linoleic acids


Summary: Eighteen-carbon essential fatty acids that contain two double bonds.

Top Publications

  1. Mani S, Reyna A, Alejandro M, Crowley J, Markaverich B. Disruption of male sexual behavior in rats by tetrahydrofurandiols (THF-diols). Steroids. 2005;70:750-4 pubmed
    ..These findings suggest that the THF-diols modulate hypothalamo-pituitary axis to regulate steroid hormone-dependent male sexual behavior. ..
  2. Mabalirajan U, Aich J, Leishangthem G, Sharma S, Dinda A, Ghosh B. Effects of vitamin E on mitochondrial dysfunction and asthma features in an experimental allergic murine model. J Appl Physiol (1985). 2009;107:1285-92 pubmed publisher
    ..In summary, these findings show that Vit-E reduces key mitochondrial dysfunctions and alleviates asthmatic features. ..
  3. Xia Q, Yin J, Fu P, Boudreau M. Photo-irradiation of Aloe vera by UVA--formation of free radicals, singlet oxygen, superoxide, and induction of lipid peroxidation. Toxicol Lett. 2007;168:165-75 pubmed
    ..These results suggest that humans exposed to products that contain Aloe vera whole leaf extracts may have enhanced sensitivity to ultraviolet light. ..
  4. Gerhardt B, Fischer K, Balkenhohl T, Pohnert G, Kuhn H, Wasternack C, et al. Lipoxygenase-mediated metabolism of storage lipids in germinating sunflower cotyledons and beta-oxidation of (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid by the cotyledonary glyoxysomes. Planta. 2005;220:919-30 pubmed
    ..The results suggest that the hydroxyl/oxo group at C-13 of lipoxygenase-derived fatty acids forms a barrier to continuous beta-oxidation by glyoxysomes...
  5. Coutant F, Agaugué S, Perrin Cocon L, Andre P, Lotteau V. Sensing environmental lipids by dendritic cell modulates its function. J Immunol. 2004;172:54-60 pubmed
    ..The therapeutic emulsion intralipid also blocks LPC action on PPAR activity and DC maturation. Intralipid may thus be an alternative therapeutic strategy for some chronic inflammatory diseases. ..
  6. Soonsanga S, Lee J, Helmann J. Oxidant-dependent switching between reversible and sacrificial oxidation pathways for Bacillus subtilis OhrR. Mol Microbiol. 2008;68:978-86 pubmed publisher
    ..Thus, depending on the oxidant, OhrR can be either reversibly oxidized or can instead function as a sacrificial regulator...
  7. König B, Eder K. Differential action of 13-HPODE on PPARalpha downstream genes in rat Fao and human HepG2 hepatoma cell lines. J Nutr Biochem. 2006;17:410-8 pubmed
    ..Consequently, cellular and secreted triglyceride levels were not changed after incubation of HepG2 cells with 13-HPODE. In conclusion, this study shows that 13-HPODE activates PPARalpha in rat Fao but not in human HepG2 hepatoma cells. ..
  8. Altmann R, Hausmann M, Spottl T, Gruber M, Bull A, Menzel K, et al. 13-Oxo-ODE is an endogenous ligand for PPARgamma in human colonic epithelial cells. Biochem Pharmacol. 2007;74:612-22 pubmed
    ..High amounts of 13-Oxo-ODE can be induced in CECs by stimulation of linoleic acid metabolism. 13-Oxo-ODE binds to PPARgamma and has anti-inflammatory effects. 13-HODE dehydrogenase might be a therapeutic target in IBD. ..
  9. Miyamoto S, Martinez G, Rettori D, Augusto O, Medeiros M, Di Mascio P. Linoleic acid hydroperoxide reacts with hypochlorous acid, generating peroxyl radical intermediates and singlet molecular oxygen. Proc Natl Acad Sci U S A. 2006;103:293-8 pubmed
    ..In addition, the detection of 18O2 (1Deltag) and peroxyl radicals strongly supports the involvement of a Russell mechanism in the generation of O2 (1Deltag). ..

More Information


  1. Liu W, Yin H, Akazawa Y, Yoshida Y, Niki E, Porter N. Ex vivo oxidation in tissue and plasma assays of hydroxyoctadecadienoates: Z,E/E,E stereoisomer ratios. Chem Res Toxicol. 2010;23:986-95 pubmed publisher
    ..Modified protocols for HODE analyses (tissue and plasma methods #2) are described that should be used for assays of tissues and fluids...
