Urolithin B (BioDeep_00000021000)

 

Secondary id: BioDeep_00000410504

human metabolite Endogenous blood metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3-hydroxy-6H-benzo[c]chromen-6-one

化学式: C13H8O3 (212.0473418)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.14%

分子结构信息

SMILES: C1=CC=C2C(=C1)C3=C(C=C(C=C3)O)OC2=O
InChI: InChI=1S/C13H8O3/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)16-12(10)7-8/h1-7,14H

描述信息

Urolithin B is a secondary metabolite of ellagic acid which may be glucuronidated by liver enzymes during phase II metabolism.
A polyphenol metabolite detected in biological fluids [PhenolExplorer]
Urolithin B is one of Ellagitannins' slow microbial products, and has anti-inflammatory and anti-inflammatory effects. Urolithin B suppresses NF-κB activity. Urolithin B suppresses JNK, ERK and Akt's oxidation, and increases AMPK's oxidation. Urolithin B is also a quantitative change factor for bone and skin quality[1][2][3][4].
Urolithin B is one of the gut microbial metabolites of ellagitannins, and has anti-inflammatory and antioxidant effects. Urolithin B inhibits NF-κB activity by reducing the phosphorylation and degradation of IκBα, and suppresses the phosphorylation of JNK, ERK, and Akt, and enhances the phosphorylation of AMPK. Urolithin B is also a regulator of skeletal muscle mass[1][2].
Urolithin B is one of Ellagitannins' slow microbial products, and has anti-inflammatory and anti-inflammatory effects. Urolithin B suppresses NF-κB activity. Urolithin B suppresses JNK, ERK and Akt's oxidation, and increases AMPK's oxidation. Urolithin B is also a quantitative change factor for bone and skin quality[1][2][3][4].
Urolithin B is one of the gut microbial metabolites of ellagitannins, and has anti-inflammatory and antioxidant effects. Urolithin B inhibits NF-κB activity by reducing the phosphorylation and degradation of IκBα, and suppresses the phosphorylation of JNK, ERK, and Akt, and enhances the phosphorylation of AMPK. Urolithin B is also a regulator of skeletal muscle mass[1][2].

同义名列表

4 个代谢物同义名

3-hydroxy-6H-benzo[c]chromen-6-one; 3-hydroxybenzo[c]chromen-6-one; 3-hydroxy-urolithin; urolithin B



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(1)

