Prostaglandin A1 (BioDeep_00000001681)

 

Secondary id: BioDeep_00000017896, BioDeep_00000403253

human metabolite Endogenous blood metabolite


代谢物信息卡片


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

化学式: C20H32O4 (336.2300472)
中文名称: 前列腺素A1
谱图信息: 最多检出来源 Viridiplantae(plant) 0.05%

Reviewed

Last reviewed on 2024-08-13.

Cite this Page

Prostaglandin A1. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/prostaglandin_a1 (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000001681). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCC(C=CC1C=CC(=O)C1CCCCCCC(=O)O)O
InChI: InChI=1S/C20H32O4/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/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1

描述信息

Prostaglandin A1 (PGA1, a prostaglandin characterized by a cyclopentenone structure) has a fundamental structure common to punaglandin and clavulone, the antitumor eicosanoids discovered in marine organisms such as corals. It is well established that PGA1, which exert potent antiviral activity in several DNA and RNA virus models, induce heat shock protein (hsp)70 syntheses through cycloheximide sensitive activation of heat shock transcription factor. Antitumor prostaglandins are actively incorporated through cell membrane and control gene expression. P53 (protein 53, is a transcription factor that regulates the cell cycle and functions as a tumor suppressor) independent expression of p21 (also known as cyclin-dependent kinase inhibitor 1A or CDKN1A, is a human gene on chromosome 6 (location 6p21.2), that encodes a cyclin-dependent kinase) and gadd 45 (growth arrest and DNA-damage-inducible, alpha 45, a major breast cancer (BRCA1) target is the DNA damage-responsive gene GADD45) activation of peroxisome proliferative activated receptor gamma (PPARgamma) are involved in antitumor mechanism of these prostaglandins. At the low concentration, these prostaglandins exhibit physiological or pathological activity such as osteoblast calcification, promotion of colon cancer cell proliferation. One of the mechanisms of anti-cancer activity of prostaglandins, has been believed to be that these prostaglandins might have p53 like effect in cells lacking p53. (PMID: 7988663, 11104898)Prostaglandins are 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 signalling pathways.
Prostaglandin A1 (PGA1, a prostaglandin characterized by a cyclopentenone structure) has a fundamental structure common to punaglandin and clavulone, the antitumor eicosanoids discovered in marine organisms such as corals. It is well established that PGA1, which exert potent antiviral activity in several DNA and RNA virus models, induce heat shock protein (hsp)70 syntheses through cycloheximide sensitive activation of heat shock transcription factor. Antitumor prostaglandins are actively incorporated through cell membrane and control gene expression. P53 (protein 53, is a transcription factor that regulates the cell cycle and functions as a tumor suppressor) independent expression of p21 (also known as cyclin-dependent kinase inhibitor 1A or CDKN1A, is a human gene on chromosome 6 (location 6p21.2), that encodes a cyclin-dependent kinase) and gadd 45 (growth arrest and DNA-damage-inducible, alpha 45, a major breast cancer (BRCA1) target is the DNA damage-responsive gene GADD45) activation of peroxisome proliferative activated receptor gamma (PPARgamma) are involved in antitumor mechanism of these prostaglandins. At the low concentration, these prostaglandins exhibit physiological or pathological activity such as osteoblast calcification, promotion of colon cancer cell proliferation. One of the mechanisms of anti-cancer activity of prostaglandins, has been believed to be that these prostaglandins might have p53 like effect in cells lacking p53. (PMID: 7988663, 11104898)
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents

