trans-Ferulic acid

194.18

194.18

208-679-7

AVM951ZWST

51986|2821

DTXSID5040673

29189900

66.8

1.5

Solid

1.3±0.1 g/cm3

169-170 °C

372.3°C at 760 mmHg

150.5±17.2 °C

1.627

Soluble in alcohol and hot water.

2.69X10-6 mm Hg at 25 deg C (est)

Henry's Law constant = 7.96X10-14 atm-cu m/mol at 25 °C (est)

pKa = 4.42 (hydroxy) (est)|pKa = 4.58

139.8 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|128.8 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|140.1 Ų [M-H]-

Yellow oil. UV max (alcohol): 316 nm /cis-Form/|Orthorhombic needles from water, mp 174 °C. UV max (alcohol): 236, 322 nm. Soluble in hot water, alcohol, ethyl acetate. Moderately soluble in ether. Sparingly soluble in petroleum ether, benzene. Forms a sodium salt. /trans-Form/|Hydroxyl radical reaction rate constant = 4.83X10-11 cu cm/molec-sec at 25 °C (est)

NONH for all modes of transport

3

R36/37/38

S26-S36

UD3365500

Xi:Irritant

Stable. Incompatible with strong oxidizing agents.

P261-P305 + P351 + P338

H315-H319-H335

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 255 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 51 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

SEDIMEMT: Ferulic acid was detected in four out of four sediment samples collected from the Tama River (Japan), Yatsuse River (Japan), Lake Haruma (Japan) and Komgari Reservoir (Japan) on unknown dates at concentrations ranging from 6.5-22 ug/g dry sediment, with an average of 13 ug/g dry sediment(1); the source was likely from the detritus of vascular plants(1).|SOIL: Ferulic acid was detected in one soil sample collected in Tokyo (Japan) between February 1976 and January 1978 at the concentration of 11 ug/g dry soil(1).

URBAN/SUBURBAN: Ferulic acid was detected in five out of eight atmospheric fallout samples collected in Tokyo (Japan) between February 1976 and January 1978 at concentrations ranging from 0.06 and 0.74 ug/sq m-day, with an average of 0.43 ug/sq m-day(1). Ferulic acid was detected in two out of two atmospheric particulate samples collected in Bakersfield (California) and Fresno (California) between December 5, 1995 and January 6, 1996 and at concentrations ranging from 0.3 ng/cu m, with an average of 0.45 ng/cu m(2).|RURAL/REMOTE: Ferulic acid was not detected in one atmospheric particulate sample collected in the Kern Wildlife Refuge (Delano, California) between December 5, 1995 and January 6, 1996(1).

