232
Views
8
CrossRef citations to date
0
Altmetric
Article

Comparing the In Vitro Antitumor, Antioxidant and Anti-Inflammatory Activities between Two New Very Long Chain Polyunsaturated Fatty Acids, Docosadienoic Acid (DDA) and Docosatrienoic Acid (DTA), and Docosahexaenoic Acid (DHA)

, &
Pages 1697-1707 | Received 09 Mar 2020, Accepted 24 Jul 2020, Published online: 11 Aug 2020

References

  • Fabian CJ, Kimler BF, Hursting SD. Omega-3 fatty acids for breast cancer prevention and survivorship. Breast Cancer Res. 2015;17:62. doi:10.1186/s13058-015-0571-6
  • Serini S, Ottes Vasconcelos R, Fasano E, Calviello G. How plausible is the use of dietary n-3 PUFA in the adjuvant therapy of cancer?. Nutr Res Rev. 2016;29(1):102–25. doi:10.1017/S0954422416000044
  • Song C, Shieh C-H, Wu Y-S, Kalueff A, Gaikwad S, Su K-P. The role of omega-3 polyunsaturated fatty acids eicosapentaenoic and docosahexaenoic acids in the treatment of major depression and Alzheimer's disease: Acting separately or synergistically?. Prog Lipid Res. 2016;62:41–54. doi:10.1016/j.plipres.2015.12.003
  • Elagizi A, Lavie CJ, Marshall K, DiNicolantonio JJ, O'Keefe JH, Milani RV. Omega-3 polyunsaturated fatty acids and cardiovascular health: a comprehensive review. Prog Cardiovasc Dis. 2018;61(1):76–85. doi:10.1016/j.pcad.2018.03.006
  • Saini RK, Keum YS. Omega-3 and omega-6 polyunsaturated fatty acids: dietary sources, metabolism, and significance - a review. Life Sci. 2018;203:255–67. doi:10.1016/j.lfs.2018.04.049
  • Pagkalos VA, Moschandreas J, Kiriakakis M, Roussomoustakaki M, Kafatos A, Kouroumalis E. Fatty acid composition of subcutaneous adipose tissue and gastric mucosa: is there a relation with gastric ulceration?. BMC Gastroenterol. 2009;9:9doi:10.1186/1471-230X-9-9
  • Wu JHY, Micha R, Imamura F, Pan A, Biggs ML, Ajaz O, Djousse L, B. Hu F, Mozaffarian D. Omega-3 fatty acids and incident type 2 diabetes: a systematic review and meta-analysis. Br J Nutr. 2012;107(S2):S214–S227. doi:10.1017/S0007114512001602
  • Janssen CI, Kiliaan AJ. Long-chain polyunsaturated fatty acids (LCPUFA) from genesis to senescence: the influence of LCPUFA on neural development, aging, and neurodegeneration. Prog Lipid Res. 2014;53:1–17. doi:10.1016/j.plipres.2013.10.002
  • McDougle DR, Watson JE, Abdeen AA, Adili R, Caputo MP, Krapf JE, Johnson RW, Kilian KA, Holinstat M, Das A, et al. Anti-inflammatory ω-3 endocannabinoid epoxides. Proc Natl Acad Sci USA. 2017;114(30):E6034–6043. doi:10.1073/pnas.1610325114
  • Moloudizargari M, Mortaz E, Asghari MH, Adcock IM, Redegeld FA, Garssen J. Effects of the polyunsaturated fatty acids, EPA and DHA, on hematological malignancies: a systematic review. Oncotarget. 2018;9(14):11858–75. doi:10.18632/oncotarget.24405
  • Im DS. Omega-3 fatty acids in anti-inflammation (pro-resolution) and GPCRs. Prog Lipid Res. 2012;51(3):232–7. doi:10.1016/j.plipres.2012.02.003
  • Chen C, Yu X, Shao S. Effects of omega-3 fatty acid supplementation on glucose control and lipid levels in type 2 diabetes: a meta-analysis. PLoS One. 2015;10(10):e0139565. doi:10.1371/journal.pone.0139565
