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At least 433 records · Page 24Linked to original sources
PubMed2003

Herbal remedies of Solidago--correlation of phytochemical characteristics and antioxidative properties.

In this study the correlation of phytochemical characteristics and antioxidative properties of classical herbal tea extracts-Infusum solidaginis, Decoctum solidaginis, Maceratum solidaginis-and tinctures prepared by various concentration of ethanol (40, 70, 96% v/v) have been examined for the release of flavonoids and their antioxidant activity. Quantitative and composition determination of flavonoids were carried out by spectrophotometry, high-performance liquid chromatography and capillary electrophoresis, respectively. Hydrogen-donating ability and reducing power properties were used to define in vitro radical scavenging activity of Solidago extracts, but integral antioxidative capacity was determined by luminometry (Photochem), calculating the ascorbic acid equivalents. Chlorogenic acid, quercetin-3-O-beta-D-rutinoside, quercetin-3-O-beta-D-galactoside, quercetin-3-O-beta-D-glucoside, quercetin-3-O-beta-D-rhamnoside, kaempferol-3-O-alpha-L-rhamnoside and quercetin were confirmed by retention times and UV spectra. Based on the dissolution rate, variance of flavonoid release and ascorbic acid equivalents it was concluded, that Tinctura solidaginis (70% v/v ethanol) and Infusum solidaginis are the most appropriate preparations.

Antioxidants↗
PubMed2003

Simultaneous determination of hydroxycinnamates and catechins in human urine samples by column switching liquid chromatography coupled to atmospheric pressure chemical ionization mass spectrometry.

A quantitative liquid chromatography mass spectrometry (LC-MS) methodology with online sample clean up by column switching is described for the simultaneous determination of the hydroxycinnamates, caffeic acid and chlorogenic acid, and of the catechins, epicatechin and catechin in human urine samples. Enzymatically treated urine samples were directly injected onto the LC-MS system, where sample clean up was performed by a reversed-phase Zorbax 300SB C(3) column and selective elution of the target compounds onto a Zorbax SB C(18) column resulted in final separation prior to detection by atmospheric pressure chemical ionization (APCI) MS using single ion monitoring (SIM) in negative mode. Linear calibration graphs were achieved in the dynamic range of 10-1000 ng/ml urine. The inter- and intraassay coefficients of variation (C.V.%) for the analysis of the four compounds in quality control urine samples were between 7.8 and 10.9, n=17 (reproducibility), and the repeatability of the assay was between 2.5 and 5.0% (n=12). Analyses of urine samples from a human dietary intervention study with intake of 600 g of fruits and vegetables were demonstrated. To our knowledge, this is the first method described that allows simultaneous determination of both hydroxycinnamates and catechins in biological samples.

Atmospheric Pressure↗
PubMed1999

Phenolic composition of kiwifruit juice.

Phenolic compounds in kiwifruit pulp were separated and characterized by reversed-phase HPLC, and the effect of juice processing on the phenolic composition was studied. Fractionation of phenolic compounds was achieved through selective elution from C-18 cartridges prior to preconcentration and subsequent separation by HPLC. Strongly acidic compounds were identified as derivatives of coumaric and caffeic acids, including chlorogenic acid, protocatechuic acid, and a derivative of 3,4-dihydroxybenzoic acid. The weakly acidic fraction contained epicatechin, catechin, and procyanidins (B3, B2, or B4 and oligomers). Flavonols were present as the glycosides of quercetin (glucoside, rhamnoside, and rutinoside) and kaempferol (rhamnoside and rutinoside). Phenolic compounds were present, at levels of <1-7 mg/L, in clarified juice. The concentration of phenolics was highest after high-temperature short-time treatment (HTST) of juice. Hydrolysis of hydroxycinnamic acids occurred after enzyme addition and HTST treatment. The flavonol glycoside composition is the best identifier of kiwifruit juice.

Beverages↗
PubMed2004

Inhibiting activities of the secondary metabolites of Phlomis brunneogaleata against parasitic protozoa and plasmodial enoyl-ACP Reductase, a crucial enzyme in fatty acid biosynthesis.

