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The molecule 2-nonenal is renowned as the origin of unpleasant human aging-related body odor that can potentially indicate age-related metabolic changes. Most 2-nonenal measurements rely on chromatographic analytical systems, which pose challenges in terms of daily usage and the ability to track changes in concentration over time. In this study, we have developed liquid- and gas-phase biosensors (bio-sniffers) with the aim of enabling facile and continuous measurement of trans-2-nonenal vapor. Initially, we compared two types of nicotinamide adenine dinucleotide (phosphate) [NAD(P)]-dependent enzymes that have the catalytic ability of trans-2-nonenal: aldehyde dehydrogenase (ALDH) and enone reductase 1 (ER1). The developed sensor quantified the trans-2-nonanal concentration by measuring fluorescence (excitation: 340 nm, emission: 490 nm) emitted from NAD(P)H that was generated or consumed by ALDH or ER1. The ALDH biosensor reacted to a variety of aldehydes including trans-2-nonenal, whereas the ER1 biosensor showed high selectivity. In contrast, the ALDH bio-sniffer showed quantitative characteristics for trans-2-nonenal vapor at a concentration range of 0.4–7.5 ppm (with a theoretical limit of detection (LOD) and limit of quantification (LOQ) of 0.23 and 0.26 ppm, respectively), including a reported concentration (0.85–4.35 ppm), whereas the ER1 bio-sniffer detected only 0.4 and 0.8 ppm. Based on these findings, headspace gas of skin-wiped alcohol-absorbed cotton collected from study participants in their 20s and 50s was measured by the ALDH bio-sniffer. Consequently, age-related differences in signals were observed, suggesting the potential for measuring trans-2-nonenal vapor.

The unsaturated aldehyde trans-2-nonenal is known to be generated by lipid peroxidation at the surface of the skin in an aging-related manner and has harmful effects on keratinocytes in the skin. In this study, the protective effect of a Lycii Radicis Cortex (LRC) extract against trans-2-nonenal-induced cell damage on human keratinocyte cell lines (HaCaT) was investigated. Notably, treatment with the LRC extract resulted in an increase in cell survival, while trans-2-nonenal decreased the viability of HaCaT cells. For identification of interaction between the LRC extract and trans-2-nonenal, this mixture was incubated in simulated physiological conditions, showing a strong decrease in the amount of trans-2-nonenal by the LRC extract. Subsequent LC-ESI-MS analysis revealed that kukoamine B (KB) formed Schiff base-derived pyridinium adducts with trans-2-nonenal. Thus, these results suggest that KB could be a potential agent that may protect HaCaT cells by forming new products with trans-2-nonenal.

[Display omitted] • Staled Longjing tea contains more acids, alcohols, aldehydes, and ketones. • Hexanoic acid and trans -2-nonenal are stale odor contributors in Longjing tea. • The stale odor contributors in Longjing tea exhibit a fatty odor. • The stale odor intensity can be predicted by the hexanoic acid concentration. • Hexanoic acid and trans -2-nonenal are degraded from linoleic acid. Longjing tea is renowned for its fresh aroma and high value. However, during storage, the emergence of an off-flavor known as "stale odor" can significantly impact the flavor quality and economic benefits of Longjing tea. Yet, the specific volatiles responsible for this stale odor in Longjing tea remain unknown. In this study, Longjing tea samples with varying degrees of stale odor intensity were analyzed using simultaneous distillation extraction coupled with gas chromatography-mass spectrometry (SDE-GC–MS). Through odor activity value (OAV) and fractional omission testing, hexanoic acid and trans -2-nonenal were identified as the primary contributors to the stale odor. Moreover, the concentration of hexanoic acid was found to be valuable in predicting the intensity of the stale odor in Longjing tea. The oxidative degradation of linoleic acid was proved as the generation pathway of stale odor in Longjing tea. These findings provide essential theoretical principles for Longjing tea production and preservation. [ABSTRACT FROM AUTHOR]

