3,9,15-Tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone (BioDeep_00000002630)

 

Secondary id: BioDeep_00000403821

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tris(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

化学式: C45H57N3O9 (783.4094592)
中文名称: 白僵菌毒素
谱图信息: 最多检出来源 Viridiplantae(plant) 1.89%

分子结构信息

SMILES: CC(C)C1C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)O1)CC2=CC=CC=C2)C)C(C)C)CC3=CC=CC=C3)C)C(C)C)CC4=CC=CC=C4)C
InChI: InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3

描述信息

[Raw Data] CBA19_Beauvericin_pos_20eV_1-1_01_1374.txt
[Raw Data] CBA19_Beauvericin_pos_50eV_1-1_01_1485.txt
[Raw Data] CBA19_Beauvericin_pos_10eV_1-1_01_1352.txt
[Raw Data] CBA19_Beauvericin_pos_40eV_1-1_01_1376.txt
[Raw Data] CBA19_Beauvericin_pos_30eV_1-1_01_1483.txt
Beauvericin is a Fusarium mycotoxin. Beauvericin inhibits acyl-CoA: cholesterol acyltransferase (ACAT) activity with an IC50 of 3 μM in an enzyme assay using rat liver microsomes[1].
Beauvericin is a Fusarium mycotoxin. Beauvericin inhibits acyl-CoA: cholesterol acyltransferase (ACAT) activity with an IC50 of 3 μM in an enzyme assay using rat liver microsomes[1].

同义名列表

3 个代谢物同义名

3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tris(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone; 3,9,15-Tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone; Beauvericin



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(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)

