Interactions oftrans-cinnamic acid,its related phenolic allelochemicals,and abscisic acid in seedling growth and seed germination of lettuce

Phenolic compounds have been identified as the most common allelochemicals produced by higher plants. Inhibitions of cinnamic acid, its related phenolic derivatives, and abscisic acid (ABA) on seedling growth and seed germination of lettuce were studied.trans-Cinnamic acid, ando-,m-, andp-coumaric acids inhibited the growth of etiolated seedlings of lettuce at concentrations higher than 10^–4 M and seed germination above 10^–3 M. Coumarin inhibited seedling growth and seed germination at 10^–5 M or above. Chlorogenic acid inhibited seedling growth above 10^–4 M, but did not inhibit seed germination at 10^–5–5×10^–3 M. Low concentrations (below 10^–3 M) of caffeic and ferulic acids promoted the elongation of hypocotyls, but higher concentrations (over 10^–3 M) inhibited seedling growth and seed germination. These phenolic compounds and abscisic acid had additive inhibitory effects both on seedling growth and seed germination. The inhibition on lettuce was reversed by caffeic and ferulic acids at concentrations lower than 10^–3 M except for the inhibition of germination by coumarin. These results suggest that in naturetrans-cinnamic acid,o-, m-, p-coumaric acids, coumarin, and chlorogenic acid inhibit plant growth regardless of their concentration. However, caffeic and ferulic acids can either promote or inhibit plant growth according to their concentration.     

Effects of ferulic andp-coumaric acids in nutrient culture of cucumber leaf expansion as influenced by pH

Cucumber seedlings were grown in 5 mM MES [2-(N-morpholino)ethanesulfonic acid] -buffered nutrient solutions adjusted to a pH of 5.5, 6.25, or 7.0. Nutrient solutions were changed on alternate days. Seedlings were treated for a two-day period with various concentrations (0–1 mM) of ferulic acid,p-coumaric acid, or mixtures of these phenolic acids when 16 days old. Leaf growth, dry weight, and water utilization of the seedlings; pH of the solutions; and disappearance of the phenolic acids from nutrient solutions were monitored. Leaf area expansion of cucumber seedlings was inhibited by both ferulic andp-coumaric acid, and the magnitude of these inhibitions was influenced by concentration and pH. Inhibition of leaf area expansion was greater at pH 5.5 and nominal at pH 7.O. Ferulic acid was more inhibitory thanp-coumaric acid. The effect of pH on growth was best described by data for mean relative rates of leaf expansion. For example, the mean relative rates of leaf expansion by both acids at 0.5 mM for the 16- to 18-day growth period (treatment period) were reduced by 45, 31, and 8% for the pH 5.5, 6.25, and 7.0 treatments, respectively. The dry weight of seedlings at harvest (day 22) was significantly reduced for seedlings grown in the pH 5.5 and 6.25 treatments, but not for the pH 7.0 treatment. There was, however, one exception; the dry weight of seedlings treated withp-coumaric acid solutions adjusted to a pH of 5.5 was not significantly reduced. Water utilization by the seedlings was reduced by both ferulic andp-coumaric acid. Again, the impact of ferulic acid was greater thanp-coumaric acid. The effect of ferulic acid on water utlization decreased with increasing pH of the nutrient solution. The pH effects were not so consistent forp-coumaric acid. The effects of equimolar mixtures of the two phenolic acids were additive for all variables measured. There was a linear correlation between mean relative rates of leaf expansion and water utilization.Paper No. 9693 of the Journal Series of the North Carolina Agricultural Research Sevice, Raleigh, North Carolina. Mention of a trademark or a propriety product does not constitute a guarantee or warranty of the product by the Agricultural Research Service and does not imply its approval to the exclusion of other products that may be suitable.     

