Phenylpropanoid Content Research Articles

Diferulate Content of Maize Sheaths Is Associated with Resistance to the Mediterranean Corn Borer Sesamia nonagrioides (Lepidoptera: Noctuidae)

The leaf sheaths of selected inbred lines of maize (Zea mays L.) with variable levels of stem resistance to the Mediterranean corn borer Sesamia nonagrioides (Lefèvbre) were evaluated for antibiotic effect on insect development. Phytochemical analyses of leaf sheaths were conducted for cell wall phenylpropanoid content to gain a better understanding of maize-resistance mechanisms. Laboratory bioassays established that sheath tissues from different genotypes significantly affected the growth of neonate larvae. Three hydroxycinnamates, p-coumaric, trans-ferulic, and cis-ferulic acids, and three isomers of diferulic acid, 8-5', 8-O-4', and 8-5' b (benzofuran form), were identified. Significant negative correlations were found between larvae weight and diferulic acid content for six genotypes. These results are in agreement with previous studies concerning the role of cell wall structural components in stem borer resistance.

Different responses of shoot and root cultures of Glehnia littoralis to yeast extract

Differentiated shoot and root cultures of Glehnia littoralis were examined for organ-specific responses to yeast extract (YE). Growth, and changes in phenylalanine ammonia-lyase (PAL, EC 4. 1. 3. 5) activity, as well as furanocoumarin and simple phenylpropanoid production were then determined. YE affected root growth positively but negatively affected the growth of both the leaf and petiole. PAL activity was induced in all organs and reached a maximum after 2 days of treatment, though the activity in leaves was about three times higher than that in roots. A large amount of p-coumaric acid (p-CA) was transiently excreted into the culture medium of leaves, which has only been rarely reported to date. Subsequently, bergapten and xanthotoxin appeared in the medium. In contrast, no furanocoumarin was detected in the root cultures throughout the course of treatment. Changes in simple phenylpropanoid contents such as p-CA, caffeic acid (CafA) and ferulic acid (FA) in tissues were analyzed in three forms, i.e., free, soluble-conjugated and insoluble-conjugated forms. In leaves, little difference between control and YE-treated tissues was found except free p-CA, but every form of simple phenylpropanoid was increasingly elicited in the roots. These results indicate that YE acts bi-functionally on the root as a nutrient and an elicitor, but only as an elicitor in the leaf.

Putative Role of Pith Cell Wall Phenylpropanoids in Sesamia nonagrioides (Lepidoptera: Noctuidae) Resistance

The stem borer Sesamia nonagrioides (Lefèbvre) is the most important insect pest that attacks maize, Zea mays L., in northwestern Spain. Host plant resistance to this borer was investigated in relation to the cell wall phenylpropanoids content in the pith. Eight inbred lines that differ in resistance were analyzed. Three major simple phenolic acids, p-coumaric, trans-ferulic, and cis-ferulic acids, and three isomers of diferulic acid, 8-5', 8-O-4', and 8-5'b (benzofuran form), were identified. The amount of all these compounds was correlated with the resistance level in the genotypes, with the resistant inbreds having the highest concentrations. The role of these compounds in cell wall fortification and lignification is well-documented, suggesting their possible intervention in S. nonagrioides resistance. Future studies that focus on these compounds could be useful to enhance S. nonagroides resistance.

Wound-induced expression of the ferulate 5-hydroxylase gene in Camptotheca acuminata