  2. Zhang Y, Xue R, Zhang Z, Yang X, Shi H. Palmitic and linoleic acids induce ER stress and apoptosis in hepatoma cells. Lipids Health Dis. 2012;11:1 pubmed publisher
    ..These results confirm that ER stress contributes to fatty acid-induced liver cell apoptosis. ..
  3. Dauchy R, Dauchy E, Davidson L, Krause J, Lynch D, Tirrell P, et al. Inhibition of fatty acid transport and proliferative activity in tissue-isolated human squamous cell cancer xenografts perfused in situ with melatonin or eicosapentaenoic or conjugated linoleic acids. Comp Med. 2007;57:377-82 pubmed
    Melatonin and eicosapentaenoic and 10t,12c-conjugated linoleic acids suppress the growth-stimulating effects of linoleic acid (LA) and its metabolism to the mitogenic agent 13-(S)-hydroxyoctadecadienoic acid (13-(S)-HODE) in established ..
  4. Wittwer J, Hersberger M. The two faces of the 15-lipoxygenase in atherosclerosis. Prostaglandins Leukot Essent Fatty Acids. 2007;77:67-77 pubmed
    ..This will now allow large studies to investigate an association of 15-LOX with coronary artery disease and to answer the question whether 15-LOX is pro- or anti-atherogenic in humans. ..
  5. Rabetafika H, Gigot C, Fauconnier M, Ongena M, Destain J, du Jardin P, et al. Sugar beet leaves as new source of hydroperoxide lyase in a bioprocess producing green-note aldehydes. Biotechnol Lett. 2008;30:1115-9 pubmed publisher
    ..The stability of cis-3-hexenal was improved by acidifying the reaction medium. Based on these studies, a bioprocess producing green-note aldehydes in a laboratory-scale was achieved. ..
  6. Herreno Saenz D, Xia Q, Chiu L, Fu P. UVA photoirradiation of halogenated-polycyclic aromatic hydrocarbons leading to induction of lipid peroxidation. Int J Environ Res Public Health. 2006;3:191-5 pubmed
    ..The results indicate that upon photoirradiation by UVA all these compounds induced lipid peroxidation at different levels. These results suggest that halo-PAHs may be harmful to human health. ..
  7. Xia Q, Yin J, Cherng S, Wamer W, Boudreau M, Howard P, et al. UVA photoirradiation of retinyl palmitate--formation of singlet oxygen and superoxide, and their role in induction of lipid peroxidation. Toxicol Lett. 2006;163:30-43 pubmed
    ..ESR studies on the photoirradiation of 5,6-epoxy-RP and AR indicate that these compounds exhibit similar photosensitizing activities as RP under UVA light. ..
  8. Wang R, Kern J, Goodfriend T, Ball D, Luesch H. Activation of the antioxidant response element by specific oxidized metabolites of linoleic acid. Prostaglandins Leukot Essent Fatty Acids. 2009;81:53-9 pubmed publisher
    ..EKODE requires transcription factor NRF2 and PI3-kinase for ARE activity. The results suggest that specific oxidation products of linoleic acid may initiate responses that lessen damage caused by oxidative stress. ..
  9. Moghaddam M, Motoba K, Borhan B, Pinot F, Hammock B. Novel metabolic pathways for linoleic and arachidonic acid metabolism. Biochim Biophys Acta. 1996;1290:327-39 pubmed
    ..This manuscript is the first report of techniques for the separation and identification of regio and geometrical isomer of an interesting class of oxylipins and their metabolism by liver microsomes and S-9 fractions to THF-diols. ..
  10. Chouinard P, Corneau L, Saebø A, Bauman D. Milk yield and composition during abomasal infusion of conjugated linoleic acids in dairy cows. J Dairy Sci. 1999;82:2737-45 pubmed
    Conjugated linoleic acids refer to a mixture of positional and geometric isomers of linoleic acid with conjugated double bounds...
  11. Fischer B, von Knethen A, Brüne B. Dualism of oxidized lipoproteins in provoking and attenuating the oxidative burst in macrophages: role of peroxisome proliferator-activated receptor-gamma. J Immunol. 2002;168:2828-34 pubmed
    ..Desensitization of macrophages may have important consequences for the behavior of macrophages/foam cells in atherosclerotic lesions. ..
