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[Hydroxycinnamic acid levels of various batches from mugwort flowering tops].

Dried flowering tops of 24 harvested batches (Artemisia vulgaris: 13; Artemisia verlotiorum: 11) and 12 batches of mugwort from commercial origin were examined. The levels of principal compounds averaged respectively: total hydroxycinnamic acids 6.09; 10.29 and 9.13%, chlorogenic acid 0.79; 2.05 and 1.35%, 1,5-dicaffeoylquinic acid 0.51; 4.01 and 1.25%, 3,5-dicaffeoylquinic acid 2.21; 1.25 and 2.60%. Specifications were discussed for an European Pharmacopoeial monography.

Artemisia↗

o-Quinones formed in plant extracts. Their reaction with bovine serum albumin.

1. The reactions between chlorogenoquinone, the o-quinone formed during the oxidation of chlorogenic acid, and bovine serum albumin depend on the ratio of reactants. 2. When the serum albumin is in excess, oxygen is not absorbed and the products are colourless. This reaction probably involves the thiol group of bovine serum albumin; it does not occur with bovine serum albumin which has been treated with p-chloromercuribenzoate, iodoacetamide or Ellman's reagent. 3. When bovine serum albumin reacts with excess of chlorogenoquinone, oxygen is absorbed and the products are red. The red colour is probably formed by reaction of the lysine in-amino groups of bovine serum albumin, as it is prevented by treating the protein with formaldehyde, succinic anhydride or O-methylisourea. 4. Bovine serum albumin modified by a 1.5-fold (BSA-Q) and a fivefold (BSA-Q2) excess of chlorogenoquinone were separated by chromatography on DEAE-Sephadex A-50, and some of their properties observed. 5. Reaction of BSA-Q2 with fluorodinitrobenzene suggests that the terminal alpha-amino group, as well as lysine in-amino groups, are combined with chlorogenoquinone.

Albumins↗

Ilex aquifolium: protection against enzymatic and non-enzymatic lipid peroxidation.

The ethanolic extract of Ilex aquifolium L. (Aquifoliaceae) concentration-dependently inhibited leukotriene B4 biosynthesis in isolated bovine PMNL with an IC50 value of about 60 micrograms/ml, whereas the effect on epidermal 12(S)-HETE biosynthesis was much less pronounced. The extract also inhibited the non-enzymatic, peroxyl radical-stimulated lipid peroxidation in model membranes and was further a scavenger of the iron-dependent generation of hydroxyl radicals from hydrogen peroxide as determined by protection against deoxyribose degradation. While inhibition of leukotriene biosynthesis was not mediated by its known phenolic constituents such as hyperoside, rutoside, and chlorogenic acid, these compounds were responsible for the inhibitory effects of I. aquifolium against non-enzymatic lipid peroxidation and deoxyribose degradation.

12-Hydroxy-5,8,10,14-eicosatetraenoic Acid↗

[Botanical survey and quality evaluation of Chinese drug shiwei (folium Pyrrosiae)].

This paper deals with a botanical survey and identification of the Chinese drug Shiwei (Folium Pyrrosiae) on the basis of three most widely used species included in the 1985 edition of Chinese Pharmacopoeia, six species used in some districts of China, and two adulterant species. Three active constituents in seven species of Folium Pyrrosiae (mangiferin, isomangiferin and chlorogenic acid) have been determined.

Antiviral Agents↗

The cardiovascular effects of caffeine in various forms.

We have investigated the influence of various procedures which alter the solubility of caffeine on its physiological effects. Pretreatment of caffeine prior to injection by a) addition of sodium salicylate or sodium benzoate, b) increase in temperature or c) preliminary dissolution in hydrochloric acid, did not change the cardiovascular effects when injected i.v. at equivalent doses in urethane-anaesthetized rats. Addition of chlorogenic acid, a molecule found in coffee and other plants and reported to modify, by complexation, the physiological effects of caffeine, had no significant effect on the depressor responses to caffeine but did diminish caffeine-induced tachycardia at high doses of caffeine (10 and 30 mg/kg i.v.).

Animals↗

Sunflower seed protein concentrates and isolates obtention from ethanol oil extraction meals--(technical note).

