Prostaglandin A2 (BioDeep_00000006014)

 

Secondary id: BioDeep_00000171539, BioDeep_00000227111, BioDeep_00000629503

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


(5Z)-7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid

化学式: C20H30O4 (334.214398)
中文名称: 前列腺素 A2
谱图信息: 最多检出来源 Viridiplantae(plant) 0.07%

分子结构信息

SMILES: CCCCCC(C=CC1C=CC(=O)C1CC=CCCCC(=O)O)O
InChI: InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-12+/t16-,17-,18+/m0/s1

描述信息

Produced by the seminal vesicles, prostaglandins are a group of lipid compounds that are derived enzymatically from fatty acids. Technically hormones, the prostanoid class of fatty acid derivatives is a subclass of eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis through receptor-mediated G-protein linked signaling pathways. Prostaglandin A is a cyclopentenone and is an endogenous metabolite derived from arachidonic acid. It exhibits potent cellular anti-proliferative activity in vivo and in vitro. Excess PGA2 causes an accumulation in both S and G2/M, and a marked decrease in G1. There is also an increase in DNA content preceeding the G0/G1 peak (indicative of apoptotic body formation) mediated by changes in expression levels of Bax and Bcl-2.
Produced by the seminal vessicals: Prostaglandins are a group of lipid compounds that are derived enzymatically from fattyacids. Technically a hormone, the prostanoid class of fatty acid derivatives is a subclass of eicosanoids. Prostaglandin A is cyclopentenone and endogenous metabolite derived from arachidonic acid. Exhibits potent cellular anti-proliferative activity in vivo and in vitro. Excess PGA2 causes an accumulation in both S and G2/M, and a marked decrease in G1. As well there is an increase in DNA content preceeding the G0/G1 peak (indicative of apoptic body formation) mediated by changes in expression levels of Bax and Bcl-2.

同义名列表

24 个代谢物同义名

(5Z)-7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid; (Z)-7-((1R,2S)-2-((e)-(3S)-3-Hydroxyoct-1-enyl)-5-oxocyclopent-3-enyl)hept-5-enoic acid; 7-[2-(3-hydroxyoct-1-enyl)-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid; 7-[2-(3-Hydroxy-1-octenyl)-5-oxo-3-cyclopenten-1-yl]-5-heptenoic acid; 15Α-hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acid; (5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5, 10,13-triene-1-Oic acid; (5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5,10,13-trien-1-Oic acid; 15Α-hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylate; 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoic acid; 15Α-hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acid; 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoic acid; 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoate; 9-oxo-15S-hydroxy-prosta-5Z,10,13E-trien-1-oic acid; 15Α-hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoate; 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoate; 15(S)-Prostaglandin a2; (15S)-Prostaglandin a2; (+)-Prostaglandin a2; PROSTAGLANDIN A2; 5,6-cis-PGA2; NSC 165561; (15S)-PGA2; Medullin; PGA2



