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1.
Qi M Wang P Selinger LB Yanke LJ Forster RJ McAllister TA 《Journal of applied microbiology》2011,110(5):1341-1350
Aims: A novel ferulic acid esterase gene from rumen fungus Anaeromyces mucronatus was cloned, heteroexpressed in Escherichia coli and characterized. Methods and Results: A total of 30 clones exhibiting activity on α‐naphthyl acetate (α‐NA) were isolated from an A. mucronatus YE505 cDNA library. Sequence analysis revealed that these clones represented two esterase‐coding sequences. The gene, fae1A, showed highest amino acid sequence identity to CE family 1 esterases from anaerobic micro‐organisms such as Orpinomyces sp., Ruminococcus albus and Clostridium thermocellum. The gene comprised 828 nucleotides encoding a polypeptide of 275 amino acids. The coding sequence was cloned into the pET30a expression vector and overexpressed in E. coli BL21 (DE3). Gene product Fae1A was found to exhibit activity against a number of substrates including naphthyl fatty acid esters, p‐nitrophenyl fatty acid esters and hydroxylcinnamic acid esters. Conclusions: Fae1A exhibited a lower Km and higher catalytic efficiency (kcat/Km) on ferulic acid esters than on α‐NA or p‐nitrophenyl acetate, suggesting that it has a higher affinity for ethyl and methyl ferulate than for the acetyl esters. It releases ferulic acid and p‐coumaric acid from barley straw. Activity of Fae1A was inhibited by the serine‐specific protease inhibitor, phenylmethylsulfonyl fluoride, indicating that a serine residue plays a role in its activity. Significance and Impact of the Study: To our knowledge, this is the first report of characterization of carbohydrate esterase gene from the genus of Anaeromyces. 相似文献
2.
41% of the cell walls from mature leaf blades of Lolium multiflorum were digested by treatment during 14 days with C1 enzyme (cellulase) which had been purified by gel filtration and ion-exchange chromatography. Cellobiose was the main sugar released from the walls, together with some glucose and higher oligosaccharides. Considerable amounts of carbohydrate esters of ferulic and p-coumaric acids were also released. When the C1 enzyme was further purified by isoelectric focusing, only 8% of the cell walls were digested. Purified Cx (CM-cellulase) containing β-glucosidase digested 51% of the cell walls in 16 hours: the major component detected in the soluble products was glucose together with some β (1 → 4)-xylobiose, xylose and arabinose. Higher oligosaccharides and carbohydrate esters of ferulic and p-coumaric acids were also present. It was shown that these acids were present in the cell walls mainly in the trans-configuration. 相似文献
3.
Cione E Tucci P Senatore V Perri M Trombino S Iemma F Picci N Genchi G 《Journal of bioenergetics and biomembranes》2008,40(1):19-26
Ferulic acid plays a chemopreventive role in cancer by inducing tumor cells apoptosis. As mitochondria play a key role in
the induction of apoptosis in many cells types, here we investigate the mitochondrial permeability transition (MPT) and the
release of cytochrome c induced by ferulic acid and its esters in rat testes mitochondria, in TM-3 and MLTC-1 cells. While ferulic acid, but not
its esters, induced MPT and cytochrome c release in rat testes isolated mitochondria, in TM-3 cells we found that both ferulic acid and its esters induced cytochrome
c release from mitochondria in a dose-dependent manner, suggesting a potential target of these compounds in the induction of
cell apoptosis. The apoptosis induced by ferulic acid is therefore associated with the mitochondrial pathway involving cytochrome
c release and caspase-3 activation.
Cione and Tucci have equally contributed to this article. 相似文献
4.
Kabel MA Yeoman CJ Han Y Dodd D Abbas CA de Bont JA Morrison M Cann IK Mackie RI 《Applied and environmental microbiology》2011,77(16):5671-5681
5.
《Phytochemistry》1987,26(3):749-752
The esters of n-fatty acids and ω-hydroxy n-fatty acids of β-sitosterol, D-glucose and ferulic acid (trans and cis) as well as β-sitosterol, fatty acids and β-sitosteryl-β-D-glucoside were isolated from three Virola species and identified by optical data and chemical reactions. A novel series of acidic esters derived from C22C29 ω-hydroxy fatty acids and cis- and trans-ferulic acid is reported for the first time. These compounds also occurred as the corresponding diester 1-monoglycerides whereas the ω-hydroxy acids themselves were also present as the corresponding glucosyl esters. 相似文献
6.
