin (compound 1), quercetin (compound 2), morin (compound 3), isorhamnetin-3-O-glucoside (compound 4), and quercetin 3-O-glucoside (compound 5), were isolated and purified for the first time from A. colchicifolium leaves. All isolated flavonoids showed antibacterial and antibiofilm activities. Compound 3 revealed prominent antibacterial activities against Staphylococcus (S.) aureus and Proteus (P.) mirabilis. Also, compounds 3 and 5 showed the highest antibiofilm activities on S. aureus and P. mirabilis, respectively. The docking study results showed that compounds 3, 4, and 5 had the most robust interactions with two critical proteins in biofilm formation, including staphylococcal accessory regulator A (SarA) and mannose-resistant Proteus-like fimbriae H (MrpH). Besides, compounds 2 and 3 revealed significant antioxidant activities in 2, 2-diphenyl-1-picrylhydrazyl (DPPH) and ferric (Fe3+)-reducing antioxidant power (FRAP) tests compared to the other compounds and positive controls. Also, the ADMET (absorption, distribution, metabolism, excretion, and toxicity) prediction assay showed that compounds 1, 2, and 3 have suitable physicochemical and pharmacokinetic properties. The results of this study confirm that the flavonoids isolated from the leaves of A. colchicifolium can be promising candidates for use in the pharmaceutical and food industries. [ABSTRACT FROM AUTHOR]

Crocus sativus L. is largely cultivated because it is the source of saffron, a well-appreciated and valued spice, not only for its culinary use but also because of its significant biological activities. Stigmas are the main product obtained from flowers, but in addition, tepals, largely considered a waste product, represent a big source of flavonoids and anthocyanins. This study aimed to delve into the phytochemical composition of saffron tepals and investigate whether the composition was influenced by the extraction technique while investigating the main analytical techniques most suitable for the characterization of tepal extracts. The research focuses on flavonoids, a class of secondary metabolites, and their health benefits, including antioxidant, anti-inflammatory, and anticancer properties. Flavonoids occur as aglycones and glycosides and are classified into various classes, such as flavones, flavonols, and flavanones. The most abundant flavonoids in tepals are kaempferol glycosides, followed by quercetin and isorhamnetin glycosides. Overall, this review provides valuable insights into the potential uses of tepals as a source of bioactive compounds and their applications in various fields, promoting a circular and sustainable economy in saffron cultivation and processing. [ABSTRACT FROM AUTHOR]

Plants in high-altitude habitats are exposed to severe environmental stressors, including extreme temperatures and irradiation, which can have wide-ranging effects on changes of secondary-metabolite profiles in higher plants. Altitude-related variation of levels of polyphenols in organs of medicinal and food plant species has not yet been investigated sufficiently. This study was focused on variation in quantitative profiles of classes and of individual biologically active phenolic compounds in leaf extracts of resource species Spiraea chamaedryfolia and Spiraea media from the family Rosaceae in coenopopulations of the Altai Mountains, along an altitudinal gradient. High-performance liquid chromatography revealed 22 polyphenolic compounds in the extracts of S. media leaves, with the main polyphenolic compounds being flavonols. Sixteen compounds were found in S. chamaedryfolia leaf extracts, and the major ones were flavonols and a flavanone. Opposite responses to changes in the altitude-associated growth conditions were documented for levels of some individual polyphenolic compounds. With an increase in altitude, concentrations of chlorogenic acid and of flavanone in the extracts of S. chamaedryfolia leaves significantly increased, while concentrations of cinnamic acid, astragalin, and kaempferol diminished. A statistically significant positive correlation between the altitude of plant habitats and total levels of polyphenols and phenolcarboxylic acids was detected. In leaf extracts from S. media, an altitude increase was significantly positively correlated with astragalin, avicularin, and cinnamic acid levels and negatively correlated with hyperoside concentration. [ABSTRACT FROM AUTHOR]

The study of Aronia melanocarpa's (A. melanocarpa) biological activity is focused on obtaining the crude extract and separation of the flavonol compounds. The extraction and fractionation of A. melanocarpa fruits, followed by quantitative analysis, were accomplished using high-performance liquid chromatography and Darco G-60 filtering. This approach enabled the quantification of flavonoids within each fraction. The antioxidative, immunomodulating activities and cytotoxicity with respect to the lymphoblast cell line RPMI-1788 were studied. The flavonol extract of A. melanocarpa has been shown to have a high capacity to neutralize free DPPH and AAPH radicals in vitro. It also caused an accelerated 'respiratory burst' formation of neutrophils and an increase in the metabolic reserves of cells in rats exposed to cyclophosphamide. The reference solution (an equivalent quercetin-rutin blend) contributed to a decrease in lipid peroxidation, intensifying phagocytosis processes. The studied compounds demonstrated their low influence on the leukocyte blood profile in animals. [ABSTRACT FROM AUTHOR]

Studies of polyphenols in various natural products have shown their variability and often low amounts. Thus, we aimed to investigate the bioaccessibility of the main polyphenolic groups extracted from two poplar types of propolis collected in continental Croatia. The propolis complex, in the form of water-soluble powder of propolis extract with the carrier 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), was obtained by applying ultrasonic-assisted extraction followed by lyophilization. The in vitro gastrointestinal digestion was conducted on the propolis complex extracts and a mixture of standards (pinocembrin, galangin, chrysin, caffeic acid, and caffeic acid phenylethyl ester). Fractions from the oral, gastric, and intestinal phase samples were analyzed spectrophotometrically by standard methods used to determine the content of total phenols (TPs), flavonols/flavones (TFFs), and flavanones/dihydroflavonols (TFDs). The small-intestinal phase was performed by two models: centrifugation and dialysis. The results of propolis-HP-β-CD extracts demonstrated high polyphenolic bioaccessibility during all three phases of digestion. The bioaccessibility of TPs, TFFs, and TFDs after the intestinal phase with centrifugation was from 0.02 to 8.86 times higher than in the dialysis phase, stressing that it is a better model than dialysis. Our findings show that the inclusion complex of propolis with HP-β-CD enables the good solubility of polyphenol groups. [ABSTRACT FROM AUTHOR]

Tea, an extensively consumed and globally popular beverage, has diverse chemical compositions that ascertain its quality and categorization. In this investigation, we formulated an analytical and quantification approach employing reversed-phase ultra-high-performance liquid chromatography (UHPLC) methodology coupled with diode-array detection (DAD) to precisely quantify 20 principal constituents within 121 tea samples spanning 6 distinct variants. The constituents include alkaloids, catechins, flavonols, and phenolic acids. Our findings delineate that the variances in chemical constitution across dissimilar tea types predominantly hinge upon the intricacies of their processing protocols. Notably, green and yellow teas evinced elevated concentrations of total chemical moieties vis à vis other tea classifications. Remarkably divergent levels of alkaloids, catechins, flavonols, and phenolic acids were ascertained among the disparate tea classifications. By leveraging random forest analysis, we ascertained gallocatechin, epigallocatechin gallate, and epicatechin gallate as pivotal biomarkers for effective tea classification within the principal cadre of tea catechins. Our outcomes distinctly underscore substantial dissimilarities in the specific compounds inherent to varying tea categories, as ascertained via the devised and duly validated approach. The implications of this compositional elucidation serve as a pertinent benchmark for the comprehensive assessment and classification of tea specimens. [ABSTRACT FROM AUTHOR]

Background: The R2R3-MYB transcription factors are a crucial and extensive gene family in plants, which participate in diverse processes, including development, metabolism, defense, differentiation, and stress response. In the Lingnan region of China, Morinda officinalis is extensively grown and is renowned for its use as both a medicinal herb and food source. However, there are relatively few reports on the R2R3-MYB transcription factor family in M.officinalis. Results: In this study, we identified 97 R2R3-MYB genes in the genome of Morinda officinalis and classified them into 32 subgroups based on phylogenetic comparison with Arabidopsis thaliana. The lack of recent whole-genome duplication events in M.officinalis may be the reason for the relatively few members of the R2R3-MYB family. We also further analyzed the physical and chemical characteristics, conserved motifs, gene structure, and chromosomal location. Gene duplication events found 21 fragment duplication pairs and five tandem duplication event R2R3-MYB genes in M.officinalis may also affect gene family expansion. Based on phylogenetic analysis, cis-element analysis, co-expression analysis and RT-qPCR, we concluded that MoMYB33 might modulate flavonol levels by regulating the expression of 4-coumarate-CoA ligase Mo4CL2, chalcone isomerase MoCHI3, and flavonol synthase MoFLS4/11/12. MoMYB33 and AtMYB111 showed the highest similarity of 79% and may be involved in flavonol synthase networks by the STRING database. Moreover, we also identified MoMYB genes that respond to methyl Jasmonate (MeJA) and abscisic acid (ABA) stress by RT-qPCR. Conclusions: This study offers a thorough comprehension of R2R3-MYB in M.officinalis, which lays the foundation for the regulation of flavonol synthesis and the response of MoMYB genes to phytohormones in M.officinalis. [ABSTRACT FROM AUTHOR]

