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1.
Summary Chili pepper (Capsicum annuum L., cv. Tampique?o 74) cell suspensions were employed to study the influence of phenylalanine and phenylpropanoids on the
total production of capsaicinoids, the hot taste compounds of chili pepper fruits. The effect of capsaicinoid precursors and
intermediates on the accumulation of lignin as an indicator of metabolic diversion was also investigated. Addition of 100
μM of either phenylalanine, cinnamic or caffeic acids to chili pepper cell cultures did not cause significant increases in total
capsaicinoids (expressed as capsaicin content, and calculated as averages of the measured values) during the growth cycle.
The highest total capsaicinoid content was recorded in cultures grown in the presence of vanillin (142.61 μg g−1 f.wt.), followed by cells treated with 100 μM vanillylamine (104.88 μg g−1 f.wt.), p-coumaric acid (72.36 μg g−1 f.wt.). and ferulic acid (34.67 μg g−1 f.wt.). Capsaicinoid content for control cells was 13.97 μg g−1 f.wt. Chili pepper cell suspensions cultured in the presence of 100 μM of either phenylalanine, or cinnamic, caffeic, or ferulic acids, or the same concentration, of vanillin and vanillylamine,
did not exhibit statistically significant differences in the content of lignin as compared with control cells. However, addition
of p-coumaric acid (100 μM) to the cultute medium significantly increased thelignin production (c. 10–15 times the contents of control cells). 相似文献
2.
Regulation of phenylpropanoid metabolism by exogenous precursors in axenic cultures of Sphagnum fallax 总被引:1,自引:0,他引:1
Sphagnum plantlets, cultivated in continuous-feed bioreactors, are characterised by high levels of free endogenous phenolics and a pronounced excretion of some phenolics into the effluent culture medium. The transfer of Sphagnum fallax, precultivated in continuous-feed bioreactors, to batch cultures resulted in an increased flux through phenylpropanoid metabolism and an accumulation of p-coumaric acid to 0.1 μM and of trans-sphagnum acid up to 0.5 μM in the external medium [3H]-labelled L-phenylalanine (7.7 GBq mol?1) was rapidly taken up, resulting in an enhanced synthesis and excretion of p-coumaric and trans-sphagnum acid. Specific activities were 6.9 and 5.4 GBq mol?1, respectively, for these cinnamic acids excreted into the external medium. Endogenous pools of trans-cinnamic and p-coumaric acid did not increase and no labelling could be detected in these compounds. Cell wall-bound activity amounted to ca 14% of the applied activity after 48 h of incubation, 59% of which was recovered in dioxane/2 M HCl extracts of the cell wall. Exogenously applied trans-cinnamic acid (0.1 mM) was taken up to 46% and resulted in a transient endogenous accumulation of trans-cinnamic acid, the level of free endogenous p-coumaric and trans-sphagnum acid was found to have decreased. The concentrations of p-coumaric and trans-sphagnum acid in the culture medium rose to 17 and 2.4 μM, respectively, after 48 h of incubation in 0.1 mMtrans-cinnamic acid. Exogenously applied p-coumaric acid (0.1 mM) was taken up to 79% from the incubation solution but not stored endogenously, as metabolic products trans-sphagnum acid and an unknown p-coumaric acid-conjugate accumulated in the external medium and endogenously. These results give evidence for the biosynthetical route from phenylalanine to sphagnum acid and a channelling of pathway intermediates by the enzymes L-phenylalanine ammonia-lyase (EC 4.3.1.5) and cinnamic acid 4-hydroxylase (EC 1.14.13.11). 相似文献
3.
A cell wall fraction isolated from epicotyls of Vigna angularis,which contained both ionically and covalently bound peroxidases,rapidly oxidized p-coumaric, caffeic and ferulic acids and slowlyoxidized sinapic acid. The oxidation of sinapic acid was greatlyenhanced in the presence of p-coumaric, caffeic or ferulic acid.Ascorbate (20 µM) inhibited the oxidation of ferulic acidby about 70% and completely inhibited the oxidation of p-coumaricand ferulic acids. The cell wall fraction was capable of bindingferulic and sinapic acids but not caffeic acid. p-Coumaric acidbound only slightly to cell walls. The oxidation of p-coumaricand ferulic acids by KCl-washed cell walls was inhibited byabout 60% and 10%, respectively, by 20 µM ascorbate, butthe oxidation of caffeic acid was completely inhibited by ascorbateat less than 20 µM. The oxidation of derivatives of hydroxycinnamicacid by peroxidases released from cell walls by washing with1 M KCl was completely inhibited by ascorbate. These resultssuggest that the inhibition by ascorbate depends on the substituentgroup of the phenyl ring of the derivatives of hydroxycinnamicacid when the oxidation reaction is catalyzed by cell wall-boundperoxidases and that the oxidation of sinapic acid is mediatedby phenoxyl radicals of derivatives of hydroxycinnamic acidother than sinapic acid. (Received December 2, 1993; Accepted March 3, 1994) 相似文献
4.
