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1.
Ferulic acid is a phenolic compound that serves as a major biosynthetic precursor of vanillin in higher plants. We investigated the ability of the 3 commercial enzymes—Ultraflo L, Viscozyme L, and α-Amylase—to induce the release ferulic acid from theIpomoea batatas L. (sweet potato) stem. The rate of release for ferulic acid was optimal when Ultraflo L (1.0%) was used compared with the other enzymes, whereas Viscozyme L was most effective for the release of vanillic acid and vanillin. Thus, these enzymes may be useful for the large-scale production of ferulic acid and other phenolic compounds from sweet potato stem.  相似文献   

2.
p-Coumaric acid (4-hydroxycinnamic acid) and ferulic acid (4-hydroxy-3-methoxycinnamic acid) have been identified as constituents of cutin. Their reduction products were isolated from a phenolic fraction released from the cutin of the fruits of apple, peach, pear, and two varieties of tomato and apple leaf by treatment with LiAlH(4) or LiAlD(4). They were identified by combined gas chromatography and mass spectrometry. p-Coumaric acid was present in all samples of cutin (0.07-0.53% by weight), whereas only peach and pear cutin contained measurable amounts of ferulic acid (0.007% and 0.035%, respectively). Both p-coumaric acid and ferulic acid were identified to be constituents of the insoluble material recovered after partial hydrolysis (12-42% loss) of cutin in 1 m NaOH at 80 C. A significant part (48%) of the p-coumaric acid contained in tomato cutin was contained in the insoluble material recovered after partial degradation (7.4%) of this cutin with 0.01 m NaOH. These data indicate that these phenolic components are tightly (possibly covalently) bound to cutin. Similar analysis of the phenolic fractions from the suberins of potato, sweet potato, turnip, rutabaga, carrot, and red beet revealed that they contained only ferulic acid (0.05-0.22%). Ferulic acid was identified as a constituent of the insoluble material recovered after partial hydrolysis of potato and beet suberins (34% and 32% loss, respectively) in 1 m NaOH at 80 C. A major part (65%) of the ferulic acid contained in potato suberin was contained in the insoluble material recovered after partial (26.8% loss) degradation of this suberin with 0.01 m NaOH. Ferulic acid appears to be tightly (probably covalently) bound to suberin.  相似文献   

3.
This study aimed to determine the phenolic compounds profile, antioxidant potential and cytotoxicity of extracts and fractions of Caesalpinia palmeri. Methanolic extracts were generated from C. palmeri berries, stems and flowers. The latter was subjected to liquid-liquid partition, obtaining hexane, ethyl acetate and residues fractions. Results showed that the flower extract and ethyl acetate fraction had a larger concentration of phenolic compounds (148.9 and 307.9 mg GAE/g, respectively), being ellagic acid (6233.57 and 19550.08 μg/g, respectively), quercetin-3-β-glycoside (3023.85 and 8952.55 μg/g, respectively) and gallic acid (2212.98 and 8422.34 μg/g, respectively) the most abundant compounds. Flower extract and ethyl acetate fraction also presented the highest antioxidant capacity on all tested methods (DPPH, ABTS, ORAC and FRAP) and low cytotoxicity against ARPE-19 cells (IC50 >170 μg/mL). C. palmeri possessed high antioxidant potential, associated with the presence of phenolic compounds and low cytotoxicity, suggesting that they could represent an option to counter oxidative stress.  相似文献   

4.
通过室内培养法,研究了不同浓度的阿魏酸、对羟基苯甲酸及其混合液对土壤氮素、与氮素转化相关的微生物和酶的影响。结果表明,10-4mol/L阿魏酸和对羟基苯甲酸使土壤铵态氮降低了11.18%和10.87%,硝态氮降低了6.33%和3.95%;10-3mol/L阿魏酸、对羟基苯甲酸及其混合液分别使可溶性有机氮降低了6.59%、10.16%和10.39%。阿魏酸、对羟基苯甲酸及其混合液抑制了氨化细菌、硝化细菌和反硝化细菌的生长,削弱了土壤脲酶与蛋白酶的活性。与对照相比,10-4mol/L混合液降低了26.04%的氨化细菌、30.79%的硝化细菌和16.74%的反硝化细菌。10-3mol/L阿魏酸减少了3.33%的土壤脲酶和20.87%的蛋白酶活性;10-3mol/L对羟基苯甲酸降低了土壤脲酶6.63%,蛋白酶22.94%;10-3mol/L混合液减少了土壤脲酶7.47%和蛋白酶23.79%。混合液对土壤氮素转化的抑制作用最强,表明阿魏酸和对羟基苯甲酸存在协同作用。阿魏酸和对羟基苯甲酸等酚酸类化合物通过抑制土壤氮素转化微生物及其酶活性,从而影响土壤氮素转化。  相似文献   