  12. Schild R, Schaiff W, Carlson M, Cronbach E, Nelson D, Sadovsky Y. The activity of PPAR gamma in primary human trophoblasts is enhanced by oxidized lipids. J Clin Endocrinol Metab. 2002;87:1105-10 pubmed
    ..We concluded that 9-HODE, 13-HODE, and 15-HETE activate PPAR gamma in primary human trophoblasts. These PPAR gamma ligands may play a role in placental differentiation, yet they are unlikely to contribute to trophoblast dysfunction. ..
  13. Cho H, Gallaher D, Csallany A. Nonradiometric HPLC measurement of 13(S)-hydroxyoctadecadienoic acid from rat tissues. Anal Biochem. 2003;318:47-51 pubmed
    ..With the currently described method, good separation from unreacted interfering compounds and quantification for 13(S)-HODE were achieved within 35 min with a minimum detection limit of 0.5 ng per injection. ..
  14. Frank C, Storey K. The optimal depot fat composition for hibernation by golden-mantled ground squirrels (Spermophilus lateralis). J Comp Physiol B. 1995;164:536-42 pubmed
    ..The results indicate that there is an optimal level of dietary linoleic acid for proper hibernation, and this is equal to that of the natural diet.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  15. Weichert H, Kolbe A, Kraus A, Wasternack C, Feussner I. Metabolic profiling of oxylipins in germinating cucumber seedlings--lipoxygenase-dependent degradation of triacylglycerols and biosynthesis of volatile aldehydes. Planta. 2002;215:612-9 pubmed
    ..The first evidence is presented for an involvement of a lipid-body LOX form in the production of volatile aldehydes. ..
  16. Willker W, Leibfritz D. Lipid oxidation in blood plasma of patients with neurological disorders. Brain Res Bull. 2000;53:437-43 pubmed
    ..Its concentration is about 60 microM. In two-dimensional H,H total correlation spectroscopy spectra also a very low amount (6-7 microM) of 13-HODE can be detected. ..
  17. Rong R, Ramachandran S, Penumetcha M, Khan N, Parthasarathy S. Dietary oxidized fatty acids may enhance intestinal apolipoprotein A-I production. J Lipid Res. 2002;43:557-64 pubmed
    ..mRNA and PPAR-gamma ligand could increase apoA-I secretion in these cells. Therefore we propose that the mechanism for the induction of apoA-I might include PPAR-gamma for which oxidized fatty acid is a ligand. ..
  18. Nagy L, Tontonoz P, Alvarez J, Chen H, Evans R. Oxidized LDL regulates macrophage gene expression through ligand activation of PPARgamma. Cell. 1998;93:229-40 pubmed
    ..These results suggest that PPARgamma may be a key regulator of foam cell gene expression. ..
  19. Bell J, Kennelly J. Short communication: Postruminal infusion of conjugated linoleic acids negatively impacts milk synthesis in Holstein cows. J Dairy Sci. 2003;86:1321-4 pubmed
  20. Shureiqi I, Jiang W, Zuo X, Wu Y, Stimmel J, Leesnitzer L, et al. The 15-lipoxygenase-1 product 13-S-hydroxyoctadecadienoic acid down-regulates PPAR-delta to induce apoptosis in colorectal cancer cells. Proc Natl Acad Sci U S A. 2003;100:9968-73 pubmed
    ..Our findings indicate that the down-regulation of PPAR-delta by 15-LOX-1 through 13-S-HODE is an apoptotic signaling pathway that is activated by NSAIDs. ..
  21. Howe G, Lee G, Itoh A, Li L, DeRocher A. Cytochrome P450-dependent metabolism of oxylipins in tomato. Cloning and expression of allene oxide synthase and fatty acid hydroperoxide lyase. Plant Physiol. 2000;123:711-24 pubmed
    ..These results demonstrate that tomato uses genetically distinct signaling pathways for the regulation of different classes of wound responsive genes. ..
  22. Hatley M, Srinivasan S, Reilly K, Bolick D, Hedrick C. Increased production of 12/15 lipoxygenase eicosanoids accelerates monocyte/endothelial interactions in diabetic db/db mice. J Biol Chem. 2003;278:25369-75 pubmed
    ..Modulation of the 12/15LO pathway in the vessel wall may provide therapeutic benefit for early vascular inflammatory events in diabetes. ..