PlantCyc(0)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

10 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

  • M Tolmie, M J Bester, J C Serem, M Nell, Z Apostolides. The potential antidiabetic properties of green and purple tea [Camellia sinensis (L.) O Kuntze], purple tea ellagitannins, and urolithins. Journal of ethnopharmacology. 2023 Jun; 309(?):116377. doi: 10.1016/j.jep.2023.116377. [PMID: 36907477]
  • Abdulrasheed O Abdulrahman, Mohammed Yahya Alzubaidi, Muhammad Shahid Nadeem, Jalaluddin Awlia Khan, Irfan A Rather, Mohammad Imran Khan. Effects of urolithins on obesity-associated gut dysbiosis in rats fed on a high-fat diet. International journal of food sciences and nutrition. 2021 Nov; 72(7):923-934. doi: 10.1080/09637486.2021.1886255. [PMID: 33618593]
  • Ali Khalaf Al Khalaf, Abdulrasheed O Abdulrahman, Mohammed Kaleem, Suza Mohammad Nur, Amer H Asseri, Hani Choudhry, Mohammad Imran Khan. Comparative Analysis of the Impact of Urolithins on the Composition of the Gut Microbiota in Normal-Diet Fed Rats. Nutrients. 2021 Oct; 13(11):. doi: 10.3390/nu13113885. [PMID: 34836145]
  • Abdulaziz Musa Alzahrani, Mohammed Razeeth Shait Mohammed, Raed Ahmed Alghamdi, Abrar Ahmad, Mazin A Zamzami, Hani Choudhry, Mohammad Imran Khan. Urolithin A and B Alter Cellular Metabolism and Induce Metabolites Associated with Apoptosis in Leukemic Cells. International journal of molecular sciences. 2021 May; 22(11):. doi: 10.3390/ijms22115465. [PMID: 34067305]
  • Juan Antonio Giménez-Bastida, Antonio González-Sarrías, Juan Carlos Espín, Claus Schneider. Inhibition of 5-Lipoxygenase-Derived Leukotrienes and Hemiketals as a Novel Anti-Inflammatory Mechanism of Urolithins. Molecular nutrition & food research. 2020 06; 64(11):e2000129. doi: 10.1002/mnfr.202000129. [PMID: 32306507]
  • Luis Cisneros-Zevallos, Woo Young Bang, Claudia Delgadillo-Puga. Ellagic Acid and Urolithins A and B Differentially Regulate Fat Accumulation and Inflammation in 3T3-L1 Adipocytes While Not Affecting Adipogenesis and Insulin Sensitivity. International journal of molecular sciences. 2020 Mar; 21(6):. doi: 10.3390/ijms21062086. [PMID: 32197417]
  • Izaskun García-Mantrana, Marta Calatayud, María Romo-Vaquero, Juan Carlos Espín, María V Selma, María Carmen Collado. Urolithin Metabotypes Can Determine the Modulation of Gut Microbiota in Healthy Individuals by Tracking Walnuts Consumption over Three Days. Nutrients. 2019 Oct; 11(10):. doi: 10.3390/nu11102483. [PMID: 31623169]
  • Adrián Cortés-Martín, María Romo-Vaquero, Izaskun García-Mantrana, Ana Rodríguez-Varela, María Carmen Collado, Juan Carlos Espín, María Victoria Selma. Urolithin Metabotypes can Anticipate the Different Restoration of the Gut Microbiota and Anthropometric Profiles during the First Year Postpartum. Nutrients. 2019 Sep; 11(9):. doi: 10.3390/nu11092079. [PMID: 31484413]
  • Wenhua Zhao, Lixue Wang, Viktoria Haller, Andreas Ritsch. A Novel Candidate for Prevention and Treatment of Atherosclerosis: Urolithin B Decreases Lipid Plaque Deposition in apoE-/- Mice and Increases Early Stages of Reverse Cholesterol Transport in ox-LDL Treated Macrophages Cells. Molecular nutrition & food research. 2019 05; 63(10):e1800887. doi: 10.1002/mnfr.201800887. [PMID: 30762936]
  • Gyeongjin Lee, Jin-Sun Park, Eun-Jung Lee, Jung-Hyuck Ahn, Hee-Sun Kim. Anti-inflammatory and antioxidant mechanisms of urolithin B in activated microglia. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Mar; 55(?):50-57. doi: 10.1016/j.phymed.2018.06.032. [PMID: 30668443]
  • Nicholas A DaSilva, Pragati P Nahar, Hang Ma, Aseel Eid, Zhengxi Wei, Susan Meschwitz, Nasser H Zawia, Angela L Slitt, Navindra P Seeram. Pomegranate ellagitannin-gut microbial-derived metabolites, urolithins, inhibit neuroinflammation in vitro. Nutritional neuroscience. 2019 Mar; 22(3):185-195. doi: 10.1080/1028415x.2017.1360558. [PMID: 28784051]
