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Background: Plantago ovata, commonly called psyllium, is known to be a rich source of polyphenolic compounds. The present study was aimed at determining polyphenol content and studying their antioxidant activities in P. ovata during in vitro callus culture. An attempt was also made to enhance polyphenol content using external additives. The role of PAL gene in polyphenol accumulation was also studied., Results: The study indicated the presence of significant amounts of polyphenols, including flavonoids, in P. ovata callus. A gradual increase in polyphenol and flavonoid content was observed up to the third passage (63 days) of callus culture, which declined at the next passage. The third-passage callus showed highest antioxidant activity. High-performance liquid chromatographic results indicated the presence of high amounts of gallic acid and rutin in P. ovata calli; however, other polyphenols were also present but to a lesser extent. Additive supplementation was effective in enhancing polyphenol production and in increasing antioxidant activity in P. ovata callus., Conclusion: The present research reported accumulation of polyphenols in callus culture of P. ovata, which could be applied to isolation of polyphenols for various beneficial purposes. It also indicated enhancement in the production of several polyphenols and also an increase in antioxidant activity in the additive-treated callus., (© 2015 Society of Chemical Industry.)

The impact of tropical seasons (dry and wet) and growth stages (8, 10 and 12 weeks) of Cosmos caudatus on the antioxidant activity (AA), total phenolic content (TPC) as well as the level of bioactive compounds were evaluated using high performance liquid chromatography (HPLC). The plant morphology (plant height) also showed variation between the two seasons. Samples planted from June to August (during the dry season) exhibited a remarkably higher bioactivity and height than those planted from October to December (during the wet season). The samples that were harvested at eight weeks of age during the dry season showed the highest bioactivity with values of 26.04 g GAE/100 g and 22.1 μg/ml for TPC and IC₅₀, respectively. Identification of phytochemical constituents in the C. caudatus extract was carried out by liquid chromatography coupled with diode array detection and electrospray tandem mass (LC-DAD-ESIMS/MS) technique and the confirmation of constituents was achieved by comparison with literature data and/or co-chromatography with authentic standards. Six compounds were indentified including quercetin 3-O-rhamnoside, quercetin 3-O-glucoside, rutin, quercetin 3-O-arabinofuranoside, quercetin 3-O-galactoside and chlorogenic acid. Their concentrations showed significant variance among the 8, 10 and 12-week-old herbs during both seasons.

Physiological and molecular mechanisms underlying quantitative resistance of plants to pathogens are still poorly understood, but could depend upon differences in the intensity or timing of general defense responses. This may be the case for the biosynthesis of phenolics which are known to increase after elicitation by pathogens. We thus tested the hypothesis that differences in quantitative resistance were related to differential induction of phenolics by pathogen-derived elicitors. Five potato cultivars (Solanum tuberosum, L.) spanning a range of quantitative resistance were treated with a concentrated culture filtrate (CCF) of Phytophthora infestans or purified lipopolysaccharides (LPS) from Pectobacterium atrosepticum. The kinetic of phenolics accumulation was followed and a set of typical phenolics was identified: chlorogenic acid, phenolamides and flavonols including rutin (quercetin-3-O-rutinoside) and nicotiflorin (kaempferol-3-O-rutinoside). Our results showed that CCF but not LPS induced differential accumulation of major phenolics among cultivars. Total phenolics were related with resistance to P. atrosepticum but not to P. infestans. However, nicotiflorin was inversely related with resistance to both pathogens. Rutin, but not nicotiflorin, inhibited pathogen growth in vitro at physiological concentrations. These data therefore suggest that (i) several phenolics are candidate markers for quantitative resistance in potato, (ii) some of these are pathogen specific although they are produced by a general defense pathway, (iii) resistance marker molecules do not necessarily have antimicrobial activity, and (iv) the final content of these target molecules-either constitutive or induced-is a better predictor of resistance than their inducibility by pathogen elicitors., (Copyright © 2012 Elsevier Masson SAS. All rights reserved.)

