Dienoic Acid Research Articles

Template-Directed Selective Photodimerization Reactions of 5-Arylpenta-2,4-dienoic Acids.

We developed an efficient method that enables selective photodimerization of 5-arylpenta-2,4-dienoic acids (i.e., vinylogous cinnamic acids). The use of 1,8-dihydroxynaphthalene as a template ensures proximity of the two reacting olefins so that irradiation of template-bound dienoic acids gives mono [2 + 2] cycloaddition products in good to excellent yields (up to 99%), as single regioisomers, and with high diastereoselectivities (dr = 3:1 to 13:1). The geometrical and stereochemical features of compounds 12a, 16a, and 22a were analyzed by X-ray crystallography.

Revisiting polar paradox: antioxidant activity in bulk oil using selected phenol lipids.

The purpose of this work was to re-evaluate the polar paradox theory (PPT) that explains the relationships between the efficacy of antioxidants, their polarity, and their environments. In this study, ascorbic acid (AA), ascorbyl palmitate (AP), gallic acid (GA), gallyl palmitate (GP), Trolox (TR), α-tocopherol (TO), resveratrol (R), and resveratryl palmitate (RP) were employed to assess conjugated dienoic acid (CDA), the p-anisidine value (p-AV), headspace oxygen content, and hexanal formation in a bulk oil system. TR, TO, R, and RP showed better antioxidant activities in CDA and p-AV and higher headspace oxygen content than AA, AP, GA, and GP. AA showed lower hexanal formation than AP, whereas GP, TO, and RP had better antioxidant activity than their derivatives. These findings suggest that the PPT might be useful to explain the oxidation that occurs at the air-oil interface/association colloids but applying it to other assays might not appropriate.

Photocatalytic Radical Decarboxylation [4 + 3] Annulation Reactions of Lactones via Dienoic Acid EDA Complexes

Photocatalytic Radical Decarboxylation [4 + 3] Annulation Reactions of Lactones via Dienoic Acid EDA Complexes

(5Z,9Z)-14-[(3,28-Dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic Acid with Cytotoxic Activity

For the first time, a synthetic analogue of natural (5Z,9Z)-dienoic acid has been synthesized in the form of a hybrid molecule containing a fragment of oleanolic acid and (5Z,9Z)-tetradeca-5.9-dienedicarboxylic acid, synthesized using a new reaction of Ti-catalyzed homo-cyclomagnesiation 1,2-dienes. The high cytotoxic activity of (5Z,9Z)-14-[(3,28-dioxoolean-12-en-28-yl)oxy]tetradeca-5,9-dienoic acid against tumor cells Jurkat, K562, U937 and HL60 was established. This compound is also an inducer of apoptosis, affects the cell cycle and inhibits human topoisomerase I.

Sexual dimorphism in the gonad lipidome of blue mussels (Mytilus sp.): New insights from a global lipidomics approach

Blue mussels (Mytilus sp.) are an economically important species for European aquaculture. Their importance as a food source is expected to increase in the coming net-zero society due to their low environmental footprint; however, their production is affected by anthropogenic stressors and climate change. During reproduction, lipids are key molecules for mussels as they are the main source of energy on which newly hatched embryos depend in the first days of their development. In this work, blue mussels of different origins are analysed, focusing on the differences in lipid composition between the ovary (BMO) and the testis (BMT). The lipidome of blue mussel gonads (BMG) is studied here by combining traditional lipid profiling methods, such as fatty acid and lipid class analysis, with untargeted liquid chromatography-mass spectrometry (LC-MS) lipidomics. The approach used here enabled the identification of 770 lipid molecules from 23 different lipid classes in BMG. BMT, which consists of billions of spermatocytes, had greater amounts of cell membrane and membrane lipid components such as FA18:0, C20 polyunsaturated fatty acids (PUFA), free sterols (ST), ceramide phosphoethanolamines (CerPE), ceramide aminoethylphosphonates (CAEP), cardiolipins (CL), glycerophosphocholines (PC), glycerophosphoethanolamines (PE) and glycerophosphoserines (PS). In BMO, saturated fatty acids (FA14:0 and FA16:0), monounsaturated fatty acids (MUFA) and other storage components such as C18-PUFA accumulated in triradylglycerolipids (TG) and alkyldiacylglycerols (neutral plasmalogens, TG O-), which, together with terpenes, wax esters and cholesterol esters, make up most of oocytes yolk reserves. BMO also had higher levels of ceramides (Cer) and generally alkyl/alkenyl glycerophospholipids (mainly plasmanyl/plasmenyl PC), suggesting a role for these lipids in vitellogenesis. Non-methylene interrupted dienoic fatty acids (NMID FA), typically found in plasmalogens, were the only membrane-forming PUFA predominantly detected in BMO. The results of this study are of great importance for clarifying the lipid composition of BMG and provide an important basis for future studies on the reproductive physiology of these organisms.