同义名列表

23 个代谢物同义名

7-[(1R,2S)-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl]heptanoic acid; 2-(3-Hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoic acid; 2-(3-Hydroxy-1-octenyl)-5-oxo-3-cyclopentene-1-heptanoic acid; 2-(3-Hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoate; 2-(3-Hydroxy-1-octenyl)-5-oxo-3-cyclopentene-1-heptanoate; (13E,15S)-15-Hydroxy-9-oxo-prosta-10,13-dien-1-Oic acid; (13E)-(15S)-15-Hydroxy-9-oxoprosta-10,13-dienoic acid; (13E,15S)-15-Hydroxy-9-oxo-prosta-10,13-dien-1-Oate; (13E)-(15S)-15-Hydroxy-9-oxoprosta-10,13-dienoate; Prostaglandin a1, (8beta,12alpha,13E,15S)-isomer; 9-oxo-15S-hydroxy-10Z,13E-prostadienoic acid; 15a-Hydroxy-9-ketoprosta-10,13-dienoic acid; 15a-Hydroxy-9-oxo-10,13E-prostadienoic acid; 15-Hydroxy-9-oxoprosta-10,13-dienoic acid; 15a-Hydroxy-9-ketoprosta-10,13-dienoate; Prostaglandin a1, (13E,15R)-(+-)-isomer; 15a-Hydroxy-9-oxo-10,13E-prostadienoate; Prostaglandin a1, (13E,15S)-(+-)-isomer; 15-Hydroxy-9-oxoprosta-10,13-dienoate; Prostaglandin a1, (13E,15R)-isomer; Prostaglandin e1-217; PROSTAGLANDIN A1; PGA1



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 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

