Leukotriene B5 (BioDeep_00000018518)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(5S,6Z,8E,10E,12R,14Z,17Z)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid

化学式: C20H30O4 (334.214398)
中文名称: 白[细胞]三烯 b5, 白三烯B5
谱图信息: 最多检出来源 Mus musculus(blood) 50%

Reviewed

Last reviewed on 2024-10-24.

Cite this Page

Leukotriene B5. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/leukotriene_b5 (retrieved 2024-11-23) (BioDeep RN: BioDeep_00000018518). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCC=CCC=CCC(C=CC=CC=CC(CCCC(=O)O)O)O
InChI: InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3-,8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

描述信息

Leukotriene B5 (LTB5) is a 5-lipoxygenase metabolite of arachidonic (AA) and eicosapentaenoic acid (EPA), involved in numerous inflammatory diseases and possesses a substantially less potent inflammatory effect than LTB4. Binding of LTB5 to human neutrophil LTB4 high affinity binding sites is lower than that of LTB4. Polymorphonuclear leukocytes isolated from volunteers who ingested eicosapentaenoic acid (EPA) form LTB5. Enrichment of human neutrophils with EPA, by dietary supplementation for at least 3 weeks, reduces their formation of LTB4 ex vivo. LTB5 is catabolized to 20-OH-LTB5, which in turn is metabolized to 20-COOH-LTB5. Presumably the same enzyme systems are involved in the catabolism of LTB5 that are responsible for catabolism of LTB4. Fish oil supplementation has a protective effect on exercise-induced bronchoconstriction (EIB) in elite athletes, which may be attributed to its antiinflammatory properties due to a significant reduction in LTB4 and a significant increase in LTB5 generation from activated polymorphonuclear leukocytes (PMNLs). (PMID: 1964169, 15866528, 2538061, 16424411). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Leukotriene B5 (LTB5) is a 5-lipoxygenase metabolite of arachidonic (AA) and eicosapentaenoic acid (EPA), involved in numerous inflammatory diseases and possesses a substantially less potent inflammatory effect than LTB4. Binding of LTB5 to human neutrophil LTB4 high affinity binding sites is lower than that of LTB4. Polymorphonuclear leukocytes isolated from volunteers who ingested eicosapentaenoic acid (EPA) form LTB5. Enrichment of human neutrophils with EPA, by dietary supplementation for at least 3 weeks, reduces their formation of LTB4 ex vivo. LTB5 is catabolized to 20-OH-LTB5, which in turn is metabolized to 20-COOH-LTB5. Presumably the same enzyme systems are involved in the catabolism of LTB5 that are responsible for catabolism of LTB4. Fish oil supplementation has a protective effect on exercise-induced bronchoconstriction (EIB) in elite athletes, which may be attributed to its antiinflammatory properties due to a significant reduction in LTB4 and a significant increase in LTB5 generation from activated polymorphonuclear leukocytes (PMNLs). (PMID: 1964169, 15866528, 2538061, 16424411)

同义名列表

11 个代谢物同义名

(5S,6Z,8E,10E,12R,14Z,17Z)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid; (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoic acid; (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoate; 5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoic acid; 5,12-Dihydroxy-6-trans-leukotriene b(5); 5,12-Dihydroxy-6E-LTB5; leukotriene b5; 5,12-DiHEPE; DB-056436; LTB 5; LTB5