Effects of mixtures of phenolic acids on phosphorus uptake by cucumber seedlings

To determine how individual phenolic acids in a mixture might affect phosphorus (P) uptake, 15-day-old cucumber seedlings grown in solution culture were treated with ferulic, vanillic,p-coumaric, or equimolar mixtures of these phenolic acids. Phenolic acid and P uptake were determined by solution depletion. The joint action of the mixtures of these phenolic acids on P uptake was primarily additive. Thus, as the number of phenolic acids increased in the mixture, the concentrations of the individual phenolic acids in the mixture required to bring about a given response declined. Seedling uptake of individual phenolic acids from solution mixtures of phenolic acids was reduced when compared to the uptake of phenolic acids from single phenolic acid solutions. The magnitude of the reduction varied with phenolic acid and concentration. The dose required for 50% inhibition of P uptake was approximately two to three times higher for vanillic acid (6.73 mM) than for ferulic (2.27 mM) andp-coumaric acids (3.00 mM) when dose was based on the initial treatment concentrations. The dose required for 50% inhibition of P uptake was not significantly different for the three phenolic acids (42 ± 5 mol/g root fresh weight) when dose was based on phenolic acid uptake. Potential reasons for these differences are discussed.Paper No. 12527 of the Journal Series of the North Carolina Agricultural Research Service, Raleigh, North Carolina 27695-7643. The use of trade names in this publication does not imply endorsement by the North Carolina Agricultural Research Service of products named, nor criticism of similar ones not mentioned. This research was partially supported by the US-Spain Joint Committee for Scientific and Technological Cooperation project CCA-8309/166.     

Simultaneous effects of ferulic andp-coumaric acids on cucumber leaf expansion in split-root experiments

Experiments were conducted to determine how plant responses to mixtures of allelochemicals may change as the proportion of roots in contact with allelochemicals is modified. Thirteen-day-old cucumber seedlings were treated with ferulic and/orp-coumaric acid in a split-root nutrient culture system. Leaf areas were determined just prior to treatment and at harvest, 24 hr after treatment. Ferulic acid was more inhibitory to cucumber leaf expansion thanp-coumaric acid. The effects of ferulic andp-coumaric acids on leaf expansion were additive. For individual acids, mixtures of ferulic andp-coumaric acids in the same container and combinations of ferulic andp-coumaric acids in separate containers, the inhibition of leaf expansion was directly related to the product of the concentration of the acid(s) and the proportion of roots treated with the acid(s). Pretreatment with 0.2 or 0.4 mM ferulic acid and subsequent treatment with 0.5 mM ferulic acid failed to show evidence of acclimation by cucumber seedlings.The use of trade names in this publication does not imply endorsement by the North Carolina Agricultural Research Service of products named, nor criticism of similar ones not mentioned.     

Induction of Phenolic Compounds in Two Cultivars of Cucumber by Treatment of Healthy and Powdery Mildew-infected Plants with Extracts of Reynoutria sachalinensis

Accumulation of phenolic compounds (p-coumaric, caffeic, and ferulic acids and p-coumaric acid methyl ester) was followed in susceptible (Mustang) and tolerant (Flamingo) cucumber (Cucumis sativus) cultivars. The objective was to determine whether these compounds played a role in resistance against powdery mildew following a prophylactic treatment with Milsana (leaf extracts from the giant knot weed Reynoutria sachalinensis, polygonaceae). This treatment significantly reduced the incidence of powdery mildew in both cultivars. Phenolic compounds were extracted from leaves. In the hydrolyzed fraction containing phenolic aglycones, levels of p-coumaric, caffeic, and ferulic acids and of p-coumaric acid methyl ester increased in all treatments (with leaf extracts of R. Sachalinensis, powdery mildew, or both) except the control, one or two days after treatment. In the fraction containing free phenolics, from the tested compounds, only ferulic acid showed an increase in cv. Flamingo (tolerant), and was particularly evident following treatments. On the other hand, the amounts of hydroxycinnamic acids increased rapidly in the two cultivars following Milsana treatment, suggesting their role in disease reduction. All compounds showed antifungal activity when tetsed against common pathogens of cucumber (Botrytis cinerea, Pythium ultimum, and P. aphanidermatum), but in general methyl esters were more fungitoxic than their corresponding free acids. This study suggests that cucumber is able to release antifungal compounds that are instrumental in repressing powdery mildew infection. This response is seemingly independent from the level of genetic resistance associated with each cultivar.     