Various types of malt quality profiles have been investigated to benefit the North American brewing industry. Herein, we report the development and brewing quality of the hulled, two-row malting barley (Hordeum vulgare L.) variety 'CDC Goldstar' lacking lipoxygenase-1 (LOX-1-less). This new variety offers a novel malt type for the improvement of beer flavor stability. The agronomic performance of 'CDC Goldstar' was tested in the Western Cooperative Two Row Barley Registration Trials during 2013-2014. In addition to high lodging tolerance, the new variety showed 6% higher yield than the current leading variety 'CDC Copeland'. The malt quality of 'CDC Goldstar' showed higher diastatic power and lower wort ß-glucan content than 'CDC Copeland' and controllable proteolytic modification (soluble nitrogen and Kolbach Index). Pilot- (100 L) and commercial-scale (5,000 L) brewing trials were conducted using 'CDC PlatinumStar', another LOX-1-less variety with a low enzymatic profile, as the control variety. Absence of the LOX-1 trait from 'CDC Goldstar' maintained trans-2-nonenal levels in aged beers as low as those in other LOX-1-less varieties without affecting major beer parameters, such as ester and aldehyde content or foam stability. The newly developed 'CDC Goldstar' malting barley provides added value for the beer industry and consumers. [ABSTRACT FROM AUTHOR]

Huanglongbing (HLB), a devastating citrus disease caused by Candidatus Liberibacter asiaticus, is efficiently vectored by the Asian citrus psyllid, Diaphorina citri Kuwayama (Hemiptera: Liviidae). Tamarixia radiata (Waterston) plays a crucial role as an ectoparasitoid, preying on D. citri nymphs. By collecting and identifying headspace volatiles from fifth instar nymphs of D. citri using a gas chromatograph-mass spectrometer (GC-MS), we obtained a collection of 9 volatile compounds. These compounds were subsequently chosen to investigate the electrophysiological and behavioral responses of female T. radiata. At a concentration of 10 μg/μl, 9 compounds were compared with cis-3-hexen-1-ol (control), resulting in trans-2-nonenal inducing the highest relative electroantennogram (EAG) value, followed by hexanal, heptanal, n-heptadecane, tetradecanal, n-tetradecane, n-pentadecane, 1-tetradecanol, and 1-dodecanol. The top 5 EAG responses of female T. radiata to these compounds were further investigated through EAG dose-response experiments. The results showed positive dose-responses as concentrations increased from 0.01 to 10 μg/μl. In Y-tube olfactometer bioassays, female T. radiata exhibited a preference for specific compounds. They were significantly attracted to tetradecanal at a concentration of 10 µg/µl and trans-2-nonenal at 0.01 µg/µl, while no significant attraction was observed toward hexanal, heptanal, or n-heptadecane. Our report is the first to demonstrate that volatiles produced by D. citri nymphs attract T. radiata, which suggests that this parasitoid may utilize nymph volatiles to locate its host., (© The Author(s) 2024. Published by Oxford University Press on behalf of Entomological Society of America.)

Carboxymethyl chitosan (CMCH) from native chitosan of high molecular weight (H, 310–375 kDa) was synthesized for improving water solubility. The water solubility of high-molecular-weight carboxymethyl chitosan (H-CMCH) was higher than that of native chitosan by 89%. The application of H-CMCH as enhancing the moisturizer in mangosteen extract deodorant cream was evaluated. Different concentrations of H-CMCH (0.5–2.5%) were investigated in physicochemical characteristics of creams, including appearance, phase separation, pH, and viscosity, by an accelerated stability test. The different degrees of skin moisturizing (DM) on pig skin after applying H-CMCH solution, compared with untreated skin, water, and propylene glycol for 15 and 30 min using a Corneometer®, were investigated. The results showed that the 0.5% H-CMCH provided the best DM after applying the solution on pig skin for 30 min. Trans-2-nonenal, as an unsatisfied odor component, was also evaluated against components of the mangosteen extract deodorant cream, which were compared to the standard, epigallocatechin gallate (EGCG). In addition, DPPH and ABTS radical scavenging activity, ferric reducing antioxidant power (FRAP), and antibacterial activities were examined for the mangosteen extract deodorant cream using 0.5% H-CMCH. Results indicated that the mangosteen extract synergized with H-CMCH, which had a good potential as an effective skin moisturizing agent enhancer, deodorizing activity on trans-2-nonenal odor, antioxidant properties, and antibacterial properties.