Anti-plasmodial activity-guided fractionation of Phlomis brunneogaleata (Lamiaceae) led to the isolation of two new metabolites, the iridoid glycoside, brunneogaleatoside and a new pyrrolidinium derivative (2 S,4 R)-2-carboxy-4-( E)- p-coumaroyloxy-1,1-dimethylpyrrolidinium inner salt [(2 S,4 R)-1,1-dimethyl-4-( E)- p-coumaroyloxyproline inner salt]. Moreover, a known iridoid glycoside, ipolamiide, six known phenylethanoid glycosides, verbascoside, isoverbascoside, forsythoside B, echinacoside, glucopyranosyl-(1-->G (i)-6)-martynoside and integrifolioside B, two flavone glycosides, luteolin 7- O-beta- D-glucopyranoside ( 10) and chrysoeriol 7- O-beta- D-glucopyranoside ( 11), a lignan glycoside liriodendrin, an acetophenone glycoside 4-hydroxyacetophenone 4- O-(6'- O-beta- D-apiofuranosyl)-beta- D-glucopyranoside and three caffeic acid esters, chlorogenic acid, 3-O-caffeoylquinic acid methyl ester and 5- O-caffeoylshikimic acid were isolated. The structures of the pure compounds were elucidated by means of spectroscopic methods (UV, IR, MS, 1D and 2D NMR, [alpha] (D)) and X-ray crystallography. Compounds 10 and 11 were determined to be the major anti-malarial principles of the crude extract (IC (50) values of 2.4 and 5.9 micrograms/mL, respectively). They also exhibited significant leishmanicidal activity (IC (50) = 1.1 and 4.1 micrograms/mL, respectively). The inhibitory potential of the pure metabolites against plasmodial enoyl-ACP reductase (FabI), which is the key regulator of type II fatty acid synthases (FAS-II) in P. falciparum, was also assessed. Compound 10 showed promising FabI inhibiting effect (IC (50) = 10 micrograms/mL) and appears to be the first anti-malarial natural product targeting FabI of P. falciparum.

Animals↗
PubMed2005

Antioxidant and free radical scavenging activities of some leafy vegetables.

Some leafy vegetables were studied for their nutritional composition, antioxidant and free radical scavenging activities. The aerial parts of Coriandrum sativum, Spinacia oleracea, Trigonella corniculata and Trigonella foenum-graecum showed lower inhibitory concentration values (4.1-7.9 mg/ml), efficiency concentration values (178-321 mg/mg DPPH) and higher values of anti-radical power (0.31-0.51) as compared with their seeds. Thermal treatment reduced the total phenolic contents, antioxidant and free radical scavenging activities. The leaves of C. sativum were found with good amounts of caffeic acid, ferulic acid, gallic acid and chlorogenic acid.

Antioxidants↗
PubMed2001

Iridoid and phenylethanoid glycosides from Phlomis longifolia var. longifolia.

From the aerial parts of Phlomis longifolia var. longifolia four iridoid glucosides, shanzhiside methyl ester (1), 5-deoxypulchelloside I (2), lamalbide (3), phlomiol (4) and three phenylethanoid glycosides, verbascoside (5), forsythoside B (6), leucosceptoside A (7) along with the caffeic acid ester, chlorogenic acid (8) were isolated. The structures of the isolated compounds were established by spectroscopic (UV, IR, 1D- and 2D-NMR, FABMS) and chemical evidence. The structure elucidation of the iridoid compounds 2 and 3 are discussed in detail.

Chromatography, Liquid↗
PubMed1994

Responses of lipid membranes of taste sensor to astringent and pungent substances.

Astringent substances and pungent substances were studied using a multichannel taste sensor with lipid membranes. The electric-potential pattern constructed of eight outputs from the membranes has information of taste quality and intensity. Pungent substances, such as capsaicin, piperine and allyl isothiocyanate, had no effect on the membrane potentials of the lipid membranes. On the other hand, astringent substances such as tannic acid, catechin, gallic acid and chlorogenic acid changed the potentials remarkably. A principal component analysis of the patterns in electric potential changes caused by the taste substances revealed the astringency is located between bitterness and sourness.

Astringents↗
PubMed1996

Isolation and identification of compounds from Brazilian propolis which enhance macrophage spreading and mobility.