Species-specific composition of free amino acids on the leaf surface of fourSenecio species

The specificity of the chemical composition of the leaf surface of fourSenecio species was studied in order to understand the host selection ofTyria jacobaeae, a monophagous moth that hasSenecio jacobaea as its principal host plant. Pyrrolizidine alkaloids characteristic forSenecio species were not detected in water and sulfuric acid extracts of the leaf surface ofSenecio jacobaea. Water extracts of the leaf surfaces ofS. jacobaea, S. vulgaris, S. viscosus, andS. sylvaticus contained low concentrations of free amino acids. The proportions of these amino acids were very different from those inside the leaf tissues. In a discriminant analysis, the four species could be completely separated on the basis of the relative proportions of amino acids on the leaf surface.     

Effects of mixtures of four phenolic acids on leaf area expansion of cucumber seedlings grown in Portsmouth B1 soil materials

Cucumber seedlings growing in a 12 mixture of soil (Portsmouth B₁) and sand adjusted to pH 5.2 were treated every other day five times with 0, 0.0625, 0.125, 0.25, or 0.5 mol/g soil of ferulic, caffeic,p-coumaric,p-hydroxybenzoic, protocatechuic, sinapic, syringic, or vanillic acids. Treatments began when seedlings were 8 days old. The effects on mean absolute rates of leaf expansion were used to estimate the relative potencies of these phenolic acids to ferulic acid. Based on the results of this experiment, ferulic,p-coumaric,p-hydroxybenzoic, and vanillic acids were chosen for further study. Materials and procedures were identical in the second study, but treatments consisted of mixtures of the four phenolic acids at concentration combinations designed to achieve 40 % or 60 % inhibition of absolute rates of leaf expansion. Using joint action analysis, a model describing the action of the phenolic acid mixtures was developed. A model involving only two factor terms was sufficient to describe the observed responses of cucumber leaf area to the phenolic acid mixtures. The action ofp-hydroxybenzoic acid on absolute rates of leaf expansion was inhibited by the presence of the other three phenolic acids. No other antagonisms or synergisms existed among the four compounds.This research was partially supported by the North Carolina Agricultural Research Service, Raleigh, North Carolina 27695-7643 and by the US-Spain Joint Committee for Scientific and Technological Cooperation project CCA-8309/166.     

Phenolic acids affect photosynthesis and protein synthesis by isolated leaf cells of velvet-leaf

The effects ofp-coumaric, ferulic, chlorogenic, and vanillic acids on photosynthesis and protein synthesis by isolated leaf cells of velvetleaf (Abutilon theophrasti Medik) were investigated. Photosynthesis and protein synthesis were measured in cell suspensions by the incorporation of¹⁴CO₂ and [¹⁴C]leucine, respectively. None of the tested phenolic acids except vanillic reduced photosynthesis by more than 50% at the highest concentration and 30 min of incubation. At 100M concentrations and 60-min incubation periods,p-coumaric, ferulic, chlorogenic, and vanillic acids inhibited photosynthesis by 33, 37, 57, and 65%, respectively. Ferulic acid was the most inhibitory to protein synthesis and reduced the incorporation of [¹⁴C]leucine by 50% at about 1.0M after 60 min of incubation. At the highest concentrations tested in this study, vanillic and ferulic acids were inhibitory to photosynthesis and protein synthesis, respectively, whereas chlorogenic andp-coumaric acids did not inhibit either physiological process. The maximum inhibition of protein synthesis by chlorogenic acid was 19% and by vanillic acid was 28% at 100M concentrations. Chlorogenic, vanillic, andp-cou-maric acids at 0.1M caused increased protein synthesis over the untreated control. Overall, photosynthesis was more sensitive than protein synthesis to the four phenolic acids tested.Florida Agricultural Experiment Station Journal Series No. 9228.     