The effects of topically applied curcumin, chlorogenic acid, caffeic acid, and ferulic acid on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced epidermal ornithine decarboxylase activity, epidermal DNA synthesis, and the promotion of skin tumors were evaluated in female CD-1 mice. Topical application of 0.5, 1, 3, or 10 umol of curcumin inhibited by 31, 46, 84, or 98%, respectively, the induction of epidermal ornithine decarboxylase activity by 5 nmol of TPA. In an additional study, the topical application of 10 umol of curcumin, chlorogenic acid, caffeic acid, or ferulic acid inhibited by 91, 25, 42, or 46%, respectively, the induction of ornithine decarboxylase activity by 5 nmol of TPA. The topical application of 10 umol of curcumin together with 2 or 5 nmol of TPA inhibited the TPA-dependent stimulation of the incorporation of [3H]-thymidine into epidermal DNA by 49 or 29%, respectively, whereas lower doses of curcumin had little or no effect. Chlorogenic acid, caffeic acid, and ferulic acid were less effective than curcumin as inhibitors of the TPA-dependent stimulation of DNA synthesis. Topical application of 1, 3, or 10 mumol of curcumin together with 5 nmol of TPA twice weekly for 20 weeks to mice previously initiated with 7,12-dimethylbenz[a]anthracene inhibited the number of TPA-induced tumors per mouse by 39, 77, or 98%, respectively. Similar treatment of mice with 10 mumol of chlorogenic acid, caffeic acid, or ferulic acid together with 5 nmol of TPA inhibited the number of TPA-induced tumors per mouse by 60, 28, or 35%, respectively, and higher doses of the phenolic acids caused a more pronounced inhibition of tumor promotion. The possibility that curcumin could inhibit the action of arachidonic acid was evaluated by studying the effect of curcumin on arachidonic acid-induced edema of mouse ears. The topical application of 3 or 10 umol of curcumin 30 min before the application of 1 umol of arachidonic acid inhibited arachidonic acid-induced edema by 33 or 80%, respectively.|... A series of in vivo experiments/were/ carried out to evaluate the ability of caffeic and ferulic acids to reduce, in healthy human volunteers, UVB-induced skin erythema, monitored by means of reflectance spectrophotometry. Caffeic and ferulic acids, dissolved in saturated aqueous solution pH 7.2, proved to afford a significant protection to the skin against UVB-induced erythema...|A variety of synthetic and dietary polyphenols protect mammalian and bacterial cells from cytotoxicity induced by hydroperoxides, especially hydrogen peroxide (H2O2). Cytotoxicity of H2O2 on Chinese hamster V79 cells was assessed with a colony formation assay. Cytotoxicity and mutagenicity of H2O2 on Salmonella TA104 were assessed with the Ames test. SOS response induced by H2O2 was investigated in the SOS chromotest with Escherichia coli PQ37. The polyphenol-bearing o-dihydroxy (catechol) structure, i.e., nordihydroguaiaretic acid, caffeic acid ester, gallic acid ester, quercetin, and catechin, were effective for suppression of H2O2-induced cytotoxicity in these assay systems. In contrast, neither ferulic acid ester-bearing o-methoxyphenol structure nor alpha-tocopherol were effective, indicating that o-dihydroxy or its equivalent structure in flavonoids is essential for the protection. There are many reports describing that polyphenols act as prooxidants in the presence of metal ions. /These/ results suggest, however, that they act as antioxidants in the cells, when no metal ions are added to the medium.|This review describes the modes of mice radiation injuries induced by soft X-irradiation under various conditions and the protective effects of several kinds of substances on these injuries. The models of radiation injuries in this study were bone marrow death after lethal irradiation, skin damage induced by irradiation with long length soft X-ray and leukocytopenia in the peripheral blood after sublethal irradiation. Two bioassay methods were established for the survival effect on the lethal irradiation and protective potency on the skin damage induced by soft X-irradiation. The protective potencies of various sulfur compounds, related compounds of ferulic acid, nucleic acid constitutional compounds, crude drugs and Chinese traditional medicines were determined and then many effective drugs were recognized. Effective components in the methanol extracts of Cnidii Rhizoma and Aloe arborescens recognized as radioprotectable were fractionated. As a result of these studies, it was observed that the active principles in Cnidii Rhizoma were identified as ferulic acid and adenosine. The scavenger action of active oxygens, a protective effect on the damages of deoxyribonucleic acid and superoxide dismutase by in vitro soft X-irradiation were evaluated as radiation protective mechanisms.|For more Interactions (Complete) data for FERULIC ACID (8 total), please visit the HSDB record page.