  23. Hamberg M. An epoxy alcohol synthase pathway in higher plants: biosynthesis of antifungal trihydroxy oxylipins in leaves of potato. Lipids. 1999;34:1131-42 pubmed
  24. Nakazawa R, Shima M, Adachi S. Effect of oil-droplet size on the oxidation of microencapsulated methyl linoleate. J Oleo Sci. 2008;57:225-32 pubmed
    ..The value of the energy suggested that the oxidation itself was a rate-limiting step for the oxidation of methyl linoleate encapsulated with maltodextrin. ..
  25. Cataldo F. Interaction of C(60) fullerene with lipids. Chem Phys Lipids. 2010;163:524-9 pubmed publisher
    ..The kinetics of C(60) oxidation in lipids was determined spectrophotometrically both at room temperature in the dark and under UV irradiation. The oxidized products derived from C(60) photo-oxidation in lipids have been identified. ..
  26. Saito F, Iwamoto S, Yamauchi R. Reaction products of gamma-tocopherol with (E)-4-oxo-2-nonenal in acidic acetonitrile. Biosci Biotechnol Biochem. 2010;74:168-74 pubmed
    ..The results indicate that gamma-tocopherol may trap ONE under acidic conditions of lipid peroxidation. ..
  27. Białek A, Stawarska A, Bodecka J, Białek M, Tokarz A. Pomegranate seed oil influences the fatty acids profile and reduces the activity of desaturases in livers of Sprague-Dawley rats. Prostaglandins Other Lipid Mediat. 2017;131:9-16 pubmed publisher
    ..of diet supplementation with pomegranate seed oil - as conjugated linolenic acids (CLnA) source, or conjugated linoleic acids (CLA) and to examine the mechanism of their activity...
  28. Murakami A, Nagao K, Juni N, Hara Y, Umeda M. An N-terminal di-proline motif is essential for fatty acid-dependent degradation of ?9-desaturase in Drosophila. J Biol Chem. 2017;292:19976-19986 pubmed publisher
    ..of membrane phospholipids were increased by supplementation with unsaturated fatty acids, such as oleic and linoleic acids. In contrast, inhibition of DESAT1 activity remarkably suppressed its degradation...
  29. Umeno A, Shichiri M, Ishida N, Hashimoto Y, Abe K, Kataoka M, et al. Singlet oxygen induced products of linoleates, 10- and 12-(Z,E)-hydroxyoctadecadienoic acids (HODE), can be potential biomarkers for early detection of type 2 diabetes. PLoS ONE. 2013;8:e63542 pubmed publisher
    ..In conclusion, 10- and 12-(Z,E)-HODE may be prominent biomarkers for the early detection of IGT and "high-normal" type without OGTT. ..
  30. GEDDES R, Hayashi K, Bongers Q, Wehber M, Anderson I, Jansen A, et al. Conjugated Linoleic Acid Administration Induces Amnesia in Male Sprague Dawley Rats and Exacerbates Recovery from Functional Deficits Induced by a Controlled Cortical Impact Injury. PLoS ONE. 2017;12:e0169494 pubmed publisher
    Long-chain polyunsaturated fatty acids like conjugated linoleic acids (CLA) are required for normal neural development and cognitive function and have been ascribed various beneficial functions...
  31. Saeed S, Gillies D, Wagner G, Howell N. ESR and NMR spectroscopy studies on protein oxidation and formation of dityrosine in emulsions containing oxidised methyl linoleate. Food Chem Toxicol. 2006;44:1385-92 pubmed
    ..Monitoring tyrosyl radicals and formation of dityrosine is of practical value in order to enhance the acceptability, nutritional and safety aspects of proteins. ..
  32. Biswas A, Sharma B, Willett J, Advaryu A, Erhan S, Cheng H. Azide derivatives of soybean oil and fatty esters. J Agric Food Chem. 2008;56:5611-6 pubmed publisher
    ..This reaction has been applied to methyl oleate, methyl linoleate, soybean oil, and methyl soyate. The resulting structures have been studied by NMR. ..
  33. García Escobar E, Monastero R, García Serrano S, Gómez Zumaquero J, Lago Sampedro A, Rubio Martín E, et al. Dietary fatty acids modulate adipocyte TNFa production via regulation of its DNA promoter methylation levels. J Nutr Biochem. 2017;47:106-112 pubmed publisher
    ..In addition, 3 T3-L1 cells were treated with palmitic, oleic and linoleic acids, with and without 5-Azacitydine (5-AZA)...
