Atractyloside (BioDeep_00000015335)

   

PANOMIX_OTCML-2023


代谢物信息卡片


dipotassium;[2-[[(1R,9R)-5-carboxy-15-hydroxy-9-methyl-14-methylidene-7-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]oxy]-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-5-sulonatooxyoxan-4-yl] sulate

化学式: C30H44K2O16S2 (802.1345)
中文名称: 苍术苷钾盐
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 82.35%

分子结构信息

SMILES: CC(C)CC(=O)OC1C(C(C(OC1OC2CC(C3CCC45CC(CCC4C3(C2)C)C(=C)C5O)C(=O)O)CO)OS(=O)(=O)[O-])OS(=O)(=O)[O-].[K+].[K+]
InChI: /q

描述信息

D004791 - Enzyme Inhibitors
Atractyloside (potassium salt) is a member of pyridines.
A glycoside of a kaurene type diterpene that is found in some plants including Atractylis gummifera (ATRACTYLIS); COFFEE; XANTHIUM, and CALLILEPIS. Toxicity is due to inhibition of ADENINE NUCLEOTIDE TRANSLOCASE.
Atractyloside potassium salt is a toxic diterpenoid glycoside that can be isolated from the fruits of Xanthium sibiricum. Atractyloside potassium salt is a powerful and specific inhibitor of mitochondrial ADP/ATP transport. Atractyloside potassium salt inhibits chloride channels from mitochondrial membranes of rat heart[1][2][3].
Atractyloside potassium salt is a toxic diterpenoid glycoside that can be isolated from the fruits of Xanthium sibiricum. Atractyloside potassium salt is a powerful and specific inhibitor of mitochondrial ADP/ATP transport. Atractyloside potassium salt inhibits chloride channels from mitochondrial membranes of rat heart[1][2][3].

同义名列表

8 个代谢物同义名

Atractyloside; dipotassium;[2-[[(1R,9R)-5-carboxy-15-hydroxy-9-methyl-14-methylidene-7-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]oxy]-6-(hydroxymethyl)-3-(3-methylbutanoyloxy)-5-sulonatooxyoxan-4-yl] sulate; Atractyloside (potassium salt); Atractyloside potassium salt; Acid, Atractylic; Atractylic Acid; Atractylate; Atractyloside



数据库引用编号

14 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)