Background: Few studies assess cord blood biomarkers to predict prenatal exposure to di(2-ethylhexyl) phthalate (DEHP) on the development of allergic diseases later in childhood. IL-33 has been indicated to play an important role in allergic diseases. We evaluated the association of prenatal DEHP exposure and IL-33 in cord blood on the development of allergic diseases. We also investigated the mechanism of DEHP in human lung epithelial cells and asthma animal models. Methods: 66 pregnant women were recruited, and their children followed when they were aged 3 years. Maternal urinary DEHP metabolites were determined using liquid chromatography-electrospray-ionization-tandem mass spectrometry. The effect of DEHP on IL-33 production was investigated in human lung epithelial cells and club cell-specific aryl hydrocarbon receptor (AhR) deficiency mice. ELISA and RT-PCR, respectively, measured the IL-33 cytokine concentration and mRNA expression. Results: The concentrations of maternal urinary DEHP metabolites and serum IL-33 in cord blood with childhood allergy were significantly higher than those in the non-childhood allergy group. DEHP and MEHP could induce IL-33 production and reverse by AhR antagonist and flavonoids in vitro. Enhanced ovalbumin-induced IL-4 and IL-33 production in bronchoalveolar lavage fluid (BALF) by DEHP exposure and suppressed in club cell-specific AhR null mice. Kaempferol has significantly reversed the DEHP effect in the asthma animal model. Conclusions: Cord blood IL-33 level was correlated to childhood allergy and associated with maternal DEHP exposure. IL-33 might be a potential target to assess the development of DEHP-related childhood allergic disease. Flavonoids might be the natural antidotes for DEHP. [ABSTRACT FROM AUTHOR]

• Enicostema axillare has a long history of medicinal use in south Africa. • It is used to treat cough, congestion, alleviation of fever, diabetes, and a range of other diseases. • This review summarizes its botany, traditional uses, phytochemistry, pharmacology, and toxicology. • Swertiamarin, a secoiridoid glycoside, is considered the major chemotaxonomical marker. • E. axillare subsp. littorale studied in clinical trials showed potential treatment for diabetes. Enicostema axillare (Lam.) A. Raynal, commonly known as the Indian whitehead, has a long history of medicinal use in India and some parts of Africa, including South Africa. In ancient times, the plant was often used to treat cough, congestion, alleviation of fever, diabetes, and a range of other diseases. The plant has also demonstrated various pharmacological activities. However, these reports have not been reviewed. Therefore, this review aims to comprehensively summarize the botany, traditional medicinal uses, phytochemistry, pharmacology, and toxicology of E. axillare , providing reference to discover its therapeutic values for further research. To this end, relevant information on E. axillare was retrieved from scientific databases, including Science Direct, Web of Science, Google Scholar, PubMed, Scopus, and World Flora Online. At present, 60 phytoconstituents have been identified and isolated from E. axillare , including flavonoids, steroids, saponins, triterpenoids, flavonols, phenolics, glycosides, volatile oil, and other compounds. Swertiamarin, a secoiridoid glycoside, is considered the major chemotaxonomical marker of the plant responsible for its diverse bioactivities. The extracts and the active constituents of E. axillare have been investigated and reported to demonstrate some pharmacological activities in preclinical studies, including but not limited to antioxidant, anti-inflammatory, anticancer, antidiabetic, antihyperlipidemic, antipyretic, hepatoprotective, and antinociceptive activities. In addition, E. axillare subsp. littorale has undergone some clinical trials with effective outcomes on diabetes. The phytoconstituents and diverse pharmacological activities of E. axillare and its subspecies (littorale) reported in this study provide researchers with a valued context and reference on the current research status of this medicinal plant and direction for further investigation. [ABSTRACT FROM AUTHOR]

Propolis is a natural bee-produced substance with antimicrobial, anti-inflammatory, and wound-healing properties, containing some components from the leaves, buds and resins of plants. It has been used for centuries for various health benefits. In this manuscript, our group reviewed the radioprotective effect of propolis using PubMed and Embase, and our review was conducted according to the PRISMA statement. Finally, 27 articles were included in this review, which includes the radioprotective effect of propolis from cell-based studies (n = 8), animal models (n = 14), and human trials (n = 5). Results reflected that the dosage forms of propolis extracted in the scientific literature were ethanolic extracts of propolis, a water-soluble derivate of propolis, or capsules. The efficacy of the radioprotective properties from propolis is extracted from the bibliography, as several compounds of this resinous mixture individually or synergistically are possible candidates that have the radioprotective effect. In fact, studies prior to 2011 lacked a comprehensive characterization of propolis due to the variability in active compounds among different batches of propolis and were limited to analytical techniques. Furthermore, in this manuscript, we have selected studies to include primarily propolis types from Brazil, Croatia, Egypt, European countries, and those commercialized in Spain. They all contained ethanolic extract of propolis (EEP) and were influenced by different dosage forms. EEP showed a significant presence of lipophilic bioactive compounds like flavones, flavonols, and flavanones. [ABSTRACT FROM AUTHOR]

Recently, consumer preferences for bilberries have increased markedly. This fact is probably related to their natural constituents, such as phenolic compounds including anthocyanins and tannins, as well as the vitamins and minerals they contain. Phenolic compounds are known for their numerous beneficial effects on human health. Moreover, bilberry fruits have been shown to inhibit the activity of carbohydrate hydrolyzing enzymes, which can significantly decrease the postprandial increase in blood glucose levels. Thus, the aim of the present study is to investigate the inhibitory effect of Vaccinium myrtillus L. extracts on key enzyme α-amylase, linked to type 2 diabetes. No data have been published on the inhibitory properties of Vaccinium myrtillus L. fruits growing wild in Bulgaria against carbohydrate enzymes. Bilberry extracts were analyzed for total polyphenols, total anthocyanin content, antioxidant activity and their inhibitory properties against α-amylase. The contents of flavonols, anthocyanins and stilbenes were determined by HPLC analysis. The identified flavonols in the analyzed bilberry extracts were mainly represented by quercetin derivatives as rutinoside. The predominant anthocyanins for both aqueous and organic solvents were delphinidin-3-galactoside and malvidin-3-glucoside. The results revealed that bilberry extracts are effective inhibitors of α-amylase, with IC50 values from 20.8 to 194.8 μg GAE/mL. All the samples proved to have antioxidant activity measured by three different in vitro assays (FRAP, CUPRAC and DPPH). The inhibitory properties of V. myrtillus L. extracts may provide a new direction in the development and research of new pharmaceuticals for the suppression of postprandial hyperglycemia in diabetic patients. [ABSTRACT FROM AUTHOR]

Rapeseed's (Brassica napus L.) colorful petals have important ornamental values. However, the mechanisms of regulating petals coloration in rapeseed are still unknown. In our study, we investigated the key differential coloring substances in nine rapeseed cultivars with different petal colors, and 543 metabolites were detected and characterized through UPLC-HESI-MS/MS. Among them, the kinds and contents of flavonols, flavones, and anthocyanidins were the main contributors to petals' coloration. Tamarixetin-, quercetin-, butin-, naringenin- and luteolin-derivates were the main pigment bases in white and yellow petals. Peonidin-3,5-O-diglucoside, peonidin-3-O-(6″-O-caffeoyl)glucoside, and quercetin-derivatives were the main coloring substances in pink petals. Acylated cyanidin derivatives might lead to a series of different purple petal colors. Glycosylated anthocyanins were responsible for the coloration of rapeseed red petals, and peonidin-3-O-glucoside and kaempferol-derivatives were mainly detected from the red petals. These results provide comprehensive insights into the difference in flavonoid metabolites in rapeseed petals with different colors and supply theoretical supports for the breeding of novel colorful rapeseed cultivars. [ABSTRACT FROM AUTHOR]

Flos Sophorae Immaturus (FSI) is a dried flower bud derived from Sophora japonica L. FSI contains various phytochemicals, including rutin, quercetin, kaempferol, isorhamnetin, genistein, and Flos Sophorae saponins. The active components of FSI have anti-cancer, antithrombotic, analgesic, antibacterial, antiviral, anti-aging, anti-inflammatory, anti-allergic, and antioxidant remarkable pharmacological and nutritional properties. There is a growing interest in developing FSI both as a functional food and a health product, as well as its use in other applications including dyes and cosmetics. However, the lack of systematic information on the composition of FSI and its specific health effects has greatly hindered its application as sustainable, functional plant material. Herein, we reviewed the currently available research on the nutritional components and biological characteristics of FSI and described the relationship between FSI-derived polyphenols and their biological activities in vitro and in vivo. This review systematically summarizes the medicinal and edible uses of FSI and proposes directions for future research, which will provide a theoretical basis for the utilization of FSI as a health supplement, functional food product, and natural pigment raw material in the future. [ABSTRACT FROM AUTHOR]

