[Photocolorimetric method of hexenal determination].
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Colorimetry↗
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Results for “HEXENAL”
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[Age-specific reactions of animals to the effects of cardiazol (metrazol) and hexenal (Hexobarbital)].
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Age Factors↗
[On the mechanism of potentiation of hypnotic action of hexenal by chlorazicin].
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Animals↗
[Daily dynamics of the duration of hexenal narcosis in experimental hepatosis].
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Animals↗
[The effect of epiphysectomy on the power of hexenal to alter the EEG spectral characteristics over a transitional 24-hour period].
In pinealectomized rats, in the morning (06.00-09-00) the ability of hexobarbital sodium, 60 mg/kg i. p., to increase cortical and hippocampal EEG spectral characteristics was significantly enhanced. On the contrary, in the evening (18.00-21.00) it was decreased. These changes may be associated with pineal gland involvement in circadian rhythm.
Animals↗
[Regional changes of blood volume during ether and hexenal anesthesia].
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Anesthesia, General↗
C6-volatiles derived from the lipoxygenase pathway induce a subset of defense-related genes.
Six-Carbon (C6-) volatiles, including the aldehydes trans-2-hexenal, hexanal and cis-3-hexenal, as well as their corresponding alcohols, are produced from damaged or wounded plant tissue as a product of the enzymatic activity of hydroperoxide lyase (HPL), a component of the lipoxygenase (LOX) pathway. Aerial treatment of Arabidopsis seedlings with 10 microM concentrations of trans-2-hexenal induces several genes known to be involved in the plant's defense response, including phenylpropanoid-related genes as well as genes of the LOX pathway. Genes encoding the pathogenesis-related proteins PR-1 or PR-2, however, were not induced. Trans-2-hexenal induction thus closely mimics the group of genes induced by methyl jasmonate (MeJA), also a LOX-derived volatile. However, unlike MeJA, trans-2-hexenal did not induce hydroxymethylglutaryl-coenzyme A reductase (HMGR) or thionin2-1. The inductive effect seemed to be limited to C6-related volatiles, as C8-, C9- and other related volatiles did not induce LOX mRNA levels. As has been demonstrated for MeJA, trans-2-hexenal quantitatively reduced wild-type seed germination. Trans-2-hexenal also reduced the germination frequency of the MeJA resistant Arabidopsis mutant, jar1-1, supporting the notion that trans-2-hexenal and MeJA are recognized via different mechanisms. In addition, trans-2-hexenal had a moderate inhibitory effect on root length relative to similar concentrations of MeJA and was approximately 10-fold less effective than MeJA at inducing anthocyanin accumulation in Arabidopsis seedlings. These results suggest that C6-volatiles of the LOX pathway act as a wound signal in plants, but result in a moderate plant response relative to MeJA at both the physiological and molecular level.
Acetates↗
Formation of lipoxygenase-pathway-derived aldehydes in barley leaves upon methyl jasmonate treatment.
In barley leaves, the application of jasmonates leads to dramatic alterations of gene expression. Among the up-regulated gene products lipoxygenases occur abundantly. Here, at least four of them were identified as 13-lipoxygenases exhibiting acidic pH optima between pH 5.0 and 6.5. (13S,9Z,11E,15Z)-13-hydroxy-9,11,15-octadecatrienoic acid was found to be the main endogenous lipoxygenase-derived polyenoic fatty acid derivative indicating 13-lipoxygenase activity in vivo. Moreover, upon methyl jasmonate treatment > 78% of the fatty acid hydroperoxides are metabolized by hydroperoxide lyase activity resulting in the endogenous occurrence of volatile aldehydes. (2E)-4-Hydroxy-2-hexenal, hexanal and (3Z)- plus (2E)-hexenal were identified as 2,4-dinitro-phenylhydrazones using HPLC and identification was confirmed by GC/MS analysis. This is the first proof that (2E)-4-hydroxy-2-hexenal is formed in plants under physiological conditions. Quantification of (2E)-4-hydroxy-2-hexenal, hexanal and hexenals upon methyl jasmonate treatment of barley leaf segments revealed that hexenals were the major aldehydes peaking at 24 h after methyl jasmonate treatment. Their endogenous content increased from 1.6 nmol.g-1 fresh weight to 45 nmol.g-1 fresh weight in methyl-jasmonate-treated leaf segments, whereas (2E)-4-hydroxy-2-hexenal, peaking at 48 h of methyl jasmonate treatment increased from 9 to 15 nmol.g-1 fresh weight. Similar to the hexenals, hexanal reached its maximal amount 24 h after methyl jasmonate treatment, but increased from 0.6 to 3.0 nmol.g-1 fresh weight. In addition to the classical leaf aldehydes, (2E)-4-hydroxy-2-hexenal was detected, thereby raising the question of whether it functions in the degradation of chloroplast membrane constituents, which takes place after methyl jasmonate treatment.
