10(S),17(S)-DiHDoHE

Description

Protectin D₁ (also known as neuroprotectin D₁ when produced in neuronal tissues) is a DHA-derived dihydroxy fatty acid that exhibits potent protective and anti-inflammatory activities.^1,2,3 10(S),17(S)-DiHDHA is a DHA metabolite, also referred to as protectin DX (PDX).⁴ It is produced by an apparent double lipoxygenase (LO)-mediated reaction in murine peritonitis exudates, in suspensions of human leukocytes, or by soybean 15-LO incubated with DHA.^1,4 It differs from protectin D₁ with respect to the stereochemistry of the C-10 hydroxyl and the double bond configuration at the 13 and 15 positions. 10(S),17(S)-DiHDHA blocks neutrophil infiltration in murine peritonitis by 20-25% at a dose of 1 ng/mouse.¹ It also inhibits platelet activation by both impairing thromboxane (TX) synthesis and TX receptor activation.^4,5

Definition

ChEBI: (4Z,7Z,10S,11E,13Z,15E,17S,19Z)-10,17-dihydroxydocosahexaenoic acid is a dihydroxydocosahexaenoic acid that is (4Z,7Z,11E,13Z,15E,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at positions 10 and 17 (the 10S,17S-stereoisomer). A natural isomer of protectin D1, one of the specialised proresolving mediators. It has a role as an anti-inflammatory agent and a human xenobiotic metabolite. It is a dihydroxydocosahexaenoic acid, a secondary allylic alcohol and a protectin.

References

1. Serhan, C.N., Gotlinger, K., Hong, S., et al. Anti-inflammatory actions of neuroprotectin D₁/protectin D₁ and its natural stereoisomers: Assignments of dihydroxy-containing docosatrienes J. Immunol. 176(3),1848-1859(2006).
2. Ariel, A., and Serhan, C.N. Resolvins and protectins in the termination program of acute inflammation Trends Immunol. 28(4),176-183(2007).
3. Schwab, J.M., Chiang, N., Arita, M., et al. Resolvin E1 and protectin D₁ activate inflammation-resolution programmes Nature 447(7146),869-874(2007).
4. Chen, P., Fenet, B., Michaud, S., et al. Full characterization of PDX, a neuroprotectin/protectin D₁ isomer, which inhibits blood platelet aggregation FEBS Lett. 583,3478-3484(2009).
5. Chen, P., Véricel, E., Lagarde, M., et al. Poxytrins, a class of oxygenated products from polyunsaturated fatty acids, potently inhibit blood platelet aggregation FASEB J. 25,382-388(2011).