Interaction of Moisture Stress and Three Phenolic Compounds on Lettuce Seed Germination 总被引:2,自引:0,他引:2
No interactions between water stress and three phenolic acids(p-coumaric, caffeic and ferulic acids) on lettuce (Lactucasativa L. var. Grand Rapids) seed germination were found. Probitanalysis indicated that mechanisms of action of water stressand the phenolic inhibitors were similar. The relative effectivenessof the compounds was p-coumaric > ferulic > caffeic. Nointeraction was found between p-coumaric and ferulic acid, whereasantagonism was found between caffeic acid and each of the othertwo phenolic acids. Lactuca sativa L., lettuce, germination, phenolic compounds, moisture stress, allelopathy, seed 相似文献
5.
Tanoh Hilaire Kouakou Pierre Waffo-Téguo Yatty Justin Kouadio Josep Valls Tristan Richard Alain Decendit Jean-Michel Mérillon 《Plant Cell, Tissue and Organ Culture》2007,90(1):25-29
Studies of phenolic compounds were performed during cell suspension cultures in relation with the induction of embryogenic
structures in two cultivars of cotton. Coker 312 produced embryogenic structures, unlike R405-2000 which was found to be a
non-embryogenic cultivar. Embryogenesis induction in Coker 312 was strongly linked to a higher content of caffeic, ferulic
and salicylic acids and to the appearance of p-coumaric acid, benzoic acid, trans-resveratrol, catechin and naringenin. 相似文献
6.
Rogério Barbosa Lima Victor Hugo Salvador Wanderley Dantas dos Santos Gisele Adriana Bubna Aline Finger-Teixeira Anderson Ricardo Soares Rogério Marchiosi Maria de Lourdes Lucio Ferrarese Osvaldo Ferrarese-Filho 《PloS one》2013,8(12)
Cinnamic acid and its hydroxylated derivatives (p-coumaric, caffeic, ferulic and sinapic acids) are known allelochemicals that affect the seed germination and root growth of many plant species. Recent studies have indicated that the reduction of root growth by these allelochemicals is associated with premature cell wall lignification. We hypothesized that an influx of these compounds into the phenylpropanoid pathway increases the lignin monomer content and reduces the root growth. To confirm this hypothesis, we evaluated the effects of cinnamic, p-coumaric, caffeic, ferulic and sinapic acids on soybean root growth, lignin and the composition of p-hydroxyphenyl (H), guaiacyl (G) and syringyl (S) monomers. To this end, three-day-old seedlings were cultivated in nutrient solution with or without allelochemical (or selective enzymatic inhibitors of the phenylpropanoid pathway) in a growth chamber for 24 h. In general, the results showed that 1) cinnamic, p-coumaric, caffeic and ferulic acids reduced root growth and increased lignin content; 2) cinnamic and p-coumaric acids increased p-hydroxyphenyl (H) monomer content, whereas p-coumaric, caffeic and ferulic acids increased guaiacyl (G) content, and sinapic acid increased sinapyl (S) content; 3) when applied in conjunction with piperonylic acid (PIP, an inhibitor of the cinnamate 4-hydroxylase, C4H), cinnamic acid reduced H, G and S contents; and 4) when applied in conjunction with 3,4-(methylenedioxy)cinnamic acid (MDCA, an inhibitor of the 4-coumarate:CoA ligase, 4CL), p-coumaric acid reduced H, G and S contents, whereas caffeic, ferulic and sinapic acids reduced G and S contents. These results confirm our hypothesis that exogenously applied allelochemicals are channeled into the phenylpropanoid pathway causing excessive production of lignin and its main monomers. By consequence, an enhanced stiffening of the cell wall restricts soybean root growth. 相似文献
7.
