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Steroids and Isoprenoids, Part A: Volume 110
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All are derived from essential polyunsaturated fatty acids — arachidonic acid eicosatetraenoic, abbr. ETE 5,8,11,14 from the n -6 series, and — eicosapentaenoic acid abbr.
EPE 5,8,11,14,17 from the n -3 series. COO — 3. There are two major types of eicosanoids : — cyclic prostanoids , which can be held as derivatives of an unnatural carbon fatty acid containing a 5-carbon cyclopentane ring called prostanoic acid: prostaglandins , prostacyclins , and related thromboxanes ; — acyclic leukotrienes and lipoxins C OO — 4. Cyclic eicosanoids - prostanoids: Prostaglandins Although prostaglandins are synthesized in nearly all cell types , the name denotes the tissue from which they were isolated for the first time the prostate gland.. Prostanoids with the subscript 2 two double bonds in the side chains are members of the second or diene series that is synthesized from arachidonate n -6 , the other two double bonds of the precursor are lost in forming a ring.
Steroids and isoprenoids. Part A. - Semantic Scholar
Those with the subscript 3 - the third or triene series are synthesized from eicosapentaenoic acid n Thromboxanes originate through transformation of the common precursor of all prostanoids — endoperoxide PGH. Instead of cyclopentane ring, those compounds contain a six-membered heterocycle oxane.
The name denotes that they are specific products of thrombocytes blood platelets. Thromboxane TXA 2 9. Acyclic eicosanoids: Leukotrienes The characteristic feature of these acyclic carbon compounds produced primarily in leuko cytes and mast cells is the presence of three conjugated double bonds trienes , the position of which may be different and the configuration either trans or cis.
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Leukotrienes are the most effective eicosanoids, e. Isoprenoids Isoprenoids are a family of natural products whose structures are composed of five-carbon isoprene units. The unit consists of a four-carbon chain with a one-carbon branch at carbon 2.
Steroids and Isoprenoids, Part B, Vol 111. Methods in Enzymology
Isoprene 2-methylbuta-1,3-diene Isoprene unit of polymers Terpenes are isoprenoids mainly of plant origin that can be isolated from essential oils of plants. Some terpenes play also an important role in metabolism of animals. Numerous terpenes contain various functional group mostly alcoholic or phenolic hydroxyl, carbonyl , may be saturated or unsaturated, acyclic or cyclic.
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According to the number of isoprene units comprising the molecules, terpenes are classified as monoterpenes with two isoprene units, C 10 , sesquiterpenes C 15 — three isoprene units, diterpenes C 20 — four isoprene units, triterpenes C 30 — six units, tetraterpenes C 40 — eight units, and polyterpenes , which comprise more isoprene units. Isopentenyl diphosphate Dimethylallyl diphosphate All isoprenoids are synthesized from acetyl-CoA by way of an important intermediate isopentenyl diphosphate and its isomer dimethylallyl diphosphate.
Dimethylallyl diphosphate and isopentenyl diphosphate are basal units for polymerization.