Oxidation Of Oleic Acid Research Articles

Chronic treatment with terbutaline increases glucose and oleic acid oxidation and protein synthesis in cultured human myotubes

ObjectiveIn vivo studies have reported several beneficial metabolic effects of β-adrenergic receptor agonist administration in skeletal muscle, including increased glucose uptake, fatty acid metabolism, lipolysis and mitochondrial biogenesis. Although these effects have been widely studied in vivo, the in vitro data are limited to mouse and rat cell lines. Therefore, we sought to discover the effects of the β2-adrenergic receptor agonist terbutaline on metabolism and protein synthesis in human primary skeletal muscle cells. MethodsHuman cultured myotubes were exposed to terbutaline in various concentrations (0.01–30 ​μM) for 4 or 96 ​h. Thereafter uptake of [14C]deoxy-D-glucose, oxydation of [14C]glucose and [14C]oleic acid were measured. Incorporation of [14C]leucine, gene expression by qPCR and proteomics analyses by mass spectrometry by the STAGE-TIP method were performed after 96 ​h exposure to 1 and 10 ​μM of terbutaline. ResultsThe results showed that 4 ​h treatment with terbutaline in concentrations up to 1 ​μM increased glucose uptake in human myotubes, but also decreased both glucose and oleic acid oxidation along with oleic acid uptake in concentrations of 10–30 ​μM. Moreover, administration of terbutaline for 96 ​h increased glucose uptake (in terbutaline concentrations up to 1 ​μM) and oxidation (1 ​μM), as well as oleic acid oxidation (0.1–30 ​μM), leucine incorporation into cellular protein (1–10 ​μM) and upregulated several pathways related to mitochondrial metabolism (1 ​μM). Data are available via ProteomeXchange with identifier PXD024063. ConclusionThese results suggest that β2-adrenergic receptor have direct effects in human skeletal muscle affecting fuel metabolism and net protein synthesis, effects that might be favourable for both type 2 diabetes and muscle wasting disorders.

SENP2 is vital for optimal insulin signaling and insulin-stimulated glycogen synthesis in human skeletal muscle cells

Sentrin-specific protease (SENP) 2 has been suggested as a possible novel drug target for the treatment of obesity and type 2 diabetes mellitus after observations of a palmitate-induced increase in SENP2 that lead to increased fatty acid oxidation and improved insulin sensitivity in skeletal muscle cells from mice. However, no precedent research has examined the role of SENP2 in human skeletal muscle cells. In the present work, we have investigated the impact of SENP2 on fatty acid and glucose metabolism as well as insulin sensitivity in human skeletal muscle using cultured primary human myotubes. Acute (4 ​h) oleic acid oxidation was reduced in SENP2-knockdown (SENP2-KD) cells compared to control cells, with no difference in uptake. After prelabeling (24 ​h) with oleic acid, total lipid content and incorporation into triacylglycerol was decreased, while incorporation into other lipids, as well as complete oxidation and β-oxidation was increased in SENP2-KD cells. Basal glucose uptake (i.e., not under insulin-stimulated conditions) was higher in SENP2-KD cells, whereas oxidation was similar to control myotubes. Further, basal glycogen synthesis was not different in SENP2-KD myotubes, but both insulin-stimulated glycogen synthesis and AktSer473 phosphorylation was completely blunted in SENP2-KD cells. In conclusion, SENP2 plays an important role in fatty acid and glucose metabolism in human myotubes. Interestingly, it also appears to have a pivotal role in regulating myotube insulin sensitivity. Future studies should examine the role of SENP2 in regulation of insulin sensitivity in other tissues and in vivo, defining the potential for SENP2 as a drug target.

A Short Method for the Synthesis of Hydroxyoleic Acids

AbstractEnzymatic or microbiological oxidation of oleic acid can afford azelaic acid as a building block for bioplastics. However, during the oxidation, the formation of hydroxylated byproducts is observed. To better follow the oxidation reaction, the availability of reference compounds is of great importance. To this aim, the synthesis of a series of oleic acids hydroxylated at ω ‐ 1, ω ‐ 2, ω ‐ 3 positions is described without the use of protecting groups. The final products are obtained by partial lactone reduction to hydroxyaldehyde followed by Grignard addition, selective oxidation of the primary hydroxyl group, and Wittig reaction.

