Oleocanthal (BioDeep_00000840375)

   

natural product


代谢物信息卡片


Oleocanthal

化学式: C17H20O5 (304.13106700000003)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C/C=C(/C=O)[C@@H](CC=O)CC(=O)OCCc1ccc(O)cc1
InChI: InChI=1S/C17H20O5/c1-2-14(12-19)15(7-9-18)11-17(21)22-10-8-13-3-5-16(20)6-4-13/h2-6,9,12,15,20H,7-8,10-11H2,1H3/t15-/m0/s1

描述信息

A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture.

同义名列表

1 个代谢物同义名

Oleocanthal



数据库引用编号

7 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)

8 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

  • Juhee Cho, Meriem Bejaoui, Kenichi Tominaga, Hiroko Isoda. Comparative Analysis of Olive-Derived Phenolic Compounds' Pro-Melanogenesis Effects on B16F10 Cells and Epidermal Human Melanocytes. International journal of molecular sciences. 2024 Apr; 25(8):. doi: 10.3390/ijms25084479. [PMID: 38674064]
  • Anabel González-Acedo, Rebeca Illescas-Montes, Elvira de Luna-Bertos, Concepción Ruiz, Javier Ramos-Torrecillas, Olga García-Martínez, Lucía Melguizo-Rodríguez. Extra Virgin Olive Oil Phenolic Compounds Modulate the Gene Expression of Biomarkers Involved in Fibroblast Proliferation and Differentiation. Genes. 2024 Jan; 15(2):. doi: 10.3390/genes15020173. [PMID: 38397163]
  • Fernando Rivero-Pino. Oleocanthal - Characterization, production, safety, functionality and in vivo evidences. Food chemistry. 2023 Nov; 425(?):136504. doi: 10.1016/j.foodchem.2023.136504. [PMID: 37276673]
  • Ignacio Ruiz-García, Rodolfo Ortíz-Flores, Rocío Badía, Aranzazu García-Borrego, María García-Fernández, Estrella Lara, Elisa Martín-Montañez, Sara García-Serrano, Sergio Valdés, Montserrat Gonzalo, María-José Tapia-Guerrero, José-Carlos Fernández-García, Alicia Sánchez-García, Francisca Muñoz-Cobos, Miguel Calderón-Cid, Rajaa El-Bekay, María-Isabel Covas, Gemma Rojo-Martínez, Gabriel Olveira, Silvana-Yanina Romero-Zerbo, Francisco-Javier Bermúdez-Silva. Rich oleocanthal and oleacein extra virgin olive oil and inflammatory and antioxidant status in people with obesity and prediabetes. The APRIL study: A randomised, controlled crossover study. Clinical nutrition (Edinburgh, Scotland). 2023 08; 42(8):1389-1398. doi: 10.1016/j.clnu.2023.06.027. [PMID: 37421852]
  • Annalisa Noce, Giulia Marrone, Silvia Urciuoli, Francesca Di Daniele, Manuela Di Lauro, Anna Pietroboni Zaitseva, Nicola Di Daniele, Annalisa Romani. Usefulness of Extra Virgin Olive Oil Minor Polar Compounds in the Management of Chronic Kidney Disease Patients. Nutrients. 2021 Feb; 13(2):. doi: 10.3390/nu13020581. [PMID: 33578682]
  • Martina Starec, Antonella Calabretti, Federico Berti, Cristina Forzato. Oleocanthal Quantification Using 1H NMR Spectroscopy and Polyphenols HPLC Analysis of Olive Oil from the Bianchera/Belica Cultivar. Molecules (Basel, Switzerland). 2021 Jan; 26(1):. doi: 10.3390/molecules26010242. [PMID: 33466567]
  • Xiuye Liu, Lijuan Yang, Li Wang, Qiongmei Guo. Oleocanthal protects against neuronal inflammation and cardiopulmonary bypass surgery-induced brain injury in rats by regulating the NLRP3 pathway. Restorative neurology and neuroscience. 2021; 39(1):39-44. doi: 10.3233/rnn-201073. [PMID: 33554928]
  • Antonio Francioso, Rodolfo Federico, Anna Maggiore, Mario Fontana, Alberto Boffi, Maria D'Erme, Luciana Mosca. Green Route for the Isolation and Purification of Hyrdoxytyrosol, Tyrosol, Oleacein and Oleocanthal from Extra Virgin Olive Oil. Molecules (Basel, Switzerland). 2020 Aug; 25(16):. doi: 10.3390/molecules25163654. [PMID: 32796621]