1 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。

亚细胞结构定位 关联基因列表


文献列表

  • Andrzej M Woyda-Ploszczyca. Direct and indirect targets of carboxyatractyloside, including overlooked toxicity toward nucleoside diphosphate kinase (NDPK) and mitochondrial H+ leak. Pharmaceutical biology. 2023 Dec; 61(1):372-390. doi: 10.1080/13880209.2023.2168704. [PMID: 36799406]
  • Jing Xu, Chunlian Liu, Kun Shi, Xiongjie Sun, Chengcheng Song, Kang Xu, Yanju Liu. Atractyloside-A ameliorates spleen deficiency diarrhea by interfering with TLR4/MyD88/NF-κB signaling activation and regulating intestinal flora homeostasis. International immunopharmacology. 2022 Jun; 107(?):108679. doi: 10.1016/j.intimp.2022.108679. [PMID: 35279514]
  • De-Ling Wu, Tong-Sheng Wang, Hong-Juan Liu, Wei Zhang, Xiao-Hui Tong, Dai-Yin Peng, Ling-Yi Kong. Study on the mechanism of Wuzi-Yanzong-Wan-medicated serum interfering with the mitochondrial permeability transition pore in the GC-2 cell induced by atractyloside. Chinese journal of natural medicines. 2022 Apr; 20(4):282-289. doi: 10.1016/s1875-5364(22)60153-5. [PMID: 35487598]
  • Hailong Li, Xiaodong Shi, Hua Jiang, Junren Kang, Miao Yu, Qifei Li, Kang Yu, Zhengju Chen, Hui Pan, Wei Chen. CMap analysis identifies Atractyloside as a potential drug candidate for type 2 diabetes based on integration of metabolomics and transcriptomics. Journal of cellular and molecular medicine. 2020 07; 24(13):7417-7426. doi: 10.1111/jcmm.15357. [PMID: 32469143]
  • Hong Pan, Feng Yang, Daiyuan Xiang, Fuguo Shi. Simultaneous quantification of atractyloside and carboxyatractyloside in rat plasma by LC-MS/MS: Application to a pharmacokinetic study after oral administration of Xanthii Fructus extract. Journal of separation science. 2020 Feb; 43(3):590-597. doi: 10.1002/jssc.201900888. [PMID: 31701660]
  • Britta Spanier, Roman Lang, Daniela Weber, Anica Lechner, Tizia Thoma, Marion Rothner, Katrin Petzold, Tatjana Lang, Anja Beusch, Markus Bösl, Verena Schlagbauer, Hannelore Daniel, Thomas Hofmann. Bioavailability and Biological Effects of 2- O-β-d-Glucopyranosyl-carboxyatractyligenin from Green Coffee in Caenorhabditis elegans. Journal of agricultural and food chemistry. 2019 May; 67(17):4774-4781. doi: 10.1021/acs.jafc.8b06785. [PMID: 30963762]
  • Hai Jiang, Liu Yang, Xudong Xing, Meiling Yan, Xinyue Guo, Bingyou Yang, Qiu-Hong Wang, Hai-Xue Kuang. Chemometrics coupled with UPLC-MS/MS for simultaneous analysis of markers in the raw and processed Fructus Xanthii, and application to optimization of processing method by BBD design. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Apr; 57(?):191-202. doi: 10.1016/j.phymed.2018.12.020. [PMID: 30776590]
  • Huang Huang, Songqing Lai, Yong Luo, Qing Wan, Qicai Wu, Li Wan, Wanghong Qi, Jichun Liu. Nutritional Preconditioning of Apigenin Alleviates Myocardial Ischemia/Reperfusion Injury via the Mitochondrial Pathway Mediated by Notch1/Hes1. Oxidative medicine and cellular longevity. 2019; 2019(?):7973098. doi: 10.1155/2019/7973098. [PMID: 31015891]
  • Yangyang Xiao, Ling Lv, Ping Gou, Haihui Xie. Acyl atractyligenin and carboxyatractyligenin glycosides from Antennaria rosea subsp. confinis. Phytochemistry. 2019 Jan; 157(?):151-157. doi: 10.1016/j.phytochem.2018.10.018. [PMID: 30408728]
  • Shizhao Xu, Xiaojie Qi, Yuqiang Liu, Yuhan Liu, Xin Lv, Jianzhi Sun, Qian Cai. UPLC-MS/MS of Atractylenolide I, Atractylenolide II, Atractylenolide III, and Atractyloside A in Rat Plasma after Oral Administration of Raw and Wheat Bran-Processed Atractylodis Rhizoma. Molecules (Basel, Switzerland). 2018 Dec; 23(12):. doi: 10.3390/molecules23123234. [PMID: 30544552]