The phenylpropanoid pathway plays important roles in plants following exposure to environmental stresses, such as wounding and pathogen attack, which lead to the production of a variety of compounds, including lignin, flavonoids and phytoalexins. Ferulate 5-hydroxylase (F5H) is a cytochrome P450-dependent monooxygenase that catalyses the hydroxylation of ferulic acid, coniferaldehyde and coniferyl alcohol, leading to sinapic acid and syringyl lignin biosynthesis. We isolated F5H cDNA and genomic DNA from Camptotheca acuminata and investigated the expression pattern of the C. acuminata F5H ( CaF5H1) gene in response to wounding. A search against the BLOCKS database of conserved protein motifs indicated that CaF5H1 retains features in common with F5Hs reported from other plants. 5′-flanking region analysis using the PLACE database showed that putative regulatory elements related to various abiotic and biotic stresses, such as drought, wounding, low temperature and pathogens, exist in the 5′-flanking region of CaF5H1. Based upon these analysis results, we investigated the expression pattern of CaF5H1 gene in response to wounding and stress-related molecules. Here, we show that CaF5H1 transcripts accumulated in the leaves in response to mechanical wounding or the application of molecules involved in the stress response, such as ethylene, ABA and hydrogen peroxide (H 2O 2). The application of salicylic acid and diphenylene iodonium (DPI) inhibited the wound-induced expression of CaF5H1. Taken together, we suggest that wound-induced expression of CaF5H1 may be mediated by MJ and H 2O 2 and enhanced phenylpropanoid contents via CaF5H1 maybe function in response to various stresses, including wounding, in plants.

Comparative screening of plant essential oils: Phenylpropanoid moiety as basic core for antiplatelet activity

Essential oils extracted from different plants ( Anthemis nobilis L., Artemisia dracunculus L., Cannabis sativa L., Cupressus sempervirens L., Cymbopogon citratus (DC.) Stapf., Curcuma longa L ., Foeniculum vulgare L., Hypericum perforatum L., Hyssopus officinalis L., Mentha spicata L., Monarda didyma L., Ocimum basilicum L ., Ocotea quixos Kosterm ., Origanum vulgare L., Pinus nigra J.F. Arnold, Pinus silvestris L., Piper crassinervium Kunth., Rosmarinus officinalis L ., Salvia officinalis L., Salvia sclarea L., Santolina chamaecyparissus L., Thymus vulgaris L., Zingiber officinaie L .) were screened in guinea pig and rat plasma in order to assess antiplatelet activity and inhibition of clot retraction. The oils were chemically analysed and a relationship between components and ability to affect hemostasis was evidenced. O. quixos, F. vulgaris, and A. dracunculus showed the highest antiplatelet activity against ADP, Arachidonic Acid and the Thromboxane A 2 agonist U46619 (IC 50, 4–132 μg ml − 1 ), and a good ability to destabilize clot retraction (IC 50, 19–180 μg ml − 1 ). For these oils a significant correlation between antiplatelet potency and phenylpropanoids content (54–86%) was evidenced thus suggesting a key role for this moiety in the prevention of clot formation. These findings provide the rationale to take in account the antiplatelet activity in the pharmacological screening of natural products containing phenylpropanoids.

Antioxidant Activity of Methanol Extracts Obtained from Plantago Species

Antioxidative activities of methanol extracts from five Plantago species (P. afra, P. coronopus, P. lagopus, P. lanceolata, and P. serraria) were characterized by the DPPH scavenging test and the inhibition of Fe2+/ascorbate-induced lipid peroxidation on bovine brain liposomes. All extracts showed antioxidant activity in both methods. Whereas P. serraria exhibited the strongest activity as a DPPH scavenger, P. lanceolata and P. serraria were found to be the most active in the lipid peroxidation inhibition assay. The extracts were investigated regarding their composition by different colorimetric techniques, such as the content of total phenolic compounds by the Folin-Ciocalteu assay, flavonoids by AlCl3 reagent, phenylpropanoid glycosides (PPGs) by Arnow reagent, and iridoids by Trim-Hill assay. A high correlation was found between the scavenging potency and the total phenolic and phenylpropanoid content of the extracts but not between the lipid peroxidation potency and the extract composition. P. serraria is presented as a possible new source of natural antioxidants.