  • de Aguiar Pastore Silva J, Emilia de Souza Fabre M, Waitzberg DL. Omega-3 supplements for patients in chemotherapy and/or radiotherapy: a systematic review. Clin Nutr. 2015;34(3):359–66. doi:10.1016/j.clnu.2014.11.005
  • Khaddaj-Mallat R, Morin C, Rousseau É. Novel n-3 PUFA monoacylglycerides of pharmacological and medicinal interest: anti-inflammatory and anti-proliferative effects. Eur J Pharmacol. 2016;792:70–7. doi:10.1016/j.ejphar.2016.10.038
  • Sun M, Zhou Z, Dong J, Zhang J, Xia Y, Shu R. Antibacterial and antibiofilm activities of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) against periodontopathic bacteria. Microb Pathog. 2016;99:196–203. doi:10.1016/j.micpath.2016.08.025
  • Fuentes NR, Mlih M, Barhoumi R, Fan Y-Y, Hardin P, Steele TJ, Behmer S, Prior IA, Karpac J, Chapkin RS, et al. Long-chain n-3 fatty acids attenuate oncogenic KRas-driven proliferation by altering plasma membrane nanoscale proteolipid composition. Cancer Res. 2018;78(14):3899–912. doi:10.1158/0008-5472.CAN-18-0324
  • Yagaloff KA, Franco L, Simko B, Burghardt B. Essential fatty acids are antagonists of the leukotriene B4 receptor. Prostaglandins Leukot Essent Fatty Acids. 1995;52(5):293–7. doi:10.1016/0952-3278(95)90029-2
  • Henry GE, Momin RA, Nair MG, Dewitt DL. Antioxidant and cyclooxygenase activities of fatty acids found in food. J Agric Food Chem. 2002;50(8):2231–4. doi:10.1021/jf0114381
  • Yonezawa Y, Hada T, Uryu K, Iijima H, Yoshida H, Mizushina Y. Inhibitory action of C22-fatty acids on DNA polymerases and DNA topoisomerases. Int J Mol Med. 2006;18(4):583–8.
  • Candelario J, Chachisvilis M. Activity of bradykinin B2 receptor is regulated by long-chain polyunsaturated fatty acids. PLoS One. 2013;8(6):e68151. doi:10.1371/journal.pone.0068151
  • Meesapyodsuk D, Ye S, Chen Y, Chen Y, Chapman RG, Qiu X. An engineered oilseed crop produces oil enriched in two very long chain polyunsaturated fatty acids with potential health-promoting properties. Metab Eng. 2018;49:192–200. doi:10.1016/j.ymben.2018.08.009
  • Ling B, Gao B, Yang J. Evaluating the effects of tetrachloro-1,4-benzoquinone, an active metabolite of pentachlorophenol, on the growth of human breast cancer cells. J Toxicol. 2016;2016:8253726doi:10.1155/2016/8253726
  • Weylandt KH, Krause LF, Gomolka B, Chiu C-Y, Bilal S, Nadolny A, Waechter SF, Fischer A, Rothe M, Kang JX, et al. Suppressed liver tumorigenesis in fat-1 mice with elevated omega-3 fatty acids is associated with increased omega-3 derived lipid mediators and reduced TNF-α. Carcinogenesis. 2011;32(6):897–903. doi:10.1093/carcin/bgr049
  • Cui PH, Rawling T, Bourget K, Kim T, Duke CC, Doddareddy MR, Hibbs DE, Zhou F, Tattam BN, Petrovic N, et al. Antiproliferative and antimigratory actions of synthetic long chain n-3 monounsaturated fatty acids in breast cancer cells that overexpress cyclooxygenase-2. J Med Chem. 2012;55(16):7163–72. doi:10.1021/jm300673z
  • Abel S, Riedel S, Gelderblom WC. Dietary PUFA and cancer. Proc Nutr Soc. 2014;73(3):361–7. doi:10.1017/S0029665114000585