The objective of this work was to study and identify the necessary processing steps for obtaining good quality sunflower seed protein concentrate and isolate when the oil is extracted with ethanol. This work is part of a research project on using ethanol as renewable solvent for sunflower seed oil recovery and possible further processing of the meal. Both 99 degrees GL and 90 degrees GL ethanol were employed in the extractions to produce the concentrate. Isolates were obtained by treating the concentrate with NaOH and HCl solutions and final rinsing with acidified water. Both products were light in color and almost free from chlorogenic acid.

Chlorogenic Acid↗

Hydroxycinnamic acids do not prevent aortic atherosclerosis in hypercholesterolemic golden Syrian hamsters.

The protective effect of hydroxycinnamic acids, i.e. caffeic acid (CA) and sinapic acid (SA) present in wine, and chlorogenic acid (CHA) present in apple, compared to a red wine phenolic extract (RWPE) was investigated in hamsters fed an atherogenic diet for 12 weeks. Five groups of 8 hamsters fed such a diet received by force-feeding RWPE, CA or SA in water, mimicking a moderate consumption of alcohol-free red wine. Controls received water and CHA force-feeding was extrapolated from apple consumption. Plasma cholesterol concentration was lower in group that received RWPE (-22%) and hydroxycinnamic acids had no effect. Plasma apolipoprotein Apo-A1 concentration was not affected; consumption of RWPE only decreased Apo-B concentration (-46%). Liver superoxide dismutase activity was 33% lower and glutathione peroxidase activity was 67% greater in the group receiving RWPE compared to controls; there was no effect when CA, SA or CHA were given. All the phenolic compounds significantly increased plasma antioxidant capacity (about 28% on average) compared with controls. Aortic fatty streak area was significantly reduced in the group receiving RWPE (-30%) in comparison with controls and hydroxycinnamic acids. Our findings demonstrate that chronic ingestion of the nonalcoholic components of red wine, mainly polyphenols, prevent the development of atherosclerosis in hamster and that wine hydroxycinnamic acids are not the phenolic compounds involved in such a beneficial effect.

Animals↗

Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family.

Ten species belonging to the family Lamiaceae and representing the most popular medicinal plants used in Polish phytotherapy were examined for the content of free phenolic acids (PhAs). Two depsides, rosmarinic and chlorogenic acids, as well as eight simple PhAs, protocatechuic, gentisic, p-hydroxybenzoic, caffeic, vanillic, syringic, p-coumaric and ferulic acids, in different qualitative and quantitative proportions depending on the plant examined were determined by the rapid, selective and accurate method combining solid-phase extraction and high-performance liquid chromatography.

Chromatography, High Pressure Liquid↗

Analysis of phenolic acids in barley by high-performance liquid chromatography.

Phenolic acids from 30 barley varieties (combination of hulled/hulless/two-row/six-row/regular/waxy) were investigated by HPLC following four different sample treatments: (a) simple hot water extraction, (b) extraction after acid hydrolysis, (c) acid plus alpha-amylase hydrolysis, and (d) acid plus alpha-amylase plus cellulase hydrolysis treatments. The benzoic acid (p-hydroxybenzoic, vanillic, and protocatechuic acids) and cinnamic acid derivatives (coumaric, caffeic, ferulic, and chlorogenic acids) were identified, and some of the phenolic acids were quantified after each above-mentioned treatment. The data indicated that a combination of sequential acid, alpha-amylase, and cellulase hydrolysis treatments might be applicable for release of more phenolic acids from barley.

Cellulase↗

Cytotoxic constituents of roots of Chaerophyllum hirsutum.

Two new lignan derivatives (1 and 2), along with the known scopoletin (3), methyl caffeate (4), falcarindiol (5), 3,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic methyl ester, chlorogenic acid, p-hydroxyphenylethyl-trans-ferulate, and vanillin, were isolated from extracts of the roots of Chaerophyllum hirsutum. Structure elucidation of the new compounds was carried out by 1D and 2D NMR experiments and by HRMS analysis. Several of the isolated compounds were tested for their cytotoxic activity against the HL-60, HT-1080, LoVo, and LoVo/Doxo cell lines.