  34. Geppert J, Demmelmair H, Hornstra G, Koletzko B. Co-supplementation of healthy women with fish oil and evening primrose oil increases plasma docosahexaenoic acid, gamma-linolenic acid and dihomo-gamma-linolenic acid levels without reducing arachidonic acid concentrations. Br J Nutr. 2008;99:360-9 pubmed
    ..It increases plasma GLA, DGLA, and DHA levels without impairing ARA status. These data provide a basis for testing this FSO/EPO blend in pregnant women for its effects on maternal and neonatal FA status and infant development. ..
  35. Kojima K, Keta S, Uesaka K, Kato A, Takatani N, Ihara K, et al. A simple method for isolation and construction of markerless cyanobacterial mutants defective in acyl-acyl carrier protein synthetase. Appl Microbiol Biotechnol. 2016;100:10107-10113 pubmed
    ..In this study, the wild-type Synechocystis cells were shown to be sensitive to lauric, oleic, and linoleic acids as well, and the resistance to these fatty acids was shown to be enhanced by inactivation of the aas gene...
  36. Cerolini S, Surai P, Speake B, Sparks N. Dietary fish and evening primrose oil with vitamin E effects on semen variables in cockerels. Br Poult Sci. 2005;46:214-22 pubmed
    ..The proportion of motile spermatozoa was improved by the increased supplementation of vitamin E in all oil treatments. ..
  37. Vickers T, Wyllie S, Fairlamb A. Leishmania major elongation factor 1B complex has trypanothione S-transferase and peroxidase activity. J Biol Chem. 2004;279:49003-9 pubmed
    ..These results suggest that, in addition to its role in protein synthesis, the Leishmania eEF1B may help protect the parasite from lipid peroxidation. ..
  38. Markaverich B, Alejandro M, Thompson T, Mani S, Reyna A, Portillo W, et al. Tetrahydrofurandiols (THF-diols), leukotoxindiols (LTX-diols), and endocrine disruption in rats. Environ Health Perspect. 2007;115:702-8 pubmed
    ..THF-diols, LTX-diols, and/or their metabolites likely act additively to disrupt endocrine function in male and female rats at concentrations (0.5-1 ppm) that are 200-fold lower than those of classical phytoestrogen endocrine disruptors. ..
  39. Fang C, Chen J, Liu S. [Studies on the chemical constituents of rhizoma of Coniogramme japonica]. Zhong Yao Cai. 2010;33:557-9 pubmed
    ..All compounds are isolated from the genus for the first time, and the compound 1 is a new compound. ..
  40. Schlecker T, Schmidt A, Dirdjaja N, Voncken F, Clayton C, Krauth Siegel R. Substrate specificity, localization, and essential role of the glutathione peroxidase-type tryparedoxin peroxidases in Trypanosoma brucei. J Biol Chem. 2005;280:14385-94 pubmed
    ..Thus, the cellular functions of the glutathione peroxidase-type enzymes cannot be taken over by the 2 Cys-peroxiredoxins that also occur in the cytosol and mitochondrion of the parasite. ..
  41. Farrell E, Chen Y, Barazanji M, Jeffries K, Cameroamortegui F, Merkler D. Primary fatty acid amide metabolism: conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells. J Lipid Res. 2012;53:247-56 pubmed publisher
    ..Furthermore, the data support a role for the N-acylethanolamines as precursors for the PFAMs and provide valuable new kinetic results useful in modeling the metabolic flux through the pathways for PFAM biosynthesis and degradation...
  42. Priatni S, Hartati S, Dewi P, Kardono L, Singgih M, Gusdinar T. Fatty acid methyl ester from Neurospora intermedia N-1 isolated from Indonesian red peanut cake (oncom merah). Pak J Biol Sci. 2010;13:731-7 pubmed
    ..We suggested that the structure of the pure compound 1 is methyl octadeca-8,12-dienoate. The presence methyl octadeca-8,12-dienoate in N. intermedia is the first report. ..