Acetates↗
Phenol--another cockchafer attractant shared by Melolontha hippocastani Fabr. and M. melolontha L.
The response of the two most abundant cockchafer species in central Europe, Melolontha hippocastani and M. melolontha, towards phenol, mixtures of phenol with the leaf alcohol (Z)-3-hexen-1-ol and the known cockchafer pheromones, 1,4-benzoquinone (M. hippocastani) and toluquinone (M. melolontha), was investigated in the field. During the swarming period at dusk, phenol attracted males of both species, and enhanced the known attraction of cockchafer males towards (Z)-3-hexen-1-ol. A mixture of phenol plus (Z)-3-hexen-1-ol was less attractive for M. hippocastani males than a mixture of (Z)-3-hexen-1-ol plus 1,4-benzoquinone, whereas phenol plus (Z)-3-hexen-1-ol attracted as many M. melolontha males as a mixture of (Z)-3-hexen-1-ol plus toluquinone. In both species three component mixtures containing phenol, (Z)-3-hexen-1-ol, and the respective benzoquinone did not capture more males than two component mixtures consisting of only (Z)-3-hexen-1-ol and the benzoquinone. A possible role of phenol as another cockchafer sex pheromone component is discussed.
Animals↗
Composition of the volatiles from intact and mechanically pierced tea aphid-tea shoot complexes and their attraction to natural enemies of the tea aphid.
The volatile components from intact tea shoots (ITS), obtained by air entrainment, were identified by their mass spectra and retention times and confirmed by comparison with standard samples. They are E-2-hexenal, ocimene, Z-3-hexenyl acetate, Z-3-hexen-1-ol, butanoic acid-3-hexenyl ester, linalool, 1-octanol, geraniol, and indole. Volatiles from mechanically pierced tea shoots (MPTS) were identified as E-2-hexenal, ocimene, Z-3-hexen-1-ol, butanoic acid-3-hexenyl ester, linalool, geraniol, indole, E-2-hexenoic acid, Z-3-hexenyl formate, methyl salicylate, and benzyl alcohol, and volatiles from tea aphid-tea shoot complexes (TATSC) were identified as E-2-hexenal, ocimene, Z-3-hexenyl acetate, Z-3-hexen-1-ol, linalool, geraniol, indole, benzaldehyde, and E-2-hexenoic acid. Z-3-Hexen-1-ol is the main component in the three different types of volatiles, and the amount of benzaldehyde in TATSC volatiles is very ample. The attraction of the volatiles from ITS, MPTS, and TATSC, and the nine components of TATSC volatiles to the natural enemies, the coccinellid, Coccinella septempunctata, the parasite, Aphidius sp., and the lacewing, Chrysopa sinica, were determined by electroantennogram (EAG) and the wind tunnel bioassay. TATSC volatiles and benzaldehyde elicited much larger EAG responses and stronger upwind flight and arresting behavior from each natural enemy in the wind tunnel than other infochemicals.
Animals↗
Defensive chemistry of an aposematic bug, Pachycoris stallii Uhler and volatile compounds of its host plant Croton californicus Muell.-Arg.
