benzofurans and caffeic-acid

Topics: 3,4-Dihydroxyphenylacetic Acid; Benzofurans; Biomass; Caffeic Acids; Chromatography, High Pressure Liquid; Cinnamates; Depsides; Eryngium; Flavonoids; Hydroxybenzoates; Plant Growth Regulators; Plant Shoots; Quercetin; Rosmarinic Acid

The purpose of this study is to reveal the impact of the plant hormone salicylic acid (SA) and methyl jasmonate (MeJA) on the growth, effective components accumulation, and related gene expression of the hairy root of Salvia przewalskii Maxim. Various concentrations of SA (0, 25, 50, 100, 200 μM) or MeJA (0, 50, 100, 200, 400, 600 μM) were added to the culture medium of Salvia przewalskii Maxim. Low concentrations of SA promoted the growth of hairy root, while a high concentration inhibited it. 0 to 400 μM MeJA promoted the growth of hairy root, but 600 μM MeJA starts to inhibit its growth. 50 μM SA and 400 μM MeJA significantly enhanced the production of caffeic acid, rosmarinic acid, salvianolic acid B, cryptotanshinone, and tanshinone IIA. In general, 50 μM SA can be used to accumulate of tanshinone in hairy roots of S. przewalskii with 6 days. 400 μM MeJA can be used to accumulate of phenolic acids in hairy roots of S. przewalskii with 3 days. The selected genes in the tanshinone and phenolic acid biosynthetic pathway were upregulated with elicitation. To obtain a higher yield and content of secondary metabolites, it is advisable to use 50 μM SA or 400 μM MeJA as the optimal doses to cultivate the hairy root of S. przewalskii. This study provides, for the first time, an efficient tanshinone and phenolic acid production method for S. przewalskii.

Topics: Abietanes; Acetates; Benzofurans; Caffeic Acids; Cinnamates; Cyclopentanes; Depsides; Dose-Response Relationship, Drug; Gene Expression Regulation, Plant; Hydroxybenzoates; Oxylipins; Phenanthrenes; Plant Growth Regulators; Plant Proteins; Plant Roots; Rosmarinic Acid; Salicylic Acid; Salvia; Time Factors

Danshen (Salvia miltiorrhiza, DS) and Honghua (Carthamus tinctorius, HH) are commonly used traditional Chinese medicines for activating blood and removing stasis, and DS-HH (DH) herbal pair had potential synergistic effects on promoting blood circulation. Therefore, it is essential to make clear the active components of this herbal pair for better understanding their potential synergistic effects.. To comprehensively evaluate the activity of DH herbal pair on physiological coagulation system of rats, and seek their potential active components by spectrum-effect relationship analysis.. The water extracts of DH herbal pair with different proportions (DS: HH = 1:1, 2:1, 3:1, 5:1, 1:5 and 1:3) were prepared. Male Sprague-Dawley rats were randomly divided into eight groups: blank group, model group, model + 1:1 (DH) group, model + 2:1 group, model + 3:1 group, model + 5:1 group, model + 1:5 group and model + 1:3 group. The intragastric administration was performed for eight times with 12 h intervals. SC40 semi-automatic coagulation analyzer was employed to determine coagulation indices. Meanwhile, HPLC and LC-MS were applied for chemical analyses of DH extracts. Finally, the active ingredients were screened by spectrum-effect relationship analysis and the activities of major predicted compounds were validated in vitro.. Different proportions of DH extracts could significantly prolong thrombin time (TT) and activated partial thromboplastin time (APTT), increase prothrombin time (PT) and decrease fibrinogen (FIB) content, reduced whole blood viscosity (WBV) and plasma viscosity (PV), decreased erythrocyte sedimentation rate blood (ESR) compared with model group. Furthermore, fifteen highly related components were screened out by the spectrum-effect relationship and LC-MS analysis, of which caffeic acid, salvianolic acid B, hydroxysafflor yellow A and lithospermate acid had significant blood-activing effect by prolong APTT and decrease FIB content at high (0.6 mM), medium (0.3 mM) and low (0.15 mM) (except lithospermate acid) concentrations in vitro.. DH herbal pair showed strong blood-activating effect on blood stasis rat through regulating the parameters involved in haemorheology and plasma coagulation system. Four active compounds, caffeic acid, salvianolic acid B, hydroxysafflor yellow A and lithospermate acid predicted by spectrum-effect relationship analysis had good blood-activating effect. Therefore, spectrum-effect relationship analysis is an effective approach for seeking active components in herbal pairs.

