lignans and ferulic-acid

Tocotrienol (T3), unsaturated vitamin E, is gaining a lot of attention owing to its potent anticancer effect, since its efficacy is much greater than that of tocopherol (Toc). Various factors are known to be involved in such antitumor action, including cell cycle arrest, apoptosis induction, antiangiogenesis, anti-metastasis, nuclear factor-κB suppression, and telomerase inhibition. Owing to a difference in the affinity of T3 and Toc for the α-tocopherol transfer protein, the bioavailability of orally ingested T3 is lower than that of Toc. Furthermore, cellular uptake of T3 is interrupted by coadministration of α-Toc in vitro and in vivo. Based on this, several studies are in progress to screen for molecules that can synergize with T3 in order to augment its potency. Combinations of T3 with chemotherapeutic drugs (e.g., statins, celecoxib, and gefitinib) or dietary components (e.g., polyphenols, sesamin, and ferulic acid) exhibit synergistic actions on cancer cell growth and signaling pathways. In this review, we summarize the current status of synergistic effects of T3 and an array of agents on cancer cells, and discuss their molecular mechanisms of action. These combination strategies would encourage further investigation and application in cancer prevention and therapy.

Topics: Antineoplastic Agents; Catechin; Coumaric Acids; Dietary Supplements; Dioxoles; Drug Synergism; Drug Therapy, Combination; Humans; Lignans; Neoplasms; Resveratrol; Stilbenes; Tocotrienols

The effects of roasting and in vitro digestion on total phenolic content (TPC), total flavonoid content (TFC), phenolic profiles, and antioxidant activity of water-soluble extracts from six varieties of sesame were investigated in this study. Our results showed that the major phenolic compounds in raw, roasted and digested sesame were gallic acid (GA), protocatechuic acid (PA), 4-hydroxybenzoic acid (4 HBA), ferulic acid (FA) and quercetin (Quer). Roasting significantly increased the TPC, pinoresinol diglucoside (PD), sesamol, as well as the content of phenolic compounds (especially GA, PA, 4 HBA and Quer) in sesame, but kept or reduced the TFC, sesamin and sesamolin. After roasting, the antioxidant potency composite index (ACI) of six varieties of sesame was significantly increased by 29.8%-216.6%. Additionally, the ACI of gastric digestion was significantly higher than that of oral and intestinal digestion during the in vitro digestion of the roasted-sesame, except for the varieties of Ganzhi 9 and Ganzhi 17. This study showed that five phenolic compounds (GA, PA, 4 HBA, p-coumaric acid, Quer) and sesamol of the water-soluble extracts contributed to the antioxidant activities of the digestive products of sesame.

Topics: Anticarcinogenic Agents; Antioxidants; Benzodioxoles; Coumaric Acids; Digestion; Dioxoles; Flavonoids; Gallic Acid; Hydroxybenzoates; Lignans; Parabens; Phenol; Phenols; Plant Extracts; Principal Component Analysis; Propionates; Quercetin; Seeds; Sesamum

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

Topics: Acetates; Antineoplastic Agents, Phytogenic; Coumaric Acids; Culture Media; Cyclopentanes; Flax; Lignans; Molecular Structure; Oxylipins; Plant Roots; Tissue Culture Techniques

Epidemiological studies present the beneficial effects of dietary habits on prevention of aging-associated decline of brain function. Phytochemicals, the second metabolites of food, protect neuronal cells from cell death in cellular models of neurodegenerative disorders, and the neuroprotective activity has been ascribed to the anti-oxidant and anti-inflammatory functions. In this paper, the cellular mechanism of neuroprotection by phytochemicals was investigated, using the cellular model of mitochondrial apoptosis induced by PK11195, a ligand of outer membrane translocator protein, in SH-SY5Y cells. PK11195 induced mitochondrial membrane permeabilization with rapid transit production of superoxide (superoxide flashes) and calcium release from mitochondria, and activated apoptosis signal pathway. Study on the structure-activity relationship of astaxanthin, ferulic acid derivatives, and sesame lignans revealed that these phytochemicals inhibited mitochondrial membrane permeabilization and protected cells from apoptosis. Ferulic acid derivatives and sesame lignans inhibited or enhanced the mitochondrial pore formation and cell death by PK11195 according to their amphiphilic properties, not directly depending on the antioxidant activity. Regulation of pore formation at mitochondrial membrane is discussed as a novel mechanism behind neuroprotective activity of phytochemicals in aging and age-associated neurodegenerative disorders, and also behind dual functions of phytochemicals in neuronal and cancer cells.

