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PubMed2003

Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species.

A number of Plantago spp. especially P. major has long been used in the treatment of diseases such as infection, inflammation and cancer. In this study, we evaluated the immunomodulatory activities of five chemical classes of pure compounds obtained from the Plantago genus on human peripheral blood mononuclear cells (PBMC). Studies were conducted on lymphocyte transformation by BrdU immunoassay and secretion of interferon-gamma (IFN-gamma) using an ELISA assay. Results showed that the water-soluble compounds, namely aucubin, chlorogenic acid, ferulic acid, p-coumaric acid and vanillic acid, enhanced the activity of human lymphocyte proliferation and secretion of IFN-gamma. Among the water-insoluble compounds, with the exception of luteolin, both baicalein and baicalin showed an enhancement of the human PBMC. Although oleanolic acid and ursolic acid of the triterpenoids did not significantly affect the proliferation of PBMC, they exhibited a strong stimulation of IFN-gamma secretion. Linalool, a monoterpenoid, showed a similar immunomodulatory activity as the triterpenoids. The present study concludes that the tested compounds, which possess immunostimulating activities, may contribute to the traditional claims of Plantago-based natural products used in treating cancers and infectious diseases.

Adjuvants, Immunologic↗
PubMed2003

Effect of acute drought stress and time of harvest on phytochemistry and dry weight of St. John's wort leaves and flowers.

The phytochemistry and dry weight of cultivated St. John's wort are significantly influenced by acute drought stress and time of harvest. In this study, plants subjected to brief drought stress during both flower and seed development periods exhibited increased concentrations in 8 of the 10 phytochemicals examined in this study, including hypericin, pseudohypericin, chlorogenic acid, rutin, hyperoside, isoquercitrin, quercitrin, and quercetin. Increases ranged from 5% to 36% (hyperoside and rutin, respectively). Conversely, the concentrations of hyperforin and adhyperforin in flowers were decreased by an average of 10% in drought-stressed plants as compared to well-watered control plants. Acute drought stress decreased flower dry weight significantly during both drydown periods, although vegetative parameters (height, leaf dry weight and stem dry weight) were not adversely affected. While acute drought stress significantly altered the chemical yield in the leaves and flowers (phytochemical content x harvested dry weight), the time of harvest was the predominant factor determining phytochemical concentration in the organs of H. perforatum.

Adaptation, Physiological↗
PubMed2006

Modification of primary and secondary metabolism of potato plants by nitrogen application differentially affects resistance to Phytophthora infestans and Alternaria solani.

Potato plants ( SOLANUM TUBEROSUM L. cv. Indira) were grown at two levels of N supply in the greenhouse. Plants supplied with 0.8 g N per plant (high N variant) showed significantly increased biomass as compared to plants without additional N fertilisation (low N variant). C/N ratio was lower and protein content was higher in leaves of the high N variant. The concentration of chlorogenic acids and flavonols was significantly lower in leaves from the high N variant. Whereas resistance to ALTERNARIA SOLANI increased when plants were supplied with additional nitrogen, these plants were more susceptible to PHYTOPHTHORA INFESTANS. After infection with both pathogens, we found a strong induction of p-coumaroylnoradrenaline and p-coumaroyloctopamine, which are identified for the first time in potato leaves and are discussed as resistance factors of other solanaceous plants.

Alternaria↗
PubMed1998

Food constituents attenuate monoamine oxidase activity and peroxide levels in C6 astrocyte cells.

Glial cell monoamine oxidase (MAO) activity has been implicated as a contributor to oxidative neuronal damage associated with various neurodegenerative diseases. The attenuation of MAO activity may provide protection against oxidative neurodegeneration. In this investigation, the presence of MAO-B in rat C6 astrocyte cells was substantiated by dose-dependent inhibition of enzyme activity in the presence of chlorgyline-HCl and L-deprenyl. The present study evaluated various dietary-derived food constituents for evidence of inhibition on oxidative deamination of monoamines or peroxide radical trapping capacity. Results of this investigation indicate that compounds which inhibit C6 glial cell MAO enzyme activity or scavenge peroxide product include chlorogenic acid, (+)-catechin, taxifolin, (-)-epigallocatechin gallate (EGCG), fisetin, coenzyme Q0, curcumin, sesamol, morin, sesame oil, silymarin, green tea, ferulic acid, caffeic acid, and rutin hydrate. The results of this study indicate that dietary compounds can attenuate peroxide production in glial cells by either inhibiting the deamination of monoamines or acting as a free radical scavenger.

