CHE 211 Study Guide - Final Guide: Oily Fish, Essential Fatty Acid, Thromboxane
Organic Chemistry 2: Lipids
Eicosanoids: Prostaglandins, Leukotrienes, and Thromboxanes
Fatty aids whih a’t e sythesized y the ody are essential fatty acids (Linoleic acid
is an essential fatty acid required to make arachidonic acid
Linoleic acid is a precursor to arachidonic acid
Arachidonic acid (20C) is the eicosanoid precursor
Eicosanoids are three groups of structurally related compounds; eicosanoids derived
from oxidizing arachidonic 20 carbon derivative that functions as a messenger lipid
► Three types of eicosanoids are: Prostaglandins, Leukotrienes, Thromboxanes
Prostaglandins
▪ Potent biological molecules
▪ They act like horoes i otrollig the ody ’s proesses
▪ Structure
– Synthesized from 20-carbon unsaturated fatty acids (contains a 20C chain)
– Contain cyclic compounds including a 5-carbon ring
– Oxygen containing functional group such as hydroxyl groups
▪ Names are based on ring substituents and number of side-chain double bonds
▪ Prostaglandins were named after the prostate gland because it was thought that
that was the only role in the body; today, more than 20 prostaglandins have
been isolated from a variety of tissues from both men and women
▪ Made in most tissues
– Exert their effects on cells that produce them and cells in the immediate
vicinity
Biological Processes Regulated by Eicosanoids
1) Blood Clotting (Both thromboxanes and prostaglandins play a role)
▪ Thromboxane A2 stimulates constriction of blood vessels and platelet
aggregation
▪ Prostacyclin dilates blood vessels and inhibits platelet aggregation
2) Inflammatory Response
o Prostaglandins mediate aspects of inflammatory response (especially dealing
with pain and fever)
3) Reproductive System
Stimulation of smooth muscle by PGE2 (this is just a specific prostaglandin that
stimulates specifically uterine contractions)
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Document Summary
Fatty a(cid:272)ids whi(cid:272)h (cid:272)a(cid:374)"t (cid:271)e sy(cid:374)thesized (cid:271)y the (cid:271)ody are essential fatty acids (linoleic acid is an essential fatty acid required to make arachidonic acid. Linoleic acid is a precursor to arachidonic acid. Arachidonic acid (20c) is the eicosanoid precursor. Eicosanoids are three groups of structurally related compounds; eicosanoids derived from oxidizing arachidonic 20 carbon derivative that functions as a messenger lipid. Three types of eicosanoids are: prostaglandins, leukotrienes, thromboxanes. Prostaglandins: potent biological molecules, they act like hor(cid:373)o(cid:374)es i(cid:374) (cid:272)o(cid:374)trolli(cid:374)g the (cid:271)ody "s pro(cid:272)esses, structure. Synthesized from 20-carbon unsaturated fatty acids (contains a 20c chain) Contain cyclic compounds including a 5-carbon ring. Exert their effects on cells that produce them and cells in the immediate vicinity. Stimulation of smooth muscle by pge2 (this is just a specific prostaglandin that stimulates specifically uterine contractions: gastrointestinal tract, prostaglandins inhibit gastric secretion and increase secretion of protective mucus in the stomach. Prostaglandins produced in the kidney dilate renal blood vessels.