  • Georgia Sarikaki, Nikoleta Christoforidou, Nicolas Gaboriaud-Kolar, Amos B Smith, Ioannis K Kostakis, Alexios-Leandros Skaltsounis. Biomimetic Synthesis of Oleocanthal, Oleacein, and Their Analogues Starting from Oleuropein, A Major Compound of Olive Leaves. Journal of natural products. 2020 06; 83(6):1735-1739. doi: 10.1021/acs.jnatprod.0c00086. [PMID: 32441936]
  • Rekha Grewal, Martina Reutzel, Benjamin Dilberger, Hannah Hein, Jens Zotzel, Stefan Marx, Joachim Tretzel, Alla Sarafeddinov, Christopher Fuchs, Gunter P Eckert. Purified oleocanthal and ligstroside protect against mitochondrial dysfunction in models of early Alzheimer's disease and brain ageing. Experimental neurology. 2020 06; 328(?):113248. doi: 10.1016/j.expneurol.2020.113248. [PMID: 32084452]
  • Panagiotis Diamantakos, Triada Giannara, Maria Skarkou, Eleni Melliou, Prokopios Magiatis. Influence of Harvest Time and Malaxation Conditions on the Concentration of Individual Phenols in Extra Virgin Olive Oil Related to Its Healthy Properties. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102449. [PMID: 32456326]
  • Tatiana Montoya, Maria L Castejón, Marina Sánchez-Hidalgo, Alejandro González-Benjumea, José G Fernández-Bolaños, Catalina Alarcón de-la-Lastra. Oleocanthal Modulates LPS-Induced Murine Peritoneal Macrophages Activation via Regulation of Inflammasome, Nrf-2/HO-1, and MAPKs Signaling Pathways. Journal of agricultural and food chemistry. 2019 May; 67(19):5552-5559. doi: 10.1021/acs.jafc.9b00771. [PMID: 31042377]
  • M Figueiredo-González, P Reboredo-Rodríguez, C González-Barreiro, A Carrasco-Pancorbo, B Cancho-Grande, J Simal-Gándara. The involvement of phenolic-rich extracts from Galician autochthonous extra-virgin olive oils against the α-glucosidase and α-amylase inhibition. Food research international (Ottawa, Ont.). 2019 02; 116(?):447-454. doi: 10.1016/j.foodres.2018.08.060. [PMID: 30716967]
  • Juan Manuel Segura Palacios, Nuria Blázquez Sánchez, Francisco Rivas Ruiz, Miguel Aguilar Bernier, Belén Ramírez López, María Encarnación Fernández Sánchez, Magdalena de Troya Martín. Topical treatment with oleocanthal extract in reducing inflammatory reactions after photodynamic therapy: a prospective quasi-experimental pilot study. Complementary therapies in medicine. 2019 Feb; 42(?):298-301. doi: 10.1016/j.ctim.2018.12.003. [PMID: 30670258]
  • Limor Goren, George Zhang, Susmita Kaushik, Paul A S Breslin, Yi-Chieh Nancy Du, David A Foster. (-)-Oleocanthal and (-)-oleocanthal-rich olive oils induce lysosomal membrane permeabilization in cancer cells. PloS one. 2019; 14(8):e0216024. doi: 10.1371/journal.pone.0216024. [PMID: 31412041]
  • H Miho, C M Díez, A Mena-Bravo, V Sánchez de Medina, J Moral, E Melliou, P Magiatis, L Rallo, D Barranco, F Priego-Capote. Cultivar influence on variability in olive oil phenolic profiles determined through an extensive germplasm survey. Food chemistry. 2018 Nov; 266(?):192-199. doi: 10.1016/j.foodchem.2018.06.002. [PMID: 30381176]
  • Monika E Czerwińska, Emilia Gąsińska, Anna Leśniak, Paulina Krawczyk, Anna K Kiss, Marek Naruszewicz, Magdalena Bujalska-Zadrożny. Inhibitory effect of Ligustrum vulgare leaf extract on the development of neuropathic pain in a streptozotocin-induced rat model of diabetes. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Oct; 49(?):75-82. doi: 10.1016/j.phymed.2018.06.006. [PMID: 30217264]
