lignans and caffeic-acid

Monolignin alcohols (type H, type G and type S) are the basic units of lignin and lignans in plants, and their composition differences directly determine the chemical diversity and biological activity of lignin and lignans. Caffeic acid

Topics: Alcohols; Caffeic Acids; Lignans; Lignin; Methyltransferases; Plants

Phenolic plant constituents are well known for their health-promoting and cancer chemopreventive properties, and products containing such constituents are therefore readily consumed. In the present work, we isolated 13 phenolic constituents of four different compound classes from the aerial parts of the Moldavian dragonhead, an aromatic and medicinal plant with a high diversity on secondary metabolites. All compounds were tested for their apoptotic effect on myeloma (KMS-12-PE) and AML (Molm-13) cells, with the highest activity observed for the flavone and flavonol derivatives. While diosmetin (

Topics: Cell Line, Tumor; Flavones; Flavonols; Lamiaceae; Leukemia, Myeloid, Acute; Lignans; Multiple Myeloma; Phenols

Topics: Animals; Apoptosis; Caffeic Acids; Cells, Cultured; Hydrogen Peroxide; Lamiaceae; Lignans; Molecular Structure; Myocytes, Cardiac; Plant Extracts; Protective Agents; Rats; Spectrum Analysis

Warfarin is a commonly used anticoagulant drug and is a derivate of coumarin. Cytochrome P450 2C9 (CYP2C9) plays the key role in transformation of coumarin and thus, influences determination of warfarin dosage. A number of factors including dietary compounds such as sesamin, caffeic acid and ferulic acids can regulate the activity of CYP2C9. The present study tested the hypothesis that sesamin, episesamin, caffeic acid and ferulic acid decreases the rate of warfarin 7-hydroxylation via inhibition of hepatic CYP2C9. The experiments were conducted on hepatic microsomes from human donors. It was demonstrated that the rate of 7-hydroxylation of warfarin was significantly decreased in the presence of sesamin in the range of concentrations from 5 to 500 nM, and was not affected by episesamin, caffeic acid and ferulic acid in the same range of concentrations. The kinetic analysis indicated non-competitive type of inhibition by sesamin with Ki = 202 ± 18 nM. In conclusion, the results of our in vitro study revealed that sesamin was able to inhibit formation of a major metabolite of warfarin, 7-hydroxywarfarin. The potentially negative consequences of the consumption of high amounts of sesamin-containing food or dietary supplements in warfarin-treated patients need to be further studied.

Topics: Anticoagulants; Caffeic Acids; Coumaric Acids; Dietary Supplements; Dioxoles; Female; Food; Humans; Hydroxylation; Inhibitory Concentration 50; Kinetics; Lignans; Male; Microsomes, Liver; Warfarin

A new caffeate compound, (E)-erythro-syringylglyceryl caffeate (1), was isolated from the roots and rhizomes of Nardostachys chinensis Batal., together with nine known phenolic compounds, including (+)-licarin A (2), naringenin 4', 7-dimethyl ether (3), pinoresinol-4-O-β-D-glucoside (4), caraphenol A (5), Z-miyabenol C (6), protocatechuic acid (7), caffeic acid (8), gallic acid (9) and vanillic acid (10). Their chemical structures were elucidated on the basis of spectroscopic data and physicochemical properties. Furthermore, this is the first report of compounds 2, 5 and 6 from Nardostachys genus.

Topics: Caffeic Acids; Flavanones; Furans; Glucosides; Hydroxybenzoates; Lignans; Nardostachys; Plant Roots; Rhizome; Vanillic Acid

Yunnaneic acids A-D, isolated from the roots of Salvia yunnanensis , are hexameric (A and B) and trimeric (C and D) assemblies of caffeic acid that feature an array of synthetically challenging and structurally interesting domains. In addition to being caffeic acid oligomers, yunnaneic acids A and B are formally dimeric and heterodimeric adducts of yunnaneic acids C and D. Herein we report the first total syntheses of yunnaneic acids C and D featuring the formation of their bicyclo[2.2.2]octene cores in a single step from simple precursors via an oxidative dearomatization/Diels-Alder cascade that may have biogenetic relevance. In addition, exploitation of the key intermediate resulting from this cascade reaction has enabled rapid access to the structurally related caffeic acid metabolite rufescenolide through an unexpected Lewis acid-mediated reduction. Finally, we report the results of extensive model studies toward forming the dimeric yunnaneic acids A and B. These explorations indicate that the innate reactivities of the monomeric fragments do not favor spontaneous formation of the desired dimeric linkages. Consequently, enzymatic involvement may be required for the biosynthesis of these more complex family members.

