Quercetin 3,4'-diglucoside

Antiallergic activities of shallot (Allium ascalonicum L.) and its therapeutic effects in allergic rhinitis.[Pubmed:31421664]

Asian Pac J Allergy Immunol. 2019 Aug 18.

BACKGROUND: Onion has antiallergic activity but lack of evidence for shallot. OBJECTIVES: To determine whether shallot owns similar antiallergic activity to onion and its therapeutic effects in allergic rhinitis when added to standard treatment METHODS: In-vitro beta-hexosaminidase inhibitory activities of shallot was compared with onion on RBL-2H3 cells. In clinical study, a randomized, double-blind, placebo-controlled trial was performed. Sixteen AR patients were randomized equally into the controls who received cetirizine 10 mg once daily and placebo capsules for 4 weeks, and the treatment who received 3g of oral shallot per day (equivalent to 1 (1/2) bulbs) and cetirizine. Visual analog scores of overall symptoms (VAS), total nasal and ocular symptom scores (TNSS and TOSS), nasal airway resistance (NAR), and adverse events were assessed. RESULTS: Shallot extract at 200 mug/mL had an average beta-hexosaminidase inhibition rate of 97% while onion extract had 73%. HPLC chromatograms (lambda = 290nm) of both plants showed nearly identical patterns of quercetin compounds, such as quercetin 3,4'-diglucoside, quercetin 4'-glucoside, and quercetin. After 4-week of treatment, 62.5% of patients in shallot group and 37.5% of patients in control group showed improvement of post-treatment VAS. TNSS were significantly reduced in both groups, however no difference between groups (P = 0.18). TOSS were significantly improved only in the shallot group (P = 0.01). Adverse events from shallot were not different from placebo. CONCLUSIONS: Shallot had antiallergic activity and similar quercetin compounds to onion. The shallot oral supplement and cetirizine was shown to improve the overall AR symptoms more than cetirizine alone.

Identification of compounds that inhibit the binding of Keap1a/Keap1b Kelch DGR domain with Nrf2 ETGE/DLG motifs in zebrafish.[Pubmed:30861618]

Basic Clin Pharmacol Toxicol. 2019 Sep;125(3):259-270.

The Keap1-Nrf2-ARE system serves as a premier defence mechanism to curb oxidative stress, which remains as one of the major causes of ageing and pathogenesis in various diseases. Nrf2 is the principal master regulator of the cellular defence system, and its activation remains the prospective therapeutic approach against chronic diseases. One of the recent strategies is to disrupt Keap1-Nrf2 protein-protein interaction (PPI) that alters the docking of Keap1 with Nrf2 by compounds occupying a position in the Keap1 blocking the interface with Nrf2. In this study, we made an attempt to identify the compounds with anticancer, antioxidant and anti-inflammatory properties to disrupt Keap1a/b-Nrf2 PPI through in silico molecular docking in zebrafish. The phylogenetic analysis of Keap1 proteins revealed the existence of orthologous Keap1-Nrf2-ARE system in lower vertebrates that includes zebrafish. The DGR domains of zebrafish Keap1a and Keap1b were modelled with Modeller 9.19 using Keap1 of Mus musculus (PDB ID:5CGJ) as template. Based on the docking calculations, top hit compounds were identified to disrupt both Keap1a and Keap1b interaction with Nrf2 which include quercetin 3,4'-diglucoside, flavin adenine dinucleotide disodium salt hydrate, salvianolic acid A, tunicamycin and esculin. The LC50 of esculin in 3 dpf zebrafish larvae is 5 mmol/L, and the qRT-PCR results showed that esculin significantly increased the transcription of Nrf2 target genes-Gstpi, Nqo1, Hmox1a and Prdx1 in 3 dpf zebrafish larvae. These potential hits could serve as safer Nrf2 activators due to their non-covalent disruption of Keap1-Nrf2 PPI and be developed into efficacious preventive/therapeutic agents for various diseases.

Quantitative metabolite profiling of edible onion species by NMR and HPLC-MS.[Pubmed:25038704]

Food Chem. 2014 Dec 15;165:499-505.

