Cytotoxic phenylpropanoid glycosides from Fagopyrum tataricum (L.) Gaertn

Fagopyrum tataricum (L.) Gaertn (tartary buckwheat) is an ancient dicotyledonous crop belonging to Polygonaceae family. Besides its benefits for human consumption, tartary buckwheat is also an important folk medicine in China for its antioxidant, antitumour, hypotensive, hypoglycaemic and hypolipidaemic activities. Phytochemical investigation of the ethyl acetate fraction of tartary buckwheat roots led to the isolation of seven new phenylpropanoid glycosides, tatarisides A-G (1-7), together with a known phenylpropanoid glycoside, diboside A (8). Their structures were elucidated by means of spectroscopic methods. All compounds (1-8) were evaluated for their cytotoxic activity against four human cancer cell lines (A-549, HCT116, ZR-75-30 and HL-60). Tatariside C (3) was the most active compound with IC₅₀ values of 6.44-7.49 μg/ml against the four tested cell lines.     

Purification and identification of angiotensin I-converting enzyme inhibitory peptide from buckwheat (Fagopyrum esculentum Moench)

Angiotensin I-converting enzyme (ACE) inhibitory peptide was isolated and identified from buckwheat (Fagopyrum esculentum Moench). Buckwheat protein extract was prepared by stirring in water (pH 9.0) for 30 min, followed by centrifugation at 15,000g for 20 min. The protein extract was then filtered using an YM-10 membrane. An ACE inhibitor was purified using consecutive chromatographic methods including: ion-exchange chromatography, gel filtration chromatography, and reverse-phase high performance liquid chromatography. The ACE inhibitor was identified to be a tripeptide, Gly-Pro-Pro, having IC₅₀ value of 6.25 μg protein/ml, by protein sequencing system and electrospray-LC–mass spectrometry.     

Rutin content in buckwheat (Fagopyrum esculentum Moench) food materials and products

The rutin content of buckwheat products was compared to the rutin content in their raw materials, in order to evaluate their value for producing functional foods. There is much less rutin in noodles (78 mg/kg, d.w.b. – dry weight basis), than in the dark buckwheat flour (218 mg/kg, d.w.b.) from which they are produced. One of the possible explanations is the presence of the rutin degrading enzyme. In raw (uncooked) groats there is 230 mg/kg (d.w.b.) of rutin and in precooked groats, 88 mg/kg (d.w.b.). In buckwheat beer and vinegar there is a negligible content of rutin. Buckwheat leaf flour contains about 2700 mg/kg (d.w.b.) rutin, and is thus a suitable material for enriching functional foods, giving it the potential for preventive nutrition.     

Physicochemical and antioxidant properties of buckwheat (Fagopyrum esculentum Moench) protein hydrolysates

The enzymatic hydrolysis of common buckwheat (Fagopyrum esculentum Moench) protein isolate (BPI) by Alcalase and some physiochemical and antioxidant properties of the resulting hydrolysates were characterised. The hydrolysis resulted in remarkable decrease in the globulins or protein aggregates and concomitant increase in peptide fragments. The surface hydrophobicity of the hydrolysates decreased with increasing degree of hydrolysis (DH) and reached a minimum at DH 15%, but increased at further hydrolysis, whereas their amino acid compositions were unchanged. The polyphenol content of the hydrolysates gradually decreased with DH increasing from 0% to 15%, while it on the contrary increased upon further hydrolysis. The hydrolysates exhibited excellent antioxidant activities, including DPPH radical scavenging ability, reducing power and ability to inhibit linoleic acid peroxidation. The antioxidant activities of these hydrolysates were closely related to their polyphenol contents. The results indicated that polyphenol-rich buckwheat proteins are unique protein materials for the production of the hydrolysates with good nutritional and antioxidant properties.     

Structural characterization of globulin from common buckwheat (Fagopyrum esculentum Moench) using circular dichroism and Raman spectroscopy

Raman and far-UV circular dichroism (CD) spectroscopy was used to study the conformation of globulin from common buckwheat (Fagopyrum esculentum Moench) (BWG) under the influence of various buffer environments and heat treatments. Secondary structural analysis of BWG by CD spectroscopy yielded 15.0% α-helical, 25.8% β-sheet, 28.9% β-turn and 30.3% random coil contents. Raman spectrum also showed β-sheets as the major secondary structure in native BWG. Chaotropic salts caused band shifts and intensity changes in Raman amide III vibration, indicating transitions from β-sheet to disordered structure following the lyotropic series of anions. Extreme pHs and several protein structure perturbants led to changes in CD and Raman spectral characteristics, demonstrating protein unfolding and denaturation. Increasing heating time at 100 °C induced the appearance of anti-parallel β-sheet (1235–1237 cm⁻¹) and caused a progressive increase in random coil content, suggesting protein denaturation and aggregation. Both non-covalent and covalent interactions play important roles in stabilizing the conformation of BWG.     

