Prostanoid

Prostanoid is the term used to describe a subclass of eicosanoids consisting of: the prostaglandins (mediators of inflammatory and anaphylactic reactions), the thromboxanes (mediators of vasoconstriction) and the prostacyclins (active in the resolution phase of inflammation.)

See also main articles at Prostaglandin, Prostacyclin and Thromboxane

Biosynthesis

Prostaglandin H₂

PGD synthase

PGD₂

PGJ₂

PGE
synthase

PGE₂

PGA₂

PGB₂

Prostacyclin synthase

PGI₂

6-keto-PGFα

PGE
9-ketoreductase

PGF₂

Thromboxane-A
synthase

TXA₂

Cyclooxygenase (COX) catalyzes the conversion of the free essential fatty acids to prostanoids by a two-step process. In the first step, two molecules of O₂ are added as two peroxide linkages and a 5-member carbon ring is forged near the middle of the fatty acid chain. This forms the short-lived, unstable intermediate Prostaglandin G (PGG). One of the peroxide linkages sheds a single oxygen, forming PGH. (See diagrams and more detail at Cyclooxygenase). All other prostanoids originate from PGH (as PGH₁, PGH₂, or PGH₃).

Figure 1 shows how PGH₂ (derived from Arachidonic acid) is converted:

• By PGE synthetase into PGE (which in turn is converted into PGF)
• By PGD synthetase into PGD
• By Prostacyclin synthase into prostacyclin (PGI2)
• By Thromboxane synthase into thromboxanes

The three classes of prostanoids have distinctive rings in the center of the molecule. They differ in their structures. The PGH compounds (parents to all the rest) have a 5-carbon ring, bridged by two oxygens (a peroxide.) The derived prostaglandins contain a single, unsaturated 5-carbon ring. In prostacyclins, this ring is conjoined to another oxygen-containing ring. In thromboxanes the ring becomes a 6-member ring with one oxygen.

Production of PGE₂ in bacterial and viral infections appears to be stimulated by certain cytokines, e.g., interleukin-1.^[1]

See also

• Essential fatty acid
• Isoprostane

References

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