erucic acids


Summary: cis-13-Docosenoic Acids. 22-Carbon monounsaturated, monocarboxylic acids.

Top Publications

  1. Qiu D, Morgan C, Shi J, Long Y, Liu J, Li R, et al. A comparative linkage map of oilseed rape and its use for QTL analysis of seed oil and erucic acid content. Theor Appl Genet. 2006;114:67-80 pubmed
    ..The results provide new insights into the genetic control of seed oil and erucic acid content in oilseed rape, and demonstrate the utility of the linkage map and population. ..
  2. Moser H. Therapy of X-linked adrenoleukodystrophy. NeuroRx. 2006;3:246-53 pubmed
    ..Application of these interventions requires careful assessment of the patients' phenotype, which often changes over time. Family screening provides important opportunities for disease prevention...
  3. Katavic V, Mietkiewska E, Barton D, Giblin E, Reed D, Taylor D. Restoring enzyme activity in nonfunctional low erucic acid Brassica napus fatty acid elongase 1 by a single amino acid substitution. Eur J Biochem. 2002;269:5625-31 pubmed
    ..Thus, for the first time, the low erucic acid trait in canola B. napus can be attributed to a single amino acid substitution which prevents the biosynthesis of the eicosenoic and erucic acids.
  4. Wu G, Wu Y, Xiao L, Li X, Lu C. Zero erucic acid trait of rapeseed (Brassica napus L.) results from a deletion of four base pairs in the fatty acid elongase 1 gene. Theor Appl Genet. 2008;116:491-9 pubmed
    ..The four base pair deletion proved to be a mutation responsible for the low erucic acid trait in rapeseed and independent from the point mutation reported by Han et al. (Plant Mol Biol 46:229-239, 2001). ..
  5. Lemeshko V, Kugler W. Synergistic inhibition of mitochondrial respiration by anticancer agent erucylphosphohomocholine and cyclosporin A. J Biol Chem. 2007;282:37303-7 pubmed
    ..Our findings provide new insight into the mechanisms by which these unusual alterations of mitochondria might be involved in anticancer activity of alkylphosphocholines. ..
  6. van Geel B, Assies J, Haverkort E, Koelman J, Verbeeten B, Wanders R, et al. Progression of abnormalities in adrenomyeloneuropathy and neurologically asymptomatic X-linked adrenoleukodystrophy despite treatment with "Lorenzo's oil". J Neurol Neurosurg Psychiatry. 1999;67:290-9 pubmed
    ..Furthermore, the oil often induced adverse effects. Therefore, it is advocated that "Lorenzo's oil" should not be prescribed routinely to patients with X-ALD who already have neurological deficits. ..
  7. Kaushik N, Agnihotri A. GLC analysis of Indian rapeseed-mustard to study the variability of fatty acid composition. Biochem Soc Trans. 2000;28:581-3 pubmed
    ..Work is in progress at TERI (New Delhi, India) to utilize these lines for development of strains with particular fatty acid compositions for specific purposes. ..
  8. Wang N, Wang Y, Tian F, King G, Zhang C, Long Y, et al. A functional genomics resource for Brassica napus: development of an EMS mutagenized population and discovery of FAE1 point mutations by TILLING. New Phytol. 2008;180:751-65 pubmed publisher
    ..The procedure was applied to 1344 M2 plants, with 19 mutations identified, of which three were functionally compromised with reduced seed erucic acid content. ..
  9. Rahman M, Sun Z, McVetty P, Li G. High throughput genome-specific and gene-specific molecular markers for erucic acid genes in Brassica napus (L.) for marker-assisted selection in plant breeding. Theor Appl Genet. 2008;117:895-904 pubmed publisher
    ..2 SNP marker was integrated. These three kinds of high throughput molecular markers have been successfully implemented in our canola/rapeseed breeding programs. ..

More Information


  1. Moser H, Moser A, Hollandsworth K, Brereton N, Raymond G. "Lorenzo's oil" therapy for X-linked adrenoleukodystrophy: rationale and current assessment of efficacy. J Mol Neurosci. 2007;33:105-13 pubmed
    ..We also present current efforts to provide definitive evaluation of its clinical efficacy and discuss its possible role in the new therapeutic opportunities that will arise if newborn screening for X-ALD is validated and implemented. ..