Topics: Apoptosis; Calcium; Cations, Divalent; Cell Line, Tumor; Cell Survival; Coumaric Acids; Dioxoles; Humans; Hydrophobic and Hydrophilic Interactions; Isoquinolines; Lignans; Mitochondrial Membrane Transport Proteins; Mitochondrial Membranes; Neuroprotective Agents; Oxygen; Permeability; Phytochemicals; Proto-Oncogene Proteins c-bcl-2; Reactive Oxygen Species; Xanthophylls

Lignan natural products comprise a broad spectrum of biologically active secondary metabolites. Their structural diversity belies a common biosynthesis, which involves regio- and chemoselective oxidative coupling of propenyl phenols. Attempts to replicate this oxidative coupling have revealed significant challenges for controlling selectivity, and these challenges have thus far prevented the development of a unified biomimetic route to compounds of the lignan family. A practical solution is presented that hinges on oxidative ring opening of a diarylcyclobutane to intercept a putative biosynthetic intermediate. The effectiveness of this approach is demonstrated by the first total synthesis of tanegool in 4 steps starting from ferulic acid, as well as a concise synthesis of the prototypical furanolignan pinoresinol.

Topics: Biomimetics; Coumaric Acids; Furans; Lignans; Oxidation-Reduction; Phenols

To study the chemical consistuents of Tamarix chinensis.. The compounds were isolated and purified by column chromatography and their structures were elucidated through spectroscopic analysis.. Nine compounds were isolated and identified as isotamarixen(1), matairesinol(2), tetepathine(3), kaempferol(4), 4'-methylkaempferol(5),4',7-dimethylkaempferol (6), hexacosyl-3-caffeate(7), ferulic acid(8) and 3-methoxyl methyl gallate(9).. Compounds 1-3,7 and 8 are isolated from this plant for the first time, compounds 1-3,7 are isolated from Tamarix genus for the first time.

Topics: Coumaric Acids; Flavonoids; Furans; Lignans; Magnetic Resonance Spectroscopy; Plant Leaves; Resins, Synthetic; Tamaricaceae; Triterpenes

To study the chemical constituents of the dichloromethane extract from pine needles of Cedrus deodara.. The chemical constituents were isolated and purified from the dichloromethane extract of pine needles by chromatography on silica gel and Sephadex LH-20. Their structures were elucidated by analysis of spectral data and chemical properties.. Seven compounds were isolated and their chemical structures were identified as ferulic acid (1), osthole (2), beta-phenylacrylic acid (3), paeonol (4), beta-sitosterol (5), magnolol (6) and honokiol (7).. Compounds 1 - 4, 6 and 7 are isolated from this plant for the first time.

Topics: Acetophenones; Biphenyl Compounds; Cedrus; Chromatography, Thin Layer; Coumaric Acids; Coumarins; Lignans; Methylene Chloride; Molecular Structure; Plant Leaves

To separate and identify chemical constituents from Coptis chinensis.. The compounds were separated and purified by various chromatographic techniques. Their structures were identified on the basis of their physicochemical properties using spectral techniques such as NMR and MS.. Thirteen compounds were separated from ethanol extracts of C. chinensis, including seven lignans, three simple phenylpropanoids, two flavones and one phenolic acid, and identified as erythro-guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether (1), threo-guaiacylglycerol-8-O-4'-(coniferyl alcohol) ether (2), (+)-pinoresinol (3), (+)-medioresinol (4), (+)-lariciresinol (5), (+)-5'-methoxylariciresinol (6), (+)-isolariciresinol (7), chlorogenic acid (8), ferulic acid (9), Z-octadecyl caffeate (10), rhamnetin (11), wogonin (12), and vanillic acid (13).. Compounds 1, 2, 4, 6, 10-13 were separated from the genus Coptis for the first time.