Volatile components of Pachycoris stallii scent gland secretions and the bug's host plant, Croton californicus, were identified by gas chromatography and mass spectroscopy. The predominant compounds isolated from C. californicus fruit and leaves were beta-myrcene and beta-caryophyllene. Metathoracic gland secretions of P. stallii contained mostly (E)-2-hexenal, (E)-4-oxo-2-hexenal, (E)-2-hexenyl acetate, and n-tridecane. In males, n-tridecane was present throughout the metathoracic gland, but in females this compound was found only in the median reservoir/accessory gland. (E)-2-Hexenal was present throughout the gland of female bugs, but in males was primarily present in the median reservoir/accessory gland. (E)-4-Oxo-2-hexenal and n-dodecane were isolated from the median reservoir/accessory gland of male and female bugs. Metathoracic glands were sexually monomorphic. Data from chemical analyses and anatomical observations suggest that dorsal abdominal glands of adults were apparently obsolescent. In nymphs, dorsal abdominal glands produced (E)-2-hexenal, (E )-4-oxo-2-hexenal, n-dodecane, n-tridecane, and tetradecanal. The proportion of the predominant constituent, (E)-4-oxo-2-hexenal, decreased from 72% in the first instar to 47% in the fourth instar. Proportions of tetradecanal and n-tridecane were greater in the fourth instar than in the first instar. Observations of dissected glands indicated that median and posterior dorsal abdominal glands of all nymphal instars were more developed than anterior dorsal abdominal glands. Scanning electron micrography revealed the presence of polygonal microsculpturing on the integument surrounding the ostioles of metathoracic and dorsal abdominal glands. Chemical, anatomical, and behavioral data indicated that P. stallii has a chemical defense system based on short-chain carbonyl compounds and that this system is directed against arthropods. The abundance of arthropod natural enemies apparently has forced P. stallii to maintain this defense system despite feeding on a toxic host plant.
Acetates↗
Comparison of the olfactory sensitivity of two sympatric steppe grasshopper species (Orthoptera: Acrididae) to plant volatile compounds.
Electroantennogram (EAG) responses of male and female Oedipodinae grasshoppers, Oedaleus decorus asiaticus B.-Bienko and Angaracris barabensis Pall to 37 plant volatile compounds were recorded. The two species have sympatric distribution and synchronous seasonal activity in Inner Mongolia Grasslands. They have different host plant preference with Oedaleus decorus asiaticus graminivorous and A. barabensis forbivorous. The EAG response profiles to 37 compounds of the two species and their both sexes were similar. Most of the green leaf volatiles elicited higher EAG responses in both species and sexes than terpenic compounds and some aromatic compounds. Strong EAG responses were elicited by 6-carbon alcohols (1-hexanol, Z-hexen-2-ol-1, E-2-hexen-1-ol, E-hexen-3-ol-1), aldehyde (E-2-hexen-1-al), ester (Z-hexen-3-yl acetate), and 7-carbon alcohols (1-heptanol) in both species and sexes. Monoterpenes with functional groups of alcohols and aldehydes were more stimulating than other monoterpenes tested. The sesquiterpenes tested elicited relatively low responses. Benzaldehyde elicited the highest responses for both species among aromatic components. Oedaleus decorus asiaticus showed higher EAG responses than A. barabensis to the green leaf volatiles, 1-decanol, 1-nonanol, 1-pentanol, hexanal, Z-hexen-3-yl acetate and to the sesquiterpenes (-)-trans-caryophyllene. Males have higher responses than females in Oedaleus decorus asiaticus. No sexual difference was observed in A. barabensis. Dose-dependent responses to six selected chemicals were observed from females. In both species, all the chemicals tested elicit EAG responses at concentration between 10(-3) mol/L and 10(-2) mol/L, except that the responses of A. barabensis to terpineol had a threshold concentration of 10(-2) mol/L benzaldehyde and 1-hexanol had the highest slopes in dose curves, while 1-octen-3-ol showed the smallest slope in responses to the six chemicals tested. Comparative studies on the responses of two antennal sections and the whole antenna to six selected chemicals were carried out using females of both species. A significant EAG response was only recorded from the distal part of the antenna and not from the proximal seven segments.
Alcohols↗
Hydroperoxide-lyase activity in mint leaves. Volatile C6-aldehyde production from hydroperoxy-fatty acids.
