Phenolic compounds in strawberry (Fragaria x ananassa Duch.) fruits: Composition in 27 cultivars and changes during ripening

Phenolic compounds in fruits of 27 cultivars of strawberry (Fragaria x ananassa Duch.) grown in Norway were characterised and quantified by HPLC-DAD-MSⁿ. Total phenolic content, calculated as the sum of the individual compounds, varied 2.3-fold among cultivars, i.e., from 57 to 133 mg/100 g of fw. There were significant differences among cultivars in concentration of all phenolic compounds. The highest variation between cultivars was found for cinnamoyl glucose (0.6-24.9 mg/100 g of fw). Concentration of anthocyanins, the most abundant class of phenolic compounds in the majority of the cultivars, varied from 8.5 to 65.9 mg/100 g of fw. Flavan-3-ols (11-45 mg/100 g of fw) and ellagitannins (7.7-18.2 mg/100 g of fw) contributed on average 28% and 14% to total phenolic contents in the strawberry cultivars, respectively. In three cultivars harvested at three stages of ripeness, anthocyanins and cinnamic acid conjugates were the compounds most affected by ripening. The anthocyanin profile for the individual cultivars was only slightly affected by ripening and growing conditions.     

Potassium rate alters the antioxidant capacity and phenolic concentration of basil (Ocimum basilicum L.) leaves

In the current study, we have determined how potassium rate affects the phenolic levels and antioxidant properties of three cultivars of basil (Ocimum basilicum L.) leaves: Dark Opal, Sweet Thai, and Genovese. Potassium rate increased the total phenolic concentration in basil, with basil treated at the highest potassium rate, 5.0 mM K, containing greater phenolic levels than basil treated at the lowest potassium rate, 1.0 mM K (p = 0.008). Basil grown at 5.0 mM K also had higher concentrations of rosmarinic (p = 0.005) and chicoric (p < 0.001) acids compared to lower potassium treatment levels. Correspondingly, 1.0 mM K basil had lower DPPH (2,2′-diphenyl-1-picrylhydrazyl) (p ? 0.005) and FRAP (ferric reducing antioxidant power, p = 0.043) antioxidant capacities compared to basil treated at higher potassium rates. Cultivar was also found to impact the phenolic composition and antioxidant properties of basil, with Sweet Thai having lower total phenolic concentrations and FRAP antioxidant capacities than Dark Opal and Genovese. Although not affected by potassium rate, anthocyanin concentrations varied significantly among the cultivars, with purple Dark Opal basil exhibiting higher anthocyanin levels than Sweet Thai (p = 0.003) and Genovese (p = 0.002).     

Variations in phenolic composition and antioxidant properties among 15 basil (Ocimum basilicum L.) cultivars

In this study, the influences of cultivar on the phenolic composition and antioxidant properties of 15 different basil varieties was determined. Cultivar had a statistically significant effect on total phenolic levels (p < 0.001) and anthocyanin concentrations (p < 0.001). Analysis of individual phenolic acid levels by high-performance liquid chromatography showed substantial variations in the phenolic acid profiles among cultivars. Rosmarinic (p < 0.001), chicoric (p = 0.002) and caffeic (p = 0.001) acid concentrations were affected by cultivar, although caftaric acid levels (p = 0.083) were not. Nine of the cultivars in this study contained chicoric acid in higher concentrations than rosmarinic acid. These are the first basil cultivars that have been identified in which rosmarinic acid is not the dominant phenolic acid. In addition, six of the cultivars in this study had caftaric and caffeic acid concentrations that were similar or higher than rosmarinic acid levels. Cultivar also had a significant impact on both FRAP (ferric reducing antioxidant power, p = 0.007) and DPPH (2,2′-diphenyl-1-picrylhydrazyl, p = 0.004) antioxidant capacities. For the basil cultivars in this study, the individual phenolic acid composition was found to be an important factor influencing the measured antioxidant capacity.     