Effect of fatty acids on the flavor formation of fish sauce

An appropriate fish model helps track changes of lipid and fatty acid during fermentation. Here we selected three freshwater fish (Culter alburnus, Carassius auratus and Ietalurus Punetaus) as the fermentative materials of fish sauce due to their significantly different contents of lipid and unsaturated fatty acid. The electronic nose showed that the flavor profiles of sauce samples prepared with different fish were dramatically different. A total of 71 volatile compounds of fish sauce were detected by solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC/MS). Then nine key flavor compounds, including 3-methylbutanal, 3-methyl-1-butanol, 3-(methylthio)propanal, 1-octen-3-ol, phenylacetaldehyde, nonanal, dimethyl trisulfide, decanal and hexanol, were screened based on odor activity values. According to correlation analysis between fatty acid profiles and fish sauce aroma, possible pathways of oleic acid (C18:1) and linoleic acid (C18:2) oxidation were suggested: oleic acid undergone the auto-oxidation to mainly form 10- hydroperoxide and 11- hydroperoxide, and (or) secondary form 8-hydroperoxide, then converted to nonanal, octanal and decanal; linoleic acid undergone the enzymatic oxidation to form 10-L(S)-hydroperoxy-cis-9, trans-11-octadecadieuoic acid, then converted to 1-octen-3-ol.

Substrate oxidation in primary human skeletal muscle cells is influenced by donor age

Primary human myotubes represent an alternative system to intact skeletal muscle for the study of human diseases related to changes in muscle energy metabolism. This work aimed to study if fatty acid and glucose metabolism in human myotubes in vitro were related to muscle of origin, donor gender, age, or body mass index (BMI). Myotubes from a total of 82 donors were established from three different skeletal muscles, i.e., musculus vastus lateralis, musculus obliquus internus abdominis, and musculi interspinales, and cellular energy metabolism was evaluated. Multiple linear regression analyses showed that donor age had a significant effect on glucose and oleic acid oxidation after correcting for gender, BMI, and muscle of origin. Donor BMI was the only significant contributor to cellular oleic acid uptake, whereas cellular glucose uptake did not rely on any of the variables examined. Despite the effect of age on substrate oxidation, cellular mRNA expression of pyruvate dehydrogenase kinase 4 (PDK4) and peroxisome proliferator–activated receptor gamma coactivator 1 alpha (PPARGC1A) did not correlate with donor age. In conclusion, donor age significantly impacts substrate oxidation in cultured human myotubes, whereas donor BMI affects cellular oleic acid uptake.

Effects of epoxy stearic acid on lipid metabolism in HepG2 cells.

In the present study, effects of cis-9,10-epoxystearic acid (ESA) generated by the thermal oxidation of oleic acid on HepG2 cells, including intracellular lipid accumulation, fatty acid composition, and lipid metabolism, were investigated. Our results revealed that ESA increased the number and size of cellular lipid droplets. Intracellular triacylglycerol and total cholesterol content demonstrated that ESA induced lipid accumulation in HepG2 cells in a dose- and time-dependent manner. Results of fatty acid composition further indicated that ESA could lead to intracellular lipid accumulation. Our results also revealed that ESA may suppress the fatty acid oxidation in peroxisomes and mitochondria, including PPARα, Cpt1α, and Acox1, whereas the expression of genes involved in lipid synthesis, including Srebp-1c and Scd1, was enhanced. These findings provide critical information on the effects of ESA on HepG2 cells, particularly lipid accumulation and metabolism, which is important for evaluating the biosafety of the oxidative product of oleic acid. PRACTICAL APPLICATION: The administration of cis-9,10-epoxystearic acid to HepG2 cells could lead to disorder of lipid metabolism of cells by enhancing the intracellular lipid content, as well as suppressing the fatty acid oxidation in peroxisomes and mitochondria. These findings could provide information for the evaluation of the biosafety of the oxidative product of oleic acid.

