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.     

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.     

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.     

Inhibited Oxidation of Lipids II: Comparison of the Antioxidative Properties of Some Hydroxy Derivatives of Benzoic and Cinnamic Acids

The antioxidative properties of p-hydroxy-benzoic acid, vanillic acid, syringic acid, 3,4-dihydroxy-benzoic acid, p-coumaric acid, ferulic acid, sinapic acid and caffeic acid in lard autoxidation at 100°C are compared. The effect of phenolic acids is investigated within the concentration range 0.02 – 0.20 wt %. It is proved that the derivatives of the benzoic acid have weaker inhibiting properties than is the case of the corresponding analogues of the cinnamic acid due to the more active participation of the inhibitor in the elementary reactions of propagation and initiation of the radical chain process. The activity (a complex parameter demonstrating the efficiency and strength of the antioxidant) of the phenolic acids investigated decreases in the sequence: caffeic acid >3,4-dihydroxy-benzoic acid > sinapic acid > syringic acid>ferulic acid>p-coumaric acid>vanillic acid. The increase in concentration of the acids investigated is most advisable in the case of sinapic, syringic and ferulic acids which are not consumed in side reactions.     

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.     

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.     

Formation and Structure of Lignin in Monocotyledons. III. Heterogeneity of Sugarcane (Saccharum officinarum L.) Lignin with Respect to the Composition of Structural Units in Different Morphological Regions

Heterogeneity of sugarcane lignin with respect to the composition of structural units in different morphological regions was studied by microautoradiography and some degradative analyses. Structure of the lignin differs among fiber, vessel and parenchyma. The lignin in the secondary wall of fiber is composed of syringyl (S)-, guaiacyl (G)- and p-hydroxyphenyl (H)-propane units with accompanying phenolic acid residues, and the proportion of these monolignols is S > G > H. The lignin in vessels of protoxylem contains more G and H units than S units, and that in vessels of metaxylem is similar to that in fibers. Phenolic acid constituent in sugarcane cell wall includes sinapic acid in addition to p-coumaric and ferulic acids. Ferulic acid deposits at the very early stage of lignification, and p-coumaric and sinapic acids increasingly deposit with the progress of lignification. Therefore, the ratio of p-coumaric acid or sinapic acid to ferulic acid increases with lignification. Parenchyma wall involves larger amount of phenolic acids than vascular bundle does. The lignin in parenchyma is difficult to isolate by Björkman procedure, because there is greater possibility to form cross-linkage among cell wall polymers through phenolic acids. The cross linkages involving phenolic acid ester also explains why the sugarcane lignin is easily degraded.     

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.     

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 phenolic acids on germination and early growth of herbaceous woodland plants

Four herbaceous plant species from woodland (clearings),Deschampsia flexuosa, Scrophularia nodosa, Senecio sylvaticus, andChamaenerion angustifolium, were tested for their sensitivity to phenolic acids. Seven commonly occurring phenolic compounds were used in a germination experiment in concentrations ranging from 0.01 to 10 mM, i.e., salicylic,p-hydroxybenzoic, syringic, caffeic, vanillic,p-coumaric, and ferulic acids. Germination was delayed rather than inhibited. Radicle elongation was strongly affected; at lower concentrations stimulatory effects were observed, whereas at high concentrations radicle elongation was severely reduced. Salicylic acid was the most effective phenolic compound, whereas caffeic acid caused no effects. Early growth was studied in more detail in a second experiment withDeschampsia flexuosa andSenecio sylvaticus and the phenolic acids, ferulic and p-coumaric acid. Primary root length, number and length of secondary roots, and dry weight were stimulated at 0.01 mM but were inhibited at 10 mM of both compounds. The results are discussed in view of the allelopathic relations between trees and herbaceous understory vegetation.     

Use of water and EDTA extractions to estimate available (free and reversibly bound) phenolic acids in Cecil soils

Sterile and microbe reinfested Cecil A_p and B_t soil materials amended with 0 to 5 µmol/g of ferulic acid,p-coumaric acid,p-hydroxybenzoic acid, or vanillic acid were extracted after varying time intervals with water, EDTA, or NaOH to characterize sorption of cinnamic and benzoic acid derivatives and to determine the effectiveness of water and EDTA extractions in estimating concentrations of free and reversibly bound phenolic acids in soils. Basic EDTA (0.5 M, pH 8) extractions and water extractions provided good estimates of both free and reversibly bound cinnamic acid derivatives, but not of benzoic acid derivatives. Neutral EDTA (0.25 M, pH 7) and water extractions, however, were effective for both cinnamic and benzoic acid derivatives Rapid initial sorption of both cinnamic and benzoic acid derivatives was followed by slow long-term sorption of the cinnamic acid derivatives. Slow long-term sorption was not observed for the benzoic acid derivatives. The amount of sorption of phenolic acids in soil materials was directly related to the concentration of phenolic acids added to soil materials. The addition of a second phenolic acid to the soil materials did not substantially affect the sorption of each individual phenolic acid. Sodium hydroxide extractions, which were made only after phenolic acids in phenolic acid-amended and non-amended soil material were depleted by microbes, confirmed that neutral EDTA and water extractions of soils can be used to make accurate estimates of baseline (residual) levels of free and reversibly bound phenolic acids available to soil microbes and, thus, potentially to seeds and roots.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.     