Animals↗
PubMed1992

Variation in Growth and Secondary Phenolics Among Field-Cultivated Clones of Salix myrsinifolia.

Nine S. MYRSINIFOLIA clones were studied for secondary phenolics and phytomass production in an old, unfertilized hayfield after the second growing season. S. MYRSINIFOLIA is one of the most promising willow species for the production of herbal drug material. Its salicylate content is moderately high in all parts of the shoot. The leaf and stem phytomass varied significantly among clones, but more than 70% of the total variation could be explained by within-clonal phytomass variation. Similarly, the accumulation of salicin, salicortin, chlorogenic acid (+)-catechin, proanthocyanidins, and unknowns varied significantly according to source (tissue, individual, or clone), and in most cases the environmental (within-clonal) variation was nearly as high as the genetic variation (between-clones). In the selection of the best clones for the production of herbal drug material three main factors should be taken account: costs of cultivation, costs for transportation, and costs for production of extracts. A high phytomass clone may be a low-quality clone as far as salicylates are concerned.

Journal Article↗
PubMed2004

Structural and functional divergence of insect CYP6B proteins: From specialist to generalist cytochrome P450.

How polyphagous herbivores cope with the diversity and unpredictability of plant defenses remains largely unknown at both the genetic and molecular levels. To examine whether generalist counterdefense enzymes are structurally more flexible and functionally more diverse, two counterdefensive allelochemical-metabolizing cytochrome P450 proteins, CYP6B1 from the specialist Papilio polyxenes, feeding on furanocoumarin-containing plants, and CYP6B8 from the generalist Helicoverpa zea, feeding on hundreds of host plant species, are compared structurally and functionally. Molecular modeling indicates that CYP6B8 has more flexible overall folding, a more elastic catalytic pocket, and one more substrate access channel than CYP6B1. Baculovirus-mediated expression of the CYP6B8 and CYP6B1 proteins demonstrates that CYP6B8 metabolizes six biosynthetically diverse plant allelochemicals (xanthotoxin, quercetin, flavone, chlorogenic acid, indole-3-carbinol, and rutin) and three insecticides (diazinon, cypermethrin, and aldrin), whereas CYP6B1 metabolizes only two allelochemicals (xanthotoxin and flavone) and one insecticide (diazinon) of those tested. These results indicate that generalist counterdefense proteins are capable of accepting a more structurally diverse array of compounds compared with specialist counterdefense proteins.

Amino Acid Sequence↗
PubMed2001

Adesmia aegiceras: antimicrobial activity and chemical study.

The antimicrobial activity of the ethanolic extract of Adesmia aegiceras was studied by the agar-well diffusion method. Antibacterial activity against Micrococcus luteus and eight pathogenic bacterial strains as well as antifungal activity against Candida albicans, was detected. Bacterial and fungal strains exhibited similar concentration-response curves (EC50 and Rmax values) and similar MIC. The MBC/MIC was about 8. These data would indicate the potential usefulness of the A. aegiceras extract as a microbiostatic, antiseptic or disinfectant agent. Furthermore, chemical study of the bioactive alcoholic extract was performed, which revealed quercetin, isorhamnetin-3-rutinoside, isovitexin, pinitol and chlorogenic acid as its main components.

Anti-Bacterial Agents↗
PubMedDate not supplied

PTP1B inhibitors from Saussrurea lappa.

A new lignan glycoside, named 1,5-dihydroxypinoresinol-4'-O-beta-d-glucopyranoside (1), has been isolated from the EtOH extract of the roots of Saussurea lappa, together with twenty known compounds: (+)-1-hydroxypinoresinol-1-O-beta-D-glucopyranoside (2), fraxiresinol-4'-O-beta-D-glucopyranoside (3), (-)-olivil-4''-O-beta-D-glucopyranoside (4), 4-allyl-2,6-dimethoxybenzene-1-O-beta-D-glucopyranoside, syringin, costunolide-15-O-beta-D-glucopyranoside, chlorogenic acid, aloe-emodin-8-O-beta-D-glucopyranoside (5), rhein-8-O-beta-D-glucopyranoside (6), chrysophanol (7), emodin, dehydrocostus lactone, costunolide, beta-costic acid, reynosin, arbusculin A, alpha-cyclocostunolide, beta-cyclocostunolide, santamarine and magnolialide. Three anthraquinones (5-7) showed moderate bioactivity against human Protein Tyrosine Phosphatase 1B (hPTP1B) in vitro.