Brazilian propolis is known to induce the activation of murine effector cells. We isolated and identified six compounds from a water-soluble extract of Brazilian propolis, all of which have enhancing effects on the spreading and mobility of murine macrophages. These compounds were identified as caffeoylquinic acid-derivatives, namely, 5-caffeoylquinic acid (1), chlorogenic acid (2), 4-caffeoylquinic acid (3), 4,5-dicaffeoylquinic acid (4), 3,5-dicaffeoylquinic acid (5) and 3,4-dicaffeoylquinic acid (6).

Animals↗
PubMed2005

Enzymatic production of caffeic acid by koji from plant resources containing caffeoylquinic acid derivatives.

The effect of a koji (Aspergillus awamori mut.) extract on the caffeoylquinic acid derivatives purified from sweetpotato (Ipomoea batatas L.) leaves was examined to develop the mass production of caffeic acid. A koji extract hydrolyzed the caffeoylquinic acid derivatives, chlorogenic acid, 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid and 3,4,5-tri-O-caffeoylquinic acid, to caffeic acid. Furthermore, the koji extract also converted the major polyphenolic components from sweetpotato, burdock (Arctium lappa L.), and mugwort (Artemisia indica var. maximowiczii) leaves to caffeic acid. These results suggest that the production of caffeic acid from plant resources containing caffeoylquinic acid derivatives is possible.

Aspergillus↗
PubMed2002

[Studies on the phenylpropanoids from Eucommia ulmoides].

OBJECTIVE: To study the chemical constituents from the leaves of Eucommia ulmoides. METHOD: The constituents were isolated by chromatography method and the structures were identified on the basis of spectral analysis. RESULT: Six compounds, ursolic acid(1), beta-sitosterol(2), p-coumaric(3), caffeic acid ethyl ester(4), chlorogenic acid(5) and syringin(6) were obtained. CONCLUSION: Compound 3, 4, 5 were obtained from the plant for the first time.

Caffeic Acids↗
PubMed2003

[Isolation and elucidation of chemical constituents with antiviral action from yinqiaosan on influenza virus].

OBJECTIVE: To study the chemical constituents with antiviral action from Yinqiaosan on influenza virus. METHOD: Constituents were isolated by different kinds of column chromatography and their structures were elucidated with chemical and spectral methods. RESULT: Eleven chemical constituents were isolated and elucidated as arctiin, phillyrin, forsythiaside, liquiritigenin, liquiritin, genistein, formononetin, daidzein, glycitrin, 3,3',4-tri-omethlellagic acid and chlorogenic acid. CONCLUSION: Genistein, daidzein, glycitrin and 3,3',4-tri-omethlellagic acid were isolated from Yinqiaosan for the first time.

Antiviral Agents↗
PubMed1981

Reactions between phosphorylated thiamines and tannic acid as followed by difference spectroscopy.

Caffeic acid, catechin, chlorogenic acid, hydroquinone (also benzoquinone) and tannic acid were used to react with thiamine and the ultraviolet-visible difference spectra were recorded. The time-course of the thiamine-polyphenol interactions was studied by following the difference absorbance change with time. The rate of reaction as determined by difference spectroscopy was the same as that found by chemical assay. The spectroscopic method showed that thiamine, thiamine monophosphate and thiamine diphosphate reaction rate with tannic acid followed the order thiamine greater than thiamine monophosphate greater than thiamine diphosphate up to pH 7.4.

Flavonoids↗
PubMedDate not supplied

Structure-activity relationship of caffeic acid analogues on xanthine oxidase inhibition.

Caffeic acid has been reported to have activity on xanthine oxidase inhibition which is related to several diseases, e.g. gout, hepatitis and tumors. Based on this study, the alpha, beta-unsaturated COOH moiety in the molecule of caffeic acid plays a very important role on the xanthine oxidase inhibition because hydrocaffeic acid was inactive and the activities of coniferyl aldehyde and coniferyl alcohol were reduced as compared with ferulic acid. Moreover, chlorogenic acid showed a weaker activity than caffeic acid. On the other hand, the phenolic OH group present in the molecule of caffeic acid makes an important contribution to the activity, e.g. transcinnamic acid in which the absence of the phenolic OH group in the structure reduced its activity as compared with caffeic acid. Ferulic acid, isoferulic acid and 3,4-dimethoxy cinnamic acid also had reduced activity due to the methoxy groups replacing the phenolic OH group in the structures. However, m-coumaric acid displayed the strongest activity (IC50 = 63.31 microM) and induced uncompetitive inhibition with respect to the substrate xanthine (Ki = 21.568 microM). Caffeic acid (IC50 = 74.6 microM) showed the second strongest activity, followed by p-coumaric acid (IC50 = 111.09 microM).

