These conjugates may create abnormalities in protein functioning or damage the DNA; hence, PUFAs have a higher probability of generating toxic compounds than any other fats. This higher level of toxicity and the fact that they are more bioavailable than primary lipid oxidation products make them the most likely to impact health negatively.

Acrolein 2-propenal is an unsaturated aldehyde produced through linoleic acid oxidation and is acknowledged as a high-priority toxic chemical AfTSaDR, Ismahil et al. The acrolein amount fed to mice was established by considering the daily acrolein intake of an average human, thus indicating a possibly harmful effect on the human body.

Crotonaldehyde 2-butenal is an unsaturated aldehyde that has been detected in various food systems, including fried chips, fish, meat, canola oil, and vegetables Earley et al. Crotonaldehyde led to liver damage and hepatic tumors by forming propanodeoxyguanosine adducts in DNA when rats were fed with crotonaldehyde Chung et al.

Although some studies showed harmful effects, the impact on the human body is uncertain due to the unknown daily intake of crotonaldehyde. According to Oarada et al. Because there is no data available on the daily intake of these compounds, the concentrations leading to biological abnormalities are controversial.

The food industry focuses on finding natural and affordable ways to minimize lipid oxidation to improve product quality and safety. Because various factors affect oxidation, many unique food systems require different antioxidant strategies.

The most effective ways are minimizing the oxygen exposure, decreasing the degree of fatty acid unsaturation, using free radical scavenging antioxidants, incorporating singlet oxygen quenchers, blocking light exposure, reducing storage temperature, and adding metal chelators Decker et al.

Applying the most suitable and powerful protection mechanisms is crucial in preventing any possible toxic biological impact on the human body. Although the food industry develops these protection mechanisms to produce foods of high quality, once consumers purchase and open foods, oxidation reactions are inevitable due to air exposure.

Many consumers purchase bulk food items that are not consumed rapidly and thus have a higher chance of becoming rancid due to the eventual loss of free radical scavenging antioxidants. In addition, consumers often do not recognize the foods have become rancid, further increasing their chance of ingesting lipid oxidation products.

Besides consuming oxidized lipids, lipid oxidation might also occur during the digestion process. Oxidation during digestion could be minimized if antioxidants such as tocopherols, ascorbic acid, and flavonoids are consumed simultaneously as food to reduce possible oxidation reactions in the gastrointestinal tract.

This supports the recommendations to consume more fruits and vegetables since they are high in these antioxidants. In addition, low-fat diets also decrease the risk of consuming lipid oxidation products Kanner, AfTSaDR — Agency for toxic substances and disease registry, Toxicological profile for acrolein August, Barden, L.

Lipid oxidation in low-moisture food: A review, Critical Reviews in Food Science and Nutrition , 56 15 , — FSTA Ge Chung, F. Induction of liver tumors in F rats by crotonaldehyde, Cancer Research , 46 3 , — Cohn, J. Oxidized fat in the diet, postprandial lipaemia and cardiovascular disease, Current Opinion in Lipidology , 13, 19— Decker, E.

Why does lipid oxidation in foods continue to be such a challenge? INFORM , 32 5 , 18— Oxidation in foods and beverages and antioxidant applications: Volume 1 Woodhead Publishing, Cambridge, Earley, J.

Esterbauer, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes, Free Radical Biology and Medicine , 11 1 , 81— Grootveld, M. In vivo absorption, metabolism, and urinary excretion of alpha, beta-unsaturated aldehydes in experimental animals.

Relevance to the development of cardiovascular diseases by the dietary ingestion of thermally stressed polyunsaturate-rich culinary oils, Journal of Clinical Investigation , 6 , — Ismahil, M. Chronic oral exposure to the aldehyde pollutant acrolein induces dilated cardiomyopathy, American Journal of Physiology-Heart and Circulatory Physiology , 5 , H—H Jenkinson, A.