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

52 个相关的代谢反应过程信息。

Reactome(5)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

28 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Ai Lin Daphne Teh, Jaime Jacqueline Jayapalan, Mun Fai Loke, Azida Juana Wan Abdul Kadir, Visvaraja Subrayan. Identification of potential serum metabolic biomarkers for patient with keratoconus using untargeted metabolomics approach. Experimental eye research. 2021 10; 211(?):108734. doi: 10.1016/j.exer.2021.108734. [PMID: 34428458]
  • Lucila Ludmila Paula Gutierrez, Claudia Vieira Marques, Sofia Pizzato Scomazzon, Helena Trevisan Schroeder, João Roberto Fernandes, Juliane da Silva Rossato, Paulo Ivo Homem de Bittencourt. A-family anti-inflammatory cyclopentenone prostaglandins: A novel class of non-statin inhibitors of HMG-CoA reductase. Biochimie. 2021 Mar; 182(?):37-50. doi: 10.1016/j.biochi.2020.12.019. [PMID: 33412161]
  • Fabiano E Xavier, Javier Blanco-Rivero, Esther Sastre, Lina Badimón, Gloria Balfagón. Simultaneous inhibition of TXA(2) and PGI(2) synthesis increases NO release in mesenteric resistance arteries from cirrhotic rats. Clinical science (London, England : 1979). 2010 Jun; 119(7):283-92. doi: 10.1042/cs20090536. [PMID: 20459396]
  • Sun-Young Lee, Ji-Hyun Ahn, Kyoung Won Ko, Jaetaek Kim, Seong Whan Jeong, In-Kyung Kim, Jin Kim, Ho-Shik Kim. Prostaglandin A2 activates intrinsic apoptotic pathway by direct interaction with mitochondria in HL-60 cells. Prostaglandins & other lipid mediators. 2010 Feb; 91(1-2):30-7. doi: 10.1016/j.prostaglandins.2009.12.003. [PMID: 20044024]
  • Paulo I Homem de Bittencourt, Denise J Lagranha, Alexandre Maslinkiewicz, Sueli M Senna, Angela M V Tavares, Lisiane P Baldissera, Daiane R Janner, Joelso S Peralta, Patrícia M Bock, Lucila L P Gutierrez, Gustavo Scola, Thiago G Heck, Maurício S Krause, Lavínia A Cruz, Dulcinéia S P Abdalla, Cláudia J Lagranha, Thais Lima, Rui Curi. LipoCardium: endothelium-directed cyclopentenone prostaglandin-based liposome formulation that completely reverses atherosclerotic lesions. Atherosclerosis. 2007 Aug; 193(2):245-58. doi: 10.1016/j.atherosclerosis.2006.08.049. [PMID: 16996518]
  • Javier Gayarre, David Sánchez, Francisco J Sánchez-Gómez, María C Terrón, Oscar Llorca, Dolores Pérez-Sala. Addition of electrophilic lipids to actin alters filament structure. Biochemical and biophysical research communications. 2006 Nov; 349(4):1387-93. doi: 10.1016/j.bbrc.2006.09.005. [PMID: 16979589]
  • Oliver Schröder, Yulyana Yudina, Alan Sabirsh, Nadine Zahn, Jesper Z Haeggström, Jürgen Stein. 15-deoxy-Delta12,14-prostaglandin J2 inhibits the expression of microsomal prostaglandin E synthase type 2 in colon cancer cells. Journal of lipid research. 2006 May; 47(5):1071-80. doi: 10.1194/jlr.m600008-jlr200. [PMID: 16495511]
  • Angela Kolberg, Tatiana Gomes Rosa, Minéia Taíse Puhl, Gustavo Scola, Daiane da Rocha Janner, Alexandre Maslinkiewicz, Denise Jacques Lagranha, Thiago Gomes Heck, Rui Curi, Paulo Ivo Homem de Bittencourt. Low expression of MRP1/GS-X pump ATPase in lymphocytes of Walker 256 tumour-bearing rats is associated with cyclopentenone prostaglandin accumulation and cancer immunodeficiency. Cell biochemistry and function. 2006 Jan; 24(1):23-39. doi: 10.1002/cbf.1290. [PMID: 16170839]
  • Sonia Brault, Ana Katherine Martinez-Bermudez, Jackson Roberts, Qiao-Ling Cui, Gabriela Fragoso, Sandy Hemdan, Hsueh-Ning Liu, Fernand Gobeil, Christiane Quiniou, Elsa Kermorvant-Duchemin, Christian Lachance, Guillermina Almazan, Daya R Varma, Sylvain Chemtob. Cytotoxicity of the E(2)-isoprostane 15-E(2t)-IsoP on oligodendrocyte progenitors. Free radical biology & medicine. 2004 Aug; 37(3):358-66. doi: 10.1016/j.freeradbiomed.2004.05.007. [PMID: 15223069]
  • Ho-Shik Kim, Hyangshuk Rhim, Seong-Whan Jeong, Jin Woo Kim, In-Kyung Kim. Induction of apoptosis dependent on caspase activities and growth arrest in HL-60 cells by PGA2. Prostaglandins & other lipid mediators. 2002 Sep; 70(1-2):169-83. doi: 10.1016/s0090-6980(02)00064-3. [PMID: 12428687]
