LIPID MAPS

Leukotrienes (LTs) are a group of acute inflammatory mediators derived from arachidonic acid in leukocytes. The majority of these metabolites are formed through the 5-lipoxygenase (5-LO) pathway.¹ 14,15-LTC4 is a member of an alternate class of LTs synthesized by a pathway involving the dual actions of 15- and 12-LOs on arachidonic acid via 15-HpETE and 14,15-LTA4 intermediates.^2,3,4,5 14,15-LTC4 is classified as an eoxin, because it is formed mostly by eosinophils.⁴ However, mast cells and nasal polyps can synthesize 14,15-LTC4 as well. Little is known about the physiological actions of 14,15-LTC4. It has weak contractile activity on both guinea pig ileum and pulmonary parenchyma in contrast to the effects of 5-LO-derived LTs.^6,7 However, in an in vitro permeability assay, 14,15-LTC4 can increase vascular permeability of human endothelial cell monolayers, with similar potency to that of 5-LO-derived LTs resulting in plasma leakage - a hallmark of inflammation.⁴

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References

1. Luo, M., Lee, S., and Brock, T.G. Leukotriene synthesis by epithelial cells. Histol. Histopathol. 18(2), 587-595 (2003).

2. Yokoyama, C., Shinjo, F., Yoshimoto, T., et al. Arachidonate 12-lipoxygenase purified from porcine leukocytes by immunoaffinity chromatography and its reactivity with hydroperoxyeicosatetraenoic acids. The Journal of Biological Chemisty 261(35), 16714-16721 (1986).

3. Bryant, R.W., Schewe, T., Rapoport, S.M., et al. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14,15-leukotriene A4. The Journal of Biological Chemisty 260(6), 3548-3555 (1985).

4. Feltenmark, S., Gautam, N., Brunnström, Å., et al. Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells. Proc. Natl. Acad. Sci. USA 105(2), 680-685 (2008).

5. Sailesh, S., Kumar, Y.V.K., Prasad, M., et al. Sheep uterus dual lipoxygenase in the synthesis of 14,15-leukotrienes. Arch. Biochem. Biophys. 315(2), 362-368 (1994).

6. Drazen, J.M., Lewis, R.A., Austen, K.F., et al. Contractile activities of structural analogs of leukotrienes C and D: Necessity of a hydrophobic region. Proc. Natl. Acad. Sci. USA 78(5), 3195-3198 (1987).

7. Sala, A., Civelli, M., Oliva, D., et al. Contractile and binding activities of structural analogues of LTC4 in the longitudinal muscle of guinea-pig ileum. Eicosanoids 3(2), 105-110 (1990).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

On the biosynthesis and biological role of eoxins and 15-lipoxygenase-1 in airway inflammation and Hodgkin lymphoma.,
Prostaglandins Other Lipid Mediat, 2009

Pubmed ID: 19130894

InChiKey (Click to copy)

OBQVBASHEWLKCQ-PKBWNXTMSA-N

InChi (Click to copy)

InChI=1S/C30H47N3O9S/c1-2-3-12-15-24(34)25(16-13-10-8-6-4-5-7-9-11-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h4,6-10,13,16,22-25,34H,2-3,5,11-12,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b6-4-,9-7-,10-8+,16-13+/t22-,23-,24-,25+/m0/s1

SMILES (Click to copy)

C(CCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(O)=O)[C@@H](O)CCCCC)(=O)O

CHEBI ID

63984

PubChem CID

42607303

Cayman ID

10011360

Heavy Atoms 43

Rings 0

Aromatic Rings 0

Rotatable Bonds 25