Topics: Bridged Bicyclo Compounds; Caffeic Acids; Cycloaddition Reaction; Lignans; Phenols; Stereoisomerism

Benzo[kl]xanthene lignans, promising bioactive polyphenols obtained by biomimetic oxidative coupling of caffeic acid derivatives, react efficiently with peroxyl radicals in both polar and non-polar solvents, thanks to the simultaneous presence of guaiacol-like and catechol-like OH-groups.

Topics: Caffeic Acids; Catechols; Free Radicals; Guaiacol; Lignans; Peroxides; Xanthenes

Antioxidants could be promising agents for management of oxidative stress-related diseases. New biologically active compounds, belonging to a rare class of natural lignans with antiangiogenic, antitumoral and DNA intercalating properties, have been recently synthesized. These compounds are benzo[kl]xanthene lignans (1,2) and dihydrobenzofuran neolignans (3,4). The radical scavenging and chain-breaking antioxidant activities of compounds 1-4 were studied by applying different methods: radical scavenging activity by DPPH rapid test, chain-breaking antioxidant activity and quantum chemical calculations. All studied compounds were found to be active as DPPH scavengers but reaction time with DPPH and compounds' concentrations influenced deeply the evaluation. The highest values of radical scavenging activity (%RSAmax) and largest rate constants for reaction with DPPH were obtained for compounds 2 and 3. Comparison of %RSAmax with that of standard antioxidants DL-α-tocopherol (TOH), caffeic acid (CA) and butylated hydroxyl toluene (BHT) give the following new order of %RSA max: TOH (61.1%) > CA (58.6%) > 3 (36.3%) > 2 (28.1%) > 4 (6.7%) > 1 (3.6%) = BHT (3.6%). Chain-breaking antioxidant activities of individual compounds (0.1-1.0 mM) and of their equimolar binary mixtures (0.1 mM) with TOH were determined from the kinetic curves of lipid autoxidation at 80 °C. On the basis of a comparable kinetic analysis with standard antioxidants a new order of the antioxidant efficiency (i.e., protection factor, PF) of compounds 1-4 were obtained: 2 (7.2) ≥ TOH (7.0) ≥ CA (6.7) > 1 (3.1) > 3 (2.2) > ferulic acid FA (1.5) > 4 (0.6); and of the antioxidant reactivity (i.e. inhibition degree, ID): 2 (44.0) >> TOH (18.7) >> CA (9.3) >> 1 (8.4) > 3 (2.8) > FA (1.0) > 4 (0.9). The important role of the catecholic structure in these compounds, which is responsible for the high chain-breaking antioxidant activity, is discussed and a reaction mechanism is proposed. Higher oxidation stability of the lipid substrate was found in the presence of equimolar binary mixtures 2 + TOH, 3 + TOH and 4 + TOH. However, an actual synergism was only obtained for the binary mixtures with compounds 3 and 4. The geometries of compounds and all possible phenoxyl radicals were optimized using density functional theory. For description of the scavenging activity bond dissociation enthalpies (BDE), HOMO energies and spin densities were employed. The best correlation between theoretical and experimental d

Topics: alpha-Tocopherol; Antioxidants; Benzofurans; Biphenyl Compounds; Butylated Hydroxytoluene; Caffeic Acids; Free Radical Scavengers; Hot Temperature; Kinetics; Lignans; Lipids; Oxidation-Reduction; Phenols; Picrates; Quantum Theory; Solutions; Structure-Activity Relationship; Thermodynamics; Xanthenes