A review of Zanthoxylum chalybeum Engl: Ethnomedicinal uses, pharmacology, phytochemistry and toxicology

Background: Zanthoxylum chalybeum Engl. is a traditional medicinal plant, which is native to Eastern and Southern Africa. Commonly known as the ‘Knob wood’, it has been used for centuries by several traditional healers in Kenya, Tanzania, Uganda, Zambia and Zimbabwe. The species is very well known to local communities by its common names such as ‘Kundanyoka’ (Shona), ‘Mjafari’ (Swahili) and ‘Ntaleyedungu’ (Uganda), and it grows naturally in the tropics and subtropics.Aim: The present review describes information on the ethnomedicinal uses, phytochemical constituents, pharmacology and toxicology of Z. chalybeum.Method: Collection of data was based on literature research from several sources including electronic databases such as Google scholar, Web of Science, Science Direct, Pubmed, books, book chapters and theses.Results: Z. chalybeum is widely used in the treatment of malaria, cancer and diabetes. Pharmacological studies revealed that crude extracts and some isolated chemical compounds from Z. chalybeum demonstrated biological activities such as antibacterial, antidiabetic and antimalarial activities. Studies in phytochemical analysis of Z. chalybeum revealed the presence of new compounds such as 6-benzo (1, 3) dioxol-5-yl-hexa-2,5 dienoic acid isobutylamide, 4-methoxy-N-(2-methoxy-phenyl)-N methyl-benzamide, N-(2-hydroxy-methyl-propyl)-3 phenyl-acrylamide and 4-(isoprenyloxy)-3-methoxy,4-deoxymethylenedioxyfagaramide. Toxicology studies revealed moderate to high toxicity, depending on the type of cells and the extraction solvent used.Conclusion: Z. chalybeum is a valued medicinal plant used in Eastern and Southern Africa.Contribution: The properties of Z. chalybeum revealed in previous studies can be used to guide research scientists in future drug formulations.

Conjugated Dienoic Acid Peroxides as Substrates in Chaetopterus Bioluminescence System.

Biochemistry of bioluminescence of the marine parchment tubeworm Chaetopterus has been in research focus for over a century; however, the results obtained by various groups contradict each other. Here, we report the isolation and structural elucidation of three compounds from Chaetomorpha linum algae, which demonstrate bioluminescence activity with Chaetopterus luciferase in the presence of Fe2+ ions. These compounds are derivatives of polyunsaturated fatty acid peroxides. We have also obtained their structural analogues and demonstrated their activity in the bioluminescence reaction, thus confirming the broad substrate specificity of the luciferase.

Direct synthesis of a new hybrid molecules based on isomerically pure 5<i>Z</i>,9<i>Z</i>-dienoic acids and monocarbonyl derivatives of curcuminoids

Synthesis of previously undescribed hybrid compounds based on monocarbonyl derivatives of curcumin and 5 Z ,9 Z -dienoic acids with yields of 61-67% was carried out for the first time. Unsaturated acids are synthesized using at the key stage of stereoselective reaction of intermolecular cross-cyclomagnesiation of aliphatic and O-containing 1,2-dienes catalyzed by Cp2TiCl2.

Proposed Resolution of a Mechanistic Puzzle of Long Duration: Self-Condensation of Cyclopentanone to Form an 11-Carbon Dienoic Acid

The mechanism proposed for the transformation of cyclopentanone to the dienoic acid 1, as published in this journal, is revealed to be in error. We show that carbon 11 derives not from dimethyl sulfoxide as proposed but from the dichloromethane present in the "quenching" solution. The intermediacy of an α-chloromethyl ketone and its subsequent fragmentation in the presence of a hydroxide ion is supported by experiments described herein and by extensive literature precedent.