Effect of processing on buckwheat phenolics and antioxidant activity

The effect of processing on functional compounds in buckwheat was investigated. Extractions of buckwheat flour were carried out before and after roasting or extrusion. Folin–Ciocalteu assays indicated that processing did not cause any change in total phenolic content in buckwheat flour. Roasted (200 °C, 10 min) dark buckwheat flour exhibited an increase in non-polar compounds as well as polar compounds whereas extrusion exhibited increase only in polar compounds. Antioxidant activity test (DPPH) showed that roasting at 200 °C for 10 min decreased the antioxidant activity slightly whereas extrusion (170 °C) did not cause any change. The results suggest that processing conditions can be optimized to retain the health promoting compounds in buckwheat products.     

Hepatoprotective and antioxidant activity of ethanolic extracts of edible lotus (Nelumbo nucifera Gaertn.) leaves

Lotus (Nelumbo nucifera Gaertn.), an aquatic vegetable, is extensively cultivated in eastern Asia, particularly in China. An ethanolic extract of the leaves was studied for its hepatoprotective activity against CCl₄-induced liver toxicity in rats. In vitro and in vivo antioxidant activity was also assessed. The results showed the hepatoprotective activity of lotus leaf extract (LLE) at doses of 300 and 500 mg/kg and in vivo antioxidant activity at 100 mg/kg that was comparable with that of a standard treatment comprising 100 mg/kg of silymarin, a known hepatoprotective drug. These data were supplemented with histopathological studies of rat liver sections. The main flavonoids and phenolic compounds of LLE were analysed by HPLC-DAD-ESI/MS methods. Six of the compounds detected were tentatively characterised, one as catechin glycoside and five as flavonoid glycoside derivatives: miricitrin-3-O-glucoside, hyperin, isoquercitrin, quercetin-3-O-rhamnoside and astragalin.     

Effect of salinity stress on phenolic compounds and carotenoids in buckwheat (Fagopyrum esculentum M.) sprout

The effect of salinity stress on the nutritional quality of buckwheat sprouts cultivated for 1, 3, 5, and 7d was investigated by analysis of the antioxidant activity and levels of phenolic compounds and carotenoids. Treatment with various concentrations of NaCl (10, 50, 100, and 200mM) resulted in an increase in the amount of phenolic compounds and carotenoids in the sprouts compared with the control (0mM). The phenolic contents of sprouts treated with 10, 50, and 100mM after 7d of cultivation were 57%, 121%, and 153%, respectively, higher than that of the control (0mM NaCl). Moreover, the accumulation of phenolic compounds was primarily caused by an increase in the levels of 4 compounds: isoorientin, orientin, rutin, and vitexin. The carotenoid content of sprouts treated with 50 and 100mM NaCl was twice higher than that of the control. In addition, the antioxidant activity of ethanol extracts of the sprouts was increased by NaCl treatment. Although the growth rate of sprouts decreased with >50mM NaCl, these results suggest that treatment of an appropriate concentration of NaCl improves the nutritional quality of sprouts, including the level of phenolic compounds, carotenoids, and antioxidant activity.     

Quality and antioxidant property of buckwheat enhanced wheat bread

Common buckwheat (Fagopyrium esculentum Moench) was used to substitute 15% of wheat flour to make buckwheat enhanced wheat breads. Proximate composition, physical quality, functional components and antioxidant properties of buckwheat enhanced wheat breads were analysed and compared with those of white bread. Specific volumes of three breads were 6.10–6.75 cm³/g. Buckwheat enhanced wheat bread showed lower lightness and whiteness index values and higher redness and yellowness values. On a seven-point hedonic scale, all sensory results were 5.33–5.91, indicating that three breads were moderately acceptable. No differences were found in appearance, colour and overall sensory attributes for three breads, whereas both buckwheat enhanced wheat breads were rated higher in flavour and mouth feel. Buckwheat enhanced wheat bread contained more rutin and quercetin as expected. Buckwheat enhanced wheat bread was good in antioxidant activity, reducing power and 1,1-diphenyl-2-picrylhydrazyl radical scavenging ability with unhusked buckwheat enhanced wheat bread being the most effective. Overall, buckwheat enhanced wheat bread could be developed as a food with more effective antioxidant properties.     