The extraction of 13-hydroperoxide-lyase activity from mint leaves as well as its use for C6-aldehyde production was studied in this work. The enzyme cleaves 13(S)-hydroperoxy-C18 fatty acids into C6-aldehyde and C12-oxo-acid. Two mint species were tested: Mentha veridis and Mentha pulegium. The headspace injection method coupled to gas chromatography was used for volatile compound analysis. The optimal conditions for temperature and pH were, respectively, 15 and 7 degrees C. We also studied the specific synthesis of hexanal and hexenals respectively from 13(S)-hydroperoxy-linoleic acid and 13(S)-hydroperoxy-linolenic acid. Considerable quantities of aldehyde (up to 2.58 micromol) were produced after 15 min of cleavage reaction in 2 ml stirred at 100 rpm, especially in presence of extract of M. veridis. The conversion yields decreased from 52.5% as maximum to 3.3% when using initial hydroperoxide concentrations between 0.2 and 15 mM. An unsaturated aldehyde, the 3(Z)-hexenal was produced from 13(S)-hydroperoxy-linolenic acid. The 3(Z)-isomer was unstable and isomerized in part to 2(E)-hexenal. In this work, we observed a very limited isomerization of 3(Z)-hexenal to 2(E)-hexenal, since the reaction and the volatile purge were carried out successively in the same flask without delay or any contact with the atmosphere. These aldehydes contribute to the fresh green odor in plants and are widely used in perfumes and in food technology. Their importance increases especially when the starting materials are of natural biological origin as used in this work. GC-MS analysis allowed the identification of the products.
Aldehyde-Lyases↗
Behavioral responses of the diamondback moth, Plutella xylostella, to green leaf volatiles of Brassica oleracea subsp. capitata.
Green leaf volatiles (GLVs) from Brassica oleracea subsp. capitata L. have been identified as 1-hexanol, (Z)-3-hexen-1-ol, 1-hexen-3-ol, hexanal, (E)-2-hexenal, hexyl acetate, and (Z)-3-hexenyl acetate, by their mass spectra and retention times in comparison with authentic samples. No isothiocyanates were found in the extract. The activity of these chemicals has been determined on mated and unmated males and females of the diamondback moth (DBM) Plutella xylostella in the laboratory (wind tunnel) and in the field. On unmated males, mixtures of (Z)-3-hexenyl acetate, (E)-2-hexenal, and (Z)-3-hexen-1-ol with the pheromone induced attractant/arresting behavior in 80-100% of the males tested, significantly higher than the effect induced by the pheromone alone. On mated males and unmated females the effect of the GLVs alone or in combination with the pheromone was poor, while on mated females these compounds elicited upwind flight and arresting behavior in 40-60% of the females assayed. There was no synergism when these chemicals were mixed with the pheromone. In the field, (Z)-3-hexenyl acetate, the most active GLV in laboratory tests, when mixed with the pheromone in 1:1 ratio, enhanced 6-7-fold the number of females and 20-30% the number of males caught by traps over those baited with the pheromone alone. Our results indicate that the enhancement of the attraction of both males and females of the DBM to traps baited with pheromone blended with the relatively inexpensive and environmentally safe (Z)-3-hexenyl acetate may be important for future control strategies of the pest.
Animals↗
A simple and efficient system for green note compound biogenesis by use of certain lipoxygenase and hydroperoxide lyase sources.
Six-carbon (C(6)) aldehydes and alcohols are important components of the aroma and flavor of fruits and vegetables. Soybean lipoxygenase (LOX) isozyme LOX 3 was reported not only to produce less 13-hydroperoxides, precursors of C(6) aldehydes, but also to convert them to ketodiene products. Here, we examined the effects of LOX 3 on hexenal formation from linolenic acid homogenized with watermelon 13-hydroperoxide lyase (HL)-overexpressing Nicotiana tabacum leaves and soybean acetone powder. Compared to the wild type, which contains LOXs 1, 2, and 3, the elimination of LOX 3 in LOX 1 + 2 facilitates greater production of hexenals. The use of LOX 2 alone yielded the highest hexenal production, while a two-step conversion was required for LOX 1 to produce hexenals at high levels due to different pH optima of the enzymes involved. These results clearly demonstrate that the soybeans lacking LOX 3 in combination with watermelon HL-overexpressing leaf tissues greatly enhance hexenal formation.