Anthraquinones↗
PubMed2002

Effects of food processing on flavonoids and lycopene status in a Mediterranean tomato variety.

This research is focused on the antioxidant properties of dietary components, in particular phenolics and carotenoids and the assessment of the contribution of the combined antioxidants to the total antioxidant activity (TAA) of tomato fruit. The aim of this study was to analyse the effects of processing on the antioxidant properties of tomato. The effects of three different methods of processing fresh tomatoes into tomato sauce were investigated with respect to the antioxidant properties of the fruit. Identification and quantification of the main carotenoids and flavonoids present in tomatoes was achieved by HPLC analysis and the effect on the concentration and availability of these compounds was investigated at different stages of the processing. The processing affected mainly naringenin causing a reduction in the concentration. Conversely, levels of chlorogenic acid were increased suggesting an improvement in availability of this compound to extraction. The concentration of all-trans-lycopene was also increased following processing. Less than 10% isomerisation of all-trans-lycopene to the cis form was detected for all the methods analysed. The effects of processing on the overall antioxidant activity support the theory of a general improvement in availability of individual antioxidants. For both hydrophilic and lipophilic extracts TAA values were increased.

Antioxidants↗
PubMed2003

Grape and grape seed extract capacities at protecting LDL against oxidation generated by Cu2+, AAPH or SIN-1 and at decreasing superoxide THP-1 cell production. A comparison to other extracts or compounds.

A large body of evidence supports the key role of oxidized low-density lipoprotein in atherosclerosis. The aim of this study was to compare the capacity of natural polyphenols (PP) from Vitis vinifera and Olea europea at protecting LDL against oxidation brought about by Cu2+, oxygen-centered radical-generating AAPH, or peroxynitrite-generating SIN-1 in vitro systems, or at impairing superoxide production in promonocyte cells (THP-1) conveniently differentiated into adherent macrophages. PP were either from the whole grape (fraction A) containing mainly procyanidins, (epi)-catechin and anthocyanins, or from grape seed extracts (fractions B and C) consisting of tannins and procyanidin oligomers with a higher content in B than in C, or from a grape skin extract (fraction D) consisting mainly of anthocyanins, or from a hydrosoluble olive mill wastewater PP extract (fraction E) containing hydroxytyrosol and oleuropein. Chlorogenic acid (F) and catechin (G) were taken as archetypes of PP preventing oxidation partly as copper scavenger and as radical scavenger only, respectively. All grape fractions were efficient towards Cu2+ system (equally or more efficient than F), whereas they were rather poorly efficient towards AAPH and SIN-1 (less efficient than G but as efficient as F). Among the PP fractions, B was the most effective at protecting LDL in the SIN-1 system and at impairing THP-1 superoxide production. Taken together, these data suggest that the PP fraction from grape seed rich in procyanidins achieves the best compromise between the direct and indirect (i.e. cell-mediated) types of action in protecting LDL against oxidation, strengthening the need for improving the knowledge of its bioavailability in humans.

Amidines↗
PubMed2001

Chemical composition and potential health effects of prunes: a functional food?