5.
Naoto Shibuya 《Phytochemistry》1984,23(10):2233-2237
Ferulic acid, p-coumaric acid and diferulic acid were detected in the alkaline extract of rice endosperm cell walls. The amount of each component was estimated as 9.1, 2.5 and 0.56 mg/g cell wall, respectively. Several phenolic-carbohydrate esters were isolated from the enzymatic digest of this cell wall, which included a series of ferulic acid esters of arabinoxylan fragments and also some fractions containing a high proportion of diferulic acid.  相似文献   

6.
Major cell wall-bound phenolic compounds were detected and identified in roots of tomato at different stages of growth. Alkaline hydrolysis of the cell wall material of the root tissues yielded ferulic acid as the major bulk of the phenolic compounds. Other phenolic compounds identified were 4-hydroxybenzoic acid, vanillic acid, 4-hydroxybenzaldehyde, vanillin and 4-coumaric acid. All the six phenolic acids were higher in very early stage of plant growth. Ferulic acid, 4-hydroxybenzoic acid and 4-coumaric acid exhibited a decreasing trend up to 60 days and then the content of these phenolic acids increased somewhat steadily towards the later stage of growth. Total phenolics, phenylalanine ammonia-lyase (PAL) activity and peroxidase (POD) activity were in tandem match with the occurrence pattern of the phenolic acids. Ferulic acid showed highest antifungal activity against tomato wilt pathogen Fusarium oxysporum f. sp. lycopersici. The results of this study may be interpreted to seek an explanation for high susceptibility of tomato plants at flowering stage to Fusarium wilt. It may also be concluded that greater amounts of ferulic acid in combination with other phenolics and higher level of PAL and POD activities after 60 days of growth may have a role in imparting resistance against Fusarium wilt at a late stage of plant growth.  相似文献   

7.
Microbial transformation of ferulic acid to acetovanillone was studied using growing cells of Rhizopus oryzae. Ferulic acid was added to the growing medium (0.5 g L?1) and incubated for 12 days. The progress of formation of metabolites was monitored by GC and GC-MS after extraction with ethyl acetate. The major metabolite was acetovanillone with minor metabolites formed, such as dihydroferulic acid, coniferyl alcohol and dihydroconiferyl alcohol. Traces of metabolites (≤1–3%), such as vanillin, vanillyl alcohol, vanillic acid and phenyl ethyl alcohol, were also produced. Formation of 4-vinyl guaiacol increased from day 1 (12.4%), reaching a maximum on day 4 (31.7%), and reducing to a minimum on day 12 (3.1%). The formation of acetovanillone increased only from day 2 onward, and reached a maximum (49.2%) on day 12. The optimum concentration of ferulic acid to be added into the medium was found to be only 0.5 g L?1, as any increase in concentration (0.75 and 1.0 g L?1) precipitated the precursor, resulting in no further degradation.  相似文献   

8.
Microbial transformation of ferulic acid to acetovanillone was studied using growing cells of Rhizopus oryzae. Ferulic acid was added to the growing medium (0.5 g L-1) and incubated for 12 days. The progress of formation of metabolites was monitored by GC and GC-MS after extraction with ethyl acetate. The major metabolite was acetovanillone with minor metabolites formed, such as dihydroferulic acid, coniferyl alcohol and dihydroconiferyl alcohol. Traces of metabolites (≤1-3%), such as vanillin, vanillyl alcohol, vanillic acid and phenyl ethyl alcohol, were also produced. Formation of 4-vinyl guaiacol increased from day 1 (12.4%), reaching a maximum on day 4 (31.7%), and reducing to a minimum on day 12 (3.1%). The formation of acetovanillone increased only from day 2 onward, and reached a maximum (49.2%) on day 12. The optimum concentration of ferulic acid to be added into the medium was found to be only 0.5 g L-1, as any increase in concentration (0.75 and 1.0 g L-1) precipitated the precursor, resulting in no further degradation.  相似文献   

