Changes in Phenolic Compounds in Garlic (<Emphasis Type="Italic">Allium sativum</Emphasis> L.) Owing to the Cultivar and Location of Growth

The contents of total phenolic compounds, flavonoids, and phenolic acids were determined in selected garlic cultivars grown at four locations. The total phenolic content varied from 3.4 mg gallic acid equivalents (GAE)/g of dry matter (dm) to 10.8 mg GAE/g of dm with a mean value of 6.5 mg GAE/g of dm. The myricetin, quercetin, kaempferol, and apigenin flavonoids were not detected in any of the samples. Caffeic acid and ferulic acid were the major phenolic acids found with mean values of 2.9 mg/kg of dm and 2.6 mg/kg of dm, respectively. The mean contents of vanillic, p-hydroxybenzoic, and p-coumaric acids were comparable (0.4–0.8 mg/kg of dm), and the level of sinapic acid was negligible (< 0.1 mg/kg of dm). There was a significant effect of location but an insignificant effect of genotype on contents of caffeic, vanillic, p-hydroxybenzoic, and p-coumaric acids. However, genotype but not location affected the contents of total phenolics and ferulic acid. On average, the white garlic cultivars and Chinese garlic cultivars contained higher contents of total phenolics and ferulic acid than the purple garlic cultivars. However, the differences in the total phenolic content between the purple and white garlic cultivars were not significant.     

Phenolic acid profiles of Chinese wheat cultivars

Phenolic acid concentrations were determined in 37 Chinese commercial winter wheat cultivars grown at a single site over two seasons, and fractions comprising free and bound types were analyzed using HPLC with measurements of individual phenolic acids in each fraction. Most of the parameters were significantly influenced by cultivar, season, and their interaction effects, with cultivar variance being predominant. Wide ranges of concentration among the 37 cultivars were observed. The average concentration of bound type was 661 μg g⁻¹ of dm, making up 97.5% of the phenolic acid determined with ferulic accounting for 70.7% of it, while free type made up only 2.5% of the phenolic acid determined with syringic accounting for 44.7% of it. Bound type was the predominant source to the grain phenolic acid concentrations determined. There were highly significant and positive correlations between bound ferulic concentration and total bound phenolic acid concentration, and between free syringic concentration and total free phenolic acid concentration. Cultivars Liangxing 66 and Zhongmai 895 were stable in concentration of components of phenolic acids across seasons, with high values of free and bound phenolic acids indicating they could be selected as parents in wheat breeding for health beneficial phenolic acid.     

Phenolic acid profiles of Chinese wheat cultivars

Phenolic acid concentrations were determined in 37 Chinese commercial winter wheat cultivars grown at a single site over two seasons, and fractions comprising free and bound types were analyzed using HPLC with measurements of individual phenolic acids in each fraction. Most of the parameters were significantly influenced by cultivar, season, and their interaction effects, with cultivar variance being predominant. Wide ranges of concentration among the 37 cultivars were observed. The average concentration of bound type was 661 μg g⁻¹ of dm, making up 97.5% of the phenolic acid determined with ferulic accounting for 70.7% of it, while free type made up only 2.5% of the phenolic acid determined with syringic accounting for 44.7% of it. Bound type was the predominant source to the grain phenolic acid concentrations determined. There were highly significant and positive correlations between bound ferulic concentration and total bound phenolic acid concentration, and between free syringic concentration and total free phenolic acid concentration. Cultivars Liangxing 66 and Zhongmai 895 were stable in concentration of components of phenolic acids across seasons, with high values of free and bound phenolic acids indicating they could be selected as parents in wheat breeding for health beneficial phenolic acid.     

Phenolic Compounds as Cultivar- and Variety-distinguishing Factors in Some Plant Products

The aim of the study was to determine whether phenolic compounds in some varieties of buckwheat, winter and spring barley and peas can be used as factors which distinguish selected cultivars and varieties of plant material. It was observed that the content of total phenolics might be useful as a cultivar-distinguishing factor for all the plant materials analyzed, but it was a distinguishing factor for only some varieties. Individual cultivars and varieties were best distinguished by the content of syringic acid. The levels of syringic and vanillic acids were in reverse proportion to the total amount of phenolics soluble in methanol and a positive correlation between syringic and ferulic acid was observed. Moreover, the protein content of plant material was analyzed and a significant (p ≤ 0.05) correlation between this component and ferulic and vanillic acids was noted.     