Prunes are dried plums, fruits of Prunus domestica L., cultivated and propagated since ancient times. Most dried prunes are produced from cultivar d'Agen, especially in California and France, where the cultivar originated. After harvest, prune-making plums are dehydrated in hot air at 85 to 90 degrees C for 18 h, then further processed into prune juice, puree, or other prune products. This extensive literature review summarizes the current knowledge of chemical composition of prunes and their biological effects on human health. Because of their sweet flavor and well-known mild laxative effect, prunes are considered to be an epitome of functional foods, but the understanding of their mode of action is still unclear. Dried prunes contain approximately 6.1 g of dietary fiber per 100 g, while prune juice is devoid of fiber due to filtration before bottling. The laxative action of both prune and prune juice could be explained by their high sorbitol content (14.7 and 6.1 g/100 g, respectively). Prunes are good source of energy in the form of simple sugars, but do not mediate a rapid rise in blood sugar concentration, possibly because of high fiber, fructose, and sorbitol content. Prunes contain large amounts of phenolic compounds (184 mg/100 g), mainly as neochlorogenic and chlorogenic acids, which may aid in the laxative action and delay glucose absorption. Phenolic compounds in prunes had been found to inhibit human LDL oxidation in vitro, and thus might serve as preventive agents against chronic diseases, such as heart disease and cancer. Additionally, high potassium content of prunes (745 mg/100 g) might be beneficial for cardiovascular health. Dried prunes are an important source of boron, which is postulated to play a role in prevention of osteoporosis. A serving of prunes (100 g) fulfills the daily requirement for boron (2 to 3 mg). More research is needed to assess the levels of carotenoids and other phytochemicals present in prunes to ensure correct labeling and accuracy of food composition tables in order to support dietary recommendations or health claims.

Boron↗
PubMed2006

Coffee, diabetes, and weight control.

Several prospective epidemiologic studies over the past 4 y concluded that ingestion of caffeinated and decaffeinated coffee can reduce the risk of diabetes. This finding is at odds with the results of trials in humans showing that glucose tolerance is reduced shortly after ingestion of caffeine or caffeinated coffee and suggesting that coffee consumption could increase the risk of diabetes. This review discusses epidemiologic and laboratory studies of the effects of coffee and its constituents, with a focus on diabetes risk. Weight loss may be an explanatory factor, because one prospective epidemiologic study found that consumption of coffee was followed by lower diabetes risk but only in participants who had lost weight. A second such study found that both caffeine and coffee intakes were modestly and inversely associated with weight gain. It is possible that caffeine and other constituents of coffee, such as chlorogenic acid and quinides, are involved in causing weight loss. Caffeine and caffeinated coffee have been shown to acutely increase blood pressure and thereby to pose a health threat to persons with cardiovascular disease risk. One short-term study found that ground decaffeinated coffee did not increase blood pressure. Decaffeinated coffee, therefore, may be the type of coffee that can safely help persons decrease diabetes risk. However, the ability of decaffeinated coffee to achieve these effects is based on a limited number of studies, and the underlying biological mechanisms have yet to be elucidated.

Animals↗
PubMed2007

Solar ultraviolet-B radiation and insect herbivory trigger partially overlapping phenolic responses in Nicotiana attenuata and Nicotiana longiflora.

BACKGROUND AND AIMS: Plants exposed to solar ultraviolet-B radiation (UV-B, 280-315 nm) frequently suffer less insect herbivory than do plants that receive attenuated levels of UV-B. This anti-herbivore effect of solar UV-B exposure, which has been documented in several ecosystems, is in part mediated by changes in plant tissue quality. Exposure to UV-B can modify the abundance of a number of secondary metabolites, including phenolic compounds with potential impacts on insect herbivores. The aim of this study is to assess the potential anti-herbivore role of UV-B-induced phenolic compounds by comparing the phenolic profiles induced by UV-B and simulated insect herbivory in two wild species of the genus Nicotiana. METHODS: Plants grown under field and glasshouse conditions were exposed to contrasting levels of UV-B. Half of the plants of the attenuated UV-B treatment were given a simulated herbivory treatment, where leaves were mechanically damaged and immediately treated with oral secretions of Manduca sexta caterpillars. This treatment is known to mimic the impact of real herbivory on the expression of plant defences in Nicotiana. Phenolic profiles induced by UV-B and simulated herbivory were characterized using high-performance liquid chromatography-mass spectrometry (HPLC-MS). KEY RESULTS: UV-B induced the accumulation of several UV-absorbing phenolic compounds that are known to play a significant role in UV-B screening. Interestingly, there was a significant convergence in the phenolic profiles induced by UV-B and simulated herbivory: chlorogenic acid and dicaffeoylspermidine isomers, in particular, displayed a similar pattern of response to these stimuli. In contrast, rutin, the only flavonoid that accumulated in significant quantities in the experiments, was only induced by UV-B. CONCLUSIONS: The results suggest that the anti-herbivory effect induced by UV-B may be mediated at least in part by the accumulation of phenylpropanoid derivatives that are similar to those induced by the plant in response to insect herbivory.