Objective: We verified the hypothesis that the consumption of polyphenol concentrate (PC), rich in quercetin and its glycosides (36 g/100 g), in association with different dietary fiber matrices, that is, an easily fermentable fructo-oligosaccharides (FOS) or non-fermentable cellulose (CEL), causes a disparate adaptive response of the cecal microbial activity in rats. This in turn facilitates further utilization of biologically active polyphenolic compounds, which are not, as usual, digested in the foregut., Methods: Four-week experimental feeding of male Wistar rats consisted of diets containing 5% FOS or CEL, as a source of dietary fiber, with or without 0.3% addition of PC., Results: Positive changes in rat cecum were observed resulting from the ingestion of an FOS-containing diet, such as decreased pH and increased the production of short-chain fatty acids in the digesta, compared with a CEL-containing diet. The addition of PC to the FOS diet did not eliminate the positive effects of the latter, except for a slight increase in cecal pH and a decrease in microbial glycolytic activity. However, a simultaneous increase in the cecal butyrate pool was also observed. An adaptation process of the microflora enzymatic system to dieting with PC and FOS was proven in further enhanced susceptibility of rutin (quercetin 3-O-glucorhamnoside), hyperoside (quercetin 3-O-galactoside), and quercitrin (quercetin 3-O-rhamnoside) to hydrolysis by the cecal digesta solution., Conclusion: Especially when consumed together, PC and FOS are important dietary factors affecting the susceptibility of quercetin glycosides to microbial metabolism in the cecum. The intensification of the hydrolysis of quercetin glycosides by dietary treatments leads also to the increased metabolism of quercetin itself., (Copyright © 2011 Elsevier Inc. All rights reserved.)

Zingiber officinale Roscoe. (Family Zingiberaceae) is well known in Asia. The plant is widely cultivated in village gardens in the tropics for its medicinal properties and as a marketable spice in Malaysia. Ginger varieties are rich in physiologically active phenolics and flavonoids with a range of pharmacological activities. Experiments were conducted to determine the feasibility of increasing levels of flavonoids (quercetin, rutin, catechin, epicatechin, kaempferol, naringenin, fisetin and morin) and phenolic acid (gallic acid, vanillic acid, ferulic acid, tannic acid, cinnamic acid and salicylic acid), and antioxidant activities in different parts of Malaysian young ginger varieties (Halia Bentong and Halia Bara) with CO(2) enrichment in a controlled environment system. Both varieties showed an increase in phenolic compounds and flavonoids in response to CO(2) enrichment from 400 to 800 µmol mol-1 CO(2). These increases were greater in rhizomes compared to leaves. High performance liquid chromatography (HPLC) results showed that quercetin and gallic acid were the most abundant flavonoid and phenolic acid in Malaysian young ginger varieties. Under elevated CO(2) conditions, kaempferol and fisetin were among the flavonoid compounds, and gallic acid and vanillic acid were among the phenolic compounds whose levels increased in both varieties. As CO(2) concentration was increased from 400 to 800 µmol mol-1, free radical scavenging power (DPPH) increased about 30% in Halia Bentong and 21.4% in Halia Bara; and the rhizomes exhibited more enhanced free radical scavenging power, with 44.9% in Halia Bentong and 46.2% in Halia Bara. Leaves of both varieties also displayed good levels of flavonoid compounds and antioxidant activities. These results indicate that the yield and pharmaceutical quality of Malaysian young ginger varieties can be enhanced by controlled environment production and CO(2) enrichment.

This work describes the isolation of the secondary metabolites identified as the quinonemethides maytenin (1) and pristimerin (2) from Maytenus ilicifolia extracts obtained from root barks of adult plants and roots of seedlings and their quantification by high performance liquid chromatography coupled to a diode array detector. The electrochemical profiles obtained from cyclic voltammetry and a coulometric detector coupled to high-performance liquid chromatography contributed to the evaluation of their antioxidant capacity. The antioxidant properties of individual components and the crude extracts of the root barks of Maytenus ilicifolia were compared and the possible synergistic associations of quinonemethide triterpenes and phenolic substances were investigated by using rutin as a model phenolic compound.