A simple and reliable ultra performance liquid chromatography coupled with electrospray ionization time-of-flight mass spectrometry method (UPLC-TOF-MS) was developed and validated for the simultaneous determination of the major bioactive constituents in Acanthopanax senticosus and its extract. The separation of five compounds was performed on a UPLC™ HSS T3 column (100 mm × 2.1 mm, 1.7 μm) with gradient elution using a mobile phase consisting of 0.1% aqueous formic acid and acetonitrile containing 0.1% formic acid. All targeted compounds (syringin, chlorogenid acid, caffeic acid, eleutheroside E and isofraxidin) were baseline separated within 5.3 min in samples, which represented an approximate six-fold reduction in the analysis time in comparison to published HPLC method. Quantitation was carried out working in the V mode using the narrow widow extracted ion chromatograms (nwXICs) of each compound (extracted using a 20 mDa window). Furthermore, all calibration curves showed good linearity (r > 0.999) within the test ranges. The precision was evaluated by intra- and inter-day tests, which revealed relative standard deviation (RSD) values of less than 3.88%. The recoveries for the quantified compounds were between 96.3% and 103.7%, with RSD values below 2.89%. According to the literature, this study represents the first investigation of the simultaneous analysis of multiple components and the method can be applied to determine the amounts of the major compounds in Acanthopanax senticosus and its extract by UPLC-TOF-MS.

Topics: Caffeic Acids; Calibration; Chlorogenic Acid; Chromatography, High Pressure Liquid; Coumarins; Eleutherococcus; Glucosides; Lignans; Limit of Detection; Organic Chemicals; Phenylpropionates; Plant Extracts; Principal Component Analysis; Reference Standards; Reproducibility of Results; Spectrometry, Mass, Electrospray Ionization

To investigate the chemical constituents from the tubers of Ipomoea batata.. The chemical constituents were isolated and purified by solvent extraction together with various chromatographic techniques. The structures were elucidated on the basis of physiochemical property and spectral data.. 6 compounds were identified from the CHCl3 extract as Batatinoside I (1), citrusin C(2), octadecyl caffeate (3), beta-amyrin acetate (4), caffeic acid (5), scopoletin (6).. Compound 1 is isolated from Ipomoea batata for the first time.

Topics: Alkaloids; Caffeic Acids; Glycosides; Ipomoea batatas; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Oleanolic Acid; Plant Tubers; Scopoletin; Spectroscopy, Near-Infrared

Phenolic compounds were extracted from defatted flaxseeds using ethanol-dioxane (1:1, v/v). The crude extract obtained was purified using Amberlite XAD-16 column chromatography with water and methanol as mobile phases. RP-HPLC and SE-HPLC showed a lignan macromolecule (LM) as a dominant phenolic compound in the purified extract. After the alkaline hydrolysis of LM caffeic acid glucoside (CaAG) was isolated using a semi-preparative HPLC and its structure was confirmed by LC-ESI-MS. In LM of the investigated flaxseed, one molecule of caffeic acid corresponded with five molecules of p-coumaric acid and two molecules of ferulic acid. The presence of caffeic acid in the lignan molecule might be very beneficial due to its high antioxidant activity.

Topics: Caffeic Acids; Chromatography, High Pressure Liquid; Coumaric Acids; Flax; Glucosides; Lignans; Macromolecular Substances; Mass Spectrometry; Molecular Structure; Plant Extracts; Polymers; Propionates; Seeds

To investigate the chemical constituents of Kalopanax septemlobus.. Chromatographic techniques including silica gel, gel, semi-preparative HPLC and PTLC as well as recrystallization were employed in the isolation and purification, and the structures were elucidated by spectral analysis and physical and chemical properties.. 6 compounds were identified as liriodendrin (1), (-) -syringarenol (2), trans-coniferyl aldehyde (3), trans-caffeic acid (4), beta-daucosterol (5), beta-sitosterol (6).. Compounds 2 -5 are obtained from this genus for the first time.

Topics: Acrolein; Aldehydes; Caffeic Acids; Furans; Kalopanax; Lignans; Molecular Structure; Plant Bark; Plant Roots; Plants, Medicinal; Sitosterols

To study the chemical constituents from Glehnia littoralis, macroreticular resin column chromatography, repeated column chromatography on Sephadex LH-20 and reverse phase ODS were used to isolate the compounds whose structures were elucidated based on spectroscopic data (ESI-MS, 1D and 2DNMR). From EtOAc-soluble fraction of the ethanol extracts, a new 8-O-4' neolignan was isolated and named as glehlinoside D (1), along with five known compounds: (-)-secoisolariciresinol (2), ferulic acid (3), caffeic acid (4), vanillic acid (5) and syringin (6). Compound 1 is a new 8-O-4' neolignan.