Kinetic study of possible intermediates in the biosynthesis of chlorogenic acid in Cestrum poeppigii
p-Coumaric and 3-O-p-coumarylquinic acid seem to be important precursors of chlorogenic acid in the leaves of Cestrum poeppigii. 3-O-Cinnamylquinic acid, which has a very small metabolic activity, is of little importance in this respect. The kinetics of incorporation of radioactivity from t-cinnamic acid-3-[14C] into p-coumaric, 3-O-p-coumarylquinic, chlorogenic and 3-O-cinnamylquinic acid showed that the biosynthetic rates for these products decrease in the order shown. For p-coumaric acid, which has a markedly high metabolic activity, a turnover rate of 28 μg/hr and per gram fresh plant leaf, was calculated. Some trapping experiments with caffeic acid, and the acids mentioned above and using either t-cinnamic acid-3-[14C] or p-coumaric acid-2-[14C] as precursor, are discussed. A HPLC method for the rapid determination of phenolic acids in plant extracts, is described. 相似文献
8.
Estrada Alvarado Isabel Navarro David Record Eric Asther Michèle Asther Marcel Lesage-Meessen Laurence 《World journal of microbiology & biotechnology》2003,19(2):157-160
Fungal biotransformation of p-coumaric acid into caffeic acid, potentially a strong antioxidant, was evidenced in Pycnoporus cinnabarinus cultures grown with high feeding of p-coumaric acid. Preliminary experiments showed no toxicity of both p-coumaric and caffeic acids at concentrations ranging from 0 to 500 mg l–1. Feeding 450 mg p-coumaric acid l–1 into P. cinnabarinus cultures grown on 20 g l–1 glucose medium resulted in the production of 257 mg caffeic acid l–1with a molar yield of 21%. 相似文献
9.
Toda S 《Biological trace element research》2002,85(2):183-188
We present the results of an in vitro investigation of the inhibitory effects of phenylpropanoid metabolites on copper-induced
protein oxidative modification of mice brain homogenate. The effects of caffeic acid, 3-(3, 4-dihydroxyphenyl)-l-alanine, esculetin, ferulic acid, and scopoletin were stronger than that of mannitol as a free-radical scavenger, whereas
the effects of other phenylpropanoid metabolites, cinnamic acid, coniferyl alcohol, p-coumaric acid, coumarin, phenylalanine, tyrosine, and umbelliferone, were weak. These results demonstrated that phenolic
carboxylic acids with 3,4-dihydroxy or 4-hydroxy-3-methoxy substituents and benzo-α-pyrons with 6,7-dihydroxy or 7-hydroxy-6-methoxy
substituents in phenylpropanoid metabolites inhibit metal-induced protein oxidative modification of the brain. 相似文献
10.
The ability of grape skins to catalyze in vitro conversion of p-coumaric acid to the more potent antioxidant caffeic acid was studied. Addition of different concentrations of p-coumaric to red grape skins (Cabernet Sauvignon) resulted in formation of caffeic acid. This caffeic acid formation (Y) correlated
positively and linearly to p-coumaric acid consumption (X): Y = 0.5 X + 9.5; R
2 = 0.96, P < 0.0001. The kinetics of caffeic acid formation with time in response to initial p-coumaric acid levels and at different grape skin concentrations, indicated that the grape skins harboured an o-hydroxylation activity, proposedly a monophenol- or a flavonoid 3′-monooxygenase activity (EC 1.14.18.1 or EC 1.14.13.21).
The K
m of this crude o-hydroxylation activity in the red grape skin was 0.5 mM with p-coumaric acid. 相似文献
11.
Naturally occurring plant phenolics,p-coumaric acid (PA), caffeic acid (CA), ferulic acid (FA) and gentisic acid (GA) (25–100 nmol/L) had protective effects on
acridine orange (AO; 216 μmol/L)- and ofloxacin (3 μmol/L)-induced genotoxicity inSalmonella typhimurium. FA, GA and CA exhibited a significant concentration-dependent protective effect against the genotoxicity of AO and ofloxacin,
with the exception of PA, which at all concentrations tested abolished the AO and ofloxacin genotoxicity. UV spectrophotometric
measurements showed the interaction of PA, FA, GA and CA with AO but not with ofloxacin; this interaction is obviously responsible
for the reduction of AO-inducedS. typhimurium mutagenicity. In the case of ofloxacin the antimutagenic effect of PA, FA, GA and CA is assumed to be a result of their ability
to scavenge reactive oxygen species (ROS) produced by ofloxacin. 相似文献
12.
《Phytochemistry》1987,26(8):2418-2420
Besides apigenin and luteolin 7-glucoside, four novel luteolin glucosides acylated with acetic,trans-cinnamic,p-coumaric andferulic acids, re acyl groups was determined to be at C-6″ by the13C NMR spectral data. 相似文献
13.