The effect of increased intakes of polyunsaturated fatty acids and vitamin E on DNA damage in human lymphocytes, Faseb Journal , 13, — Kanazawa, K. Uptake of secondary autoxidation products of linoleic acid by the rat, Lipids , 20, — Kanner, J. Dietary advanced lipid oxidation endproducts are risk factors to human health, Molecular Nutrition and Food Research , 51 9 , — FSTA Aj Kim, S.

Lipophilic aldehydes and related carbonyl compounds in rat and human urine, Lipids , 34, — Lei, L. The lipid peroxidation product EKODE exacerbates colonic inflammation and colon tumorigenesis, Redox Biology , 42, Long, E.

Transhydroxyhexenal, a product of n-3 fatty acid peroxidation: make some room HNE, Free Radical Biology and Medicine , 49, 1—8. McClements, D. Lipid Oxidation in Oil-in-Water Emulsions: Impact of Molecular Environment on Chemical Reactions in Heterogeneous Food Systems, Journal of Food Science , 65 8 , — Oarada, M.

Degeneration of lympoid tissues in mice with the oral intake of low molecular weight compounds formed during oil autoxidation, Agricultural and Biological Chemistry , 52, — Sekirov, I.

Gut microbiota in health and disease, Physiological Reviews, 90 3 , — Vieira, S. FSTA Cf Ipek Bayram was awarded a Fulbright Scholarship in and is currently studying for her Ph.

in the Department of Food Science at the University of Massachusetts, Amherst. Her primary research focus is lipid oxidation and antioxidants, mainly on determining and analyzing synergistic antioxidant activity in food matrices to improve food quality and safety.

Eric A. Decker is a Professor in the Department of Food Science at the University of Massachusetts, Amherst. He actively conducts research to characterize mechanisms of lipid oxidation, antioxidant protection of foods, and the health implications of bioactive lipids.

Decker has authored over publications, and has been listed as one of the most highly cited scientists in agriculture according to Clarivate's Highly Cited Researchers Report. Dr Decker has served on various committees within the following institutions: FDA; Institute of Medicine; Institute of Food Technologists; USDA; and the American Heart Association.

FSTA is quality-checked by experts in food-related sciences and contains a wealth of interdisciplinary, food-focused information that you can trust. This makes it a great tool for researching published science on food lipid oxidation and so many other topics. The dataset can be refined using the 2, descriptors applied to the FSTA records by the science team during curation.

Example descriptors include: Acrolein, Antioxidative activity, Cytotoxicity, Gastrointestinal microflora, Hepatotoxicity, Hydroperoxides, Oxidative stress, Radical scavenging activity, ω-3 Fatty acids. Ground Floor, Wharfedale Road, Winnersh Triangle, Wokingham, Berkshire RG41 5RB. Contact Us. Trial FSTA.

FSTA FSTA Overview. Content Interdisciplinary Coverage. Check Indexed Journals. Journal Assessment. Access and training Accessing FSTA. User Training. Librarian Toolkit. Advisory Boards Faculty. Case Studies. FSTA with Full Text. Fatty acyl-carnitine molecules are then transported into the mitochondrial matrix in exchange for carnitine by carnitine:acylcarnitine translocase through an antiport mechanism.

The pool of carnitine available to this transporter depends on the functioning of carnitine:palmitoyltransferase II CPT II , which serves to convert acylcarnitine to fatty acyl CoA, trapping the molecules within the mitochondrial matrix.

In contrast to this involved, regulated transport mechanism, VLCFAs are not dependent on carnitine for transport into peroxisomes; the transport of branched-chain fatty acids destined for alpha-oxidation is similar to this process, and as previously mentioned, is substrate-dependent.

In a similar fashion to previous sections, the process and enzymatic steps of the beta-oxidation spiral will primarily undergo discussion with alternative oxidation pathways mentioned later as they pertain to and produce metabolic products destined for mitochondrial beta-oxidation.