Alfalfa (Medicago sativa L.) is one of the most extensively grown leguminous forage worldwide. Environmental saline-alkali stress significantly influences the growth, development, and yield of alfalfa, posing a threat to its agricultural production. However, little is known about the potential mechanisms by which alfalfa responds to saline-alkali stress. Here, we investigated these mechanisms by cloning a saline-alkali-induced flavonol synthase gene (MsFLS13) from alfalfa, which was previously reported to be significantly upregulated under saline-alkali stress, and examining its function in the saline-alkali response. Overexpression of MsFLS13 in alfalfa promoted plant tolerance to saline-alkali stress by enhancing flavonol accumulation, antioxidant capacity, osmotic balance, and photosynthetic efficiency. Conversely, MsFLS13 inhibition using RNA interference reduced flavonol synthase activity and inhibited hairy root growth under saline-alkali stress. Yeast one-hybrid and dual-luciferase reporter assays indicated that the R2R3-MYB MsMYB12 transcription factor activates MsFLS13 expression by binding to the MBS motif in the MsFLS13 promoter. Further analysis revealed that abscisic acid mediates the salinealkali stress response partially by inducing MsMYB12 and MsFLS13 expression, which consequently increases flavonol levels and maintains antioxidant homeostasis in alfalfa. Collectively, our findings highlight the crucial role of MsFLS13 in alfalfa in response to saline-alkali stress and provide a novel genetic resource for creating saline-alkali-resistant alfalfa through genetic engineering. [ABSTRACT FROM AUTHOR]

In this overview, the current knowledge of the constituents of flavonoids isolated from the roots of Sophora flavescens (kushen) is updated. Flavonoids consist of several classes, such as flavanones, flavonols, chalcones, isoflavones, biflavonoids, flavanols, and flavones. The most common compounds are kurarinone (KRN), sophoraflavanone G (SFG), 2ʹ-methoxykurarinone, kuraridine, isoxanthohumol, and formononetin. KRN and SFG are two major flavanones with more vital anticancer properties than other flavonoids. From the literature, the cytotoxic values of KRN and SFG are variable and depend on the type of cancer cells tested. The anticancer activities of these two flavonoids involve different molecular mechanisms. Clinical trials are needed before anticancer drugs from KRN and SFG can be developed. [ABSTRACT FROM AUTHOR]

The fruits of Prunus domestica L. are a valuable source of phenolic compounds, in particular hydroxycinnamic acids and their esters. Hybrid origin of Prunus domestica hexaploid species, the ample number of the varieties, and expanded geograph y of the cultivation preclude scientists from arriving at a definitive conclusion on the content levels and composition of phenolic compounds in plum fruits. The goal of our study is to determine and identify the phenolic composition of fruits of Prunusdomestica L. grown in Tambov oblast of the Russian Federation. The research focused on eight fresh-eating and all-purpose varieties. Experimental plantations were established in 2014 in the 6 × 3-m setup. The plum–cherry hybrid (SVG) 11–19 was used as a rootstock. The phenolic components of plum fruits were determined by reverse phase high performance liquid chromatography (RP HPLC) using a Thermo Ultimate 3000 liquid chromatography system equipped with a DAD‑3000 detector. A chromatography run of the plum fruit methanol extracts was performed through a mobile phase binary gradient represented by acetonitrile and aqueous potassium dihydrogen phosphate acidified with orthophosphoric acid to pH 2.5. The hydroxycinnamic acids in the plum fruits were determined to be as follows: 5.33–181.54 mg/100 g of 4-Caffeoylquinic acid, 1.69‒31.73 mg/100 g of 5-Caffeoylquinic acid, 0.54–5.77 mg/100 g of 3-p-Coumaroylquinic acid, and 0.04–0.63 mg/100 g of 3-Caffeoylquinic acid. Quercitin-3-rutinoside at 0.77–9.17 mg/100 g was dominant among flavonols. Three anthocyanins, namely, cyanidin-3-glucoside, cyanidin-3-rutinoside, and peonidin-3-glucoside, were identified in the studied plum fruits. The structural composition of plum fruit anthocyanins was dominated by cyaniding-3-glucoside, accounting for 60 to 90% of the total anthocyanin content. The obtained data on the content of phenolic components in fruits of specified plum varieties (Prunus domestica L.) point toward the potential of the use of the specified plum varieties as a source of hydroxycinnamic acids, anthocyanins, and flavonols in the population diet. [ABSTRACT FROM AUTHOR]

Chromatographic fractionation of a methanol extract of Helichrysum rutilans afforded seven known compounds. The isolated compounds were identified as 5,7,8-trihydroxy-3,6-dimethoxyflavone-8-O-2-methyl-2-butanoate (C-1), 5,7-dihydroxy-3,6,8-trimethoxyflavone (C-2), 5-hydroxy-3,6,7,8-tetramethoxyflavone (C-3), 5-hydroxy-3,6,7-trimethoxyflavone (C-4), ent-kaurenoic acid (C-5), ent-kauran-18-al (C-6), and 15-α-hydroxy-(-)-ent-kaur-16-en-19-oic acid (C-7). Compounds C-1–C-4 demonstrated high antioxidant capacities on ORAC hydroxyl radical (2.114 ± 4.01; 2.413 ± 6.20; 1.924 ± 16.40; 1.917 ± 3.91) × 106; ORAC peroxyl radical (3.523 ± 3.22; 2.935 ± 0.13; 2.431 ± 8.63; 2.814 ± 5.20) × 103 µMTE/g; and FRAP (1251.45 ± 4.18; 1402.62 ± 5.77) µMAAE/g, respectively. Moderate inhibitory activities against Fe2+-induced lipid peroxidation were observed for C-1–C-4 as IC50 values of 13.123 ± 0.34, 16.421 ± 0.92, 11.64 ± 1.72, 14.90 ± 0.06 µg/mL, respectively, while their respective anti-tyrosinase activities with IC50 values of 25.735 ± 9.62, 24.062 ± 0.61, 39.03 ± 13.12, 37.67 ± 0.98 µg/mL were also observed. All compounds demonstrated TEAC values within the range of 1105–1424 µMTE/g. The result is an indication that a methanol extract of H. rutilans might possibly be a good source of natural antioxidants against ailments caused by cellular oxidative stress and as inhibitors against skin depigmentation, as well as possible raw materials needed for slowing down perishable agricultural products. This is the first report on the phytochemical and biological evaluation of H. rutilans. [ABSTRACT FROM AUTHOR]

Consumer demand for natural and healthier products has led to an increasing interest in the bioactive and therapeutic properties of plant extracts. In this study, we evaluated the phenolic compounds profile, bioactivities, and toxicities of plant extracts from eight European flora species, including Calendula officinalis L., Calluna vulgaris (L.) Hull, Hippophae rhamnoides L., Juglans regia L., Mentha cervina L., Rubus idaeus L., Sambucus nigra L., and Vitis vinifera L. The aim was to identify potential preservatives of natural origin. Phenolic compounds were identified by HPLC-DAD-ESI-MS. Caffeic acid derivatives, ellagitannins, flavonols, and flavones were the major phenolic compounds identified. The total phenolic content varied from 16.0 ± 0.2 (V. vinifera) to 123 ± 2 mg/g (H. rhamnoides) of dry extract. All extracts showed antioxidant potential and exhibited activity against some of the microorganisms tested. S. nigra showed the highest activity in the inhibition of oxidative hemolysis (OxHLIA) assay and H. rhamnoides, notably, had the lowest IC50 values in TBARS and DPPH assays, as well as the lowest minimum inhibitory concentration (MIC) values. Regarding in vitro cytotoxicity, in tumor and non-tumor cell lines, although some extracts revealed toxicity against normal cells, it was found that the samples C. vulgaris, V. vinifera and R. idaeus might be used against tumor cells since the active concentration is much lower than the one causing toxicity. In vivo acute toxicity tests using Artemia franciscana suggest low toxicity for most extracts, with LC50 > 400 mg/L. These results showed the potential of the studied extracts as natural preservatives, given their richness in compounds with bioactive properties, highlight their potential value to the production chain. [ABSTRACT FROM AUTHOR]