Antineoplastic Agents, Phytogenic↗

Effects of some naturally occurring iron ion chelators on in vitro superoxide radical formation.

The effects of some naturally occurring iron ion chelators and their derivatives on the electron transfer from ferrous ions to oxygen molecules were examined by measuring oxygen consumption rates. Of the compounds examined, quinolinic acid, fusaric acid, and 2-pyridinecarboxylic acid repressed the oxygen consumption, whereas chlorogenic acid, caffeic acid, gallic acid, catechol, L-beta-(3,4-dihydroxyphenyl)alanine, and xanthurenic acid accelerated it. Theoretical calculations showed that the energies of the highest occupied molecular orbitals (HOMOs) of [Fe(II)(ligand)3]- complexes were relatively high when the ligands were caffeic acid and its derivatives such as catechol, gallic acid, and L-beta-(3,4-dihydroxyphenyl)alanine. On the other hand, the energies of the HOMOs of [Fe(II)(ligand)3]- complexes were relatively low when the ligands were quinolinic acid and its derivatives such as 2-pyridinecarboxylic acid and fusaric acid. The energies of the HOMOs appear to be closely related with acceleration or repression of the oxygen consumption; that is to say, when the energy of the HOMO is high, the oxygen consumption is accelerated, and vice versa.

Antioxidants↗

Down-regulation of antioxidative capacity in a transgenic tobacco which fails to develop acquired resistance to necrotization caused by TMV.

Antioxidant status was assayed in leaves of two local lesion hosts of tobacco mosaic virus (TMV), namely in wild-type Xanthi-nc tobacco and in NahG transgenic tobacco, the latter of which is not able to accumulate salicylic acid (SA) and therefore is unable to develop systemic acquired resistance (SAR). Activities of several enzymes related to antioxidative defense, and the levels of glutathione, chlorogenic acid and rutin were studied. The majority of antioxidant enzymes were less active in uninfected NahG tobacco than in Xanthi-nc. Furthermore, important enzymatic and non-enzymatic antioxidants were down-regulated in TMV-infected NahG plants, as compared to Xanthi-nc. Correspondingly, SA pretreatment primed the leaves for stronger induction of antioxidants in infected Xanthi-nc, but not in NahG tobaccos. The antioxidant status of NahG tobacco even decreased after an attempted induction of SAR, while the antioxidative level increased in Xanthi-nc leaves in which the SAR was successfully induced. After infection, a greater accumulation of superoxide and H2O2, and a more intensive necrotization was positively correlated with the reduced capability of NahG leaf tissue to detoxify reactive oxygen species.

Antioxidants↗

Antioxidant activity of polyphenols from Hypericum triquetrifolium Turra.

From the aerial parts of Hypericum triquetrifolium Turra (Guttiferae) 3-8"-biapigenin, quercetin, rutin and chlorogenic acid were isolated. Their structures were elucidated by spectral techniques. Furthermore, the phenolic compounds were tested for antioxidant activity, using an in vitro method based on sodium arachidonoate, bleomycin and thiobarbituric acid with alpha-tocopherol as the reference solution.

Antioxidants↗

Effect of photoperiod and end-of-day light quality on alkaloids and phenolic compounds of tobacco.

Tobacco plants (Nicotiana tabacum L.) were grown on long or short photoperiods followed by 5 minutes of red or far red radiation each day. Plants that received 16-hour photoperiods had a significantly higher concentration of total alkaloids and total phenolics than those that received 8-hour photoperiods. Significantly higher total alkaloid content was found in plants that received red rather than far red radiation last each day. Within each photoperiod, plants that received far red had higher concentrations of soluble phenols, particularly of chlorogenic acid. The interactions among these variables upon alkaloid and phenolic contents are discussed.

Alkaloids↗

[Studies on chemical constituents from Polygonum macrophyllum].

