Profiling and quantifying quercetin glucosides in onion (Allium cepa L.) varieties using capillary zone electrophoresis and high performance liquid chromatography

There is increasing evidence that flavonols demonstrate beneficial properties for human health. Quercetin is the major flavonol present in onion (Allium cepa cv) and is present predominantly as quercetin 3,4′-diglucoside and quercetin 4′-monoglucoside. These compounds are known to be potent free radical scavengers and antioxidants, and are considered to be protective against cardiovascular disease. Analysis for the presence of these compounds has therefore become more important. Robust capillary zone electrophoresis and high performance liquid chromatography procedures were developed for profiling and quantifying the levels of quercetin 3,4′-diglucoside and quercetin 4′-monoglucoside in 70% methanol/water extracts of six different onion varieties available in Victoria, Australia. Quercetin 3,4′-diglucoside, which is not commercially available as a reference standard, was isolated from freeze-dried onion powder by preparative high performance liquid chromatography and used to quantify the levels in the onion extracts. Significant differences in the levels and ratios of the two compounds were seen between red, brown and white onion varieties (e.g. ‘Redwing’; quercetin 3,4′-diglucoside 191 mg/100 g DW, quercetin 4′-monoglucoside 85 mg/100 g DW; ‘Cream Gold’, quercetin 3,4′-diglucoside 153 mg/100 g DW, quercetin 4′-monoglucoside 58 mg/100 g DW, ‘Spanish white’; quercetin 3,4′-diglucoside <1 mg/100 g DW, quercetin 4′-monoglucoside <1 mg/100 g DW).     

Onion high-pressure processing: Flavonol content and antioxidant activity

Onion flavonol content and antioxidant activity have been related to human health promoting effects. Quercetin and quercetin glucosides (quercetin-4′-glucoside and quercetin-3,4′-diglucoside) have been reported the main onion flavonols in recent literature. Impact of combined treatments of high-pressure processing (HPP) and temperature on onion nutritional attributes has been scarcely studied.Our study aimed to investigate the impact of HPP technology combined with temperature on onion (Allium cepa L. var. cepa, ‘Grano de Oro’) total phenol content, flavonol content, and antioxidant capacity. The experimental design comprised a response surface methodology according to a central composite face-centred design. The variable ranges were 100-400 MPa (pressure) and 5-50 °C (temperature), time was set up constant to 5 min.Response surfaces of onion total quercetin, quercetin-4′-glucoside, and quercetin-3,4′-diglucoside content showed a similar pattern. The application of low temperature (5 °C) combined with pressures of 100 and 400 MPa triggered to a better extraction of these flavonols among the treatments analysed. Response surface of the EC₅₀ antioxidant parameter as a function of pressure and temperature showed a clear trend towards an increase in onion antioxidant activity when applying pressures from 100 to 400 MPa. Four hundred megapascals/5 °C-processed onion showed an approximately 33% higher quercetin-4′-glucoside content compared with the untreated onion, and maintained the antioxidant activity of the untreated onion.     

桑椹籽油的降脂作用研究注

目的研究桑椹籽油的降脂作用;方法普通基础饲料加10%猪油、l%胆固醇,0.5%胆酸钠组成高脂饲料,高脂饲料中添加6%的桑椹籽油饲喂Wistar大鼠(桑籽油组)4周后与单饲高脂饲料的大鼠(高脂组)对比血脂和肝脂水平.结果与高脂组比较,桑籽油组大鼠血清和肝脏的胆固醇、甘油三酯含量均显著降低(P＜0.01),血清低密度脂蛋白胆固醇和致动脉硬化指数也明显下降(P＜0.01),而高密度脂蛋白胆固醇和抗动脉硬化指数显著升高(P＜0.01);结论桑椹籽油具有显著的降脂、抗动脉粥样硬化作用.     

Flavonol glucosides in Allium species: A comparative study by means of HPLC–DAD–ESI-MS–MS

Cultivars and consumption typologies of some Allium species can significantly vary from a chemical point of view and even small differences can be important for their characterization and differentiation. Bulbs of three varieties and four consumption typologies of onion (Allium cepa L.) and two varieties of shallot (Allium ascalonicum Hort.) were subjected to HPLC–DAD–ESI-MS–MS analysis. Seven flavonol glucosides were identified in all the samples, two of which, quercetin 3,4′-diglucoside and quercetin 4′-glucoside, represent about the 90% of the overall contents. Cultivars and consumption typologies of the Allium species under study show significant differences in flavonol contents, from the very low quantity of antioxidant compounds in white onion, about 7 mg/kg against 600–700 mg/kg that were found in red and gold varieties, to the enormous content of flavonols that are present in onions of prompt consumption, where quercetin 4′-glucoside exceeds 1 g/kg and quercetin 3-glucoside is present in a ratio higher then 10:1 with respect to its value in the other onion typologies. Shallots are very rich in the two major flavonols.     

