(+/-)-Eriodictyol

1 Eriodictyon sp. 2 Kalmia sp. 3 Lycopus sp. 4 Mentha sp. 5 Phyllanthus sp. 6 Rhododendron sp. 7 Salix sp. 8 Sapium sp. 9 Silybum sp. 10 Thymus sp. 11 Verbascum sp.

Eriodictyol Inhibits the Production and Gene Expression of MUC5AC Mucin via the IkappaBalpha-NF-kappaB p65 Signaling Pathway in Airway Epithelial Cells.[Pubmed:34565719]

Biomol Ther (Seoul). 2021 Sep 27. pii: biomolther.2021.091.

In this study, we investigated whether eriodictyol exerts an effect on the production and gene expression of MUC5AC mucin in human pulmonary epithelial NCI-H292 cells. The cells were pretreated with eriodictyol for 30 min and then stimulated with phorbol 12-myristate 13-acetate (PMA) for 24 h. The effect of eriodictyol on PMA-induced nuclear factor kappa B (NF-kappaB) signaling pathway was also investigated. Eriodictyol suppressed the MUC5AC mucin production and gene expression induced by PMA via suppression of inhibitory kappa Balpha degradation and NF-kappaB p65 nuclear translocation. These results suggest that eriodictyol inhibits mucin gene expression and production in human airway epithelial cells via regulation of the NF-kappaB signaling pathway.

The use of alternative sweeteners (sucralose and stevia) in healthy soft-drink beverages, enhances the bioavailability of polyphenols relative to the classical caloric sucrose.[Pubmed:34530345]

Food Chem. 2021 Sep 4;370:131051.

The comparison of non-caloric sweeteners (stevia and sucralose) and sucrose, on the plasma concentration and cumulative effects of phenolic compounds, was achieved. A long-term intervention, consisting of the daily intake of 330 mL of healthy citrus-maqui soft drinks, for 60 days, by 138 healthy overweight adults, was followed. A total of 24 bioavailable metabolites derived from caffeic acid, 3,4-di-hydroxyphenylacetic acid, eriodictyol, homoeriodictyol, hippuric acid, naringenin, 2,4,6-tri-hydroxybenzaldehyde, and vanillic acid were detected in peripheral blood plasma. A similar augment of bioactive compounds in plasma concentrations were found for the three beverages, in the range 12.3% (day 0)- 85.3% (day 60), depending on the analyte considered. Due to this, the present study highlights sucralose and stevia as valuable alternatives to sucrose, providing and non-significantly different plasma concentration and cumulative effect in the plasma, thus contributing to prevent a diversity of metabolic disorders and health constraints.

Comparison of Antioxidant Properties of a Conjugate of Taxifolin with Glyoxylic Acid and Selected Flavonoids.[Pubmed:34439510]

Antioxidants (Basel). 2021 Aug 8;10(8). pii: antiox10081262.

It is known that flavonoids can react with toxic carbonyl compounds in the process of the storage, aging, and digestion of flavonoid-rich foods and beverages. However, the effect of these reactions on the antioxidant properties of the polyphenolic fraction and the properties of the resulting products remain poorly studied. The aim of the present work was to study the antioxidant activity of quercetin, taxifolin, catechin, eriodictyol, hesperetin, naringenin and a product of the condensation of taxifolin with glyoxylic acid, as well as to reveal the structure-activity relationship of these polyphenols. It was found that flavonoids containing the catechol moiety exhibited higher antioxidant activity than hesperetin and naringenin. The product showed the highest hydrogen peroxide scavenging activity, a lower metal-reducing and a higher iron-binding ability than catechol-containing flavonoids, and a lipid peroxidation inhibitory activity comparable with that of taxifolin. Thus, the condensation of flavonoids with toxic carbonyl compounds might lead to the formation of products exhibiting high antioxidant activity. Meanwhile, the conditions under which parent flavonoids and their products exhibit the maximal antioxidant activity may differ. The data suggest that the antioxidant profile of the polyphenolic fraction and bioavailability of polyphenols, carbonyl compounds, and metal ions may change when these reactions occur.