OBJECTIVE: To study the chemical structures from Polygonum macrophyllum D. Don. METHODS: To isolate the constituents by reverse phase chromatography and characterize their structures by the analysis of chemical property and spectral data. RESULT: Six compounds were isolated from the 70% acetone extract from the complete herb of P. macrophyllum. Their structures were elucidated as (-)-epicatechin-5-O-beta-D-glucopyranoside (I), (+)-catechin-7-O-beta-D-glucopyranoside (II), 1-(3-O-beta-D-glucopyranosyl 4,5-dihydroxy-phenyl)-ethanone (III) (-)-epicatechin (IV), chlorogenic acid (V) and gallic acid (VI). CONCLUSION: Compounds I-VI were isolated from the plant for the first time.

Catechin↗

Extraction and identification of antioxidants in the roots of yacon (Smallanthus sonchifolius).

Yacon, Smallanthus sonchifolius (Poepp. & Endl.) H. Robinson, Asteraceae, an important economic species grown for its juicy tuberous root, is potentially beneficial in the diet to diabetics. The antioxidative activity of yacon root was studied by 1, 1-diphenyl-2-picrylhydrazyl (DPPH) assay. Antioxidants were extracted by methanol and isolated and purified by gel permeation chromatography and preparative reverse-phase HPLC. Two of the major antioxidants were identified as chlorogenic acid and tryptophan by NMR and mass spectrometry.

Antioxidants↗

Phenolic compounds and related enzymes are not rate-limiting in browning development of fresh-cut potatoes.

The effect of minimal processing on polyphenol oxidase (PPO), peroxidase (POD), phenylalanine ammonia-lyase (PAL), and phenolic compounds was studied in five potato cultivars (Agria, Cara, Liseta, Monalisa, and Spunta). Minimal processing caused an overall increase in PPO, POD, and PAL activities. The isoform pattern of PPO was the same for all of the cultivars before and after processing. No latent PPO was detected. The isoperoxidase pattern was approximately the same among cultivars. An increase in POD activity was related to the specific induction of an acidic isoperoxidase. PAL showed an induction pattern characterized by the presence of a maximum peak of activity after 4 days of processing for all of the cultivars. The sequence of browning susceptibility of potato cultivars was as follows: Monalisa > Spunta > Liseta > Cara > Agria. Browning development was only partially correlated to PAL activity (only during the first 4 days after wounding). However, this correlation could not explain the above sequence of browning susceptibility. Minimal processing caused an increase of chlorogenic acid, whereas tyrosine content remained unchanged. In summary, no significant correlation was found between either rate or degree of browning and any other biochemical and physiological attribute investigated (PPO, POD, hydrogen peroxide, ascorbic acid content, and initial phenolics content as well as total and individual phenolics accumulation).

Catechol Oxidase↗

Quantitative precursor studies on di- and trihydroxybenzene formation during coffee roasting using "in bean" model experiments and stable isotope dilution analysis.

The objective of this study was to investigate the potential of various raw bean components as precursors of pyrogallol (1), hydroxyhydroquinone (2), catechol (3), 4-ethylcatechol (4), 4-methylcatechol (5), and 3-methylcatechol (6) under quasi "natural" roasting conditions by using the recently developed "in bean" model roast experiments. Freeze-dried, fully extracted bean shells were loaded with aqueous solutions of either single coffee compounds or fractions isolated from the raw bean solubles. After freeze-drying, these reconstituted beans were roasted, aqueous coffee brews were prepared, and the target phenols were quantified by means of a stable isotope dilution assay with LC-MS/MS detection. On the basis of the quantitative data, it can be concluded that upon coffee bean roasting, catechol (3) is primarily formed by degradation of caffeoylquinic acids from both the caffeic acid and the quinic acid moiety of the molecule, as well as from Maillard-type reactions from carbohydrates and amino acids. In contrast, pyrogallol (1) and hydroxyhydroquinone (2) are efficiently generated from carbohydrates and amino acids and, in addition, from free or chlorogenic acid bound quinic acid moieties. 4-Ethylcatechol (4) is exclusively generated upon thermal breakdown of caffeic acid moieties. 3-Methylcatechol (6) is formed primarily from the Maillard reactions and, to a minor extent, also from various phenolic precursors, whereas 4-methylcatechol (5) is produced in trace amounts only from all of the different precursors investigated. On the basis of this precursor study, reaction routes explaining the formation of the target phenols are proposed.

Catechols↗