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

  • Liming Hu, Xintong Sui, Xin Dong, Zhimeng Li, Shiyi Lun, Shumin Wang. Low beauvericin concentrations promote PC-12 cell survival under oxidative stress by regulating lipid metabolism and PI3K/AKT/mTOR signaling. Ecotoxicology and environmental safety. 2024 Jan; 269(?):115786. doi: 10.1016/j.ecoenv.2023.115786. [PMID: 38061083]
  • Gui Wang, Yamei Qiao, Yunyan Zhao, Yuanyuan Song, Mengyang Li, Min Jin, Dong Yang, Jing Yin, Junwen Li, Weili Liu. Beauvericin exerts an anti-tumor effect on hepatocellular carcinoma by inducing PI3K/AKT-mediated apoptosis. Archives of biochemistry and biophysics. 2023 09; 745(?):109720. doi: 10.1016/j.abb.2023.109720. [PMID: 37611353]
  • Giacomo Di Matteo, Alessandra Cimbalo, Lara Manyes, Luisa Mannina. Beauvericin Immunotoxicity Prevention by Gentiana lutea L. Flower In Vitro. Toxins. 2023 08; 15(9):. doi: 10.3390/toxins15090538. [PMID: 37755964]
  • M H G Berntssen, P G Fjeldal, P J Gavaia, V Laizé, K Hamre, C E Donald, J V Jakobsen, Å Omdal, S Søderstrøm, K K Lie. Dietary beauvericin and enniatin B exposure cause different adverse health effects in farmed Atlantic salmon. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Feb; 174(?):113648. doi: 10.1016/j.fct.2023.113648. [PMID: 36736876]
  • Sofie Søderstrøm, Liv Søfteland, Veronika Sele, Anne-Katrine Lundebye, Marc Hg Berntssen, Kai K Lie. Enniatin B and beauvericin affect intestinal cell function and hematological processes in Atlantic salmon (Salmo salar) after acute exposure. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Feb; 172(?):113557. doi: 10.1016/j.fct.2022.113557. [PMID: 36526092]
  • Geni Ye, Yubo Jiao, Lijuan Deng, Minjing Cheng, Sheng Wang, Junqiu Zhang, Jie Ouyang, Yong Li, Yuxin He, Zhengchao Tu, Zhen Wang, Xiaojuan Song, Chenran Wang, Qi Qi, Dongmei Zhang, Lei Wang, Maohua Huang, Wencai Ye, Minfeng Chen. Beauvericin suppresses the proliferation and pulmonary metastasis of osteosarcoma by selectively inhibiting TGFBR2 pathway. International journal of biological sciences. 2023; 19(14):4376-4392. doi: 10.7150/ijbs.86214. [PMID: 37781043]
  • Yu Yuan, Guangpeng Meng, Yuanbo Li, Chunjie Wu. Study on In Vitro Metabolism and In Vivo Pharmacokinetics of Beauvericin. Toxins. 2022 07; 14(7):. doi: 10.3390/toxins14070477. [PMID: 35878215]
  • Sofie Søderstrøm, Kai K Lie, Anne-Katrine Lundebye, Liv Søfteland. Beauvericin (BEA) and enniatin B (ENNB)-induced impairment of mitochondria and lysosomes - Potential sources of intracellular reactive iron triggering ferroptosis in Atlantic salmon primary hepatocytes. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Mar; 161(?):112819. doi: 10.1016/j.fct.2022.112819. [PMID: 35038498]
  • Charbel Al Khoury, Zainab Bashir, Sima Tokajian, Nabil Nemer, Georgi Merhi, Georges Nemer. In silico evidence of beauvericin antiviral activity against SARS-CoV-2. Computers in biology and medicine. 2022 02; 141(?):105171. doi: 10.1016/j.compbiomed.2021.105171. [PMID: 34968860]
  • Barbara Novak, Amanda Lopes Hasuda, Mahdi Ghanbari, Viviane Mayumi Maruo, Ana Paula F R L Bracarense, Manon Neves, Caroline Emsenhuber, Silvia Wein, Isabelle P Oswald, Philippe Pinton, Dian Schatzmayr. Effects of Fusarium metabolites beauvericin and enniatins alone or in mixture with deoxynivalenol on weaning piglets. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2021 Dec; 158(?):112719. doi: 10.1016/j.fct.2021.112719. [PMID: 34843867]
  • M Alonso-Garrido, M Frangiamone, G Font, A Cimbalo, L Manyes. In vitro blood brain barrier exposure to mycotoxins and carotenoids pumpkin extract alters mitochondrial gene expression and oxidative stress. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2021 Jul; 153(?):112261. doi: 10.1016/j.fct.2021.112261. [PMID: 34015425]
  • Ana Juan-García, Giovanni Caprioli, Gianni Sagratini, Jordi Mañes, Cristina Juan. Coffee Silverskin and Spent Coffee Suitable as Neuroprotectors against Cell Death by Beauvericin and α-Zearalenol: Evaluating Strategies of Treatment. Toxins. 2021 02; 13(2):. doi: 10.3390/toxins13020132. [PMID: 33579040]
  • Cristina Juan, Gaia de Simone, Gianni Sagratini, Giovanni Caprioli, Jordi Mañes, Ana Juan-García. Reducing the effect of beauvericin on neuroblastoma SH-SY5Y cell line by natural products. Toxicon : official journal of the International Society on Toxinology. 2020 Dec; 188(?):164-171. doi: 10.1016/j.toxicon.2020.10.017. [PMID: 33164869]
  • Domenico Montesano, Ana Juan-García, Jordi Mañes, Cristina Juan. Chemoprotective effect of carotenoids from Lycium barbarum L. on SH-SY5Y neuroblastoma cells treated with beauvericin. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Jul; 141(?):111414. doi: 10.1016/j.fct.2020.111414. [PMID: 32387444]