Synthesis of Branched Biolubricant Base Oil from Oleic Acid.

The mature manufacturing of synthetic lubricants (poly-α-olefins, PAO) proceeds through oligomerization, polymerization, and hydrogenation reactions of petrochemical ethylene. In this work, we utilize the inexpensive bio-derived oleic acid as raw material to synthesize a crotch-type C45 biolubricant base oil via a full-carbon chain synthesis without carbon loss. It contains several cascade chemical processes: oxidation of oleic acid to azelaic acid (further esterification to dimethyl azelate) and nonanoic acid (both C9 chains). The latter is then selectively hydrogenated to nonanol and brominated to the bromo-Grignard reagent. In a next step, a C45 biolubricant base oil is formed by nucleophilic addition (NPA) of excessive C9 bromo-Grignard reagent with dimethyl azelate, followed by subsequent hydrodeoxygenation. The specific properties of the prepared biolubricant base oil are almost equivalent to those of the commercial lubricant PAO6 (ExxonMobil). This process provides a new promising route for the production of value-added biolubricant base oils.

Effect of unsaturated fatty acids on glycation product formation pathways (Ⅰ) the role of oleic acid

Research on advanced glycation end-products (AGEs) and their formation pathways in food processing has gradually increased because AGEs are associated with human health, especially with involvement of lipids. In this study, radicals and glycation products were detected via electron spin resonance (ESR) and ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) respectively. The correlation of important intermediates was used to explain the effect of oleic acid (OA) on the glycation products and pathways. The results indicated OA participation decreased the content of stable radicals and glycosyl compounds in Maillard Reaction (MR). The oxidation of OA produced active radicals, and electron transfer caused lysine to transform radical form. These radicals participated in the formation of fructosyllysine (FL) with glucose (Glc) via the MR. The participation of OA is acted as inhibiting the way of Glc autoxidation and promoting the glycation pathway from FL to 3-deoxyglucosone (3-DG) to fluorescent-AGEs. Orthogonal projection to latent structures discriminant analysis results indicated that 3-DG, D-glucosone and methylglyoxal are key products in discriminating the glycation reaction.

The influence of SO2 as the Criegee intermediate scavenger on the heterogeneous oxidation of oleic acid

Abstract As a well-known Criegee intermediate (CI) scavenger, SO2 can react with CIs in the gas phase to form sulphuric acid, which can be further converted to sulfate aerosols, which make an important contribution to haze formation. Despite the potential importance, the interaction of SO2 with the CIs produced by heterogeneous oxidation of unsaturated fatty acids remains largely unclear. In this work, the heterogeneous reactions of oleic acid (OA) thin films with O3 and O3/SO2 mixture gases are studied under four different relative humidities (RHs): 5%, 30%, 60% and 80%, using microscopic Fourier transform infrared (micro-FTIR) spectrometer combined with a gas-flow system. A detailed comparison on formation rates of ester and intensity ratios of 1742 cm−1 band (envelope C O of ester) to 1712 cm−1 band (feature C O of carboxyl) between the two reaction systems shows that the addition of SO2 inhibits the conversion of carboxyl to ester at any RH. As the SO2 concentration increases, the formation rates and final relative amount of ester decrease. Based on these data, it can be concluded that SO2 consumes part condensed-phase CIs produced by ozonolysis of OA, resulting in a significant inhibition in ester formation. The present results provide an important atmospheric implication on the reaction between SO2 and condensed-phase CIs, which may be a missing sulfate production pathway in the atmosphere.

