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.     

“Quinone Millipedes” Reconsidered: Evidence for a Mosaic-Like Taxonomic Distribution of Phenol-Based Secretions across the Julidae

The defensive chemistry of juliformian millipedes is characterized mainly by benzoquinones (”quinone millipedes”), whereas the secretions of the putative close outgroup Callipodida are considered to be exclusively phenolic. We conducted a chemical screening of julid secretions for phenolic content. Most species from tribes Cylindroiulini (15 species examined), Brachyiulini (5 species examined), Leptoiulini (15 species examined), Uncigerini (2 species examined), Pachyiulini (3 species examined), and Ommatoiulini (2 species examined) had non-phenolic, in most cases exclusively benzoquinonic secretions. In contrast, tribes Cylindroiulini, Brachyiulini, and Leptoiulini also contained representatives with predominantly phenol-based exudates. In detail, p-cresol was a major compound in the secretions of the cylindroiulines Styrioiulus pelidnus and S. styricus (p-cresol content 93 %) and an undetermined Cylindroiulus species (p-cresol content 51 %), in the brachyiulines Brachyiulus lusitanus (p-cresol content 21 %) and Megaphyllum fagorum (p-cresol content 92 %), as well as in an undescribed Typhloiulus species (p-cresol content 32 %, Leptoiulini). In all species, p-cresol was accompanied by small amounts of phenol. The secretion of M. fagorum was exclusively phenolic, whereas phenols were accompanied by benzoquinones in all other species. This is the first incidence of clearly phenol-dominated secretions in the Julidae. We hypothesize a shared biosynthetic route to phenols and benzoquinones, with benzoquinones being produced from phenolic precursors. The patchy taxonomic distribution of phenols documented herein supports multiple independent regression events in a common pathway of benzoquinone synthesis rather than multiple independent incidences of phenol biosynthesis.     

Effects of mixtures of phenolic acids on leaf area expansion of cucumber seedlings grown in different pH portsmouth A1 soil materials

Cucumber seedlings growing in A₁horizon Portsmouth soil material adjusted to pH 5.2, 6.0, or 6.9 were treated with 0, 0.25 or 0.5, mol/ g soil ferulic acid,p-coumaric acid, vanillic acid, or an equal mixture (0.5 mol/g total) of two acids every other day. A total of five treatments was given starting with day 7 from seeding. Absolute rates of leaf expansion were determined for seedlings. The experiment was terminated when seedlings were 17 days old. All three phenolic acids inhibited leaf expansion. The dose required for 50% inhibition of absolute rates of leaf expansion increased as pH of the soil systems increased. The order of toxicity based on 50% dose and relative potency were as follows: ferulic acid > vanillic acid =p-coumaric acid. Effects of mixtures of phenolic acids on absolute rates of leaf expansion, when compared to the effects of individual phenolic acids, were found to be antagonistic for the ferulic-vanillic acid mixture and the ferulic-p-coumaric acid mixture in the pH 5.2 soil systems. Several phenolic acid treatments were required before antagonistic effects of mixtures were evident. In all other instances, when treatment effects were significant, the effects of individual phenolic acids were additive.Paper No. 11875 of the Journal Series of the North Carolina Agricultural Research Service, Raleigh, North Carolina 27695-7601. The use of trade names in this publication does not imply endorsement by North Carolina Agricultural Research Service of the product named, nor criticism of similar products not mentioned. This research was partially supported by US-Spain Joint Committee for Scientific and Technological Corporation project CCA-8309/166.     

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 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.     

Antioxidant and Biological Activities of Novel Structured Monoacylglycerol Derivatives with Phenolic Acids

Novel structured monoacylglycerol (MAG)-based phenolic lipids are synthesized from11-bromoundecanoic acid, phenolic acids, and solketal. Selected phenolic acids namely 4-hydroxy benzoic, vanillic, syringic, cinnamic, p-coumaric, sinapic, 4-fluorocinnamic, 4-hydroxyphenyl acetic acid, 3-(4-hydroxyphenyl) propanoic and dihydrocaffeic acids are employed for the synthesis of ten novel MAG-based phenolic lipids. The synthesized phenolic lipids are characterized by FT-IR, NMR, and mass spectra analysis. All the compounds are evaluated for antioxidant, antimicrobial, and cytotoxic activities. MAG derivative 8g of sinapic acid exhibits excellent antioxidant activity in both DPPH assay and inhibition of lipid oxidation assay. MAG derivative 8f bearing p-coumaric acid shows good antimicrobial activity against both Gram-positive and Gram-negative bacterial strains with a minimum inhibitory concentration (MIC) value of 6.25 µm mL⁻¹. All the synthesized compounds are found to exhibit cytotoxicity against B16, DU145, and CHO cell lines, while sinapic and p-coumaric acid derivatives exhibit better activities compared to other derivatives.     

