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PubMed1999

Off-flavor compounds in wine and other food products formed by enzymatical, physical, and chemical degradation of tryptophan and its metabolites.

Tryptophan (TRP) and its metabolites are considered as potential precursors of 2-aminoacetophenone (AAP) in different food products causing different off-flavors. AAP is also responsible for the "untypical aging flavor (UTA)" in wine, developing a floor polish-like flavor in white wines within a few months of storage. In this study the formation of AAP was elucidated by GC-MS analysis of volatile components in model systems, grape musts and wines, spiked with TRP and different TRP metabolites like indole-3-acetic acid (IAA) and sulfite. In sulfurized wines and model solutions which were stored at different temperatures (20 degrees C, 45 degrees C) formylaminoacetophenone (FAP) and AAP were formed mainly from IAA with formation rates up to 20 mole%. Minor formation rates of AAP (< 1 mole%) were found in sulfurized solutions of TRP, indole-3-lactic acid, and indole-3-pyruvic acid. The results showed that the formation of AAP in wine can be referred to an oxidative degradation of IAA by superoxide- and hydroxyl-radicals, which can be formed in wine after the sulfuration by cooxidation of sulfite to sulfate. After decarboxylation, pyrrole oxidation, and ring cleavage, FAP was the main volatile compound of the nonenzymatic degradation of IAA by sulfite which was quantitatively hydrolyzed to AAP. The formation of AAP and FAP was significantly lower in white wines than in ethanolic solutions spiked with IAA. However AAP formation rates of up to 5 mole% were still enough for an UTA. Due to the fact that the AAP- and UTA-formation by cooxidation of sulfite and IAA was completely blocked in red wines, it could be deduced that polyphenolic compounds, typical for red wines, have a scavenger effect on the radical oxidation of sulfite. Possibilities for an inhibition of the IAA degradation during winemaking to avoid the UTA in white wines by addition of radical scavengers like grape marc or ascorbic acid are discussed.

Acetophenones↗
PubMed1999

Determination of tryptophan and tryptophan metabolites in grape must and wine.

Tryptophan (Trp) and its metabolites, especially indole-3-acetic acid (IAA), are considered as potential precursors of 2-aminoacetophenone (AAP), an aroma compound which causes the "untypical aging off-flavor" (UTA) in Vitis vinifera white wines. In this study RP-HPLC with fluorescence detection was used for the qualitative and quantitative analysis of Trp and Trp-metabolites in 39 grapes, 22 grape musts and 16 wines, to which different viticultural conditions (ripeness, pruning, strip of leaves, soil condition) have been applied. A sensitive and selective determination was achieved after solid phase extraction using an anion exchange material. Only traces of Trp-metabolites could be determined in the examined grapes and grape musts, but their amounts increased significantly during fermentation, whereas the amount of Trp decreased. Different viticultural measures, besides the time of grape harvest, showed no significant influences on the amount of Trp and Trp-metabolites.

Acetophenones↗
PubMed1991

Environmental conditions differentially affect vir gene induction in different Agrobacterium strains. Role of the VirA sensor protein.

The induction of vir gene expression in different types of Agrobacterium strains shows different pH sensitivity profiles. The pH sensitivity pattern demonstrated by octopine Ti strains was similar to that of a supervirulent leucinopine Ti strain, whereas this was different from that shown by nopaline Ti strains and agropine Ri strains. Data are given which indicate that these differences are due to different properties of the virA genes of these wild types. An exceptional case was formed by strains with the limited-host-range plasmid pTiAG57 which showed AS-dependent vir induction only if reduced inoculum sizes were used and the temperature was 28 degrees C or below.

Acetophenones↗
PubMed1994

Localization of the VirA domain involved in acetosyringone-mediated vir gene induction in Agrobacterium tumefaciens.

The VirA protein of Agrobacterium tumefaciens is thought to be a receptor for plant phenolic compounds such as acetosyringone. Although it is not known whether the interaction between VirA and the phenolics is direct or requires other phenolic-binding proteins, it is shown in this study that the first 280 amino acids of the VirA protein are not essential for the acetosyringone mediated vir gene induction response. Considering the fact that the cytoplasmic region between the amino acids 283 and 304 is highly conserved between the different VirA proteins, and that deletion of this region abolishes VirA activity, we suggest that the acetosyringone receptor domain is located in this cytoplasmic domain of the VirA protein.