9.
Arum elongatum (Araceae) is widely used traditionally for the treatment of abdominal pain, arterial hypertension, diabetes mellitus, rheumatism and hemorrhoids. This study investigated the antioxidant properties, individual phenolic compounds, total phenolic and total flavonoid contents (HPLC/MS analysis), reducing power and metal chelating effects of four extracts obtained from A. elongatum (ethyl acetate (EA), methanol (MeOH), methanol/water (MeOH/water) and infusion). The inhibitory activity of the extracts were also determined against acetylcholinesterase, butyrylcholinesterase, tyrosinase, amylase and glucosidase enzymes. The MeOH/water extracts contained the highest amount of phenolic contents (28.85 mg GAE/g) while the highest total flavonoid content was obtained with MeOH extract (36.77 mg RE/g). MeOH/water demonstrated highest antioxidant activity against DPPH⋅ radical at 38.90 mg Trolox equivalent per gram. The infusion extract was the most active against ABTS+⋅ (133.08 mg TE/g). MeOH/water extract showed the highest reducing abilities with the CUPRAC value of 102.22 mg TE/g and the FRAP value of 68.50 mg TE/g. A strong metal chelating effect was observed with MeOH/water extract (35.72 mg EDTAE/g). The PBD values of the extracts ranged from 1.01 to 2.17 mmol TE/g. EA extract displayed the highest inhibitory activity against AChE (2.32 mg GALAE/g), BChE (3.80 mg GALAE/g), α-amylase (0.56 mmol ACAE/g) and α-glucosidase (9.16 mmol ACAE/g) enzymes. Infusion extract was the most active against tyrosinase enzyme with a value of 83.33 mg KAE/g. A total of 28 compounds were identified from the different extracts. The compounds present in the highest concentration were chlorogenic acids, 4-hydroxybenzoic acid, caffeic acid, p-coumaric acid, ferulic acid, isoquercitrin, delphindin 3,5-diglucoside, kaempferol-3-glucoside and hyperoside. The biological activities of A. elongatum extracts could be due to the presence of compounds such as gallic acid, chlorogenic acids, ellagic acid, epicatechin, catechin, kaempferol, 4-hydroxybenzoic acid, caffeic acid, p-coumaric acid, ferulic acid, quercetin, isoquercitrin, and hyperoside. Extracts of A. elongatum showed promising biological activities which warrants further investigations in an endeavor to develop biopharmaceuticals.  相似文献   

10.
High performance liquid chromatography analysis of different parts of Sclerotium rolfsii-infected and healthy seedlings of chickpea (Cicer arietinum) was carried out to examine the status of phenolic compounds. Three major peaks that appeared consistently were identified as gallic, vanillic and ferulic acids. Gallic acid concentrations were increased in the leaves and stems of infected plants compared to healthy ones. Vanillic acid detected in stems and leaves of healthy seedlings was not detected in infected seedlings. There was a significant increase of ferulic acid in those stem portions located above the infected collar region compared to minimal amounts in the roots of healthy seedlings. In vitro studies of ferulic acid showed significant antifungal activity against S. rolfsii. Complete inhibition of mycelial growth was observed with 1000 g of ferulic acid/ml. Lower concentrations (250, 500 and 750 g/ml) were also inhibitory and colony growth was compact in comparison with the fluffy growth of normal mycelium. Higher amounts of phenolics were found in the stems and leaves of S. rolfsii-infected seedlings in comparison to the healthy ones. A role for ferulic acid in preventing infections by S. rolfsii in the stems and leaves of chickpea plants above the infection zone is therefore feasible.  相似文献   