Allelopathy in agroecosystems: Wheat phytotoxicity and its possible roles in crop rotation

The germination rates of cotton and wheat seeds were significantly affected by various extracts of wheat mulch and soils collected from the wheat field. This toxicity was even more pronounced against seedling growth. Five allelochemics: ferulic,p-coumaric,p-OH benzoic, syringic, and vanillic acids, were identified from the wheat mulch and its associated soil. Quantitatively, ferulic acid was found at higher concentrations thanp-coumaric acid in the soil. Various concentrations of ferulic andp-coumaric acids were toxic to the growth of radish in a bioassay. The functional aspects of allelochemic transfer from decaying residue to soil and the subsequent microbial degradation within agroecosystems are discussed, particularly as they relate to wheat crop rotation, with wheat and cotton, in Pakistan.     

Microbial decomposition of ferulic acid in soil

The suppression of plant growth by different phenolic acids is well known. This work was designed to determine if ferulic acid, a known phenolic inhibitor of plant growth, accumulates in the soil and if soil microorganisms could be isolated that metabolize it. Over 99% of the extractable ferulic acid was lost from decaying hackberry leaves in 300 days. During this time the amount in the top 15 cm of soil remained fairly constant at about 30 ppm, except for the March sample which was significantly higher than the rest. Addition of ferulic acid to soil caused an increase in CO₂ evolution and in numbers of a select group of microorganisms.Rhodotorula rubra andCepnalosporium curtipes, which actively metabolize ferulic acid, were isolated, but the metabolic pathways employed appear to be different from the reported one. The reported pathway for ferulic acid breakdown is ferulic acid to vanillic acid to protocatechuic acid to -keto-adipic acid.Rhodotorula Rubra was found to convert ferulic acid to vanillic acid, but no evidence was found for utilization of the rest of the pathway.Cephalosporium curtipes appears to use a different pathway or to metabolize intermediate compounds rapidly without accumulating them, because no phenolic compounds were found during the breakdown of ferulic acid. The presence in the soil of microorganisms that metabolize ferulic acid and other phenolic acids is ecologically significant because such organisms prevent long-term accumulations of these substances, which are toxic to many other microorganisms and higher plants.     

Allelopathic potential in bilberry-spruce forests: Influence of phenolic compounds on spruce seedlings

Regeneration failure ofPicea abies in a subalpine bilberry-spruce forest was studied in relation to phenolic compounds, their occurrence and toxicity. Germination bioassays with natural leachates of bilberry (Vaccinium myrtillus) and spruce showed negative effects on root elongation of spruce seedlings. Growth bioassays on litter and humus demonstrated inhibitory effects of these organic layers.p-Hydroxyacetophenone, a spruce-specific metabolite, was isolated in spruce throughfall (10^–6 M), in water extracts of litter (between 1 and 8 µg/g dry wt) and organic layer (less than 1 µg/g dry wt) in addition to tannins and several common phenolic acids. Potential relationships between vegetation cover and phenolic pattern of the soil are discussed, since organic layers under bilberry heath exhibited higher amounts of phenolic acids and tannins than those under spruce.p-Hydroxyacetophenone and caffeic acid reduced, even at 5 × 10^–5 M, spruce seedling growth, especially root development, with additive effects for these two monomers. Autotoxicity involving spruce trees and allelopathy of understory species, mediated byp-hydroxy-acetophenone and other phenolic compounds, including tannins, deserves further attention in regeneration studies.     

Allelopathic effect of phenolic acids from humic solutions on two spruce mycorrhizal fungi:Cenococcum graniforme andLaccaria laccata

The aim of this investigation was to determine the impact ofp-hydroxyacetophenone,p-hydroxybenzoic acid, catechol, and protocatechuic acid on respiration of two spruce mycorrhizal fungi:Laccaria laccata andCenococcum graniforme. These phenols are produced byVaccinium myrtillus,Athyrium filixfemina, andPicea abies, predominant species of spruce forests in the Alps, and they are also present in humic solutions at 10^–10 M or 10^–5 M. Respiration of the two fungi was inhibited by the four phenolic acids, even at concentrations ranging from 10^–5 M to 10^–7 M. These data show phenolic acids from humic solutions have biological activity at extremely low concentrations, suggesting a contribution ofV. myrtillus, A. filixfemina, andP. abies to allelopathic inhibition of mycorrhizal fungi.     