Animals↗
PubMed2006

Down-regulation of cinnamoyl-CoA reductase in tomato (Solanum lycopersicum L.) induces dramatic changes in soluble phenolic pools.

Health-beneficial properties of many secondary plant metabolites have created much interest into the control of their biosynthesis in crop species. Phenolic compounds, including flavonoids, hydroxycinnamates, and tannins, make up an important group of such phytonutrients. They are formed via the phenylpropanoid pathway and share common precursors with lignin, an insoluble cell wall-associated polymer. In this study, the aim was to reduce lignin biosynthesis so as to enhance the availability of these precursors and, thereby, stimulate the production of soluble, potentially health-promoting, phenolic compounds in tomato (Solanum lycopersicum L.). First two tomato genes encoding cinnamoyl-CoA reductase (CCR), a key enzyme in the formation of lignin monomers, were identified and characterized. Transgenic plants exhibiting a reduced lignin content were subsequently obtained through an RNAi strategy targeting one of these genes. As anticipated, the total level of soluble phenolics was higher in stems and leaves of the transformants as compared with control plants. This was correlated with an increased antioxidant capacity of the corresponding plant extracts. Analysis of the soluble phenolic fraction by HPLC-MS revealed that vegetative organs of CCR down-regulated plants contained higher amounts of chlorogenic acid and rutin, and accumulated new metabolites undetectable in the wild type, such as N-caffeoyl putrescine and kaempferol rutinoside. In fruits, CCR down-regulation triggered the moderate accumulation of two new compounds in the flesh, but the total phenolic content was not affected. Although the prospects of exploiting such a strategy for crop improvement are limited, the results provide further insight into the control of the phenylpropanoid pathway in the Solanaceae.

Aldehyde Oxidoreductases↗
PubMed1984

Partial purification and characterization of UDPG:t-cinnamate glucosyltransferase in the root of sweet potato, Ipomoea batatas Lam.

Previously, we isolated t-cinnamoyl-D-glucose as a possible intermediate in chlorogenic acid biosynthesis from sweet potato root. The enzyme which catalyzes the formation of t-cinnamoyl-D-glucose has been purified 539-fold from sweet potato root (Ipomoea batatas Lam.) and characterized. It required UDP-glucose as a glucosyl donor. Its molecular weight was estimated to be 45,000 by gel filtration chromatography through Sephadex G-100. Its Km values were 0.2 mM for t-cinnamic acid and 0.1 mM for UDP-glucose. It also showed activity toward various aromatic carboxylic acids other than t-cinnamic acid with the following relative activities at the concentration of 1.8 mM: t-cinnamic acid, 100; p-coumaric acid, 57; o-coumaric acid, 52; caffeic acid, 15; benzoic acid, 71; ferulic acid, 27; 4-hydroxyl-3-methoxy-benzoic acid, 35. When p-coumaric acid was used as a substrate, the enzyme introduced the glucosyl group exclusively to a carboxyl group, not to a hydroxyl group on a benzene ring. It was inhibited by p-chloromercuribenzoate and HgCl2. Its activity in the extract from sliced root decreased during the first 28 h after slicing, then increased to the original level by 75 h. The apparent decrease seemed to be caused by the appearance of an inhibitory factor of high molecular weight in the tissue extract.

Chemical Phenomena↗
PubMed2000

Histological alterations in the intestinal epithelium caused by the inclusion of full-fat sunflower kernels in broiler chicken diets.