Discovery of natural 15-LOX small molecule inhibitors from Chinese herbal medicine using virtual Screening, biological evaluation and molecular dynamics studies.[Pubmed:34426159]

Bioorg Chem. 2021 Oct;115:105197.

Chinese herbal medicines (CHM) are frequently used to treat different types of inflammatory diseases and 15-Lipoxygenase (15-LOX) is a critical target enzyme for treating various inflammatory diseases. In this study, natural 15-LOX inhibitors were identified in CHM using an approach of virtual screening combined with the biological assays. First, an in-house Chinese medicine database containing 360 compounds was screened using a virtual screening approach based on pharmacophore and molecular docking to uncover several novel potential 15-LOX inhibitors. Secondly, the inhibitory effect of virtual screening hits against the 15-LOX enzyme was validated in an in vitro enzyme inhibition assay. Then, a tumor necrosis factor-alpha (TNF-alpha) release assay was carried out to explore the anti-inflammatory response of the active compounds. Furthermore, molecular dynamics (MD) simulation and binding free energy calculation were applied to analyze the process of inhibitors binding and also compared the mode of binding of the inhibitors by using the Molecular Mechanics-Generalized Born Surface Area (MM/GBSA) method. Finally, licochalcone B and eriodictyol were confirmed as inhibitors of the 15-LOX enzyme with IC50 values of 9.67 and 18.99 muM, respectively. In vitro cell-based assay showed that licochalcone B and eriodictyol inhibited the release of TNF-alpha factor in RAW264.7 cells stimulated by lipopolysaccharides (LPS) in a dose-dependent manner. Molecular dynamics and binding free energy analysis showed that the two 15-LOX-ligand systems immediately attained equilibrium with almost 1 A fluctuation, the calculated binding free energies were found around -18.89 and -12.96 kcal/mol for licochalcone B and eriodictyol, respectively. Thr412, Arg415, Val420, Thr429, Ile602 and Trp606 were the main amino acid residues for the inhibition of 15-LOX enzyme activity. The current study confirms that licochalcone B and eriodictyol are 15-LOX inhibitors and can suppress the release of the TNF-alpha factor in RAW264.7 cells stimulated by LPS, thus providing a basis for the follow-up research and development for 15-LOX inhibitors.

Metabolism of flavonoids and lignans by lactobacilli and bifidobacteria strains improves the nutritional properties of flaxseed-enriched beverages.[Pubmed:34399484]

Food Res Int. 2021 Sep;147:110488.

Flaxseed (Linum usitatissimum L.) is of interest as functional food because of the presence of compounds in its composition with potential health benefits, such as fatty acid omega-3, fiber, lignans and flavonoids. The bioactivity of lignans and flavonoids depends greatly on bacterial metabolism. Previously, lactobacilli and bifidobacteria strains were described to produce enterolignans and bioactive flavonoids (herbacetin, quercetin, quercetagetin, kaempferol, naringenin and eriodictyol) from flaxseed extracts and/or from secoisolariciresinol (SECO) in culture medium. In this work, cow's milk and soy beverage were supplemented with flaxseed extracts and fermented with selected lactobacilli and bifidobacteria strains. Lacticaseibacillus rhamnosus INIA P224, Limosilactobacillus mucosae INIA P508 and Lactiplantibacillus plantarum ESI 144 were capable of producing enterolactone (ENL) in both beverages supplemented with flaxseed, in addition to matairesinol and the flavonoids daidzein, genistein, glycitein, quercetin, naringenin, kaempferol and eriodictyol. On the other hand, Bifidobacterium breve INIA P367, Bifidobacterium pseudocatenulatum INIA P815 and Bifidobacterium pseudocatenulatum INIA P946 were able to produce quercetin, quercetagetin and high concentrations of herbacetin and SECO, in addition to pinoresinol, matairesinol, daidzein, genistein, naringenin, kaempferol and eriodictyol. The co-incubation of Lacticaseibacillus paracasei INIA P74 and Ligilactobacillus salivarius INIA P183 with Lactococcus lactis MG1363 harboring the food grade vector pLEB590.gly913, facilitated the production of ENL in soy beverage enriched with flaxseed. In this work, it is demonstrated how lactobacilli and bifidobacteria strains can improve the nutritional properties of flaxseed-enriched beverages, providing metabolites of great interest for human health.