Recently, due to changes in consumer demand, a lot of attention has been paid to forecasting the quality of beer with long shelf life, as trade must have a clear understanding of the risks associated with its sales, as well as understand what parameters may change, affecting the shelf life and quality of this fermented drink. In this regard, scientific developments in the field of extending the shelf life and identifying substances that affect the stability of beer during storage are of big importance but are not currently defined by regulation. Such substances include phytosterols included in the lipid fraction of plant raw materials, which play an important role in technological processes of beer preparation and the formation of its taste. Control of phytosterols transformation processes, as factors that can affect the sensory stability of beer, can be used to predict stability of beer. [ABSTRACT FROM AUTHOR]

Trans-2-nonenal is a fatty aldehyde with a long-chain, containing nine carbons. It was known that trans-2-nonenal is a cause of the odor associated with aging, and mainly found from the ages of 40 years. Phage display was a famous laboratory technique for proteins, peptides, and DNA interaction using bacteriophages to connect proteins with the genetic information. In this study, we have carried out random phage display screening to identify specific binding peptides for trans-2-nonenal. Trans-2-nonenal was directly coated on the plate. To select the phages against trans-2-nonenal, the random phages were attached to trans-2-nonenal and selected by 1–5 panning steps. Individual DNA of phage after 5 panning was analyzed to find the specific peptide sequence against trans-2-nonenal. The affinity of positive and negative binding phages was verified by ELISA assay using M13 phage-specific antibody. Among the phages, the phage with sequence of AHKSKLHQHVMFGGG (called as P4) in the end of tail, has shown the highest response. To explore a role of the peptide selected in sequence analysis and ELISA assay, the peptide was connected to magnetic beads. The peptide-coated beads were treated within trans-2-nonenal: treatment of P4 peptide shows significant decrease of trans-2-nonenal compared to negative peptide. Based on our results, it is suggested that the peptide, which is selected by phage display, could be used for the removal of trans-2-nonenal and odor associated with aging. [ABSTRACT FROM AUTHOR]

In general, beer degradation is evaluated by sensory test; however, it depends on the subjectivity of an inspector. Therefore, it is highly required that an objective evaluation method is developed. It has been clarified that the degradation degree of beer proceeds mainly by oxidation of components derived from malt and formation of nonelectrolyte trans‐2‐nonenal. In this study, we developed LB film taste sensor using metal complex for evaluating the degradation degree of beer with trans‐2‐nonenal concentrations. In addition, the physical properties of three metal electrodes and sensing film surface were evaluated with AFM and FT‐IR, and these results and the sensor response characteristics were compared and discussed for improving the sensitivity as a sensor for beer degradation evaluation. [ABSTRACT FROM AUTHOR]

Abstract The lipoxygenase-1-null (LOX-less) trait has positive effects on beer quality, and in particular, improvement of flavor stability by reduction of beer deteriorating substances such as trans -2-nonenal (T2N). 'SouthernStar' was successfully developed as the first LOX-less malting barley variety in Australia by introducing LOX-less trait into 'Flagship' by successive backcross and molecular marker assisted selection (MMAS). 'Flagship' is a two-rowed malting barley variety in Australia and it was used as the recurrent parent for the successive backcrossing. The yield potential, agronomic performance, disease resistance and the general malting quality were almost identical between 'SouthernStar' and 'Flagship'. To evaluate effects of LOX-less trait on beer quality, the brewing trials were conducted using a pilot-scale brewing apparatus. The wort and beer quality were similar between 'SouthernStar' and 'Flagship'. The effect of the LOX-less trait on the reduction of beer deteriorating substances such as T2N and trihydroxyoctadecenoic acid (THOD) contents was clearly verified in this study. The scores for total staleness of the test beers were significantly lower than those of the control beers under several storage conditions in one trial. Highlights • A new lipoxygenase-1-less (LOX-less) malting barley variety 'SouthernStar' developed by backcrossing. • Similar agricultural characteristics and malting quality as a recurrent parent 'Flagship'. • Reduction of trihydroxyoctadecenoic acid (THOD) and trans -2-nonenal (T2N) contents in beer by LOX-less trait introduced. • Improvement of flavor stability evaluated by sensory analysis for stale beer. [ABSTRACT FROM AUTHOR]