Changes in small intestinal morphology (jejunum) were examined at 28 d of age in chicks fed with full-fat sunflower kernels (FFSK)-based diets. Jejunal mucosa of chicks (six chicks per treatment) were embedded in Epon-812 for examination by a conventional electron microscope procedure. A portion of the tissues was also sectioned and embedded in paraffin for examination by light microscopy. Brush border, goblet cells, and intraepithelial lymphocytes, on the one hand, and fibroblast and mononuclear cells (lymphocytes, plasma cells, macrophages) were observed in the enterocytes and lamina propria, respectively. The results showed that the birds fed 150 g kg(-1) of FFSK showed a shortening and thickening of the villi, hyperplasia and vacuolar degeneration of enterocytes, and hypertrophy and hyperplasia of goblet cells. Likewise, an increment of intraepithelial lymphoid cells and hypercellularity of the lamina propria was observed. In addition, electron microscopy showed large vacuoles in the enterocytes, which could be dilations of agranular and granular endoplasmic reticulum or Golgi. There were many dark granules within the vacuoles that could be triglyceride-rich lipoproteins (portomicrons). These lesions could have been due to the presence of chlorogenic acid or to the greater concentration of oil in the FFSK diet. Our observations demonstrated that addition of 150 g kg(-1) FFSK to broiler chicken diets caused alterations in jejunal mucosa that could explain the decrease in fat digestibility observed in a previous experiment in which we incorporated FFSK into broiler diets.

Animals↗
PubMed2003

Tomato and garlic can modulate azoxymethane-induced colon carcinogenesis in rats.

Tomato (Lycopersicon esculentum) and garlic (Allium cepa) are important constituents of the human diet. Compounds like diallyl sulfides, diallyl disulfides and quercetin, which are active components of garlic, have known anti-inflammatory, antimutagenic activities. Similarly, active components in tomato, such as kaempferol and chlorogenic acid, have antimutagenic activities and lycopene is the most active oxygen quencher with potential chemopreventive activities. In view of this, an endeavour was made to evaluate the anticarcinogenic effect, if any, of tomato and garlic consumption individually and in combination on azoxymethane-induced colonic precancerous lesion, the aberrant crypt foci in animal model. Sprague-Dawley rats (4-5 weeks old) were injected with azoxymethane (15 mg/kg b.w.) and orally administered with 2% (w/v) of tomato, garlic and a combination of both. After 12 weeks of first azoxymethane injection, colons were assessed for aberrant crypt foci and compared with the carcinogen control group. Lipid peroxidation level and glutathione-S-transferase (GST) activity were assessed in liver as well as in colon. Furthermore, in situ cell proliferation and apoptosis were estimated using the Brdu incorporation method and TUNEL method respectively. It was observed that aberrant crypt foci were reduced in all treated groups (by 32.11% in garlic, by 76.14% in tomato and by 55.96% in the combination group). Among treated groups, GST activity was found to be induced in both liver and colon, whereas considerable reduction in lipid peroxidation level was observed in liver as well as in colon with respect to the carcinogen control group. Significant reduction in Brdu labelling index and increase in apoptotic index in colon was noted in the treated groups. These results suggest that tomato and garlic suspensions have a protective effect on colon carcinogenesis, which is mediated by modulation of different biological pathways during carcinogenesis.

Animals↗
PubMed2004

Metabolic discrimination of Catharanthus roseus leaves infected by phytoplasma using 1H-NMR spectroscopy and multivariate data analysis.

A comprehensive metabolomic profiling of Catharanthus roseus L. G. Don infected by 10 types of phytoplasmas was carried out using one-dimensional and two-dimensional NMR spectroscopy followed by principal component analysis (PCA), an unsupervised clustering method requiring no knowledge of the data set and used to reduce the dimensionality of multivariate data while preserving most of the variance within it. With a combination of these techniques, we were able to identify those metabolites that were present in different levels in phytoplasma-infected C. roseus leaves than in healthy ones. The infection by phytoplasma in C. roseus leaves causes an increase of metabolites related to the biosynthetic pathways of phenylpropanoids or terpenoid indole alkaloids: chlorogenic acid, loganic acid, secologanin, and vindoline. Furthermore, higher abundance of Glc, Glu, polyphenols, succinic acid, and Suc were detected in the phytoplasma-infected leaves. The PCA of the (1)H-NMR signals of healthy and phytoplasma-infected C. roseus leaves shows that these metabolites are major discriminating factors to characterize the phytoplasma-infected C. roseus leaves from healthy ones. Based on the NMR and PCA analysis, it might be suggested that the biosynthetic pathway of terpenoid indole alkaloids, together with that of phenylpropanoids, is stimulated by the infection of phytoplasma.

Catharanthus↗