Ferulic acid is found in soil humus, and is derived from the breakdown of lignin from wood/plant materials(1). Ferulic acid has been found in atmospheric particulate matter, the source of which is wood combustion(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 57(SRC), determined from a log Kow of 1.51(2) and a regression-derived equation(3), indicates that ferulic acid is expected to have high mobility in soil(SRC). The pKa of ferulic acid is 4.58(4), indicating that this compound will almost entirely exist in the anion form. In the environment, anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of ferulic acid from moist soil surfaces is not expected to be an important fate process(SRC) given the anionic nature of ferulic acid in the environment. Ferulic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7X10-6 mm Hg(SRC), determined from a fragment constant method(6). Under neutral and acidic conditions in soil, ferulic acid is expected to undergo rapid aerobic biodegradation(7)(8). Under alkaline conditions in soil, ferulic acid is not expected to undergo rapid aerobic biodegradation(8).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 57(SRC), determined from a log Kow of 1.51(2) and a regression-derived equation(3), indicates that ferulic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.58(4) indicates ferulic acid will exist almost entirely in the anion form at pH values of 5 to 9, and therefore volatilization from water surfaces/moist soil is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3.2(SRC), from its log Kow of 1.51(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Ferulic acid is expected to biodegrade rapidly in water under anaerobic conditions(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ferulic acid, which has a an estimated vapor pressure of 2.7X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases. Vapor-phase ferulic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 8 hours(SRC), calculated from its rate constant of 4.8X10-11 cu cm/molecule-sec at 25 °C(SRC), derived using a structure estimation method(3). Particulate-phase ferulic acid may be removed from the air by wet or dry deposition(SRC). Ferulic acid contains a chromophore that absorbs light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of ferulic acid with photochemically-produced hydroxyl radicals has been estimated as 4.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 hours at an atmospheric concentration of 5.0X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of ferulic acid with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). The measured rate constant for the reaction of hydroxyl radicals in aqueous solutions of ferulic acid at neutral pH is 1.0X10+10 L/mol-sec(2); this corresponds to an aquatic half-life of about 80 days at an aquatic concentration of 1X10-17 moles hydroxyl radicals per liter(3). Ferulic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Ferulic acid contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3.2 was calculated in fish for ferulic acid, using a measured log Kow of 1.51 (1) and a regression-derived equation (2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organism is low(SRC), provided the compound is not metabolized by the organism(SRC).

The Koc of ferulic acid is estimated as 57(SRC), using a log Kow of 1.51(1)(SRC) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that ferulic acid is expected to have high mobility in soil. The pKa of ferulic acid is 4.58(4), indicating that this compound will almost entirely exist in the anion form in the environment. Anions generally do not adsorb more strongly to soils containing organic carbon and clay, in comparison with their neutral counterparts(5).

Ferulic acid, with a pKa of 4.58(1), will almost entirely exist in the anion form in the environment at pH values of 5 to 9, and therefore ferulic acid is expected to be essentially nonvolatile from water surfaces and moist soil(2). Ferulic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7X10-6 mm Hg(SRC), determined from a fragment constant method(3).

SURFACE WATER: Ferulic acid was detected in two of three surface water samples collected from the Tama River and the Sumida River, Tokyo(Japan) between September 11, 1973 and December 6, 1973 at concentrations ranging from 10-90 ng/L(1). The most likely source of ferulic acid was from the degradation of lignin derived from wood/plant materials.

Occupational exposure to ferulic acid may occur through inhalation and dermal contact with this compound at workplaces where ferulic acid is produced or used. Monitoring data indicate that the general population may have limited exposure to ferulic acid via inhalation of particulates in ambient air, ingestion of surface water, and dermal contact with soil. (SRC)

Ferulic acid (FA) is an effective scavenger of free radicals and it has been approved in certain countries as food additive to prevent lipid peroxidation.|Sodium ferulate (SF) or 3-methoxy-4-hydroxy-cinamate sodium is an active principle from Angelica sinensis, Cimicifuga heracleifolia, Lignsticum chuangxiong, and other plants. It has been used in traditional Chinese medicine and is approved by State Drugs Administration of China as a drug for treatment of cardiovascular and cerebrovascular diseases. SF has antithrombotic, platelet aggregation inhibitory and antioxidant activities in animals and humans. For several decades SF has been widely used in China to treat cardiovascular and cerebrovascular diseases and to prevent thrombosis... /Sodium ferulate/|/EXPL THER/ Ligusticum Chuanxiong and its effective components were studied in the treatment of ischemic stroke, a common emergent disease in China. Some injections of the medicines, including Ligusticum, Ligustrazine, Ligustylid and ferulic acid, were tested clinically and experimentally. The results showed that the effects of the drugs were the same as or even better than those of the controls, such as papaverine, dextran and aspirin-persantin. They could improve brain microcirculation through inhibiting thrombus formation and platelet aggregation as well as blood viscosity.|/EXPL THER/ Although more definitive research is necessary, several natural therapies show promise in treating hot flashes without the risks associated with conventional therapies. Soy and other phytoestrogens, black cohosh, evening primrose oil, vitamin E, the bioflavonoid hesperidin with vitamin C, ferulic acid, acupuncture treatment, and regular aerobic exercise have been shown effective in treating hot flashes in menopausal women.|For more Therapeutic Uses (Complete) data for FERULIC ACID (6 total), please visit the HSDB record page.

Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)|Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)|Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic). (See all compounds classified as Cholagogues and Choleretics.)|Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY. (See all compounds classified as Free Radical Scavengers.)|Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)|Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

The study described here has investigated the bioavailability of ferulic acid in humans, from tomato consumption, through the monitoring of the pharmacokinetics of excretion in relation to intake. The results show that the peak time for maximal urinary excretion is approximately 7 hr and the recovery of ferulic acid in the urine, on the basis of total free ferulic acid and feruloyl glucuronide excreted, is 11-25% of that ingested.|The ... study investigated the urinary excretion of free and conjugated ferulic acid, present in quantitatively detectable amounts in French maritime pine (Pinus maritima) bark extract (PBE), after oral PBE administration to human subjects. Eleven healthy adult subjects (4 women and 7men) consumed either a single dose (200 mg PBE) or two doses of PBE (100 and 200 mg, respectively) within a 48-hr interval. Two days before the oral administration of PBE and during the urine sample collection period volunteers adhered to a diet low in polyphenols. Aliquots of all urine production were collected over 24 hr. Free and conjugated ferulic acid was assessed in urine by HPLC using diode array detection. A close association between the dietary intake of PBE and the urinary excretion of ferulic acid was detected. Moreover, the results indicate that a considerable proportion of ferulic acid is excreted as glucuronide or sulfate after PBE consumption, varying over the range 2 to 20% between individuals. The kinetics of excretion associated with the administration of 100 mg PBE was quite similar to that obtained after 200 mg PBE. A biphasic trend was evident in a number of subjects. All subjects studied here displayed a significant, although variable level of excretion of ferulic acid after supplementation with PBE, Thus, the data provide evidence that at least a part of the phenolic components of PBE are absorbed, metabolized, and eliminated by humans.|The hydroxycinnamates, intermediates in the phenylpropanoid synthetic pathway, are effective in enhancing the resistance of low-density lipoprotein (LDL) to oxidation in the order caffeic acid greater than ferulic acid greater than p-coumaric acid. It is unclear whether the mode of action of ferulic acid as an antioxidant is based on its activities in the aqueous or the lipophilic phase. Partitioning of 14C-labelled ferulic acid into plasma and its components, LDL and the albumin-rich fractions, has been studied under conditions of maximum aqueous solubility. The majority of ferulic acid associates with the albumin-rich fraction of the plasma, although a proportion is also found to partition between the LDL and aqueous phases; however, ferulic acid does not associate with the lipid portion of the LDL particle, suggesting that it exerts its antioxidant properties from the aqueous phase. This is of particular interest since the results demonstrate that ferulic acid is a more effective antioxidant against LDL oxidation than the hydrophilic antioxidant ascorbic acid.|The major constituents of artichoke extracts are hydroxycinnamic acids such as chlorogenic acid, dicaffeoylquinic acids caffeic acid and ferulic acid, and flavonoids such as luteolin and apigenin glycosides. ...Several studies have shown the effect on animal models of artichoke extracts ... . . Results showed a plasma maximum concentration of 6.4 (SD 1.8) ng/mL for chlorogenic acid after 1 hr and its disappearance within 2 hr (P< 0.05). Peak plasma concentrations of 19.5 (SD 6.9) ng/ml for total caffeic acid were reached within 1 h, while ferulic acid plasma concentrations showed a biphasic profile with 6.4 (SD1.5) ng/mL and 8.4 (SD4.6) ng/mL within 1 hr and after 8 hr respectively. ...A significant increase of dihydrocaffeic acid and dihydroferulic acid total levels after 8 hr (P<0.05) /was observed/. No circulating plasma levels of luteolin and apigenin were present.