Distribution of quercetin-3,4′-O-diglucoside,quercetin-4′-O-monoglucoside,and quercetin in different parts of the onion bulb (Allium cepa L.) influenced by genotype

Flavonoids have gained much attention because of their proposed positive effects for human health. Onions are a rich source of flavonoids, consisting mainly of the major flavonols quercetin-3,4′-O-diglucoside (QDG) and quercetin-4′-O-monoglucoside (QMG) in the bulb and the aglycone quercetin in the outer scales. In this study, distribution of these three flavonoids was determined in 16 onion cultivars (Allium cepa) using HPLC–DAD. Three different parts of the onion bulb, the inner layers, the middle layers and the outer scales were analysed. The analysis showed varietal differences in the selected onion cultivars. The cultivars with the highest total flavonoid content were the red skinned ‘Red Baron’ and the yellow skinned cultivars ‘Ailsa Craig’ and ‘Prilep’. The distribution of the total flavonoid content in the different parts of the onion bulb showed the following order: middle layers > outer scales > inner layers. In the inner layers QDG was the major flavonoid, while in the middle layers QDG and QMG were in equal amounts. In the outer scales quercetin was the major flavonoid prior to QMG.     

Dose dependent effects of lycopene enriched tomato-wine on liver and adipose tissue in high-fat diet fed rats

The functional effects of tomato-wine with varying lycopene content on high-fat diet (HFD) fed rats are unknown. Male Sprague–Dawley rats (n = 50) were randomly divided into five groups and fed a HFD (35% kcal fat) with ethanol (7.2% kcal alcohol), tomato-wine with varying lycopene content (0.425, 1.140 or 2.045 mg% lycopene) or an isocaloric control diet for 6 weeks. Morphological, toxicological and metabolic analysis was conducted in liver, adipose, plasma and faeces. Body weight gain, adipose and liver weight was reduced in HFD fed rats administered tomato-wine with varying lycopene content, although tomato-wine with higher lycopene was more effective. The anti-obesity effect of tomato wine appears to be partially mediated through the inhibition of fatty acid synthesis and lipid droplet formation. Furthermore, tomato-wine appears to have an anti-atherogenic effect via augmentation of plasma HDL-C levels. The present findings suggest tomato-wine fortified with lycopene may be an effective anti-obesity agent.     

Subcritical water extraction of flavonol quercetin from onion skin

Subcritical water could be an excellent alternative to organic solvent as a medium for extracting flavonol quercetin, due to its temperature-dependent selectivity, safety, efficiency of recovery, and lower cost. This study investigated the application of subcritical water extraction (SWE) of quercetin from onion skin and evaluated the effect of key operation conditions by varying the temperature (100-190 °C), extraction time (5-30 min), and mixture ratio of onion skin and diatomaceous earth (DE) (0.5:3.5-2:2) under high pressure (90-131 bar). The maximum yield of quercetin (16.29 ± 0.75 mg/g onion skin) was obtained at extraction temperature of 165 °C, extraction time of 15 min, mixture ratio of 1.5:2.5 for onion skin and DE. The SWE was compared with three conventional extraction methods in terms of the efficiency. The quercetin yield by SWE was over eight-, six-, and fourfold greater than those obtained using the ethanol, methanol, and water-at-boiling-point extraction methods, respectively.     

Effect of soybean oligosaccharides on blood lipid,glucose levels and antioxidant enzymes activity in high fat rats

The effect of soybean oligosaccharides on blood lipid levels and oxidative stress in rats fed on high-fat diet was investigated. Rats were divided into five groups of 10 animals each. The high-fat group received a high-fat diet containing 18% (w/w) lipid in the diet (36% of total energy). Animals allocated to the soybean oligosaccharides-treatment groups (I, II and III) received the high-fat diet and orally fed with soybean oligosaccharides at a single dose of 150, 300 and 450 mg/kg body weight, respectively. Control rats received basic diet. Results showed that soybean oligosaccharides significantly reduced abnormal blood glucose, lipid level and oxidative stress in animal models at all doses examined. Soybean oligosaccharides were able to reduce oxidative stress and improve abnormal blood lipid levels induced by high-fat diets. In summary, the present study may be important for reverse cardio-cerebrovascular disease.     