《Enzyme and microbial technology》2005,36(5-6):729-736
A feruloyl esterase (StFaeC) produced by Sporotrichum thermophile was purified to homogeneity. The native StFaeC was homodimer with a subunit of Mr 23,000 and pI 3.1. The enzyme activity was optimal at pH 6.0 and 55 °C. The esterase displayed remarkable stability at pH 10.0 and retained 50% of its activity after 133 and 55 min at 55 and 60 °C, respectively. Determination of kcat/Km revealed that the enzyme had a broad spectrum of activity against the (hydroxyl) cinnamate esters indicating a type C feruloyl esterase. The enzyme was active on substrates containing ferulic acid ester linked to the C-5 and C-2 linkages of arabinofuranose and hydrolysed 4-nitrophenyl-5-O-trans-feruloyl-α-l-arabinofuranoside three times more efficiently than 4-nitrophenyl-2-O-trans-feruloyl-α-l-arabinofuranoside. Ferulic acid was efficiently released from wheat bran when the esterase was incubated together with xylanase from S. thermophile (a maximum of 41% total ferulic acid released after 1 h incubation). StFaeC by itself could release FA but at a level almost 10-fold lower than that obtained in the presence of xylanase. The potential of StFaeC for the synthesis of various phenolic acid esters was examined using as a reaction system a ternary water–organic mixture consisting of n-hexane, 1-butanol and water. Also StFaeC catalyzed the transfer of the feruloyl group to l-arabinose in a similar system using t-butanol, with about a 40% conversion of l-arabinose to feruloylated derivative was achieved. This work is the first example of enzymatic feruloylation of a carbohydrate. 相似文献
7.
With the successful development of methods for the isolation and purification of ethanol-insoluble cinnamic acid esters in mint it became possible to initiate kinetic, isotopic studies on purified, ‘insoluble’ derivatives of caffeic acid, ferulic acid and p-coumaric acid. Pulse-feeding experiments were conducted with 14CO2, phenylalanine-U-14C and cinnamic acid-3-14C. The ferulic acid derivative exhibited a significant turnover as compared to the other insoluble derivatives which were relatively stable. Time-course tracer studies were performed to compare the turnover of soluble caffeic acid derivatives with ‘insoluble’ forms of caffeic acid. Caffeic acid associated with a macromolecular fraction consistently showed a higher specific activity than either soluble caffeic acid or the caffeic acid associated with a second insoluble derivative. 相似文献
8.
《Bioorganic & medicinal chemistry》2019,27(20):114918
Twelve N-hydroxycinnamoyl amino acid amide ethyl esters (CAES) were synthesized by using l-amino acid ethyl ester hydrochloride and corresponding cinnamic acid (ferulic acid, acetylferulic acid and caffeic acid) as raw materials in the presence of a catalytic amount of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide-hydrochloride (EDC) and 1-hydroxybenzotriene (HOBt). The 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activities of CAES were evaluated. The anti-tyrosinase activities of N-feruloyl amino acid ethyl esters and the hydroxyl (OH) free radical scavenging activities of N-caffeoyl amino acid ethyl esters were also examined. DPPH free radical scavenging activity was shown in all CAES, of which N-caffeoyl amino acid ethyl esters demonstrated higher radical scavenging activity than N-feruloyl amide derivatives, and (E) -N-(caffeic acid)-l-glycinate ethyl ester (c5) had the strongest ability to scavenge free radicals with an IC50 value of 18.6 µM. The acetylferuloyl amino acid esters exhibited the highest tyrosinase inhibition activity among the tested amides. 相似文献
9.
Horseradish peroxidase (HRP)-dependent oxidation of 3, 4-dihydroxyphenylalanine (dopa) was studied to elucidate the mechanism
of its oxidation. The oxidation of dopa was enhanced by hydroxycinnamic acid esters and dopa supressed HRP-dependent oxidation
of the esters. These results indicate that phenoxyl radicals of hydroxycinnamic acid esters that are formed at first, can
oxidize dopa. Among hydroxycinnamic acid esters used, affinity of the phenoxyl radicals for dopa was in order 4-coumaric>caffeic>ferulic
acid ester radicals. 相似文献
10.
Yung-Hun Yang Takao Raku Eunjung Song Sung-Hee Park Dongwon Yoo Hyung-Yeon Park Byung-Gee Kim Hyung-Ju Kim Sang-Hyun Lee Hyung-Sup Kim Yutaka Tokiwa 《Biotechnology and Bioprocess Engineering》2012,17(1):50-54
To perform the lipase-catalyzed synthesis of L-ascorbic acid derivatives from plant-based compounds such as cinnamic and ferulic acid under mild reaction conditions, the activities of immobilized Candida ntarctica lipase with different cinnamic acid esters and substituted cinnamic acids were compared. As a result, immobilized C. ntarctica lipase was found to prefer vinyl cinnamic acid to other esters such as allyl-, ethyl-, and isobutyl cinnamic acids as well as substituted cinnamic acids such as p-coumaric acid, caffeic acid, ferulic acid, and sinapic acid. Based on these results, large-scale synthesis of 6-O-cinnamyl-L-ascorbic acid ester was performed using immobilized C. ntarctica lipase in dry organic solvent, resulting in 68% yield (493 mg) as confirmed by 13C-NMR. 相似文献
11.