Effects of Microbial Utilization of Phenolic Acids and their Phenolic Acid Breakdown Products on Allelopathic Interactions

Reversible sorption of phenolic acids by soils may provide some protection to phenolic acids from microbial degradation. In the absence of microbes, reversible sorption 35 days after addition of 0.5–3 mol/g of ferulic acid or p-coumaric acid was 8–14% in Cecil A_p horizon and 31–38% in Cecil B_t, horizon soil materials. The reversibly sorbed/solution ratios (r/s) for ferulic acid or p-coumaric acid ranged from 0.12 to 0.25 in A_p and 0.65 to 0.85 in B_t horizon soil materials. When microbes were introduced, the r/s ratio for both the A_p and B_t horizon soil materials increased over time up to 5 and 2, respectively, thereby indicating a more rapid utilization of solution phenolic acids over reversibly sorbed phenolic acids. The increase in r/s ratio and the overall microbial utilization of ferulic acid and/or p-coumaric acid were much more rapid in A_p than in B_t horizon soil materials. Reversible sorption, however, provided protection of phenolic acids from microbial utilization for only very short periods of time. Differential soil fixation, microbial production of benzoic acids (e.g., vanillic acid and p-hydroxybenzoic acid) from cinnamic acids (e.g., ferulic acid and p-coumaric acid, respectively), and the subsequent differential utilization of cinnamic and benzoic acids by soil microbes indicated that these processes can substantially influence the magnitude and duration of the phytoxicity of individual phenolic acids.     

Phenolic acid content of soils from wheat-no till,wheat-conventional till,and fallow-conventional till soybean cropping systems

Soil core (0–2.5 and/or 0–10 cm) samples were taken from wheat no till, wheat-conventional till, and fallow-conventional till soybean cropping systems from July to October of 1989 and extracted with water in an autoclave. The soil extracts were analyzed for seven common phenolic acids (p-coumaric, vanillic,p-hydroxybenzoic, syringic, caffeic, ferulic, and sinapic; in order of importance) by high-performance liquid chromatography. The highest concentration observed was 4 g/g soil forp-coumaric acid. Folin & Ciocalteu's phenol reagent was used to determine total phenolic acid content. Total phenolic acid content of 0- to 2.5-cm core samples was approximately 34% higher than that of the 0- to 10-cm core samples. Phenolic acid content of 0- to 2.5-cm core samples from wheat-no till systems was significantly higher than those from all other cropping systems. Individual phenolic acids and total phenolic acid content of soils were highly correlated. The last two observations were confirmed by principal component analysis. The concentrations were confirmed by principal component analysis, tions of individual phenolic acids extracted from soil samples were related to soil pH, water content of soil samples, total soil carbon, and total soil nitrogen. Indirect evidence suggested that phenolic acids recovered by the water-autoclave procedure used came primarily from bound forms in the soil samples.The use of trade names in this publication does not imply endorsement by the North Carolina Agricultural Research Service of products named, nor criticism of similar ones not mentioned.     

Effects of various mixtures of ferulic acid and some of its microbial metabolic products on cucumber leaf expansion and dry matter in nutrient culture