  • Wuwen Feng, Hui Ao, Shijun Yue, Cheng Peng. Systems pharmacology reveals the unique mechanism features of Shenzhu Capsule for treatment of ulcerative colitis in comparison with synthetic drugs. Scientific reports. 2018 11; 8(1):16160. doi: 10.1038/s41598-018-34509-1. [PMID: 30385774]
  • Yan-Ping Huang, Tian-Hua Yang, Zhi-Yan Jin, Ya Wang, Hong-Wei Ye, Qin Gao, Zheng-Hong Li. [Role of mitochondrial permeability transition pore in mediating the effect of endomorphin-1 postconditioning against myocardial ischemia-reperfusion injury in rats]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University. 2018 May; 38(5):547-553. doi: NULL. [PMID: 29891450]
  • Kelly C S Godoy, Paula V Leal, Marcelo A Araújo, Alda I Souza, Arnildo Pott, Stephen T Lee, Claudio S L Barros, Ricardo A A de Lemos. Experimental poisoning by Vernonia rubricaulis in sheep. Toxicon : official journal of the International Society on Toxinology. 2018 Jan; 141(?):9-14. doi: 10.1016/j.toxicon.2017.11.002. [PMID: 29128544]
  • Joonseok Cho, Yujian Zhang, Shi-Young Park, Anna-Maria Joseph, Chul Han, Hyo-Jin Park, Srilaxmi Kalavalapalli, Sung-Kook Chun, Drake Morgan, Jae-Sung Kim, Shinichi Someya, Clayton E Mathews, Young Jae Lee, Stephanie E Wohlgemuth, Nishanth E Sunny, Hui-Young Lee, Cheol Soo Choi, Takayuki Shiratsuchi, S Paul Oh, Naohiro Terada. Mitochondrial ATP transporter depletion protects mice against liver steatosis and insulin resistance. Nature communications. 2017 02; 8(?):14477. doi: 10.1038/ncomms14477. [PMID: 28205519]
  • Stefanie Nikles, Heidi Heuberger, Eberhard Hilsdorf, Robert Schmücker, Rebecca Seidenberger, Rudolf Bauer. Influence of Processing on the Content of Toxic Carboxyatractyloside and Atractyloside and the Microbiological Status of Xanthium sibiricum Fruits (Cang'erzi). Planta medica. 2015 Aug; 81(12-13):1213-20. doi: 10.1055/s-0035-1546207. [PMID: 26287695]
  • Jérémy Carlier, Ludovic Romeuf, Jérôme Guitton, Cédric Priez-Barallon, Fabien Bévalot, Laurent Fanton, Yvan Gaillard. A validated method for quantifying atractyloside and carboxyatractyloside in blood by HPLC-HRMS/MS, a non-fatal case of intoxication with Atractylis gummifera L. Journal of analytical toxicology. 2014 Nov; 38(9):619-27. doi: 10.1093/jat/bku078. [PMID: 24990875]
  • Christo J Botha, Dries Lessing, Magda Rösemann, Erna van Wilpe, June H Williams. Analytical confirmation of Xanthium strumarium poisoning in cattle. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 2014 Sep; 26(5):640-5. doi: 10.1177/1040638714542867. [PMID: 25012081]
  • Ching-Hsueh Cheng, Han-Chen Lin, I-Rue Lai, Hong-Shiee Lai. Ischemic postconditioning attenuate reperfusion injury of small intestine: impact of mitochondrial permeability transition. Transplantation. 2013 Feb; 95(4):559-65. doi: 10.1097/tp.0b013e31827e6b02. [PMID: 23423267]
  • Liang-Yu Chen, Anren Hu, Chih-Jui Chang. The degradation mechanism of toxic atractyloside in herbal medicines by decoction. Molecules (Basel, Switzerland). 2013 Feb; 18(2):2018-28. doi: 10.3390/molecules18022018. [PMID: 23385339]
  • Federico Giannitti, Carlos A Margineda, María S Cid, Santiago S Diab, Natalia Weber, Alejandro Rodríguez, Carlos M Campero, Ernesto R Odriozola. Mortality of a captive axis deer (Axis axis) and a llama (Lama glama) due to ingestion of Wedelia glauca. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 2012 Nov; 24(6):1068-72. doi: 10.1177/1040638712458784. [PMID: 22977113]
