プロスタノイド
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/01/06 22:32:44」(JST)
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Prostanoids are 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
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 appear to be stimulated by certain cytokines, e.g., interleukin-1.[1]
See also
- Essential fatty acid
- Isoprostane
Autacoids, unsaturated fatty acids: Eicosanoids
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Precursor |
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Prostanoids |
Prostaglandins (PG) and
analogues |
Precursor |
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Active |
D/J |
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E/F |
- E2 (Dinoprostone): Enprostil
- Sulprostone
- E1 (Alprostadil): Misoprostol
- Gemeprost
- F2α (Dinoprost): Bimatoprost
- Carboprost
- Latanoprost
- Tafluprost
- Travoprost
- Unoprostone
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I |
- I2 (Prostacyclin/Epoprostenol): Beraprost
- Iloprost
- Treprostinil
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Thromboxanes (TX) |
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Leukotrienes (LT) |
Precursor |
- Arachidonic acid 5-hydroperoxide
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Initial |
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SRS-A |
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Nonclassic |
- Lipoxins (A4, B4)
- Virodhamine
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By function |
- vasoconstriction
- vasodilation
- platelets: induce
- inhibit
- leukocytes: induce
- inhibit
- labor stimulation:
- PGE2 (Dinoprostone)
- PGF2α (Dinoprost)
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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- biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- amino acids / intermediates
- tetrapyrroles / intermediates
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References
- ^ University of Kansas Medical Center (2004). "Eicosanoids and Inflammation" (PDF). http://classes.kumc.edu/som/bioc801/small_group/eicosanoids/eicosanoids-2004.pdf. Retrieved 2007-01-05.[dead link]
UpToDate Contents
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English Journal
- Professional phagocytic granulocyte-derived PGD2 regulates the resolution of inflammation in fish.
- Gómez-Abellán V1, Montero J1, López-Muñoz A1, Figueras A2, Arizcun M3, Mulero V1, Sepulcre MP4.
- Developmental and comparative immunology.Dev Comp Immunol.2015 Oct;52(2):182-91. doi: 10.1016/j.dci.2015.04.017. Epub 2015 May 28.
- Prostaglandins (PGs) play a key role in the development on the immune response through the regulation of both pro- and anti-inflammatory processes. PGD2 can be either pro- or anti-inflammatory depending on the inflammatory milieu. Prostaglandin D synthase (PGDS) is the enzyme responsible for the con
- PMID 26027798
- New yeast-based approaches in production of palmitoleic acid.
- Kolouchová I1, Sigler K2, Schreiberová O3, Masák J3, Řezanka T4.
- Bioresource technology.Bioresour Technol.2015 Sep;192:726-34. doi: 10.1016/j.biortech.2015.06.048. Epub 2015 Jun 16.
- Palmitoleic acid is found in certain dairy products and has broad applications in medicine and cosmetics. We tried to find a suitable producer of this acid among traditional biotechnological yeast species (Kluyveromyces polysporus, Torulaspora delbrueckii, Saccharomyces cerevisiae) characterized by
- PMID 26101962
- Des-aspartate-angiotensin I, a novel angiotensin AT1 receptor drug.
- Sim MK1.
- European journal of pharmacology.Eur J Pharmacol.2015 Aug 5;760:36-41. doi: 10.1016/j.ejphar.2015.04.004. Epub 2015 Apr 17.
- The review describes DAA-I (des-aspartate-angiotensin-I) as a prototype of a novel class of drugs that acts as agonists on the angiotensin AT1 receptor or ARAs (angiotensin receptor agonists). DAA-I is a component of the renin angiotensin system. Earlier studies showed that it was rapidly metabolize
- PMID 25891368
Japanese Journal
- Roles of prostaglandin receptors in female reproduction (JB Special Reviews : Recent Progress in Lipid Mediators)
- Sugimoto Yukihiko,Inazumi Tomoaki,Tsuchiya Soken
- The journal of biochemistry 157(2), 73-80, 2015-02
- NAID 40020353006
- ,
- Allergology International 64(1), 11-16, 2015
- … It has been demonstrated that each prostanoid receptor has multiple functions and that the effect of receptor stimulation can vary depending on context; … The balance between the production of each prostanoid and the expression of its receptors has been shown to be important for maintaining homeostasis but also involved in the development of various pathological conditions such as allergy. …
- NAID 130004873121
- 遠山 千春
- 日本衛生学雑誌 69(1), 1-7, 2014
- … As the molecular basis of the tissue-specific endpoints of dioxin toxicity, dysregulation of AhR downstream pathways, such as signaling of prostanoid synthesis, Wnt/β-catenin signaling, and signaling by receptors for inflammatory cytokines, are discussed. …
- NAID 130003394509
Related Links
- A. Prostanoid Receptors as Rhodopsin-Type Receptors The structure of the human TxA 2 receptor is shown in Figure 2 as a representative of the prostanoid receptors. It is a protein composed of 343 amino acids and is a G protein ...
- Prostanoidとは?goo Wikipedia (ウィキペディア) 。出典:Wikipedia(ウィキペディア)フリー百科事典。 Prostanoidとは - goo Wikipedia (ウィキペディア) gooトップ サイトマップ スタートページに設定 RSS ヘルプ メニューへスキップ 本文へ ...
Related Pictures
★リンクテーブル★
[★]
- 英
- arachidonic acid, arachidonate
- 同
- 5,8,11,14-エイコサテトラエン酸 5,8,11,14-eicosatetraenoic acid、5,8,11,14-イコサテトラエン酸 5,8,11,14-icosatetraenoic acid
- 関
- 脂肪酸、必須脂肪酸
- 炭素数が20で二重結合を4つ有する
- CH3(CH2)4(CH=CHCH2)4(CH2)2COOH
- リノール酸から合成される
- アラキドン酸は細胞膜の中にホスファチジルイノシトールのC2エステルまたは他のリン脂質のエステルとして蓄えられる (FB.159)
- ホスホリパーゼA2の作用でアラキドン酸として遊離
機能
- ロイコトリエンやプロスタグランジンの前駆体
- prostanoid: cyclooxygenase pathway
- leukotriene:lipoxygenase pathway
- epoxide:cytochrome P-450 epoxygenase pathway
代謝
[★]
- 英
- prostanoid
- 関
- プロスタグランジン