Caffeic Acids↗
PubMedDate not supplied

In vivo effect of dietary factors on the molecular action of aflatoxin B1: role of non-nutrient phenolic compounds on the catalytic activity of liver fractions.

Young adult rats were kept on a synthetic diet containing various food associated phenolic compounds each at 0.5% level. The ability of liver microsomes to catalyze reactions of aflatoxin B1 leading to its activation and DNA adduct formation was measured after an experimental feeding period of 3 weeks. A decrease in both activities was observed with several flavonoids (fisetin, kaempferol, morin, naringin and (+/-)catechin), phenolic acids (caffeic acid and chlorogenic acid), other phenolics (eugenol, vanillin) and synthetic phenolic antioxidants butylated hydroxyanisole and butylated hydroxytoluene. Certain phenolics notably naringin, (+/-) catechin, eugenol, vanillin and butylated hydroxyanisole were also found to induce cytosolic glutathione S-transferase activity that stimulated the formation of specific aflatoxin B1-glutathione conjugate. The results emphasize the role of phenolic compounds in the activation and detoxification processes, and hence in modulating the carcinogenicity of aflatoxin B1.

Aflatoxin B1↗
PubMed1994

The blocking effect of phenolic acid on N-nitrosomorpholine formation in vitro.

Phenolic acids (PAs) are widely found in many daily consumed vegetables and fruits. The inhibitory effects of PAs on N-nitrosomorpholine (NMOR) formation in vitro under simulated gastric juice condition were studied. The results showed that the inhibitory potency of thirteen varieties of PAs differed greatly, which may be related to their chemical structures; the blocking rate (BR) of different kinds of PAs were as follows: caffeic acid, 92.5%; tannic acid, 90.0%; gallic acid, 86.8%; sinapinic acid, 86.2%; ferulic acid, 81.1%; chlorogenic acid, 69.4%; gentisic acid, 69.2%; syringic acid, 62.1%; protocatechuic acid, 56.0%; p-coumaric acid, 52.5%; vanillic acid, 35.4%; moreover, p-hydroxybenzoic acid and m-coumaric acid had the least blocking effect or even slight catalyzing effect. The results also demonstrated that amounts of NMOR formed were negatively correlated with molar ratio of PAs to nitrite and that the optimum pH for inhibition was between 2 and 3.

Carcinogens↗
PubMed2000

Some polyphenols inhibit the formation of pentyl radical and octanoic acid radical in the reaction mixture of linoleic acid hydroperoxide with ferrous ions.

Effects of some polyphenols and their related compounds (chlorogenic acid, caffeic acid, quinic acid, ferulic acid, gallic acid, D-(+)-catechin, D-(-)-catechin, 4-hydroxy-3-methoxybenzoic acid, salicylic acid, L-dopa, dopamine, L-adrenaline, L-noradrenaline, o-dihydroxybenzene, m-dihydroxybenzene, and p-dihydroxybenzene) on the formation of 13-hydroperoxide octadecadienoic (13-HPODE) acid-derived radicals (pentyl radical and octanoic acid radical) were examined. The ESR spin trapping showed that chlorogenic acid, caffeic acid, gallic acid, D-(+)-catechin, D-(-)-catechin, L-dopa, dopamine, L-adrenaline, L-noradrenaline, and o-dihydroxybenzene inhibited the overall formation of 13-HPODE acid-derived radicals in the reaction mixture of 13-HPODE with ferrous ions. The ESR peak heights of alpha-(4-pyridyl-1-oxide)-N-tert-butylnitrone (4-POBN)/13-HPODE-derived radical adducts decreased to 46+/-4% (chlorogenic acid), 54+/-2% (caffeic acid), 49+/-2% (gallic acid), 55+/-1% [D-(+)-catechin], 60+/-3% [D-(-)-catechin], 42+/-1% (L-dopa), 30+/-2% (dopamine), 49+/-2% (L-adrenaline), 24+/-2% (L-noradrenaline), and 54+/-5% (o-dihydroxybenzene) of the control, respectively. The high performance liquid chromatography-electron spin resonance (HPLC-ESR) and high performance liquid chromatography-electron spin resonance-mass spectrometries (HPLC-ESR-MS) showed that caffeic acid inhibited the formation of octanoic acid radical and pentyl radical to 42+/-2% and 52+/-7% of the control, respectively. On the other hand, the polyphenols and their related compounds had few inhibitory effects on the radical formation in the presence of EDTA. Visible absorbance measurement revealed that all the polyphenols exhibiting the inhibitory effect chelate ferrous ions. Above results indicated that the chelation of ferrous ion is essential to the inhibitory effects of the polyphenols.