Cucumber seedlings (Cucumis sativus cv. Early Green Cluster) ranging from 6 to 16 days of age were treated with various concentrations (0– 1 mM) of caffeic, ferulic,p-coumaric,p-hydroxybenzoic, protocatechuic, sinapic, syringic, and vanillic acids and mixtures of ferulic acid and one or two of the other phenolic acids. Seedlings were grown in full-strength Hoagland's solution which was changed every other day. Phenolic acid treatments were given with each nutrient solution change starting at day 6 or given once when seedlings were 13 or 14 days old. Leaf area, mean relative rates of leaf expansion, transpiration rates, water utilization, and the concentrations of the phenolic acids in nutrient solution were determined at one- or two-day intervals. Seedling dry weight was determined at final harvest. Seedling leaf area and dry weight were linearly related. Since leaf areas can be easily obtained without destructive sampling and leaf area expansion responds rapidly to phenolic acid treatments, it was utilized as the primary indicator of plant response. The resulting data suggested that a number of ferulic acid microbial metabolic products, as well as two other phenolic acids observed in soils (p-coumaric and syringic acid), can reduce seedling dry weight, leaf expansion, and water utilization of cucumber seedlings in a similar manner. The magnitude of impact of each of the phenolic acids, however, varied with phenolic acid and concentration. It appears that the inhibitory activity of these phenolic acids involved water relations of cucumber seedlings, since the phenolic acid treatments resulted in closure of stomata which then remained closed for several days after treatment. The data also demonstrated that the effects of mixtures of phenolic acids on cucumber seedlings may be synergistic, additive, or antagonistic. The type of response observed appeared to be related to the factor measured, the compounds in the nmixture, and the magnitued of inhibition associated with each compounds. The data also indicated that the effects of the various phenolic acids were reversible, since seedling leaf area increased rapidly once phenolic acids were removed from the root environment. Mean relative rates of leaf expansion recovered even in the presence of the various phenolic acids.Paper No. 9396 of the Journal Series of the North Carolina Agricultural Research Service. Raleigh, North Carolina. Mention of a trademark or proprietary product does not constitute a guarantee or warranty of the product by the Agricultural Research Service and does not imply its approval to the exclusion of other products that may be suitable.     

Interactions betweenKalmia and black spruce: Isolation and identification of allelopathic compounds

Aqueous extracts of fresh leaves and organic soil of northern sheep laurel (Kalmia angustifolia var.angustifolia) were found to be inhibitory to the growth of black spruce (Picea mariana) germinants. Primary root growth of black spruce was more affected by the extracts than was shoot growth. The growth inhibition caused by the leaf extract was most pronounced under acidic conditions (pH 3–4). The aqueous extract ofKalmia leaves contained ferulic, vanillic, syringic, gentisic,m-coumaric,p-coumaric,o-hydroxyphenylacetic, andp-hydroxybenzoic acids as well as some other unknown compounds. These compounds were isolated from the aqueous extract ofKalmia leaves by ethyl acetate extraction and identified using thin-layer chromatography (TLC) and high-performance liquid chromatography (HPLC). Bioassay indicated that the overall toxicity of the phenolic compounds to black spruce appeared to increase in the order ofo-hydroxyphenylacetic,p-hydroxybenzoic, vanillic,p-coumaric, gentisic, syringic, ferulic, andm-coumaric acids.     

Selected Ectomycorrhizal Fungi of Black Spruce (Picea mariana) can Detoxify Phenolic Compounds of Kalmia angustifolia

Allelopathy has been implicated as a factor contributing toward failure of black spruce (Picea mariana) regeneration in Kalmia angustifolia-dominated sites in eastern Canada. Several phenolic acids of Kalmia origin inhibit primary root growth of black spruce. We tested the hypothesis that some well-adapted conifer ectomycorrhizae can degrade and detoxify water-soluble phenolic compounds produced by Kalmia and use the degraded products as a carbon source to stimulate growth. We found that hyphal growth of Paxillus involutus, a common ectomycorrhizal fungus of black spruce, was stimulated by water leachates of Kalmia leaf and litter. An equimolar mixture of three phenolic acids (ferulic, o-coumaric, and o-hydroxyphenylacetic acid), commonly found in Kalmia, had no negative effects on fungal growth at 1 mM concentration. The o-hydroxyphenylacetic (o-HPA) acid, which is known to be toxic to black spruce, was found to stimulate the growth of Laccaria laccata, L. bicolor, and P. involutus (isolates 211804 and 196554) by 38.4, 29.3, 25.0, and 18.9%, respectively, at 1 mM. Pure ferulic, o-coumaric, and o-HPA acids were degraded by 100, 98, and 79.5%, respectively, within 10 d in the presence of P. involutus 211804. However, L. laccata could not tolerate high concentrations of the Kalmia leachates. P. involutus and L. bicolor used o-HPA acid as a carbon source when cultured in noncarbon nutrient medium. The 0.5 and 0.2 mM o-HPA acid inhibited the root growth of black spruce. However, after solutions had been exposed to a culture of P. involutus, they had no significant effect on seedling growth of black spruce. We concluded that some ectomycorrhizal fungi, such as P. involutus and L. bicolor, are able to degrade Kalmia phenolics. Our findings point to a mechanism by which ectomycorrhizal species can control species interactions in higher plants by changing the rhizosphere chemistry.     