Evaluation of Phenylpropanoids in Ten Capsicum annuum L. Varieties and Their Inhibitory Effects on Listeria monocytogenes Murray, Webb and Swann Scott A

Extracts of pepper from ten different varieties of Capsicum annuumL. were prepared and their phenylpropanoids content was analysed by HPLC. There were seven different compounds identified at varying concentrations depending on pepper variety (L-phenylalanine, t-cinnamic acid, o-coumaric acid, mcoumaric acid, ferulic acid, caffeic acid and capsaicin) which are intermediates of the capsaicinoids pathway. The inhibitory action of the pepper extracts was evaluated against Listeria monocytogenes Murray, Webb and Swann Scott A by the agar diffusion test. Results showed that three of the 10 extracts had an antibacterial effect. Guajillo San Luis pepper presented the highest inhibitory effect, and contained the major concentration of cinnamic and caffeic acids. In order to analyse the individual contribution of every phenylpropanoid to the bacteriostatic effect, different concentrations were tested on the growth and survival of L. monocytogenesSwann Scott A.There were no significant differences (p> 0.05) in the t-cinnamic, o-coumaric, m-coumaric, ferulic acids and capsaicin among the samples. However, a significant difference was found between these compounds and the bactericidal action of caffeic acid. The results confirmed that L. monocytogenesSwann Scott A is inhibited by some pepper extracts, and also that some specific phenylpropanoids had a bacteriostatic effect.

Hydroalcohol extract and fractions ofStachys lavandulifolia vahl: effects on spontaneous motor activity and elevated plus-maze behaviour

The present study aimed to investigate the anxiolytic effects of four fractions of Stachys lavandulifolia Vahl. The aerial parts of the plant were extracted with petroleum ether (PF), ethyl acetate (EF), butanol (BF) and water (AF) and tested for spontaneous motor activity and elevated plus-maze (EPM) behaviour in mice. The hydroalcohol extract (HE) and different fractions of S. lavandulifolia were administered intraperitoneally to male Syrian mice, at various doses, 30 min before the behavioural evaluation. The HE of S. lavandulifolia (at 50 mg/kg) increased the percentage of time spent (39%) and the percentage of arm entries in the open arms (53%). The HE (50 mg/kg), PF (25 and 50 mg/kg), EF (25 and 50 mg/kg) and AF (50 mg/kg) of S. lavandulifolia significantly increased the percentage of time spent and the percentage of arm entries in the open arms. The BF up to a dose of 50 mg/kg had no significant effects on any of the measured parameters in the EPM. The spontaneous locomotor activity was significantly decreased in animals injected with each plant fractions, compared with that of saline. The EF and AF showed the least and the most reduction in the activity, respectively. The anxiolytic effects of EF, PF and AF could be related to their content of flavonoids, phenylpropanoids or terpenoids.

The Arabidopsis phenylalanine insensitive growth mutant exhibits a deregulated amino acid metabolism.

Amino acids and amino acid analogs have been used in numerous genetic screens to isolate mutants deficient in amino acid biosynthetic pathways or in the regulation of amino acid metabolism. Several of these mutants exhibit relaxed feedback control of branched amino acid biosynthetic pathways and are thus resistant to accumulation of pathway end products. For example, feedback-regulated enzymes of the shikimate pathway are anthranilate synthase on the branch leading to Trp and chorismate mutase on the branch leading to Phe and Tyr. A feedback-insensitive mutant of anthranilate synthase alpha, trp5-1, is resistant to toxic Trp analogs. Mutants resistant to Phe have not previously been reported, and this article describes the isolation of the recessive Arabidopsis Phe insensitive growth mutant pig1-1 by a forward genetic screen. pig1-1 was not only tolerant to Phe, Tyr, and Trp, but also to other, not biosynthetically related amino acids. Amino acid contents in pig1-1 were significantly elevated with respect to wild-type controls but, in contrast to the wild type, dramatically decreased when plants were supplemented with 2 mm Phe. Protein contents were similar in the mutant and the wild type at all tested conditions. Phe catabolism was similar to the wild type in pig1-1 roots but was significantly increased in pig1-1 shoots. Phenylalanine uptake into the root, its root-to-shoot translocation, and Phe and phenylpropanoid contents were unaltered in pig1-1, indicating that pig1-1 is not affected in amino acid translocation or the shikimate pathway. Instead, the response of pig1-1 toward amino acid feeding indicates that amino acid metabolism is generally deregulated in pig1-1.