Profiling the annual change of the neurobiological and antioxidant effects of five Origanum species in correlation with their phytochemical composition.[Pubmed:34399175]

Food Chem. 2021 Aug 5;368:130775.

The ethanol extracts of five Origanum species: O. majorana L., O. onites L., O. syriacum L., O. vulgare subsp. hirtum (Link) Ietsw., and O. vulgare subsp. viride (Boiss.) Hayek, collected annually (each month), were investigated for their cholinesterase inhibition and antioxidant effects. The phytochemical composition of a total of 60 extracts was assessed by HPLC-DAD-ESI/HRMS, revealing the presence of a total of 73 compounds. Possible correlation between the bioactivity and metabolite profiles during 12 months was monitored. Acetylcholinesterase (AChE) inhibitory activity was found to be the highest between April and November (50.29-75.95%, 200 mug/mL), while the highest inhibition towards butyrylcholinesterase (BChE) was observed for the extracts between April and October (71.68-88.97%). Aromadendrin showed good correlation with anti-AChE, anti-BChE and reducing power activities. Furthermore, molecular docking data with aromadendrin, caffeoylarbutin and eriodictyol indicated that caffeoylarbutin had the lowest binding energy against both enzymes.

Xuefu Zhuyu decoction improves asthma-induced asthenozoospermia based on network pharmacology and in vivo experiment.[Pubmed:34375006]

Andrologia. 2021 Aug 10:e14198.

This study aimed to verify that Xuefu Zhuyu decoction (XFZYD) can improve asthenozoospermia caused by asthma, and explore its potential mechanism. Ovalbumin solution is used to induce asthma rat models. Sperm concentration and motility are used to evaluate semen quality. Immunohistochemistry (IHC), Western blotting and real-time reverse transcription-quantitative polymerase chain reaction (RT-qPCR) are used to detect proteins and mRNA related to rat testis tissue. Haematoxylin and eosin (H&E) staining was used to observe changes in testicular tissues. Through network pharmacology, eriodictyol, 18-beta-glycyrrhetinic acid, naringenin, chrysin and Hispidulin were prominent active ingredients of XFZYD. We found that XFZYD regulates the expression levels of albumin (ALB), vascular endothelial growth factor A (VEGFA), interleukin 6 (IL-6) protein and mRNA, thereby improving the histopathological morphology of the testis, increasing the concentration and motility of spermatozoa. We suggest that future research can increase the detection of hormones and oxidative stress and other related indicators, so as to conduct more in-depth exploration.

Phytochemical Composition, Antioxidant, and Enzyme Inhibition Activities of Methanolic Extracts of Two Endemic Onosma Species.[Pubmed:34371578]

Plants (Basel). 2021 Jul 5;10(7). pii: plants10071373.

Onosma species have been used as a dye for hundreds of years due to their dark red pigments. These species have also been used by mankind in the treatment of various diseases since ancient times. This work analyzed the phytochemical composition in methanol extract of two endemic Onosma species (O. lycaonica and O. papillosa). Methanolic extract of these species varied in the content of flavonoids and phenolics. The flavonoids were found higher in O. papillosa [32.9 +/- 0.3 mg QEs (quercetin equivalent)/g extracts] while the phenolics were higher in O. lycaonica [43.5 +/- 1.5 mg GAEs (gallic acid equivalent)/g extracts]. ESI-MS/MS (electrospray ionization-mass spectrometry) revealed the presence of 25 compounds in O. lycaonica and 24 compounds in O. papillosa. The former was richer than the latter for apigenin, luteolin, eriodictyol, pinoresinol, apigenin 7-glucoside, rosmarinic acid, luteolin 7-glucoside, ferulic acid, vanillin, caffeic acid, 4-hydroxybenzoic acid, (+)-catechin3,4-dihydroxyphenylacetic acid. The O. papillosa exhibited low EC50 (1.90 +/- 0.07 mg/mL) which indicated its strong phosphomolybdenum scavenging activity as compared to O. lycaonica. However, the O. lycaonica showed low IC50 or EC50 for 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+), cupric reducing antioxidant power (CUPRAC), ferric reducing antioxidant power (FRAP) and ferrous ion chelating activity, as compared to O. papillosa. The results proved the presence of potent antioxidant compounds in O. lycaonica. Further, the plant extracts significantly varied for enzyme inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), but the plant extracts did not significantly differ for inhibition of alpha-glucosidase, alpha-amylase, and tyrosinase. Onosma species deserve further research towards developing novel drugs to treat oxidative diseases.