  2. Mahmood T, Ekuere U, Yeh F, Good A, Stringam G. RFLP linkage analysis and mapping genes controlling the fatty acid profile of Brassica juncea using reciprocal DH populations. Theor Appl Genet. 2003;107:283-90 pubmed
    ..Epistatic interactions were observed between the QTLs E1a and LN(2). The stability of the detected QTLs across years and locations, and breeding strategies for improving the fatty acid profile of B. juncea, are discussed. ..
  3. Kugler W, Veenman L, Shandalov Y, Leschiner S, Spanier I, Lakomek M, et al. Ligands of the mitochondrial 18 kDa translocator protein attenuate apoptosis of human glioblastoma cells exposed to erucylphosphohomocholine. Cell Oncol. 2008;30:435-50 pubmed
  4. Golovko M, Murphy E. Uptake and metabolism of plasma-derived erucic acid by rat brain. J Lipid Res. 2006;47:1289-97 pubmed
    ..These results demonstrate for the first time that intact 22:1n-9 crosses the BBB, is incorporated into specific lipid pools, and is chain-shortened. ..
  5. Handrick R, Rübel A, Faltin H, Eibl H, Belka C, Jendrossek V. Increased cytotoxicity of ionizing radiation in combination with membrane-targeted apoptosis modulators involves downregulation of protein kinase B/Akt-mediated survival-signaling. Radiother Oncol. 2006;80:199-206 pubmed
    ..Our data suggest a role for inhibition of PKB/Akt-mediated anti-apoptotic signaling in increased efficacy of the combination. ..
  6. Su Z, Wang T, Shrivastava N, Chen Y, Liu X, Sun C, et al. Piriformospora indica promotes growth, seed yield and quality of Brassica napus L. Microbiol Res. 2017;199:29-39 pubmed publisher
    ..These results demonstrated that P. indica played an important role in enhancing plant growth, rapeseed yield and quality improvement of B. napus. ..
  7. Liu J, Sabeva N, Bhatnagar S, Li X, Pujol A, Graf G. ABCD2 is abundant in adipose tissue and opposes the accumulation of dietary erucic acid (C22:1) in fat. J Lipid Res. 2010;51:162-8 pubmed publisher
    ..In conclusion, D2 is a sterol regulatory element binding protein target gene that is highly abundant in fat and opposes the accumulation of dietary lipids generally absent from the triglyceride storage pool within adipose tissue...
  8. Lu J, Barron Casella E, Deering R, Heinzer A, Moser A, deMesy Bentley K, et al. The role of peroxisomal ABC transporters in the mouse adrenal gland: the loss of Abcd2 (ALDR), Not Abcd1 (ALD), causes oxidative damage. Lab Invest. 2007;87:261-72 pubmed
  9. Yi X, Gauthier K, Cui L, Nithipatikom K, Falck J, Campbell W. Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries. Am J Physiol Heart Circ Physiol. 2007;292:H2265-74 pubmed
    ..Our results suggest a role of adrenic acid metabolites, specifically, DH-EETs as endothelium-derived hyperpolarizing factors in the coronary circulation. ..
  10. Cheng B, Wu G, Vrinten P, Falk K, Bauer J, Qiu X. Towards the production of high levels of eicosapentaenoic acid in transgenic plants: the effects of different host species, genes and promoters. Transgenic Res. 2010;19:221-9 pubmed publisher
  11. Deon M, Wajner M, Sirtori L, Fitarelli D, Coelho D, Sitta A, et al. The effect of Lorenzo's oil on oxidative stress in X-linked adrenoleukodystrophy. J Neurol Sci. 2006;247:157-64 pubmed
    ..Therefore, it may be presumed that antioxidants should be considered as an adjuvant therapy for X-ALD patients. ..