Light induces phenylpropanoid metabolism in Arabidopsis roots.

Experiments have shown that many phenylpropanoid genes are highly expressed in light-grown Arabidopsis roots. Studies employing reporter gene constructs have indicated that the expression of these genes is localized not only to the lignifying root vasculature, but also to non-lignifying tissues, such as the root cortex, suggesting that the proteins encoded by these genes may be involved in aspects of phenylpropanoid metabolism other than lignification. Consistent with this hypothesis, roots of etiolated and soil-grown plants contain almost no soluble phenylpropanoids, but exposure to light leads to the accumulation of flavonoids, as well as high levels of coniferin and syringin (coniferyl and sinapyl-4-O-glycosides), compounds not previously reported to be accumulated in Arabidopsis. To elucidate the mechanism by which light induces root secondary metabolism, extracts of mutants defective in light perception and light responses were analyzed for phenylpropanoid content. The results of these assays showed that phytochrome (PHY)B and cryptochrome (CRY)2 are the primary photoreceptors involved in light-dependent phenylpropanoid accumulation, and that the hypocotyl elongated (HY5) transcription factor is also required for this response. The presence of phenylpropanoids in etiolated roots of cop (constitutively photomorphogenic)1, cop9, and det (de-etiolated)1 mutants indicate that the corresponding wild-type genes are required to repress root phenylpropanoid biosynthesis in the absence of light. Biochemical analysis of root cell walls and analysis of phenylpropanoid gene expression suggest that coniferin and syringin accumulation may be the result of both increased biosynthesis and decreased conversion of these compounds into other phenylpropanoid end products. Finally, our data suggest that the accumulation of coniferin, syringin, and flavonoids in Arabidopsis roots is a high-irradiance response (HIR), and suggest that comparative analysis of light- and dark-grown Arabidopsis roots may provide new insights into both phenylpropanoid biosynthesis and light signaling in plants.

Identification of the components of the essential oil from wild Corsican Daucus carota L. using 13C‐NMR spectroscopy

AbstractThe essential oil of wild Daucus carota L. from Corsica was investigated by GC and 13C‐NMR spectroscopy. In a first part, a commercial sample was repeatedly chromatographed and the analysis of the fractions led to the identification of 69 components. The oil consisted chiefly of phenylpropanoids (45.9%) and monoterpene hydrocarbons (38.6%), with (E)‐methylisoeugenol (33.0%), α‐pinene (24.9%) and elemicin (11.4%) as major components. The second part concerned the analysis of laboratory‐distilled oils obtained from different parts of the plant at three stages of development (prior flowering, full flowering and end of flowering). The chemical composition of the Corsican wild carrot oil varies according to its stage of development. The oil yields, as well as the phenylpropanoid contents, particularly that of (E)‐methylisoeugenol, increase significantly when the umbels ripen. Copyright © 2004 John Wiley & Sons, Ltd.

Phenylpropanoid deficiency affects the course of plant acclimation to cold

The effects of phenylpropanoid deficiency on plant growth, photosynthetic efficiency of the photosystem II and freezing tolerance of leaves were studied during acclimation of winter oilseed rape plants (Brassica napus L. var. oleifera L. cv Jantar) at low temperature. Application of 2‐amino‐2‐indanophosphonic acid inhibited phenylalanine ammonia‐lyase (E.C. 4.3.1.5) activity by about 90%. This was followed by a marked reduction of soluble phenolics (in particular hydroxycinnamic acids) and anthocyanins in leaves. Inhibition of the cold‐promoted incorporation of ferulic acid into cell walls was also observed. The reduction of phenylpropanoid contents was associated with: (1) partial abrogation of the cold‐induced growth effects, such as inhibition of leaf fresh weight increments and accumulation of dry matter, proteins and cell walls; (2) decreased photochemical efficiency of photosystem II in low temperature‐affected leaves; and (3) decreased ability of leaves to develop tolerance to the extracellular formation of ice. These findings are discussed in terms of phenylpropanoids' role in plant responses to cold (> 0°C) and freezing temperatures.