The non-enzymatic repair of DNA oxidative damage can occur in a purely chemical system, but data show that it might also occur in cells. Human hepatoma cells (SMMC-7721) and human hepatocyte cells (LO2) were treated with 200microM H(2)O(2) for 30min to induce oxidative DNA damage quantified by amount of 8-OHdG and degree of DNA strand breaks, without inducing enzymatic repair. The dynamics of enzymatic repair activity quantified by unscheduled DNA synthesis, within 30min after removal of H(2)O(2) enzymatic repair mechanism has not been initiated. However, pre-incubation with low micromolar level polyphenols, quercetin or rutin can significantly attenuate DNA damage in both cell lines, indicating that the polyphenols did not work through an enzymatic mechanism. Unscheduled DNA synthesis after removal of H(2)O(2) was also markedly decreased by quercetin and rutin. Combined with our previous studies of fast reaction chemistry, the inhibitory effect of polyphenols have to be assigned to non-enzymatic repair mechanism rather than to enzymatic repair mechanism or antioxidant mechanism.

There is a growing interest in the metabolic engineering of plant with increased desirable polyphenols such as chlorogenic acid (CGA) and rutin. In this study, the effects of overexpression of both phenylalanine ammonia lyase (AtPAL2), the first enzyme of the phenylpropanoid pathway, and hydroxycinnamoyl-CoA quinate:hydroxycinnamoyl transferase (NtHQT), the last enzyme of CGA biosynthesis, and the overexpression of AtPAL2 together with silencing of NtHQT were investigated in tobacco. Transgenic tobacco plants overexpressing AtPAL2 showed two and five times increases of CGA and rutin levels than the wild-type (WT) plants, respectively. Overexpression of NtHQT further increases the accumulation of CGA in the AtPAL2 plants to about three times than that of the WT level, while silencing of NtHQT in AtPAL2 plants results in about 12 times increase in rutin level than that of the WT plants. Simultaneous overexpression of phenylalanine ammonia lyase (PAL) and overexpression/silencing HQT could be used for the production of functional food with increased polyphenols.

Diabetic hyperglycaemia promotes the production of advanced glycation end-products (AGEs), which play a significant role in the development of complications associated with type 2 diabetes mellitus. Vaccinium angustifolium, a medicinal plant used for the treatment of diabetes, produces a variety of phenolic metabolites with putative anti-diabetic activities. To assess optimal cultivation time, seasonal changes in the concentration of six phenolic compounds in leaves and twelve compounds in stems were examined using HPLC-DAD and examined in relation to seasonal changes in AGE inhibition activity, assessed with a fluorescence-based assay. A seasonal decline occurred in the concentration of chlorogenic acid, rutin, and quercetin 3-arabinoside in leaves and chlorogenic acid in stems. The concentration of (+)-catechin, and (-)-epicatechin in stems declined within two weeks before rising and fluctuating insignificantly. AGE inhibition activity of leaves was significantly greater at the final compared to the initial collection date whereas the activity of stems did not change significantly. Relative to the leaf extract, the stem was a more potent inhibitor of AGE formation, which could be a result of the unique phytochemistry of stems. Together, these results revealed significant seasonal variation in the phenolic profile and anti-glycation effects of V. angustifolium extracts and indicated late summer as the collection time yielding optimal activity.