  12. Ji T, Liu C, Wang A, Yang J, Su Y, Yuan L, et al. [Studies on the chemical constituents of Urtica dioica L. grown in Tibet Autonomous Region]. Zhong Yao Cai. 2007;30:662-4 pubmed
    ..Dotriacotane, erucic acid, scopoletin, rutin and p-hydroxylbenzalcohol were obtained from Urtica L. for the first time. Their structures were confirmed by modem spectral analysis (NMR, MS, etc)...
  13. Keller J, Wang J, Kang J, Hanson J, Kamath P, Swain J, et al. Strength: a relevant link to functional performance in the neurodegenerative disease of adrenomyeloneuropathy. Neurorehabil Neural Repair. 2012;26:1080-8 pubmed publisher
    ..Such information could help clinicians develop more effective rehabilitative techniques. ..
  14. Devouge V, Rogniaux H, Nesi N, Tessier D, Guéguen J, Larré C. Differential proteomic analysis of four near-isogenic Brassica napus varieties bred for their erucic acid and glucosinolate contents. J Proteome Res. 2007;6:1342-53 pubmed
    ..Accumulation of cruciferins was found to be only slightly affected, whereas significant quantitative differences were mainly found for proteins involved in defense system and carbohydrate metabolism. ..
  15. Messamore E, Hoffman W, Yao J. Niacin sensitivity and the arachidonic acid pathway in schizophrenia. Schizophr Res. 2010;122:248-56 pubmed publisher
    ..Though AA levels were unrelated to measures of niacin response in schizophrenia, the correlation between adrenic acid and niacin efficacy in schizophrenia suggests relevance of the n-6 PUFA pathway to the blunted niacin response. ..
  16. Liu F, Qiao F, Tong M, Liu L, Fu Z, Dan B, et al. Further evaluation of a novel nano-scale gene vector for in vivo transfection of siRNA. J Cell Biochem. 2011;112:1329-36 pubmed publisher
    ..From all aspects of tumor gene therapy and basic research, LCP is valuable for scientific research and medical applications. ..
  17. Shen Y, Jin X, Zhao Y, Altunbak G, Lin L, Shu P, et al. [The hypolipidemic and liver protective effect of (Z)-N-(2-hydroxyethyl) docos-13-enamide on hyperlipidemic golden hamsters]. Yao Xue Xue Bao. 2012;47:1252-6 pubmed
    ..The exact lipid-lowering mechanism of (Z)-N-(2-hydroxyethyl) docos-13-enamide needs further investigation. ..
  18. Tanaka K, Shimizu T, Ohtsuka Y, Yamashiro Y, Oshida K. Early dietary treatments with Lorenzo's oil and docosahexaenoic acid for neurological development in a case with Zellweger syndrome. Brain Dev. 2007;29:586-9 pubmed
    ..Our findings suggest that the dietary treatment with combination of MCT milk, DHA, Lorenzo's oil, and Lunaria oil in the patients with Zellweger syndrome bring some benefits for neurological development. ..
  19. Benito Leon J, Zamorano T, Martín Peña G, Tapia M, Alvarez Linera J. [Backache as the initial symptom of adrenomyeloneuropathy]. Rev Neurol. 2000;31:1167-70 pubmed
    ..The lumbago associated with adrenomyeloneuropathy is probably due to demyelination of the spinal tracts. Although lumbago is usually a benign condition, a careful history and examination is necessary in all such cases. ..
  20. Wang N, Shi L, Tian F, Ning H, Wu X, Long Y, et al. Assessment of FAE1 polymorphisms in three Brassica species using EcoTILLING and their association with differences in seed erucic acid contents. BMC Plant Biol. 2010;10:137 pubmed publisher
    ..The association between B. napus FAE1 polymorphisms and the erucic acid contents of seeds may provide useful guidance for LEA breeding. The discovery of the LEA resource in B. rapa can be exploited in Brasscia cultivation. ..
  21. Thomas E, Yao J. Clozapine specifically alters the arachidonic acid pathway in mice lacking apolipoprotein D. Schizophr Res. 2007;89:147-53 pubmed
    ..We further report increases in LA, eicosadienoic acid and docosahexaenoic acid in apoD knock-out compared to wild-type mice. These findings implicate an important apoD/AA interaction, which may be necessary for clozapine function. ..