Topics: Animals; Benzofurans; Blood Coagulation; Blood Sedimentation; Caffeic Acids; Carthamus tinctorius; Chalcone; Chromatography, High Pressure Liquid; Drug Evaluation, Preclinical; Drugs, Chinese Herbal; Fibrinogen; Hemorheology; Male; Prothrombin Time; Quinones; Rats, Sprague-Dawley; Salvia miltiorrhiza

The study explored the isolation and characterisation of three compounds of high purity salvianolic acid B freeze-dried powder extracted from Salvia miltiorrhiza Bunge. A new salvianolic acid, salvianolic acid V (2) together with two known compounds (3-4) was identified. The antibacterial activity tests showed that compound 2 combined with clinical antibiotics such as Levofloxacin or Colistin sulphate together exhibited potent effects against MRSA or Acinetobacter baumanii. This report has considerably extended our knowledge about the diversity and bioactivity of caffeic acid derivatives from S. miltiorrhiza.

Topics: Acinetobacter baumannii; Alkenes; Anti-Bacterial Agents; Benzofurans; Caffeic Acids; Drug Evaluation, Preclinical; Drugs, Chinese Herbal; Freeze Drying; Methicillin-Resistant Staphylococcus aureus; Molecular Structure; Polyphenols; Powders; Salvia miltiorrhiza

In this study, we reported the analysis of the medium polarity fraction obtained from an accession of Helichrysum microphyllum subsp. tyrrhenicum from La Maddalena Island. Besides several compounds already evidenced in this species and related genera, i.e. micropyrone (1), arzanol (2), helipyrone (3), acetyl-bitalin derivatives (4, 5), gnaphaliol (6), caffeic acid (7), ursolic acid (8), 7-O-β-(D-glucopyranosyl)-5-methoxy-1(3H)-isobenzofuranone (9), gnaphaliol-9-O-β-D-glucopyranoside (11) and gnaphaliol-3-O-β-D-glucopyranoside (12), the presence of a new glycosidic phthalide, 6-O-β-(D-glucopyranosyl)-4-methoxy-1(3H)-benzofuranone (10), was evidenced for the first time, which resulted in a structural isomer of compound (9). The occurrence of this new benzofuranone derivative is an additional evidence of the deep intraspecific variability expressed by this species, which was also stated for the non-volatile components, and may be a distinctive trait of the population growing on La Maddalena Island.

Topics: Benzofurans; Caffeic Acids; Glucosides; Helichrysum; Italy; Molecular Structure; Monosaccharides; Phloroglucinol; Pyrones; Triterpenes; Ursolic Acid