11.
Three ferulic acid esterases from the filamentous fungus Chrysosporium lucknowense C1 were purified and characterized. The enzymes were most active at neutral pH and temperatures up to 45 °C. All enzymes released ferulic acid and p-coumaric acid from a soluble corn fibre fraction. Ferulic acid esterases FaeA1 and FaeA2 could also release complex dehydrodiferulic acids and dehydrotriferulic acids from corn fibre oligomers, but released only 20% of all ferulic acid present in sugar beet pectin oligomers. Ferulic acid esterase FaeB2 released almost no complex ferulic acid oligomers from corn fibre oligomers, but 60% of all ferulic acid from sugar beet pectin oligomers. The ferulic acid esterases were classified based on both, sequence similarity and their activities toward synthetic substrates. The type A ferulic acid esterases FaeA1 and FaeA2 are the first members of the phylogenetic subfamily 5 to be biochemically characterized. Type B ferulic acid esterase FaeB2 is a member of subfamily 6.  相似文献   

12.
Ferulic acid was efficiently released from a wheat bran preparation by a ferulic acid esterase from Aspergillus niger (FAE-III) when incubated together with a Trichoderma viride xylanase (a maximum of 95% total ferulic acid released after 5 h incubation). FAE-III by itself could release ferulic acid but at a level almost 24-fold lower than that obtained in the presence of the xylanase (2 U). Release of ferulic acid was proportional to the FAE-III concentration between 0.1 U and 1.3 U, but the presence of low levels of xylanase (0.1 U) increased the amount of ferulic acid released 6-fold. Total sugar release was not influenced by the action of FAE-III on the wheat bran, but the rate of release of the apparent end-products of xylanase action (xylose and xylobiose) was elevated by the presence of the esterase. The results show that FAE-III and the xylanase act together to break down feruloylated plant cell-wall polysaccharides to give a high yield of ferulic acid.  相似文献   

13.
In this review we examine the fascinating array of microbial and enzymatic transformations of ferulic acid. 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. Biotransformations of vinylgualacol are discussed, and selected biotransformations of vanillic acid including oxidative and nonoxidative decarboxylation are surveyed. Finally, enzymatic oxidative dimerization and polymerization reactions are reviewed.  相似文献   

14.
During the last decades, different natural compounds have been demonstrated to modulate inflammatory pathways. In this study, methanolic extract of Echinophora tenuifolia L. inflorescences was investigated for its chemical composition and in vitro antioxidant and anti-inflammatory properties. Phytochemical profile was investigated by means of high-performance thin layer chromatography (HPTLC) and gas chromatography–mass spectrometry analyses. Myristic acid and palmitic acid were found to be the major constituents. Six terpenes were identified: α-phellandrene, o-cymene, dihydroactinidiolide, neophytadiene, phytol and β-amyrin, and two phenolic compounds: carvacrol and ferulic acid. HPTLC analysis of the ethyl acetate fraction highlighted the presence of the flavonoid glycosides rutin and quercitrin. This sample showed the best diphenylpicrylhydrazyl scavenging capacity, with an IC50 value equal to 40.39 μg/ml, and the strongest capacity to protect linoleic acid from peroxidation, as assessed by the β-carotene bleaching test (IC50 = 16.31 μg/ml). All samples inhibited nitric oxide production in cell supernatants in a dose-dependent manner, being the two apolar fractions (n-hexane and dichloromethane) even more active than the positive control indomethacin. A relevant biological activity was observed for dichloromethane fraction (IC50 value equal to 39.97 μg/ml). Obtained results indicate that this sample could be an excellent candidate for further investigations aimed at the development of new antioxidant and anti-inflammatory drugs.  相似文献   