Flavonoids on diabetic nephropathy: advances and therapeutic opportunities.[Pubmed:34364389]

Chin Med. 2021 Aug 7;16(1):74.

With the advances in biomedical technologies, natural products have attracted substantial public attention in the area of drug discovery. Flavonoids are a class of active natural products with a wide range of pharmacological effects that are used for the treatment of several diseases, in particular chronic metabolic diseases. Diabetic nephropathy is a complication of diabetes with a particularly complicated pathological mechanism that affects at least 30% of diabetic patients and represents a great burden on public health. A large number of studies have shown that flavonoids can alleviate diabetic nephropathy. This review systematically summarizes the use of common flavonoids for the treatment of diabetic nephropathy. We found that flavonoids play a therapeutic role in diabetic nephropathy mainly by regulating oxidative stress and inflammation. Nrf-2/GSH, ROS production, HO-1, TGF-beta1 and AGEs/RAGE are involved in the process of oxidative stress regulation. Quercetin, apigenin, baicalin, luteolin, hesperidin, genistein, proanthocyanidin and eriodictyol were found to be capable of alleviating oxidative stress related to the aforementioned factors. Regarding inflammatory responses, IL-1, IL-6beta, TNF-alpha, SIRT1, NF-kappaB, and TGF-beta1/smad are thought to be essential. Quercetin, kaempferol, myricetin, rutin, genistein, proanthocyanidin and eriodictyol were confirmed to influence the above targets. As a result, flavonoids promote podocyte autophagy and inhibit the overactivity of RAAS by suppressing the upstream oxidative stress and inflammatory pathways, ultimately alleviating DN. The above results indicate that flavonoids are promising drugs for the treatment of diabetic nephropathy. However, due to deficiencies in the effect of flavonoids on metabolic processes and their lack of structural stability in the body, further research is required to address these issues.

Metabolomics combined with physiology and transcriptomics reveals how Citrus grandis leaves cope with copper-toxicity.[Pubmed:34352583]

Ecotoxicol Environ Saf. 2021 Oct 15;223:112579.

Limited data are available on metabolic responses of plants to copper (Cu)-toxicity. Firstly, we investigated Cu-toxic effects on metabolomics, the levels of free amino acids, NH4(+)-N, NO3(-)-N, total nitrogen, total soluble proteins, total phenolics, lignin, reduced glutathione (GSH) and malondialdehyde, and the activities of nitrogen-assimilatory enzymes in 'Shatian' pummelo (Citrus grandis) leaves. Then, a conjoint analysis of metabolomics, physiology and transcriptomics was performed. Herein, 59 upregulated [30 primary metabolites (PMs) and 29 secondary metabolites (SMs)] and 52 downregulated (31 PMs and 21 SMs) metabolites were identified in Cu-toxic leaves. The toxicity of Cu to leaves was related to the Cu-induced accumulation of NH4(+) and decrease of nitrogen assimilation. Metabolomics combined with physiology and transcriptomics revealed some adaptive responses of C. grandis leaves to Cu-toxicity, including (a) enhancing tryptophan metabolism and the levels of some amino acids and derivatives (tryptophan, phenylalanine, 5-hydroxy-l-tryptophan, 5-oxoproline and GSH); (b) increasing the accumulation of carbohydrates and alcohols and upregulating tricarboxylic acid cycle and the levels of some organic acids and derivatives (chlorogenic acid, quinic acid, d-tartaric acid and gallic acid o-hexoside); (c) reducing phospholipid (lysophosphatidylcholine and lysophosphatidylethanolamine) levels, increasing non-phosphate containing lipid [monoacylglycerol ester (acyl 18:2) isomer 1] levels, and inducing low-phosphate-responsive gene expression; and (d) triggering the biosynthesis of some chelators (total phenolics, lignin, l-trytamine, indole, eriodictyol C-hexoside, quercetin 5-O-malonylhexosyl-hexoside, N-caffeoyl agmatine, N'-p-coumaroyl agmatine, hydroxy-methoxycinnamate and protocatechuic acid o-glucoside) and vitamins and derivatives (nicotinic acid-hexoside, B1 and methyl nicotinate). Cu-induced upregulation of many antioxidants could not protect Cu-toxic leaves from oxidative damage. To conclude, our findings corroborated the hypothesis that extensive reprogramming of metabolites was carried out in Cu-toxic C. grandis leaves in order to cope with Cu-toxicity.

