chlorogenic-acid and 1-1-diphenyl-2-picrylhydrazyl

Twelve chlorogenic acid derivatives and two flavones were isolated from Moquiniastrum floribundum (Asteraceae, other name: Gochnatia floribunda). Compounds were evaluated in relation to their cytotoxicity and antiradical properties. Cytotoxicity was not observed for compounds, however, chlorogenic acid derivatives showed antiradical activity and were more active than the Trolox standard. Quinic acid esterified with caffeoyl group at C-4 position showed higher antiradical activity compared to acylation at C-3 or C-5 positions. Additional caffeoyl groups esterified in quinic acid increase the antiradical activity observed for 4-caffeoylquinic acid. Excepted to 3,4-dicaffeoylquinic acid methyl ester, methyl ester derivatives show higher capacity of trapping radicals than their respective acids. Consequently, the presence of caffeoyl group at C-4 position of quinic acid is suggested as fundamental to obtain the highest antiradical activity.

Topics: Antineoplastic Agents, Phytogenic; Antioxidants; Asteraceae; Biphenyl Compounds; Cell Proliferation; Dose-Response Relationship, Drug; HCT116 Cells; Humans; Molecular Structure; Picrates; Quinic Acid; Structure-Activity Relationship

To investigate the bioactive constituents of the inflorescences of Scabiosa comosa and S. tschilliensis, which are used traditionally for liver diseases, we tested the antioxidant activity using 2,2'-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS), ferric reducing antioxidant potential (FRAP), and DPPH-ultra high performance liquid chromatography-mass spectrometer (UPLC-MS) assay. In addition, cell-based anti-HCV activity of the major compounds were evaluated. The plant extracts showed strong antioxidant activity. For the first time, 3,4-dicaffeoylquinic acid (DCQA), 3,5-DCQA and 4,5-DCQA were identified from genus Scabiosa. A UPLC-MS method in multiple reaction monitoring (MRM) mode was established to quantify 18 constituents in the inflorescences of Scabiosa. The 3,5-DCQA, chlorogenic acid and some glycosides of luteolin or apigenin were found to be the most abundant constituents. Chlorogenic acid and 3,5-DCQA showed excellent radical scavenging activity and demonstrated anti-HCV activity. These findings provided scientific evidences for the clinic use of this herbal medicine for liver diseases.

Topics: Antioxidants; Antiviral Agents; Biphenyl Compounds; Chlorogenic Acid; Dipsacaceae; Free Radical Scavengers; Hepacivirus; Humans; Luteolin; Picrates; Plant Extracts; Quinic Acid; Spectrometry, Fluorescence

A simple and efficient method based on high-performance thin-layer chromatography coupled with 2,2-diphenyl-1-picrylhydrazyl (DPPH) bioautography (HPTLC-DPPH) was established for the screening and comparison of antioxidants in different parts of Coreopsis tinctoria herbal tea from different origins and other related herbal tea materials, which used Chrysanthemum morifolium cv. "Gongju" and "Hangju" in this study. Scanning densitometry after DPPH derivatization was applied for the determination of antioxidant capacities of isolated compounds in each sample. It is considered that ethanol extracts of C. tinctoria had stronger antioxidant activity and more characteristic bands than those of 2 compared samples, C. morifolium cv. "Gongju" and "Hangju." Chemometric analysis results showed that the combination of hierarchical clustering analysis and principal component analysis based on determined antioxidant capacities could be used for the discrimination of different parts of C. tinctoria and C. morifolium. Results showed that 7 compounds made up the major contributions of antioxidant activity in C. tinctoria, including okanin, isookanin, marein, flavanomarein, 5,7,3',5'-tetrahydroxyflavanone-7-O-glucoside, 3,5-dicaffeoylquinic acid, and chlorogenic acid. Therefore, 7 compounds were identified as major antioxidant biomarkers for quality control of C. tinctoria. Results demonstrated that the established method could be applied for the identification of C. tinctoria, and were beneficial for the bioactivity-based quality control of C. tinctoria.