15.
Some or possibly all Ti plasmids of Agrobacterium tumefaciens encode a bicistronic operon designated virH, which encodes two proteins, VirH1 and VirH2, that resemble a family of cytochrome P450-type monooxygenases. Expression of this operon is induced by a family of phenolic compounds that induce all other operons within the vir regulon. We hypothesized that either or both of these proteins might metabolize some or all of these phenolic compounds. We therefore tested induction of a vir promoter by a variety of phenolic compounds in isogenic strains that express or lack virH1 and virH2. Although some compounds were equally effective inducers regardless of the virH status, other compounds induced vir expression far more effectively in the virH mutant than in the virH-proficient host. For all tested compounds, VirH2 appeared to be solely responsible for this effect. One such compound, ferulic acid, was chosen for biochemical analysis. Ferulic acid was degraded by a VirH-proficient host but not by a VirH mutant. The wild-type strain released large amounts of a more hydrophilic compound into the cell supernatant. This compound was tested by mass spectroscopy, nuclear magnetic resonance and UV spectroscopy and found to consist of caffeic acid. This indicates that wild-type strains convert virtually all added ferulic acid to caffeic acid, and that VirH2 is essential for this O-demethylation reaction. Ferulic acid was far more toxic than caffeic acid to the wild-type strain, although the wild-type strain was more resistant to ferulic acid than was the virH mutant. Caffeic acid was slowly removed from the broth, suggesting further metabolic reactions.  相似文献   

16.
Fraxinus xanthoxyloides is a perennial shrub belonging to family Oleaceae, traditionally used for malaria, jaundice, pneumonia, inflammation, and rheumatism. Our study is aimed to assess the total phenolics (TPC), flavonoids (TFC), terpenoids contents (TTC) and antioxidant profiling of F. xanthoxyloides methanol bark extract (FXBM) and its fractions, hexane, chloroform, ethyl acetate and aqueous, along with high-performance liquid chromatography with diode-array detection (HPLC-DAD). Further, the antioxidant and pulmonary protective potential was explored against carbon tetrachloride (CCl4)-induced CCl4-induced pulmonary tissue damage in rats. The highest TPC, TFC and TTC were found in FXBM (133.29±4.19 mg/g), ethyl acetate fraction (279.55±10.35 mg/g), and chloroform fraction (0.79±0.06 mg/g), respectively. The most potent antioxidant capacity was depicted by FXBM (29.21±2.40 μg/mg) and ethyl acetate fraction (91.16±5.51 μg/mg). The HPLC-DAD analysis revealed the predominance of gallic, chlorogenic, vanillic and ferulic acid in FXBM. The administration of CCl4 induced oxidative stress, suppressed antioxidant enzymes′ activities including catalase, peroxidase, superoxide dismutase, glutathione peroxidase, glutathione-S-transferase, and glutathione reductase. Further, it increased thiobarbituric acid reactive substances (TBARS) and H2O2 levels, induced DNA injuries and reduced the total protein and glutathione content in lung tissues. The treatment of rats with FXBM restored these biochemical parameters to the normal level. Moreover, the histopathological studies of lung tissues demonstrated that FXBM protected rats′ lung tissues from oxidative damage restoring normal lung functions. Thus, F. xanthoxyloides bark extract is recommended as adjuvant therapy as protective agent for patients with lung disorders.  相似文献   

17.
A protoplast-to-plant regeneration system has been established for sweet potato (Ipomoea batatas (L.) Lam.) and its wild relative, I. lacunosa L. Viable protoplasts, isolated from preplasmolyzed stems and petioles of in vitro-grown plants, were cultured on liquid MS (Murashige & Skoog 1962) medium that supported cell division and colony formation. Embryogenic calli of sweet potato were induced on agar-solidified MS medium supplemented with 3% (w/v) sucrose, 50 mg l-1 casamino acids, 0.2–0.5 mg l-1 2,4-d, 1.0 mg l-1 kinetin and 1.0 mg l-1 ABA. On average, 3 plants were regenerated from a single sweet potato callus subcultured on semi-solid MS medium containing 3% (w/v) sucrose, 800 mg l-1 glutamine, 2.0 mg l-1 BA or 1.0 mg l-1 kinetin and 1.0 mg l-1 GA3. Embryogenic calli of I. lacunosa L. were initiated on semi-solid MS medium containing 0.2–0.5 mg l-1 IAA and 1.0–2.0 mg l-1 BA. An average of 5 plants was regenerated from a single sweet potato callus subcultured on semi-solid MS medium containing 0.5 or 1.0 mg l-1 GA3.Abbreviations ABA abscisic acid - BA benzyladenine - 2,4-d 2,4-dichlorophenoxyacetic acid - GA3 gibberellic acid - IAA indole acetic acid - MES 2-(N-morpholino)-ethane sulfonic acid - NAA -naphthaleneacetic acid  相似文献   