How Do Phenolic Acids Change the Secondary and Tertiary Structure of Gliadin? Studies with an Application of Spectroscopic Techniques

The effect of the chemical structure of selected phenolic acids on the molecular organization of gliadins was investigated with the application of Fourier Transform Infrared (FTIR) technique, steady-state, and time-resolved fluorescence spectroscopy. Hydroxybenzoic (4-hydroxybenzoic, protocatechuic, vanillic, and syringic) and hydroxycinnamic (coumaric, caffeic, ferulic, sinapic) acids have been used as gliadins modifiers. The results indicated that hydroxybenzoic acids due to their smaller size incorporate into spaces between two polypeptide chains and form a hydrogen bond with them leading to aggregation. Additionally, syringic acids could incorporate into hydrophobic pockets of protein. Whereas hydroxycinnamic acids, due to their higher stiffness and larger size, separated polypeptide chains leading to gliadin disaggregation. These acids did not incorporate into hydrophobic pockets.     

Relationships between Phenolic Acid Concentrations,Transpiration, Water Utilization,Leaf Area Expansion,and Uptake of Phenolic Acids: Nutrient Culture Studies

Phenolic acid treatments of cucumber seedlings (Cucumis sativus cv “Early Green Cluster”) inhibited transpiration, water utilization, leaf area, and absolute and relative rates of leaf expansion. The cinnamic acids, ferulic and p-coumaric acids, were two to five times more inhibitory than the benzoic acids, p-hydroxybenzoic acid and vanillic acid. When phenolic acid concentrations were maintained at inhibitory concentrations through multiple successive treatments, percent inhibition of water utilization remained relatively constant for a given concentration and phenolic acid, percent inhibition of leaf area initially increased and then leveled off to a constant percent, and percent inhibition of transpiration and rates of leaf area expansion declined over time. Subsequently, p-coumaric acid was chosen as the model compound for further study. When p-coumaric acid was inhibitory, percent inhibition of transpiration, water utilization, and rates of leaf area expansion of actively growing leaves rapidly declined (i.e., was lost) as p-coumaric acid concentrations surrounding roots decreased. Absolute and relative rates of leaf expansion, for example, declined approximately 12 and 14%, respectively, for every 0.1 mM decline in p-coumaric acid concentration. Uptake of p-coumaric acid by cucumber seedling roots was continuous over the 24- or 36-hr periods monitored, but was not consistently related to the initial p-coumaric acid treatment concentrations. However, declining p-coumaric acid concentrations monitored at 6- or 12-hr intervals over the 24- or 36-hr periods continued to be highly correlated to the initial p-coumaric acid treatment concentrations. A 25% depletion by 13-d-old cucumber seedlings took 8.5, 12, 19.5, 25, and 29.5 hr for 0.125-, 0.25-, 0.5-, 0.75-, and 1-mM treatments, respectively. Uptake during periods when phenolic acid concentrations and root uptake (depletion from solution) were related appeared to represent periods dominated by apoplastic movement into the intercellular spaces of roots. Uptake during periods without this relationship likely represented periods dominated by symplastic movement. The ability of cucumber seedlings to modify active phenolic acid concentrations surrounding their roots suggests that cucumber seedling can directly influence the magnitude of primary and secondary effects of phenolic acids through feedback regulation.     

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.     

Improvement of quality and antioxidant properties of dried mulberry leaves with combined far-infrared radiation and air convection in Thai tea process

Combined far-infrared radiation with hot-air convection (FIR-HA) drying was used for improving colour and antioxidant properties of mulberry leaf tea. Antioxidant properties and phenolic compounds of FIR-HA dried mulberry tea were determined and compared with the commercial product and with fresh leaves. We found that a smaller decrease in L and b values of the FIR-HA dried tea than those of commercial tea was observed. FIR-HA tea was found to have similar colour to fresh leaf while the commercial tea had darker colour. A significant decrease in total phenolic acid content (TPC) and total flavonoid content (TFC) was found in hot-air (HA) dried commercial tea compared to fresh leaves, while TPC in FIR-HA dried tea was significantly increased. Similar results were found in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical activities. However, the results were different for ferric reducing antioxidant power (FRAP). Both teas had lower FRAP values compared to fresh leaves. Eleven phenolic compounds were identified in fresh leaf and in mulberry tea, namely p-coumaric acid, benzoic acid, (+)-catechin, chlorogenic acid, vanillic acid, syringic acid, sinapic acid, protocatechuic acid, ferulic acid, gallic acid and caffeic acid. The total content of phenolic compounds (TPCC) increased in FIR-HA dried samples compared to those of HA dried tea, except for chlorogenic and syringic acids, which were found in greater amounts in HA dried commercial tea. Our results have demonstrated that FIR-HA should be considered as a suitable drying method for mulberry tea with respect to preserving its antioxidant properties and phenolic compounds.     