The banana is a tropical fruit characterized by its composition of healthy and nutritional compounds. This fruit is part of traditional Ecuadorian gastronomy, being consumed in a wide variety of ways. In this context, unripe Red Dacca banana samples and those submitted to different traditional Ecuadorian heating treatments (boiling, roasting, and baking) were evaluated to profile their phenolic content by ultra-high-performance liquid chromatography coupled to high-resolution mass spectrometry (UHPLC-HRMS) and the antioxidant activity by ORAC, ABTS, and DPPH assays. A total of sixty-eight phenolic compounds were identified or tentatively identified in raw banana and treated samples, highlighting the content in flavonoids (flavan-3-ols with 88.33% and flavonols with 3.24%) followed by the hydroxybenzoic acid family (5.44%) in raw banana samples. The total phenolic compound content significantly decreased for all the elaborations evaluated, specifically from 442.12 mg/100 g DW in fresh bananas to 338.60 mg/100 g DW in boiled (23.41%), 243.63 mg/100 g DW in roasted (44.90%), and 109.85 mg/100 g DW in baked samples (75.15%). Flavan-3-ols and flavonols were the phenolic groups most affected by the heating treatments, while flavanones and hydroxybenzoic acids showed higher stability against the heating treatments, especially the boiled and roasted samples. In general, the decrease in phenolic compounds corresponded with a decline in antioxidant activity, evaluated by different methods, especially in baked samples. The results obtained from PCA studies confirmed that the impact of heating on the composition of some phenolic compounds was different depending on the technique used. In general, the heating processes applied to the banana samples induced phytochemical modifications. Even so, they remain an important source of bioactive compounds for consumers. [ABSTRACT FROM AUTHOR]

The prospects of commercialization in the market for exotic fruits are increasingly promising in Brazil. Pitaya, for instance, is a fruit that can be consumed either fresh or processed. During the processing of its pulp, there is generation of residues, mainly from the peel. The aim of this study was to evaluate the convective drying of pitaya peel and the extraction of bioactive compounds by cold maceration and ultrasound-assisted methods, as well as the microencapsulation (ME) process. The peels were cut and dried in an air circulation oven at 60 °C. Some empirical mathematical models were used to describe the drying process (Henderson & Pabis, Page, Peleg, Silva et al., Wang & Singh). The powders obtained from drying were subjected to ultrasound-assisted and cold maceration (4 °C) extractions and ME. Fresh peels (FR), extract obtained by ultrasound (US), extract obtained by cold maceration (CM) and microencapsulated extract (ME) were characterized for the Folin–Ciocalteu reducing capacity (FCRC), antioxidant capacity and phenolic compound profile by High-Performance Liquid Chromatography (HPLC). According to the results, the Peleg model showed the best description for the convective drying of pitaya peel at 60 °C. ME extract showed the highest values for antioxidant capacity by DPPH and FCRC. US and CM extracts showed significant results at 5% probability level for antioxidant capacity by ABTS and FRAP, respectively. The main group of phenolic compounds quantified was flavonols, among which quercetin 3-glucoside had the highest concentration (70.25–361.45 g 100 g−1), and high levels were quantified for the betalains betanin and isobetanin, between 167.23 and 326.43 g 100 g−1. The ME sample had the highest content of total phenolics quantified (TPQ) (1017.18 g 100 g−1), highlighting its technological potential for food production. [ABSTRACT FROM AUTHOR]

Investigation of the leaves of Bauhinia thonningii Schum led to the isolation and identification of a new flavonol derivative, 6-C-methylquercetin-3,4'-dimethyl ether (1) together with eleven known compounds (2–13), with two of them (10 and 11) obtained as a mixture. Their structures were established by extensive spectroscopic analyses. Antibacterial activity of compound 1 as well as the reference antibiotic, ciprofloxacin was tested on Gram-negative multidrug-resistant bacteria overexpressing active efflux pumps, and against methicillin-resistant strains of Staphylococcus aureus (MRSA). Samples were tested alone and in combination with an efflux pump inhibitor (EPI), phenylalanine-arginine-β-naphthylamide (PAßN). Results show that when compound 1 was tested alone, its inhibitory effects were obtained on 7/10 tested bacteria with the highest MIC value of 128 µg/mL whilst in the presence of EPI, this activity significantly increase in all the 10 bacteria. An interesting antibacterial activity was obtained with compound 1 against Klebsiella pneumoniae ATCC11296 (MIC of 4 µg/mL), KP55 and Staphylococcus aureus MRSA6 in the presence of the PaßN. [ABSTRACT FROM AUTHOR]

Under the background of toxic and harmful petroleum based adhesives and the rapid depletion of fossil resources, bio-based adhesives have developed rapidly. As an important class of plant tannins, condensed tannins (CTs) possess flavonol units and represent up to 90% of global commercial tannins resources. CTs present unique chemical properties owing to their special polyphenol structures, which is more suitable to replace phenol in adhesives either in reactivity or economy, for its reaction rate with formaldehyde is 3 times that of phenol. In this way, the research progress of bio-based adhesives in recent years was highlighted and a prospect was made in this review, in order to provide reference for the development and application of condensed tannins adhesives. [ABSTRACT FROM AUTHOR]

This study investigated the composition of sugars, organic acids, individual and total phenolic compounds in the pulp, peel, leaves, and bark of a red-fleshed 'Baya Marisa' apple cultivar. As the fruit is known for its red pulp color, the study focused on comparing the profiles of primary and selected secondary metabolites in three sections along the equatorial fruit plane. The analyses were carried out using HPLC–MS system, and compositional differences were compared among fruit segments. Inner fruit segments accumulated higher levels of sorbitol and the sum of sugars and lower levels of citric acid. However, no differences in the sum of organic acids could be determined among segments. The phenolic composition differed among pulp (hydroxycinnamic acids > dihydrochalcones ≈ anthocyanins ≈ flavanols > flavonols), peel (flavanols > anthocyanins > dihydrochalcones > flavonols > hydroxycinnamic acids), leaves (flavonols > dihydrochalcones > hydroxycinnamic acids > anthocyanins), and bark (dihydrochalcones > flavonols > flavanols > anthocyanins > hydroxycinnamic acids). The greatest phenolic diversity was detected in bark (25), followed by leaves (18), peel (17) and finally, pulp (11). Three anthocyanins (cyanidin-3-O-galactoside > cyanidin-3-O-arabinoside > peonidin-3-O-galactoside) were determined in all 'Baya Marisa' tissues with their content highest in the peel. The innermost sections of the fruit were characterized by higher levels of dihydrochalcones and lower levels of most flavanols, flavonols and anthocyanins. These were predominant in the apple pulp nearest to the peel, with cyanidin-3-O-galactoside being the prevalent representative. Accumulation of anthocyanins in pulp is a rare trait in apples, and therefore, the distinct distribution and diversity of metabolites in this cultivar highlights its potential for high-nutrient products such as juices, apple chips or purees. [ABSTRACT FROM AUTHOR]

Matthiola longipetala subsp. livida is an annual herb in Brassicaceae that has received little attention despite the family's high reputation for health benefits, particularly cancer prevention. In this study, UPLC-HRMS-MS analysis was used for mapping the chemical constituents of different plant parts (i.e., flowers, leaves, and roots). Also, spectral similarity networks via the Global Natural Products Social Molecular Networking (GNPS) were employed to visualize their chemical differences and similarities. Additionally, the cytotoxic activity on HCT-116, HeLa, and HepG2 cell lines was evaluated. Throughout the current analysis, 154 compounds were annotated, with the prevalence of phenolic acids, glucosinolates, flavonol glucosides, lipids, peptides, and others. Predictably, secondary metabolites (phenolic acids, flavonoids, and glucosinolates) were predominant in flowers and leaves, while the roots were characterized by primary metabolites (peptides and fatty acids). Four diacetyl derivatives tentatively assigned as O-acetyl O-malonyl glucoside of quercetin (103), kaempferol (108 and 112), and isorhamnetin (114) were detected for the first time in nature. The flowers and leaves extracts showed significant inhibition of HeLa cell line propagation with LC50 values of 18.1 ± 0.42 and 29.6 ± 0.35 µg/mL, respectively, whereas the flowers extract inhibited HCT-116 with LC50 24.8 ± 0.45 µg/mL, compared to those of Doxorubicin (26.1 ± 0.27 and 37.6 ± 0.21 µg/mL), respectively. In conclusion, the flowers of M. longipetala are responsible for the abundance of bioactive compounds with cytotoxic properties. [ABSTRACT FROM AUTHOR]

The QSAR models are employed to predict the anti-proliferative activity of 81 derivatives of flavonol against prostate cancer using the Monte Carlo algorithm based on the index of ideality of correlation (IIC) criterion. CORAL software is employed to design the QSAR models. The molecular structures of flavonols are demonstrated using the simplified molecular input line entry system (SMILES) notation. The models are developed with the hybrid optimal descriptors i.e. using both SMILES and hydrogen-suppressed molecular graph (HSG). The QSAR model developed for split 3 is selected as a prominent model ( R Validation 2 = 0.727, IIC validation = 0.628, Q Validation 2 = 0.642, and r ¯ m 2 =0.615). The model is interpreted mechanistically by identifying the characteristics responsible for the promoter of the increase or decrease. The structural attributes as promoters of increase of pIC50 were aliphatic carbon atom connected to double-bound (C...=..., aliphatic oxygen atom connected to aliphatic carbon (O...C...), branching on aromatic ring (c...(...), and aliphatic nitrogen (N...). The pIC50 of eight natural flavonols with pIC50 more than 4.0, were predicted by the best model. The molecular docking is also performed for natural flavonols on the PC-3 cell line using the protein (PDB: 3RUK). [ABSTRACT FROM AUTHOR]