Pancreatic cancer cells show lower oleic acid oxidation and their conditioned medium inhibits oleic acid oxidation in human myotubes

Background/Objectives: We aimed to metabolically compare healthy primary human pancreatic epithelial cells (hPEC) to a pancreatic cancer cell line (PANC-1) and explore the effect on energy metabolism of exposing primary human myotubes to conditioned medium from hPEC and PANC-1 cells. MethodsDifferences in metabolism were examined with radiolabeled glucose, oleic acid and lactic acid, and by qPCR. Mass spectrometry-based proteomics was used to study global protein secretion from the two cell types. Pathway analyses were performed. ResultsPANC-1 cells tended to have higher glucose uptake, production of lactic acid, and glucose oxidation compared to hPEC cells. PANC-1 cells had higher uptake but lower oxidation of oleic acid, and mitochondrial reserve capacity from oleic acid was lower in PANC-1 cells. These differences in energy metabolism were reflected by differences in gene expressions and pathway analyses of the secretome. Conditioned medium from PANC-1 cells attenuated oleic acid oxidation in primary human myotubes. ConclusionsMetabolic characterization of the PANC-1 cells revealed a glycolytic phenotype since they had an active glucose oxidation. Furthermore, PANC-1 cells showed a lower oleic acid oxidation and secreted a high amount of proteins into conditioned medium that also induced a reduced oleic acid oxidation in myotubes.

Direct Biotransformation of Nonanoic Acid and Its Esters to Azelaic Acid by Whole Cell Biocatalyst of Candida tropicalis

Azelaic acid is an α,ω-dicarboxylic acid with nine carbons and has multiple applications in plastic and cosmetic industries. Chemical oxidation of oleic acid with ozone (called ozonolysis) allows t...

Reduction of Metal Ion Content in Jatropha Biodiesel by Ion Exchange

AbstractThis study is focused on the optimization and decreasing the metal ion content in jatropha biodiesel using an ion exchange resin. The changes in the organic composition of jatropha oil biodiesel were measured by GCMS before and after passing the biodiesel over the ion exchange resin. The chelating efficiency of ion exchange resin on metal ions, including potassium, calcium, sodium, and magnesium, in jatropha biodiesel either treated with different oleic acid content or having different oxidation degrees was evaluated. The results showed that the ion exchange resin can effectively decrease the metal ions content in jatropha biodiesel without producing harmful substances to environment and human body. Moreover, the increase in oleic acid content and oxidation in Jatropha biodiesel affects the ability of ion exchange resins to sequester metal ions.

Thermal Oxidation Rate of Oleic Acid Increased Dramatically at 140 °C Studied using Electron Spin Resonance and GC–MS/MS

AbstractThermal oxidation of oleic acid at high temperatures was studied using combination of electron spin resonance (ESR) spin‐trapping technique and solid phase microextraction (SPME)‐Gas chromatography‐mass spectrometry‐mass spectrometry (GC–MS/MS). Dimethyl pyridine N‐oxide (DMPO) was applied as the spin trap. Alkyl, alkoxyl, and oxidized DMPO adducts were identified in the experimental spectra. At 140 °C, the alkyl radical adduct was the major component, accounting for 63.89% of the total radical adducts. However, the alkoxyl radical adduct was the main radical adduct in the temperature range of 120 to 135 °C. The total amount of spins, a parameter to indicate radical concentrations, detected at 140 °C was nearly three times higher than that at 135 °C. And, the total amount of alkyl radical adducts was higher than that of alkoxyl radical adducts at 140 °C, which indicated a higher alkyl radical formation rate. Besides, a larger amount (10.30%) of oleic acid degraded at 140 °C than that at 135 °C with the detection of GC. More (E)‐2‐Decenal (plastic) and (E)‐2‐undecenal (herbaceous) formed affect the flavor of frying.