Topics: Caffeic Acids; Chlorogenic Acid; Coptis; Coumaric Acids; Ethanol; Flavanones; Flavones; Furans; Hydroxybenzoates; Lignans; Lignin; Naphthols; Quercetin; Vanillic Acid

To study the chemical constituents of Gentiana striata.. The constituents were isolated from the whole herb of Gentiana striata by recrystalization, silica gel column chromatography, polyamide column chromatography and Sephadex LH-20,etc. Their structures were elucidated through MS, 1H-NMR, 13C-NMR.. -8 compounds were isolated and identified as: Desoxyloganin (1), Gmephiloside (2), 5,7,4'-trihydroxy-3'-methoxyflavone (3), (+)-8-hydroxypinoresinol (4) 3S,5R, 6R, 9S-tetra-hydroxymegastigmane (5), Quercetin-3-O-beta-D-glucoside (6), Ferulic acid (7) and Ursolic acid (8).. All the compounds are isolated for the first time from Gentiana striata.

Topics: Coumaric Acids; Flavonoids; Gentiana; Glucosides; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Quercetin; Triterpenes; Ursolic Acid

To study the chemical constituents of the roots of Vaccinium bracteatum.. The constituents were separated and purified with chromatographic methods (including silica gel, Sephadex LH-20 and RP-18 column chromatography), and their structures were determined by spectroscopic methods (including MS, 1H-NMR and 13C-NMR).. 10 compounds were isolated from the roots of Vaccinium bracteatu and were elucidated as chlorogenic acid (1), pinoresinol (2), ferulic acid (3), kaempferol (4), trans-caffeic acid (5), beta-sitosterol (6), quercetin (7), oleanolic acid (8), apigenin (9) and luteolin (10).. Compounds 1 -3 are obtained from this plant for the first time.

Topics: Chlorogenic Acid; Coumaric Acids; Furans; Kaempferols; Lignans; Magnetic Resonance Spectroscopy; Plant Roots; Quercetin; Solvents; Vaccinium

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 study the chemical constituents of roots and stems of Nardostachys chinensis.. The chemical constituents were isolated and purified by column chromatography including silica gel, Diaion HP-20, Sephadex LH-20, ODS, and HPLC. Their structures were elucidated on the basis of spectral data analyses.. Six compounds were isolated and identified as 8-hydroxypinoresinol-4-O-beta-D-glucopyranoside (1), 8-hydroxypinoresinol-4'-O-beta-D-glucopyranoside (2), 8-hydroxypinoresinol-4-O-(beta-D-glucopyranosyl) 4'-O-beta-D-glucopyranoside (3), cycloolivil 6-O-beta-D-glucopyranoside(4), ferulic acid (5), chlorogenic acid methyl ester (6).. All the compounds are isolated from this genus for the first time.

Topics: Chlorogenic Acid; Chromatography, High Pressure Liquid; Coumaric Acids; Glucosides; Lignans; Magnetic Resonance Spectroscopy; Nardostachys; Plant Roots; Plant Stems; Plants, Medicinal; Solvents

An HPLC-photodiode array (PDA) detection method was established for the simultaneous determination of 12 components in Xiao-Yao-San-Jia-Wei (XYSJW): geniposide, puerarin, paeoniflorin, ferulic acid, liquiritin, hesperidin, naringin, paeonol, daidzein, glycyrrhizic acid, honokiol, and magnolol. These were separated in less than 70 min using a Waters Symmetry Shield RP 18 column with gradient elution using (A) acetonitrile, (B) water, and (C) acetic acid at a flow rate of 1 ml/min, and with a PDA detector. All calibration curves showed good linear regression (r(2)>0.9992) within the test ranges. The method was validated for specificity, accuracy, precision, and limits of detection. The proposed method enables in a single run the simultaneous identification and determination for quality control of 12 multi-structural components of XYSJW forming the basis of its therapeutic effect.