Human adenovirus type-7 (HAdV-7) is a common pathogen that may cause significant morbidity as well as severe complications. Currently, there is no approved drug for the treatment of HAdV-7 infections and the contemporary strategy mainly rely on nonspecific antivirals. Glycyrrhiza glabra; (licorice), is a well-recognized edible plant used in food and beverages. The plant is renowned for its pharmacological and biological activities including antiviral activities against wide range of viruses. The following study reported for the first time the anti-adenoviral activity of licorice extract using in-vitro cytopathic inhibitory assay. Different solvent fractions showed promising activity with IC50 reaching 1.431 μg/ml. Certain fractions had selectivity index (SI) greater than 10 indicating their efficacy together with relatively low cytotoxic effect. Metabolic profiling using LC-HRMS/MS resulted in identification of 41 compounds from licorice fractions. Chemometric modeling using Orthogonal Projections to Latent Structures (OPLS) suggested the compounds; kaempferol-3-O-rutinoside, violanthin, rhamnoliquiritin, isoliquiritigenin isomer, licoagroside B and liquiritin apioside as potential markers against (HAdV-7). Finally, kaempferol-3-O-rutinoside was further confirmed via in-vitro adenovirus inhibitory assay to possess strong antiviral activity with IC50 and CC50 of 54.7 ± 1.93 μM and 655.7 ± 2.22 μM, respectively. [ABSTRACT FROM AUTHOR]

SARS-CoV-2 has posed a threat to the health of people around the world because of its strong transmission and high virulence. Currently, there is no specific medicine for the treatment of COVID-19. However, for a wide variety of medicines used to treat COVID-19, traditional Chinese medicine (TCM) plays a major role. In this paper, the effective treatment of COVID-19 using TCM was consulted first, and several Chinese medicines that were frequently used apart from their huge role in treating it were found. Then, when exploring the active ingredients of these herbs, it was discovered that most of them contained flavonoids. Therefore, the structure and function of the potential active substances of flavonoids, including flavonols, flavonoids, and flavanes, respectively, are discussed in this paper. According to the screening data, these flavonoids can bind to the key proteins of SARS-CoV-2, 3CLpro, PLpro, and RdRp, respectively, or block the interface between the viral spike protein and ACE2 receptor, which could inhibit the proliferation of coronavirus and prevent the virus from entering human cells. Besides, the effects of flavonoids on the human body systems are expounded on in this paper, including the respiratory system, digestive system, and immune system, respectively. Normally, flavonoids boost the body's immune system. However, they can suppress the immune system when over immunized. Ultimately, this study hopes to provide a reference for the clinical drug treatment of COVID-19 patients, and more TCM can be put into the market accordingly, which is expected to promote the development of TCM on the international stage. [ABSTRACT FROM AUTHOR]

SUMMARY: Flavonols are health‐promoting bioactive compounds important for human nutrition, health, and plant defense. The transcriptional regulation of kaempferol and quercetin biosynthesis has been studied extensively, while little is known about the regulatory mechanisms underlying myricetin biosynthesis, which has strong antioxidant, anticancer, antidiabetic, and anti‐inflammatory activities. In this study, the flavonol‐specific MrMYB12 in Morella rubra preferred activating the promoter of flavonol synthase 2 (MrFLS2) (6.4‐fold) rather than MrFLS1 (1.4‐fold) and upregulated quercetin biosynthesis. Furthermore, two SG44 R2R3‐MYB members, MrMYB5 and MrMYB5L, were identified by yeast one‐hybrid library screening using the promoter of flavonoid 3′,5′‐hydroxylase (MrF3′5′H), and transcript levels of these R2R3‐MYBs were correlated with accumulation of myricetin derivatives during leaf development. Dual‐luciferase and electrophoretic mobility shift assays demonstrated that both MrMYB5 and MrMYB5L could bind directly to MYB recognition sequence elements in promoters of MrF3′5′H or MrFLS1 and activate their expression. Protein–protein interactions of MrMYB5 or MrMYB5L with MrbHLH2 were confirmed by yeast two‐hybrid and bimolecular fluorescence complementation assays. MrMYB5L‐MrbHLH2 showed much higher synergistic activation of MrF3′5′H or MrFLS1 promoters than MrMYB5‐MrbHLH2. Studies with Arabidopsis thaliana homologs AtMYB5 and AtTT8 indicated that similar synergistic regulatory effects occur with promoters of MrF3′5′H or MrFLS1. Transient overexpression of MrMYB5L‐MrbHLH2 in Nicotiana benthamiana induced a higher accumulation of myricetin derivatives (57.70 μg g−1 FW) than MrMYB5‐MrbHLH2 (7.43 μg g−1 FW) when MrMYB12 was coexpressed with them. This study reveals a novel transcriptional mechanism regulating myricetin biosynthesis with the potential use for future metabolic engineering of health‐promoting flavonols. [ABSTRACT FROM AUTHOR]

Copaifera langsdorffii Desf. is recognised as one of most famous medicinal and economic species of Copaiba, occurring in several distinct biomes. An untargeted metabolomic approach was used to evaluate the chemical variability of C. langsdorffii from contrasting climates biomes (Atlantic Rainflorest and the semiarid Cerrado). Metabolomic analysis enabled the identification of 11 compounds, including glycosylated flavonoids and galloylquinic acid derivatives. Multivariate analysis highlighted that Cerrado population had a significantly higher concentrations of galloylquinic acid derivatives in comparison to the rainforest biome. Meanwhile, Atlantic Rainforest populations presented higher content of flavonols. Semiarid biome, reduced the concentration of flavonoids, mainly concerning quercetin and kaempferol derivatives, however, in this biome flavonoids were more diverse. Both chemical classes presented relevance to be used as geographical origin chemical markers by qualitative and quantitative features. [ABSTRACT FROM AUTHOR]

Arsenic (As) toxicity negatively impacts plant development, limits agricultural production, and, by entering the food chain, endangers human health. Studies on the use of natural and bioactive molecules in increasing plants' resistance to abiotic stressors, such as As, have gained increasing attention in the last few years. Flavonols are plant secondary metabolites with high potential in stress tolerance due to their roles in signal transmission. Therefore, the focus of this study was to examine the effects of two flavonols, quercetin (Q, 25 μM) and kaempferol (K, 25 μM), on growth parameters, photosynthesis, and chloroplastic antioxidant activity in wheat leaves under As stress (100 μM). As stress reduced the relative growth rate by 50% and relative water content by 25% in leaves. However, applying Q and/or K alleviated the As‐induced suppression of growth and water relations. Exogenous phenolic treatments reversed the effects of As toxicity in photochemistry and maintained the photochemical quantum efficiency of the Photosystem II (Fv/Fm). As exposure increased, the H2O2 content in wheat chloroplasts by 42% and high levels of H2O2 accumulation were also observed in guard cells in confocal microscopy images. Analysis of the chloroplastic antioxidant system has shown that Q and K applications increase the activity of antioxidant enzymes, including superoxide dismutase, peroxidase, and ascorbate peroxidase. Phenolic applications have induced the ascorbate–glutathione (AsA‐GSH) cycle in charge of the protection of the cellular redox balance in different ways. It has been determined that Q triggers the AsA renewal, and K maintains the GSH pool. As a result, Q and K applications provide tolerance to wheat plants under As stress by increasing the chloroplastic antioxidant system activity and protecting photosynthetic reactions from oxidative damage. This study reveals the potential use of plant phenolic compounds in agricultural systems as a biosafe strategy to enhance plant stress tolerance, hence increasing yield. [ABSTRACT FROM AUTHOR]

Ranunculus japonicus Thunb. is a traditional Chinese herb. Plants in the genus Ranunculus are generally rich in flavonoids, which have antibacterial, anti‐infective, and other pharmacological effects. However, owing to the lack of reference genomes, little is known about the flavonoid biosynthetic pathway in R. japonicus. In this study, PacBio isoform sequencing (PacBio iso‐seq) and DNA nanoball sequencing (DNB‐seq) were combined to build a full‐length transcriptome database for three different tissues of R. japonicus. A total of 395,402 full‐length transcripts were obtained, of which 308,474 were successfully annotated. A Kyoto Encyclopedia of Genes and Genomes analysis identified 29 differentially expressed genes encoding nine key enzymes for flavonoid biosynthesis. Correlation analysis indicated that flavanone 3‐hydroxylase and flavonol synthase genes might have key roles in the accumulation of flavonoid substances in the different tissues of R. japonicus. The structures of chalcone synthase and chalcone isomerase enzymes were spatially modeled. Reverse‐transcription quantitative PCR was used to verify gene expression levels of key enzymes associated with flavonoid biosynthesis. In addition, 22 MYB transcription factors involved in flavonoid biosynthesis and phenylpropanoid biosynthesis were discovered. The reliable transcriptomic data from this study provide genetic information about R. japonicus as well as insights into the molecular mechanism of flavonoid biosynthesis. The results also provide a basis for developing the medicinal value R. japonicus. [ABSTRACT FROM AUTHOR]