Iron bioavailability from ferric pyrophosphate in rats fed with fructan-containing yacon (Smallanthus sonchifolius) flour

The effects of inulin-type fructans (ITF)-containing yacon flour (YF) on Fe bioavailability from ferric pyrophosphate (FP) were evaluated in Fe-deficient rats using the Hb repletion efficiency (HRE) assay. Weanling male Wistar rats were fed a low-Fe diet (12 mg/kg) for 15 days followed by 2 weeks of Fe repletion with diets providing 35 mg Fe/kg as either ferrous sulphate (FS) or FP, supplemented with 7.5% ITF as either YF or Raftilose (RAF), a purified ITF. ITF increased caecal fermentation, whereas YF was more butyrogenic than RAF. ITF improved HRE in FP-fed rats, and those fed YF had a higher relative biological value compared with those fed FP and RAF. Liver Fe was increased by ITF, but only YF led to values similar to those in the FS group. It is observed that ITF increased caecal fermentation and Fe bioavailability. These effects were more pronounced when YF was the ITF source.     

Reduction of lipid accumulation in white adipose tissues by Cassia tora (Leguminosae) seed extract is associated with AMPK activation

Natural herbal medications may be one answer to the worldwide epidemic of obesity. This study examines the effects of Cassia seed ethanol extract (CSEE) upon lipid accumulation in white adipose tissue (WAT). CSEE exhibited a significant concentration-dependent decrease in the intracellular accumulation of trigycerides in 3T3-L1 adipocytes. After being fed a high-fat diet (HFD) for 2 weeks, rats were fed CSEE (100, 200 or 300 mg/kg) once daily for 8 weeks. CSEE caused dose-related reductions in body weight gain (as well as plasma lipid levels and epididymal WAT sizes in HFD-fed rats). CSEE enhanced the phosphorylation of AMP-activated protein kinase (AMPK) and its primary downstream targeting enzyme, acetyl-CoA carboxylase, up-regulated gene expression of carnitine palmitoyl transferase 1, and down-regulated sterol regulatory element-binding protein 1 and fatty acid synthase protein levels in epididymal WAT of HFD-fed rats. CSEE could attenuate lipid accumulation in WAT via AMPK signaling pathway activation.     

Comparison between low-dose,high-sort and high-dose,low-sort semen on conception and calf sex ratio in Jersey heifers and cows

The objective of this clinical trial was to compare conception and newborn calf sex ratios among Jersey heifers and lactating cows inseminated with either standard sex-sorted semen (low-dose, high-sort; LDHS) containing 2.1 × 10⁶ sorted sperm at 90% purity or high-dose, low-sort (HDLS) semen containing 10 × 10⁶ sorted sperm at 75% purity. After a specified voluntary waiting period (VWP), female subjects, consisting of nulliparous heifers (VWP 10 mo of age) and lactating cows (VWP 50 d in milk), received their first service and were systematically allocated to each treatment group in the order in which they presented for artificial insemination (AI). Females were bred to the same sire and type of sex-sorted semen for up to 2 additional services. Animals that were not pregnant after 3 breeding attempts were excluded. A total of 1,846 services were performed on 1,011 eligible females (LDHS; n = 494, HDLS; n = 517), which consisted of 516 nulliparous heifers and 495 lactating cows. Study groups were comparable with respect to the mean age at first AI for nulliparous heifers and the mean days in milk at first AI for parous cows. Insemination with HDLS semen did not result in a higher proportion of pregnancies per AI (P/AI) compared with LDHS semen for either nulliparous heifers (P/AI = 43 vs. 38%) or parous cows (P/AI = 47 vs. 43%). Insemination of nulliparous heifers using HDLS resulted in a lower proportion of newborn female calves compared with those bred to LDHS (76% vs. 87%). Similarly, lactating cows bred to HDLS gave birth to a lower proportion of newborn female calves compared with those bred to LDHS (79 vs. 90%). The odds ratio for a female calf to be born to an animal inseminated with HDLS compared with LDHS was 0.32 for nulliparous heifers and 0.19 for parous cows. Overall, the use of HDLS resulted in fewer females compared with LDHS, which may be explained by the lower concentration of X-bearing spermatozoa in HDLS compared with LDHS.     