Myung-Suk Choi Ji-Hyun Park Ji Yun Min Bu-Kug Lim Byung Hyun Lee Gang Won Jung Jong-Yoon Lee Chandrakant S. Karigar Jae-Kyung Yang 《Biotechnology and Bioprocess Engineering》2008,13(3):319-324
An efficient method for release of ferulic acid from sweet potato stems was developed. Ferulic acid along with phenolic compounds
were released from stems by acid and alkaline treatments. The base hydrolysis with 0.1 N NaOH yielded the highest quantity
of total extracts (471.1 mg/g). The stems released more phenolic compounds when 0.0125∼0.025 N NaOH was employed. Where as
ferulic acid release was maximal with 0.05 N H2SO4 (0.32 mg/g). Ferulic acid was separated from phenolics by column chromatography. Among the elution solvents, ethyl acetate
fractions (80%) contained ferulic acid. Ethyl acetate eluants were further fractionated with n-hexane/ethyl acetate/formic acid (100/50/0.5, v/v/v). All fractions showed ferulic acid and phenolic compounds. Fraction
V among them was ascribed to ferulic acid with an yield of 5.41 mg/g of dry sweet potato tissue. 相似文献
12.
Topakas E Moukouli M Dimarogona M Christakopoulos P 《Applied microbiology and biotechnology》2012,94(2):399-411
A ferulic acid esterase (FAE) from the thermophilic fungus Myceliophthora thermophila (synonym Sporotrichum thermophile), belonging to the carbohydrate esterase family 1 (CE-1), was functionally expressed in methylotrophic yeast Pichia pastoris. The putative FAE from the genomic DNA was successfully cloned in P. pastoris X-33 to confirm that the enzyme exhibits FAE activity. The recombinant FAE was purified to its homogeneity (39 kDa) and subsequently
characterized using a series of model substrates including methyl esters of hydroxycinnamates, alkyl ferulates and monoferuloylated
4-nitrophenyl glycosides. The substrate specificity profiling reveals that the enzyme shows a preference for the hydrolysis
of methyl caffeate and p-coumarate and a strong preference for the hydrolysis of n-butyl and iso-butyl ferulate. The enzyme was active on substrates containing ferulic acid ester linked to the C-5 and C-2 linkages of arabinofuranose,
whilst it was found capable of de-esterifying acetylated glucuronoxylans. Ferulic acid (FA) was efficiently released from
destarched wheat bran when the esterase was incubated together with an M3 xylanase from Trichoderma longibrachiatum (a maximum of 41% total FA released after 1 h incubation). Prediction of the secondary structure of MtFae1a was performed in the PSIPRED server whilst modelling the 3D structure was accomplished by the use of the HH 3D structure
prediction server. 相似文献
13.
Proposed Model for the Peroxidase-Catalyzed Oxidation of Indole-3-acetic Acid in the Presence of the Inhibitor Ferulic Acid 总被引:3,自引:3,他引:0
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Gelinas DA 《Plant physiology》1973,51(5):967-972
Linear increments in ferulic acid concentration produce logarithmic increases in the ferulic acid-induced lag periods prior to the peroxidase-catalyzed oxidation of indole-3-acetic acid in a system containing 2,4-dichlorophenol and MnCl2 in acetate buffer at pH 5.6. Maintaining the ratio of indole-3-acetic acid to ferulic acid constant at 100 while linearly raising the ferulic acid concentration results in linear increases in the lag period. Both indole-3-acetic acid and ferulic acid are substrates of horseradish peroxidase in the presence of H2O2, and indole-3-acetic acid competitively inhibits the oxidation of ferulic acid. A model for the enzymatic oxidation of indole-3-acetic acid catalyzed by peroxidase is proposed. 相似文献
14.
Four phenylpropanoid esters, cimiracemates A-D (1-4), along with three known compounds, isoferulic acid, ferulic acid and methyl caffeate were isolated from the EtOAc fraction of the rhizome of Cimicifuga racemosa. The structures of the esters were elucidated by means of spectral data, including 2D NMR spectroscopy. 相似文献
15.
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
16.