The aim of this in vitro study was to evaluate the anthelmintic effects of extracts of Gliricidia sepium on sheathed and exsheathed larvae of Haemonchus contortus. Larvae of this parasite were incubated at 20–25 °C in hydro-methanolic extracts of leaves from this tropical tree at concentrations of 12.5, 25, 50, 100, and 200 mg/mL for 24, 48, or 72 h. Water and ivermectin were negative and positive controls, respectively. Total phenolic compounds of leaves of G. sepium were 6.4 ± 2.4 mg/g of dry matter. Other compounds identified in this leguminous tree by HPLC-mass spectrometry and that may be responsible for the anthelmintic effects observed were vanillin 4-sulfate, prodelphinidin p-coumaroyl glucose, kaempferol 3-o-glucosyl-rhamnosyl-glucoside, kaempferol-3-O-xylosyl rutinoside, p-coumaric acid, luteolin 7-rutinoside, isorhamnetin 3-glucoside-7-rhamnoside, and dihydro ferulic acid. At doses of 100 mg/mL mortality rate of sheathed and exsheathed H. contortus was 21.6 and 44.7%, respectively for 72 h of incubation. At 200 mg/mL, the hydro-methanolic extracts of G. sepium killed 61.5 and 93.8% of sheathed and exsheathed larvae, respectively, after 72 h of incubation. The effective concentration of the G. sepium extract for 50% sheathed and exsheathed larvae mortality (EC50) after 72 h of incubation was 74 mg/mL (CI = 46–100) and 68 mg/ mL (CI= 32–100), respectively. The significant (P<0.001) ability to kill larvae compared to the negative controls, suggests in vitro anthelmintic properties of G. sepium against H. contortus. [ABSTRACT FROM AUTHOR]

This review study investigates conventional anticancer treatments derived from the world's different parts as a wonderful substitute for pharmaceuticals since they have fewer or no side effects and can fix the disease at its source. This study provides thorough information regarding physiologically active substances derived from various parts of the plant for cancer treatment such as Alkaloids (ervine, methylervine, ervolanine, and aervolanine), Terpenoids, Vitamins, Coumarins, Tannins, Carbohydrates, Flavonoids (kaempferol, quercetin, isorhamnetin, persinol, persinosides A and B), Fatty Acids, and Essential Oils). This technique is beneficial in clinical studies for breast, prostate, and colon cancer. The ongoing rise in cancer incidence, the inability of traditional chemotherapies to manage cancer, and the excessive toxicity of chemotherapies all call for a new strategy. The first trial to establish the effectiveness of chemoprevention was conducted in breast cancer patients using tamoxifen, which indicated a substantial reduction in invasive breast cancer. The effectiveness of utilizing chemopreventive drugs to protect high-risk people from cancer suggests that the technique is sound and promising. Dietary components such as capsaicin, cucurbitacin B, isoflavones, catechins, lycopene, benzyl isothiocyanate, phenethyl isothiocyanate, and piperlongumine have been shown to suppress cancer cell growth, indicating that they might be used as chemopreventive agents. [Display omitted] • Different plant families are discussed which contain antitumour activities. • Different type of cancer is discussed in brief. • Different plant parts stem, leaves, bark etc. discussed. • Phytochemical are discussed for particular cancer treatments. Author arcid ID [ABSTRACT FROM AUTHOR]

• Medicinal plants can show allelopathic potential. • Plant extracts rich in phenols, flavonoids and tannins showed high allelopathic activities. • Annona dioica (Annonaceae), Stryphnodendron adstringens (Fabaceae) and Palicourea crocea (Rubiaceae) decelerated U. decumbens seed germination. • Alternative methods for controlling U. decumbens in areas of ecological restoration. Invasive grasses, those of the genus Urochloa act aggressively, thereby inhibiting the germination and growth of native species. We investigated the allelopathic potential and constituent content of different plant species to determine their effect on the germination of Urochloa decumbens (Stapf) R.D. Webster. Eighteen (18) species from the families Anacardiaceae (1), Annonaceae (6), Euphorbiaceae (1), Fabaceae (2), Myrtaceae (1), Rubiaceae (4), Sapindaceae (2), and Tropaeolaceae (1) were selected to obtain methanolic extracts at 1% (m/v). The total phenols, flavonoids, condensed tannins, flavonols, and saponins were evaluated by colorimetric methods. To evaluate the allelopathic effect of methanolic extracts 25 seeds from U. decumbens were distributed in Petri dishes containing two sheets of germitest paper and 2 mL of extract, and they were maintained at 25 °C under white light. All methanolic extracts showed total phenols, flavonoids, flavonols, and condensed tannins; however, saponin was identified in A. coriacea, A. crassiflora, A. sylvatica, Psychotria carthagenensis, P. leiocarpa, and Tropaeolum majus. Annona dioica (Annonaceae), Stryphnodendron adstringens (Fabaceae), and Palicourea crocea (Rubiaceae) have allelopathic potential and showed decelerated U. decumbens seed germination and inhibited hypocotyl and radicle growth. These findings provide insights into alternative methods for controlling U. decumbens in areas of ecological restoration. [ABSTRACT FROM AUTHOR]

Inflammation is an innate reaction of the body of an individual when subjected to the noxious factors repeatedly. Pharmacological approaches focused at disrupting cytokine signaling networks have become significant therapeutic alternatives for the treatment of inflammatory illnesses, cancer and autoimmune disorders. High levels of inflammatory mediators, particularly interleukin IL‐1, IL‐6, IL‐18, IL‐12, and tumor necrosis factor alpha leads to a cytokine storm in the body. Among all the released cytokines in a patient suffering from inflammatory disorder, IL‐6 mediator has a pivotal role in this inflammatory cascade which progresses to a cytokine storm. Therefore, the blockage of the IL‐6 inflammatory mediator could be a promising treatment option for the patients with hyper inflammatory conditions. The phytochemicals could provide the new lead compounds against the IL‐6 mediator. Ficus carica has been the ideal plant of research and investigation due to its commercial, economic and medical importance. The anti‐inflammatory properties of F. carica were further investigated by in silico and in vivo approaches. The docking scores of Cyanidin‐3,5‐diglucoside, Kaempferol‐7‐O‐rutinoside, Cyanidin‐3‐rhamnoglucoside, and Rutin are −9.231, −8.921, −8.840, and −8.335 Kcal/mole respectively. The free energy of binding and stability of the docked complexes of these top four phytochemicals with the IL‐6 were further analyzed by Molecular Mechanics‐Generalized Born Surface Area and Molecular Dynamic simulations, respectively. The in vivo anti‐inflammatory carrageenan‐induced rat paw edema model was used for the validation of in silico results. The maximum percentage paw edema inhibition with petroleum ether and ethyl acetate was 70.32% and 45.05%, respectively. The in vivo anti‐inflammatory activity confirms the anti‐inflammatory potential of F. carica. Therefore, it is predicted that Cyanidin‐3,5‐diglucoside, Kaempferol‐7‐O‐rutinoside, Cyanidin‐3‐rhamnoglucoside, and Rutin have the potential to inhibit the IL‐6 mediator which will aid in mitigating the cytokine storm in patients with acute inflammations. Significance statement: The Ficus carica plant has been included in traditional alternative systems of medicine for the treatment of various ailments since the ancient times. Plant leaves and fruits have profound chemical constituents possessing anti‐inflammatory activity reported in numerous research publications. The current study is designed to evaluate and investigate further, the anti‐inflammatory (IL‐6 inhibitory) potential of F. carica from both computational (in silico) and in vivo methods for discovery of new and potentially better treatment. Both in vivo and in silico studies justify the IL‐6 inhibitory activity of F. carica phytochemicals and show that they can prevent the hyper‐inflammatory condition known as "cytokine storm" in the patients. The most effective IL‐6 inhibitor phytochemicals include Cyanidin‐3,5‐diglucoside, Kaempferol‐7‐O‐rutinoside, Cyanidin‐3‐rhamnoglucoside, and Rutin. In the future, these phytochemicals will require further pharmacokinetic and toxicity studies along with clinical trials to provide a new treatment option for patients with acute inflammatory conditions. [ABSTRACT FROM AUTHOR]