Topics: Acetophenones; Benzoates; Biphenyl Compounds; Bridged-Ring Compounds; Coumaric Acids; Drugs, Chinese Herbal; Flavanones; Glucosides; Glycyrrhizic Acid; Hesperidin; Iridoids; Isoflavones; Lignans; Medicine, Chinese Traditional; Molecular Structure; Monoterpenes; Quality Control; Reference Standards; Reproducibility of Results; Sensitivity and Specificity

To study the chemical constituents of Salsola collina.. The EtOH extract from the whole plant of S. collina were isolated and purified by column chromatography. These compounds were identified by their physical properties and spectroscopic data.. Eleven compounds were isolated and identified as ferulic acid (1), p-coumaric acid (2), salicylic acid (3), tricin (4), selagin (5), acanthoside D (6), tricin -7-O-beta-D-glucopyranoside (7), tricin-4'-O-beta-D-apioside (8), isorhamnetin-7-O-beta-D-glucopyranoside (9), isorhamnetin-3-O-beta-D-glucopyranoside (10), isorhamnetin-3-O-alpha-L-arabinopyranosyl (1-->6) -beta-D-glucopyranoside (11).. wherein compound 1, 2, 3, 5, 6 and 9 were isolated from the Salsola for the first time.

Topics: Coumaric Acids; Flavonols; Furans; Glucosides; Lignans; Plants, Medicinal; Salsola

To study the bioactive constituents of the fresh rhizome of Pinellia ternata, and provide the scientific basis for quality control.. Various chromatographic techniques were used to separate and purify the chemical constituents, and their chemical structures were determined on the basis of physical-chemical properties and spectroscopic analysis. The inhibitory effects of the isolated compounds on tumor necrosis factor (TNF)-alpha production in the peritoneal macrophages of mice stimulated with lipopolysaccharide (LPS) were assayed in vitro by microplate colorimetric method.. Nine compounds were isolated and identified as (E)-p-coumaryl alcohol (1), 3, 4-dihydroxycinnamyl alcohol (2), ferulic acid (3), lariciresinol (4), erythro-guaiacylglycerol-beta-O-4'-sinapyl ether (5), dehydrodiconiferyl alcohol (6) , isolariciresinol (7) , sachaliside 1 (8) and coniferin (9). The inhibitory effect of compounds 1, 2, 3, 8, and 9 were 24.1% , 57.6% , 40.2% , 82.7% , and 62.0% , respectively, against the TNF-alpha production in the peritoneal macrophages of mice stimulated with LPS at a concentration of 10(-5) mol L(-1) in vitro.. The compounds 1, 2 and 4-8 from genera Pinellia Ten. and compound 9 from P. ternata were isolated for the first time. The compounds 1, 2, 8 and 9 were phenylpropanoids, and 4-7 were lignanoids. The anti-inflammatory effects of the rhizome of P. ternata might relate at the least to compounds 1, 2, 3, 8 and 9.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Cells, Cultured; Cinnamates; Coumaric Acids; Furans; Lignans; Macrophages, Peritoneal; Male; Mice; Mice, Inbred C57BL; Molecular Structure; Pinellia; Plants, Medicinal; Rhizome; Tumor Necrosis Factor-alpha

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

Cell cultures of Linum album Kotschy ex Boiss. (Linaceae) showing high accumulation of the lignan podophyllotoxin (PTOX) were established. Enzymological studies revealed highest activities of phenylalanine ammonia-lyase, cinnamyl alcohol dehydrogenase, 4-hydroxycinnamate:CoA ligase and cinnamoyl-CoA:NADP oxidoreductase immediately prior to PTOX accumulation. To investigate PTOX biosynthesis, feeding experiments were performed with [2-(13)C]3',4'-dimethoxycinnamic acid, [2-(13)C]3',4'-methylenedioxycinnamic acid (MDCA), [2-(13)C]3',4',5'-trimethoxycinnamic acid, [2-(13)C]sinapic acid, [2-(13)C]- and [2,3-(13)C(2)]ferulic acid. Analysis of the metabolites by HPLC coupled to tandem mass spectrometry revealed incorporation of label from ferulic acid into PTOX and deoxypodophyllotoxin (DOP). In addition, MDCA was also unambiguously incorporated intact into PTOX. These observations suggest that in L. album both ferulic acid and methylenedioxy-substituted cinnamic acid can be incorporated into lignans. Furthermore, it appears that, in this species, the hydroxylation of DOP is a rate-limiting point in the pathway leading to PTOX. Electronic supplementary material to this paper can be obtained by using the Springer LINK server located at http://dx.doi.org/wo.1007/s00425-002-0834-1.