Acetophenones↗
PubMed1996

A proposed common spatial pharmacophore and the corresponding active conformations of some peptide leukotriene receptor antagonists.

Molecular modeling studies were carried out by a combined use of conformational analysis and 3D-QSAR methods of identify molecular features common to a series of hydroxyacetophenone (HAP) and non-hydroxyacetophenone (non-HAP) peptide leukotriene (pLT) receptor antagonists. In attempts to develop a ligand-binding model for the pLT receptor, the Apex-3D program was used to identify biophoric structural patterns that are common to 13 diverse sets of compounds showing different levels of biological activity. A systematic conformational analysis was carried out to obtain sterically accessible conformations for these flexible compounds. Apex-3D was then utilized to propose common biophoric regions based on the selection of one of several conformations (MOPAC-minimized AM1) from each compound's data set that best fits the biophoric pattern and the resulting superimposition with all the other data-set compounds. Apex-3D identified three common biophoric features important for activity: one as the hydroxyl, acetyl, carbonyl and carboxyl groups, which mimic the acid-binding region of an agonist, the other as the hydrogen-bond donating site, and the third part is represented by a plane in which lipophilic aromatic groups align. The structure-activity relationships were then assessed by using the 3D-QSAR model. A common biophore model is proposed from the Apex-3D analysis which may be useful in designing new pLT antagonists. Molecular volumes and electrostatic potential similarities were also calculated in order to obtain the important structural requirements for the activity.

Acetophenones↗
PubMed1991

OVID and SUPER: two overlap programs for drug design.

Two programs, OVID and SUPER, for exploring the similarity of molecules with respect to their action at a receptor are described. OVID accepts two molecules as input and optimizes the three-dimensional overlap of specified atoms in one molecule with specified atoms in the second molecule. The result is expressed as a percent of the theoretical maximum. OVID gives a quantitative measure of the extent of a guessed correspondence between two molecules based on volume overlap of selected atoms. The Achilles' heel of OVID is that the correspondence between the two molecules has to be guessed. We realized that it would be better to systematically examine all possible correspondences of two structures to minimize the chance of overlooking a superior correspondence. We created SUPER to satisfy this need. SUPER accepts two molecules as input and finds the top twenty correspondences of their surfaces and charge distributions, giving a quantitative measure of the extent of each correspondence. An instructive example of the application of OVID and SUPER to the design of leukotriene D4 receptor antagonists is described. SUPER appears to be a practical brain-storming tool for the medicinal chemist trying to understand how molecules whose structures may not resemble one another in an obvious way can bind to the same site.

Acetophenones↗
PubMed1993

Contraction of guinea pig inferior vena cava by eicosanoids.

Guinea pig inferior vena cava contracted in response to leukotriene (LT)C4, LTD4, LTE4 U46619, phenylephrine, histamine, and KCl. Although LTC4, LTD4, and U46619 were the most potent agonists, active tension generated by these eicosanoids was only about half that of histamine or KCl. LTE4 and phenylephrine were marginally active. Biochemical analysis showed vena cava able to convert about 23% LTC4 to LTD4 and LTE4 in 45 min. Pretreatment with acivicin prevented this by abrogating conversion of LTC4 to LTD4. A subthreshold concentration of LTE4 reduced responses to LTC4 and LTD4. LY171883 and WY-48252 competitively antagonized LTD4-induced contractions of vena cava. In contrast, these antagonists blocked contractions to LTC4 in a biphasic manner. Lower segments of the LTC4 concentration-response curves were less affected than the upper portion suggesting the possibility of 2 LTC4 receptor subtypes. Our results indicate that LTE4 is a weak or partial agonist in this tissue and furthermore they suggest a lack of high affinity receptors for LTE4 favoring LTC4 and LTD4. Indomethacin did not influence contractions to the leukotrienes or histamine. However, the response to U46619 was greatly enhanced suggesting release of a vasodilator prostaglandin as part of the overall response of the vena cava to the thromboxane A2 mimetic.