  • Qinglong Li, Xiaomin Wang, Yang Lei, Yanling Wang, Bilang Li, Xiayan Liu, Lijun An, Fei Yu, Yafei Qi. Chloroplast envelope ATPase PGA1/AtFtsH12 is required for chloroplast protein accumulation and cytosol-chloroplast protein homeostasis in Arabidopsis. The Journal of biological chemistry. 2022 10; 298(10):102489. doi: 10.1016/j.jbc.2022.102489. [PMID: 36113581]
  • Y Sajiki, S Konnai, Y Ikenaka, T Okagawa, N Maekawa, C Logullo, I da Silva Vaz, S Murata, K Ohashi. Prostaglandin-related immune suppression in cattle. Veterinary immunology and immunopathology. 2021 Jun; 236(?):110238. doi: 10.1016/j.vetimm.2021.110238. [PMID: 33857743]
  • Guo-Biao Xu, Liu-Qing Yang, Pei-Pei Guan, Zhan-You Wang, Pu Wang. Prostaglandin A1 Inhibits the Cognitive Decline of APP/PS1 Transgenic Mice via PPARγ/ABCA1-dependent Cholesterol Efflux Mechanisms. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics. 2019 04; 16(2):505-522. doi: 10.1007/s13311-018-00704-1. [PMID: 30627958]
  • Lúcio Ayres Caldas, Tânia Rosária Pereira Freitas, Renata Campos Azevedo, Wanderley de Souza. Prostaglandin A1 inhibits the replication of bovine viral diarrhea virus. Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology]. 2018 Oct; 49(4):785-789. doi: 10.1016/j.bjm.2017.12.010. [PMID: 29544983]
  • Simone Findling, Henrik U Stotz, Maria Zoeller, Markus Krischke, Mark Zander, Christiane Gatz, Susanne Berger, Martin J Mueller. TGA2 signaling in response to reactive electrophile species is not dependent on cysteine modification of TGA2. PloS one. 2018; 13(4):e0195398. doi: 10.1371/journal.pone.0195398. [PMID: 29608605]
  • Beatriz Díez-Dacal, Francisco J Sánchez-Gómez, Pedro A Sánchez-Murcia, Ivana Milackova, Tahl Zimmerman, Jana Ballekova, Elena García-Martín, José A G Agúndez, Severine Gharbi, Federico Gago, Milan Stefek, Dolores Pérez-Sala. Molecular Interactions and Implications of Aldose Reductase Inhibition by PGA1 and Clinically Used Prostaglandins. Molecular pharmacology. 2016 Jan; 89(1):42-52. doi: 10.1124/mol.115.100693. [PMID: 26487510]
  • Stefania Carta, Simone La Frazia, Isabella Donatelli, Simona Puzelli, Antonio Rossi, M Gabriella Santoro. Prostaglandin A1 inhibits avian influenza virus replication at a postentry level: Effect on virus protein synthesis and NF-κB activity. Prostaglandins, leukotrienes, and essential fatty acids. 2014 Dec; 91(6):311-23. doi: 10.1016/j.plefa.2014.07.009. [PMID: 25151089]
  • Henrik U Stotz, Stefan Mueller, Maria Zoeller, Martin J Mueller, Susanne Berger. TGA transcription factors and jasmonate-independent COI1 signalling regulate specific plant responses to reactive oxylipins. Journal of experimental botany. 2013 Feb; 64(4):963-75. doi: 10.1093/jxb/ers389. [PMID: 23349138]
  • Joseph Antoun, Sophie Goulitquer, Yolande Amet, Yvonne Dreano, Jean-Pierre Salaun, Laurent Corcos, Emmanuelle Plée-Gautier. CYP4F3B is induced by PGA1 in human liver cells: a regulation of the 20-HETE synthesis. Journal of lipid research. 2008 Oct; 49(10):2135-41. doi: 10.1194/jlr.m800043-jlr200. [PMID: 18566475]
  • David W Stanley, Cynthia Goodman, Shiheng An, Arthur McIntosh, Qisheng Song. Prostaglandins A1 and E1 influence gene expression in an established insect cell line (BCIRL-HzAM1 cells). Insect biochemistry and molecular biology. 2008 Mar; 38(3):275-84. doi: 10.1016/j.ibmb.2007.11.004. [PMID: 18252242]
  • Woo Jae Kim, Joon Hyun Kim, Sung Key Jang. Anti-inflammatory lipid mediator 15d-PGJ2 inhibits translation through inactivation of eIF4A. The EMBO journal. 2007 Dec; 26(24):5020-32. doi: 10.1038/sj.emboj.7601920. [PMID: 18034160]
  • 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]
  • Etsuko Hirayama. [Relationship of HSP70 to temperature-dependency of influenza viral infection]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2004 Jul; 124(7):437-42. doi: 10.1248/yakushi.124.437. [PMID: 15235227]
  • Carla Amici, Giuseppe Belardo, Carmela Rozera, Daniela Bernasconi, M Gabriella Santoro. Inhibition of herpesvirus-induced HIV-1 replication by cyclopentenone prostaglandins: role of IkappaB kinase (IKK). AIDS (London, England). 2004 Jun; 18(9):1271-80. doi: 10.1097/00002030-200406180-00005. [PMID: 15362659]