Variations of fatty acid molecular structure and additional required enzymes will also be discussed. Mitochondrial beta-oxidation of fatty acids requires four steps, all of which occur in the mitochondrial matrix, to produce three energy storage molecules per round of oxidation, including one NADH, one FAD H2 , and one acetyl CoA molecule.

Step 1. The first enzyme required is called acyl CoA dehydrogenase, and as other enzymes involved in the handling of fatty acids, it is specific to chain length.

Members of this enzyme family include long-chain, medium-chain, and short-chain acyl CoA dehydrogenases LCAD , MCAD , and SCAD , respectively. These enzymes catalyze the formation of a trans double bond between the alpha and beta carbons on acyl CoA molecules by removing two electrons to produce one molecule of FAD H2 , which eventually accounts for 1.

Step 2. There is no energy production associated with this step. Step 3. Following hydration, the next step is carried out by beta-hydroxyl acyl CoA dehydrogenase; as the name implies, electrons and two protons are removed from the hydroxyl group, and the attached beta carbon to oxidize the beta carbon and produce a molecule of NADH.

Each molecule of NADH will result in the production of 2. Step 4. The final step in Beta oxidation involves cleavage of the bond between the alpha and beta carbon by CoASH. This step is catalyzed by beta-keto thiolase and is a thiolytic reaction.

The reaction produces one molecule of acetyl CoA and a fatty acyl CoA that is two carbons shorter. The process may repeat until the even chain fatty acid has completely converted into acetyl CoA. Steps 1 through 4 refer to the beta-oxidation of a saturated fatty acid with an even-numbered carbon skeleton.

Unsaturated fatty acids, such as oleate and linoleate , contain cis double bonds that must be isomerized to the trans configuration enoyl CoA isomerase or reduced at the expense of an NADPH molecule 2,4-dienoyl CoA reductase.

Odd-chain fatty acids undergo beta-oxidation in the same manner as even chain fatty acids; however, once a five-carbon chain remains, the final spiral of beta-oxidation will yield one molecule of acetyl CoA and one molecule of propionyl CoA. This three-carbon molecule can be enzymatically converted to succinyl CoA, forming a bridge between the TCA cycle and fatty acid oxidation.

VLCFA beta-oxidation in peroxisomes occurs by a process similar to mitochondrial beta-oxidation; however, some key differences exist, including the fact that different genes encode fatty acid oxidation enzymes in peroxisomes, which is significant in certain inborn errors of metabolism.

The remaining three steps are similar to the mitochondrial steps. Another notable difference involves the extent to which beta-oxidation occurs; it may occur to completion, ending in the production of acetyl CoA molecules that are able to enter the cytosol or be transported to the mitochondria bound to carnitine.

Branched-chain fatty acids also require additional enzymatic modification to enter the alpha-oxidation pathway within peroxisomes.

Phytanic acid, 3,7,11,tetramethylhexadecanoic acid, requires additional peroxisomal enzymes to undergo beta-oxidation.

Phytanic acid initially activates to phytanyl CoA; then, phytanyl CoA hydroxylase alpha-hydroxylase , encoded by the PHYH gene, introduces a hydroxyl group to the alpha carbon. Pristanic acid undergoes beta-oxidation, which produces acetyl CoA and propionyl CoA in alternative rounds.

As with peroxisomal beta-oxidation of VLCFAs, this process generally ends when the carbon chain length reaches carbons, at which point the molecule is shuttled to the mitochondria by carnitine for complete oxidation to carbon dioxide and water.

Omega-oxidation of fatty acids in the endoplasmic reticulum primarily functions to hydroxylate and oxidize fatty acids to dicarboxylic acids to increase water solubility for excretion in the urine.

This enzymatic conversion relies on the cytochrome P superfamily to catalyze this reaction between xenobiotic compounds and molecular oxygen. Listed below are a few select diseases that either directly involve defective fatty acid metabolism through intrinsic enzyme deficiencies or indirectly prevent the proper functioning of fatty acid metabolism through extrinsic enzyme deficiencies.

