2-hexenal--z-isomer and 2-pentenal

Regulated deficit irrigation (RDI) is used in hedgerow olive orchards to achieve a sustainable balance between water savings, tree vigor and oil production. Its effects on the presence of compounds responsible for the taste of the oil and its nutritional value are controversial. The present 3-year study was conducted in an 'Arbequina' orchard (1667 trees ha. In general, oils from the 30% RDI treatment had higher contents of pigments and phenolic compounds, a higher oleic/linoleic ratio and the highest oxidative stability, despite their lower tocopherol content. FI oils showed higher (E)-2-hexenal, 1-penten-3-one, ocimene, E-2-pentenal and pentene dimer contents than 30RDI oils, but lower contents of (E)-2-pentenol and volatile esters.. The results of the present study suggest that a RDI strategy supplying 30% of the total irrigation needs induces an increase in natural antioxidants in VOO. Neither yield, nor the rest of the quality parameters were affected by the reduced irrigation. However, abundant autumn precipitation can over-ride these effects of 30% RDI treatment on oil quality. © 2016 Society of Chemical Industry.

Topics: Agricultural Irrigation; Aldehydes; Antioxidants; Conservation of Natural Resources; Crop Production; Crops, Agricultural; European Union; Food Quality; Fruit; Humans; Hydrogen-Ion Concentration; Nutritive Value; Olea; Olive Oil; Oxidation-Reduction; Pentanones; Pigments, Biological; Spain; Tocopherols; Up-Regulation; Volatile Organic Compounds

The effects of 16 aliphatic aldehydes with 3-10 carbons on the growth and patulin production of Penicillium expansum were examined. When P. expansum spores were inoculated into apple juice broth, some alkenals, including 2-propenal, (E)-2-butenal, (E)-2-pentenal, and (E)-2-hexenal, inhibited fungal growth and patulin production. Their minimal inhibitory concentrations were 5, 50, 80, and 80 µg/mL respectively. Vital staining indicated that these alkenals killed mycelia within 4 h. Treatment of the spores with these aldehydes also resulted in rapid loss of germination ability, within 0.5-2 d. On the other hand, aliphatic aldehydes with 8-10 carbons significantly enhanced patulin production without affecting fungal growth: 300 µg/mL of octanal and 100 µg/mL of (E)-2-octenal increased the patulin concentrations in the culture broth by as much as 8.6- and 7.8-fold as compared to that of the control culture respectively. The expression of the genes involved in patulin biosynthesis in P. expansum was investigated in mycelia cultured in apple juice broth containing 300 µg/mL of octanal for 3.5, 5, and 7 d. Transcription of the msas gene, encoding 6-methylsalicylic acid synthase, which catalyzed the first step in the patulin biosynthetic pathway was remarkably high in the 3.5-d and 5-d-old cultures as compared with the control. However, octanal did not any increase the transcription of the msas in the 7-d-old culture or that of the other two genes, IDH and the peab1, in culture. Thus the enhanced patulin accumulation with supplementation with these aldehydes is attributable to the increased amount of the msas transcript.

Topics: Acrolein; Acyltransferases; Aldehydes; Beverages; Fermentation; Fruit; Fungal Proteins; Gene Expression; Ligases; Malus; Multienzyme Complexes; Mycelium; Oxidoreductases; Patulin; Penicillium; Spores, Fungal; Transcription, Genetic

The concentration of 31 volatiles were measured in the headspace of tomatillos using selected ion flow tube-mass spectrometry (SIFT-MS), and were compared with those in vine-ripened tomato, roma tomato, cherry tomato, and grape tomato. None of the volatiles were higher in the headspace of tomatillos than of tomatoes. Compounds (E)-2-octenal, (E)-2-pentenal, 2-isobutylthiazole, 6-methyl-5-hepten-2-one, and phenylacetaldehyde were significantly lower in tomatillo than in the tomato varieties in the headspace. After blending, volatiles in the headspace increased, and then decreased after reaching a maximum concentration, due to further degradation or depletion. Compounds (E)-2-pentenal and 1-penten-3-one reached a maximum concentration later than (E)-2-hexenal, (Z)-3-hexenal, and hexanal for tomatillo and tomatoes. The slope of the ratio of (E)-2-hexenal and (Z)-3-hexenal was not significantly different for any of the samples, implying that the activity of cis/trans isomerase was not different between tomatillos and tomatoes.

Topics: Aldehydes; Food Analysis; Food Handling; Fruit; Lipid Metabolism; Mass Spectrometry; Molecular Structure; Pentanones; Physalis; Solanum lycopersicum; Species Specificity; Stereoisomerism; Time Factors; Volatile Organic Compounds

Rate coefficients for the gas-phase reaction of the OH radical with (E)-2-pentenal (CH(3)CH(2)CH[double bond]CHCHO), (E)-2-hexenal (CH(3)(CH(2))(2)CH[double bond]CHCHO), and (E)-2-heptenal (CH(3)(CH(2))(3)CH[double bond]CHCHO), a series of unsaturated aldehydes, over the temperature range 244-374 K at pressures between 23 and 150 Torr (He, N(2)) are reported. Rate coefficients were measured under pseudo-first-order conditions in OH with OH radicals produced via pulsed laser photolysis of HNO(3) or H(2)O(2) at 248 nm and detected by pulsed laser-induced fluorescence. The rate coefficients were independent of pressure and the room temperature rate coefficients and Arrhenius expressions obtained are (cm(3) molecule(-1) s(-1) units): k(1)(297 K)=(4.3 +/- 0.6)x 10(-11), k(1)(T)=(7.9 +/- 1.2)x 10(-12) exp[(510 +/- 20)/T]; k(2)(297 K)=(4.4 +/- 0.5)x 10(-11), k(2)(T)=(7.5 +/- 1.1)x 10(-12) exp[(520 +/- 30)/T]; and k(3)(297 K)=(4.4 +/- 0.7)x 10(-11), k(3)(T)=(9.7 +/- 1.5)x 10(-12) exp[(450 +/- 20)/T] for (E)-2-pentenal, (E)-2-hexenal and (E)-2-heptenal, respectively. The quoted uncertainties are 2sigma(95% confidence level) and include estimated systematic errors. Rate coefficients are compared with previously published room temperature values and the discrepancies are discussed. The atmospheric degradation of unsaturated aldehydes is also discussed.

Topics: Aldehydes; Chemical Phenomena; Chemistry, Physical; Hydroxyl Radical; Kinetics; Molecular Structure; Time Factors

Five alk-2-enals--pent-2-enal, hex-2-enal, hept-2-enal, oct-2-enal and non-2-enal--produced by lipid peroxidation were tested for mutagenic activity in V79 Chinese hamster cells. At concentrations ranging from 0.003 to 0.3 mM all 5 alk-2-enals induced a dose-dependent increase in the frequency of 6-thioguanine-resistant mutants, and their mutagenic potency was found to increase with the length of the carbon chain. In contrast, only hept-2-enal produced a statistically significant increase in the number of mutations to ouabain resistance.

Topics: Aldehydes; Animals; Cell Line; Lipid Peroxidation; Mutagenicity Tests; Mutation