Primary Metabolites and Polyphenols in Rapeseed (Brassica napus L.) Cultivars in China

Defatted meals of 10 rapeseed (Brassica napus L.) varieties were investigated for their total phenolic, phenolic acid (free, esterified, and insoluble-bound forms), and tannin contents. The antioxidant capacities (AC) of methanol extracts from samples were assessed using the 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH•), Folin–Ciocalteu method and ferric reducing antioxidant power (FRAP), and β-carotene–linoleic acid tests. In the fraction of free phenolic acids, sinapic, caffeic, ferulic, syringic, gallic, and p-coumaric acids were identified. In the fraction of esterified phenolic acids, sinapine, sinapoyl glucoside, and disinapoyl gentiobiose were identified. After basic hydrolysis, sinapic, ferulic, cinnamic, and 4-hydroxybenzoic acids were identified, and sinapic acid (SA) constituted 98.3% to 99.6% of the total esterified phenolic acids. Eleven components (sinapic, protocatechuic, p-coumaric, syringic, vanillic, gallic, caffeic, ferulic, salicylic, cinnamic, and 4-hydroxybenzoic acids) in the fraction of insoluble-bound phenolic acids were identified. The AC of the samples correlated with the total phenolic content. Overall, the total phenolics showed a better correlation with AC than the individual phenolic compounds. Moreover, SA, sinapoyl glucoside, and disinapoyl gentiobiose showed a highly significant and strong positive correlation with the AC of rapeseed meals, and the derivatives of cinnamic acid showed a higher correlation with AC than the derivatives of benzoic acid. The change in the canolol content in rapeseeds under microwave irradiation is discussed. The correlation of the canolol formed with SA and its derivatives is discussed.     

Evaluation of Ferulic Acid Uptake as a Measurement of Allelochemical Dose: Effective Concentration

Soil solution concentrations of allelopathic agents (e.g., phenolic acids) estimated by soil extractions differ with extraction procedure and the activities of the various soil sinks (e.g., microbes, clays, organic matter). This led to the hypothesis that root uptake of phenolic acids is a better estimator of dose than soil solution concentrations based on soil extracts. This hypothesis was tested by determining the inhibition of net phosphorus uptake of cucumber seedlings treated for 5 hr with ferulic acid in whole-root and split-root nutrient culture systems. Experiments were conducted with 11 ferulic acid concentrations ranging from 0 to 1 mM, phosphorus concentrations of 0.25, 0.5, or 1 mM, and solution pH values of 4.5, 5.5, or 6.5 applied when cucumber seedlings were 9, 12, or 15 days old. The uptake or initial solution concentration of ferulic acid was regressed on ferulic acid inhibition of net phosphorus uptake. Attempts were made to design experiments that would break the collinearity between ferulic acid uptake and phosphorus uptake. The original hypothesis was rejected because the initial ferulic acid solution concentrations surrounding seedling roots were more frequently and consistently related to the inhibition of net phosphorus uptake than to ferulic acid uptake by these roots. The data suggest that root contact, not uptake, is responsible for the inhibitory activity of phenolic acids.     

Factors contributing to resistance of exotic maize populations to maize weevil,Sitophilus zeamais

Factors contributing to resistance of maize to infestation by the corn weevilSitophilus zeamais were investigated in four populations of indigenous and improved maize from Belize. Resistance was related to the antifeedant properties of grain as well as sugar content and mechanical hardness. Grain extracts of all populations of maize significantly reduced insect feeding on treated artificial diets when compared to control diets. Consumption of treated diets was negatively correlated with phenolic content of the grain extract. An analysis by GC-MS indicated that ferulic acid andp-coumaric acid were the principal phenolics present in the extracts, and insect feeding was strongly deterred when pure substances were added to insect diets. Fluorescence associated with ferulic acid and related compounds in grain sections was located in the pericarp and aleurone layer and was especially intense in the most resistant grain variety.Contribution No. 838.