To establish the HPLC fingerprint of water-soluble components of Salvia miltiorrhiza in Songtao, Guizhou, and to perform simultaneous determination of six components in it, so as to provide analytical method for its quality control.. The analyses were performed on a Phenomenex Luna C18 (2) (250 mm x 4. 6 mm, 5µm) column eluted with 0. 4% formic acid(A) - acetonitrile(B) in a gradient mode. The flow rate was 1. 0 mL/min, column temperature was set at 30 °C.. Eleven common peaks were identified form the HPLC fingerprint of Salvia miltiorrhiza from 10 batches, the HPLC fingerprint similarities of 10 batches were not less than 0. 999. The linear ranges of danshensu, protocatechuic aldehyde, caffeic acid, rosmarinic acid, lithospermic acid and salvianolic acid B were 0. 0680 ~ 1. 3583 mg/mL, 0. 0008 ~ 0. 3967 mg/mL, 0. 0005 ~ 0. 2660 mg/mL, 0. 0020 ~ 0. 3992 mg/mL, 0. 0063 ~ 0. 6311 mg/mL and 0. 0097 ~ 1. 9306 mg/mL with r ≥ 0. 9999, respectively. The recovery rates were 100. 84%,102. 44%, 100. 53% ,100. 63%, 100. 83% and 100. 35% with RSD <2. 3%, respectively.. The established method is simple, accurate and can provide reference for quality control of Salvia miltiorrhiza.

Topics: Benzaldehydes; Benzofurans; Caffeic Acids; Catechols; Chromatography, High Pressure Liquid; Cinnamates; Depsides; Drugs, Chinese Herbal; Lactates; Phytochemicals; Quality Control; Rosmarinic Acid; Salvia miltiorrhiza; Water

Fuzheng Huayu recipe (FZHY) was formulated on the basis of Chinese medicine theory in treating liver fibrosis. It has a significant efficacy against liver fibrosis caused by chronic hepatitis B, with the action mechanisms of inhibition of hepatic stellate cell activation, protection of hepatocyte oxidative injury and regulations of hepatic matrix remodeling etc.. To identify the absorbed components and metabolites of Danshen in FZHY in rat serum, and find their active components for anti-liver fibrosis.. A valid high performance liquid chromatography-electrospray ionization ion trap mass spectrometry (HPLC-ESI/MS(n)) method was established to investigate the absorbed and metabolized compounds of Danshen in FZHY in rat serum after oral administration. Mass spectra were acquired in both negative and positive modes. Otherwise, to evaluate the anti-hepatic fibrosis efficacies of absorbed and metabolized compounds, the LX-2 cell line of hepatic stellate cell (HSC), which was crucial cellular basis of fibrogenesis, was cultured and incubated with absorbed compounds, the cytotoxicity was determined with the cellomics Multiparameter Cytotoxicity Kit 1 by High Content Screening (HCS), the cell proliferation was assayed with EdU-DNA incorporation, and the cell activation was analyzed through α-smooth muscle actin (α-SMA) expression with high content screening technology.. More than 11 compounds and 2 metabolites from Danshen were identified in the serum after oral administration of FZHY by comparing their mass spectra and retention behavior with reference compounds or literature data. Among these compounds, there were no obvious changes in nuclear morphology, membrane permeability with blow 96 μM of six polar compounds treatment in comparison with control cells, respectively. And the salvianolic acid B (6 μM, 48 μM), caffeic acid (6 μM, 48 μM) and rosmarinic acid (48 μM) could obviously inhibit LX-2 cells proliferation, down-regulate α-SMA expression.. The results proved that the established method could be applied to analyze the absorbed into blood compounds of Danshen after oral administration FZHY. These absorbed compounds included 11 compounds and 2 metabolites of Danshen. Among them, the salvianolic acid B, caffeic acid and rosmarinic acid were the effective components of FZHY to anti-hepatic fibrosis effects.

Topics: Animals; Benzofurans; Caffeic Acids; Cell Membrane Permeability; Cell Proliferation; Cells, Cultured; Cinnamates; Depsides; Drugs, Chinese Herbal; Humans; Liver Cirrhosis; Male; Phenanthrolines; Rats; Rats, Wistar; Rosmarinic Acid; Salvia miltiorrhiza