Phenolic content and antioxidant activity of extracts from whole buckwheat (Fagopyrum esculentum Möench) with or without microwave irradiation

The purpose of this study was to extract phenolic compounds and antioxidant activity from buckwheat with water, 50% aqueous ethanol, or 100% ethanol using microwave irradiation or a water bath for 15 min at various temperatures (23–150 °C). Phenolic content of extracts increased with increasing temperature. In general, phenolic contents in microwave irradiated extracts were higher than those heated with a water bath. The highest phenolic content, 18.5 ± 0.2 mg/g buckwheat, was observed in the extract that was microwave irradiated in 50% aqueous ethanol at 150 °C. The highest antioxidant activities, 5.61 ± 0.04–5.73 ± 0.00 μmol Trolox equivalents/g buckwheat, were found in the 100% ethanol extracts obtained at 100 and 150 °C, independent of heat source. These results indicate that microwave irradiation can be used to obtain buckwheat extracts with higher phenolic content and similar antioxidant activity as extracts heated in a water bath.     

Chemical composition and antioxidant activity of Gaylussacia brasiliensis (camarinha) grown in Brazil

This paper presents the centesimal and mineral composition, fatty acid profile of the lipidic fraction, phenolic and anthocyanin contents, and antioxidant activity of Gaylussacia brasiliensis fruit. The results indicated the following composition: moisture (81.30%), lipids (0.62%), proteins (0.56%), carbohydrates (10.74%), dietary fiber (6.53%), and ash (0.25%). The main elements comprising the mineral composition were K, Mg, Ca, and Fe. The fatty acid composition was characterized by a high content of polyunsaturated fatty acids (62.2%) and a high PUFA/SFA ratio (2.92). The G. brasiliensis fruit contained considerable amounts of phenolics (492.87 mgAG/100 g) and anthocyanins (240.43 mg/100 g), which contribute to its high antioxidant activity. This study highlights the potential of this fruit as an important source of both nutritional and bioactive compounds available in the native Brazilian flora.     

Phytochemicals and antioxidant activity of different parts of bambangan (Mangifera pajang) and tarap (Artocarpus odoratissimus)

Mangifera pajang (family: Anacardiaceae; local name: bambangan) and Artocarpus odoratissimus (familiy: Moraceae; local name: tarap) are popular edible fruits in Sabah, Malaysia. The flesh, kernel and peel from M. pajang; seed and flesh from A. odoratissimus were analysed for total antioxidant activity, total polyphenol, total flavonoid and total anthocyanins contents. M. pajang kernel extract displayed the highest free radical scavenging and ferric reducing activities. Total phenolic content of the samples were in the range of 5.96–103.3 mg gallic acid equivalent/g. M. pajang kernel and M. pajang flesh contained the highest and lowest total flavonoid content with the values of 10.98 and 0.07 mg rutin equivalent/g, respectively. The antioxidant activities of extracts were significantly correlated with the total phenolic and flavonoid content (but not the anthocyanins content). The phytochemicals and antioxidant properties of M. pajang and A. odoratissimus, especially their by-products (kernel/seed), indicate that they may impart health benefits when consumed and should be regarded as a valuable source of antioxidant-rich nutraceuticals.     

Constituents of Sideritis syriaca. ssp. syriaca (Lamiaceae) and their antioxidant activity

The aerial parts of Sideritis syriaca ssp. syriaca (Lamiaceae) were extracted, after defatting, with diethyl ether, ethyl acetate and n-butanol. The antioxidant activities of the extracts were evaluated through in vitro model systems, such as 1,1-diphenyl-2-picryl hydrazyl (DPPH) and Co(II) EDTA-induced luminol chemiluminescence. In both model systems the ethyl acetate extract was the most effective. Phytochemical analysis of ethyl acetate extract showed the presence of two new isomeric compounds (1 and 1′), identified as 1-rhamnosyl, 1-coumaroyl, dihydrocaffeoyl, protocatechuic tetraester of quinic acid, as well as chlorogenic acid (2), apigenin 7-O-glucoside (3), apigenin (4), 4′-O-methylisoscutellarein 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1 → 2)-β-d-glucopyranoside] (5), isoscutellarein 7-O-[6′′′-O-acetyl-β-D-allopyranosyl-(1 → 2)-β-d-glucopyranoside] (6), 4′-O-methylisoscutellarein 7-O[β-d-allopyranosyl-(1 → 2)-β-d-glucopyranoside] (7) and 4′-O-methylisoscutellarein 7-O-[β-d-allopyranosyl-(1 → 2)-6′′-O-acetyl-β-d-glucopyranoside] (8). The above compounds were identified by spectroscopic methods.     