Phenolic acids composition,total polyphenols content and antioxidant activity of Triticum monococcum, Triticum turgidum and Triticum aestivum: A two-years evaluation

Wheat is a good source of polyphenols, plant metabolytes with beneficial effects on human health. However, little information is available on phenolic acid composition and concentration in different Triticum species, as well as on possible environmental effects. To shed some light on this issue, thirty-nine wheat accessions cropped for two years and belonging to different Triticum species (Triticum monococcum, Triticum turgidum ssp. dicoccum, turanicum and durum, Triticum aestivum ssp. spelta and aestivum) were assessed for phenolic acids (ferulic, p-coumaric, vanillic, syringic, p-hydroxybenzoic, caffeic acids and syringaldehyde), total polyphenols and antioxidant activity in soluble conjugated and insoluble bound extracts. Ferulic acid was the most abundant compound in both extracts. Insoluble bound phenolic acids represented >90% of total phenolic acids. Einkorn showed the maximum concentration of conjugated phenolic acids (50.5 mg/kg DM), while durum and bread wheats presented the highest content of bound phenolic acids (651.8 and 629.2 mg/kg DM, respectively). Cropping year influenced the concentration of conjugated but not of bound phenolic acids. A survey of phenolic acid distribution in the kernel showed that they are rare in endosperm, but abundant in germ and bran. Total polyphenols and antioxidant activity were highly correlated to phenolic acid content.     

Effect of genetic variation on phenolic acid and policosanol contents of Pegaso wheat lines

Total phenolic acid and policosanol contents and compositions of bran from an Italian bread wheat variety Pegaso and its 11 near-isogenic lines were measured. The near-isogenic wheat lines differed at one or more loci coding for storage proteins. The genetic variation included deletions, additions and/or combinations of variations. Almost 95% or more of phenolic acids were in the bound form. Ferulic acid was the predominant bound phenolic acid present in wheat bran samples. Other phenolic acids were p-coumaric, vanillic and syringic acids. Tetracosanol, docosanol, hexacosanol, octacosanol, tricosanol and heneicosanol were found as major policosanol compounds in their decreasing order. Highly significant genotypic differences were observed in total phenolic acid and policosanol concentrations. None of the genetic lines had higher phenolic acid contents than the parent line Pegaso, whereas some of the lines had more policosanol levels. In general, both total phenolic acid composition and contents were higher with genetic lines that varied at Glu-1 loci with 2+Dy high molecular weight glutenin subunit (HMW-GS) (Pegaso 184), variation at Gli-D2 loci (Pegaso 219) and single null A1 (variation at Gli-1/Glu-3 loci; Pegaso 30). Highest total policosanol content was observed with the double null at Glu-A1/Glu-D1 loci (Pegaso 236). These findings may lead to new opportunities for wheat breeders and eventually commercial wheat growers to promote the production of wheat with enhanced levels of health beneficial compounds.     

Influence of sprouting and elicitation on phenolic acids profile and antioxidant activity of wheat seedlings

Influence of germination and elicitation on nutraceutical potential of sprouted wheat was investigated. The seeds of three Polish winter wheat cultivars were elicited with 0.1% (w/v) of Saccacharomyces cerevisiae (SC) extract, 0.1% (v/v) Salix daphnoides (SD) bark extract and their combinations (SC/SD 1:1). Seeds were germinated for 4 day at 20 °C in darkness. For phenolic acids determination LC-ESI-MS/MS analysis was used. Antiradical ability, chelating power, reducing power and ability to prevent lipids against oxidation were determined. Bioaccessibility of antioxidative compounds was estimated using in vitro digestion method. Eleven phenolic acids (protocatechuic, p-hydroxybenzoic, vanillic, caffeic, syryngic, p-coumaric, cis- and trans-ferulic, salicylic, trans- and cis-synapinic) were identified. Sprouting increased p-hydroxybenzoic, syryngic and p-coumaric acids level. The most effective elicitor for improving antioxidant activity of potentially bioaccessible phytochemicals was SD. Especially high effect was obtained for antiradical activity, chelating power and ability to lipid prevention.     