Smirnov SA Koroleva OV Gavrilova VP Belova AB Klyachko NL 《Biochemistry. Biokhimii?a》2001,66(7):774-779
Laccases from the Basidiomycetes Coriolus hirsutus, Coriolus zonatus, Cerrena maxima, and Coriolisimus fulvocinerea have been isolated and purified to homogeneity and partially characterized. The kinetics of oxidation of different methoxyphenolic compounds by the fungal laccases has been studied. As laccase substrates, such methoxyphenolic compounds as 4-hydroxy-3,5-dimethoxycinnamic acid (sinapinic acid), 4-hydroxy-3-methoxycinnamic acid (ferulic acid), and 2-methoxyphenol (guaiacol) were used. The stoichiometries of the enzymatic reactions were determined: guaiacol and sinapinic acid are one-electron donors and their oxidation apparently results in the formation of dimers. It was established that k
cat/K
m, which indicates the effectiveness of catalysis, increases in the series guaiacol, ferulic acid, and sinapinic acid. This fact might be connected with the influence of substituents of the phenolic ring of the substrates. This phenomenon was established for fungal laccases with different physicochemical properties, amino acid composition, and carbohydrate content. This suggests that all fungal laccases possess the same mechanism of interaction between organic substrate electron donors and the copper-containing active site of the enzyme and that this interaction determines the observed values of the kinetic parameters. 相似文献
17.
Luteolin, kaempferol, quercetin, caffeic acid and ferulic acidwere identified in acid-hydrolyzed epidermal strips of Tradescantiavirginiana using HPLC and spectrophotometry. The amount of flavonoidswas much smaller than that of cinnamic acid derivatives. Morethan 80% of the flavonoids were found in methanol extracts ofepidermal strips. Caffeic acid was found in both methanol extractsand the residues in nearly equal amounts, while more than 80%of the ferulic acid was found in the residues after methanolextraction. These data suggest that most of the ferulic acidand part of the caffeic acid bind to macromolecules as estersin the cell wall and that flavonoids are localized mainly inthe cytoplasm. The localization of esters of hydroxycinnamicacids in cell walls was ascertained by fluorometric analysis.These phenolic compounds were oxidized by H2O2 (0.0251mM) in epidermal and guard cells and the oxidation was inhibitedby KCN and NaN3: luteolin glycosides were less sensitive toH2O2 than quercetin and kaempferol glycosides in flavonoids.Ferulic acid esters were more sensitive to H2O2 than caffeicacid esters in hydroxycinnamic acid derivatives. On the basisof these data, the physiological significance of the oxidationof phenolic compounds by H2O2 is discussed. (Received October 9, 1987; Accepted February 3, 1988) 相似文献
18.
Maria de Lourdes Lucio Ferrarese Nilson Evlázio de Souza João Domingos Rodrigues Osvaldo Ferrarese-Filho 《Acta Physiologiae Plantarum》2001,23(4):421-427
The objective of this research was to investigate how the allelochemical ferulic acid affects the carbohydrate and lipid contents
of soybean roots cultivated in nutrient culture. The results presented revealed that ferulic acid has significant effects
on carbohydrates by the increase in xylose, fructose and sucrose and decrease in glucose, after 24 h treatment of roots. Ferulic
acid increased the contents of saturated and unsaturated fatty acids of the polar and non-polar lipid fractions. The results
may contribute as additional data to explain allelopathic effects caused by ferulic acid. 相似文献
19.
Esters of ferulic acid with monoterpene alcohols were found in ponderosa pine oleoresin. These colorless ferulic acid esters are responsible for a yellow band seen on DEAE-Sephadex fractionation of the oleoresin. Two diterpene resin acids not previously found in pines and several resin acid artifacts were identified. 相似文献
20.
Olga Serra Carolin Hohn Rochus Franke Salomé Prat Marisa Molinas Mercè Figueras 《The Plant journal : for cell and molecular biology》2010,62(2):277-290
Suberin and waxes embedded in the suberin polymer are key compounds in the control of transpiration in the tuber periderm of potato (Solanum tuberosum). Suberin is a cell‐wall biopolymer with aliphatic and aromatic domains. The aliphatic suberin consists of a fatty acid polyester with esterified ferulic acid, which is thought to play an important role in cross‐linking to the aromatic domain. In potato, ferulic acid esters are also the main components of periderm wax. How these ferulate esters contribute to the periderm water barrier remains unknown. Here we report on a potato gene encoding a fatty ω‐hydroxyacid/fatty alcohol hydroxycinnamoyl transferase (FHT), and study its molecular and physiological relevance in the tuber periderm by means of a reverse genetic approach. In FHT RNAi periderm, the suberin and its associated wax contained much smaller amounts of ferulate esters, in agreement with the in vitro ability of the FHT enzyme to conjugate ferulic acid with ω‐hydroxyacid and fatty alcohols. FHT down‐regulation did not affect the typical suberin lamellar ultrastructure but had significant effects on the anatomy, sealing properties and maturation of the periderm. The tuber skin became thicker and russeted, water loss was greatly increased, and maturation was prevented. FHT deficiency also induced accumulation of the hydroxycinnamic acid amides feruloyl and caffeoyl putrescine in the periderm. We discuss these results in relation to the role attributed to ferulates in suberin molecular architecture and periderm impermeability. 相似文献