Chromatography, High Pressure Liquid↗
PubMed2002

Vitamin C equivalent antioxidant capacity (VCEAC) of phenolic phytochemicals.

To express the antioxidant capacity of plant foods in a more familiar and easily understood manner (equivalent to vitamin C mg/100 g), two stable radical species, ABTS(*)(-) and DPPH(*), commonly used for antioxidant activity measurements, were employed independently to evaluate their efficacies using apple polyphenolic extracts and seven polyphenolic standards including synthetic Trolox. Their antioxidant activities were expressed as vitamin C equivalent antioxidant capacity (VCEAC) in mg/100 g apple or mg/100 mL of the reference chemical compounds in 10 and 30 min using the ABTS(*)(-) and DPPH(*) scavenging assays, respectively. The antioxidant capacity of Gala apples and seven phenolic standards, determined by both ABTS(*)(-) and DPPH(*) scavenging assays, showed a dose-response of the first-order. Fresh Gala apples had a VCEAC of 205.4 +/- 5.6 mg/100 g using the ABTS assay, and the relative VCEACs of phenolic standards were as follows: gallic acid > quercetin > epicatechin > catechin > vitamin C > rutin > chlorogenic acid > Trolox. With the DPPH radical assay, the VCEAC of fresh Gala apples was 136.0 +/- 6.6 mg/100 g, and the relative VCEACs of seven phenolic standards were, in decreasing order, as follows: gallic acid > quercetin > epicatechin > catechin > or = vitamin C > Trolox > rutin > chlorogenic acid. Because the ABTS assay can be used in both organic and aqueous solvent systems, employs a specific absorbance at a wavelength remote from the visible region, and requires a short reaction time, it is a more desirable method than the DPPH assay. Therefore, it is recommended that antioxidant capacity be expressed as vitamin C mg/100 g equivalent (VCEAC) using the ABTS assay.

Antioxidants↗
PubMed1991

Inhibitory effect of curcumin and some related dietary compounds on tumor promotion and arachidonic acid metabolism in mouse skin.

Topical application of curcumin, the major yellow pigment in turmeric and curry, has a potent inhibitory effect on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced tumor promotion in mouse skin. The structurally related compounds chlorogenic acid, caffeic acid and ferulic acid are less potent inhibitors. Curcumin is a potent inhibitor of TPA-induced ornithine decarboxylase activity and inflammation in mouse skin whereas chlorogenic acid, caffeic acid and ferulic acid are only weakly active or inactive. Curcumin is a potent inhibitor of arachidonic acid-induced inflammation in vivo in mouse skin, and this compound is also a potent inhibitor of epidermal lipoxygenase and cyclooxygenase activity in vitro. Although chlorogenic acid is only weakly active as an inhibitor of epidermal lipoxygenase activity and TPA-induced ear inflammation, it is more active than caffeic acid and ferulic acid. The inhibitory effects of curcumin, chlorogenic acid, caffeic acid and ferulic acid on TPA-induced tumor promotion in mouse skin parallel their inhibitory effects on TPA-induced epidermal inflammation and epidermal lipoxygenase and cyclooxygenase activities. Examination of the structural features of curcumin required for its biological activity indicate that free hydroxyl groups on the benzene rings are not required for inhibition of TPA-induced ornithine decarboxylase activity and inflammation in mouse skin.

Arachidonic Acid↗