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.     

Essential fatty acid contents of various fats: Interpretations of values by physico-chemical tests

Biological assays of oil and fat products, free from isomers of the naturally-occurringcis-9,cis-12 linoleic acid, have been shown to provide estimates of essential fatty acid content which agree well with values obtained by spectrophoto-metric analysis. However, when partially hydrogenated fats, such as those used in margarines, are bio-assayed the estimates obtained are only about 60% of those derived by spectro-photometric tests. In a blended corn oil margarine, good agreement was obtained for linoleic acid content by using biological assay or spectrophotometry, thio-cyanometric procedure, column chromatography for saturates plus iodine value, and gas liquid partition (GLP) chromatography. This margarine fat contained about 29% of the essential form of linoleic acid, and had a ratio to saturated fatty acids of 1.6:1. The hydrogenated corn oil margarine is unlike conventional margarines in providing high amounts of the isomeric forms of linoleic acid which lack essential fatty acid activity. For this reason, poor agreement was obtained between biological assay results and those by physico-chemical measurements of linoleic acid content. Such fat contains only about 6% of the essential form of linoleic acid, with a ratio to saturated fatty acids of ca. 0.3.1. From this study it is now possible to characterize, even without bio-assay data, the fatty acid composition of a highly isomerized fat, such as is found in hydrogenated corn oil margarine. The characterization groups the fatty acids into saturates and total linoleic acids, with the latter including estimates of the positional isomers of linoleic acid with widely spaced double bonds,trans forms of linoleic acid with methylene-in-terrupted double bonds, linoleic acids with the double bonds in conjugated position, andcis-9,cis-12 linoleic acid. The combined use of the spectrophotometric and thiocyanometric procedures makes it possible to estimate the essential fatty acid content of hydrogenated fats containing residual dienes.     

Pyrolysis kinetics and product properties of softwoods,hardwoods, and the nut shell of softwood

The pyrolysis of softwoods (Pinus (P.) densiflora, P. koraiensis), hardwoods (Quercus acutissima and Liriodendron tulipifera) and nut shell of P. koraiensis was investigated using a thermogravimetric analyzer and fixed bed reactor. Thermogravimetric analysis showed that the maximum decomposition temperature of each biomass was influenced by the ash content and lignocellulosic composition of biomass. The activation energy values also varied according to the content of hemicellulose and lignin of each biomass. Large amounts of acids, such as acetic acid, were recovered from the hardwood pyrolysis reaction due to their high hemicellulose content. The nut shell of P. koraiensis and softwoods with a higher lignin content produced higher yields of phenolic compounds than the hardwoods.     

Bioactive Compounds,Antioxidant Activities and Heat Stability of Corn Oil Enriched with Tunisian Citrus aurantium L. Peel Extract

This study was designed to examine physicochemical composition, antioxidant activities and heat stability of corn oil enriched with bitter orange peel. Volatile compounds composition of corn oil flavored with Citrus aurantium peel was investigated. Flavored oil total aroma content (2.6 mg/mg oil) was mainly represented by monoterpene hydrocarbons and limonene was the major one (2.49 mg/mg oil). Flavored oil methanolic extract was characterized by total phenol content of 1.22 mg GAE/kg. Chlorogenic, ferulic and p-coumaric acids were the major phenolic components of the flavored oil extract (34.33, 30.24 and 19.39 %, respectively). It was also characterized by a higher chlorophylls and carotenoids contents than the refined one. Antioxidant activities of methanolic extracts of both samples were determined using four assays: DPPH, reducing power, β-carotene bleaching and metal chelating tests. In β-carotene bleaching and DPPH radical scavenging assays, flavored oil methanolic extract showed higher activities than the control. It was characterized by a total antioxidant activity of 4.08 mg GAE/kg and an EC₅₀ value of 3.14 mg/mg oil. Its concentration providing 50 % inhibition (IC₅₀) was 0.53 mg/mg oil in the DPPH test and 4.08 mg/mg oil in the β-carotene bleaching test. However, refined corn extract showed significantly lower antioxidant activities (p < 0.05). Results of the oxidative stability index showed bitter orange peel effectiveness against thermal oxidation based on the increased induction time observed in flavored oil (5.95).     