Topics: Alcohol Oxidoreductases; Aldehyde Oxidoreductases; Carbon Isotopes; Cell Division; Cells, Cultured; Chromatography, High Pressure Liquid; Cinnamates; Coenzyme A Ligases; Coumaric Acids; Drugs, Chinese Herbal; Flax; Hydrogen-Ion Concentration; Lignans; Mass Spectrometry; Molecular Structure; Phenylalanine Ammonia-Lyase; Podophyllotoxin

The dietary origin of lignan phytoestrogens is still poorly understood more than 20 years after their discovery in human urine. Their level in urine has been associated with the consumption of dietary fiber. This paper reports the study of the excretion of enterolactone, assayed by a time-resolved fluoroimmunoassay, in rats fed a diet supplemented with 15% wheat bran, one of the main sources of fiber in Western countries. Enterolactone excretion regularly increased during the two weeks of the diet to reach a value of 45 nmol/day. The level of excretion also increased upon preadaptation to ferulic acid, structurally related to secoisolariciresinol, an established precursor of enterolactone in flaxseeds, and decreased upon preadaptation to potato starch rich in fiber. These results show that the formation of lignans from wheat bran is influenced by the diet, possibly because of an adaptation of the colonic microflora.

Topics: 4-Butyrolactone; Adaptation, Physiological; Animals; Coumaric Acids; Diet; Dietary Fiber; Fluoroimmunoassay; Gas Chromatography-Mass Spectrometry; Lignans; Male; Rats; Rats, Wistar; Solanum tuberosum; Starch

The effects of the phenolic compounds butylated hydroxytoluene (BHT), sesamin (S), curcumin (CU), and ferulic acid (FA) on plasma, liver, and lung concentrations of alpha- and gamma-tocopherols (T), on plasma and liver cholesterol, and on the fatty acid composition of liver lipids were studied in male Sprague-Dawley rats. Test compounds were given to rats ad libitum for 4 wk at 4 g/kg diet, in a diet low but adequate in vitamin E (36 mg/kg of gamma-T and 25 mg/kg of alpha-T) and containing 2 g/kg of cholesterol. BHT significantly reduced feed intake (P < 0.05) and body weight and increased feed conversion ratio; S and BHT caused a significant enlargement of the liver (P < 0.001), whereas CU and FA did not affect any of these parameters. The amount of liver lipids was significantly lowered by BHT (P < 0.01) while the other substances reduced liver lipid concentrations but not significantly. Regarding effects on tocopherol levels, (i) feeding of BHT resulted in a significant elevation (P< 0.001) of alpha-T in plasma, liver, and lung, while gamma-T values remained unchanged; (ii) rats provided with the S diet had substantially higher gamma-T levels (P < 0.001) in plasma, liver, and lung, whereas alpha-T levels were not affected; (iii) administration of CU raised the concentration of alpha-T in the lung (P < 0.01) but did not affect the plasma or liver values of any of the tocopherols; and (iv) FA had no effect on the levels of either homolog in the plasma, liver, or lung. The level of an unknown substance in the liver was significantly reduced by dietary BHT (P < 0.001). BHT was the only compound that tended to increase total cholesterol (TC) in plasma, due to an elevation of cholesterol in the very low density lipoprotein + low density lipoprotein (VLDL + LDL) fraction. S and FA tended to lower plasma total and VLDL + LDL cholesterol concentrations, but the effect for CU was statistically significant (P < 0.05). FA increased plasma high density lipoprotein cholesterol while the other compounds reduced it numerically, but not significantly. BHT, CU, and S reduced cholesterol levels in the liver TC (P < 0.001) and percentages of TC in liver lipids (P < 0.05). With regard to the fatty acid composition of liver lipids, S increased the n-6/n-3 and the 18:3/20:5 polyunsaturated fatty acids (PUFA) ratios, and BHT lowered total monounsaturated fatty acids and increased total PUFA (n-6 + n-3). The effects of CU and FA on fatty acids were not highly significant. Thes

Topics: Animals; Butylated Hydroxytoluene; Cholesterol; Cholesterol, HDL; Cholesterol, LDL; Cholesterol, VLDL; Coumaric Acids; Curcumin; Diet; Dioxoles; Fatty Acids; Lignans; Liver; Lung; Male; Phenols; Rats; Rats, Sprague-Dawley; Vitamin E