  • María Romo-Vaquero, Adrián Cortés-Martín, Viviana Loria-Kohen, Ana Ramírez-de-Molina, Izaskun García-Mantrana, María Carmen Collado, Juan Carlos Espín, María Victoria Selma. Deciphering the Human Gut Microbiome of Urolithin Metabotypes: Association with Enterotypes and Potential Cardiometabolic Health Implications. Molecular nutrition & food research. 2019 02; 63(4):e1800958. doi: 10.1002/mnfr.201800958. [PMID: 30471188]
  • María Ángeles Ávila-Gálvez, Juan Carlos Espín, Antonio González-Sarrías. Physiological Relevance of the Antiproliferative and Estrogenic Effects of Dietary Polyphenol Aglycones versus Their Phase-II Metabolites on Breast Cancer Cells: A Call of Caution. Journal of agricultural and food chemistry. 2018 Aug; 66(32):8547-8555. doi: 10.1021/acs.jafc.8b03100. [PMID: 30025453]
  • María V Selma, Antonio González-Sarrías, Jordi Salas-Salvadó, Cristina Andrés-Lacueva, Cesarettin Alasalvar, Asım Örem, Francisco A Tomás-Barberán, Juan C Espín. The gut microbiota metabolism of pomegranate or walnut ellagitannins yields two urolithin-metabotypes that correlate with cardiometabolic risk biomarkers: Comparison between normoweight, overweight-obesity and metabolic syndrome. Clinical nutrition (Edinburgh, Scotland). 2018 06; 37(3):897-905. doi: 10.1016/j.clnu.2017.03.012. [PMID: 28347564]
  • Marc Francaux, Louise Deldicque. Using polyphenol derivatives to prevent muscle wasting. Current opinion in clinical nutrition and metabolic care. 2018 05; 21(3):159-163. doi: 10.1097/mco.0000000000000455. [PMID: 29356695]
  • Julie Rodriguez, Nicolas Pierre, Damien Naslain, Françoise Bontemps, Daneel Ferreira, Fabian Priem, Louise Deldicque, Marc Francaux. Urolithin B, a newly identified regulator of skeletal muscle mass. Journal of cachexia, sarcopenia and muscle. 2017 Aug; 8(4):583-597. doi: 10.1002/jcsm.12190. [PMID: 28251839]
  • Rocío García-Villalba, Hanne Vissenaekens, Judit Pitart, María Romo-Vaquero, Juan C Espín, Charlotte Grootaert, María V Selma, Katleen Raes, Guy Smagghe, Sam Possemiers, John Van Camp, Francisco A Tomas-Barberan. Gastrointestinal Simulation Model TWIN-SHIME Shows Differences between Human Urolithin-Metabotypes in Gut Microbiota Composition, Pomegranate Polyphenol Metabolism, and Transport along the Intestinal Tract. Journal of agricultural and food chemistry. 2017 Jul; 65(27):5480-5493. doi: 10.1021/acs.jafc.7b02049. [PMID: 28616977]
  • Monia Savi, Leonardo Bocchi, Pedro Mena, Margherita Dall'Asta, Alan Crozier, Furio Brighenti, Donatella Stilli, Daniele Del Rio. In vivo administration of urolithin A and B prevents the occurrence of cardiac dysfunction in streptozotocin-induced diabetic rats. Cardiovascular diabetology. 2017 07; 16(1):80. doi: 10.1186/s12933-017-0561-3. [PMID: 28683791]
  • Jakub P Piwowarski, Iwona Stanisławska, Sebastian Granica, Joanna Stefańska, Anna K Kiss. Phase II Conjugates of Urolithins Isolated from Human Urine and Potential Role of β-Glucuronidases in Their Disposition. Drug metabolism and disposition: the biological fate of chemicals. 2017 06; 45(6):657-665. doi: 10.1124/dmd.117.075200. [PMID: 28283501]
  • Pedro Mena, Margherita Dall'Asta, Luca Calani, Furio Brighenti, Daniele Del Rio. Gastrointestinal stability of urolithins: an in vitro approach. European journal of nutrition. 2017 Feb; 56(1):99-106. doi: 10.1007/s00394-015-1061-4. [PMID: 26439723]
  • Pilar Gaya, Margarita Medina, Abel Sánchez-Jiménez, José Mᵃ Landete. Phytoestrogen Metabolism by Adult Human Gut Microbiota. Molecules (Basel, Switzerland). 2016 Aug; 21(8):. doi: 10.3390/molecules21081034. [PMID: 27517891]
  • Laura Mele, Pedro Mena, Antonio Piemontese, Valentina Marino, Noelia López-Gutiérrez, Franco Bernini, Furio Brighenti, Ilaria Zanotti, Daniele Del Rio. Antiatherogenic effects of ellagic acid and urolithins in vitro. Archives of biochemistry and biophysics. 2016 06; 599(?):42-50. doi: 10.1016/j.abb.2016.02.017. [PMID: 26891591]