Flavone C-glycoside, phenolic acid, and nitrogen contents in leaves of barley subject to organic fertilization treatments.

From the leaves of barley, Hordeum vulgare, one new flavone C-glucoside and three known flavone glucosides were isolated and characterized by (1)H and (13)C NMR and MALDI-TOF-MS. The novel flavone C-glucoside was isovitexin 7-O-beta-[6' "-O-(E)-p-coumaroyl]glucoside (6' "-coumaroylsaponarin), and the known compounds were isovitexin 7-O-beta-[6' "-O-(E)-feruloyl]glucoside, isoorientin 7-O-beta-[6' "-O-(E)-feruloyl]glucoside, and tricin 7-O-beta-glucoside. The sum of all the flavone glycosides and soluble phenolic acids in the leaves decreased with increased rate of plant nutrients given in animal manure and with increased crop yield. All of the major phenylpropanoids showed the same general response to nutrient level. The concentration of nitrogen in the leaves was not directly related to nutrient application or to contents of phenylpropanoids.

Duplicate Loci as QTL

The C-glycosyl flavone maysin is an important component of corn earworm (Helicoverpa zea Boddie) (CEW) resistance in maize (Zea mays L.) silks. Chlorogenic acid (CGA), a product of the phenylpropanoid pathway, has also been implicated in CEW antibiosis. The transition from the 9-carbon phenylpropanoid to the 15-carbon flavonoid pathway represents a potentially important regulation point in C-glycosyl flavone biosynthesis. The enzyme chalcone synthase (CHS) catalyzes this reaction and is represented by a set of duplicate loci in maize, colorless2 (c2) and white pollenl (whpl ). Chromosomal regions of the maize genome have been identified as quantitative trait loci (QTL) for maysin synthesis that correspond to these two loci. Our objective was to investigate the role of CHS in flavone and CGA biosynthesis. We tested c2 and whpl as candidate loci using three related F 2 populations segregating for both structural and regulatory loci. Silks were harvested and analyzed from each population for flavonoid and phenylpropanoid content. Phenotypic data was combined with linkage maps generated for each population to conduct statistical and QTL analysis. Our results (i) support earlier findings of the requirement of a functional pericarp color1 (p1) allele for C-glycosyl fiavone biosynthesis, ( ii) demonstrate that variation at the c2 region on chromosome 4 influences both maysin and CGA levels in silks, (iii) reveal a dosage-dependent relationship between c2 and whpl in which the whp1 region acts cooperatively with functional c2 to increase flavones and partially compensates for nonfunctional c2, and (iv) demonstrate that mutations in c2 and whpl shunt intermediates from maysin synthesis to CGA. These results demonstrate that CHS function is a regulatory focal point of substrate flow between the flavone and phenylpropanoid pathways.

Alterations in phenylpropanoid content in soybean roots during low temperature acclimation

L-Phenylalanine ammonia-lyase (PAL, EC 4.3.1.5) activity, growth and phenolic acid content during low temperature acclimation in soybean ( Glycine max. (L.) Merr.) roots were investigated. Elongation of soybean roots was inhibited after the transfer of 3-d-old seedlings grown at 25 to 10 °C. Extractable PAL activity as well as the total amount of phenolics increased 24 h after plant transfer to low temperature. The high pressure liquid chromatography analyses revealed the presence of six phenolic acids in soybean roots: p-hydroxybenzoic, vanillic, syringic, anisic, p-coumaric and ferulic. Analyses of different fractions of phenolic acids showed that during 24 h of low temperature exposure, an increase in the relative level of ester-bound-soluble phenolic acids occurred. The highest increase in this fraction was observed for ferulic acid (26 %). At the same time, a decrease in phenolic glycosides took place. The amount of phenolic acids released after alkaline treatment of the cell wall material was strongly inhibited (3-fold), which may suggest an alteration of the physical properties of the wall in acclimation to low temperature. The possible role of phenolics in acclimation to low temperature in roots is discussed.