  43. Cimen I, Astarci E, Banerjee S. 15-lipoxygenase-1 exerts its tumor suppressive role by inhibiting nuclear factor-kappa B via activation of PPAR gamma. J Cell Biochem. 2011;112:2490-501 pubmed publisher
    ..Our data show that the inhibition of both early and late stages of NF-?B activation could rescued by the PPAR? antagonist GW9662 indicating that the inhibition was most likely mediated via PPAR?. ..
  44. Mazari A, Iwamoto S, Yamauchi R. Effects of linoleic acid position in phosphatidylcholines and cholesterol addition on their rates of peroxidation in unilamellar liposomes. Biosci Biotechnol Biochem. 2010;74:1013-7 pubmed
    ..Our results indicate that the sn-position of unsaturated acyl chains and the cholesterol content are important modulating factors in the oxidizability of membrane phospholipids. ..
  45. Leray V, Dumon H, Martin L, Siliart B, Sergheraert R, Biourge V, et al. No effect of conjugated linoleic acid or Garcinia cambogia on fat-free mass, and energy expenditure in normal cats. J Nutr. 2006;136:1982S-1984S pubmed
  46. Tesoriere L, Allegra M, Gentile C, Livrea M. Betacyanins as phenol antioxidants. Chemistry and mechanistic aspects of the lipoperoxyl radical-scavenging activity in solution and liposomes. Free Radic Res. 2009;43:706-17 pubmed publisher
    ..Either betanin or betanidin incorporated in liposomes with alpha-tocopherol had additive effects, supporting partition of the pigments in the bilayer and lipoperoxyl radical reduction. ..
  47. Tavakoli Yaraki M, Karami Tehrani F, Salimi V, Sirati Sabet M. Induction of apoptosis by Trichostatin A in human breast cancer cell lines: involvement of 15-Lox-1. Tumour Biol. 2013;34:241-9 pubmed publisher
    ..Our findings underline the possible role of 15-Lox-1/13(S)-HODE pathway as a promising molecular approach for the induction of apoptosis in breast cancer cells. ..
  48. Zajdel A, Wilczok A, Węglarz L, Dzierzewicz Z. Phytic acid inhibits lipid peroxidation in vitro. Biomed Res Int. 2013;2013:147307 pubmed publisher
    ..It is concluded that PA inhibits linoleic acid oxidation and reduces the formation of 4-hydroxyalkenals. Acting as an antioxidant it may help to prevent intestinal diseases induced by oxygen radicals and lipid peroxidation products. ..
  49. Hou C. Effect of environmental factors on the production of oxygenated unsaturated fatty acids from linoleic acids by Bacillus megaterium ALA2. Appl Microbiol Biotechnol. 2005;69:463-8 pubmed
    ..5. Time course studies showed 40-48 h is the optimum for the production of both THOAs. These data provide the basis for engineering scale-up production of these new products. ..
  50. Bamford J, Ray S, Musekiwa A, van Gool C, Humphreys R, Ernst E. Oral evening primrose oil and borage oil for eczema. Cochrane Database Syst Rev. 2013;:CD004416 pubmed publisher
    ..This review does not provide information about long-term use of these products. ..
  51. Villacorta L, Zhang J, Garcia Barrio M, Chen X, Freeman B, Chen Y, et al. Nitro-linoleic acid inhibits vascular smooth muscle cell proliferation via the Keap1/Nrf2 signaling pathway. Am J Physiol Heart Circ Physiol. 2007;293:H770-6 pubmed
    ..These studies provide the first evidence that nitroalkene LNO(2) inhibits VSMC proliferation through activation of the Keap1/Nrf2 signaling pathway, suggesting an important role of nitroalkenes in vascular biology. ..
  52. Christy A. Thermally induced isomerization of trilinolein and trilinoelaidin at 250 degrees C: analysis of products by gas chromatography and infrared spectroscopy. Lipids. 2009;44:1105-12 pubmed publisher
    ..In addition, these two fatty acids also isomerize into conjugated linoleic acids (CLAs). The profiles of the CLAs are identical in both cases.
  53. Tooker J, De Moraes C. A gall-inducing caterpillar species increases essential fatty acid content of its host plant without concomitant increases in phytohormone levels. Mol Plant Microbe Interact. 2009;22:551-9 pubmed publisher
    ..We found, unexpectedly, that G. gallaesolidaginis strongly increased amounts of linolenic and linoleic acids inside galls without associated increases in two downstream products, 12-oxo-phytodienoic or jasmonic acid...