  22. Walters D, Raynor L, Mitchell A, Walker R, Walker K. Antifungal activities of four fatty acids against plant pathogenic fungi. Mycopathologia. 2004;157:87-90 pubmed
    ..The antifungal activities exhibited by linolenic, linoleic and oleic acids may be useful in the search for alternative approaches to controlling important plant pathogens, such as those examined in this study. ..
  23. De Felice C, Signorini C, Durand T, Oger C, Guy A, Bultel Poncé V, et al. F2-dihomo-isoprostanes as potential early biomarkers of lipid oxidative damage in Rett syndrome. J Lipid Res. 2011;52:2287-97 pubmed publisher
  24. VanRollins M, Woltjer R, Yin H, Morrow J, Montine T. F2-dihomo-isoprostanes arise from free radical attack on adrenic acid. J Lipid Res. 2008;49:995-1005 pubmed publisher
    ..We propose that F2-dihomo-IsoPs may serve as quantitative in vivo biomarkers of free radical damage to myelin from primate white matter. ..
  25. Ferri R, Chance P. Lorenzo's oil: advances in the treatment of neurometabolic disorders. Arch Neurol. 2005;62:1045-6 pubmed
  26. Plat J, Mensink R. Effects of diets enriched with two different plant stanol ester mixtures on plasma ubiquinol-10 and fat-soluble antioxidant concentrations. Metabolism. 2001;50:520-9 pubmed
    ..However, for the most lipophylic carotenoids, some of the reduction was also related to the decrease in cholesterol absorption. ..
  27. Liu X, Tu J, Chen B, Fu T. Identification of the linkage relationship between the flower colour and the content of erucic acid in the resynthesized Brassica napus L. Yi Chuan Xue Bao. 2004;31:357-62 pubmed
    ..napus L. The genetic distance of the genes for yellow flower and the low erucic acid content was 2.2 cM and 5.4 cM from the marker S92(-1400), respectively. ..
  28. Okita M, Sasagawa T, Ohta Y, Kaneyuki T, Suzuki K. Effect of arachidonic acid-rich oil on lipids and arachidonate metabolites in ethanol- treated rats. Prostaglandins Leukot Essent Fatty Acids. 2001;64:273-9 pubmed
    ..These observations suggest that AAoil supplementation reduces liver injury of ethanol-treated rats, although longer observation will be necessary for confirmation. ..
  29. Li X, van Loo E, Gruber J, Fan J, Guan R, Frentzen M, et al. Development of ultra-high erucic acid oil in the industrial oil crop Crambe abyssinica. Plant Biotechnol J. 2012;10:862-70 pubmed publisher
  30. Gupta V, Mukhopadhyay A, Arumugam N, Sodhi Y, Pental D, Pradhan A. Molecular tagging of erucic acid trait in oilseed mustard (Brassica juncea) by QTL mapping and single nucleotide polymorphisms in FAE1 gene. Theor Appl Genet. 2004;108:743-9 pubmed
    ..juncea belonging to two distinct gene pools (Indian and east European) and other oil-yielding Brassica species. ..
  31. Xu J, Francis T, Mietkiewska E, Giblin E, Barton D, Zhang Y, et al. Cloning and characterization of an acyl-CoA-dependent diacylglycerol acyltransferase 1 (DGAT1) gene from Tropaeolum majus, and a study of the functional motifs of the DGAT protein using site-directed mutagenesis to modify enzyme activity and oil cont. Plant Biotechnol J. 2008;6:799-818 pubmed publisher
    ..Thus, alteration of this putative serine/threonine protein kinase site can be exploited to enhance DGAT1 activity, and expression of mutated DGAT1 can be used to enhance oil content...
  32. Stempfle F, Ortmann P, Mecking S. Which polyesters can mimic polyethylene?. Macromol Rapid Commun. 2013;34:47-50 pubmed publisher
    ..Available data suggest that to mimic linear polyethylenes thermal properties, even longer sequences, amounting to at least four times a fatty acid chain, fully incorporated in a linear fashion are required. ..