식물성 유지 및 수중유적형 유화계에서 육두구 종자 에탄올 추출물의 항산화활성 평가

The antioxidant ability of 80% ethanolic extract of nutmeg seed (NM80) was evaluated using in vitro assays and bulk oil and oil-in-water (O/W) emulsion matrices. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) cation radical scavenging, and oxygen radical antioxidant capacity (ORAC) in vitro assays were used to evaluate the antioxidant ability of the extract. The DPPH radical scavenging activities of 25, 50, 100, and 200 μg/mL NM80 were 12.5, 20.9, 35.1, and 62.8%, respectively, while the ABTS cation radical scavenging activities were 2.7, 6.5, 30.5, and 29.8%, respectively, demonstrating a dose-dependent effect. The ORAC value was significantly higher at an NM80 concentration of 25 μg/mL than the positive control (p<0.05). The conjugated dienoic acid (CDA), ρ-anisidine, and tertiary butyl alcohol values in 90-min-heated corn oil containing 200 ppm of NM80 were significantly reduced by 3.26, 16.94, and 17.34%, respectively, compared to those for the sample without NM80 (p<0.05). However, the headspace oxygen content and CDA value in the O/W emulsion containing 200 ppm of NM80 at 60°C had 6.29 and 82.85% lower values, respectively, than those for the sample without NM80 (p<0.05). The major volatile compounds of NM80 were allyl phenoxyacetate, eugenol acetate, and eugenol. NM80 could be an effective natural antioxidant in lipid-rich foods in bulk oil or O/W emulsion matrix.

Use of (E,E)-Dienoic Acids as Switchable (E,E)- and (Z,E)-Dienyl Anion Surrogates via Ligand-Controlled Palladium Catalysis.

Carboxylic acids are not readily applied as carbon-based nucleophiles due to their intrinsic acidic group. Here, we demonstrate that free (E,E)-2,4-dienoic acids form electron-neutral and highest occupied molecular orbital-raised η2-complexes with Pd(0) and undergo Friedel-Crafts-type additions to imines with exclusive α-regioselectivity, giving formal dienylated products after decarboxylation. Unusual and switchable (E,E)- and (Z,E)-selectivity, along with excellent enantioselectivity, is achieved via ligand-controlled outer-sphere or inner-sphere reaction modes, respectively, which are well supported by comprehensive density functional theory calculation studies. An unprecedented formal reductive Mannich reaction between (E,E)-dienoic acids and imines is also developed to furnish enantioenriched β-amino acid derivatives.

Notch Signaling Mediates Radiation-Induced Smooth Muscle Cell Hypermuscularization and Cerebral Vasculopathy.

Emerging evidence highlighted vascular injury in aggravating radiation-induced brain injury (RIBI), a common complication of radiotherapy. This study aimed to delineate the pathological feature of cerebral small vessel and investigate the functional roles of Notch signaling in RIBI. Brain tissue and functional MRI from RIBI patients were collected and analyzed for radiation-induced vasculopathy. A RIBI mouse model was induced by a single dose of 30-Gy cranial irradiation. Vascular morphology, pulsatility, and reactivity to pharmacological interventions, such as nimodipine and 20-hydroxyeicosa-6(Z),15(Z)-dienoic acid, were monitored by 2-photon imaging in mice at 6 weeks postirradiation. Western blot, real-time quantitative PCR, immunofluorescence staining, and behavioral tests were performed. The effect of N-[N-(3, 5-difluorophenacetyl)-l-alanyl]-s-phenylglycinet-butyl ester, a Notch inhibitor, was used to investigate the vascular pathogenesis of RIBI mouse model. Morphologically, radiation resulted in vascular malformation featured by focal contractile rings together with general stenosis. Functionally, radiation also led to hypoperfusion, attenuated vascular pulsatility, and decreased dilation to nimodipine and 20-hydroxyeicosa-6(Z),15(Z)-dienoic acid. Mechanically, Notch activation and increased expression of α-SMA protein were found in both surgical specimens of RIBI patients and the irradiated mice. Importantly, Notch inhibition by N-[N-(3, 5-difluorophenacetyl)-l-alanyl]-s-phenylglycinet-butyl ester significantly alleviated cerebral hypoperfusion, vasculopathy, and cognitive deficits in the RIBI mouse model. Radiation-induced cerebral vasculopathy showed bead-like shape and increased contractile state. Inhibition of Notch signaling by N-[N-(3, 5-difluorophenacetyl)-l-alanyl]-s-phenylglycinet-butyl ester effectively attenuated vasculopathy and relieved cognitive impairment, suggesting Notch signaling as a therapeutic target for the treatment of RIBI.