Allium genus is a treasure trove of valuable bioactive compounds with potentially therapeutically important properties. This work utilises HPLC-MS and a constrained total-line-shape (CTLS) approach applied to (1)H NMR spectra to quantify metabolites present in onion species to reveal important inter-species differences. Extensive differences were detected between the sugar concentrations in onion species. Yellow onion contained the highest and red onion the lowest amounts of amino acids. The main flavonol-glucosides were quercetin 3,4'-diglucoside and quercetin 4'-glucoside. In general, the levels of flavonols were, higher in yellow onions than in red onions, and garlic and leek contained a lower amount of flavonols than the other Allium species. Our results highlight how (1)H NMR together with HPLC-MS can be useful in the quantification and the identification of the most abundant metabolites, representing an efficient means to pinpoint important functional food ingredients from Allium species.

Hyaluronidase inhibiting activity and radical scavenging potential of flavonols in processed onion.[Pubmed:23656415]

J Agric Food Chem. 2013 May 22;61(20):4862-72.

The flavonol content and anti-inflammatory and antioxidant activities of onion treated by high-pressure processing (HPP) and HPP combined with freeze-drying and pulverization (HPP-FD-P) were evaluated. Allium cepa L. var. cepa, 'Recas' was treated at T1 (200 MPa/25 degrees C/5 min), T2 (400 MPa/25 degrees C/5 min), and T3 (600 MPa/25 degrees C/5 min). After treatment, HP-treated and untreated samples were frozen (diced onion, HP-treated). Subsequently, part of the diced samples was freeze-dried and pulverized (pulverized onion, HP-treated and freeze-dried). Flavonol content and anti-inflammatory and antioxidant activities (hyaluronidase inhibiting activity, NO(*), ABTS(*+), and DPPH(*) scavenging capacity, ferric reducing antioxidant power, and antioxidative capacity by photochemiluminescence) were measured in nonhydrolyzed and hydrolyzed extracts. Hydrolysis was carried out in order to evaluate the effect of HPP and HPP-FD-P on both anti-inflammatory and antioxidant activities of extracts mainly containing aglycone forms. HPP-FD-P increased quercetin 3,4'-diglucoside, quercetin 4'-glucoside, quercetin 3-glucoside, and isorhamnetin 3,4'-diglucoside extractability. The present study suggests that HPP (especially treatment at 400 MPa) and HPP-FD-P may be of benefit for obtaining functional ingredients from onion, as suggested by increased NO(*) scavenging capacity and maintenance of the antioxidant activity mainly in hydrolyzed extracts.

Physicochemical characteristics of rapidly dried onion powder and its anti-atherogenic effect on rats fed high-fat diet.[Pubmed:25212303]

Food Chem. 2011 Dec 1;129(3):810-5.

Rapidly dried onion (Allium cepa L. cv. Momiji No. 3) powder (OP) prepared from the outer layers (from second to fourth scale leaves from the surface) of onion bulbs was analysed for its quercetin and polyuronide contents, the effects of enzymatic treatment and the anti-atherogenic effect on rats fed a high-fat diet. Quercetin 4'-glucoside (50%), free quercetin (30%) and quercetin 3,4'-diglucoside (20%) were identified as quercetin derivatives, and boiling-water extraction was effective in extracting these compounds. OP contained 12.9% of polyuronides, the basic skeleton of pectin. Enzymatic degradation (cellulase and pectinase, 50 degrees C for 12h, pH 6.0) of OP was effective in obtaining a slurry of smaller particle sizes. The free quercetin increased and the glucosides decreased with enzyme treatment. In Wistar rats fed an OP-added high-fat diet, the total cholesterol, HDL-cholesterol and triglyceride concentrations were not significantly different from the rats fed a high-fat diet without OP. However, the atherogenic index (AI) of Wistar rats fed an OP-added high-fat diet was lower (AI=3.3) than rats fed the diet without OP (AI=4.1). The incremental elastic modulus (IEM) of the aorta from rats fed the OP-added diet was also significantly lower than that of the rats fed the diet without OP. The AI and IEM values of the rats fed the OP-added diet were quite similar to the values of rats fed the diet without OP but were allowed spontaneous exercise. These results suggest that OP intake is effective for decreasing the risk of arteriosclerosis.