Establishing the impact of model surfactants on cloud condensation nuclei activity of sea spray aerosol mimics

Abstract. Surface-active compounds present in aerosols can increase their cloud condensation nuclei (CCN) activation efficiency by reducing the surface tension (σ) in the growing droplets. However, the importance of this effect is poorly constrained by measurements. Here we present estimates of droplet surface tension near the point of activation derived from direct measurement of droplet diameters using a continuous flow streamwise thermal gradient chamber (CFSTGC). The experiments used sea spray aerosol (SSA) mimics composed of NaCl coated by varying amounts of (i) oleic acid, palmitic acid or myristic acid, (ii) mixtures of palmitic acid and oleic acid, and (iii) oxidized oleic acid. Significant reductions in σ relative to that for pure water were observed for these mimics at relative humidity (RH) near activation (∼ 99.9 %) when the coating was sufficiently thick. The calculated surface pressure (π = σH2O − σobserved) values for a given organic compound or mixture collapse onto one curve when plotted as a function of molecular area for different NaCl seed sizes and measured RH. The observed critical molecular area (A0) for oleic acid determined from droplet growth was similar to that from experiments conducted using macroscopic solutions in a Langmuir trough. However, the observations presented here suggest that oleic acid in microscopic droplets may exhibit larger π values during monolayer compression. For myristic acid, the observed A0 compared well to macroscopic experiments on a fresh subphase, for which dissolution has an important impact. A significant kinetic limitation to water uptake was observed for NaCl particles coated with pure palmitic acid, likely as a result of palmitic acid (with coating thicknesses ranging from 67 to 132 nm) being able to form a solid film. However, for binary palmitic-acid–oleic-acid mixtures there was no evidence of a kinetic limitation to water uptake. Oxidation of oleic acid had a minor impact on the magnitude of the surface tension reductions observed, potentially leading to a slight reduction in the effect compared to pure oleic acid. A CCN counter was also used to assess the impact on critical supersaturations of the substantial σ reductions observed at very high RH. For the fatty-acid-coated NaCl particles, when the organic fraction (εorg) was > 0.90 small depressions in critical supersaturation were observed. However, when εorg < 0.90 the impact on critical supersaturation was negligible. Thus, for the fatty acids considered here, the substantial σ reductions observed at high RH values just below activation have limited impact on the ultimate critical supersaturation. A surface film model is used to establish the properties that surface-active organic molecules must have if they are to ultimately have a substantial impact on the activation efficiency of SSA. To influence activation, the average properties of surface-active marine-derived organic molecules must differ substantially from the long-chain fatty acids examined, having either smaller molecular volumes or larger molecular areas. The model results also indicate that organic-compound-driven surface tension depression can serve to buffer the critical supersaturation against changes to the organic-to-salt ratio in particles in which the organic fraction is sufficiently large.

Scavenging effect of pasipay (passiflora incarnate L.) on singlet oxygen generation and fatty acid photooxygenation.

Anthracene as a chemical probe is usually used to trap the singlet oxygen and then detection and quantification can be based on absorbance. In this study, oxidation of anthracene declared that rate of singlet oxygen quenching in the presence of pasipay (passiflora incarnate L.) as a natural antioxidant, 1,4 Diazabicyclo [2.2.2] octane (DABCO) as a well‐known singlet oxygen scavenger and highly effective synthetic antioxidants in food industry such as Butylated hydroxytoluene (BHT), Butylated hydroxyanisole (BHA), tert‐Butylhydroquinone (TBHQ) decreased in the order of DABCO >pasipay > TBHQ > BHT > BHA. On the other hand, lipid photooxidation is the undesirable chemical process in which singlet oxygen result in the peroxidation of fatty acids. The results of this study also showed that oleic acid oxidation with singlet oxygen in the presence of pasipay (contains 0.4576 mg flavonoid compounds) diminished about 11% which shows pasipay has an effective role to inhibit lipid peroxidation.

Catalyzing Cubic-to-Hexagonal Phase Transition in NaYF4 via Ligand Enhanced Surface Ordering

Phase-pure hexagonal lanthanide-doped NaYF4 nanocrystals possess enhanced luminescence properties due to their low phonon energy and chemical stability compared to their cubic phase counterpart. However, the phase-pure hexagonal NaYF4 nanoparticle forms only at high temperature (≥180 °C) and in the presence of certain ligands (e.g., oleic acid), whereas the cubic phase forms at a low reaction temperature. To this end, we report the low temperature (∼48 °C) synthesis of phase-pure hexagonal NaYF4 nanoparticles by converting cubic NaYF4 nanoparticles into the hexagonal phase through surface oxidation of oleic acid (C-18) ligand to azelaic acid (C-9). The mechanism behind the transformation is investigated using density functional theory (DFT) based studies. DFT studies reveal that the phase transformation from cubic → hexagonal phase involves a disorder → order phase transition since all cationic sites are occupied by either Na or Y in the cubic phase, while the hexagonal phase has a more ordered structure ...