Attraction to Herbivore-induced Plant Volatiles by the Host-foraging Parasitoid Fly <Emphasis Type="Italic">Exorista japonica</Emphasis>

Responses of the tachinid fly Exorista japonica Townsend to odors from corn plants infested with the fly’s host, the larvae of the noctuid moth Mythimna separata (Walker), were examined in a wind tunnel. Naïve female flies showed a higher rate of landing on M. separata-infested corn plants from which the host larvae had been removed than on artificially damaged or intact corn plants. When paper impregnated with a solution of headspace volatiles collected from host-infested plants was attached to intact plants, females landed on the plants at a high rate. Females also responded to intact plants to which had been attached with paper impregnated with a synthetic blend of nine chemicals identified previously in host-infested plants. There was an optimum concentration of the synthetic blend for the females’ landing. Of the nine chemicals identified previously, four [(E)-4,8-dimethyl-1,3,7-nonatriene, indole, 3-hydroxy-2-butanone, and 2-methyl-1-propanol] released only by host-infested plants were classified as a host-induced blend. The other five [(Z)-3-hexen-1-yl acetate, (E)-2-hexenal, hexanal, (Z)-3-hexen-1-ol, and linalool] were classified as a non-specific blend released not only by infested plants but also by artificially damaged or intact plants. In the wind tunnel, E. japonica females did not respond to intact plants to which paper containing a solution of non-specific blend or host-induced blend was attached. However, they showed a high level of response to a mixture of the non-specific and host-induced blends. These results indicate that naïve E. japonica use a combination of non-specific and host-induced blends as an olfactory cue for locating host-infested plants.     

Browning-associated mechanisms of resistance to insects in corn callus tissue

Callus of the fungus- and insect-resistant corn inbred, Mp313E, of differing ages and degrees of brownness was tested for effects on neonate larvae of the corn earworm,Helicoverpa zea. Older, browner, 8-week-old callus caused significantly higher mortality ofH. zea after two days compared to larvae fed 5-week-old callus (brown or not) or pinto bean diet. Larvae fed on the 5-week-old callus were significantly smaller after nine days compared to those fed on nonbrown callus of the same age. Ferulic acid,p-coumaric acid, and sinapic acid, corn allelochemicals associated with cell walls, were oxidized (produced a brown product) up to 10-fold more rapidly by peroxidase preparations of the brown callus compared to nonbrown callus. Peroxidase isozymes from both types of brown callus separated by conventional gel electrophoresis and isoelectric focusing showed more intense anodic/acidic bands compared to peroxidase isozymes separated from the nonbrown callus. Some additional peroxidase isozymes were also present in the brown callus and were able to oxidize ferulic acid. Conventional extraction techniques for phenolic acids indicated free ferulic acid levels were similar for same-age callus, but somewhat less for older callus; no freep-coumaric acid was detected. For esterified and insoluble-bound phenolic content, the level ofp-coumaric acid was higher than that of ferulic acid and was somewhat greater in insoluble-bound fractions for the old callus compared to the younger callus. Color ratings of aqueous extracts and phenolic acid extract residues indicated much brown material remained, which was proportional in color to the original material. The differential insect response to, and peroxidase activity of, brown vs. nonbrown callus were similar to results previously noted for brown pericarps of corn compared to nonbrown pericarps. This information suggests the peroxidases are contributing to the browning through oxidation of phenolic acids and thereby enhancing resistance to insects.     