Genome-wide association mapping of phenolic acids in tetraploid wheats

Phenolic acids are major components of cell walls in wheat and have important implications on human health as antioxidants with anti-tumor activity. Our objectives were to identify phenolic acid genes in wheat by single nucleotide polymorphisms (SNPs) detected within the coding sequences of candidate genes, and to identify chromosomal regions associated with single phenolic acids and total soluble phenolic compounds. A set of candidate genes involved in the biosynthesis of hydroxycinnamic acid derivatives were identified by comparative genomics. SNPs found in the coding sequences of six genes (PAL1, PAL2, C4H, C3H, COMT1 and COMT2) were used to determine their chromosomal location and accurate map position on two reference consensus linkage maps. The genome-wide association study (GWAS), based on genotyping a tetraploid wheat collection with 81,587 gene-associated SNPs, detected 22 quantitative trait loci (QTL) distributed on almost all durum wheat chromosomes. Two QTL for p-coumaric acid were coincident with the phenylalanine ammonia-lyase (PAL2) and p-coumarate 3-hydroxylase (C3H) genes on chromosome arms 2AL and 1AL, respectively. The availability of candidate gene-based markers can allow elucidating the mechanism of phenolic acids accumulation in wheat kernels and exploiting the genetic variability of phenolic acids content for the nutritional improvement of wheat end-products.     

Determination of phenolic acid concentrations in wheat flours produced at different extraction rates

High-performance liquid chromatography (HPLC) was used to determine the distribution of phenolic acids in wheat flours produced from five milling extraction rates ranging from 60% to 100% in four cultivars sown in two locations in the 2008–2009 season. Considerable variation was observed in free and bound phenolic acids, and their components in flours with different extraction rates. Most phenolic acids, including the component ferulic, were present in the bound form (94.0%). Ferulic (51.0%) was the predominant phenolic acid in wheat grain, and caffeic (22.8%) and p-coumaric (17.6%) acids were abundant. The phenolic acids and their components were all significantly influenced by effects of cultivar, milling, location, and cultivar × milling interaction, with milling effect being the predominant. The proportions of phenolic compounds varied considerably among milling extractions and cultivars, and their levels depended on both initial grain concentrations and on selection of milling extraction that was incorporated into the final product. The grain phenolic acid concentrations determined ranged from 54 μg g⁻¹ in flour produced at 60% extraction rate to 695 μg g⁻¹ in flour produced at 100% extraction rate, indicating their higher concentrations in bran associated with cell wall materials. Therefore, wholemeal wheat products maximize health benefits and are strongly recommended for use in food processing.     

Ester and ether linkages between hydroxycinnamic acids and lignins from wheat,rice, rye,and barley straws,maize stems,and fast-growing poplar wood

Treatment of solvent extracted wheat, rice, rye, and barley straws, maize stems, and fast-growing poplar wood with 60% aqueous ethanol in 0.2 M HCl at 75 °C for 3 h released 51.8, 51.2, 47.2, 43.7, 54.0, and 16.7% of the original lignin, and 44.3, 50.3, 30.9, 36.1, 40.0, and 25.5% of the original hemicelluloses, respectively. It was found that the bulk of p-coumaric acid (PCA) (67.0–83.5%) was esterified at the lignin side chains, while ferulic acid (FA) is linked to lignin side chains through both ether bonds (51.6–68.3%) and ester bonds (31.7–48.4%), indicating that FA may form intra- and/or inter-molecular ester–ether bridges between lignin fragments, which is first proposed in this study. In addition to p-hydroxybenzoic acid esterified to lignins in the cell walls of wheat straw and fast-growing poplar wood, a small portion of ether-linked p-hydroxybenzoic acid in the lignin preparations, obtained from rice, rye, and barley straws and maize stems, was also detected. It was also detected that noticeable amounts of syringic and vanillic acids were predominantly esterified to the lignin molecules in the cell walls of the materials studied.     