A study of the catalytic behavior of phosphotungstic acid-modified Janus particles in a heterogeneous oil/water pickering emulsion system

An emulsion interface materialization method was used to obtain amphiphilic silica Janus nanoparticles. Reducing the photosynthesis of aquatic organisms after water pollution. PW12O403− was introduced onto Janus particles by ion exchange, and an amphiphilic particle emulsion catalyst (PWO-J) was prepared. Hydrogen peroxide was used as the oxygen source, and the amphiphilicty of the catalyst was used to assemble the catalyst at the Pickering emulsion interface. The PWO-J catalyst was found to exhibit very high catalytic activity toward the oxidation of oleic acid in water-in-oil systems. The results showed that PWO-J catalysis of oxidation had similar results as CTAB and phosphotungstic acid (control system) under the same conditions. The azelaic acid recovery rate was 86.7%, and PWO-J could be reused 4 times. A reaction mechanism was proposed, and the constructed model was used to calculate a reaction rate constant of 15.32 × 10−5L•mol−1•s−1 for the PWO-J system. The PWO-J system had a lower activation energy than the control system, showing that the catalytic oxidation of oleic acid into azelaic acid was more likely to occur in the PWO-J system.

Utilization of lactic acid in human myotubes and interplay with glucose and fatty acid metabolism

Once assumed only to be a waste product of anaerobe glycolytic activity, lactate is now recognized as an energy source in skeletal muscles. While lactate metabolism has been extensively studied in vivo, underlying cellular processes are poorly described. This study aimed to examine lactate metabolism in cultured human myotubes and to investigate effects of lactate exposure on metabolism of oleic acid and glucose. Lactic acid, fatty acid and glucose metabolism were studied in myotubes using [14C(U)]lactic acid, [14C]oleic acid and [14C(U)]glucose, respectively. Myotubes expressed both the MCT1, MCT2, MCT3 and MCT4 lactate transporters, and lactic acid was found to be a substrate for both glycogen synthesis and lipid storage. Pyruvate and palmitic acid inhibited lactic acid oxidation, whilst glucose and α-cyano-4-hydroxycinnamic acid inhibited lactic acid uptake. Acute addition of lactic acid inhibited glucose and oleic acid oxidation, whereas oleic acid uptake was increased. Pretreatment with lactic acid for 24 h did not affect glucose or oleic acid metabolism. By replacing glucose with lactic acid during the whole culturing period, glucose uptake and oxidation were increased by 2.8-fold and 3-fold, respectively, and oleic acid oxidation was increased 1.4-fold. Thus, lactic acid has an important role in energy metabolism of human myotubes.

Epoxy Stearic Acid, an Oxidative Product Derived from Oleic Acid, Induces Cytotoxicity, Oxidative Stress, and Apoptosis in HepG2 Cells.