The bioavailability of ferulic acid (FA; 3-methoxy-4-hydroxycinnamic acid) and its metabolites was investigated in rat plasma and urine after an oral short-term ingestion of 5.15 mg/kg of FA. Free FA, glucuronoconjugates, and sulfoconjugates were quickly detected in plasma with a peak of concentration found 30 min after ingestion. Sulfoconjugates were the main derivates ( approximately 50%). In urine, the cumulative excretion of total metabolites reached a plateau 1.5 h after ingestion, and approximately 40% were excreted by this way. Free FA recovered in urine represented only 4.9 +/-1.5% of the native FA consumed by rats. Glucuronoconjugates and sulfoconjugates represented 0.5 +/- 0.3 and 32.7 +/- 7.3%, respectively. These results suggested that a part of FA incorporated in the diet was quickly absorbed and largely metabolized in sulfoconjugates before excretion in urine.|Ferulic acid (FA) is a phytochemical commonly found in fruits and vegetables such as tomatoes, sweet corn and rice bran. It arises from metabolism of phenylalanine and tyrosine by Shikimate pathway in plants.|Ferulic Acid has known human metabolites that include (2S,3S,4S,5R)-6-[4-[(E)-2-carboxyethenyl]-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ The aim of this study is to investigate the effects of ferulic acid (FA) on human sperm motility, viability, lipid peroxidation, and cyclic nucleotides in fertile and asthenozoospermic infertile individuals in vitro. The sperm samples were obtained from 10 fertile volunteers and 10 asthenozoospermic infertile patients. Washed spermatozoa were incubated at 37 degrees C in Ham's F-10 medium with 0, 0.1, 0.2, 0.4, 0.8, or 1.6 mM of FA. Samples were analyzed for viability, determined by eosin-Y dye exclusion method at 0, 1, 2, 3, 5, and 6 hr of incubation; motility, determined by the trans-membrane migration method within 2 hr of incubation; LPO, determined by thiobarbituric acid (TBA) method at 3 hr of incubation and the intracellular cAMP and cGMP, determined, respectively, by 3H-cAMP and 125I-cGMP radioimmunoassay at 3 hr of incubation. The results showed: in both fertile and infertile spermatozoa, the viability, trans-membrane migration ratio (TMMR) and the levels of intracellular cAMP and cGMP in FA-treated spermatozoa were significantly higher than those of spermatozoa in control groups, while TBA-reactive substances contents in treated spermatozoa were significantly lower than those in control spermatozoa. The effects of FA on these processes were concentration dependent. These data suggested that FA is beneficial to sperm viability and motility in both fertile and infertile individuals, and that reduction of lipid peroxidative damage to sperm membranes and increase of intracellular cAMP and cGMP may be involved in these benefits.|/GENOTOXICITY/ In the present study, the effects of extracts and polyphenol-rich fractions as well as monomer polyphenols identified in them, from both red and white grapes, on mitomycin C (MMC) induced sister chromatid exchanges (SCEs) in human peripheral blood lymphocytes were investigated. The grape extracts and two of the three polyphenol-rich fractions promoted MMC-induced SCEs at concentrations from 75 to 300 ug/mL. However, none of the extracts or fractions alone induced SCEs. Thus, these results suggest caution especially with regard to the use of grape extracts as dietary supplements. On the other hand, the fact that these extracts were not genotoxic alone may indicate a selective activity against genetically damaged cells. This is the first study regarding the clastogenic effects of grape extracts in human cells. Moreover, from the tested polyphenols, caffeic acid, gallic acid, and rutin hydrate enhanced MMC-induced clastogenicity, whereas ferulic acid, protocatechuic acid, (+)-catechin, (-)-epicatechin, and trans-resveratrol had no effect at concentrations between 5 and 100 uM. The differences in the chemical structures of the tested polyphenols may account for their differential effects on MMC clastogenicity.|/ALTERNATIVE and IN VITRO TESTS/ ... The effects of more physiological concentrations (0.1 um) of various individual polyphenols on gene expression were ... investigated in cultured human umbilical vein endothelial cells (HUVEC) using both microarray and quantitative RT-PCR methodologies. Treatment of HUVEC with ferulic acid, quercetin or resveratrol (0.1 um) resulted in changes to gene expression that for the three treatments amounted to significant (>2-fold) down-regulation of the expression of 363 genes and significant (>2-fold) up-regulation of 233 genes of the 10,000 genes present on the microarray. The majority of these genes were affected by resveratrol. Quantitative RT-PCR studies indicated that resveratrol (0.1 um) significantly increased the expression of the gene encoding endothelial NO synthase (eNOS), which synthesizes the vasodilator molecule NO, and both resveratrol and quercetin decreased expression of the potent vasoconstrictor, endothelin-1 (ET-1), while ferulic acid had no effect...|/ALTERNATIVE and IN VITRO TESTS/ The possible effects of naturally occurring plant phenolics, caffeic acid (CA), chlorogenic acid (CGA) and ferulic acid (FA) on arylamine N-acetyltransferase (NAT) activities on human gastrointestinal microflora, Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes, Citrobacter koseri and Pseudomonas aeruginosa, were examined. The bacterial NAT activities were determined by HPLC measuring the acetylation of 2-aminofluorene (2-AF). Among all examined bacteria, P. aeruginosa exerted the highest NAT activity while C. koseri possessed the lowest NAT activity. CA, CGA and FA could suppress the bacterial NAT activities dose-dependently both in the intact cell and cytosolic fraction analysis. According to the analysis of kinetic parameters in E. coli and P. aeruginosa, CA, CGA and FA were shown to be potent noncompetitive inhibitors of bacterial NAT activities. For the time course experiment, 4 mM of CA and FA could inhibit bacterial NAT activities for at least 4 hour but 4 mM of CGA could only significantly suppress NAT activity in E. coli for the same reaction time. These results strongly demonstrated that CA, CGA and FA inhibited NAT activities in human gastrointestinal bacteria.