Effects of quercetin metabolites on the enhancing effect of β-carotene on DNA damage and cytochrome P1A1/2 expression in benzo[a]pyrene-exposed A549 cells

A549 cells were pre-incubated with β-carotene (BC) alone or in combination with quercetin or three major quercetin metabolites in human plasma, quercetin 3-glucuronide (Q3G), quercetin 3′-sulphate (Q3′S) and isorhamnetin, followed by incubation with benzo[a]pyrene (BaP), to investigate the effects of these compounds on the BaP-induced harmful effects of BC. All the quercetin metabolites at 10 μM inhibited BaP + BC-induced cell death. Q3′S, Q3G and isorhamnetin also significantly decreased BaP ± BC-induced DNA damage by 64%, 60% and 24%, respectively. In a similar order, these compounds suppressed BaP + BC-induced cytochrome P450 (CYP)1A1/1A2 expression by 10–50%. Q3G and Q3′S significantly decreased the intracellular reactive oxygen species formation induced by BaP + BC; however, Q3G had the best effect on decreasing the loss of BC induced by Fe/NTA. The combined effects of quercetin metabolites were additive. This study indicates that quercetin metabolites decrease the BaP-induced harmful effect of β-carotene in A549 cells by downregulating the expression of CYP1A1/1A2, at least in part.     

Pressurised hot water extraction with on-line particle formation by supercritical fluid technology

In this work, an on-line process for pressurised hot water extraction (PHWE) of antioxidants from plants as well as drying of the extract in one step by particle formation based on the use of supercritical carbon dioxide (SC-CO₂) has been developed. This process has been called WEPO®, water extraction and particle formation on-line. With this process, dried extracts from onion with the same composition of quercetin derivatives as non-dried extracts have been obtained as a fine powder with spherical particles from 250 nm to 4 μm in diameter. The major compounds present in the extract were quercetin-3,4′-diglucoside, quercetin-4′-glucoside and quercetin. An auxiliary inert gas (hot N₂) was used to enhance the drying process. Parameters such as temperature (120 °C), SC-CO₂ and N₂ pressures (80 and 12.5 bar, respectively) and flow rate of SC-CO₂ (10 ml/min), have been settled by trial-and-error in order to achieve a fine and constant spray formation. Water content, size and morphology, antioxidant capacity and quercetin content of the particles were studied to evaluate the efficiency of the WEPO process. Results were compared with the ones from extracts obtained by continuous flow PHWE followed by freeze-drying. Results showed that both processes gave similar results in terms of antioxidant capacity, concentration of quercetin derivatives and water content, while only WEPO was able to produce defined spherical particles smaller than 4 μm.     

Quercetin content in some food and herbal samples

Quercetin is a typical flavonoid ubiquitously present in vegetables and fruits, and its antioxidant effect is implied to be helpful for human health. The efficiency of extraction process and acidic hydrolysis parameters for HPLC analysis of quercetin present in glycosides and aglycone forms was investigated. Hydrolysis for 5 min in the presence of 2.8 M HCl as well as for 10 min with 1.1 M HCl efficiently released quercetin from rutin. The method developed in this study was applied for quantitative determination of quercetin in some food (onion, apple) and herbal (Hypericum perforatum and Sambucus nigra) products.     

Effects of xyloglucan with the partial removal of galactose on plasma lipid concentration

Xyloglucan is a component of the cell walls of higher plants that has been used as a thickener or stabilizer in the food industry in Japan and other Asian countries. Xyloglucan from which side-chain galactose has been partially removed or ‘trimmed’ by β-galactosidase (GXG-TG) shows heat-induced reversible gelation, and reverts to sol upon cooling. Xyloglucan is not digested by human digestive enzymes and acts as a dietary fiber. The effects of xyloglucan from which galactose has been partially removed on plasma lipid concentration in rats was investigated. Male Wistar rats (4 weeks old) were fed a high-fat diet (corn oil or lard) for 28 days (control) and other groups were given a high-fat diet (corn oil or lard) containing GXG-TG (5%, replacing cellulose). GXG-TG significantly reduced total cholesterol, β-lipoprotein, total lipid and phospholipid compared to a high-fat diet with corn oil. GXG-TG significantly reduced total cholesterol, β-lipoprotein, total lipid, phospholipid and adipose tissue weight compared to a high-fat diet with lard. These results indicated that the intake of GXG-TG improves lipid metabolism in rats, similar to that of the intact xyloglucan.     