Chemical stability of açai fruit (Euterpe oleracea Mart.) anthocyanins as influenced by naturally occurring and externally added polyphenolic cofactors in model systems

The influence of different classes of naturally occurring and externally added polyphenolic cofactors on the phytochemical and colour stability of anthocyanins in açai fruit (Euterpe oleracea) was investigated. Model systems were based on anthocyanin isolates from açai fruit, rich in cyanidin-3-rutinoside (311 ± 27 mg/l) and cyanidin-3-glucoside (208 ± 18 mg/l), and isolated groups of naturally occurring polyphenolic cofactors in açai fruit (phenolic acids, procyanidins, and flavone-C-glycosides, each adjusted to ∼50 mg/l). Anthocyanin degradation kinetics were assessed as a function of pH (3.0, 3.5, and 4.0) and storage temperature (5, 20 and 30 °C). During storage, anthocyanins experienced pH and temperature-dependent losses, and the half life cyanidin-3-rutinoside (t_1/2 = 2.67–210 days) was consistently longer than cyanidin-3-glucoside (t_1/2 = 1.13–144 days). The presence of flavone-C-glycosides induced significant hyperchromic shifts and enhanced anthocyanin stability at all pH and temperature combinations, while no significant effects were attributed to the presence of phenolic acids or procyanidins. Additional models using externally added cofactors from rooibos tea, also rich in flavone-C-glycosides, resulted in up to 45.5% higher anthocyanin colour and up to 40.7% increased anthocyanin stability compared to uncopigmented anthocyanin isolates and had similar copigmentation effects to a commercial rosemary-based colour enhancer. Results suggest flavone-C-glycosides offer potential for their use as colour enhancers and stabilizing agents in products rich in cyanidin glycosides, particularly açai fruit-containing foods, juice blends, and beverages.     

Methyl jasmonate enhances antioxidant activity and flavonoid content in blackberries (Rubus sp.) and promotes antiproliferation of human cancer cells

The effects of preharvest methyl jasmonate (MJ) application on fruit quality, antioxidant activity and flavonoid content in blackberries (Rubus sp.) were determined. Anticancer activity against human lung A549 cells and HL-60 leukemia cells was also evaluated. Three blackberry cultivars (Chester Thornless, Hull Thornless and Triple Crown) were used in these experiments. Blackberries treated with MJ (0.01 and 0.1 mM) had higher soluble solids content, and lower titratable acids than untreated fruit as well as enhanced content of flavonoids and increased antioxidant capacity. Extracts of treated fruit showed enhanced inhibition of A549 cell and HL-60 cell proliferation and induced the apoptosis of HL-60 cells. Cultivar Hull Thornless had higher soluble solids and lower titratable acids compared to cv. Chester Thornless and Triple Crown. On the basis of fresh weight of fruit, Hull Thornless also had significantly higher anthocyanin, total phenolic content, antioxidant and antiproliferation activity than other two cultivars.     

Fruit quality and bioactive compounds relevant to human health of sweet cherry (Prunus avium L.) cultivars grown in Italy

The fruit quality characteristics, phenolic compounds and antioxidant capacities of 24 sweet cherry (Prunus avium L.) cultivars grown on the mountainsides of the Etna volcano (Sicily, Italy) were evaluated. High-performance liquid chromatographic methods were used to identify and quantify sugars, organic acids and phenolics. A total of seven phenolic compounds were characterised as hydroxycinnamic acid derivatives (neochlorogenic acid, p-coumaroylquinic acid and chlorogenic acid) and anthocyanins (cyanidin 3-glucoside, cyanidin 3-rutinoside, pelargonidin 3-rutinoside and peonidin 3-rutinoside). The total anthocyanin content ranged from 6.21 to 94.20 mg cyanidin 3-glucoside equivalents/100 g fresh weight (FW), while the total phenol content ranged from 84.96 to 162.21 mg gallic acid equivalents/100 g FW. The oxygen radical absorbance capacity (ORAC) assay indicated that fruit of all genotypes possessed considerable antioxidant activity. The high level of phenolic compounds and antioxidant capacity of some sweet cherry fruits implied that they might be sources of bioactive compounds that are relevant to human health.     