  33. Mysore D, Viraraghavan T, Jin Y. Treatment of oily waters using vermiculite. Water Res. 2005;39:2643-53 pubmed
    ..Expanded vermiculite showed better retention than hydrophobic vermiculite. The results showed that the expanded vermiculite had a greater affinity for oil than hydrophobized vermiculite. ..
  34. Veenman L, Alten J, Linnemannstöns K, Shandalov Y, Zeno S, Lakomek M, et al. Potential involvement of F0F1-ATP(synth)ase and reactive oxygen species in apoptosis induction by the antineoplastic agent erucylphosphohomocholine in glioblastoma cell lines : a mechanism for induction of apoptosis via the 18 kDa mitochondrial trans. Apoptosis. 2010;15:753-68 pubmed publisher
    ..Consequently, our findings strongly point to a role for the F(O) subunit of the mitochondrial F(O)F(1)-ATP(synth)ase in ErPC3-induced apoptosis and dissipation of Deltapsi(m) as well as ROS generation by ErPC3 and TSPO. ..
  35. Liu J, Liang S, Liu X, Brown J, Newman K, Sunkara M, et al. The absence of ABCD2 sensitizes mice to disruptions in lipid metabolism by dietary erucic acid. J Lipid Res. 2012;53:1071-9 pubmed publisher
  36. Arai Y, Kitamura Y, Hayashi M, Oshida K, Shimizu T, Yamashiro Y. Effect of dietary Lorenzo's oil and docosahexaenoic acid treatment for Zellweger syndrome. Congenit Anom (Kyoto). 2008;48:180-2 pubmed publisher
    ..DHA levels in the brains and livers of treated patients were higher than in untreated patients. Early initiation of Lorenzo's oil and the long-term administration of DHA may be useful for patients with Zellweger syndrome. ..
  37. Qin Q, Ma P, Kuang X, Gao M, Mo D, Xia S, et al. Novel function of N,N-bis(2-chloroethyl)docos-13-enamide for reversal of multidrug resistance in tongue cancer. Eur J Pharmacol. 2013;721:208-14 pubmed publisher
    ..Taken together, our data suggested that compound J was an excellent candidate for reversing MDR in cancer therapy. ..
  38. Siva N. Positive effects with Lorenzo's oil. Lancet Neurol. 2005;4:529 pubmed
  39. Min K, Benzer S. Preventing neurodegeneration in the Drosophila mutant bubblegum. Science. 1999;284:1985-8 pubmed
    ..Mutant flies thus provide a potential model system for studying mechanisms of neurodegenerative disease and screening drugs for treatment. ..
  40. Greiner R, Catalan J, Moriguchi T, Salem N. Docosapentaenoic acid does not completely replace DHA in n-3 FA-deficient rats during early development. Lipids. 2003;38:431-5 pubmed
    ..The lack of total 22-carbon (22C) FA in the brain during the rapid membrane biogenesis that occurs during early development could be a factor in the nervous system functional deficits associated with n-3 FA deficiency. ..
  41. Lüke M, Januschowski K, Lüke J, Grisanti S, Szurman P, Dietz K, et al. The safety profile of alkylphosphocholines in the model of the isolated perfused vertebrate retina. Graefes Arch Clin Exp Ophthalmol. 2010;248:511-8 pubmed publisher
    ..Thus, APCs should further be considered as promising candidates for future clinical applications in ophthalmology. ..
  42. Siriwatwechakul W, Lafleur T, Prud homme R, Sullivan P. Effects of organic solvents on the scission energy of rodlike micelles. Langmuir. 2004;20:8970-4 pubmed
  43. Padding J, Boek E, Briels W. Dynamics and rheology of wormlike micelles emerging from particulate computer simulations. J Chem Phys. 2008;129:074903 pubmed publisher
    ..At high shear rates we observe a steady-state shear stress proportional to gamma(1/3), where gamma is the shear rate. This is confirmed by our high shear rate experiments of real EHAC in a parallel-plate geometry. ..
  44. Moser H, Raymond G, Dubey P. Adrenoleukodystrophy: new approaches to a neurodegenerative disease. JAMA. 2005;294:3131-4 pubmed
    ..Neonatal screening is likely to become available, and a wider awareness of X-ALD and its various modes of presentation permit new proactive approaches to this distressing disorder. ..