  • Beatrice Polini, Maria Digiacomo, Sara Carpi, Simone Bertini, Francesca Gado, Giuseppe Saccomanni, Marco Macchia, Paola Nieri, Clementina Manera, Stefano Fogli. Oleocanthal and oleacein contribute to the in vitro therapeutic potential of extra virgin oil-derived extracts in non-melanoma skin cancer. Toxicology in vitro : an international journal published in association with BIBRA. 2018 Oct; 52(?):243-250. doi: 10.1016/j.tiv.2018.06.021. [PMID: 29959992]
  • Laura Giusti, Cristina Angeloni, Maria Cristina Barbalace, Serena Lacerenza, Federica Ciregia, Maurizio Ronci, Andrea Urbani, Clementina Manera, Maria Digiacomo, Marco Macchia, Maria Rosa Mazzoni, Antonio Lucacchini, Silvana Hrelia. A Proteomic Approach to Uncover Neuroprotective Mechanisms of Oleocanthal against Oxidative Stress. International journal of molecular sciences. 2018 Aug; 19(8):. doi: 10.3390/ijms19082329. [PMID: 30096819]
  • Natasa P Kalogiouri, Reza Aalizadeh, Nikolaos S Thomaidis. Application of an advanced and wide scope non-target screening workflow with LC-ESI-QTOF-MS and chemometrics for the classification of the Greek olive oil varieties. Food chemistry. 2018 Aug; 256(?):53-61. doi: 10.1016/j.foodchem.2018.02.101. [PMID: 29606472]
  • Yazan S Batarseh, Loqman A Mohamed, Sweilem B Al Rihani, Youssef M Mousa, Abu Bakar Siddique, Khalid A El Sayed, Amal Kaddoumi. Oleocanthal ameliorates amyloid-β oligomers' toxicity on astrocytes and neuronal cells: In vitro studies. Neuroscience. 2017 06; 352(?):204-215. doi: 10.1016/j.neuroscience.2017.03.059. [PMID: 28392295]
  • Amir Ben Mansour, Boutheina Gargouri, Eleni Melliou, Prokopios Magiatis, Mohamed Bouaziz. Oil quality parameters and quantitative measurement of major secoiridoid derivatives in Neb Jmel olive oil from various Tunisian origins using qNMR. Journal of the science of food and agriculture. 2016 Oct; 96(13):4432-9. doi: 10.1002/jsfa.7654. [PMID: 26841137]
  • Chiara Cassiano, Agostino Casapullo, Alessandra Tosco, Maria Chiara Monti, Raffaele Riccio. In Cell Interactome of Oleocanthal, an Extra Virgin Olive Oil Bioactive Component. Natural product communications. 2015 Jun; 10(6):1013-6. doi: ". [PMID: 26197539]
  • Hamid-Reza Adhami, Martin Zehl, Christina Dangl, Dominic Dorfmeister, Marco Stadler, Ernst Urban, Peter Hewitson, Svetlana Ignatova, Liselotte Krenn. Preparative isolation of oleocanthal, tyrosol, and hydroxytyrosol from olive oil by HPCCC. Food chemistry. 2015 Mar; 170(?):154-9. doi: 10.1016/j.foodchem.2014.08.079. [PMID: 25306330]
  • Lisa Parkinson, Russell Keast. Oleocanthal, a phenolic derived from virgin olive oil: a review of the beneficial effects on inflammatory disease. International journal of molecular sciences. 2014 Jul; 15(7):12323-34. doi: 10.3390/ijms150712323. [PMID: 25019344]
  • Annekathrin Martina Keiler, Oliver Zierau, Ricardo Bernhardt, Dieter Scharnweber, Nikolaos Lemonakis, Aikaterini Termetzi, Leandros Skaltsounis, Günter Vollmer, Maria Halabalaki. Impact of a functionalized olive oil extract on the uterus and the bone in a model of postmenopausal osteoporosis. European journal of nutrition. 2014 Jun; 53(4):1073-81. doi: 10.1007/s00394-013-0609-4. [PMID: 24170065]