Inhibitory effect of raspberries on starch digestive enzyme and their antioxidant properties and phenolic composition

Seven primocane fall-bearing raspberry (Rubus idaeus L.) cultivars, Nova (red), Dinkum (red), Heritage (red), Autumn Britten (red), Josephine, Anne (yellow), Fall Gold (yellow) were analysed for potential health promoting properties including their inhibitory effect on starch and fat digestive enzymes, antioxidant activities, and phenolic composition. The tested raspberry extracts showed no detectable inhibition of pancreatic α-amylase and lipase. However, all the extracts exhibited potent inhibition of α-glucosidase with IC₅₀ from 16.8 to 34.2 μg/mL. Four phenolic compounds, ellagic acid, cyanidin-diglucoside, pelargonidin-3-rutinoside, and catechin were identified as the active α-glucosidase inhibitors. The raspberry extracts also possessed significant antioxidant activities with oxygen radical absorbance capacities (ORAC) ranging from 136.7 to 205.2 μmol Trolox equivalents (TE)/g dry weight fruit and DPPH radical scavenging activities from 305 to 351 μmol TE/g. The total phenolic content of raspberry cultivars varied significantly from 40.9 to 98.5 mg of gallic acid equivalents/g dry weight. The anthocyanin content varied widely from 0.1 to 9.5 mg cyanidin 3-glucoside equivalents/g. Nine phenolic acids were quantified in raspberries and their total amounts varied from 157.3 to 713.5 μg/g. The enzyme inhibition and antioxidant properties of raspberry cultivars were not correlated with their total phenolic, anthocyanin, and phenolic acid content. Overall, ‘Dinkum’ and ‘Josephine’ raspberry varieties possess higher total phenolic content, ORAC, DPPH radical scavenging activity, and α-glucosidase inhibitory activity than other five cultivars.     

Evaluation of different Saccharomyces cerevisiae strains for red winemaking. Influence on the anthocyanin,pyranoanthocyanin and non-anthocyanin phenolic content and colour characteristics of wines

The possible industrial use of three previously-selected Saccharomyces cerevisiae strains (1EV, 2EV and 7EV) has been studied in musts derived from Tempranillo and Cabernet Sauvignon. The anthocyanin, pyranoanthocyanin and non-anthocyanin phenolic content, and colour characteristics of the resulting wines have been compared to those of a commercial strain. Anthocyanins were the compounds most influenced by the yeast strain. Independently of the grape variety, wines derived from 2EV presented significantly higher anthocyanin concentrations than those derived from 1EV and 7EV, which presented similar contents. With the exception of hydroxycinnamic acids and derivatives, no particular influence of the yeast strain was observed on the remaining non-anthocyanin phenolic compounds (i.e, hydroxybenzoic acids and flavanols). Pyranoanthocyanins and metabolites resulting from the alcoholic fermentation such as tyrosol and tryptophol, seemed to be more influenced by the must composition and pH, and thus, by the grape variety, than by the yeast strain.     

Phenolics and antioxidant properties of bayberry (Myrica rubra Sieb. et Zucc.) pomace

Five cultivars of Myrica rubra, Biqi, Wandao, Dongkui, Dingao, and Zaodamei, were collected to analyze the phenolic compounds and evaluate the antioxidant properties of bayberry pomaces. The main anthocyanin was cyanidin-3-o-glucoside (3073.3–6219.2 mg/kg dry weight (DW)) and the main flavonol was quercetin-3-o-glucoside (296.2–907.9 mg/kg dry weight). Quercetin and myricetin were also found in the bayberry pomaces, and quercetin deoxyhexoside and myricetin deoxyhexoside were tentatively identified. The dominant phenolic acids were gallic acid (102.9–241.7 mg/kg dry weight) and protocatechuic acid (29.5–57.2 mg/kg dry weight). Other phenolic acids such as p-hydroxybenzoic, vanillic, caffeic, p-coumaric, and ferulic acids were also present in the bayberry pomaces, whereas, chlorogenic acid was only detected in Dongkui (1.58 mg/kg dry weight). The antioxidant activity of Wandao was the strongest of the five cultivars, whereas the activity of Dongkui was the weakest, and a significant positive relationship was observed between antioxidant activity and total phenolic content or total anthocyanins.     