Eriodictyol attenuates dextran sodium sulphate-induced colitis in mice by regulating the sonic hedgehog signalling pathway.[Pubmed:34348563]

Pharm Biol. 2021 Dec;59(1):974-985.

CONTEXT: Eriodictyol (EDT) is a flavonoid with strong anti-inflammatory, anti-apoptotic, and antioxidant properties. OBJECTIVE: To investigate the protective effect and mechanism of EDT in ulcerative colitis (UC). MATERIALS AND METHODS: UC model was induced by 3% dextran sulphate sodium (DSS) solution for 7 days, meanwhile, EDT and Smoothened (Smo) inhibitor cyclopamine (Cyc) were intraperitoneally injected. In the first experiment, C57BL/6 mice divided into blank control, DSS, DSS + EDT (20 or 40 mg/kg) groups. In second experiment, added Cyc (5 mg/kg) and EDT + Cyc groups. All mice were sacrificed on day 8. Disease activity index (DAI), colon length and colon histology as well as MDA levels, SOD, and GSH-Px activities were measured. The expression of Sonic hedgehog (Shh), Patched, Smo, glioblastoma-1, zonula occludens-1 (ZO-1), occludin, cleaved caspase 3, Bax and Bcl-2 in colon was detected using RT-PCR and Western blotting. RESULTS: After EDT treatment, compared with the DSS group, DAI (2.33 +/- 0.516 vs. 3.67 +/- 0.516), colon shortening (5.27 +/- 0.476 vs. 4.53 +/- 0.528 cm) and histological score (6.67 +/- 1.211 vs. 12 +/- 1.265) was significantly decreased. EDT also reduced inflammation, oxidative stress and apoptosis in colon. Additionally, EDT increased the expression of the tight junction proteins ZO-1 (35%) and occludin (66.3%). Mechanistically, EDT upregulated the Shh signalling pathway. However, Cyc-mediated inhibition of the Shh pathway partially abolished the effects of EDT. DISCUSSION AND CONCLUSIONS: These results indicate EDT attenuates DSS-induced colitis by activating the Shh pathway. Further clinical trials are needed to demonstrate its efficacy on UC.

Infusion of aerial parts of Salvia chudaei Batt. & Trab. from Algeria: Chemical, toxicological and bioactivities characterization.[Pubmed:34320383]

J Ethnopharmacol. 2021 Nov 15;280:114455.

ETHNOPHARMACOLOGICAL RELEVANCE: Salvia chudaei Batt. & Trab. from Algeria is traditionally used to relieve several dysfunctions, including inflammatory and pain-related situations. AIM OF THE STUDY: This work aimed to confirm scientifically the referred properties. For that, the phenolic composition and antioxidant activity were evaluated as well as acute toxicity, anti-inflammatory and analgesic effects of different doses of the infusion of S. chudaei aerial parts. MATERIALS AND METHODS: Infusion of aerial parts of S. chudaei was prepared and screened for phenolic composition by generalized methods TPC and TFC then by LC-DAD-ESI/MSn. DPPH and FRAP were used to evaluate antioxidant activity. Using mice, acute toxicity, anti-inflammatory by carrageenan-induced paw edema, and analgesic by acetic acid-induced writhing and formalin-induced pain activities were tested. RESULTS: The infusion showed 2018 mg GAE/100g DW of phenolics and 1956 mg ECE/100g DW of flavonoids. Phenolic profile by LC-DAD-ESI/MSn revealed the presence of ten compounds: syringic acid hexoside derivative, kaempferol-O-diglucuronide, kaempferol-O-deoxyhexoside-hexoside, kaempferol-O-glucuronide, apigenin-O-diglucuronide, caffeic acid, 4-O-caffeoylquinic acid, eriodictyol-O-glucuronide, rosmarinic acid hexoside, and rosmarinic acid. This acid was the major compound representing 54% of the total content of the identified compounds and an absolute content of 18 mg/g of extract. Additionally, the infusion exhibited a good antioxidant activity (DPPH: 81 mumol TE/g DW, FRAP: 438 mumol FSE/g DW). By oral administration to mice, the infusion showed a significant (p<0.05) dose-dependent reduction of carrageenan-induced inflammation and inhibition of formalin-induced pain (late and early phase) and acetic acid-induced writhing compared with the control. On the other hand, infusion up to 8 g/kg b.w. showed no signs of toxicity or mortality. CONCLUSION: This study reveals, for the first time, that the infusion of the aerial parts of S. chudaei is not toxic in a single dose and has remarkable antioxidant, anti-inflammatory, and analgesic activities, supporting the use of this species in folk medicine.