Many, but not all, deficiencies of enzymes involved in fatty acid oxidation result in abnormal neurological development and or function early in life; a brief list of signs and symptoms appears under the selected diseases mentioned. Medium-chain acyl dehydrogenase is the most common inherited defect of fatty acid oxidation in humans; as one would expect, medium-chain carbon molecules accumulate in this disease.

Clinical manifestations of MCAD deficiency primarily present during fasting conditions and include lethargy, weakness, diaphoresis, and hypoketotic hypoglycemia, most commonly in children under the age of 5.

These abundant molecules then undergo oxidation by the cytochrome P system involved in omega-oxidation, resulting in dicarboxylic acidemia and dicarboxylic aciduria.

Zellweger syndrome results from autosomal recessive mutations in the PEX genes; these DNA sequences code for peroxin proteins, which are involved in the assembly of peroxisomes. Many different fatty acid compounds can accumulate without the oxidative machinery of peroxisomes, including VLCFAs and phytanic acid.

X-ALD is a genetic deficiency of the ABCD transporters in the membrane of peroxisomes, as mentioned previously, resulting in the pathological accumulation of VLCFAs within cells and is most clinically significant when the ABCD1 transporter is absent.

The disease presents with neurodegenerative and adrenal abnormalities. Refsum disease results from a genetic deficiency of the enzyme phytanyl CoA 2-hydroxylase, which, as previously mentioned, is involved in the alpha-oxidation of phytanic acid, a breakdown product of chlorophyll.

Disclosure: Jacob Talley declares no relevant financial relationships with ineligible companies. Disclosure: Shamim Mohiuddin declares no relevant financial relationships with ineligible companies.

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Author Information and Affiliations Authors Jacob T. Affiliations 1 Lincoln Memorial University DeBusk College of Osteopathic Medicine. Introduction Oxidation of fatty acids occurs in multiple regions of the cell within the human body; the mitochondria, in which only beta-oxidation occurs; the peroxisome, where alpha- and beta-oxidation occur; and omega-oxidation, which occurs in the endoplasmic reticulum.

Fundamentals Mitochondrial beta-oxidation can be used to supply acetyl CoA to two separate pathways, depending on which tissue oxidation occurs.

Cellular Level Important concepts pertaining to the regulation of mitochondrial beta-oxidation, cellular handling, and transport of fatty acids will be discussed here. Molecular Level In a similar fashion to previous sections, the process and enzymatic steps of the beta-oxidation spiral will primarily undergo discussion with alternative oxidation pathways mentioned later as they pertain to and produce metabolic products destined for mitochondrial beta-oxidation.

Clinical Significance Listed below are a few select diseases that either directly involve defective fatty acid metabolism through intrinsic enzyme deficiencies or indirectly prevent the proper functioning of fatty acid metabolism through extrinsic enzyme deficiencies.

MCAD Deficiency Medium-chain acyl dehydrogenase is the most common inherited defect of fatty acid oxidation in humans; as one would expect, medium-chain carbon molecules accumulate in this disease. Zellweger Syndrome Zellweger syndrome results from autosomal recessive mutations in the PEX genes; these DNA sequences code for peroxin proteins, which are involved in the assembly of peroxisomes.

Review Questions Access free multiple choice questions on this topic. Comment on this article. References 1. Houten SM, Violante S, Ventura FV, Wanders RJ. The Biochemistry and Physiology of Mitochondrial Fatty Acid β-Oxidation and Its Genetic Disorders.

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J of Appl Physiol. Download references. Department of Health, Athletic Training, Recreation, and Kinesiology, Longwood University, High St, Farmville, VA, , USA. Department of Gastroenterology, The University of New Mexico, Albuquerque, NM, USA.

You can also search for this author in PubMed Google Scholar. Correspondence to Troy Purdom. TP currently has accepted abstracts with ACSM, NSCA, and ISSN in the area of fat metabolism, athletic performance evaluation, energy expenditure, and body composition.