Antioxidant compounds and antioxidant capacity of Peruvian camu camu (Myrciaria dubia (H.B.K.) McVaugh) fruit at different maturity stages

The antioxidant capacities of ascorbic acid and phenolic compounds present in camu camu fruit were screened during ripening. Ascorbic acid decreased, and anthocyanin, flavonol and flavanol contents, and DPPH antioxidant capacity increased during ripening. Antioxidant compounds from camu camu were fractionated in two fractions: an ascorbic acid-rich fraction (F-I) and a phenolics-rich fraction (F-II). F-I was the major contributor to the DPPH antioxidant capacity (67.5–79.3%) and F-II played a minor role (20.7–32.5%). A total of 30 different phenolic compounds were detected by HPLC-PAD. The presence of catechin, delphinidin 3-glucoside, cyanidin 3-glucoside, ellagic acid and rutin was elucidated. Other phenolic compounds, such as flavan-3-ol, flavonol, flavanone and ellagic acid derivatives, were also present. For the three ripening stages the flavan-3-ols and ellagic acid group were the most representative phenolic compounds in this fruit. Acid hydrolysis of F-II revealed the presence mainly of gallic and ellagic acids, suggesting that camu camu fruit possesses important quantities of hydrolysed tannins (gallo- and/or ellagitannins). These results confirm that camu camu fruit is a promising source of antioxidant phenolics.     

Chemical composition,anthocyanins, non-anthocyanin phenolics and antioxidant activity of wild bilberry (Vaccinium meridionale Swartz) from Colombia

Berries of Vaccinium meridionale Swartz native to Colombia were analysed for chemical composition, total phenolic content, anthocyanin content, and antioxidant activity. In addition, high-performance liquid chromatography with photodiode array detection (HPLC–DAD) and HPLC-electrospray ionisation tandem mass spectrometry (ESI–MS/MS) were used to determine anthocyanin and phenolic composition. Anthocyanin content was 329.0 ± 28.0 mg cyanidin 3-glucoside equivalents/100 g (fresh weight) FW and total phenolic content was 758.6 ± 62.3 mg gallic acid equivalent/100 g FW. Cyanidin 3-galactoside was the major anthocyanin while the most abundant non-anthocyanin phenolic was chlorogenic acid.     

Characterisation of calamansi (Citrus microcarpa). Part I: Volatiles,aromatic profiles and phenolic acids in the peel

Volatile compounds in the peel of calamansi (Citrus microcarpa) from Malaysia, the Philippines and Vietnam were extracted with dichloromethane and hexane, and then analysed by gas chromatography–mass spectroscopy/flame ionisation detector. Seventy-nine compounds representing >98% of the volatiles were identified. Across the three geographical sources, a relatively small proportion of potent oxygenated compounds was significantly different, exemplified by the highest amount of methyl N-methylanthranilate in Malaysian calamansi peel. Principal component analysis and canonical discriminant analysis were applied to interpret the complex volatile compounds in the calamansi peel extracts, and to verify the discrimination among the different origins. In addition, four common hydroxycinnamic acids (caffeic, p-coumaric, ferulic and sinapic acids) were determined in the methanolic extracts of calamansi peel using ultra-fast liquid chromatography coupled to photodiode array detector. The Philippines calamansi peel contained the highest amount of total phenolic acids. In addition, p-Coumaric acid was the dominant free phenolic acids, whereas ferulic acid was the main bound phenolic acid.     

Variability in the saccharide,protein, phenolic acid and saponin contents of four market classes of edible dry beans

The content and composition of the saccharides, protein and amino acids, phenolic acids, and saponins of four market classes (navy, dark red kidney, pinto and Black Turtle Soup) of edible dry beans (Phaseolus vulgaris L) were determined. These compounds are potential precursors of flavour development in the processed beans and may contribute to the unique flavour characteristics of the various bean classes. The contents of sucrose and stachyose were significantly different (P < 0.05) for the four bean classes and ranged from 2.63 to 4.80 g per 100 g and 2–81 to 4–21 g per 100 g, respectively. Total nitrogen contents ranged from 3–92 to 4–71 g N per 100 g and were significantly different. The distribution of the amino acids was similar for the four bean classes. Coumaric, ferulic, sinapic and cinnamic acids were identified. The phenolic acid soluble esters were the predominant fraction, with lesser amounts of the free and insoluble phenolic acids. The total saponin contents of the bean classes were similar. Significant (P <0–05) differences in the distribution between the three major saponin components were observed.     