  • Etsuko Hirayama, Hiromitsu Atagi, Akihiro Hiraki, Jeman Kim. Heat shock protein 70 is related to thermal inhibition of nuclear export of the influenza virus ribonucleoprotein complex. Journal of virology. 2004 Feb; 78(3):1263-70. doi: 10.1128/jvi.78.3.1263-1270.2004. [PMID: 14722281]
  • Philip J Moos, Kornelia Edes, Pamela Cassidy, Edmond Massuda, F A Fitzpatrick. Electrophilic prostaglandins and lipid aldehydes repress redox-sensitive transcription factors p53 and hypoxia-inducible factor by impairing the selenoprotein thioredoxin reductase. The Journal of biological chemistry. 2003 Jan; 278(2):745-50. doi: 10.1074/jbc.m211134200. [PMID: 12424231]
  • Paul F Glidden, David B Goldberg, Charles M Heldebrant. A chromatographic method for the quantification of prostaglandin E(1) and prostaglandin A(1) encapsulated in an intravenous lipid formulation. Journal of pharmaceutical and biomedical analysis. 2002 Apr; 28(2):295-302. doi: 10.1016/s0731-7085(01)00634-3. [PMID: 11929672]
  • M Mangelus, R Galron, Z Naor, M Sokolovsky. Involvement of nuclear factor-kappaB in endothelin-A-receptor-induced proliferation and inhibition of apoptosis. Cellular and molecular neurobiology. 2001 Dec; 21(6):657-74. doi: 10.1023/a:1015195803445. [PMID: 12043840]
  • S Fukushima, S Kishimoto, Y Takeuchi, M Fukushima. Preparation and evaluation of o/w type emulsions containing antitumor prostaglandin. Advanced drug delivery reviews. 2000 Dec; 45(1):65-75. doi: 10.1016/s0169-409x(00)00101-0. [PMID: 11104898]
  • Y G Assaraf, E E Sierra, S Babani, I D Goldman. Inhibitory effects of prostaglandin A1 on membrane transport of folates mediated by both the reduced folate carrier and ATP-driven exporters. Biochemical pharmacology. 1999 Oct; 58(8):1321-7. doi: 10.1016/s0006-2952(99)00227-0. [PMID: 10487535]
  • H Sasaki, S Niimi, M Akiyama, T Tanaka, A Hazato, S Kurozumi, S Fukushima, M Fukushima. Antitumor activity of 13,14-dihydro-15-deoxy-delta7-prostaglandin-A1-methyl ester integrated into lipid microspheres against human ovarian carcinoma cells resistant to cisplatin in vivo. Cancer research. 1999 Aug; 59(16):3919-22. doi: . [PMID: 10463583]
  • K N Prasad, F G La Rosa, J E Prasad. Prostaglandins act as neurotoxin for differentiated neuroblastoma cells in culture and increase levels of ubiquitin and beta-amyloid. In vitro cellular & developmental biology. Animal. 1998 Mar; 34(3):265-74. doi: 10.1007/s11626-998-0133-7. [PMID: 9557945]
  • 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]
  • S Itoh, R Lu, Y Bao, J D Morrow, L J Roberts, V L Schuster. Structural determinants of substrates for the prostaglandin transporter PGT. Molecular pharmacology. 1996 Oct; 50(4):738-42. doi: NULL. [PMID: 8863817]
  • C Amici, C Giorgi, A Rossi, M G Santoro. Selective inhibition of virus protein synthesis by prostaglandin A1: a translational block associated with HSP70 synthesis. Journal of virology. 1994 Nov; 68(11):6890-9. doi: 10.1128/jvi.68.11.6890-6899.1994. [PMID: 7933069]
  • 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]
  • C Amici, M G Santoro. Suppression of virus replication by prostaglandin A is associated with heat shock protein synthesis. The Journal of general virology. 1991 Aug; 72 ( Pt 8)(?):1877-85. doi: 10.1099/0022-1317-72-8-1877. [PMID: 1651981]
  • G A Lopez, N Lopez, S Brazal, M Natividad. Renin release responses to in vitro prostaglandin challenge in the summer-active ground squirrel, Spermophilus lateralis. Comparative biochemistry and physiology. A, Comparative physiology. 1989; 94(4):575-81. doi: 10.1016/0300-9629(89)90596-3. [PMID: 2575941]
  • J Deutsch, D Rachmilewitz. Investigation of field desorption mass spectral behaviour of prostaglandins for their determination in biological fluids. Biomedical & environmental mass spectrometry. 1988 Oct; 16(1-12):427-30. doi: 10.1002/bms.1200160184. [PMID: 3242699]
  • R Roy, S Karanth, A Dutt, H S Juneja. Involvement of prostaglandin A1 in interrupting early pregnancy in Syrian golden hamsters. Advances in contraception : the official journal of the Society for the Advancement of Contraception. 1987 Dec; 3(4):341-8. doi: 10.1007/bf01849292. [PMID: 3128059]