Several studies have revealed that fruit-zone leaf removal could change the microclimate of grapevine growth, thereby causing complex effects on fruit composition. This study analyzed the profiles of volatiles in Cabernet Sauvignon (Vitis vinifera L.) grapes exposed to leaf removal treatment at different phenological periods in three continuous years. The treatments (leaf removal before flowering, after flowering, and veraison) were applied to Cabernet Sauvignon grapevines grown in Yantai (Shandong, China). Berry samples were harvested at maturation to determine the chemical composition, including total soluble solids, phenols, and volatiles. Leaf removal (particularly before flowering) could increase total soluble solids and phenols (anthocyanins, flavonols, and tartaric esters). Volatiles greatly changed in the different years, and leaf removal before flowering could increase the concentration of amino acid-derived volatiles and isoprene-derived volatiles compared with leaf removal after flowering or at veraison. This research provides a basis for further studies on optimizing Cabernet Sauvignon aroma and breeding in vineyards. [ABSTRACT FROM AUTHOR]

Eucommiae Folium (Duzhongye) is a traditional Chinese medicine with a long history of use in China. However, its quality‐marker in Chinese Pharmacopoeia is poorly defined nowadays. The study, therefore, conducted an ultra‐high‐performance liquid chromatography coupled with hybrid quadrupole‐orbitrap tandem mass spectrometry analysis to obtain accurate data. The obtained data were then compared with the authentic standards library using Xcalibur 4.1 software package and TraceFinder General Quan. Through the comparison, the study has putatively identified 26 bioactive compounds, which include 17 flavonoid derivatives (catechin, quercetin 3‐gentiobioside, quercetin 3‐O‐β‐D‐glucose‐7‐O‐β‐D‐gentiobioside, taxifolin, myricetin 3‐O‐galactoside, myricitrin, hyperoside, rutin, isoquercitrin, quercetin 3‐O‐β‐xylopyranoside, quercitrin, isorhamnetin 3‐O‐β‐D‐glucoside, quercetin, kaempferol, S‐eriodictyol, S‐naringenin, and phloridzin), four caffeoylquinic acids (neochlorogenic acid, chlorogenic acid, isochlorogenic acid A, and isochlorogenic acid C), two alkaloids (vincamine and jervine), one lignan (pinoresinol), one xanthone (cowaxanthone B), and one steroid (cholesteryl acetate). Of these, flavonoid isoquercitrin is recommended as the new and additional pharmacopeia quality‐marker candidate, which can not only overcome the unreliability of old quality‐marker but also recognize the possible counterfeit. [ABSTRACT FROM AUTHOR]

This research assessed the phenolic composition of Jussara pulp from the Brazilian states of Minas Gerais (MG) and Espírito Santo (ES) using HPLC-DAD-MS/MS. Seventeen anthocyanins were detected in fruits, derived from cyanidin, pelargonidin and peonidin. Among the non-anthocyanic phenolic compounds, flavonols (kaempferol, quercetin and isorhamnetin derivatives), flavan-3-ols (catechin, epicatechin, B-type procyanidins and unknown dimers) and resveratrol in its glycosylated form have been identified. Catechin (32.41-60.56 mg 100g-1) and epicatechin (18.86-40.92 mg 100g-1) were the main flavan-3-ols present in the fruits. The samples showed small concentrations of resveratrol glycosides (0.02-0.91 mg 100g-1). The analytical methodology used (HPLC-DAD-ESI-MS/MS) permitted the identification of newly reported compounds in this fruit. [ABSTRACT FROM AUTHOR]

Background: The curative effect of Cuscutae Semen (CS) could be adjusted after stir-frying, and it is difficult to distinguish between the raw CS and stir-fried processed Cuscutae Semen (SFCS) in clinical practice. Objective: The paper aims to establish the fingerprints of raw and fried Cuscutae Semen products by high-performance liquid chromatography (HPLC) so that the compounds in raw and stir-fried products could be analyzed qualitatively and quantitatively. At the same time, the chemometrics method was used to evaluate the difference between CS and SFCS to provide reference for the research of traditional Chinese medicine (TCM) CS. Method: The raw and SFCS products’ related substances were separated on a C18 column (250 mm 4.6 mm, 5 mm) maintained at 30 C (column temperature). The mobile phase comprised 0.1% formic acid aqueous solution (A) and acetonitrile (B), and a detection wavelength of 328 nm. The data were imported into statistical software for chemometric analysis. Results: The developed HPLC method exhibits good linearity and has good systematic applicability. The content of these 12 compounds in the samples was further determined and the data analyzed by chemometrics. The results showed that the composition of CS changed on heating, and HCA showed that CS and SFCS could be clearly distinguished. PCA showed that six components caused differences, namely neochlorogenic acid, cryptophyllogenic acid, caffeic acid, quercetin, isorhamnetin, and kaempferol. Conclusions: This study unequivocally establishes a chromatographic fingerprint method intended for the extensive analysis of raw and stir-fried processed CS, which could substantially enhance the quality control of CS and the rational development and utilization of TCM resources. Highlights: This method for the simultaneous quantification of multiple compounds in CS and SFCS revealed the components responsible for the differences between raw and processed products. This will provide support for quality control of this herbal medicine. [ABSTRACT FROM AUTHOR]

Green husks are the outer layer of walnut fruits. They form part of the agro-residues discarded away upon nut maturity in the walnut industry. Although it is not used, research studies show that green husk is a rich source of natural bioactive phytochemicals. A total of 83 individual phenolic compounds were identified in walnut husks, mainly consisting of naphthoquinones, flavonols, and hydroxycinnamic acids. There is no standard profile of phenolic compounds in walnuts; the quantity and quality of phenolic compounds vary by cultivar. Walnut extracts exhibit strong antioxidant activities and play an important role in the plant's defence mechanisms against diseases, attacking different plant organs. The study provides a review of total phenolic content and individual phenolic compounds identified in green husks of different walnut cultivars as documented in different studies. It also explores the role and application of green husks in various industries such as traditional medicine, textile, wood, leather, beverage, and agriculture. In addition, the effects of phenolic compounds on biotic and abiotic factors are also evaluated. [ABSTRACT FROM AUTHOR]

The consumption of foods that are rich in phenolic compounds has chemopreventive effects on many cancers, including breast cancer, ovarian cancer, and endometrial cancer. A wide spectrum of their health-promoting properties such as antioxidant, anti-inflammatory, and anticancer activities, has been demonstrated. This paper analyzes the mechanisms of the anticancer action of selected common flavonols, including kemferol, myricetin, quercetin, fisetin, galangin, isorhamnetin, and morin, in preclinical studies, with particular emphasis on in vitro studies in gynecological cancers and breast cancer. In the future, these compounds may find applications in the prevention and treatment of gynecological cancers and breast cancer, but this requires further, more advanced research. [ABSTRACT FROM AUTHOR]

In the last decades, Primula veris subsp. veris (roots and flowers) has been over harvested through legal and illegal ways in Greece, due to its extremely high commercial demand, as it is used in industry because of its well-known therapeutic properties. As ex situ cultures of the plant have been already developed, in the current comparative study, the herbal teas (infusions) from both flowers of cowslip growing wild in the Prespa Lake Park (NW Greece), and from ex situ propagated and cultivated plant material, have been investigated, with the ultimate goal of assessing them qualitatively. Furthermore, through classic phytochemical studies, the ten most abundant metabolites, belonging to the chemical categories of flavonol-glycosides and methoxy flavones, have been identified and structurally determined. The chemical profile of both infusions has been further analyzed through UHPLC-HRMS, showing that they show only light differences. The total phenolic content (TPC) of both studied samples (wild and ex situ cultivation), was determined by the Folin–Ciocalteau method, followed by an antioxidant activity assay though DPPH where, in both cases, wild plants exerted higher phenolic load and stronger antioxidative properties. According to the reported results, it could be proposed that the ex situ cultivated plant material could facilitate the mass production of plants and the sustainable cultivation of cowslip in the Greek mountains. [ABSTRACT FROM AUTHOR]

Aims of the study were the phytochemical investigation and chemical transformation of isolated compounds of medicinal plant listed in 'Ayurveda' like Dolichandrone atrovirens, endemic to Indian subcontinents. From chloroform extract of D. atrovirens four compounds; Ursolic acid (1), Maslinic acid (2), Lupeol (3), β-sitosterol (4) and from methanol extract five compounds; β-sitosterol-3-O-β-D-glucopyranoside (5), 10-O-trans-p-Methoxycinnamoylcatalpol (6), Kaempferol-3-O-β-D-glucopyranoside (7), 6-O-[6"(S)-hydroxy-2",6"dimethyl-2"(E)-7"-octadienoyl] catalpol (8) and Ixoside (9) were isolated. Ixoside was used for the semi-synthetic modification via azomethine ylide cycloaddition leading to novel spiro-oxindolo-pyrrolizidine adduct. The structures of novel adducts were elucidated by analysis of IR, MS and 1 D/2D NMR data. Furthermore, to confirm the chemo selection of only one double bond, we performed density functional theory (DFT) calculation, which confirms the chemo selectivity. In addition, in-silico ADME studies and atom-additive approach based on SASA was also examined for the molecules which suggest that they may be potential future candidates for drug discovery. [ABSTRACT FROM AUTHOR]