  • Rui Song, Huining Bian, Xuliang Huang, Ke-seng Zhao. Atractyloside induces low contractile reaction of arteriolar smooth muscle through mitochondrial damage. Journal of applied toxicology : JAT. 2012 Jun; 32(6):402-8. doi: 10.1002/jat.1688. [PMID: 21598287]
  • Samir Ahid, Mina Ait El Cadi, Bouchra Meddah, Yahia Cherrah. [Atractylis gummifera: from poisoning to the analytic methods]. Annales de biologie clinique. 2012 May; 70(3):263-8. doi: 10.1684/abc.2012.0699. [PMID: 22565173]
  • Yang Wang, Ting Han, Li-Ming Xue, Ping Han, Qiao-Yan Zhang, Bao-Kang Huang, Hong Zhang, Qian-Liang Ming, Wei Peng, Lu-Ping Qin. Hepatotoxicity of kaurene glycosides from Xanthium strumarium L. fruits in mice. Die Pharmazie. 2011 Jun; 66(6):445-9. doi: NULL. [PMID: 21699085]
  • Enara Aguirre, Susana Cadenas. GDP and carboxyatractylate inhibit 4-hydroxynonenal-activated proton conductance to differing degrees in mitochondria from skeletal muscle and heart. Biochimica et biophysica acta. 2010 Oct; 1797(10):1716-26. doi: 10.1016/j.bbabio.2010.06.009. [PMID: 20599679]
  • Asma Bouziri, Asma Hamdi, Khaled Menif, Nejla Ben Jaballah. Hepatorenal injury induced by cutaneous application of Atractylis gummifera L. Clinical toxicology (Philadelphia, Pa.). 2010 Aug; 48(7):752-4. doi: 10.3109/15563650.2010.498379. [PMID: 20615152]
  • Guo-Hua Lin, Lin Lin, Hua-Wei Liang, Xin Ma, Jing-Ye Wang, Li-Ping Wu, Hui-Di Jiang, Iain C Bruce, Qiang Xia. Antioxidant action of a Chrysanthemum morifolium extract protects rat brain against ischemia and reperfusion injury. Journal of medicinal food. 2010 Apr; 13(2):306-11. doi: 10.1089/jmf.2009.1184. [PMID: 20412018]
  • Noemí García, Cecilia Zazueta, Mohammed El-Hafidi, Natalia Pavón, Eduardo Martínez-Abundis, Luz Hernández-Esquivel, Edmundo Chávez. Cyclosporin A inhibits UV-radiation-induced membrane damage but is unable to inhibit carboxyatractyloside-induced permeability transition. Radiation research. 2009 Nov; 172(5):575-83. doi: 10.1667/rr1799.1. [PMID: 19883225]
  • Martin Jastroch, Kerry W Withers, Sigrid Stoehr, Martin Klingenspor. Mitochondrial proton conductance in skeletal muscle of a cold-exposed marsupial, Antechinus flavipes, is unlikely to be involved in adaptive nonshivering thermogenesis but displays increased sensitivity toward carbon-centered radicals. Physiological and biochemical zoology : PBZ. 2009 Sep; 82(5):447-54. doi: 10.1086/603631. [PMID: 19614545]
  • Z G Amerkhanov, I Yu Kashapova, V N Popov. The role of UCP2 and ADP/ATP antiporter in superoxide radical-induced uncoupling in kidney mitochondria. Doklady. Biochemistry and biophysics. 2008 Nov; 423(?):328-30. doi: 10.1134/s1607672908060021. [PMID: 19230380]
  • Cláudia V Pereira, Nuno G Machado, Paulo J Oliveira. Mechanisms of berberine (natural yellow 18)-induced mitochondrial dysfunction: interaction with the adenine nucleotide translocator. Toxicological sciences : an official journal of the Society of Toxicology. 2008 Oct; 105(2):408-17. doi: 10.1093/toxsci/kfn131. [PMID: 18599498]
  • Jennifer M Johnston, Syma Khalid, Mark S P Sansom. Conformational dynamics of the mitochondrial ADP/ATP carrier: a simulation study. Molecular membrane biology. 2008 Sep; 25(6-7):506-17. doi: 10.1080/09687680802459271. [PMID: 18988066]
  • V N Samartsev, O V Kozhina. Oxidative stress as regulatory factor for fatty-acid-induced uncoupling involving liver mitochondrial ADP/ATP and aspartate/glutamate antiporters of old rats. Biochemistry. Biokhimiia. 2008 Jul; 73(7):783-90. doi: 10.1134/s0006297908070067. [PMID: 18707586]