Simultaneous Determination of 78 Compounds of Rhodiola rosea Extract by Supercritical CO2-Extraction and HPLC-ESI-MS/MS Spectrometry.[Pubmed:34306755]

Biochem Res Int. 2021 Jul 6;2021:9957490.

The plant Rhodiola rosea L. of family Crassulaceae was extracted using the supercritical CO2-extraction method. Several experimental conditions were investigated in the pressure range of 200-500 bar, with the used volume of cosolvent ethanol in the amount of 1% in the liquid phase at a temperature in the range of 31-70 degrees C. The most effective extraction conditions are pressure 350 bar and temperature 60 degrees C. The extracts were analyzed by HPLC with MS/MS identification. 78 target analytes were isolated from Rhodiola rosea (Russia) using a series of column chromatography and mass spectrometry experiments. The results of the analysis showed a spectrum of the main active ingredients Rh. rosea: salidroside, rhodiolosides (B and C), rhodiosin, luteolin, catechin, quercetin, quercitrin, herbacetin, sacranoside A, vimalin, and others. In addition to the reported metabolites, 29 metabolites were newly annotated in Rh. rosea. There were flavonols: dihydroquercetin, acacetin, mearnsetin, and taxifolin-O-pentoside; flavones: apigenin-O-hexoside derivative, tricetin trimethyl ether 7-O-hexosyl-hexoside, tricin 7-O-glucoronyl-O-hexoside, tricin O-pentoside, and tricin-O-dihexoside; flavanones: eriodictyol-7-O-glucoside; flavan-3-ols: gallocatechin, hydroxycinnamic acid caffeoylmalic acid, and di-O-caffeoylquinic acid; coumarins: esculetin; esculin: fraxin; and lignans: hinokinin, pinoresinol, L-ascorbic acid, glucaric acid, palmitic acid, and linolenic acid. The results of supercritical CO2-extraction from roots and rhizomes of Rh. rosea, in particular, indicate that the extract contained all biologically active components of the plant, as well as inert mixtures of extracted compositions.

A DFT study on OH radical scavenging activities of eriodictyol, Isosakuranetin and pinocembrin.[Pubmed:34286668]

J Biomol Struct Dyn. 2021 Jul 21:1-10.

Flavonoids are natural compounds with antioxidant properties that have positive effects on human health, which reduce toxic effects of reactive oxygen species (ROS) and partially oxidative damage. In the work, the density functional theory (DFT/BMK) calculations were performed for antioxidant activity evaluation of pinocembrin (P), isosakuranetin (I) and eriodictyol (E). Four main mechanisms were examined: hydrogen atom transfer (HAT), radical adduct formation (RAF), single electron transfer-proton transfer (SET-PT) and Sequential proton loss electron transfer (SPLET). HAT and SPLET are thermodynamically the most probable process in gas phase and water. The three flavonoids examined + *OH HAT and RAF mechanisms for each possible location were investigated theoretically for the first time. The results were discussed by considering thermodynamic, kinetic and structural data of various reaction paths using IRC approach.Communicated by Ramaswamy H. Sarma.

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