数据库引用编号

8 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Anne E Barden, Sujata Shinde, Valerie Burke, Ian B Puddey, Lawrence J Beilin, Ashley B Irish, Gerald F Watts, Trevor A Mori. The effect of n-3 fatty acids and coenzyme Q10 supplementation on neutrophil leukotrienes, mediators of inflammation resolution and myeloperoxidase in chronic kidney disease. Prostaglandins & other lipid mediators. 2018 05; 136(?):1-8. doi: 10.1016/j.prostaglandins.2018.03.002. [PMID: 29577973]
  • Elisabeth Holen, Juyun He, Marit Espe, Liqiou Chen, Pedro Araujo. Combining eicosapentaenoic acid, decosahexaenoic acid and arachidonic acid, using a fully crossed design, affect gene expression and eicosanoid secretion in salmon head kidney cells in vitro. Fish & shellfish immunology. 2015 Aug; 45(2):695-703. doi: 10.1016/j.fsi.2015.05.017. [PMID: 26003739]
  • Mark K Waldron, Steven S Hannah, John E Bauer. Plasma phospholipid fatty acid and ex vivo neutrophil responses are differentially altered in dogs fed fish- and linseed-oil containing diets at the same n-6:n-3 fatty acid ratio. Lipids. 2012 Apr; 47(4):425-34. doi: 10.1007/s11745-012-3652-7. [PMID: 22252853]
  • T Maaløe, E B Schmidt, M Svensson, I V Aardestrup, J H Christensen. The effect of n-3 polyunsaturated fatty acids on leukotriene B₄ and leukotriene B₅ production from stimulated neutrophil granulocytes in patients with chronic kidney disease. Prostaglandins, leukotrienes, and essential fatty acids. 2011 Jul; 85(1):37-41. doi: 10.1016/j.plefa.2011.04.004. [PMID: 21530211]
  • Hyun Joo Park, Jean Soon Park, Michael G Hayek, Gregory A Reinhart, Boon P Chew. Dietary fish oil and flaxseed oil suppress inflammation and immunity in cats. Veterinary immunology and immunopathology. 2011 Jun; 141(3-4):301-6. doi: 10.1016/j.vetimm.2011.02.024. [PMID: 21440312]
  • Akifumi Hagi, Mitsuo Nakayama, Wataru Shinzaki, Seiji Haji, Harumasa Ohyanagi. Effects of the omega-6:omega-3 fatty acid ratio of fat emulsions on the fatty acid composition in cell membranes and the anti-inflammatory action. JPEN. Journal of parenteral and enteral nutrition. 2010 May; 34(3):263-70. doi: 10.1177/0148607109357625. [PMID: 20467008]
  • Françoise Stanke-Labesque, Patrick Molière, Jeanine Bessard, Martine Laville, Evelyne Véricel, Michel Lagarde. Effect of dietary supplementation with increasing doses of docosahexaenoic acid on neutrophil lipid composition and leukotriene production in human healthy volunteers. The British journal of nutrition. 2008 Oct; 100(4):829-33. doi: 10.1017/s0007114508923692. [PMID: 18304388]
  • J A Hall, L R Henry, S Jha, M M Skinner, D E Jewell, R C Wander. Dietary (n-3) fatty acids alter plasma fatty acids and leukotriene B synthesis by stimulated neutrophils from healthy geriatric Beagles. Prostaglandins, leukotrienes, and essential fatty acids. 2005 Nov; 73(5):335-41. doi: 10.1016/j.plefa.2005.07.006. [PMID: 16146686]
  • K Engström, R Wallin, T Saldeen. Effect of low-dose aspirin in combination with stable fish oil on whole blood production of eicosanoids. Prostaglandins, leukotrienes, and essential fatty acids. 2001 Jun; 64(6):291-7. doi: 10.1054/plef.2001.0275. [PMID: 11427037]
  • P Hung, J Y Gu, S Kaku, S Yunoki, K Ohkura, I Ikeda, H Tachibana, M Sugano, K Yazawa, K Yamada. Dietary effects of eicosapentaenoic and docosahexaenoic acid esters on lipid metabolism and immune parameters in Sprague-Dawley rats. Bioscience, biotechnology, and biochemistry. 2000 Dec; 64(12):2588-93. doi: 10.1271/bbb.64.2588. [PMID: 11210121]
  • K A Munger, A Montero, M Fukunaga, S Uda, T Yura, E Imai, Y Kaneda, J M Valdivielso, K F Badr. Transfection of rat kidney with human 15-lipoxygenase suppresses inflammation and preserves function in experimental glomerulonephritis. Proceedings of the National Academy of Sciences of the United States of America. 1999 Nov; 96(23):13375-80. doi: 10.1073/pnas.96.23.13375. [PMID: 10557328]
  • K Løssl, H A Skou, J H Christensen, E B Schmidt. The effect of n-3 fatty acids on leukotriene formation from neutrophils in patients on hemodialysis. Lipids. 1999; 34 Suppl(?):S185. doi: 10.1007/bf02562283. [PMID: 10419143]
  • N Nakamura, T Hamazaki, K Yamazaki, H Taki, M Kobayashi, K Yazawa, F Ibuki. Intravenous infusion of tridocosahexaenoyl-glycerol emulsion into rabbits. Effects on leukotriene B4/5 production and fatty acid composition of plasma and leukocytes. The Journal of clinical investigation. 1993 Sep; 92(3):1253-61. doi: 10.1172/jci116697. [PMID: 8397222]
  • F H Chilton, M Patel, A N Fonteh, W C Hubbard, M Triggiani. Dietary n-3 fatty acid effects on neutrophil lipid composition and mediator production. Influence of duration and dosage. The Journal of clinical investigation. 1993 Jan; 91(1):115-22. doi: 10.1172/jci116159. [PMID: 8380809]
  • A Ikehata, N Hiwatashi, Y Kinouchi, H Yamazaki, Y Kumagai, K Ito, Y Kayaba, T Toyota. Effect of intravenously infused eicosapentaenoic acid on the leukotriene generation in patients with active Crohn's disease. The American journal of clinical nutrition. 1992 Nov; 56(5):938-42. doi: 10.1093/ajcn/56.5.938. [PMID: 1329484]
  • A B Hawthorne, T K Daneshmend, C J Hawkey, A Belluzzi, S J Everitt, G K Holmes, C Malkinson, M Z Shaheen, J E Willars. Treatment of ulcerative colitis with fish oil supplementation: a prospective 12 month randomised controlled trial. Gut. 1992 Jul; 33(7):922-8. doi: 10.1136/gut.33.7.922. [PMID: 1353742]
  • C von Schacky, C Fahrer, S Fischer. Catabolism of leukotriene B5 in humans. Journal of lipid research. 1990 Oct; 31(10):1831-8. doi: . [PMID: 1964169]
  • L G Cleland, M J James, R A Gibson, J S Hawkes, W H Betts. Effect of dietary oils on the production of n-3 and n-6 metabolites of leukocyte 5-lipoxygenase in five rat strains. Biochimica et biophysica acta. 1990 Apr; 1043(3):253-8. doi: 10.1016/0005-2760(90)90024-r. [PMID: 2157490]
  • T H Lee, E Israel, J M Drazen, A G Leitch, J Ravalese, E J Corey, D R Robinson, R A Lewis, K F Austen. Enhancement of plasma levels of biologically active leukotriene B compounds during anaphylaxis in guinea pigs pretreated by indomethacin or by a fish oil-enriched diet. Journal of immunology (Baltimore, Md. : 1950). 1986 Apr; 136(7):2575-82. doi: . [PMID: 3005414]
  • T Terano, J A Salmon, S Moncada. Biosynthesis and biological activity of leukotriene B5. Prostaglandins. 1984 Feb; 27(2):217-32. doi: 10.1016/0090-6980(84)90075-3. [PMID: 6326200]