Pinton Roberto Cesco Stefano Iacolettig Gabriele Astolfi Stefania Varanini Zeno 《Plant and Soil》1999,215(2):155-161
The effect of a water extractable humic substances fraction (WEHS) on nitrate uptake and plasma membrane (pm) H+-ATPase activity of maize roots was investigated. Four days old maize root seedlings were exposed for 4 to 24 h to a nutrient
solution containing 200 μ M nitrate in the absence or presence of 5 mg org. C { L
-1 WEHS. Plants exposed to nitrate developed a higher capacity to absorb the anion (induction): the net uptake rate progressively
increased up to 12 h of contact with the solution; thereafter, a decline was observed. When WEHS was present together with
nitrate in the nutrient solution, the induction of nitrate uptake was evident and maximal already 4 h after starting the treatment.
The rate of net nitrate uptake decreased only slightly during the remaining period (4-24 h). Stimulation of net nitrate uptake
rate was also observed when WEHS was added to a nitrogen- or nitrate-free nutrient solution or to a 5 mM CaSO4 solution. The activity of pmH+-ATPase raised upon exposure of the roots to nitrate with the same pattern observed for nitrate uptake. The contemporary presence
of nitrate and WEHS caused a further stimulation of the pmH+-ATPase activity after 4 h treatment. An increase in the enzyme activity was also observed when plants were treated for 4
h in the presence of WEHS in CaSO4, nitrogen- or nitrate-free solutions. However, when nitrate was present the enhancement was even greater. Results support
the idea that the plasma membrane proton pump might be one of the primary targets of the action of humic substances on plant
nutrient acquisition. A role of WEHS in the modulation of nitrate uptake via an interaction with the pm H+-ATPase is also discussed.
This revised version was published online in June 2006 with corrections to the Cover Date. 相似文献
14.
Hydroxycinnamates are among the most widely distributed plant phenylpropanoids present in the free, conjugated-soluble and
insoluble-bound forms. This review will focus on the occurrence, in vitro and in vivo antioxidant activities of ferulic, coumaric,
caffeic and sinapic acids and their derivatives. Hydroxycinnamates are found in almost all food groups though they are abundant
in cereals, legumes, oilseeds, fruits, vegetables and beverages and render antioxidant activity by scavenging hydroxyl radical,
superoxide radical anion, several organic radicals, peroxyl radical, peroxinitrite and singlet oxygen, among others. Further,
their antioxidant activity as chain breaking antioxidants and reducing agents is also notable. Ferulic acid and its derivatives
such as ferulic acid ethyl ester, ferulic acid dehydrodimers, feruloyl glycosides and curcumin have demonstrated potent antioxidant
activity in both in vitro and in vivo systems. Similarly, caffeic acid and some of its derivatives such as caffeic acid phenethyl
ester, rosmarinic acid, and chlorogenic acid exhibit antioxidant activity. The highest antioxidant activity was observed for
caffeic acid whereas p-coumaric acid had the least effect among major hydroxycinnamic acids. The importance of structural effects on the potency
of antioxidant activity of hydroxycinnamates is discussed. While this review also shows the existence of substantial body
of evidences for in vitro antioxidant activity of hydroxycinnamates, there is a clear gap for in vivo information, particularly
for sinapic and p-coumaric acids and their derivatives. The role of grains, fruits, vegetables and red wine in disease risk reduction and health
promotion could partly be attributed to their constituent hydroxycinnamates. 相似文献
15.
16.
Mohammad Safari Mohammad Safari Salwa Karboune Richard St-Louis 《Biocatalysis and Biotransformation》2013,31(4):272-279
The synthesis of structured phenolic lipids by lipase-catalyzed transesterification of selected phenolic acids, including p-hydroxyphenyl acetic, p-coumaric, sinapic, ferulic and 3,4-dihydroxybenzoic acids, with triolein was investigated. The highest enzymatic activity (248?nmol esterified phenolic acid/g solid enzyme/min) and bioconversion (62%) was obtained for the transesterification of p-hydroxyphenyl acetic acid with triolein. In addition, the transesterification of p-coumaric with triolein resulted in a higher enzymatic activity (87?nmol esterified phenolic acid/g solid enzyme/min) and bioconversion (46%) than those obtained for the transesterfication of ferulic and sinapic acids. The results also showed that using p-hydroxyphenyl acetic, p-coumaric and ferulic acids as substrate, the maximum bioconversion of phenolic monoacylglycerols was close to that of phenolic diacylglycerols. Although p-coumaric acid had very low radical scavenging activity (2%) compared to that of ferulic acid (62%), the p-coumaroylated lipids demonstrated a higher scavenging potency (16%) than that of the feruloylated one (10%). 相似文献
17.