Oriented bio-feeding control of the anaerobic biodegradation of ethinyl estradiol

Up to 95% of hormones are excreted into domestic wastewater with urine or feces, but their macromolecules are difficult to biodegrade. This project studies the treatment of Ethinyl Estradiol (EE2) in swine wastewater in an Upstream Solids Reactor (USR), and explores a new method for oriented bio-feeding to regulate the anaerobic biodegradation process. It was found that the metabolism of lactic acid and propionic acid was accompanied by changes in EE2 content, but lactic acid molecules were not readily bioavailable, so adding propionic acid was more suitable. However, controlling the pH to lower (4.73) and higher (8.73) values inhibited further fermentation of acetic acid and propionic acid, which was not favorable for the removal of EE2. This is simply due to the fact that propionic acid as a carbon source changes the preference of the microbes for consuming EE2. The order of the effect of addition of propionic acid on the removal of EE2 was as follows: P400>P800>P0>P200 (addition of propionic acid). The P400 removal efficiency increased from 60% to 85%. In the metabolism of EE2, after oxidation, hydrolysis, ketosis, hydroxylation and enzymatic action, dienoic acid and oleic acid were generated, and there was no secondary pollution from EE2 metabolites. In conclusion, feeding microorganisms with propionic acid can enhance the anaerobic biodegradation of EE2, providing a new strategy for the anaerobic biodegradation and bioremediation of refractory pollutants.

Three new triterpenoid glycosides from Aronia melanocarpa (Michx.) Elliott

Three new triterpenoid glycosides, 2α,3α,23,24-tetrahydroxyurs-12,19- dien-oic acid 28-O-β- D -glucopyranoside (1), 2α,3β,23,24-tetrahydroxyurs-12, 19(29) -dien-28-oic acid 28-O-β- D -glucopyranoside (2), and 2α,3β,23,24-tetrahydroxyurs-12, 18-dien-28-oic acid 28-O-β- D -glucopyranoside (3) were isolated from Aronia melanocarpa (Michx.) Elliott. Their structures were elucidated by extensive spectroscopic methods. All the isolated compounds displayed moderate inhibitory activity against nitric oxide production in macrophages.

Lepidium meyenii (Maca) Roots: UPLC-HRMS, Molecular Docking, and Molecular Dynamics

Lepidium meyenii or Maca is widely cultivated as a health care food supplement due to its nutritional and medicinal properties. Although there are a few in-depth studies evaluating Maca antihypertensive effects, the correlations between the chemical constituents and bioactivity of the plant have not been studied before. Thus, the roots were extracted using different solvents (aqueous, methanol, 50% methanol, and methylene chloride) and investigated for their antihypertensive and antioxidant activities through several in vitro assays. The methanolic extract exhibited the best renin and angiotensin converting enzyme (ACE) inhibitory activities with IC50 values of 24.79 ± 1.3 ng/mL and 22.02 ± 1.1 ng/mL, respectively, along with the highest antioxidant activity. In total, 120 metabolites from different classes, e.g., alkylamides, alkaloids, glucosinolates, organic acids, and hydantoin derivatives, were identified in the methanolic extract using ultrahigh-performance liquid chromatography/high-resolution mass spectrometry (UPLC/HRMS). Molecular docking simulations were used to investigate the potential binding modes and the intermolecular interactions of the identified compounds with ACE and renin active sites. Glucotropaeolin, β-carboline alkaloids, succinic acid, and 2,4-dihydroxy-3,5-cyclopentyl dienoic acid showed the highest affinity to target the ACE with high docking scores (S ranging from −35.32 to −22.51 kcal mol–1) compared to lisinopril (S = −36.64 kcal mol–1). Interestingly, macamides displayed the greatest binding affinity to the active site of renin with docking scores (S ranging from −22.47 to −28.25 kcal mol–1). Further, β-carbolines achieved docking scores comparable to that of the native ligand (S ranging from −13.50 to −20.06 kcal mol–1). Molecular dynamics simulations and MMPBSA were also carried out and confirmed the docking results. Additionally, the computational ADMET study predicted that the compounds attaining promising docking results had proper pharmacokinetics, drug-likeness characteristics, and safe toxicological profiles. Ultimately, our findings revealed that Maca roots could be considered a promising candidate as an antihypertensive drug.