  • Liu J, Ma DW. The role of n-3 polyunsaturated fatty acids in the prevention and treatment of breast cancer. Nutrients. 2014;6(11):5184–223. doi:10.3390/nu6115184
  • Redza-Dutordoir M, Averill-Bates DA. Activation of apoptosis signalling pathways by reactive oxygen species. Biochim Biophys Acta. 2016;1863(12):2977–92. doi:10.1016/j.bbamcr.2016.09.012
  • Foyer CH, Wilson MH, Wright MH. Redox regulation of cell proliferation: Bioinformatics and redox proteomics approaches to identify redox-sensitive cell cycle regulators. Free Radic Biol Med. 2018;122:137–49. doi:10.1016/j.freeradbiomed.2018.03.047
  • Moldogazieva NT, Lutsenko SV, Terentiev AA. Reactive Oxygen and Nitrogen Species-Induced Protein Modifications: Implication in Carcinogenesis and Anticancer Therapy. Cancer Res. 2018;78(21):6040–7. doi:10.1158/0008-5472.CAN-18-0980
  • Liou GY, Storz P. Reactive oxygen species in cancer. Free Radic Res. 2010;44(5):479–96. doi:10.3109/10715761003667554
  • Peiris-Pagès M, Martinez-Outschoorn UE, Sotgia F, Lisanti MP. Metastasis and oxidative stress: are antioxidants a metabolic driver of progression?. Cell Metab. 2015;22(6):956–8. doi:10.1016/j.cmet.2015.11.008
  • Panieri E, Santoro MM. ROS homeostasis and metabolism: a dangerous liason in cancer cells. Cell Death Dis. 2016;7(6):e2253. doi:10.1038/cddis.2016.105
  • Nogueira V, Hay N. Molecular pathways: reactive oxygen species homeostasis in cancer cells and implications for cancer therapy. Clin Cancer Res. 2013;19(16):4309–14. doi:10.1158/1078-0432.CCR-12-1424
  • Wang J, Luo B, Li X, Lu W, Yang J, Hu Y, Huang P, Wen S. Inhibition of cancer growth in vitro and in vivo by a novel ROS-modulating agent with ability to eliminate stem-like cancer cells. Cell Death Dis. 2017;8(6):e2887doi:10.1038/cddis.2017.272
  • Finocchiaro C, Segre O, Fadda M, Monge T, Scigliano M, Schena M, Tinivella M, Tiozzo E, Catalano MG, Pugliese M, et al. Effect of n-3 fatty acids on patients with advanced lung cancer: a double-blind, placebo-controlled study. Br J Nutr. 2012;108(2):327–33. doi:10.1017/S0007114511005551
  • Shen J, Rastogi R, Guan L, Li F, Du H, Geng X, Ding Y. Omega-3 fatty acid supplement reduces activation of NADPH oxidase in intracranial atherosclerosis stenosis. Neurol Res. 2018;40(6):499–507. doi:10.1080/01616412.2018.1451290
  • Kello M, Mikes J, Jendzelovský R, Koval J, Fedorocko P. PUFAs enhance oxidative stress and apoptosis in tumour cells exposed to hypericin-mediated PDT. Photochem Photobiol Sci. 2010;9(9):1244–51. doi:10.1039/c0pp00085j
  • Yin Y, Sui C, Meng F, Ma P, Jiang Y. The omega-3 polyunsaturated fatty acid docosahexaenoic acid inhibits proliferation and progression of non-small cell lung cancer cells through the reactive oxygen species-mediated inactivation of the PI3K /Akt pathway. Lipids Health Dis. 2017;16(1):87. doi:10.1186/s12944-017-0474-x
  • Abdi J, Garssen J, Faber J, Redegeld FA. Omega-3 fatty acids, EPA and DHA induce apoptosis and enhance drug sensitivity in multiple myeloma cells but not in normal peripheral mononuclear cells. J Nutr Biochem. 2014;25(12):1254–62. doi:10.1016/j.jnutbio.2014.06.013