In the present study, effects of cis-9,10-epoxy stearic acid (ESA) generated by the thermal oxidation of oleic acid on HepG2 cells, including cytotoxicity, apoptosis, and oxidative stress, were investigated. Our results revealed that ESA decreased the cell viability and induced cell death. Cell cycle analysis with propidium iodide staining showed that ESA induced cell cycle arrest at the G0/G1 phase in HepG2 cells. Cell apoptosis analysis with annexin V and propidium iodide staining demonstrated that ESA induced HepG2 cell apoptotic events in a dose- and time-dependent manner; the apoptosis of cells after treated with 500 μM ESA for 12, 24, and 48 h was 32.16, 38.70, and 65.80%, respectively. Furthermore, ESA treatment to HepG2 cells resulted in an increase in reactive oxygen species and malondialdehyde (from 0.84 ± 0.02 to 8.90 ± 0.50 nmol/mg of protein) levels and a reduction in antioxidant enzyme activity, including superoxide dismutase (from 1.34 ± 0.27 to 0.10 ± 0.007 units/mg of protein), catalase (from 100.04 ± 5.05 to 20.09 ± 3.00 units/mg of protein), and glutathione peroxidase (from 120.44 ± 7.62 to 35.84 ± 5.99 milliunits/mg of protein). These findings provide critical information on the effects of ESA on HepG2 cells, particularly cytotoxicity and oxidative stress, which is important for the evaluation of the biosafety of the oxidative product of oleic acid.

Nighttime oxidation of surfactants at the air–water interface: effects of chain length, head group and saturation

Abstract. Reactions of the key atmospheric nighttime oxidant NO3 with organic monolayers at the air–water interface are used as proxies for the ageing of organic-coated aqueous aerosols. The surfactant molecules chosen for this study are oleic acid (OA), palmitoleic acid (POA), methyl oleate (MO) and stearic acid (SA) to investigate the effects of chain length, head group and degree of unsaturation on the reaction kinetics and products formed. Fully and partially deuterated surfactants were studied using neutron reflectometry (NR) to determine the reaction kinetics of organic monolayers with NO3 at the air–water interface for the first time. Kinetic modelling allowed us to determine the rate coefficients for the oxidation of OA, POA and MO monolayers to be (2.8±0.7) × 10−8, (2.4±0.5) × 10−8and (3.3±0.6) × 10−8 cm2 molecule−1 s−1 for fitted initial desorption lifetimes of NO3 at the closely packed organic monolayers, τd, NO3, 1, of 8.1±4.0, 16±4.0 and 8.1±3.0 ns, respectively. The approximately doubled desorption lifetime found in the best fit for POA compared to OA and MO is consistent with a more accessible double bond associated with the shorter alkyl chain of POA facilitating initial NO3 attack at the double bond in a closely packed monolayer. The corresponding uptake coefficients for OA, POA and MO were found to be (2.1±0.5) × 10−3, (1.7±0.3) × 10−3 and (2.1±0.4) × 10−3, respectively. For the much slower NO3-initiated oxidation of the saturated surfactant SA we estimated a loss rate of approximately (5±1) × 10−12 cm2 molecule−1 s−1, which we consider to be an upper limit for the reactive loss, and estimated an uptake coefficient of ca. (5±1) × 10−7. Our investigations demonstrate that NO3 will contribute substantially to the processing of unsaturated surfactants at the air–water interface during nighttime given its reactivity is ca. 2 orders of magnitude higher than that of O3. Furthermore, the relative contributions of NO3 and O3 to the oxidative losses vary massively between species that are closely related in structure: NO3 reacts ca. 400 times faster than O3 with the common model surfactant oleic acid, but only ca. 60 times faster with its methyl ester MO. It is therefore necessary to perform a case-by-case assessment of the relative contributions of the different degradation routes for any specific surfactant. The overall impact of NO3 on the fate of saturated surfactants is slightly less clear given the lack of prior kinetic data for comparison, but NO3 is likely to contribute significantly to the loss of saturated species and dominate their loss during nighttime. The retention of the organic character at the air–water interface differs fundamentally between the different surfactant species: the fatty acids studied (OA and POA) form products with a yield of ∼ 20 % that are stable at the interface while NO3-initiated oxidation of the methyl ester MO rapidly and effectively removes the organic character ( ≤ 3 % surface-active products). The film-forming potential of reaction products in real aerosol is thus likely to depend on the relative proportions of saturated and unsaturated surfactants as well as the head group properties. Atmospheric lifetimes of unsaturated species are much longer than those determined with respect to their reactions at the air–water interface, so they must be protected from oxidative attack, for example, by incorporation into a complex aerosol matrix or in mixed surface films with yet unexplored kinetic behaviour.