Topics: Antioxidants; Biphenyl Compounds; Chalcones; Chlorogenic Acid; Chromatography, Thin Layer; Chrysanthemum; Coreopsis; Densitometry; Flavanones; Picrates; Plant Extracts; Quality Control; Quinic Acid; Teas, Herbal

The aerial parts of several Haplopappus species (Asteraceae), known under the common name "baylahuen", are used as herbal teas in Chile and Argentina. In Chile, "baylahuen" comprises H. multifolius, H. taeda, H. baylahuen and H. rigidus. Little is known about the chemical identity of the infusion constituents in spite of widespread consumption. The aim of the present work was the characterization of phenolics occurring in the infusions and methanol extracts of "baylahuen" by HPLC-DAD-ESI-MS. A simple HPLC-DAD-ESI-MS method was developed for the fast identification and differentiation of Haplopappus spp. used as a tea source, based on the phenolics from the tea and methanol extracts. Some 27 phenolics were tentatively identified in the infusions and methanol extract, including 10 caffeoyl quinic and feruloyl quinic acid derivatives and 17 flavonoids. The HPLC patterns of the Haplopappus tea and methanol extract allow a clear differentiation at the species level. The occurrence of hydroxycinnamic acid derivatives and flavonoids can explain the reputed nutraceutical and health beneficial properties of this herbal tea.

Topics: Biphenyl Compounds; Chile; Chromatography, High Pressure Liquid; Flavonoids; Haplopappus; Phenols; Picrates; Plant Extracts; Quinic Acid; Spectrometry, Mass, Electrospray Ionization; Tea

From an extract of the aerial parts of Dracocephalum ruyschiana, five new flavone tetraglycosides, five new benzyl alcohol glycosides, and 19 known compounds were isolated. The tetraglycosides contain a 7-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranosyl moiety. The benzyl alcohol glycosides had acyl groups on their glycosyl or aglycone moieties. The compounds were tested for antioxidant activity using DPPH. Although the new compounds were not active, phenylpropanoylquinic acid derivatives were revealed as radical scavengers in D. ruyschiana.

Topics: Antioxidants; Benzyl Alcohol; Biphenyl Compounds; Flavones; Free Radical Scavengers; Glycosides; Lamiaceae; Molecular Structure; Mongolia; Picrates; Plants, Medicinal

Baccharis plants have been used since ancient times in American traditional medicine. Baccharis chilco is a perennial shrub of temperate regions of South America that grows well in rainfall forests of Colombia. Neither chemical composition nor biological studies of this plant have ever been reported. Two caffeoylquinic acid (CQA) derivatives, 5-O-[(E)-caffeoyl]quinic acid (1) and 3,5-di-O-[(E)-caffeoyl]quinic acid (3), and rosmarinic acid (2) have been isolated from B. chilco growing wild in Colombia, using the on-line HPLC-DAD-DPPH radical-scavenging detection technique as guidance. In the course of the purification work, L-chiro-inositol (4) was also isolated. Structures of the four isolated compounds were determined by spectroscopic methods. Antioxidants 2 and 3 exhibited high antiradical activities evaluated by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(.)) assay, although somewhat lower than that of the reference compound ascorbic acid. The on-line HPLC-DAD-DPPH technique allowed a rapid pinpointing of antioxidants in the studied EtOH extract, and the facile guided isolation of the target molecules.

Topics: Baccharis; Biphenyl Compounds; Chromatography, High Pressure Liquid; Cinnamates; Depsides; Free Radical Scavengers; Free Radicals; Inositol; Picrates; Plant Extracts; Quinic Acid; Rosmarinic Acid

Chromatographic separation of a crude extract obtained from the aerial parts of the Mongolian medicinal plant Scorzonera divaricata yielded the two new quinic acid derivatives feruloylpodospermic acids A and B. Both compounds feature a feruloyl group and two dihydrocaffeoyl substituents. For feruloylpodospermic acid A, the dihydrocaffeic acid substituents were found esterified at positions 1 and 5 of the quinic acid moiety, while the feruloyl group was attached at position 3. For feruloylpodospermic acid B, the substituents were linked at positions 1, 3, and 4. The aerial parts of S. pseudodivaricata that are likewise used in Mongolian traditional medicine yielded two further new natural products, for which the names scorzoneric acid and scorzonerin are proposed. Scorzoneric acid is an unusual phenolic compound featuring a central tetrasubstituted phenyl ring to which a glucose unit is bound, which in turn is substituted by an esterified acyl side chain. Further substituents of the central phenyl ring system include a butan-2-one group, which is linked to a second para-substituted phenyl ring system. Scorzonerin is a matricarin-based sesquiterpene lactone that carries an esterified dihydrocoumaric acid moiety, which in turn is glycosidically bound to glucose. The structures of all new compounds were unambiguously established from NMR (1H, 13C, COSY, HMBC) spectroscopic and mass spectrometric data. The new quinic acid derivatives feruloylpodospermic acids A and B exhibited strong antioxidative activity when analyzed in the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay.