Studies to Explain Further, Why Percentages of Eicosanoid Precursor Fatty Acids Associate Positively in Chicken Muscle

Background: Polyunsaturated fatty acids with 20 or 22 carbon atoms are precursors of eicosanoids and docosanoids, which are important regulatory molecules in cell physiology. In breast muscle of chickens, we recently reported that percentages of these precursors were positively associated. Subsequently, we observed that the concentration ranges of the fatty acids seemed to cause the positive associations, e.g. between %EPA (eicosapentaenoic acid, 20:5: n3) and %AA (arachidonic acid, 20:4 n6). Aim: To explain further correlations between relative amounts of eicosanoid and docosanoid precursors. Methods: Typically, the precursors had low numbers and low variability, as compared with the predominant fatty acids, such as oleic acid (18:1 c9). We first present considerations concerning associations in general between relative amounts of three positive scale variables, two of which (A, B) having narrow ranges relative to the third one (C). Next, we show results of computer experiments to test the reasoning. Results and Discussions: We made S = A + B + C, i.e. %A + %B + %C = 100. %A correlated positively with %B, whereas %A (%B) related negatively to %C. The particular ranges of A, B, and C seemed to explain these associations. We found that slope of %A (abscissa) vs. %B approached B/A. Furthermore, slope of %A (abscissa) vs. %C approached –(1 +B/A), and that of %B (abscissa) vs. %C was near –(1+ A/B). We also show equations of regression lines concerning associations between A (B, C) percentages of S, when ranges of A and B are narrow relative to C. Finally, we compare slope values obtained by the formulas, and by linear regression. Conclusions: We suggest that Intended Ranges of eicosanoid precursor fatty acids might have arisen through evolutionary selection, thereby causing Distribution Dependent Correlations, mathematically. Possibly, this selection could improve the balance between eicosanoids (docosanoids). Definitions and Abbreviations: Variability: the width or spread of a distribution, measured e.g. by the range and standard deviation. Distribution: graph showing the frequency distribution of a variable within a particular range. In this article, we also use distribution when referring to a particular range, a – b, on the scale. Uniform distribution: every value within the range is equally likely. In this article, we may write “Distributions of A, B, and C were a - b, c - d, and e - f, respectively”. OA = Oleic Acid (18:1 c9); LA = Linoleic Acid (18:2 n6); ALA = Alpha Linolenic Acid (18:3 n3); AA = Arachidonic Acid (20:4 n6); EPA = EicosaPentaenoic Acid (20:5 n3); DPA = DocosaPentaenoic Acid (22:5 n3); DHA = Docosa Hexaenoic Acid (22:6 n3); DGLA= Dihomo Gamma Linolenic Acid (20:3 n6); EDA = Eicosa Dienoic Acid (20:2 n6); ETA = Eicosa Trienoic acid (20:3 n3).

Synthesis and Investigation of Novel CHCA-Derived Matrices for Matrix-Assisted Laser Desorption/Ionization Mass Spectrometric Analysis of Lipids.