Free and bound phenolic compounds in leaves of pak choi (Brassica campestris L. ssp. chinensis var. communis) and Chinese leaf mustard (Brassica juncea Coss)

Eleven pak choi cultivars and two leaf mustard cultivars grown under field conditions in China were investigated for the free polyphenol content in their outer and inner leaves, as well as in their leaf blades and leaf stalks. In most cases, there were no significant differences between the hydroxycinnamic acid derivative and flavonoid derivative contents in the outer and inner leaves for the 13 cultivars. However, the contents of blades and stalks differed: hydroxycinnamic acids and flavonoids were present in greater amounts in the leaf blade than in the leaf stalk. Trace or small amounts of flavonoids were detected in the pak choi and leaf mustard stalks. Additionally, the bound phenolic contents of two pak choi cultivars and two leaf mustard cultivars were investigated. The concentrations of cell wall-bound phenolic compounds were higher in the leaf blade than in the leaf stalk under field conditions in China. These compounds represent only a minor portion of the total phenolic contents (flavonoids and hydroxycinnamic acids) in leaf stalks (0.81–1.18%) and leaf blades (0.05–0.08%) from fresh plant material. The storage of plant samples from four Chinese cabbage cultivars resulted, in most cases, in an increase of phenolic content, within six days, at 4 °C and 20 °C. The increase might have been triggered by post-harvest plant stresses, which stimulate the biosynthesis of polyphenols.     

Phase II enzyme induction and anti‐inflammatory effects of crude extracts and secondary fractions obtained from bran from five black glutinous rice cultivars

Methanolic extracts of bran from black glutinous rice cultivars were screened for potential health benefits using cellular bioassays for quinone reductase (QR) induction in murine hepatoma cells and inhibition of NO production in lipopolysaccharide (LPS)‐activated RAW 264.7 macrophages. Fractionation of the crude extract by semi‐preparative HPLC afforded respective fractions enriched in phenolic acids, anthocyanins and proanthocyanidins. The relative potency of QR induction was phenolic acids > proanthocyanidins > anthocyanins, and the activity of the crude extract was conserved among the aggregate of these fractions. In contrast, all three fractions were more potent than the crude extract in terms of anti‐inflammatory effect. This suggests synergism effects among anti‐inflammatory agents through partial purification. Inhibition of macrophage NO production by binary mixtures of gallic acid or caffeic acid with the anthocyanin‐rich fraction indicated potential synergism. These results warrant further efforts to identify the active agents and substantiate synergistic interactions through isobologram analysis.     

Phenolic compound content of fresh and dried figs (Ficus carica L.)

Eighteen fig cultivars commonly grown in the south-eastern Spain were collected in two crops (spring and summer) and their polyphenolic profile was determined. Fruit from the first crop generally showed higher phenolic values than those from the second. Higher concentrations of total phenolics were found in skin than in flesh. LC–UV-DAD/ESI-MSⁿ analysis of the figs pointed to a high anthocyanin content, mainly cyanidin-3-rutinoside, flavonols such as quercetin-rutinoside, phenolic acids such as chlorogenic acid and flavones like luteolin 6C-hexose-8C-pentose and apigenin-rutinoside. The c-glycosides have not been previously described in figs. Moreover, to compare intact proanthocyanidins and proanthocyanin cleavage products, an acid-catalysis was made in the presence of phloroglucinol (phloroglucinolysis) and the mean degree of polymerisation was calculated. Finally, three cultivars of dried figs were also studied.     

A simplified UV spectral scan method for the estimation of phenolic acids and antioxidant capacity in eggplant pulp extracts

The objective of this study was to determine if a simple UV spectral analysis method can be used as a screening tool to estimate the amount of phenolic acid and the antioxidant capacity of eggplant pulp extracts. Calibration curves for different concentrations of 5-O-caffeoylquinic acid standards were developed using UV spectral data, HPLC analysis, and ferric reducing antioxidant power (FRAP) assay. Seven different freeze-dried eggplant pulp samples belonging to different cultivars or grown under different environmental conditions along with single peel sample were selected as model substrates for this study. HPLC results, simple UV spectral scan data, and quantification of antioxidant capacity by FRAP assay in seven eggplant pulp extracts showed a strong correlation (R² > 0.9) between the three methods. These results suggest that the single absorption reading or a simple UV spectral scan can be used to estimate the concentration of phenolic acids and the antioxidant capacity in eggplant pulp extracts without peels. This screening tool can be potentially used to identify cultivars and growing conditions that influence phenolic acid content in eggplant samples.     