The molecule 2-nonenal is renowned as the origin of unpleasant human aging-related body odor that can potentially indicate age-related metabolic changes. Most 2-nonenal measurements rely on chromatographic analytical systems, which pose challenges in terms of daily usage and the ability to track changes in concentration over time. In this study, we have developed liquid- and gas-phase biosensors (bio-sniffers) with the aim of enabling facile and continuous measurement of trans -2-nonenal vapor. Initially, we compared two types of nicotinamide adenine dinucleotide (phosphate) [NAD(P)]-dependent enzymes that have the catalytic ability of trans -2-nonenal: aldehyde dehydrogenase (ALDH) and enone reductase 1 (ER1). The developed sensor quantified the trans -2-nonanal concentration by measuring fluorescence (excitation: 340 nm, emission: 490 nm) emitted from NAD(P)H that was generated or consumed by ALDH or ER1. The ALDH biosensor reacted to a variety of aldehydes including trans -2-nonenal, whereas the ER1 biosensor showed high selectivity. In contrast, the ALDH bio-sniffer showed quantitative characteristics for trans -2-nonenal vapor at a concentration range of 0.4-7.5 ppm (with a theoretical limit of detection (LOD) and limit of quantification (LOQ) of 0.23 and 0.26 ppm, respectively), including a reported concentration (0.85-4.35 ppm), whereas the ER1 bio-sniffer detected only 0.4 and 0.8 ppm. Based on these findings, headspace gas of skin-wiped alcohol-absorbed cotton collected from study participants in their 20s and 50s was measured by the ALDH bio-sniffer. Consequently, age-related differences in signals were observed, suggesting the potential for measuring trans -2-nonenal vapor.

The unsaturated aldehyde trans -2-nonenal is known to be generated by lipid peroxidation at the surface of the skin in an aging-related manner and has harmful effects on keratinocytes in the skin. In this study, the protective effect of a Lycii Radicis Cortex (LRC) extract against trans -2-nonenal-induced cell damage on human keratinocyte cell lines (HaCaT) was investigated. Notably, treatment with the LRC extract resulted in an increase in cell survival, while trans -2-nonenal decreased the viability of HaCaT cells. For identification of interaction between the LRC extract and trans -2-nonenal, this mixture was incubated in simulated physiological conditions, showing a strong decrease in the amount of trans -2-nonenal by the LRC extract. Subsequent LC-ESI-MS analysis revealed that kukoamine B (KB) formed Schiff base-derived pyridinium adducts with trans -2-nonenal. Thus, these results suggest that KB could be a potential agent that may protect HaCaT cells by forming new products with trans -2-nonenal.

In this research the effect of total packaging oxygen on the quality of bottled (glass bottle) lager beer during storage was studied. The beer was stored in a dark room at temperature of 22 - 25°C and it contained three different concentrations of total packaging oxygen: 0,09, 0,29 and 0,63 mg/L. During the 98 days storage period the concentration of trans-2-nonenal, a well known indicator of oxidation processes in the beer, was monitored. The results obtained in this research clearly show that the concentration of trans-2-nonenal is not directly related to the total oxygen concentration in the bottled beer. Sensory analysis of beer was also performed and obtained results clearly show that higher concentrations of total packaging oxygen directly effects beer quality and flavour. [ABSTRACT FROM AUTHOR]

Trans-2-nonenal is an aldehyde contributing to an unpleasant off-flavor and odor of rancid butter in stored beer. The automated solid-phase microextraction technique (SPME) coupled with gas chromatography (GC) and solid-phase dynamic extraction (SPDE) coupled with gas chromatography were optimized and introduced to determine trans-2-nonenal in barley, malt and beer. Five types of SPME fibers coated with different stationary phases (100 μm PDMS, 65 μm PDMS/DVB, 85 μm CAR/PDMS, 50/30 μm DVB/CAR/PDMS, 85 μm PA) and two needles (PDMS, PDMS/AC) were compared and tested for their efficiencies in the headspace (HS) SPME and SPDE determination of trans-2-nonenal in barley, malt and beer. The highest extraction efficiency of HS-SPME was achieved with the PDMS/DVB fiber, and addition of 1.5 g of NaCl, extraction time was 20 min at 60 °C. The highest extraction efficiency of HS-SPDE was obtained with the PDMS needle, 15 extraction strokes at 60 °C and addition of 1.5 g of NaCl. Trans-2-nonenal was identified with the method of HS-SPME coupled gas chromatography-mass spectrometry (GC-MS); the samples were analyzed using the HS-SPME-GC-coupled gas chromatography-flame ionization detector (GC-FID) technique. [ABSTRACT FROM AUTHOR]