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Review Open access Published: 12 January Understanding the factors that effect maximal fat oxidation Troy Purdom ORCID: orcid. Abstract Lipids as a fuel source for energy supply during submaximal exercise originate from subcutaneous adipose tissue derived fatty acids FA , intramuscular triacylglycerides IMTG , cholesterol and dietary fat.

Background Lipids are the substrate largely responsible for energy supply during submaximal exercise [ 1 , 2 , 3 ]. Lipid oxidation Lipolysis Triacylglycerol TAG is the stored form of fat found in adipocytes and striated muscle, which consists of a glycerol molecule a three-carbon molecule that is bound to three fatty acid FA chains.

Fatty acid transport Limitations to FAox are due in part to a multi-faceted delivery system that has a series of regulatory events [ 18 ]. Within-cell FA transport into mitochondrion Within the cell, FA chain type and length have been shown to determine oxidative rates within the mitochondrion largely due to transport specificity [ 31 ].

Full size image. Conclusion In summary, FAox is contingent on many factors which can modify cellular expression in a short amount of time.

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This Hydroxyhydroperoxide Mechanism generates HNE by beta-scission of a key hydroxyalkoxyl radical that is produced from a hydroxy hydroperoxide 7.

Formation of the hydroxy hydroperoxide could involve hydrogen abstraction from an intermediate HODE. We note that an intramolecular H• transfer is geometrically favorable vide infra , bolstering the likelihood of such a mechanism.

Besides HNE, the beta-scission also would generate a vinyl radical that delivers a vinyl peroxy radical by reaction with oxygen, and ultimately provides 9-oxononanoic acid ONA via ONA enol. I nterestingly, an enzymatic route to these same products from LA was reported recently 8.

Thus, 9-HPODE, generated by the action of lipoxygenase on LA, is cleaved by the action of a hydroperoxide lyase to produce ONA and 3 Z -nonenal Enzymatic Pathway. Alkenal oxygenase promoted oxygenation of this b,g -unsaturated aldehyde then delivers HNE.

W e postulated 9 a Peroxycyclization-Dioxetane Fragmentation Mechanism that predicts a competition between peroxycyclization, that leads to aldehyde fragmentation products, and H• transfer that produces the hydroperoxy ODAs HPODE and 9-HPODE.

This scenario contrasts with that envisioned in the other mechanisms proposed for HNE generation that all consider one or the other of these hydroperoxides to be intermediates leading to HNE.

However, this difference between the mechanisms could easily be hidden if H• transfer is readily reversible. Thus, hydroperoxides could serve as a reservoir of peroxy radicals if H• abstraction from the hydroperoxy oxygen occurs readily.

This is exemplified by the use of a hydroperoxide as the precursor for a peroxy radical in a Peroxycyclization Model Study presented below. P eroxycyclization of an intermediate 5-peroxyeicosatetraenoyl radical followed by fragmentation of a dioxetane intermediate is a possible Peroxycyclization Route to OV-PC from AA-PC.

The hypothetical alternative pathways outlined above illustrate the potential competition for various isomeric pentadienyl and peroxyeicosatetraenoyl radical intermediates that may be crucial for a thorough understanding of factors influencing the generation and evolution of the end products of free radical-induced lipid oxidation.

A s noted above, we recently postulated a possible mechanism for oxidative fragmentation of lipids: peroxycyclization to generate a dioxetane intermediate that fragments to generate two carbonyl groups 9. Contemporaneously, this mechanism was recognized by others, and a model study was reported see Peroxycyclization Model Study in which one-electron oxidation of an allylic hydroperoxide produces acetone and chemiluminescence, presumably by cyclization of an alkylperoxyl radical to a dioxetane radical and subsequent dioxetane fragmentation that generates triplet acetone The generation of excited state carbonyl product is especially noteworthy as it is an expected consequence of orbital symmetry considerations.

This observation strongly supports the involvement of a dioxetane fragmentation because there is ample precedent for this unique phenomenon.

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