Alcohols↗
Orthonasal and retronasal perception of some green leaf volatiles used in beverage flavors.
Orthonasal perception of six green leaf volatiles (GLVs) classified only hexanal, (E)-2-hexenal, and (Z)-3-hexen-1-yl formate as green. (Z)-3-Hexen-1-yl hexanoate and (Z)-3-hexen-1-yl 3-methylbutyrate were more floral, and (Z)-3-hexen-1-yl acetate fell between the two groups. For retronasal perception, classification along a bipolar green-fruity scale is proposed for describing these GLVs. Data from grouping and dissimilarity tests as well as from sensory profiling show green character for these compounds in standard beverage bases having low Brix or high acidity. As the Brix value increases (or acidity decreases) within the limits encountered in commercial beverages, the character becomes fruity. Several tastant-dependent changes in intensity scores for retronasal descriptors were shown to occur for mixtures of GLVs. The GLVs did not affect intensity scores for gustatory descriptors.
Beverages↗
Odorization of inert gas for occupational safety: psychophysical considerations.
Odorization of inert gas can serve to warn workers in an enclosed space about gas leaking into the space. This psychophysical investigation, performed under conditions of directed attention, examined two candidates for possible odorization of argon:pyridine and cis-3-hexen-1-ol. Detection thresholds for pyridine and cis-3-hexen-1-ol in argon were 106 ppb and 19 ppb, respectively. Practice over four days yielded modest improvement in the detection of both odorants. For cis-3-hexen-1-ol, smokers had marginally lower thresholds than nonsmokers and older participants had slightly higher thresholds than younger participants. Gender, smoking status and age had no reliable influence on threshold for pyridine. This outcome indicated desirable perceptual stability for pyridine. Additional experiments dealt with the perceived intensity of pyridine and cis-3-hexen-1-ol over time in the realistic setting of an environmental chamber. Visitors to the chamber and occupants in the chamber assessed perceived magnitude at 5-min intervals for up to 60 min during injections of odorized argon into the chamber. Participants could gauge and track the concentration of pyridine much better than that of cis-3-hexen-1-ol. This held true for occupants almost to the same degree as visitors, though occupants inevitably exhibited some olfactory adaptation. Hence, the suprathreshold measurements also gave strong relative endorsement to pyridine. Calculations based on the experimental results indicated that odorization of the inert gas stream with 3 to 10 ppm (v/v) pyridine should suffice to warn occupants or visitors of an argon buildup of any severity. Field studies should permit a definitive judgment of the best concentration to use in practice.
Adult↗
Oxygenation of (3Z)-alkenal to (2E)-4-hydroxy-2-alkenal in soybean seed (Glycine max L.).
(3Z)-Alkenals, such as (3Z)-hexenal and (3Z)-nonenal, are produced from polyunsaturated fatty acids via lipoxygenase and hydroperoxide lyase catalysis, but in soybeans (Glycine max L.) (3Z)-alkenals have a fleeting existence. In this study it was shown that soybean seeds possess two pathways that metabolize (3Z)-alkenals. One is a soluble (3Z):(2E)-enal isomerase that transformed (3Z)-hexenal and (3Z)-nonenal into the corresponding (2E)-alkenals. The other was a membrane-bound system that converted (3Z)-hexenal and (3Z)-nonenal into (2E)-4-hydroxy-2-hexenal and (2E)-4-hydroxy-2-nonenal, respectively. The latter conversion was shown to absorb O2 with a pH optimum of 9.5. Little effect observed with lipoxygenase inhibitors suggested that oxidation was not catalyzed by lipoxygenase. Instead, a specific (3Z)-alkenal oxygenase was implicated in forming intermediate alkenal hydroperoxides. Hydroperoxide-dependent peroxygenase (epoxygenase) is known to reduce hydroperoxides to their corresponding hydroxides and is also known to be inhibited by hydrogen peroxide preincubation. Consequently, intermediate 4-hydroperoxy-2-alkenals could be observed after inhibiting hydroperoxide-dependent peroxygenase by preincubation with hydrogen peroxide. Because 4-hydroxy-2-alkenals are potent toxins, these compounds may be produced as nonvolatile plant defensive substances.
Aldehydes↗