  • K Büyükgüzel, H Tunaz, S M Putnam, D Stanley. Prostaglandin biosynthesis by midgut tissue isolated from the tobacco hornworm, Manduca sexta. Insect biochemistry and molecular biology. 2002 Apr; 32(4):435-43. doi: 10.1016/s0965-1748(01)00121-7. [PMID: 11886778]
  • K Still, A Scutt. Stimulation of CFU-f formation by prostaglandin E2 is mediated in part by its degradation product, prostaglandin A2. Prostaglandins & other lipid mediators. 2001 May; 65(1):21-31. doi: 10.1016/s0090-6980(01)00117-4. [PMID: 11352224]
  • A M Joubert, A Panzer, F Joubert, M L Lottering, P C Bianchi, J C Seegers. Comparative study of the effects of polyunsaturated fatty acids and their metabolites on cell growth and tyrosine kinase activity in oesophageal carcinoma cells. Prostaglandins, leukotrienes, and essential fatty acids. 1999 Sep; 61(3):171-82. doi: 10.1054/plef.1999.0087. [PMID: 10582657]
  • Y Chen, J D Morrow, L J Roberts. Formation of reactive cyclopentenone compounds in vivo as products of the isoprostane pathway. The Journal of biological chemistry. 1999 Apr; 274(16):10863-8. doi: 10.1074/jbc.274.16.10863. [PMID: 10196163]
  • A Jawerbaum, V Novaro, A M Franchi, M Gimeno, E González. High glucose levels modulate eicosanoid production in uterine and placental tissue from non-insulin-dependent diabetic rats during late pregnancy. Prostaglandins, leukotrienes, and essential fatty acids. 1998 Jun; 58(6):389-93. doi: 10.1016/s0952-3278(98)90158-2. [PMID: 10189067]
  • R Evers, N H Cnubben, J Wijnholds, L van Deemter, P J van Bladeren, P Borst. Transport of glutathione prostaglandin A conjugates by the multidrug resistance protein 1. FEBS letters. 1997 Dec; 419(1):112-6. doi: 10.1016/s0014-5793(97)01442-7. [PMID: 9426231]
  • M Gorospe, X Wang, K Z Guyton, N J Holbrook. Protective role of p21(Waf1/Cip1) against prostaglandin A2-mediated apoptosis of human colorectal carcinoma cells. Molecular and cellular biology. 1996 Dec; 16(12):6654-60. doi: 10.1128/mcb.16.12.6654. [PMID: 8943319]
  • M Hitomi, J Shu, D Strom, S W Hiebert, M L Harter, D W Stacey. Prostaglandin A2 blocks the activation of G1 phase cyclin-dependent kinase without altering mitogen-activated protein kinase stimulation. The Journal of biological chemistry. 1996 Apr; 271(16):9376-83. doi: 10.1074/jbc.271.16.9376. [PMID: 8621603]
  • M Gorospe, Y Liu, Q Xu, F J Chrest, N J Holbrook. Inhibition of G1 cyclin-dependent kinase activity during growth arrest of human breast carcinoma cells by prostaglandin A2. Molecular and cellular biology. 1996 Mar; 16(3):762-70. doi: 10.1128/mcb.16.3.762. [PMID: 8622677]
  • M Gorospe, N J Holbrook. Role of p21 in prostaglandin A2-mediated cellular arrest and death. Cancer research. 1996 Feb; 56(3):475-9. doi: . [PMID: 8564956]
  • A Sawamura, E Kusunose, K Satouchi, M Kusunose. Catalytic properties of rabbit kidney fatty acid omega-hydroxylase cytochrome P-450ka2 (CYP4A7). Biochimica et biophysica acta. 1993 May; 1168(1):30-6. doi: . [PMID: 8504139]
  • E E Muirhead, B Brooks, L W Byers. Biologic differences between vasodilator prostaglandins and medullipin I. The American journal of the medical sciences. 1992 Feb; 303(2):86-9. doi: 10.1097/00000441-199202000-00004. [PMID: 1539615]
  • D Rubinger, H Wald, P Scherzer, M M Popovtzer. Renal sodium handling and stimulation of medullary Na-K-ATPase during blockade of prostaglandin synthesis. Prostaglandins. 1990 Feb; 39(2):179-94. doi: 10.1016/0090-6980(90)90074-6. [PMID: 2156324]
  • G Deliconstantinos, L Kopeikina, G Ramantanis. PGE2 and PGA2 affect the allosteric properties and the activities of calmodulin-dependent guanylate cyclase and Ca2+-stimulated ATPase of Walker-256 tumour microsomal membranes. Anticancer research. 1989 May; 9(3):fluorescence polarization. doi: . [PMID: 2569856]
  • K Ohno, T Sakai, M Fukushima, S Narumiya, M Fujiwara. Site and mechanism of growth inhibition by prostaglandins. IV. Effect of cyclopentenone prostaglandins on cell cycle progression of G1-enriched HeLa S3 cells. The Journal of pharmacology and experimental therapeutics. 1988 Apr; 245(1):294-8. doi: NULL. [PMID: 3361448]