3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid

2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-: ACTIVE|Ferulic acid is an extremely abundant, preformed phenolic aromatic chemical found widely in nature. Ferulic acid is viewed as a commodity scale, renewable chemical feedstock for biocatalytic conversion to other useful aromatic chemicals. Most attention is focused on bioconversions of ferulic acid itself. Topics covered include cinnamoyl side-chain cleavage; nonoxidative decarboxylation; mechanistic details of styrene formation; purification and characterization of ferulic acid decarboxylase; conversion of ferulic acid to vanillin; O-demethylation; and reduction reactions.

A high-performance liquid chromatographic method was developed for selective determination of ferulic acid in 7 min in the extracts from wheat flour and ground whole wheat at typical levels of 50 and 500 micrograms/g, respectively. Recovery of 99.9% was obtained when ferulic acid was extracted into dilute sulfuric acid, followed by enzymatic treatment of the extract with an alpha-amylase preparation. The chromatographic system included a 100-mm column packed with Hypersil 5 micron reversed-phase ODS operating isocratically with 12% methanol-citrate buffer (pH 5.4) mixture. The selectivity and sensitivity of both ultraviolet diode array and fluorescence detectors was investigated. The optimum wavelengths selected were 320 nm and 312 nm/418 nm respectively. Relative standard deviations of the analytical procedure were 2.43% and 5.10% for whole wheat and flour samples, respectively.

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