Camellia japonica is an underexplored medicinal plant with associated bioactivities. Innovative approaches are proposed in regard to the large-scale application of C. japonica, being one of the main routes for the extraction of phenolic compounds. The optimum conditions for the extraction of phenolic compounds from the flowers of C. japonica var. Eugenia de Montijo were determined using the response surface methodology (RSM). A five-level experimental design was carried out and analyzed via RSM using, as variables, temperature (T), time (t) and solvent (S), in the case of microwave-assisted extraction (MAE), and power (P), t and S in the case of ultrasound-assisted extraction (UAE). The compounds were identified using HPLC–MS–MS. Two responses were studied: the extraction yield and concentration of phenolic compounds. The results showed that the maximum yields (80%) were obtained at high temperatures and low times (180 °C, 5 min) when using MAE. Lower yields (56%) were obtained using UAE (optimal conditions 62% amplitude, 8 min, 39% acidified ethanol). The main family of phenolic compounds were flavonols. Moreover, the present study contributes to the valorization of underused flower species commonly present in the North-West region of Spain, by obtaining extracts rich in phenolic compounds that can be potentially applied as ingredients in different industrial fields. [ABSTRACT FROM AUTHOR]

Astringency and more generally mouthfeel perception are relevant to the overall quality of the wine. However, their origin and description are still uncertain and are constantly updating. Additionally, the terminology related to mouthfeel properties is expansive and extremely diversified, characterized by common traditional terms as well as novel recently adopted descriptors. In this context, this review evaluated the mention frequency of astringent subqualities and other mouthfeel attributes in the scientific literature of the last decades (2000–August 17, 2022). One hundred and twenty‐five scientific publications have been selected and classified based on wine typology, aim, and instrumental–sensorial methods adopted. Dry resulted as the most frequent astringent subquality (10% for red wines, 8.6% for white wines), while body—and related terms—is a common mouthfeel sensation for different wine types, although its concept is still vague. Alongside, promising analytical and instrumental techniques investigating and simulating the in‐mouth properties are discussed in detail, such as rheology for the viscosity and tribology for the lubrication loss, as well as the different approaches for the quantitative and qualitative evaluation of the interaction between salivary proteins and astringency markers. A focus on the phenolic compounds involved in the tactile perception was conducted, with tannins being the compounds conventionally found responsible for astringency. Nevertheless, other non‐tannic polyphenolic classes (i.e., flavonols, phenolic acids, anthocyanins, anthocyanin‐derivative pigments) as well as chemical–physical factors and the wine matrix (i.e., polysaccharides, mannoproteins, ethanol, glycerol, and pH) can also contribute to the wine in‐mouth sensory profile. An overview of mouthfeel perception, factors involved, and its vocabulary is useful for enologists and consumers. [ABSTRACT FROM AUTHOR]

Tea's biochemical compounds and flavor quality vary depending on its grade ranking. Dianhong Congou black tea (DCT) is a unique tea category produced using the large-leaf tea varieties from Yunnan, China. To date, the flavor characteristics and critical components of two grades of high-quality DCT, single-bud-grade DCT (BDCT), and special-grade DCT (SDCT) manufactured mainly with single buds and buds with one leaf, respectively, are far from clear. Herein, comparisons of two grades were performed by the integration of human sensory evaluation, an electronic tongue, chromatic differences, the quantification of major components, and metabolomics. The BDCT possessed a brisk, umami taste and a brighter infusion color, while the SDCT presented a comprehensive taste and redder liquor color. Quantification analysis showed that the levels of total polyphenols, catechins, and theaflavins (TFs) were significantly higher in the BDCT. Fifty-six different key compounds were screened by metabolomics, including catechins, flavone/flavonol glycosides, amino acids, phenolic acids, etc. Correlation analysis revealed that the sensory features of the BDCT and SDCT were attributed to their higher contents of catechins, TFs, theogallin, digalloylglucose, and accumulations of thearubigins (TRs), flavone/flavonol glycosides, and soluble sugars, respectively. This report is the first to focus on the comprehensive evaluation of the biochemical compositions and sensory characteristics of two grades of high-quality DCT, advancing the understanding of DCT from a multi-dimensional perspective. [ABSTRACT FROM AUTHOR]

Background: Huangqi Guizhi Wuwu decoction (HQGZWWD) has been used to treat and prevent deep vein thrombosis (DVT) in China. However, its potential mechanisms of action remain unclear. This study aimed to utilize network pharmacology and molecular docking technology to elucidate the molecular mechanisms of action of HQGZWWD in DVT. Methods: We identified the main chemical components of HQGZWWD by reviewing the literature and using a Traditional Chinese Medicine Systems Pharmacology (TCMSP) database. We used GeneCards and Online Mendelian Inheritance in Man databases to identify the targets of DVT. Herb-disease-gene-target networks using Cytascape 3.8.2 software; a protein–protein interaction (PPI) network was constructed by combining drug and disease targets on the STRING platform. Additionally, we conducted Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) enrichment analyses. Finally, molecular docking verification of active components and core protein targets was conducted. Results: A total of 64 potential targets related to DVT were identified in HQGZWWD, with 41 active components; quercetin, kaempferol, and beta-sitosterol were the most effective compounds. The PPI network analysis revealed that AKT1, IL1B, and IL6 were the most abundant proteins with the highest degree. GO analysis indicated that DVT treatment with HQGZWWD could involve the response to inorganic substances, positive regulation of phosphorylation, plasma membrane protein complexes, and signaling receptor regulator activity. KEGG analysis revealed that the signaling pathways included pathways in cancer, lipid and atherosclerosis, fluid shear stress and atherosclerosis, and the phosphatidylinositol 3-kinases/protein kinase B(PI3K-Akt) and mitogen-activated protein kinase (MAPK) signaling pathways. The molecular docking results indicated that quercetin, kaempferol, and beta-sitosterol exhibited strong binding affinities for AKT1, IL1B, and IL6. Conclusion: Our study suggests that AKT1, IL1B, and IL6 are promising targets for treating DVT with HQGZWWD. The active components of HQGZWWD likely responsible for its effectiveness against DVT are quercetin, kaempferol, and beta-sitosterol, they may inhibit platelet activation and endothelial cell apoptosis by regulating the PI3K/Akt and MAPK signaling pathways, slowing the progression of DVT. [ABSTRACT FROM AUTHOR]

Introduction: Apricot fruits are edible and serve as a source of medicinal compounds. Flavonols are important plant secondary metabolites that have antioxidant and antitumor effects and may promote cardiovascular health. Methods: The flavonoid content in three stages of the 'Kuijin' and the 'Katy' was observed, followed by the combination of metabolome and transcriptome analysis to explore the metabolic basis of flavonol synthesis. Results: The differences in the metabolite contents between stages (of the same cultivar) and between cultivars (at the same stage) revealed decreases in the flavonoid content as fruits developed (i.e., from 0.28 mg/g to 0.12 mg/g in 'Kuijin' and from 0.23 mg/g to 0.05 mg/g in 'Katy'). To decipher the regulation of flavonol synthesis in apricot (Prunus armeniaca L.), the metabolomes and transcriptomes of fruit pulp at three developmental stages of 'Kuijin' and the 'Katy' were analyzed. A total of 572 metabolites were detected in 'Kuijin' and the 'Katy' pulp, including 111 flavonoids. The higher flavonol content young 'Kuijin' fruits at 42 days after full bloom is mainly due to 10 types of flavonols. Three pairs of significant differences in flavonol content were identified. From these three comparison groups, three structural genes were strongly correlated with the levels of 10 types of flavonols (Pearson correlation coefficients > 0.8, p value < 0.05), including PARG09190, PARG15135, and PARG17939. The weighted gene coexpression network analysis showed that the turquoise module genes were highly correlated with flavonol contents (P < 0.01). There were 4897 genes in this module. Out of 4897 genes, 28 transcription factors are associated with 3 structural genes based on weight value. Two of the transcription factors are not only associated with PARG09190 but also with PARG15135, indicating their critical importance in the flavonols biosynthesis. The two TFs are PARG27864 and PARG10875. Discussion: These findings provide new insights into the biosynthesis of flavonols and may explain the significant differences in flavonoid content between the 'Kuijin' and the 'Katy' cultivars. Moreover, it will aid in genetic improvement to enhance the nutritional and health value of apricots. [ABSTRACT FROM AUTHOR]