Buglossoides purpureocaerulea is a little-known plant used in the folk tradition for the preparation of a decoction in Sud, Italy, where it is appreciated for its beneficial effects on liver diseases. These properties may be due to the presence of antioxidant compounds. This study presents the phenolic characterisation and the antioxidant activity (AA) of B. purpureocaerulea extracts obtained by decoction, ethanol infusion and ethanol and methanol macerations. Total phenols ranged between 69 and 100 mg g(-1 ) dry weight (DW). The main compounds were: rosmarinic acid, caffeic acid, lithospermic acid and salvianolic acid C. The extracts showed a good AA, particularly high for the decoction (142-283 µmol TE g(-1) DW; TE, Trolox equivalent) and ethanol maceration extract (214-364 µmol TE g(-1) DW) when determined by DPPH and ferric reducing antioxidant power test, respectively.

Topics: Alkenes; Antioxidants; Benzofurans; Biphenyl Compounds; Boraginaceae; Caffeic Acids; Cinnamates; Depsides; Free Radical Scavengers; Picrates; Plant Extracts; Polyphenols; Rosmarinic Acid

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

The present work investigated the effects of salicylic acid (SA) on the accumulation of phenolic compounds and the activities of PAL, TAT, SOD, CAT and POD enzymes in the Salvia miltiorrhiza cell culture. When SA is applied to the cell culture, phenolic compounds will increase and PAL, TAT, SOD, CAT, and POD enzymes will become more active. The accumulations of phenolic compounds and the PAL activity were stimulated 8h after the treatment with SA. The TAT activity was stimulated after 48 h. The resulting antioxidative enzymes' activities were greatly improved. SA elicitation on the phenolic acid accumulation was depended upon the application dosage and the time-duration. The suitable SA concentration for eliciting phenolic compound accumulations was 6.25-22.5mg/L. The elicitation effect of SA on phenolic compound accumulations correlated with the PAL activity, but not with the TAT activity. This indicates that PAL may be the key enzyme for the biosynthesis of salvianolic acid B and caffeic acid. The raised PAL activity leads to the improvement of the quantity of phenolic compounds. This could be of particular significance by using plant cell culture systems for biotechnological production of plant secondary metabolites such as salvianolic acid B and caffeic acid.

Topics: Benzofurans; Biomass; Caffeic Acids; Oxidoreductases; Phenylalanine Ammonia-Lyase; Plant Proteins; Salicylic Acid; Salvia miltiorrhiza; Tyrosine Transaminase

An anionic potato peroxidase (EC 1.11.1.7, APP) thought to be involved in suberization after wounding was isolated from slices of Solanum tuberosum in order to elucidate the first steps of dehydrogenative polymerization between pairs of different hydroxycinnamic acids (FA, CafA, CA and SA) present in wound-healing plant tissues. Use of a commercial horseradish peroxidase (HRP)-H2O2 catalytic system gave the identical major products in these coupling reactions, providing sufficient quantities for purification and structural elucidation. Using an equimolar mixture of pairs of hydroxycinnamic acid suberin precursors, only caffeic acid is coupled to ferulic acid and sinapic acid in separate cross-coupling reactions. For the other systems, HRP and APP reacted as follows: (1) preferentially with ferulic acid in a reaction mixture that contained p-coumaric and ferulic acids; (2) with sinapic acid in a mixture of p-coumaric and sinapic acids; (3) with sinapic acid in a mixture of ferulic and sinapic acids; (4) with caffeic acid in a reaction mixture of p-coumaric and caffeic acids. The resulting products, isolated and identified by NMR and MS analysis, had predominantly beta-beta-gamma-lactone and beta-5 benzofuran molecular frameworks. Five cross-coupling products are described for the first time, whereas the beta-O-4 dehydrodimers identified from the caffeic acid and sinapic acid cross-coupling reaction are known materials that are highly abundant in plants. These reactivity trends lead to testable hypotheses regarding the molecular architecture of intractable suberin protective plant materials, complementing prior analysis of monomeric constituents by GC-MS and polymer functional group identification from solid-state NMR, respectively.