Chemical and nutritional status of dwarf mistletoe, Armillaria root rot, and Comandra blister rust infected trees which may influence tree susceptibility to bark beetle attack

The terpenoid and phenyl propanoid content of xylem resin as well as phloem nitrogen and carbohydrate levels of lodgepole pine trees infected with Armillaria root disease, Comandra blister rust, and dwarf mistletoe and check (asymptomatic) trees were determined. Comparisons were made to determine if differences existed that might influence their susceptibility to bark beetle attack. These variables were also contrasted with respect to aspect (north and south). Five volatiles (tricyclene, α-pinene, camphene, γ-terpinene, and bornyl acetate) were significantly higher in trees with one or more diseases than in check trees. Four volatiles (myrcene, camphor, 4-allylanisole, and γ-terpineol) were significantly lower in diseased trees. Camphene was the only resin constituent found to differ with respect to aspect, with a higher concentration on the north aspect of check trees. There were no significant differences in carbohydrate or nitrogen content with respect to aspect. The check trees were found to have significantly higher starch, total nitrogen, and free amino-N contents than diseased trees. Trees infected with Comandra blister rust were found to contain lower levels of reducing and nonreducing sugars than the other diseased trees and the check trees. Changes in terpenoids and phenyl propanoids in trees susceptible to mountain pine beetle attack suggest a biochemical basis for host selection. Key words: mountain pine beetle, lodgepole pine, Comandra blister rust, dwarf mistletoe, Armillaria root disease, resin chemistry, susceptibility.

Flower induction and changes of phenylpropanoid content and PAL activity in cotyledons of Pharbitis nil var.Violet grown under poor nutrition.

Flower induction and changes of phenylpropanoid content and PAL activity in cotyledons of Pharbitis nil var.Violet grown under poor nutrition.

ヨウサイ (<i>Ipomoea aquatica</i> Forsk.) の低温障害発生に伴うK<sup>+</sup>漏出速度, 遊離アミノ酸含量並びにフェニルプロパノイド代謝の変化

Water convolvulus (Ipomoea aquatica Forsk.) is widely distributed as leafy vegetables in South-East Asia including southern area in Japan. It shows chilling injury manifested as browning of young leaves (2-3 immature leaves located at top part of each vine) and young stems (top part of each vine) when stored at temperatures about below 9°C. In the present study, the changes of K+ leakage, free amino acid contents, phenylpropanoid contents, and some enzyme activities relating to the biosynthesis of phenylpropanoids were inveatigated with reference to the chilling injury. The materials were sealed in polyethylene bags (0.03mm thickness) and stored at 1, 6, 9, 12, 15, 20, and 30°C.A break point of Arrhenius plot for K+leakage in young and mature leaves was found between 10 and 16°C, whereas the matured leaves showed only a little chilling-sensitivity. A marked increase of the rate of K+ leakage occurred in young leaves stored at 1°C, preceding the appearance of browning.As the contents of phenylpropanoids such as t-cinnamic, p-coumaric, caffeic and chlorogenic acids were investigated, they increased before the occurrence of chilling injury and then tended to decline almost simultaneously with the development of chilling injury. They also increased at 15°C, but the rise delayed and the extent was considerably lower than that at 1°C.Among the enzymes relating to the biosynthesis of chlorogenic acid, a main substrate of browning, hydroxycinnamoyl CoA ligase (CL) activity increased in both of 1°C and 15°C storages, then the increase was faster at 1°C reaching to a peak before the occurrence of chilling injury. Hydroxycinnamoyl CoA: quinate hydroxycinnamoyl transferase (CQT) activity showed a markedly higher increase in the 1°C storage.On the results, we present a conclusion of the low temperature induced browning mechanism as follows; exposure to low temperature leads to a rise of phenolic contents through activation of the enzymes such as CL and CQT. The accumulated phenolics induce the browning after its enzymic oxidation.