Topics: Animals; Antineoplastic Agents; Antioxidants; Biological Products; Biphenyl Compounds; Drug Screening Assays, Antitumor; Mice; Molecular Structure; Mongolia; Picrates; Plants, Medicinal; Quinic Acid; Scorzonera

The methanol extract from Dipsacus asper Wall (Dipsacaceae) was found to show antioxidant activity against free radical and Cu(2+)-mediated LDL oxidation. In further study, to identify active constituents from the plant, six caffeoyl quinic acid derivatives: 3,4-di-O-caffeoylquinic acid (1), methyl 3,4-di-O-caffeoyl quinate (2), 3,5-di-O-caffeoylquinic acid (3), methyl 3,5-di-O-caffeoyl quinate (4), 4,5-di-O-caffeoylquinic acid (5) and methyl 4,5-di-O-caffeoyl quinate (6) were isolated. Their structures were identified by spectroscopic methods including 2D-NMR. The isolated compounds, 1-6, were found to be potent scavengers of the free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), and are more potent than butylated hydroxyl toluene (BHT) used as a positive control. The compounds 1-6 also inhibited Cu(2+)-mediated low-density lipoprotein (LDL) oxidation. They increased the lag time of conjugated dienes formation and inhibited the generation of thiobarbituric acid reactive substances (TBARS) in a dose-dependent manner. These results suggested that Dipsacus asper due to its antioxidant constituents, 1-6, may have a role to play in preventing the development and progression of atherosclerotic disease.

Topics: alpha-Tocopherol; Antioxidants; Biphenyl Compounds; Butylated Hydroxytoluene; Caffeic Acids; Chlorogenic Acid; Copper; Dipsacaceae; Dose-Response Relationship, Drug; Free Radical Scavengers; Gallic Acid; Humans; Hydrazines; Lipid Peroxidation; Lipoproteins, LDL; Malondialdehyde; Methanol; Molecular Structure; Monosaccharides; Picrates; Plant Extracts; Plant Roots; Plants, Medicinal; Quinic Acid; Thiobarbituric Acid Reactive Substances

Two new dicaffeoylquinic acids, 3,5-dicaffeoyl- epi-quinic acid (1) and 1,3-dicaffeoyl- epi-quinic acid (2), were isolated from Chrysanthemum morifolium Ramar together with six known dicaffeoylquinic acid derivatives and three flavonoids. The structures of the new compounds were elucidated using of spectroscopic methods. These compounds were assessed for antioxidant activities in the DPPH radical and superoxide anion radical scavenging systems. Most of the isolates showed strong antioxidant activities in these assay systems. Two new compounds showed potent superoxide anion radical scavenging activity (IC50 = 2.9 +/- 0.1 for 1 and 2.6 +/- 0.4 microg/mL for 2, respectively) in the xanthine/xanthine oxidase system as compared to quercetin and also showed potent DPPH radical scavenging activity (IC50 = 5.6 +/- 0.1 for 1 and 5.8 +/- 0.2 microg/mL for 2, respectively).

Topics: Antioxidants; Biphenyl Compounds; Chrysanthemum; Flowers; Free Radical Scavengers; Humans; Inhibitory Concentration 50; Phytotherapy; Picrates; Plant Extracts; Quinic Acid; Superoxides

Activity-guided fractionation of a methanol extract from the fruit of Manilkara zapota cv. Tikal resulted in the isolation of two new antioxidants, methyl 4-O-galloylchlorogenate (1) and 4-O-galloylchlorogenic acid (2), along with eight known polyphenolic antioxidants, namely, methyl chlorogenate (3), dihydromyricetin (4), quercitrin (5), myricitrin (6), (+)-catechin (7), (-)-epicatechin (8), (+)-gallocatechin (9), and gallic acid (10). Of the 10 polyphenols, 1 showed the highest antioxidant activity (IC(50) = 12.9 microM) in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free-radical assay and displayed cytotoxicity in the HCT-116 and SW-480 human colon cancer cell lines with IC(50) values of 190 and 160 microM, respectively. Compound 2 showed high antioxidant activity (IC(50) = 23.5 microM) in the DPPH free-radical assay and displayed cytotoxicity in the HCT-116 and SW-480 human colon cancer cell lines with IC(50) values of 154 and 134 microM, respectively.

Topics: Antioxidants; Biphenyl Compounds; Colonic Neoplasms; Drug Screening Assays, Antitumor; Flavonoids; Florida; Fruit; Humans; Inhibitory Concentration 50; Manilkara; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Phenols; Picrates; Polyphenols; Stereoisomerism; Structure-Activity Relationship; Tumor Cells, Cultured