  • Inhae Kang, YongEun Kim, Francisco A Tomás-Barberán, Juan Carlos Espín, Soonkyu Chung. Urolithin A, C, and D, but not iso-urolithin A and urolithin B, attenuate triglyceride accumulation in human cultures of adipocytes and hepatocytes. Molecular nutrition & food research. 2016 05; 60(5):1129-38. doi: 10.1002/mnfr.201500796. [PMID: 26872561]
  • Jieping Yang, Rupo Lee, Susanne M Henning, Gail Thames, Mark Hsu, Hei ManLam, David Heber, Zhaoping Li. Soy protein isolate does not affect ellagitannin bioavailability and urolithin formation when mixed with pomegranate juice in humans. Food chemistry. 2016 Mar; 194(?):1300-3. doi: 10.1016/j.foodchem.2015.08.099. [PMID: 26471685]
  • Jakub P Piwowarski, Anna K Kiss, Sebastian Granica, Thomas Moeslinger. Urolithins, gut microbiota-derived metabolites of ellagitannins, inhibit LPS-induced inflammation in RAW 264.7 murine macrophages. Molecular nutrition & food research. 2015 Nov; 59(11):2168-77. doi: 10.1002/mnfr.201500264. [PMID: 26202092]
  • Daniil N Olennikov, Nina I Kashchenko, Nadezhda K Chirikova. In Vitro Bioaccessibility, Human Gut Microbiota Metabolites and Hepatoprotective Potential of Chebulic Ellagitannins: A Case of Padma Hepaten® Formulation. Nutrients. 2015 Oct; 7(10):8456-77. doi: 10.3390/nu7105406. [PMID: 26473917]
  • Wenhua Zhao, Yuji Wang, Weijia Hao, Hua Yang, Xueying Song, Ming Zhao, Shiqi Peng. Preparative isolation and purification of urolithins from the intestinal metabolites of pomegranate ellagitannins by high-speed counter-current chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 May; 990(?):111-7. doi: 10.1016/j.jchromb.2015.03.024. [PMID: 25864012]
  • Claudia Sánchez-González, Carlos J Ciudad, Véronique Noé, Maria Izquierdo-Pulido. Walnut polyphenol metabolites, urolithins A and B, inhibit the expression of the prostate-specific antigen and the androgen receptor in prostate cancer cells. Food & function. 2014 Nov; 5(11):2922-30. doi: 10.1039/c4fo00542b. [PMID: 25214070]
  • Beate Pfundstein, Roswitha Haubner, Gerd Würtele, Nicole Gehres, Cornelia M Ulrich, Robert W Owen. Pilot walnut intervention study of urolithin bioavailability in human volunteers. Journal of agricultural and food chemistry. 2014 Oct; 62(42):10264-73. doi: 10.1021/jf5040652. [PMID: 25275327]
  • Jakub P Piwowarski, Sebastian Granica, Marta Zwierzyńska, Joanna Stefańska, Patrick Schopohl, Matthias F Melzig, Anna K Kiss. Role of human gut microbiota metabolism in the anti-inflammatory effect of traditionally used ellagitannin-rich plant materials. Journal of ethnopharmacology. 2014 Aug; 155(1):801-9. doi: 10.1016/j.jep.2014.06.032. [PMID: 24969824]
  • Francisco A Tomás-Barberán, Rocío García-Villalba, Antonio González-Sarrías, María V Selma, Juan C Espín. Ellagic acid metabolism by human gut microbiota: consistent observation of three urolithin phenotypes in intervention trials, independent of food source, age, and health status. Journal of agricultural and food chemistry. 2014 Jul; 62(28):6535-8. doi: 10.1021/jf5024615. [PMID: 24976365]
  • Jakub P Piwowarski, Sebastian Granica, Anna K Kiss. Influence of gut microbiota-derived ellagitannins' metabolites urolithins on pro-inflammatory activities of human neutrophils. Planta medica. 2014 Jul; 80(11):887-95. doi: 10.1055/s-0034-1368615. [PMID: 24995502]
  • Begoña Cerdá, Francisco A Tomás-Barberán, Juan Carlos Espín. Metabolism of antioxidant and chemopreventive ellagitannins from strawberries, raspberries, walnuts, and oak-aged wine in humans: identification of biomarkers and individual variability. Journal of agricultural and food chemistry. 2005 Jan; 53(2):227-35. doi: 10.1021/jf049144d. [PMID: 15656654]
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