Distribution of phenolic compounds in the graded flours milled from whole buckwheat grains and their antioxidant capacities

Whole buckwheat grains were milled into 16 flour fractions using the gradual milling system and the phenolic compounds and the antioxidant capacity of each flour fraction were investigated. The phenolic and flavonoid contents of both free and bound phenolic extracts of buckwheat flour fractions significantly increased in the order from the fraction number 1 (phenolics less rich fraction) to the fraction number 16 (phenolics rich fraction). The phenolic compounds in buckwheat existed primarily in free form, whereas the flavonoids existed in grain in insoluble bound forms, bound to cell wall materials. The amounts of ferulic acid and rutin increased from 2.5 and 2.5 μg/g flour of the phenolics less rich fraction to 609.5 and 389.9 μg/g flour of the phenolics rich fraction of grain, respectively. The higher phenolic contents in the phenolics rich fractions exhibited the stronger antioxidant capacity than the phenolics less rich fractions. As a result, the flour milled from the outer layers of buckwheat grains with large amount of phenolic compounds and antioxidant capacity are considered to have significant health benefits.     

Salicylaldehyde is a characteristic aroma component of buckwheat groats

Salicylaldehyde (2-hydroxybenzaldehyde) was identified as a characteristic component of buckwheat groats aroma by a sensory analysis guided fractionation of the extract. The extract with the strongest odour was prepared by petroleum ether extraction of water soaked groats. This extract was further extracted with sodium hydrogen carbonate solution and purified by a preparative layer chromatography and identified by NMR, MS and IR spectroscopy. A capillary electrophoresis method was developed and used to determine salicylaldehyde content in buckwheat groats and flour samples. Traditionally dehulled buckwheat grain, which had the strongest odour, contained the highest concentration (1.6 ppm) of salicylaldehyde with an odour activity value (OAV) of 216.     

Loss of rutin and antioxidant activity of asparagus juice caused by a pectolytic enzyme preparation from Aspergillus niger

We found that a commercial pectolytic enzyme preparation from Aspergillus niger (pectinase AN) contained laccase activity that decreased rutin content and antioxidant activity of asparagus juice. This research investigated the effects of pH, temperature, and concentration of pectinase AN on pectinase AN’s laccase activity to decrease rutin content and antioxidant activity of asparagus juice. Asparagus juice was incubated with pectinase AN at different pHs (3.2, 4.5 and 5.8), temperatures (25, 37, and 50 °C) and enzyme concentrations (0.1%, 0.5% and 1%). Rutin content and antioxidant activity of samples was determined by HPLC and 2,2′-diphenyl-1-picrylhydrazyl (DPPH) free radical method, respectively. The rate of loss of rutin and antioxidant activity of asparagus juice was smaller at pH 3.2 than at pH 4.5 and pH 5.8, smaller for 0.1% pectinase AN than 0.5% and 1% pectinase AN. The rate of loss of rutin of asparagus juice was greater at 25 °C than at the other two temperatures. Pectinase AN can decrease rutin content and antioxidant activity of asparagus juice at the selected conditions. But rutin content and antioxidant activity of asparagus juice produced using pectinase AN could be less decreased at pH 3.2 and 0.1% of enzyme with less than 2 h of incubation time. This information was helpful for juice industry to produce juices with high antioxidant activity using pectinase AN.     

Physicochemical and structural characterisation of globulin and albumin from common buckwheat (Fagopyrum esculentum Moench) seeds

The physicochemical and conformational properties of globulin (BG) and albumin (BA) fractions from common buckwheat seeds were characterised, and compared with those of buckwheat protein isolate (BPI). The polyphenol contents were also evaluated. The polyphenol content in BA was much higher than that in BG, and most of the polyphenols in the BA was in the free form, whilst that in the BG and BPI was mainly in the protein-bound form. The BA had higher content of uncharged polar amino acids, but lower acidic amino acids than BG. The protein solubility-pH profile of the BG and BA were very different, especially at pH 4.0–6.0. Far-UV and near-UV CD and intrinsic fluorescence spectra indicated that the secondary and/or tertiary conformations of BA were much more flexible than those of BG, but also more easily affected by the polyphenols. The results indicated that the properties of BG and BA varied considerably, and were largely dependent upon their polyphenol levels and the interactions of the polyphenols and the proteins.     

The antioxidant activity and the bioactive compound content of Stevia rebaudiana water extracts

Stevia rebaudiana (SR), a chrysanthemum herb, has been used as a vegetable-based sweetening additive in health drinks and in other foods. This study was conducted to investigate the antioxidant activity and the bioactive compounds found in water extracts taken from SR leaves and calli. Analysis of vitamins in the leaves showed that folic acid (52.18 mg/100 g) was a major component, followed by vitamin C. The total phenolic and flavonoid contents were found to be 130.76 μg catechin and 15.64 μg quercetin for leaves and 43.99 μg catechin and 1.57 μg quercetin for cellus at mg of water extracts, respectively. Pyrogallol was the major material among the phenolic compounds in both leaf and callus extracts. Furthermore, our results showed that the leaf extracts contained higher amounts of free radicals, hydroxyl radicals and superoxide anion radical scavenging activities than those of the callus extracts.