Qualitative and Quantitative Differences in Herbivore-Induced Plant Volatile Blends from Tomato Plants Infested by Either <Emphasis Type="Italic">Tuta absoluta</Emphasis> or <Emphasis Type="Italic">Bemisia tabaci</Emphasis>

Plants release a variety of volatile organic compounds that play multiple roles in the interactions with other plants and animals. Natural enemies of plant-feeding insects use these volatiles as cues to find their prey or host. Here, we report differences between the volatile blends of tomato plants infested with the whitefly Bemisia tabaci or the tomato borer Tuta absoluta. We compared the volatile emission of: (1) clean tomato plants; (2) tomato plants infested with T. absoluta larvae; and (3) tomato plants infested with B. tabaci adults, nymphs, and eggs. A total of 80 volatiles were recorded of which 10 occurred consistently only in the headspace of T. absoluta-infested plants. Many of the compounds detected in the headspace of the two herbivory treatments were emitted at different rates. Plants damaged by T. absoluta emitted at least 10 times higher levels of many compounds compared to plants damaged by B. tabaci and intact plants. The multivariate separation of T. absoluta-infested plants from those infested with B. tabaci was due largely to the chorismate-derived compounds as well as volatile metabolites of C₁₈-fatty acids and branched chain amino acids that had higher emission rates from T. absoluta-infested plants, whereas the cyclic sesquiterpenes α- and β-copaene, valencene, and aristolochene were emitted at significantly higher levels from B. tabaci-infested plants. Our findings imply that feeding by T. absoluta and B. tabaci induced emission of volatile blends that differ quantitatively and qualitatively, providing a chemical basis for the recently documented behavioral discrimination by two generalist predatory mirid species, natural enemies of T. absoluta and B. tabaci employed in biological control.     

<Emphasis Type="Italic">Sphagnum</Emphasis> Species Modulate their Phenolic Profiles and Mycorrhizal Colonization of Surrounding <Emphasis Type="Italic">Andromeda polifolia</Emphasis> along Peatland Microhabitats

Sphagnum mosses mediate long-term carbon accumulation in peatlands. Given their functional role as keystone species, it is important to consider their responses to ecological gradients and environmental changes through the production of phenolics. We compared the extent to which Sphagnum phenolic production was dependent on species, microhabitats and season, and how surrounding dwarf shrubs responded to Sphagnum phenolics. We evaluated the phenolic profiles of aqueous extracts of Sphagnum fallax and Sphagnum magellanicum over a 6-month period in two microhabitats (wet lawns versus dry hummocks) in a French peatland. Phenolic profiles of water-soluble extracts were measured by UHPLC-QTOF-MS. Andromeda polifolia mycorrhizal colonization was quantified by assessing the intensity of global root cortex colonization. Phenolic profiles of both Sphagnum mosses were species-, season- and microhabitat- dependant. Sphagnum-derived acids were the phenolics mostly recovered; relative quantities were 2.5-fold higher in S. fallax than in S. magellanicum. Microtopography and vascular plant cover strongly influenced phenolic profiles, especially for minor metabolites present in low abundance. Higher mycorrhizal colonization of A. polifolia was found in lawns as compared to hummocks. Mycorrhizal abundance, in contrast to environmental parameters, was correlated with production of minor phenolics in S. fallax. Our results highlight the close interaction between mycorrhizae such as those colonizing A. polifolia and the release of Sphagnum phenolic metabolites and suggest that Sphagnum-derived acids and minor phenolics play different roles in this interaction. This work provides new insight into the ecological role of Sphagnum phenolics by proposing a strong association with mycorrhizal colonization of shrubs.     

Identification and phytotoxic activity of compounds produced during decomposition of corn and rye residues in soil