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.     

Kinetics of lipid oxidation in the presence of cinnamic acid derivatives

The effects of seven (prenyl‐ and methoxy‐) derivatives of cinnamic acid (0.1 mM) on the kinetics of lipid (sunflower oil triacylglycerols, TGSO) bulk phase oxidation at 80 °C have been compared. Synthesis of prenyl cinnamic acid derivatives: 3‐prenyl‐4‐hydroxy‐cinnamic acid (PHC), 3,5‐diprenyl‐4‐hydroxy‐cinnamic acid (DPHC), 2,2‐di‐methyl‐6‐carboxy‐ethenyl‐2H‐benzopyran (DMCB), 2,2‐dimethyl‐6‐carboxy‐ethenyl‐8‐prenyl‐2H‐benzopyran (DCEPB) present in Brazilian propolis has been performed. The monoprenyl derivative (PHC) has been found to exert a higher antioxidant activity as compared to the diprenyl derivative (DPHC). However, cinnamic acid derivatives DMCB and DCEPB have caused no change in the kinetics of TGSO oxidation. The results obtained have been compared with those on related compounds containing a cinnamic acid moiety as a structural feature, such as 4‐hydroxy‐cinnamic (p‐coumaric), 3‐methoxy‐4‐hydroxy‐cinnamic (ferulic) and 3,5‐dimethoxy‐4‐hydroxy‐cinnamic (sinapic) acids, as well as with data on butylated hydroxytoluene (BHT) and α‐tocopherol (αToc). PHC has shown a stronger antioxidant efficiency than BHT, p‐coumaric and ferulic acid, but a weaker antioxidant efficiency than α‐Toc and sinapic acid. The observed antioxidant effect of DPHC was stronger than that of p‐coumaric and ferulic acids and weaker than that of α‐Toc, BHT and sinapic acid.     

Phenolic Characterization and Geographical Classification of Commercial Extra Virgin Olive Oils Produced in Turkey

The aim of this research was to characterize the extra virgin olive oil samples from different locations in the Aegean coastal area of Turkey in terms of their phenolic compositions for two consecutive years to show the classification of oil samples with respect to harvest year and geography. Forty seven commercial olive oil samples were analyzed with HPLC–DAD, and 17 phenolic compounds were quantified. Hydroxytyrosol, tyrosol, vanillic acid, p-coumaric acid, ferulic acid, cinnamic acid, luteolin and apigenin were the characteristic phenols observed in all oil samples for two harvest years. Syringic acid, vanillin and m-coumaric acid were the phenolic compounds appeared in the olive oil depending on the harvest year. Partial least square-discriminant analysis (PLS-DA) of data revealed that oils from the north Aegean and south Aegean areas had different phenolic profiles. The phenolic compounds, which played significant roles in the discrimination of the olive oils, were tyrosol, oleuropein aglycon, cinnamic acid, apigenin and hydroxytyrosol to tyrosol ratio. The Aegean coastal region is the largest olive oil producer and exporter of Turkey. This study shows that the olive oils from different parts of the region have their own defining characteristics that can be used in the authentication studies and geographical labeling of Turkish olive oils.     

A chemical basis for differential allelopathic potential of sorghum hybrids on wheat

The basis for differential allelopathic potentials among sorghum (Sorghum bicolor L. Moench) hybrids was investigated by conducting quantitative and qualitative studies of their phenolic contents. Total phenolic content in sorghum plant parts varied within hybrids, among hybrids, and between growing seasons. Inhibition of wheat (Triticum aestivum L.) radicle growth was positively associated (r=0.66) with concentrations of total phenolics contained in plant parts. Extracts from culms contributed the higherst proportion of toxicity from sorghum plants, inhibiting radicle growth up to 74.7%. Concentrations of five phenolic acids,p-hydroxybenzoic (POH), vanillic (VAN), syringic (SYR),p-coumaric (PCO), and ferulic (FER), differed in all plant parts of the three sorghum hybrids. Concentrations of POH, VAN, and SYR were consistently higher than PCO and FER. PCO and FER wer absent from some plant parts, with FER being the most frequently missing. Inhibition of wheat radicle growth was found to be positively associated with the concentration of each phenolic acid. Vanillic acid was most highly associated (r=0.44) with inhition. Thus, above-ground sorghum tissues contained phenolic acids that contributed to allelopathic potential. Additionally, sorghum roots exuded POH, VAN, and SYR that may enhance the overall allelopathic potential of sorghum during growth and after harvest when residues remain on the soil surface or are incorporated prior to planting a subsquent crop.Journal article No. 12245 of the Missouri Agricultural Experiment Station. Product names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the products, and the use of names by USDA implies no approval of the products to the exclusion of others that may be suitable.