A significant area of study and upgrading for increasing sensitivity and general performances of matrix-assisted laser-desorption ionization (MALDI) mass spectrometry (MS) is related to matrix design. Several efforts have been made to address the challenge of low-mass-region interference-free for metabolomics analysis and specifically for lipidomics. To this aim, rationally designed matrices as 4-chloro-α-cyanocinnamic acid (ClCCA) were introduced and reported to provide enhanced analytical performances. We have taken this rational design one step further by developing and optimizing new MALDI matrices with a range of modifications on the CHCA core, involving different functionalities and substituents. Of particular interest was the understanding of the electron-withdrawing (e.g., nitro-) or donating (e.g., methoxy-) effects along with the extent of conjugation on the ionization efficiency. In the present work, ten matrices were designed on a reasonable basis, synthesized, and characterized by NMR and UV spectroscopies and laser desorption ionization. With the assistance of these putative MALDI matrices, samples containing phospholipids (PL), and neutral di-/tri-acylglycerols (DAG, TAG) were investigated using milk, fish, blood, and human plasma extracts. In comparison with CHCA and ClCCA, four of them, viz. [(2E,4E)-2-cyano-5-(4-methoxyphenyl)penta-2,4-dienoic acid] (1), [(2E,4E)-2-cyano-5-(4-nitrophenyl)penta-2,4-dienoic acid] (2), [(E)-2-cyano-3-(6-methoxynaphthalen-2-yl)acrylic acid] (6) and [(E)-2-cyano-3-(naphthalen-2-yl)acrylic acid] (7) displayed good to even excellent performances as MALDI matrices in terms of ionization capability, interference-free spectra, S/N ratio, and reproducibility. Especially compound 7 (cyano naphthyl acrylic acid, CNAA) was the election matrix for PL analysis and matrix 2 (cyano nitrophenyl dienoic acid, CNDA) for neutral lipids such as DAG and TAG in positive ion mode.

Photostable Abscisic Acid Agonists with a Geometrically Rigid Cyclized Side Chain.

The plant hormone abscisic acid (ABA) plays a central role in adaptive responses to abiotic stresses that adversely affect crop growth and productivity. However, ABA photoinstability limits its use in agriculture. To overcome this drawback, in this study, we developed photostable ABA analogues, the (+)-BP2A compound series (compounds 5-9), in which the dienoic acid side chain of ABA was replaced with phenylacetic acid. All BP2A analogues showed higher stability against UV-B irradiation at 302 nm than ABA, and compounds 6 and 7 barely decomposed even under sunlight. In physiological assays, (+)-BP2A and (+)-compound 7, in which the α,β-unsaturated carbonyl group of BP2A was reduced, exhibited ABA-like activities, including inhibition of seed germination and induced drought tolerance in Arabidopsis. Biochemical studies revealed that (+)-compound 7, unlike (+)-BP2A, did not activate pyrabactin resistance-like (PYL) receptors in vitro and was converted to (+)-BP2A in plants, suggesting that it functions as a prodrug PYL agonist. Furthermore, (+)-compound 7 inhibited seed germination of tomato, lettuce, and rice. Thus, this compound represents a potential plant growth regulator that induces ABA-type responses in agricultural fields.

Synthesis of conjugated dienes via palladium-catalysed aerobic dehydrogenation of unsaturated acids and amides.

A Pd(II)-catalyzed direct aerobic dehydrogenation of γ,δ-olefinic acids and amides has been demonstrated. The present protocol dehydrogenates the least acidic amides and acids, thus replacing the traditional enolate strategy for dehydrogenation. A broad spectrum of conjugated dienamides and dienoic acids were produced in good to excellent yields. A possible reaction mechanism was proposed and supported by deuterium labelling studies.

Oxidative stability of chia seed oil and flax seed oil and impact of rosemary (Rosmarinus officinalis L.) and garlic (Allium cepa L.) extracts on the prevention of lipid oxidation

Chia seed and flax seed oils are rich in polyunsaturated fatty acids, but are susceptible to oxidative deterioration. The aim of this study was to determine the oxidative stability of chia seed and flax seed oils and enhance the stability using rosemary or garlic extracts. During accelerated storage at 65 °C for 14 days, the antioxidant abilities of rosemary or garlic extracts were evaluated and compared with those of butylated hydroxy toluene, ascorbyl palmitate, and α-tocopherol using peroxide value, conjugated dienoic acids, free fatty acid, thiobarbituric acid value analysis. The profile of volatiles, fatty acid composition, and the tocopherol contents in the treated and/or untreated oils were also determined. Active ingredients of rosemary and garlic extracts were also determined. Rosemary extract was found to provide higher oxidative stability than garlic extract after 14 days in most assays (e.g., the CDA values of 4.8% for rosemary extract and 5.2% for garlic extract in chia seed oil). The contents of γ-tocopherol, linoleic acid, and α-linolenic acid were well retained in the functional oils treated with the two extracts. After accelerated storage, the content of the major odor-active volatiles varied based on the type of oil. Our findings show the potential of natural aromatic plant extracts with respect to improving the oxidative stability of functional oils.