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26.6 Prostaglandins

26.6 Prostaglandins. Prostaglandins. Prostaglandins are involved in many biological processes. Are biosynthesized from linoleic acid (C 18 ) via arachidonic acid (C 20 ). (See Table 26.1). O. O. OH. HO. OH. O. HO. OH. HO. OH. Examples: PGE 1 and PGF 1 . PGE 1. PGF 1 .

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26.6 Prostaglandins

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  1. 26.6Prostaglandins

  2. Prostaglandins Prostaglandins are involved in many biological processes. Are biosynthesized from linoleic acid (C18) via arachidonic acid (C20). (See Table 26.1)

  3. O O OH HO OH O HO OH HO OH Examples: PGE1 and PGF1 PGE1 PGF1

  4. Prostaglandin Biosynthesis PGE2 is biosynthesized from arachidonic acid The oxygens come from O2 The enzyme involved (prostaglandin endoperoxide synthase) has cyclooxygenase (COX) acitivity

  5. CO2H CH3 O CO2H PGG2 O CH3 HOO Prostaglandin Biosynthesis Arachidonic acid O2fatty acid cyclooxygenase

  6. O CO2H PGH2 O CH3 HO O CO2H PGG2 O CH3 HOO Prostaglandin Biosynthesis reduction ofhydroperoxide

  7. O CO2H PGH2 O CH3 HO O CO2H CH3 PGE2 HO HO Prostaglandin Biosynthesis

  8. Icosanoids Icosanoids are compounds related to icosanoic acid CH3(CH2)18CO2H. Icosanoids include: prostaglandinsthromboxanesprostacyclinsleukotrienes

  9. O CO2H PGH2 O CH3 HO O O CO2H TXA2 CH3 HO Thromboxane A2 (TXA2) Thromboxane A2 is biosynthesized from PGH2 TXA2 promotes platelet aggregation and blood clotting

  10. HO2C O CH3 HO OH Prostacyclin I2 (PGI2) Like thromboxane A2, prostacyclin I2 isbiosynthesized from PGH2 PGI2 inhibits platelet aggregation and relaxescoronary arteries PGI2

  11. Leukotriene C4 (LTC4) Leukotrienes arise from arachidonic acid viaa different biosynthetic pathway. They are thesubstances most responsible for constrictingbronchial passages during asthma attacks.

  12. OH CO2H CH3 O S O – NH O2CCHCH2CH2 CH2CHCNHCH2CO2H C + NH3 Leukotriene C4 (LTC4)

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