15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5↗
PubMed1996

Role of superoxide anions in airway hyperresponsiveness induced by cigarette smoke in conscious guinea pigs.

To investigate the involvement of superoxide in airway hyperresponsiveness and bronchoconstriction induced by cigarette smoke (CS), we evaluated the effects of superoxide dismutase (SOD), a scavenger of superoxide anion, and apocynin, an inhibitor of superoxide anion-generating NADPH oxidase in phagocytes, on the airway responses induced by CS in conscious guinea pigs. Airway responsiveness was assessed by PC200Mch, the concentration required to produce a doubling in the baseline specific airway resistance (sRaw) to an inhaled methacholine aerosol, in nonanesthetized spontaneously breathing animals. Before being exposed to ten puffs of CS, animals inhaled either SOD (5,000 units/ml or 25,000 units/ml) or vehicle. Although SOD did not affect PC200Mch in the air control group, this agent significantly reduced the CS-induced airway hyperresponsiveness. Repeated administration of apocynin (12 mg/kg for 4 days) did not affect PC200Mch after exposure to CS. These data suggest that the superoxide from CS was involved in the airway hyperresponsiveness induced by CS, whereas phagocytic reactive oxygen species were not. The data also suggest a potential therapeutic role for antioxidants in airway hyperresponsiveness.

Acetophenones↗
PubMed1991

Modulation of the beta-adrenergic response in cultured rat heart cells. I. Beta-adrenergic supersensitivity is induced by lactate via a phospholipase A2 and 15-lipoxygenase involving pathway.

Incubation of rocker-cultured neonatal rat heart cells with 3 mM L(+)-lactate led to a sharp increase in the sensitivity of cardiomyocytes to the beta-adrenergic agonist isoprenaline, as measured by their chronotropic response. This effect was accompanied by a reduction in the arachidonic acid content of the total phospholipids. The phospholipase A2-activator melittin as well as free arachidonic acid induced this supersensitivity to the same degree. On the other hand, the L(+)-lactate-evoked supersensitivity could be blocked by the phospholipase A2 inhibitors mepacrine and n-bromophenacyl-bromide, suggesting an involvement of phospholipase A2 in the process of beta-adrenergic sensitization. The sensitizing action of arachidonic acid was blocked by the lipoxygenase inhibitors esculetin and nordihydroguaiaretic acid, but not by the cyclo-oxygenase inhibitor indomethacin. Supersensitivity was likewise evoked by 15-S-hydroxyeicosatetraenoic acid (15-S-HETE), but not by 5-S-HPETE or 5-S-HETE. These findings suggest that the phospholipase A2-15-lipoxygenase pathway plays a role in the induction of beta-adrenergic supersensitivity in the cultured cardiomyocytes and point to a new physiological role of the lipoxygenase product 15-S-HETE.

Acetophenones↗
PubMed1975

The comparative ophthalmic toxicology of 1-chloroacetophenone (CN) and dibenz(b.f)-1:4-oxazepine(CR).

Rabbit eyes were contaminated with 1-chloroacetophenone (CN) and dibenz(b.f)-1:4-oxazepine (CR) in solution (1 to 10% in polyethylene glycol 300), as a solid (0.1 to 5 mg), and as aerosols (15 min exposure to 360 to 719 mg/m3). In solution, CN caused marked and persistent inflammatory effects, the severity and duration being related to the concentration used. Corneal damage was marked and persistent with 5 and 10% solutions; the lowest concentration causing just detectable keratitis in a small proportion of animals was 2%. Solid CN was even more damaging to the eye than similar amounts in solution. In marked contrast, CR in solution caused mild to moderate inflammatory effects, usually of only a few days duration, even at the higher concentrations. With 1 and 2%, these effects were just detectable to mild, lasting for 24 hrs or less. 10% CR caused just detectable keratitis of usually only a few days duration; the lowest concentration causing just detectable keratitis in a small proportion of treated animals was 5%. Solid CR merely caused minor irritation of the conjunctivae and eyelids for about 1 hr. Aerosols of CN and CR did not damage the eye, but irritation of the lids and conjunctivae was more marked and persistent with CN. Solutions of CN and CR caused concentration-related increases in corneal thickness and intraocular tension, being more marked and sustained with CN.