  • Zhang K, Hu Z, Qi H, Shi Z, Chang Y, Yao Q, Cui H, Zheng L, Han Y, Han X, et al. G-protein-coupled receptors mediate ω-3 PUFAs-inhibited colorectal cancer by activating the Hippo pathway. Oncotarget. 2016;7(36):58315–30. doi:10.18632/oncotarget.11089
  • Picou F, Debeissat C, Bourgeais J, Gallay N, Ferrié E, Foucault A, Ravalet N, Maciejewski A, Vallet N, Ducrocq E, et al. n-3 Polyunsaturated fatty acids induce acute myeloid leukemia cell death associated with mitochondrial glycolytic switch and Nrf2 pathway activation. Pharmacol Res. 2018;136:45–55. doi:10.1016/j.phrs.2018.08.015
  • Calder PC. Omega-3 polyunsaturated fatty acids and inflammatory processes: nutrition or pharmacology?. Br J Clin Pharmacol. 2013;75(3):645–62. doi:10.1111/j.1365-2125.2012.04374.x
  • Chen X, Chen C, Fan S, Wu S, Yang F, Fang Z, Fu H, Li Y. Omega-3 polyunsaturated fatty acid attenuates the inflammatory response by modulating microglia polarization through SIRT1-mediated deacetylation of the HMGB1/NF-κB pathway following experimental traumatic brain injury. J Neuroinflammation. 2018;15(1):116doi:10.1186/s12974-018-1151-3
  • Khadge S, Thiele GM, Sharp JG, McGuire TR, Klassen LW, Black PN, DiRusso CC, Cook L, Talmadge JE. Long-chain omega-3 polyunsaturated fatty acids decrease mammary tumor growth, multiorgan metastasis and enhance survival. Clin Exp Metastasis. 2018;35(8):797–818. doi:10.1007/s10585-018-9941-7
  • Mullen A, Loscher CE, Roche HM. Anti-inflammatory effects of EPA and DHA are dependent upon time and dose-response elements associated with LPS stimulation in THP-1-derived macrophages. J Nutr Biochem. 2010;21(5):444–50. doi:10.1016/j.jnutbio.2009.02.008
  • Jaudszus A, Gruen M, Watzl B, Ness C, Roth A, Lochner A, Barz D, Gabriel H, Rothe M, Jahreis G, et al. Evaluation of suppressive and pro-resolving effects of EPA and DHA in human primary monocytes and T-helper cells. J Lipid Res. 2013;54(4):923–35. doi:10.1194/jlr.P031260
  • Armstrong L, Jordan N, Millar A. Interleukin 10 (IL-10) regulation of tumour necrosis factor alpha (TNF-alpha) from human alveolar macrophages and peripheral blood monocytes. Thorax. 1996;51(2):143–9. doi:10.1136/thx.51.2.143
  • Brennan FM, Green P, Amjadi P, Robertshaw HJ, Alvarez-Iglesias M, Takata M. Interleukin-10 regulates TNF-alpha-converting enzyme (TACE/ADAM-17) involving a TIMP-3 dependent and independent mechanism. Eur J Immunol. 2008;38(4):1106–17. doi:10.1002/eji.200737821
  • Kim N, Jeong S, Jing K, Shin S, Kim S, Heo J-Y, Kweon G-R, Park S-K, Wu T, Park J-I, et al. Docosahexaenoic acid induces cell death in human non-small cell lung cancer cells by repressing mTOR via AMPK activation and PI3K/Akt inhibition. Biomed Res Int. 2015;2015:239764 doi:10.1155/2015/239764
  • Serini S, Calviello G. Modulation of Ras/ERK and phosphoinositide signaling by long-chain n-3 PUFA in breast cancer and their potential complementary role in combination with targeted drugs. Nutrients. 2017;9(3):185. doi:10.3390/nu9030185
  • Schaefer MB, Schaefer CA, Schifferings S, Kuhlmann CRW, Urban A, Benscheid U, Fischer T, Hecker M, Morty RE, Vadasz I, et al. N-3 vs. n-6 fatty acids differentially influence calcium signalling and adhesion of inflammatory activated monocytes: impact of lipid rafts. Inflamm Res. 2016;65(11):881–94. doi:10.1007/s00011-016-0971-9