Residues from corn and rye plants were allowed to decompose in soil for periods up to 30 days at 22–23 °C, and the identity of some of the compounds produced as well as their relative phytotoxicity to lettuce seed and seedlings were determined. Paper, thin-layer, and gas chromatography were the principal methods used to identify the various compounds formed. The identities were confirmed by comparison with known synthetic compounds. Eighteen compounds were identified in the decomposing corn residues. Of these, salicylaldehyde, and butyric, phenylacetic, and 4-phenylbutyric acids were volatile, and benzoic,p-hydroxybenzoic, vanillic, ferulic,o-coumaric,o-hydroxyphenylacetic, salicylic, syringic,p-coumaric,trans-cinnamic, and caffeic acids were not volatile. Resorcinol,p-hydroxybenzaldehyde, and phloroglucinol were also found. In the decomposing rye residues, nine compounds were identified, including vanillic, ferulic, phenylacetic, 4-phenylbutyric,p-coumaric,p-hydroxybenzoic, salicylic, ando-coumaric acids, and salicylaldehyde. In the lettuce seed bioassay, most of the above compounds from corn and rye decomposition products exhibited some phytotoxicity. Phenylacetic, 4-phenylbutyric, salicylic, benzoic, ando-hydroxyphenylacetic acids were highly inhibitory to the growth of lettuce at concentrations between 25 and 50 ppm. The others reduced growth significantly at 100 ppm. Most of the phototoxic spots were located in theR _f 0.37–0.97 zone when developed in 2% acetic acid solvent.This study was supported in part by National Research Council of Canada Grant No. A2384 to Z.A. Patrick.     

Antioxidant Activity of the Phenolic Leaf Extracts from <Emphasis Type="Italic">Monechma ciliatum</Emphasis> in Stabilization of Corn Oil

The total phenolic content and the antioxidant potential of methanolic extract (ME), ethyl acetate extract (EAE), and hexane extract (HE) from Monechma ciliatum leaves (MCL) were evaluated. The Folin-Ciocalteu, β-carotene bleaching, the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and the accelerated oxidation methods were used for evaluation. Both the extraction yield and the antioxidant activity (AOA) were strongly dependent on the solvent. Among the extracts, ME exhibited highest total phenolic compounds (TPC) and IC₅₀ values for DPPH, followed by EAE and HE, respectively. Peroxide value (PV), anisidine value (AV) conjugated dienes (CD), and thiobarbituric acid reactive substances (TBARS) were taken as the parameters for evaluation of stabilization efficacy of MCL extracts and results revealed MCL to be a potent antioxidant for the stabilization of corn oil. As a general trend, increased AOA was observed for increased extract concentration. The predominant phenolic compounds identified by HPLC-DAD in MCL extracts were p-coumaric acid, vanillin and ferulic acid.     

Changes in Lipid Composition During Dry Grind Ethanol Processing of Corn

During the dry grind ethanol process, ground corn is fermented and the major co-product is a feed called distillers dried grains with solubles (DDGS). This study investigated the changes that occur in the composition of corn oil that can be extracted from various process fractions during the dry grind ethanol process. In the first part of this study, samples of distillers dried grains, thin stillage, condensed distillers solubles (also known as syrup), and DDGS were obtained from 7 dry grind ethanol plants. The levels of deleterious free fatty acids were high (>7%) and those of valuable total phytosterols were also high in all fractions (>2%). In the second part of this study, changes in the content and composition of the fatty acids, phytosterols, tocopherols and tocotrienols were quantitatively analyzed in crude oil samples extracted from nine dry grind process fractions from three commercial ethanol plants. Fatty acid and phytosterol composition remained nearly constant in all nine fractions, although some significant variations in phytosterol composition existed among the fractions. Examination of the tocopherols and tocotrienols revealed that γ-tocopherol was the most abundant tocol in ground corn but an unknown tocol became the predominant tocol after fermentation and persisted in the remaining processing fractions and in the final DDGS product. Overall, the remaining majority of tocols remained relatively unchanged.     

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.     

Effect of lipid unsaturation on the antioxidative activity of some phenolic acids

Antioxidative properties ofp-hydroxybenzoic, vanillic, syringic, 3,4-dihydroxybenzoic,p-coumaric, ferulic, sinapic and caffeic acids were studied in the concentration range 0.02–0.20 wt% during autoxidation at 100°C of lard and sunflower oil methyl esters (MEL and MESO, respectively). In both lipid systems, the derivatives of benzoic acid had weaker inhibiting properties than did the corresponding analogues of cinnamic acid. The effectiveness and strength of the antioxidative action were considerably lower in the lipid system MESO, which was rich in linoleic acid and was more easily oxidized. Thep-hydroxybenzoic, vanillic, syringic andp-coumaric acids in this system exercised no inhibiting effect. We established that the molecules of the investigated phenolic acids initiated the chain radical process of autoxidation, and the formed antioxidant radicals propagated the chains as a result of the reaction with the lipid substrate. These reactions proceeded at a higher rate in MESO than in MEL.