  45. Mietkiewska E, Giblin E, Wang S, Barton D, Dirpaul J, Brost J, et al. Seed-specific heterologous expression of a nasturtium FAE gene in Arabidopsis results in a dramatic increase in the proportion of erucic acid. Plant Physiol. 2004;136:2665-75 pubmed
    ..Given its strong and unique preference for elongating 20:1-CoA, the utility of the FAE gene product for directing or engineering increased synthesis of erucic acid is discussed...
  46. Awasthi N, Singh R. Lipase-catalyzed synthesis of fatty acid amide (erucamide) using fatty acid and urea. J Oleo Sci. 2007;56:507-9 pubmed
    ..This process for synthesis is economical as we used urea in place of ammonia or other amidation reactant at atmospheric pressure. The amount of catalyst used is 3 %. ..
  47. Jadhav A, Katavic V, Marillia E, Michael Giblin E, Barton D, Kumar A, et al. Increased levels of erucic acid in Brassica carinata by co-suppression and antisense repression of the endogenous FAD2 gene. Metab Eng. 2005;7:215-20 pubmed
    ..The possibility of using these approaches to produce prototype transgenic germplasm of the Brassicaceae accumulating seed oils with improved proportions of erucic and other VLCFAs is discussed. ..
  48. Garrido López A, Esquiu V, Tena M. Determination of oleamide and erucamide in polyethylene films by pressurised fluid extraction and gas chromatography. J Chromatogr A. 2006;1124:51-6 pubmed
    ..Finally, the method was applied to determine oleamide and erucamide in several polyethylene films and the results were statistically equal to those obtained by pyrolysis and gas-phase chemiluminescence (CL). ..
  49. Sengupta A, Ghosh M. Hypolipidemic effect of mustard oil enriched with medium chain fatty acid and polyunsaturated fatty acid. Nutrition. 2011;27:1183-93 pubmed publisher
    ..Mustard oil can be enriched with MCFA and n-3 PUFA and these modified lipids exhibited hypocholesterolemic and hypolipidemic effects in rats when compared to unmodified mustard oil. ..
  50. Joffrain C, Millot S, Boucrot P, Escousse A, Rocquelin G. [Variations in the lipid and fatty acid composition of cardiac tissue during perfusion of hearts isolated from rats on a high colza oil diet]. C R Acad Sci Hebd Seances Acad Sci D. 1975;280:2489-92 pubmed
    ..In contrast with this finding, lipids and phospholipids of hearts from Rat feed with peanut oil is not decreased and fatty acid composition slightly altered. ..
  51. Tsujii T, Kinoshita M, Tomimoto H, Hitomi T, Okazaki T, Uchiyama T, et al. [A case of adolescent adrenoleukodystrophy with clinical improvement after allogeneic bone marrow transplantation (allo-BMT)]. Rinsho Shinkeigaku. 2004;44:667-72 pubmed
    ..We also observed improvement of abnormal findings on brain MRI and magnetic stimulation. We believed that allo-BMT is effective for the treatment of adolescent type adrenoleukodystrophy. ..
  52. Sumich A, Matsudaira T, Heasman B, Gow R, Ibrahimovic A, Ghebremeskel K, et al. Fatty acid correlates of temperament in adolescent boys with attention deficit hyperactivity disorder. Prostaglandins Leukot Essent Fatty Acids. 2013;88:431-6 pubmed publisher
    ..Results are in line with a role of fatty acids in brain function. They suggest that those fatty acids that are involved in myelination (Adrenic, Oleic) have the strongest associations with temperament in adolescents with ADHD. ..
  53. Staritsyn S, Mamashin V, Zakharychev V, Iaminskiĭ I, Dubrovin E, Lomonosov A, et al. [Mixed monolayers of amphiphile-modified nucleic bases and diynoic acids. I. Phase states at air-water interface and in Langmuir-Blodgett films]. Biofizika. 2004;49:635-45 pubmed
    ..A study of the films transferred to the solid substrate by atomic force microscopy indicated that this concentration dependence of miscibility behavior was conserved in the transferred films. ..