The noncovalent binding of selected phenolic compounds (chlorogenic-, ferulic-, gallic acid, quercetin, rutin, and isoquercetin) to proteins (HSA, BSA, soy glycinin, and lysozyme) was studied by an indirect method applying the quenching of intrinsic tryptophan fluorescence. From the data obtained, the binding constants were calculated by nonlinear regression (one site binding; y = Bx/k + x). It has been reported that tannins inhibit human salivary amylase and that these complexes may reduce the development of cariogenic plaques. Further, amylase contains two tryptophan residues in its active site. Therefore, in a second part of the study involving 31 human subjects, evidence was sought for noncovalent interactions between the phenols of green tea and saliva proteins as measured by the fluorescence intensity. Amylase activity was determined before and after the addition of green tea to saliva of 31 subjects. Forty percent of the subjects showed an increase in amylase activity contrary to studies reporting only a decrease in activity. The interactions of tannin with amylase result in a decrease of its activity. It still remains to be elucidated why amylase does not react uniformly under conditions of applying green tea to saliva. Further, in terms of using phenols as caries inhibitors this finding should be of importance.

Dietary phenols are antioxidants, and their consumption might contribute to the prevention of cardiovascular disease. Coffee and tea are major dietary sources of phenols. Dietary phenols are metabolized extensively in the body. Lack of quantitative data on their metabolites hinders a proper evaluation of the potential biological effects of dietary phenols in vivo. The aim of this study was to identify and quantify the phenolic acid metabolites of chlorogenic acid (major phenol in coffee), quercetin-3-rutinoside (major flavonol in tea) and black tea phenols in humans, and determine the site of metabolism. Healthy humans (n = 20) with an intact colon participated in a dietary controlled crossover study, and we identified and quantified approximately 60 potential phenolic acid metabolites in urine. Half of the ingested chlorogenic acid and 43% of the tea phenols were metabolized to hippuric acid. Quercetin-3-rutinoside was metabolized mainly to phenylacetic acids, i.e., 3-hydroxyphenylacetic acid (36%), 3-methoxy-4-hydroxyphenylacetic acid (8%) and 3,4-dihydroxyphenylacetic acid (5%). In contrast, in seven humans without a colon, we found only traces of phenolic acid metabolites in urine after they had ingested chlorogenic acid and quercetin-3-rutinoside. This implies that the colonic microflora convert most of these dietary phenols into metabolites that then reach the circulation. Metabolites of dietary phenols have lower antioxidant activity than their parent compounds; therefore, the contribution of dietary phenols to antioxidant activity in vivo might be lower than expected from in vitro tests.

Dietary phenolic cinnamic acids are hydrogenated in the side-chain, demethylated and dehydroxylated in the rumen and are responsible for the large urinary output of benzoic acid by ruminants. 2. Decarboxylation of phenolic acids to simple phenols is another reaction of the intestinal microflora and experiments were made to determine the extent of this reaction in the rumen of sheep. 3. In five experiments phenolic compounds, quinic acid or casein were infused into the rumen or abomasum of sheep and increments in urinary outputs of phenolic acids and phenols determined by thin-layer and gas-liquid chromatography. 4. Production of phenols was almost exclusively confined to reactions in the rumen. 5. Rumen administration of phenolic benzoic or phenylacetic acids which contained a 4-hydroxy substituent yielded large increments in urinary phenol outputs. Other phenolic benzoic and phenylacetic acids were not decarboxylated. Rumen decarboxylation of 4-hydroxy-3-phenylpropionic acid did not occur and decarboxylation of 4-hydroxycinnamic acids was slight. 6. Nearly half the tyrosine content of rumen-administered casein was excreted as p-cresol, a decarboxylation product of 4-hydroxyphenylacetic acid, p-Cresol was the principal phenol found in sheep urine. 7. Catechol and phenol were consistently found in sheep urine samples and p-ethylphenol, resorcinol, quinol, 4-methylcatechol, orcinol and pyrogallol were also found when suitable precursors were infused to the rumen. 8. It is concluded that p-cresol is a rumen metabolite of tyrosine. The other phenols found are microbial metabolites of phenolic precursors which are either widely distributed in plants such as 4-hydroxybenzoic, protocatechuic and vanillic acids or of more limited distribution such as the orcinol glycosides of some Ericaceous plants.