Inhibition of polygalacturonase and polygalacturonic acid lyase fromErwinia carotovora subsp.carotovora by phenolics in vitro

Summary The phenolic acids benzoic, caffeic, chlorogenic, ferulic, p-coumaric, protocatechuic, salicylic, sinapic, syringic and vanillic together with vanillin, were tested for their ability to inhibit polygalacturonic acid lyase (PL) and polygalacturonase (PG) in culture filtrates ofErwinia carotovora subsp.carotovora. None of the compounds inhibited PL at 200 μg/ml, although syringic and sinapic acids caused a 54% and 43% reduction respectively at 400 μg/ml. PG was strongly inhibited by caffeic acid (57% inhibition at 100 μg/ml) and chlorogenic acid caused slight inhibition. Little if any inhibition of PG was caused by benzoic, ferulic, p-coumaric, protocatechuic, salicylic, sinapic, syringic, and vanillic acids or vanillin. The percentage inhibition of PG by chlorogenic acid was not affected by pH values over the range 4–7.     

Pentoses and Hydroxycinnamic Acids in Brewer's Spent Grain

In this work, the total pentose (xylose and arabinose) and hydroxycinnamic acid (ferulic and p -coumaric acids) in eight lots of brewer's spent grain preserved by different methods (freeze-drying, oven drying and freezing) has been determined. The total acid-extractable pentose content of the samples varied between 13·0 and 19·5% dry weight for xylose, and 7·2 and 9·6% dry weight for arabinose, whereas the total alkali-extractable hydroxycinnamic acid content varied between 0·17 and 0·24% dry weight for ferulic acid, and between 0·068 and 0·121% dry weight for p -coumaric acid. Significant differences (p<0·05) between lots were found for ferulic and p -coumaric acids. With respect to the different preservation methods, significant differences (P<0·05) were only seen in arabinose content. The content of pentoses and hydroxycinnamic acids in brewer's spent grain has been compared with those from other agro-food residues whose use is also proposed for the enzymatic release of these compounds.     

Phenolics in the bran of waxy wheat and triticale lines

The present study was designed to determine total phenolic acid contents (TPC) and compositions of bran from newly developed near-isogenic waxy wheat and triticale translocation lines. Two waxy wheat sets, Svevo (durum) and N11 (bread wheat), consisting of partial and waxy null lines and four sets of triticales (GDS7, Trim, Rhino and Rigel) having translocations at 1A.1D and 1R.1D with high molecular weight glutenin subunits (HMW-GS) 5 + 10 and 2 + 12 were investigated. Similar to non-waxy wheat, ferulic acid was the predominant phenolic acid found in waxy wheats analyzed. Two other major phenolics include p-coumaric and vanillic acids followed by lesser quantities of syringic acid. Waxy lines had higher TPC than the parent line in the N11 set, whereas the Svevo set showed the opposite trend. TPC of waxy bread wheats were correlated with amylose fractions in which the order was complete waxy < double waxy nulls < single waxy nulls. Lines with HMW-GS 2 + 12 have lower TPC than other lines in each group of triticales, except the Trim set. TPC was negatively correlated (r = −0.41; p > 0.1) with bran yields in triticale lines studied, indicating that variation in phenolics was not only due to bran yields but also to genotypic differences.     