  • Z Lahoua, M E Astruc, A Crastes de Paulet. Serum-induced arachidonic acid release and prostaglandin biosynthesis are potentiated by oxygenated sterols in NRK 49F cells. Biochimica et biophysica acta. 1988 Feb; 958(3):396-404. doi: 10.1016/0005-2760(88)90225-1. [PMID: 3124881]
  • G Deliconstantinos, L Kopeikina, G Ramantanis. Evoked effects of PGE2 and PGA2 on lipid fluidity and Ca2+-stimulated ATPase of Walker-256 tumor microsomal membranes. Annals of the New York Academy of Sciences. 1988; 551(?):245-8. doi: 10.1111/j.1749-6632.1988.tb22342.x. [PMID: 2977534]
  • N A Wales. Hormone studies in Myxine glutinosa: effects of the eicosanoids arachidonic acid, prostaglandin E1, E2, A2, F2 alpha, thromboxane B2 and of indomethacin on plasma cortisol, blood pressure, urine flow and electrolyte balance. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology. 1988; 158(5):621-6. doi: 10.1007/bf00692571. [PMID: 3249024]
  • A Fine, R H Goldstein. The effect of PGE2 on the activation of quiescent lung fibroblasts. Prostaglandins. 1987 Jun; 33(6):903-13. doi: 10.1016/0090-6980(87)90117-1. [PMID: 2823317]
  • E Li. [Pathogenesis of schizophrenia: assay of PG and cAMP in the CSF and plasma in 25 cases]. Zhonghua shen jing jing shen ke za zhi = Chinese journal of neurology and psychiatry. 1987 Apr; 20(2):81-3. doi: NULL. [PMID: 3040348]
  • T Mitsuma, T Nogimori, De Heng Sun, M Chaya. Effect of prostaglandin A1 and A2 on thyrotropin secretion in rats. Endocrinologia experimentalis. 1986 Dec; 20(4):371-7. doi: . [PMID: 3492364]
  • K Ohno, M Fujiwara, M Fukushima, S Narumiya. Metabolic dehydration of prostaglandin E2 and cellular uptake of the dehydration product: correlation with prostaglandin E2-induced growth inhibition. Biochemical and biophysical research communications. 1986 Sep; 139(2):808-15. doi: 10.1016/s0006-291x(86)80062-6. [PMID: 3464277]
  • N A Wales, T Gaunt. Hemodynamic, renal, and steroidogenic actions of prostaglandins E1, E2, A2, and F2 alpha in European eels. General and comparative endocrinology. 1986 May; 62(2):327-34. doi: 10.1016/0016-6480(86)90123-1. [PMID: 3465668]
  • R O Banks, E D Jacobson. Renal vasodilation with ureteral occlusion and prostaglandins: attenuation by histamine H1 antagonists. The American journal of physiology. 1985 Dec; 249(6 Pt 2):F851-7. doi: 10.1152/ajprenal.1985.249.6.f851. [PMID: 2866716]
  • D P Mikhailidis, M A Barradas, A Maris, J Y Jeremy, P Dandona. Fibrinogen mediated activation of platelet aggregation and thromboxane A2 release: pathological implications in vascular disease. Journal of clinical pathology. 1985 Oct; 38(10):1166-71. doi: 10.1136/jcp.38.10.1166. [PMID: 3902901]
  • R Matsukawa, M Hayakawa, M Tanaka, H Takiguchi. Prostaglandin A2 receptor in rat intestinal basolateral plasma membranes. General pharmacology. 1985; 16(2):121-4. doi: 10.1016/0306-3623(85)90047-3. [PMID: 2987080]
  • S C Chen. [A study on the relationship between cyanotic tongue and prostaglandins]. Zhong xi yi jie he za zhi = Chinese journal of modern developments in traditional medicine. 1984 Apr; 4(4):216-7. doi: ". [PMID: 6235964]
  • K Matsumoto, K Saito, H Fukuda. Centrally specific and GABA-insensitive inhibition of benzodiazepine binding by prostaglandins (A1, A2 and B2). Journal of pharmacobio-dynamics. 1983 Oct; 6(10):784-6. doi: 10.1248/bpb1978.6.784. [PMID: 6319659]
  • P Christensen, N H Holstein-Rathlou. Interaction between prostaglandins of the E-type with a urinary component from halothane anesthetized rats. Prostaglandins. 1981 Dec; 22(6):893-902. doi: 10.1016/0090-6980(81)90019-8. [PMID: 6950460]
  • R Matsukawa, N Terao, M Hayakawa, H Takiguchi. Effects of prostaglandin A2 on Na+, K+-ATPase activity in basolateral plasma membrane of rat intestine in vitro. Biochemical and biophysical research communications. 1981 Aug; 101(4):1305-10. doi: 10.1016/0006-291x(81)91589-8. [PMID: 6272780]
  • J B LEE, B G COVINO, B H TAKMAN, E R SMITH. RENOMEDULLARY VASODEPRESSOR SUBSTANCE, MEDULLIN: ISOLATION, CHEMICAL CHARACTERIZATION AND PHYSIOLOGICAL PROPERTIES. Circulation research. 1965 Jul; 17(?):57-77. doi: 10.1161/01.res.17.1.57. [PMID: 14302553]