  • Konstantina Vougogiannopoulou, Christelle Lemus, Maria Halabalaki, Carlo Pergola, Oliver Werz, Amos B Smith, Sylvie Michel, Leandros Skaltsounis, Brigitte Deguin. One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor. Journal of natural products. 2014 Mar; 77(3):441-5. doi: 10.1021/np401010x. [PMID: 24568174]
  • Luigi Margarucci, Maria Chiara Monti, Chiara Cassiano, Matteo Mozzicafreddo, Mauro Angeletti, Raffaele Riccio, Alessandra Tosco, Agostino Casapullo. Chemical proteomics-driven discovery of oleocanthal as an Hsp90 inhibitor. Chemical communications (Cambridge, England). 2013 Jul; 49(52):5844-6. doi: 10.1039/c3cc41858h. [PMID: 23703283]
  • Alaa H Abuznait, Hisham Qosa, Belnaser A Busnena, Khalid A El Sayed, Amal Kaddoumi. Olive-oil-derived oleocanthal enhances β-amyloid clearance as a potential neuroprotective mechanism against Alzheimer's disease: in vitro and in vivo studies. ACS chemical neuroscience. 2013 Jun; 4(6):973-82. doi: 10.1021/cn400024q. [PMID: 23414128]
  • Rachel Nuwer. Mediterranean mystery. Scientific American. 2013 Jun; 308(6):22. doi: 10.1038/scientificamerican0613-22. [PMID: 23729063]
  • F Ranalli, A Ranalli, S Contento, M Casanovas, M Antonucci, G Di Simone. Bioactives and nutraceutical phytochemicals naturally occurring in virgin olive oil. The case study of the Nocellara del Belice Italian olive cultivar. Natural product research. 2013; 27(18):1686-90. doi: 10.1080/14786419.2012.762918. [PMID: 23356880]
  • M Scotece, R Gómez, J Conde, V Lopez, J J Gómez-Reino, F Lago, A B Smith, O Gualillo. Oleocanthal inhibits proliferation and MIP-1α expression in human multiple myeloma cells. Current medicinal chemistry. 2013; 20(19):2467-75. doi: 10.2174/0929867311320190006. [PMID: 23521677]
  • Evangelia Karkoula, Angeliki Skantzari, Eleni Melliou, Prokopios Magiatis. Direct measurement of oleocanthal and oleacein levels in olive oil by quantitative (1)H NMR. Establishment of a new index for the characterization of extra virgin olive oils. Journal of agricultural and food chemistry. 2012 Nov; 60(47):11696-703. doi: 10.1021/jf3032765. [PMID: 23116297]
  • Maria Chiara Monti, Luigi Margarucci, Raffaele Riccio, Agostino Casapullo. Modulation of tau protein fibrillization by oleocanthal. Journal of natural products. 2012 Sep; 75(9):1584-8. doi: 10.1021/np300384h. [PMID: 22988908]
  • Samantha M Bennett, John E Hayes. Differences in the chemesthetic subqualities of capsaicin, ibuprofen, and olive oil. Chemical senses. 2012 Jun; 37(5):471-8. doi: 10.1093/chemse/bjr129. [PMID: 22281531]
  • Alaa H Abuznait, Hisham Qosa, Nicholas D O'Connell, Jessica Akbarian-Tefaghi, Paul W Sylvester, Khalid A El Sayed, Amal Kaddoumi. Induction of expression and functional activity of P-glycoprotein efflux transporter by bioactive plant natural products. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Nov; 49(11):2765-72. doi: 10.1016/j.fct.2011.08.004. [PMID: 21851848]
  • Ahmed Y Elnagar, Paul W Sylvester, Khalid A El Sayed. (-)-Oleocanthal as a c-Met inhibitor for the control of metastatic breast and prostate cancers. Planta medica. 2011 Jul; 77(10):1013-9. doi: 10.1055/s-0030-1270724. [PMID: 21328179]
  • Maria Chiara Monti, Luigi Margarucci, Alessandra Tosco, Raffaele Riccio, Agostino Casapullo. New insights on the interaction mechanism between tau protein and oleocanthal, an extra-virgin olive-oil bioactive component. Food & function. 2011 Jul; 2(7):423-8. doi: 10.1039/c1fo10064e. [PMID: 21894330]