Crystalline precipitates of pea amylose with selected food flavour compounds: hexanal, trans-2-nonenal and trans-2, 4-decadienal, were obtained through a controlled method of heating at 80°C and slowly cooling. Amylose from pea starch was prepared by precipitation with l-butanol after aqueous leaching at 70°C. The amylose-flavour precipitates were examined by light microscopy, differential scanning calorimetry and X-ray diffraction. The crystallinity of the complexes followed the order: amylose-hexanal > amylose-trans-2-nonenal > amylose-trans-2,4-decadienal, demonstrated by: the dimension of the crystals, the melting temperatures and enthalpies, the Bragg angles (20) and distances d (nm). The crystalline structure of the amylose-hexanal complex, determined by X-ray diffraction, was assigned to be V61 type. The amylose- trans-2-nonenal showed intermediate characteristics with a tendency to the V611 form and the conformation of the trans- trans-2,4-decadienal chain seems to preclude full inclusion. [ABSTRACT FROM AUTHOR]

Carboxymethyl chitosan (CMCH) from native chitosan of high molecular weight (H, 310–375 kDa) was synthesized for improving water solubility. The water solubility of high-molecular-weight carboxymethyl chitosan (H-CMCH) was higher than that of native chitosan by 89%. The application of H-CMCH as enhancing the moisturizer in mangosteen extract deodorant cream was evaluated. Different concentrations of H-CMCH (0.5–2.5%) were investigated in physicochemical characteristics of creams, including appearance, phase separation, pH, and viscosity, by an accelerated stability test. The different degrees of skin moisturizing (DM) on pig skin after applying H-CMCH solution, compared with untreated skin, water, and propylene glycol for 15 and 30 min using a Corneometer®, were investigated. The results showed that the 0.5% H-CMCH provided the best DM after applying the solution on pig skin for 30 min. Trans-2-nonenal, as an unsatisfied odor component, was also evaluated against components of the mangosteen extract deodorant cream, which were compared to the standard, epigallocatechin gallate (EGCG). In addition, DPPH and ABTS radical scavenging activity, ferric reducing antioxidant power (FRAP), and antibacterial activities were examined for the mangosteen extract deodorant cream using 0.5% H-CMCH. Results indicated that the mangosteen extract synergized with H-CMCH, which had a good potential as an effective skin moisturizing agent enhancer, deodorizing activity on trans-2-nonenal odor, antioxidant properties, and antibacterial properties. [ABSTRACT FROM AUTHOR]

The transfusion of packed red blood cells (PRBCs) is a significant risk to blood recipients. Blood banking procedures permit the storage of PRBCs for up to 42 days. Storage of PRBCs can cause polymorphonuclear granulocytes (PMNs) activation and the development of neutrophil-mediated transfusion-related acute lung injury. The aim of our study was to determine if PRBC storage has an influence on the formation of arachidonic acid (AA) and advanced glycation end products (AGEs). Twenty units of PRBCs were used to measure AA and AGE levels. The samples were taken on the 0th, 14th, 28th, and 42nd days of PRBC storage. The AA level was analyzed by gas-liquid chromatography-mass spectrometry and AGE level by an immunoenzymatic test. During the first 14 days of PRBC storage, the AA level significantly increased and then slowly decreased. The AGE level increased continuously during the whole time of the study. In a model experiment, the AA glycoxidation product trans-2-nonenal (T2N) formed adducts in reaction with hemoglobin which were detectable with the test for AGE. It is highly probable that the observed increase in AGE level is related to the decrease in AA in PRBCs, which can be associated with the formation of toxic aldehydes, especially T2N and 4-hydroxynonenal (HNE), from AA. Glucose in the PRBCs (preservative solution) can contribute to AGE formation as well. The formation of AGEs, HNE, and T2N in PRBCs, their influence on PMNs in vitro, and confirmation of our assumption need further studies. [ABSTRACT FROM AUTHOR]