湿热处理多孔玉米淀粉对大鼠脂质代谢的影响

目的：探讨湿热处理多孔玉米淀粉对大鼠脂质代谢的影响。方法：32 只雌性Sprague-Dawley（SD）大鼠随机分为4 组,其中1 组为对照组饲喂基础饲料,另外3 组为高脂组,分别为高脂空白组、多孔淀粉组（porousstarch,PS）和湿热处理多孔淀粉组（heat moisture treatment starch,HTMPS）,饲喂基础饲料,适应1 周后,对照组饲喂基础饲料,高脂组分别饲喂相应高脂饲料。饲喂4 周后解剖,检测大鼠血脂、肝脂及小肠和粪便中胆汁酸等指标。结果：饲喂多孔淀粉和湿热处理多孔淀粉组大鼠血清总胆固醇（total cholesterol,TC）、甘油三酯（triglyceride,TG）、非高密度脂蛋白胆固醇（non-high-density lipoprotein cholesterol,non-HDL-C）、抗动脉硬化指数（atherosclerosis index,AI）、甘油三酯/高密度脂蛋白胆固醇（TG/HDL-C）、肝脏TC、肝脏总TC和腹部脂肪含量显著下降（P＜0.05）,粪便中粪醇、胆固醇等中性固醇排泄量增加,粪便中胆汁酸排泄量显著增加（P＜0.05）。PS组与HTMPS组相比,大鼠血浆中TC、AI、腹部脂肪含量、肝脏总脂肪含量较低,粪便中胆汁酸及小肠内容物中胆汁酸较高。结论：多孔淀粉降血脂降胆固醇效果优于湿热处理多孔玉米淀粉,可降低高脂饮食造成的高脂血症风险,对预防心血管疾病有一定的作用。     

Anti-hyperlipidaemic and antioxidant effects of turmeric oil in hyperlipidaemic rats

This study was to evaluate the anti-hyperlipidaemic and antioxidant effects of turmeric oil (TO), the supercritical fluid extract from turmeric, in hyperlipidaemic rats induced by a high-fat diet. TO significantly decreased (p < 0.05) the levels of serum total cholesterol, low-density lipoprotein cholesterol, triglyceride, and free fatty acid and increased (p < 0.05) that of high-density lipoprotein cholesterol in this model. It also markedly elevated (p < 0.05) the activities of superoxide dismutase and glutathione peroxidase and lowered (p < 0.05) maleic dialdehyde activity, to suppress oxidative reactions. Besides, histological morphology examination showed that TO prevented the damage of liver tissues induced by high-fat diet. Thus, the findings indicate that TO might provide protection against cardiovascular diseases.     

Solubility and solution thermodynamic properties of quercetin and quercetin dihydrate in subcritical water

Fundamental physicochemical data is required for the design and optimization of food engineering processes, such as extraction. Flavonoids are present in natural products such as grapes and have numerous health benefits particularly with respect to their reported antioxidant properties. Such flavonoid compounds can be extracted from these natural products using a variety of solvents, among them water. In this study, the aqueous solubilities of 3,3′,4′,5,7-pentahydroxyflavone (quercetin) and its dihydrate were measured at temperatures between 25 and 140 °C using a continuous flow type apparatus. The flow rate of subcritical water was studied at 0.1, 0.2 and 0.5 mL/min to study its effect on quercetin solubility and thermal degradation at temperatures greater than 100 °C. The aqueous solubility of anhydrous quercetin varied from 0.00215 g/L at 25 °C to 0.665 g/L at 140 °C and that of quercetin dihydrate varied from 0.00263 g/L at 25 °C to 1.49 g/L at 140 °C. The aqueous solubility of quercetin dihydrate was similar to that of anhydrous quercetin until 80 °C. At temperatures above or equal to 100 °C, the aqueous solubility of quercetin dihydrate was 1.5–2.5 times higher than that of anhydrous quercetin. The aqueous solubility of quercetin anhydrate and dihydrate at different temperatures was correlated using a modified Apelblat equation. The thermodynamic properties of the solution of quercetin and its dihydrate in water were than estimated from their solubility values. A flow rate effect on the aqueous solubility of quercetin and its dihydrate was not observed until above 100 °C where higher solvent (water) flow rates (>0.1 mL/min) were required to maintain a constant solubility in the saturation cell and with minimal thermal degradation of the solute (quercetin dihydrate). The study of its particle morphology under SEM indicated an aggregation of the crystals of quercetin dihydrate at subcritical water temperatures and at lower flow rates (<0.5 mL/min), thereby inhibiting stable solubility measurements and solvent flow through the saturation cell.