Anthocyanins,Phenolic Acids and Antioxidant Properties of Juçara Fruits (Euterpe edulis M.) Along the On-tree Ripening Process

Juçara (Euterpe edulis M.) fruits are an interesting source of phenolic compounds, mainly anthocyanins, making them valuable to the food and pharmaceutical industries. Juçara fruits were harvested along the on-tree ripening process between March and June as practiced in Paraná state, Brazil and examined for their total anthocyanin content (TAC), total phenolic content (TPC), total phenolic acid (TPA) and total antioxidant capacity (TAA). Overall, TAC increased (91.52–236.19 mg cyanidin-3-glucoside equivalent/100 g dm) whereas TPC (81.69–49.09 mg GAE/g dm) and TPA (44.27–30.95 mg/100 g dm) decreased during ripening of juçara fruits. Use of tandem mass spectrometry allowed the identification of cyanidin-3,5-diglucoside, peonidin-3-glucoside and peonidin-3-rutinoside for the first time in juçara fruits. The analysis of the phenolic acids by HPLC-MS/MS indicated the presence of gallic, protocatechuic, p-hydroxybenzoic, vanillic, chlorogenic, caffeic, syringic, p-coumaric, sinapinic and ferulic acids. The high antioxidant capacity using DPPH radical scavenging capacity (655.89–745.32 μmol TE/g dm) and ORAC assays (1088.10–2071.55 μmol TE/g dm) showed that juçara fruits have potential as a source of novel natural antioxidants for disease prevention and health promotion, and also as natural food additives for developing new functional food products.     

Variation in Oat Groats Due to Variety, Storage and Heat Treatment. I: Phenolic Compounds

Low molecular weight phenolic compounds present in heat processed oats (Avena sativaL) were analysed. The oat grains were of three varieties (Kapp, Mustang and Svea), stored at different relative humidities (30, 55 or 80%) and periods (3·5 or 15·5 months) and processed with or without hulls. Eleven UV-absorbing compounds detected by High Performance Liquid Chromatography were subjected to univariate and multivariate statistical analysis. The selected compounds included caffeic acid,p-coumaric acid, ferulic acid, vanillic acid,p-hydroxybenzaldehyde, vanillin, coniferyl alcohol, three avenanthramides and one unidentified substance. The levels of vanillic acid, vanillin and, especially,p-coumaric acid,p-hydroxybenzaldehyde and coniferyl alcohol increased significantly in samples processed with hulls, but not in samples processed without hulls. Ferulic acid increased in both processes, while caffeic acid and the avenanthramides were found to decrease during processing. Storage of unprocessed samples for 1 year generally increased the levels of phenolic acids and aldehydes. For the phenolic acids (except ferulic acid), this increase was most pronounced after storage at high relative humidity (80%). The avenanthramides were present at their highest levels in Mustang, caffeic acid in Svea and Mustang, the unidentified compound in Svea, while all the other compounds studied were present predominantly in the variety Kapp.     

镍处理下水稻酚酸和酚多聚物含量的变化与白叶枯病诱导抗性的关系

 研究了镍处理下水稻叶片中总酚、酚酸、酚多聚物积累和细胞壁结合态过氧化物酶（POD）活性的变化。镍处理导致总酚含量显著上升,检测到10种可溶性酚酸和7种结合态酚酸。镍处理下可溶性绿原酸和水杨酸含量明显上升,而它们的结合态含量变化不明显;镍处理显著提高可溶性和结合态阿魏酸的含量,显著降低可溶性丁香酸和对 香豆酸的含量,却诱导其结合态含量增加。镍处理后酚多聚物明显积累,以阿魏酸和丁香醛为底物的细胞壁结合态POD的活性显著升高。这些结果结合以前的研究提示,酚酸和酚多聚物积累参与了镍诱导的水稻对白叶枯病的抗性。     

Effect of baking on free and bound phenolic acids in wholegrain bakery products

Phenolic compounds, particularly ferulic acid the most abundant phenolic in wheat, are the major contributors to the in vitro antioxidant capacity. They are present in wheat in free and bound forms which affect their bioavailability. Thus the current study aims to investigate changes in free and bound phenolic acids occurred during baking in wholegrain bread, cookie and muffin. The products were also fortified with lutein due to its proved health benefits, and were previously evaluated with regard to lutein stability and bioavailability and antioxidant properties. The control and fortified wholegrain bakery products contained reasonable amounts of free and bound phenolic acids with bread products exhibiting the highest level per serving (0.6 and 11.7 mg, respectively). Ferulic acid was the principal phenolic both in the free or bound extracts of the three products followed by p-coumaric acid in the bound extracts. Baking resulted in an increase in free phenolic acids in the three products, while bound phenolic acids decreased in bread and slightly changed in cookie and muffin products. Though the effect of baking appeared to be dependent on type of baked product, type of phenolic, recipe and baking conditions, the wholegrain products should be considered good sources of phenolic antioxidants.     