  • Nadeene Parker, Charles Affourtit, Antonio Vidal-Puig, Martin D Brand. Energization-dependent endogenous activation of proton conductance in skeletal muscle mitochondria. The Biochemical journal. 2008 May; 412(1):131-9. doi: 10.1042/bj20080006. [PMID: 18251717]
  • Jian Yin, Donghui Li, Weiming Hu, Qin Meng. Effects of glycyrrhizic acid on cocklebur-induced hepatotoxicity in rat and human hepatocytes. Phytotherapy research : PTR. 2008 Mar; 22(3):395-400. doi: 10.1002/ptr.2336. [PMID: 18058991]
  • Valérie Razakantoanina, Isabelle Florent, Ginette Jaureguiberry. Plasmodium falciparum: functional mitochondrial ADP/ATP transporter in Escherichia coli plasmic membrane as a tool for selective drug screening. Experimental parasitology. 2008 Feb; 118(2):181-7. doi: 10.1016/j.exppara.2007.07.015. [PMID: 17920591]
  • Lubica Malekova, Viera Kominkova, Miroslav Ferko, Peter Stefanik, Olga Krizanova, Attila Ziegelhöffer, Adam Szewczyk, Karol Ondrias. Bongkrekic acid and atractyloside inhibits chloride channels from mitochondrial membranes of rat heart. Biochimica et biophysica acta. 2007 Jan; 1767(1):31-44. doi: 10.1016/j.bbabio.2006.10.004. [PMID: 17123460]
  • P A Steenkamp, N M Harding, F R van Heerden, B-E van Wyk. Identification of atractyloside by LC-ESI-MS in alleged herbal poisonings. Forensic science international. 2006 Nov; 163(1-2):81-92. doi: 10.1016/j.forsciint.2005.11.010. [PMID: 16376039]
  • Lyudmila S Khailova, Elena A Prikhodko, Vera I Dedukhova, Elena N Mokhova, Vasily N Popov, Vladimir P Skulachev. Participation of ATP/ADP antiporter in oleate- and oleate hydroperoxide-induced uncoupling suppressed by GDP and carboxyatractylate. Biochimica et biophysica acta. 2006 Sep; 1757(9-10):1324-9. doi: 10.1016/j.bbabio.2006.04.024. [PMID: 16765906]
  • Noemí García, Eduardo Martínez-Abundis, Natalia Pavón, Edmundo Chávez. Sodium inhibits permeability transition by decreasing potassium matrix content in rat kidney mitochondria. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2006 Aug; 144(4):442-50. doi: 10.1016/j.cbpb.2006.04.002. [PMID: 16762575]
  • Daniela Trono, Mario Soccio, Anna M Mastrangelo, Vanessa De Simone, Natale Di Fonzo, Donato Pastore. The transcript levels of two plant mitochondrial uncoupling protein (pUCP)-related genes are not affected by hyperosmotic stress in durum wheat seedlings showing an increased level of pUCP activity. Bioscience reports. 2006 Jun; 26(3):251-61. doi: 10.1007/s10540-006-9020-1. [PMID: 16855867]
  • Tatiana Brustovetsky, Natalia Shalbuyeva, Nickolay Brustovetsky. Lack of manifestations of diazoxide/5-hydroxydecanoate-sensitive KATP channel in rat brain nonsynaptosomal mitochondria. The Journal of physiology. 2005 Oct; 568(Pt 1):47-59. doi: 10.1113/jphysiol.2005.091199. [PMID: 16051627]
  • Edmundo Chávez, José S Rodríguez, Gerardo García, Noemí García, Francisco Correa. Oligomycin strengthens the effect of cyclosporin A on mitochondrial permeability transition by inducing phosphate uptake. Cell biology international. 2005 Jul; 29(7):551-8. doi: 10.1016/j.cellbi.2005.03.009. [PMID: 15979905]
  • Mehmet Turgut, Cafer Cumhur Alhan, Metin Gürgöze, Abdullah Kurt, Yaşar Doğan, Muhittin Tekatli, Nusret Akpolat, A Denizmen Aygün. Carboxyatractyloside poisoning in humans. Annals of tropical paediatrics. 2005 Jun; 25(2):125-34. doi: 10.1179/146532805x45728. [PMID: 15949201]
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