  • Prem Khanal, Won-Keun Oh, Hyo Jeong Yun, Gwang Mo Namgoong, Sang-Gun Ahn, Seong-Min Kwon, Hoo-Kyun Choi, Hong Seok Choi. p-HPEA-EDA, a phenolic compound of virgin olive oil, activates AMP-activated protein kinase to inhibit carcinogenesis. Carcinogenesis. 2011 Apr; 32(4):545-53. doi: 10.1093/carcin/bgr001. [PMID: 21216846]
  • S Cicerale, X A Conlan, N W Barnett, R S J Keast. The concentration of oleocanthal in olive oil waste. Natural product research. 2011 Mar; 25(5):542-8. doi: 10.1080/14786419.2010.511214. [PMID: 21391116]
  • Catherine Peyrot des Gachons, Kunitoshi Uchida, Bruce Bryant, Asako Shima, Jeffrey B Sperry, Luba Dankulich-Nagrudny, Makoto Tominaga, Amos B Smith, Gary K Beauchamp, Paul A S Breslin. Unusual pungency from extra-virgin olive oil is attributable to restricted spatial expression of the receptor of oleocanthal. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2011 Jan; 31(3):999-1009. doi: 10.1523/jneurosci.1374-10.2011. [PMID: 21248124]
  • Lisa Lucas, Aaron Russell, Russell Keast. Molecular mechanisms of inflammation. Anti-inflammatory benefits of virgin olive oil and the phenolic compound oleocanthal. Current pharmaceutical design. 2011; 17(8):754-68. doi: 10.2174/138161211795428911. [PMID: 21443487]
  • Sara Cicerale, Paul A S Breslin, Gary K Beauchamp, Russell S J Keast. Sensory characterization of the irritant properties of oleocanthal, a natural anti-inflammatory agent in extra virgin olive oils. Chemical senses. 2009 May; 34(4):333-9. doi: 10.1093/chemse/bjp006. [PMID: 19273462]
  • Sara Cicerale, Xavier A Conlan, Neil W Barnett, Andrew J Sinclair, Russell S J Keast. Influence of heat on biological activity and concentration of oleocanthal--a natural anti-inflammatory agent in virgin olive oil. Journal of agricultural and food chemistry. 2009 Feb; 57(4):1326-30. doi: 10.1021/jf803154w. [PMID: 19166297]
  • Fabio Galvano, Luca La Fauci, Giulia Graziani, Rosalia Ferracane, Roberta Masella, Claudia Di Giacomo, Antonio Scacco, Massimo D'Archivio, Luca Vanella, Giacomo Galvano. Phenolic compounds and antioxidant activity of Italian extra virgin olive oil Monti Iblei. Journal of medicinal food. 2007 Dec; 10(4):650-6. doi: 10.1089/jmf.2007.409. [PMID: 18158836]
  • Amos B Smith, Jeffrey B Sperry, Qiang Han. Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues. The Journal of organic chemistry. 2007 Aug; 72(18):6891-900. doi: 10.1021/jo071146k. [PMID: 17685574]
  • John Impellizzeri, Jianming Lin. A simple high-performance liquid chromatography method for the determination of throat-burning oleocanthal with probated antiinflammatory activity in extra virgin olive oils. Journal of agricultural and food chemistry. 2006 May; 54(9):3204-8. doi: 10.1021/jf052870b. [PMID: 16637673]
  • Vincenzo Fogliano, Raffaele Sacchi. Oleocanthal in olive oil: between myth and reality. Molecular nutrition & food research. 2006 Jan; 50(1):5-6. doi: 10.1002/mnfr.200690002. [PMID: 16397870]
  • Amos B Smith, Qiang Han, Paul A S Breslin, Gary K Beauchamp. Synthesis and assignment of absolute configuration of (-)-oleocanthal: a potent, naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils. Organic letters. 2005 Oct; 7(22):5075-8. doi: 10.1021/ol052106a. [PMID: 16235961]
  • Gary K Beauchamp, Russell S J Keast, Diane Morel, Jianming Lin, Jana Pika, Qiang Han, Chi-Ho Lee, Amos B Smith, Paul A S Breslin. Phytochemistry: ibuprofen-like activity in extra-virgin olive oil. Nature. 2005 Sep; 437(7055):45-6. doi: 10.1038/437045a. [PMID: 16136122]