Phenolic antioxidant-linked anti-hyperglycemic properties of rye cultivars grown under conventional and organic production systems

Rye (Secale cereale L.), is a temperate cereal food crop with diverse human health benefits partly linked to phenolic bioactives. Therefore targeting rye cultivars rich in phenolic bioactives and associated antioxidant properties has relevance to develop dietary support against chronic diseases, such as hyperglycemia linked to progression of type 2 diabetes. In this study we screened 9 rye cultivars and compared the impact of two different production practices (conventional and organic) on phenolic bioactive associated antioxidant and anti-hyperglycemic properties using in vitro assay models. Total soluble phenolic content (TSP), phenolic acids profile, protein content, antioxidant activity (AA), and hyperglycemia relevant α-amylase and α-glucosidase enzyme inhibitory activities of aqueous extracts of rye cultivars were evaluated using in vitro models. Overall, rye grown under organic production had higher yield, 1000 kernel weight, α-amylase inhibitory activity, and ferulic and benzoic acid content. On the contrary rye grown under conventional production had higher TSP content, AA, and α-glucosidase enzyme inhibitory activity. Further significant differences in phenolic antioxidant-linked anti-hyperglycemic properties among 9 rye cultivars were observed. This study indicated that differences in cultivars and production practices had significant impact on human health relevant phenolic antioxidant and associated anti-hyperglycemic properties of rye cultivars.     

不同类型大麦品种籽粒中酚酸类化合物含量的差异

为了探明不同类型大麦品种籽粒中酚酸类化合物含量的差异,采用超声辅助提取、高效液相色谱测定的方法对15个大麦品种（系）籽粒中的13种酚酸含量进行了比较分析。结果表明,大麦籽粒中的酚酸类化合物主要是羟基苯甲酸衍生物,羟基肉桂酸衍生物含量较少。不同类型大麦品种籽粒中酚酸类化合物的含量存在极显著的差异,黑皮大麦籽粒中总羟基苯甲酸衍生物（THBA）、总羟基肉桂酸衍生物（THCA）和总酚酸（TPA）的含量均高于非黑皮大麦;二棱大麦籽粒中THBA、THCA和TPA的含量均高于多棱大麦;皮大麦籽粒中THCA和TPA的含量高于裸大麦,但THBA的含量与裸大麦无显著差异。另外,与裸大麦相比,皮大麦籽粒中含有更为丰富的酚酸种类。     

Phenolic composition and antioxidant capacity of six artemisia species

The aim of this work was to establish the antioxidant capacities and the polyphenolic profile of six different Artemisia species that could potentially be used in the human diet. A high-performance liquid chromatographic method coupled with photodiode-array detector was used to identify and quantify individual phenolic compounds of the Artemisia leaves. A total of 18 polyphenolic compounds were identified and quantified in Artemisia leaves, including hydroxybenzoic acids (4), hydroxycinnamic acids (5), flavonols (3), and catechins (2). It was observed that total phenolic content of A. annua and A. stelleriana leaves were significantly lower than the other four species. Ferulic and caffeic conjugates acids were the most dominant hydroxycinnamic acid and gallic acid and catechin were the most dominant hydroxycinnamic acid and catechins respectively. According to DPPH assays, the antioxidant capacity of A. arborescens spp., A. ludoviciana spp., A. oleandica spp. and A. princepts spp., were found to be higher (reflecting a 2-fold difference) than that of the other two species. Compared with those of major commercial leafy vegetables, leaves of Artemisia contain a higher content of flavonoids and phenolic acids, which provide significant health benefits and may be used as natural colorants.