Topics: Apiaceae; Butylene Glycols; Caffeic Acids; Lignans; Molecular Structure; Plants, Medicinal

Cell suspension cultures of Phyllanthus niruri were used to study the lignan profiles and biosynthesis. Suspension cultures yielded two lignans: the new cubebin dimethyl ether (1) and urinatetralin (2), a new lignan from P. niruri, but reported earlier from P. urinaria. This is the first report of cell suspension cultures of P. niruri that successfully produce lignans. Feeding 0.5 mM ferulic acid or 0.5 mM caffeic acid, being early precursors of lignan biosynthesis, resulted in an increase up to 0.7 mg g(-1) DW of 1 (control value 0.1 mg g(-1) DW) and up to 0.3 mg g(-1) DW of 2 (control value 0.2 mg g(-1) DW). Comparison of the lignan profiles of cell suspensions, callus cultures, aerial plant parts, roots, and seeds showed significant differences.

Topics: Caffeic Acids; Coumaric Acids; Lignans; Molecular Structure; Phyllanthus; Plant Roots; Plants, Medicinal; Seeds

Estimation of dietary intake of polyphenols is difficult, due to limited availability of food composition data and bias inherent to dietary assessment methods. The aim of the present study was to evaluate the associations between the intake of polyphenol-rich foods and the urinary excretion of several phenolic compounds and therefore explore whether these phenolic compounds could be used as a biomarker of intake. Fifty-three participants of the SU.VI.MAX study (a randomised primary-prevention trial evaluating the effect of daily antioxidant supplementation on chronic diseases) collected a 24 h urine and a spot urine sample and filled a dietary record during a 2 d period. Thirteen polyphenols and metabolites, chlorogenic acid, caffeic acid, m-coumaric acid, gallic acid, 4-O-methylgallic acid, quercetin, isorhamnetin, kaempferol, hesperetin, naringenin, phloretin, enterolactone and enterodiol, were measured using HPLC-electrospray ionisation-MS-MS. In spot samples apple consumption was positively correlated to phloretin, grapefruit consumption to naringenin, orange to hesperetin, citrus fruit consumption to both naringenin and hesperetin, with r coefficients ranging from 0.31 to 0.57 (P < 0.05). The combination of fruits and/or fruit juices was positively correlated to gallic acid and 4-O-methylgallic acid, isorhamnetin, kaempferol, hesperetin, naringenin and phloretin (r 0.24-0.44, P < 0.05). Coffee consumption was positively correlated to caffeic and chlorogenic acids (r 0.29 and 0.63, P < 0.05 respectively). Black tea and wine consumption were positively correlated with gallic and 4-O-methylgallic acids (r 0.37-0.54, P < 0.001). The present results suggest that several polyphenols measured in a spot urine sample can be used as biomarkers of polyphenol-rich food intake.

Topics: 4-Butyrolactone; Adult; Antioxidants; Biomarkers; Caffeic Acids; Chlorogenic Acid; Coffee; Cohort Studies; Diet; Female; Flavonoids; Food; Fruit; Gallic Acid; Humans; Hydroxybenzoates; Kaempferols; Lignans; Male; Middle Aged; Phenols; Polyphenols; Vegetables; Wine

A chemosystematic study of the subtribe Scorzonerinae, a subtribe of the Lactuceae tribe of the Asteraceae family was performed, using the recently discovered tyrolobibenzyls as well as lignans and caffeic acid derivatives as diagnostic characters. In addition to the known compounds two new tyrolobibenzyls (E and F) were isolated and their structures were established by mass spectrometry and 1D and 2D NMR spectroscopy. Twenty four samples from rootstocks of seventeen different Scorzonerinae taxa, comprising members of three genera (Podospermum, Scorzonera, and Tragopogon), were analyzed. Tyrolobibenzyls A (1), B (2), C (5), D (3), E (6), and F (4) were identified in crude extracts by means of HPLC retention times, on-line UV spectra and on-line MS/MS spectra. Quantification of these compounds was performed by HPLC, using 2,2-bis-(4-hydroxyphenyl)-propane as an internal standard. Tyrolobibenzyls A-F were only detected in samples from Scorzonera humilis, while chlorogenic acid and 3,5-dicaffeoylquinic acid were detected in all samples investigated. In contrast, caffeoyl tartaric acid and cichoric acid were not detectable in any member of the subtribe Scorzonerinae.

Topics: Asteraceae; Benzofurans; Caffeic Acids; Chromatography, High Pressure Liquid; Europe; Lignans; Mass Spectrometry; Nuclear Magnetic Resonance, Biomolecular; Plant Roots