  • N Chegini, A R Safa. Morphological alterations induced by prostaglandins E1, F2 alpha and A1 in MDA-MB-231 and MCF-7 human breast cancer cell lines. Cancer letters. 1987 Oct; 37(2):189-97. doi: 10.1016/0304-3835(87)90162-5. [PMID: 2824026]
  • V I Kulikov, S M Levachev. [Nonenzymatic incorporation of prostaglandin A1 into phospholipids in rat liver microsomes]. Biokhimiia (Moscow, Russia). 1987 Jul; 52(7):1154-61. doi: ". [PMID: 3663753]
  • 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]
  • J Goto, H Araki, S Otomo, H Aihara. A comparison of the effect of Lipo PGE1 and other related compounds on experimental peripheral arterial occlusive disease in rats. Drugs under experimental and clinical research. 1986; 12(11):917-21. doi: ". [PMID: 3816509]
  • Y N Huo, Z G Wang, Y C Jin. [Inhibitory effects of non-steroidal anti-inflammatory drugs on the binding of prostaglandins to human serum albumin]. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1985 Sep; 6(3):178-80. doi: NULL. [PMID: 2943121]
  • J D Watkins, J Jarabak. The effect of NaCl intake on 9-ketoprostaglandin reductase activity in the rabbit kidney. Prostaglandins. 1985 Aug; 30(2):335-49. doi: 10.1016/0090-6980(85)90196-0. [PMID: 3901124]
  • L E Heasley, J Azari, L L Brunton. Export of cyclic AMP from avian red cells. Independence from major membrane transporters and specific inhibition by prostaglandin A. Molecular pharmacology. 1985 Jan; 27(1):60-5. doi: NULL. [PMID: 2981402]
  • J Booyens, P Engelbrecht, S le Roux, C C Louwrens, C F Van der Merwe, I E Katzeff. Some effects of the essential fatty acids linoleic acid and alpha-linolenic acid and of their metabolites gamma-linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, and of prostaglandins A1 and E1 on the proliferation of human osteogenic sarcoma cells in culture. Prostaglandins, leukotrienes, and medicine. 1984 Jul; 15(1):15-33. doi: 10.1016/0262-1746(84)90053-2. [PMID: 6089235]
  • K R Krijgsheld, T E Gram. Selective induction of renal microsomal cytochrome P-450-linked monooxygenases by 1,1-dichloroethylene in mice. Biochemical pharmacology. 1984 Jun; 33(12):1951-6. doi: 10.1016/0006-2952(84)90554-9. [PMID: 6610421]
  • E Kusunose, M Kaku, K Ichihara, S Yamamoto, I Yano, M Kusunose. Hydroxylation of prostaglandin A1 by the microsomes of rabbit intestinal mucosa. Journal of biochemistry. 1984 Jun; 95(6):1733-9. doi: 10.1093/oxfordjournals.jbchem.a134787. [PMID: 6469945]
  • R Jouve, P H Rolland, C Delboy, C Mercier. Thromboxane B2, 6-keto-PGF1 alpha, PGE2, PGF2 alpha, and PGA1 plasma levels in arteriosclerosis obliterans: relationship to clinical manifestations, risk factors, and arterial pathoanatomy. American heart journal. 1984 Jan; 107(1):45-52. doi: 10.1016/0002-8703(84)90132-7. [PMID: 6581715]
  • 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]
  • M G Santoro, A Benedetto, S Zaniratti, E Garaci, B M Jaffe. The relationship between prostaglandins and virus replication: endogenous prostaglandin synthesis during infection and the effect of exogenous PGA on virus production in different cell lines and in persistently infected cells. Prostaglandins. 1983 Mar; 25(3):353-64. doi: 10.1016/0090-6980(83)90038-2. [PMID: 6191363]
  • W D McCumbee, J M Harrelson, H E Lebovitz. Hormonal and metabolic regulation of human chondrosarcoma in vitro. Cancer research. 1983 Feb; 43(2):513-6. doi: NULL. [PMID: 6293699]
  • A Kondo, M Kobayashi, T Takita, H Narita. Effect of prostaglandin on urethral resistance and micturition. Urological research. 1983; 11(1):19-22. doi: 10.1007/bf00272704. [PMID: 6574652]
  • M G Santoro, B M Jaffe, G Elia, A Benedetto. Prostaglandin A1 induces the synthesis of a new protein in cultured AGMK cells. Biochemical and biophysical research communications. 1982 Aug; 107(4):1179-84. doi: 10.1016/s0006-291x(82)80121-6. [PMID: 6291523]
  • S A Badzhinian. [Prostaglandin regulation of ionic conductivity of model membranes]. Biofizika. 1982 Mar; 27(2):277-9. doi: ". [PMID: 7041991]
  • H H Neumayer, K Wagner, G Schultze, P Laubner, M K Maiga, M Molzahn. Influence of prostaglandins A1, E1, E2, and F2 alpha on renal blood flow and plasma renin activity. Investigations in chronically instrumented conscious dogs. Renal physiology. 1982; 5(2):57-67. doi: . [PMID: 7041212]