Acetophenones↗
PubMed1992

Aromatic aldehydes and aromatic ketones open ATP-sensitive K+ channels in guinea-pig ventricular myocytes.

Patch-clamp techniques were used to study the effects of three carbonyl compounds, 3,4-dihydroxybenzaldehyde, 2,3-dihydroxybenzaldehyde, and 2,4-dihydroxyacetophenone, on the adenosine-5'-triphosphate(ATP)-sensitive K+ channel current (IK.ATP) in guinea-pig ventricular myocytes. 3,4-Dihydroxybenzaldehyde (0.5-1 mM) shortened the action potential duration, and this effect was inhibited by application of a specific blocker of IK.ATP, glibenclamide. The shortening of the action potential duration was shown to be caused by a time-independent outward current. In the cell-attached patch configuration, all three compounds activated a kind of single-channel current, which showed an inward rectification at positive potentials and which had a linear current/voltage relation at negative potentials, having a conductance of 90 pS. The current reversed at about 0 mV in symmetrical K+ concentrations on both sides of the membrane. In excised patches this current was blocked by internal application of ATP. Thus we identified this channel as IK.ATP. The activation effects of two aromatic aldehydes were stronger than that of the aromatic ketone. The effect of these compounds on IK.ATP was not reduced by addition of cysteine (10 mM). In inside-out patches, 3,4-dihydroxybenzaldehyde increased the activity of IK.ATP, which had been blocked by 0.5 mM MgATP in the presence of 0.5 mM ADP, but the activation effect was variable and much weaker than that in the cell-attached configuration, and was completely eliminated in the absence of ADP.(ABSTRACT TRUNCATED AT 250 WORDS)

Acetophenones↗
PubMed1990

Effects of arachidonic acid on the gap junctions of neonatal rat heart cells.

Myocytes were isolated from neonatal rat hearts and grown in tissue-culture dishes for 1-2 days. Spontaneously formed cell pairs were used to study the conductance of gap junctions. The experiments involved a double voltage-clamp approach and whole-cell, tight-seal recording. Exposure to arachidonic acid (AA) produced a quasi dose-dependent decrease in junctional conductance, gi (binding constant, Kd = 4 microM; Hill coefficient, n = 0.75). AA-dependent uncoupling was reversible. Addition of 1 mg/ml albumin to the bath solution accelerated the recovery. During control, cell pairs exhibited a gradual decrease in gi (16.4% in 6 min). Exposure to 20 microM 4-bromophenacyl bromide, a phospholipase inhibitor, suppressed the decay in gi (1.8% in 6 min), suggesting that endogenous AA may be involved in spontaneous uncoupling. The effect of AA on gi was specific. Arachidic acid (100 microM) and arachidonamide (10 microM), structural analogues of AA, had no effect on gi. Currents recorded shortly before complete uncoupling caused by AA, or early during recovery from uncoupling, revealed random opening and closing of single channels. The single channel conductance, gamma i, was not affected by the concentration of AA (1 microM - 100 microM). The mean gamma i turned out to be 33.5 pS. The results suggest that AA-dependent uncoupling was caused via decrease in open channel probability, presumably mediated by a direct action on channel proteins.

Acetophenones↗
PubMed1975

Food- and drug-reinforced responding: effects of DITA and d-amphetamine.

Intravenous pretreatment with DITA (0.1 - 1.0 mg/kg) decreased the rate of food-reinforcement lever pressing in rhesus monkeys. Response rate decreases were dose-dependent but showed the development of tolerance. Self-administration of DITA was initiated and maintained in each of three monkeys when 30 lever presses were required to produce each injection. Maximal response rate during periods of drug availability was maintained by 0.03 mg/kh/injection while higher and lower doses (0.01 and 0.10 mg/kg/injection) maintained lower response rates. Response rate in periods of food availability immediately preceding drug periods was relatively constant across session; response rate in periods of food availability immediately following drug periods, however, decreased with increasing amounts of drug self-administered. Replication of initial self-administration doses produced results comparable to original determinations in contrast to the tolerance observed with DITA effects upon food-reinforced responding. DITA was about 3 times less potent than d-amphetamine in maintaining response rates in drug periods and in decreasing the rate of subsequent food-reinforced responding.

Acetophenones↗