Abstract: Protein-tyrosine phosphatases (PTPs) are very susceptible to oxidation by reactive oxygen species (ROS), which induce the oxidation of catalytic cysteines, thereby inactivating these PTPs. PTPs are also inactivated by treatment with different aldehydes (such as trans-2-nonenal), produced after tissue damage by ROS. However, the molecular mechanisms behind such aldehyde-due inactivation remain unknown. Using commercially available compounds, we examined the structural characteristics of trans-2-nonenal that allow the inhibition of platelet membrane-associated PTP activity, as well as how these compounds affect the dynamics of SH–, CO– and NH2– protein groups on the membranes. PTP was effectively inhibited by physiological amounts of trans-2-nonenal (1–10 μM). Incubation with trans-2-nonene (10 μM) also decreased PTP activity, although to a lower extent. Treatment with nonyl aldehyde almost eliminated PTP inhibition. Decreases in protein thiols were visible after trans-2-nonenal and trans-2-nonene treatments. Both the latter compounds also increased protein carbonyls (although trans-2-nonenal was more effective) and decreased protein amino groups to an equal extent. Collectively, our data indicate that α,β unsaturation (and not a double bond in another position) is the most important structural determinant for PTP inhibition, the alkenal with 9-carbon atoms being the most effective in eliciting such inhibition. The data allow us to predict the modification of sulfhydryls and/or the formation of addition products with lysyl or histidyl residues, and hence the kind of specific antibodies that it would be necessary to generate in order to test such modifications directly. [Copyright &y& Elsevier]

Various types of malt quality profiles have been investigated to benefit the North American brewing industry. Herein, we report the development and brewing quality of the hulled, two-row malting barley ( Hordeum vulgare L.) variety 'CDC Goldstar' lacking lipoxygenase-1 (LOX-1-less). This new variety offers a novel malt type for the improvement of beer flavor stability. The agronomic performance of 'CDC Goldstar' was tested in the Western Cooperative Two Row Barley Registration Trials during 2013-2014. In addition to high lodging tolerance, the new variety showed 6% higher yield than the current leading variety 'CDC Copeland'. The malt quality of 'CDC Goldstar' showed higher diastatic power and lower wort β-glucan content than 'CDC Copeland' and controllable proteolytic modification (soluble nitrogen and Kolbach Index). Pilot- (100 L) and commercial-scale (5,000 L) brewing trials were conducted using 'CDC PlatinumStar', another LOX-1-less variety with a low enzymatic profile, as the control variety. Absence of the LOX-1 trait from 'CDC Goldstar' maintained trans -2-nonenal levels in aged beers as low as those in other LOX-1-less varieties without affecting major beer parameters, such as ester and aldehyde content or foam stability. The newly developed 'CDC Goldstar' malting barley provides added value for the beer industry and consumers., (Copyright © 2021 by JAPANESE SOCIETY OF BREEDING.)

The oxidation of trans-2-nonenal, the main compound causing staleness in beer, with a membrane fraction of acetic acid bacteria was investigated. For use of the fraction, it was necessary to inactivate membrane-bound alcohol dehydrogenase (ADH) first to avoid oxidation of alcohol, while maintaining membrane-bound aldehyde dehydrogenase (ALDH) activity. ADH was completely inactivated by treatment of the membrane fraction at 60°C for 15 min, without any loss of ALDH activity. ALDH activity was not affected by heat treatment even in the presence of 10% alcohol. Results of HPLC showed that a fraction incubated at 60°C for 15 min oxidized 50 ppb trans-2-nonenal added to a commercial beer sample without affecting the alcohol content. Our sensory panel found that the stale odor of trans-2-nonenal disappeared when the membrane fraction was so treated, with the resulting odor better than that of beer with trans-2-nonenal added but not treated with the fraction.