Dynamics of phenolic acids and lignin accumulation in metal-treated Matricaria chamomilla roots 总被引:2,自引:0,他引:2
Phenylalanine ammonia-lyase (PAL) activity, 11 phenolic acids and lignin accumulation in Matricaria chamomilla roots exposed to low (3 μM) and high (60 and 120 μM) levels of cadmium (Cd) or copper (Cu) for 7 days were investigated.
Five derivatives of cinnamic acid (chlorogenic, p-coumaric, caffeic, ferulic and sinapic acids) and six derivatives of benzoic acid (protocatechuic, vanillic, syringic, p-hydroxybenzoic, salicylic acids and protocatechuic aldehyde) were detected. Accumulation of glycoside-bound phenolics (revealed
by acid hydrolysis) was enhanced mainly towards the end of the experiment, being more expressive in Cu-treated roots. Interestingly,
chlorogenic acid was extremely elevated by the highest Cu dose (21-fold higher than control) suggesting its involvement in
antioxidative protection. All compounds, with the exception of chlorogenic acid, were detected in the cell wall bound fraction,
but only benzoic acids were found in the ester-bound fraction (revealed by alkaline hydrolysis). Soluble phenolics were present
in substantially higher amounts in Cu-treated roots and more Cu was retained there in comparison to Cd. Cu strongly elevated
PAL activity (by 5.4- and 12.1-fold in 60 and 120 μM treatment, respectively) and lignin content (by 71 and 148%, respectively)
after one day of treatment, indicating formation of a barrier against metal entrance. Cd had slighter effects, supporting
its non-redox active properties. Taken together, different forms of phenolic metabolites play an important role in chamomile
tolerance to metal excess and participate in active antioxidative protection. 相似文献
18.
Anodic oxidation of coumaric acid led to the inhibition of the process at the electrode due to a film which was formed after
one-electron oxidation of the acid to phenoxy radical.By contrast, caffeic acid is oxidized in two steps-the phenoxy radical
is formed in the first step, quinone in the second step. The inhibition of nitrate uptake by coumaric and caffeic acids is
dependent on their concentration. 10-4 M eaffeic acid totally inhibited nitrate uptake and the growth ofNicotiana tabacum cell suspension. 10-6 M caffeic acid markedly inhibited nitrate uptake especially in the first three days after inoculation. 10-6 M coumaric acid did not affect nitrate uptake and nitrate reductase activity, 10-4 M coumaric acid inhibited nitrate uptake by day two after inoculation. Nitrate reductase synthesis correlated with the inhibition
of nitrate uptake. Differential effects of coumaric and caffeic acids are explained on the basis of different products of
their electrochemical oxidation. 相似文献
19.
Biosynthetic pathways to p-hydroxybenzoic acid in polar lignin were examined by tracer experiments. High incorporation of radioactivity to the acid was observed when shikimic acid-[1-14C], phenylalanine-[3-14C], trans-cinnamic acid-[3-14C], p-coumaric acid-[3-14C] and p-hydroxybenzoic acid-[COOH-14C] were administered, while incorporation was low from shikimic acid-[COOH-14C], phenylalanine-[1-14C], phenylalanine-[2-14C], tyrosine-[3-14C], benzoic acid-[COOH-14C], sodium acetate-[1-14C] and d-glucose-[U-14C]. Thus p-hydroxybenzoic acid in poplar lignin is formed mainly via the pathway: shikimic acid → phenylalanine → trans-cinnamic acid → p-coumaric acid → p-hydroxybenzoic acid. 相似文献
20.
Two enzymes thought to be involved in the biosynthesis of chlorogenic acid have been separated and purified by ion exchange chromatography and their properties studied. These two enzymes, p-coumarate CoA ligase and hydroxycinnamyl CoA: quinate hydroxycinnamyl transferase, acting together catalyse the conversion of p-coumaric acid to 5′-p-coumarylquinic acid and of caffeic acid to chlorogenic acid. The ligase has a higher affinity for p-coumaric than for caffeic acid and will in addition activate a number of other cinnamic acids such as ferulic, isoferulic and m-coumaric acids but not cinnamic acid. The transferase shows higher activity and affinity with p-coumaryl CoA than caffeyl CoA. It also acts with ferulyl CoA but only very slowly. The enzyme shows high specificity for quinic acid; shikimic acid is esterified at only 2% of the rate with quinic acid and glucose is not a substrate. The transferase activity is reversible and both chlorogenic acid and 5′-p-coumarylquinic acids are cleaved in the presence of CoA to form quinic acid and the corresponding hydroxycinnamyl CoA thioester. 相似文献