  • Pilkington SM, Rhodes LE, Al-Aasswad NM, Massey KA, Nicolaou A. Impact of EPA ingestion on COX- and LOX-mediated eicosanoid synthesis in skin with and without a pro-inflammatory UVR challenge–report of a randomised controlled study in humans. Mol Nutr Food Res. 2014;58(3):580–90. doi:10.1002/mnfr.201300405
  • Reifen R, Karlinsky A, Stark AH, Berkovich Z, Nyska A. α-Linolenic acid (ALA) is an anti-inflammatory agent in inflammatory bowel disease. J Nutr Biochem. 2015;26(12):1632–40. doi:10.1016/j.jnutbio.2015.08.006
  • Siddiquee A, Patel M, Rajalingam S, Narke D, Kurade M, Ponnoth DS. Effect of omega-3 fatty acid supplementation on resolvin (RvE1)-mediated suppression of inflammation in a mouse model of asthma. Immunopharmacol Immunotoxicol. 2019;41(2):250–7. doi:10.1080/08923973.2019.1584903
  • Serhan CN, Clish CB, Brannon J, Colgan SP, Chiang N, Gronert K. Novel functional sets of lipid-derived mediators with antiinflammatory actions generated from omega-3 fatty acids via cyclooxygenase 2-nonsteroidal antiinflammatory drugs and transcellular processing. J Exp Med. 2000;192(8):1197–204. doi:10.1084/jem.192.8.1197
  • Han L, Zhang Y, Meng M, Cheng D, Wang C. Eicosapentaenoic acid induced SKOV-3 cell apoptosis through ERK1/2-mTOR-NF-κB pathways. Anticancer Drugs. 2016;27(7):635–42. doi:10.1097/CAD.0000000000000373
  • Ichimura A, Hirasawa A, Poulain-Godefroy O, Bonnefond A, Hara T, Yengo L, Kimura I, Leloire A, Liu N, Iida K, et al. Dysfunction of lipid sensor GPR120 leads to obesity in both mouse and human. Nature. 2012;483(7389):350–4. doi:10.1038/nature10798
  • Wu Q, Wang H, Zhao X, Shi Y, Jin M, Wan B, Xu H, Cheng Y, Ge H, Zhang Y, et al. Identification of G-protein-coupled receptor 120 as a tumor-promoting receptor that induces angiogenesis and migration in human colorectal carcinoma. Oncogene. 2013;32(49):5541–50. doi:10.1038/onc.2013.264
  • Amos D, Cook C, Santanam N. Omega 3 rich diet modulates energy metabolism via GPR120-Nrf2 crosstalk in a novel antioxidant mouse model. Biochim Biophys Acta Mol Cell Biol Lipids. 2019;1864(4):466–88. doi:10.1016/j.bbalip.2019.01.002
  • Liang P, Henning SM, Guan J, Grogan T, Elashoff D, Olefsky JM, Cohen P, Aronson WJ. Role of host GPR120 in mediating dietary omega-3 fatty acid inhibition of prostate cancer. J Natl Cancer Inst. 2019;111(1):52–9. doi:10.1093/jnci/djy125
  • Pupe A, Moison R, De Haes P, van Henegouwen GB, Rhodes L, Degreef H, Garmyn M. Eicosapentaenoic acid, a n-3 polyunsaturated fatty acid differentially modulates TNF-alpha, IL-1alpha, IL-6 and PGE2 expression in UVB-irradiated human keratinocytes. J Invest Dermatol. 2002;118(4):692–8. doi:10.1046/j.1523-1747.2002.01615.x
  • Pidgeon GP, Lysaght J, Krishnamoorthy S, Reynolds JV, O'Byrne K, Nie D, Honn KV. Lipoxygenase metabolism: roles in tumor progression and survival. Cancer Metastasis Rev. 2007;26(3-4):503–24. doi:10.1007/s10555-007-9098-3