Topics: Benzofurans; Caffeic Acids; Catalysis; Coumaric Acids; Cross-Linking Reagents; Dimerization; Free Radical Scavengers; Gas Chromatography-Mass Spectrometry; Horseradish Peroxidase; Lactones; Magnetic Resonance Spectroscopy; Peroxidase; Propionates; Solanum tuberosum

The six phenolic constituents are water-soluble components extracted from the Chinese medical herb danshen, the dried roots of Salvia miltiorrhiza Bunge (Labiatae). An liquid chromatography/tandem mass spectrometry (LC/MS/MS)-based method has been developed for the simultaneous quantification of six phenolic constituents of danshen (magnesium lithospermate B (MLB), rosmarinic acid (RA) and lithospermic acid (LA), caffeic acid (CAA), protocatechuic aldehyde (3,4-dihydroxybenzaldehyde, Pal), 3,4-dihydroxyphenyllactic acid (danshensu)) in human serum with chloramphenicol as internal standard. The serum samples were treated by special liquid-liquid extraction, and the analytes were determined using electrospray negative ionization mass spectrometry in the multiple reaction monitoring (MRM) mode, with sufficient sensitivity to allow analysis of human serum samples generated following administration of a clinically relevant dose. Good linearity over the range 8-2048 ng/mL for six phenolic constituents was observed. The intra- and inter-day precisions (CV) of analysis were <13%, and the accuracy ranged from 88 to 116%. This quantitation method was successfully applied to a pharmacokinetic study of i.v. drip infusion of Danshen injection fluid in human.

Topics: Benzaldehydes; Benzofurans; Caffeic Acids; Catechols; Chromatography, Liquid; Cinnamates; Depsides; Drug Stability; Drugs, Chinese Herbal; Humans; Lactates; Phenols; Reproducibility of Results; Rosmarinic Acid; Salvia miltiorrhiza; Sensitivity and Specificity; Spectrometry, Mass, Electrospray Ionization

To study the chemical constituents of the water-extracts of Selaginella tamariscina (Beauv.) Spring.. Various chromatographic techniques were used to separate and purify the constituents. Their physico-chemical properties and spectral data were used to elucidate the structures.. Nine compounds were isolated and identified as (2R,3S)-dihydro-2- (3',5'-dimethoxy-4'-hydroxyphenyl)-7-methoxy-5-acetyl-benzofuran (1), 3-hydroxy-phenpropionic acid-(2'-methoxy-4'-carboxy-phenol) ester (tamariscina ester A, 2), sygringaresinol (3), 1-(4'-hydroxyl-3'-methoxyphenyl)glycerol (4), ferulic acid (5), caffeic acid (6), vanillic acid (7), syringic acid (8), and umbelliferone (9).. Compound 1 and 2 are new compounds, and the others were isolated from Selaginella for the first time.

Topics: Benzofurans; Caffeic Acids; Coumaric Acids; Molecular Conformation; Molecular Structure; Phenylpropionates; Plants, Medicinal; Selaginellaceae; Vanillic Acid

Two phenylpropanoid sucrose esters were isolated from dry rhizomes of Canna edulis Ker Gawl., along with a known phenylpropanoid sucrose ester and four known phenylpropanoids. On the basis of analysis of spectroscopic data and chemical evidence, these two phenylpropanoid sucrose esters were shown to be 3-O-p-coumaroyl-6-O-feruloyl-beta-D-fructofuranosyl 6-O-acetyl-alpha-D-glucopyranoside and 3,6-di-O-p-coumaroyl-beta-D-fructofuranosyl 6-O-acetyl-alpha-D-glucopyranoside.

Topics: Benzofurans; Caffeic Acids; Chromatography, High Pressure Liquid; Cinnamates; Depsides; Esters; Magnetic Resonance Spectroscopy; Marantaceae; Molecular Structure; Optical Rotation; Phenylpropionates; Rosmarinic Acid; Sucrose

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