Phenolic profiles of in vivo and in vitro grown Coriandrum sativum L.

Coriandrum sativum L. is a source of a variety of polyphenols and other phytochemicals, related to its high antioxidant activity and to its use for indigestion, rheumatism, and prevention of lipid peroxidation damage. Plant cell cultures are a means to study or to produce some active metabolites, such as polyphenols. This technique was applied to the investigation of coriander, and a detailed analysis of individual polyphenols in vivo and in vitro grown samples was performed. The in vivo vegetative parts showed quercetin derivatives as the main flavonoids and quercetin-3-O-rutinoside (3296 mg/kg dw) was the main polyphenol found in this part of coriander. The fruits revealed only phenolic acids and derivatives, caffeoyl N-tryptophan hexoside (45.33 mg/kg dw) being the most abundant phenolic derivative. In vitro samples also gave a high diversity of polyphenols, being C-glycosylated apigenin (2983 mg/kg dw) the main compound. Anthocyanins were only found in clone A, which was certainly related to its purple pigmentation, and peonidin-3-O-feruloylglucoside-5-O-glucoside was the major anthocyanin found (1.70 μg/kg dw). In vitro culture can be used to explore new industrial, pharmaceutical, and medicinal potentialities, such as the production of secondary metabolites like flavonoids.     

Effects of phenolic compounds in blueberries and muscadine grapes on HepG2 cell viability and apoptosis

Although blueberries and muscadine grapes have high contents of polyphenols, few studies have been conducted to assess their potential effects on cancer cells. The objective of this study was to systematically evaluate the effects of different fractions of phenolic compounds in blueberries and muscadine grapes on HepG2 liver cancer cell viability and apoptosis. Three cultivars of blueberries (‘Briteblue’, ‘Tifblue’ and ‘Powderblue’) and four cultivars of muscadine grapes (‘Carlos’, ‘Ison’, ‘Noble’, and ‘Supreme’) were assessed in this study. Polyphenols were extracted and further separated into phenolic acids, tannins, flavonols, and anthocyanins using a HLB cartridge and LH-20 column. The major compounds of different fractions were characterized. The phenolic acid fractions of muscadine grapes and blueberries showed a 50% inhibition of HepG2 cell population growth at the level of 1–2 mg/mL. The greatest inhibitory effects were observed from the anthocyanin fractions with 50% inhibitions of cancer cell population growth at concentrations of 70–150 and 100–300 μg/mL in blueberries and muscadine grapes, respectively. The flavonol and tannin fractions showed intermediate activities. In addition, DNA fragmentation was measured by using a Cell Death Detection ELISA kit to assess the induction of apoptosis. The anthocyanin fraction resulted in a two- to fourfold increase in DNA fragmentation compared to control in both muscadine grapes and blueberries. These findings of inhibition of cancer cell growth and induction of apoptosis suggest that blueberries and muscadine grapes may contribute to reduction in liver cancer risk.     

Polyphenol content and antioxidant activity of California almonds depend on cultivar and harvest year

The polyphenol content and antioxidant activity of Nonpareil, Carmel, Butte, Sonora, Fritz, Mission, and Monterey almond cultivars harvested over three seasons in California were examined. LC–MS was employed to quantify 16 flavonoids and two phenolic acids in acidified methanol extracts of almond skins. The 3-year mean polyphenol content of cultivars ranged from 4.0 to 10.7 mg/100 g almonds. Isorhamnetin-3-O-rutinoside was the most abundant flavonoid, present at 28–49% of total polyphenols among cultivars. Almonds from 2006 and 2007 had 13% fewer polyphenols than 2005, but FRAP and total phenols were comparable. Cultivar, but not season, had a differential impact on individual polyphenol synthesis. Using the results of polyphenol, total phenol, and FRAP, multivariate analysis distinguished harvest years and most cultivars with 80% confidence. Flavonoid content and antioxidant activity of almonds may be more dependent on cultivar than on seasonal differences.