  • Yum H-W, Park J, Park H-J, Shin JW, Cho Y-Y, Kim S-J, Kang JX, Surh Y-J. Endogenous ω-3 Fatty Acid Production by fat-1 Transgene and Topically Applied Docosahexaenoic Acid Protect against UVB-induced Mouse Skin Carcinogenesis. Sci Rep. 2017;7(1):11658doi:10.1038/s41598-017-11443-2
  • Wannous R, Bon E, Mahéo K, Goupille C, Chamouton J, Bougnoux P, Roger S, Besson P, Chevalier S. PPARβ mRNA expression, reduced by n-3 PUFA diet in mammary tumor, controls breast cancer cell growth. Biochim Biophys Acta. 2013;1831(11):1618–25. doi:10.1016/j.bbalip.2013.07.010
  • Edwards IJ, O'Flaherty JT. Omega-3 Fatty Acids and PPARgamma in Cancer. PPAR Res. 2008;2008:3580522008. doi:10.1155/2008/358052
  • Rovito D, Giordano C, Plastina P, Barone I, De Amicis F, Mauro L, Rizza P, Lanzino M, Catalano S, Bonofiglio D, et al. Omega-3 DHA- and EPA-dopamine conjugates induce PPARγ-dependent breast cancer cell death through autophagy and apoptosis. Biochim Biophys Acta. 2015;1850(11):2185–95. doi:10.1016/j.bbagen.2015.08.004
  • Ceccarelli V, Nocentini G, Billi M, Racanicchi S, Riccardi C, Roberti R, Grignani F, Binaglia L, Vecchini A. Eicosapentaenoic acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. PLoS One. 2014;9(1):e85025doi:10.1371/journal.pone.0085025
  • Lu CY, Li CC, Liu KL, Lii CK, Chen HW. Docosahexaenoic acid downregulates phenobarbital-induced cytochrome P450 2B1 gene expression in rat primary hepatocytes via the c-Jun NH2-terminal kinase mitogen-activated protein kinase pathway. Mol Nutr Food Res. 2009;53(3):341–8. doi:10.1002/mnfr.200800112
  • Zhang Z, Guo M, Zhao S, Shao J, Zheng S. ROS-JNK1/2-dependent activation of autophagy is required for the induction of anti-inflammatory effect of dihydroartemisinin in liver fibrosis. Free Radic Biol Med. 2016;101:272–83. doi:10.1016/j.freeradbiomed.2016.10.498
  • Faria M, Domingues R, Paixão F, Bugalho MJ, Matos P, Silva AL. TNFα-mediated activation of NF-κB downregulates sodium-iodide symporter expression in thyroid cells. PLoS One. 2020;15(2):e0228794. doi:10.1371/journal.pone.0228794
  • Azrad M, Turgeon C, Demark-Wahnefried W. Current evidence linking polyunsaturated Fatty acids with cancer risk and progression. Front Oncol. 2013;3:224doi:10.3389/fonc.2013.00224
  • Xu Y, Qian SY. Anti-cancer activities of ω-6 polyunsaturated fatty acids. Biomed J. 2014;37(3):112–9. doi:10.4103/2319-4170.131378
  • Zanoaga O, Jurj A, Raduly L, Cojocneanu-Petric R, Fuentes-Mattei E, Wu O, Braicu C, Gherman CD, Berindan-Neagoe I. Implications of dietary ω-3 and ω-6 polyunsaturated fatty acids in breast cancer. Exp Ther Med. 2018;15(2):1167–76. doi:10.3892/etm.2017.5515
  • Gago-Dominguez M, Yuan JM, Sun CL, Lee HP, Yu MC. Opposing effects of dietary n-3 and n-6 fatty acids on mammary carcinogenesis: The Singapore Chinese Health Study. Br J Cancer. 2003;89(9):1686–92. doi:10.1038/sj.bjc.6601340
  • Murff HJ, Shu X-O, Li H, Yang G, Wu X, Cai H, Wen W, Gao Y-T, Zheng W. Dietary polyunsaturated fatty acids and breast cancer risk in Chinese women: a prospective cohort study. Int J Cancer. 2011;128(6):1434–41. doi:10.1002/ijc.25703

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.