18.
The root extract of Nauclea xanthoxylon (A.Chev.) Aubrév. displayed significant 50 % inhibition concentration (IC50s) of 0.57 and 1.26 μg/mL against chloroquine resistant and sensitive Plasmodium falciparum (Pf) Dd2 and 3D7 strains, respectively. Bio-guided fractionation led to an ethyl acetate fraction with IC50s of 2.68 and 1.85 μg/mL and subsequently, to the new quinovic acid saponin named xanthoxyloside ( 1 ) with IC50s of 0.33 and 1.30 μM, respectively against the tested strains. Further compounds obtained from ethyl acetate and hexane fractions were the known clethric acid ( 2 ), ursolic acid ( 3 ), quafrinoic acid ( 4 ), quinovic acid ( 5 ), quinovic acid 3-O-β-D-fucopyranoside ( 6 ), oleanolic acid ( 7 ), oleanolic acid 3-acetate ( 8 ), friedelin ( 9 ), β-sitosterol ( 10a ), stigmasterol ( 10b ) and stigmasterol 3-O-β-D-glucopyranoside ( 11 ). Their structures were characterised with the aid of comprehensive spectroscopic methods (1 and 2D NMR, Mass). Bio-assays were performed using nucleic acid gel stain (SYBR green I)-based fluorescence assay with chloroquine as reference. Extracts and compounds exhibited good selectivity indices (SIs) of >10. Significant antiplasmodial activities measured for the crude extract, the ethyl acetate fraction and xanthoxyloside ( 1 ) from that fraction can justify the use of the root of N. xanthoxylon in ethnomedicine to treat malaria.  相似文献   

19.
Introduction – Salicis Cortex, made from willow bark is a herbal remedy, which is standardised based on the content of salicin, a compound with analgesic and antiphlogistic properties. However, clinical trials suggest that other compounds also present in Salicis Cortex can contribute to the pharmacological effects. Objective – To characterise the composition of phenolic acids in the barks of different species and clones from the genus Salix by use of chromatographic methods—HPTLC and HPLC. Methodology – The phenolic acid composition was analysed by MGD (multiple gradient development)–HPTLC technique. The separation was performed on HPTLC Diol plates with gradient elution using a mixture of chloroform:hexane:ethyl acetate with increasing concentration of ethyl acetate from 10 to 25%. Derivatisation with thymol reagent was employed for the first time for specific detection of phenolic acids containing methoxyl groups. Results – The presence of all phenolic acids previously reported in the genus Salix was confirmed, namely p‐hydroxybenzoic, vanillic, cinnamic, p‐coumaric, ferulic and caffeic acids. Furthermore, pyrocatechol as a constituent of willow bark was revealed. The highest concentration of this compound was observed in the S. purpurea bark (2.25 mg/g). Conclusion – The presence of a relatively high content of pyrocatechol in Salix species may raise doubts about the safe application of this herbal medicine. Copyright © 2010 John Wiley & Sons, Ltd.  相似文献   

20.
Our previous study (Biosci. Biotechnol. Biochem., 66, 2449-2457 (2002)), suggested that ferulic acid was transported via a monocarboxylic acid transporter (MCT). Transepithelial transport of ferulic acid was examined in this study by directly measuring the rate of its transport across Caco-2 cell monolayers. Ferulic acid transport was dependent on pH, and in a vectorical way in the apical-basolateral direction. The permeation of ferulic acid was concentration-dependent and saturable; the Michaelis constant was 16.2 mM and the maximum velocity was 220.4 nmol min-1 (mg protein)-1. Various substrates for MCTs, such as benzoic acid and acetic acid, strongly inhibited the permeation of ferulic acid, demonstrating that ferulic acid is obviously transported by MCT. Antioxidative phenolic acid compounds from dietary sources like ferulic acid would be recognized and transported by MCT by intestinal absorption.  相似文献   

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