  • M Veronica Fumero, Alessandra Villani, Antonia Susca, Miriam Haidukowski, Maria T Cimmarusti, Christopher Toomajian, John F Leslie, Sofia N Chulze, Antonio Moretti. Fumonisin and Beauvericin Chemotypes and Genotypes of the Sister Species Fusarium subglutinans and Fusarium temperatum. Applied and environmental microbiology. 2020 06; 86(13):. doi: 10.1128/aem.00133-20. [PMID: 32358011]
  • Margot Bärenstrauch, Stéphane Mann, Chloé Jacquemin, Sarra Bibi, Oum-Kalthoum Sylla, Emmanuel Baudouin, Didier Buisson, Soizic Prado, Caroline Kunz. Molecular crosstalk between the endophyte Paraconiothyrium variabile and the phytopathogen Fusarium oxysporum - Modulation of lipoxygenase activity and beauvericin production during the interaction. Fungal genetics and biology : FG & B. 2020 06; 139(?):103383. doi: 10.1016/j.fgb.2020.103383. [PMID: 32272219]
  • Bastien Barral, Marc Chillet, Anna Doizy, Maeva Grassi, Laetitia Ragot, Mathieu Léchaudel, Noel Durand, Lindy Joy Rose, Altus Viljoen, Sabine Schorr-Galindo. Diversity and Toxigenicity of Fungi that Cause Pineapple Fruitlet Core Rot. Toxins. 2020 05; 12(5):. doi: 10.3390/toxins12050339. [PMID: 32455651]
  • Ana Juan-García, Saverio Carbone, Maissa Ben-Mahmoud, Gianni Sagratini, Jordi Mañes. Beauvericin and ochratoxin A mycotoxins individually and combined in HepG2 cells alter lipid peroxidation, levels of reactive oxygen species and glutathione. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 May; 139(?):111247. doi: 10.1016/j.fct.2020.111247. [PMID: 32165234]
  • Charbel Al Khoury, Nabil Nemer, Georges Nemer, Mazen Kurban, Charlotte Bernigaud, Katja Fischer, Jacques Guillot. In Vitro Activity of Beauvericin against All Developmental Stages of Sarcoptes scabiei. Antimicrobial agents and chemotherapy. 2020 04; 64(5):. doi: 10.1128/aac.02118-19. [PMID: 32122897]
  • Zhaojian Ding, Tianwei Xu, Weiju Zhu, Lijie Li, Qiyan Fu. A MADS-box transcription factor FoRlm1 regulates aerial hyphal growth, oxidative stress, cell wall biosynthesis and virulence in Fusarium oxysporum f. sp. cubense. Fungal biology. 2020 Mar; 124(3-4):183-193. doi: 10.1016/j.funbio.2020.02.001. [PMID: 32220379]
  • Natalia Arroyo-Manzanares, Ahmed M Hamed, Ana M García-Campaña, Laura Gámiz-Gracia. Plant-based milks: unexplored source of emerging mycotoxins. A proposal for the control of enniatins and beauvericin using UHPLC-MS/MS. Food additives & contaminants. Part B, Surveillance. 2019 Dec; 12(4):296-302. doi: 10.1080/19393210.2019.1663276. [PMID: 31791225]
  • Ana Juan-García, Domenico Montesano, Jordi Mañes, Cristina Juan. Cytoprotective effects of carotenoids-rich extract from Lycium barbarum L. on the beauvericin-induced cytotoxicity on Caco-2 cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Nov; 133(?):110798. doi: 10.1016/j.fct.2019.110798. [PMID: 31473340]
  • Karolina Gromadzka, Lidia Błaszczyk, Jerzy Chełkowski, Agnieszka Waśkiewicz. Occurrence of Mycotoxigenic Fusarium Species and Competitive Fungi on Preharvest Maize Ear Rot in Poland. Toxins. 2019 04; 11(4):. doi: 10.3390/toxins11040224. [PMID: 30991649]
  • Monika Urbaniak, Łukasz Stępień, Silvio Uhlig. Evidence for Naturally Produced Beauvericins Containing N-Methyl-Tyrosine in Hypocreales Fungi. Toxins. 2019 03; 11(3):. doi: 10.3390/toxins11030182. [PMID: 30917588]
  • Ł Stępień, K Gromadzka, J Chełkowski, A Basińska-Barczak, J Lalak-Kańczugowska. Diversity and mycotoxin production by Fusarium temperatum and Fusarium subglutinans as causal agents of pre-harvest Fusarium maize ear rot in Poland. Journal of applied genetics. 2019 Feb; 60(1):113-121. doi: 10.1007/s13353-018-0478-x. [PMID: 30430379]
  • Marlies Decleer, Sofie Landschoot, Sarah De Saeger, Andrea Rajkovic, Kris Audenaert. Impact of fungicides and weather on cyclodepsipeptide-producing Fusarium spp. and beauvericin and enniatin levels in wheat grains. Journal of the science of food and agriculture. 2019 Jan; 99(1):253-262. doi: 10.1002/jsfa.9167. [PMID: 29851099]
  • Seung Eun Lee, See-Hyoung Park, Sae Woong Oh, Ju Ah Yoo, Kitae Kwon, Se Jung Park, Jangsoon Kim, Hak Sung Lee, Jae Youl Cho, Jongsung Lee. Beauvericin inhibits melanogenesis by regulating cAMP/PKA/CREB and LXR-α/p38 MAPK-mediated pathways. Scientific reports. 2018 10; 8(1):14958. doi: 10.1038/s41598-018-33352-8. [PMID: 30297846]
  • Yanfang Sun, Michael Wink, Pan Wang, Hongfei Lu, Hongxin Zhao, Hongtao Liu, Shixian Wang, Yang Sun, Zongsuo Liang. Biological characteristics, bioactive components and antineoplastic properties of sporoderm-broken spores from wild Cordyceps cicadae. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Dec; 36(?):217-228. doi: 10.1016/j.phymed.2017.10.004. [PMID: 29157818]
  • Daniela Heilos, Yelko Rodríguez-Carrasco, Bernhard Englinger, Gerald Timelthaler, Sushilla van Schoonhoven, Michael Sulyok, Simon Boecker, Roderich D Süssmuth, Petra Heffeter, Rosa Lemmens-Gruber, Rita Dornetshuber-Fleiss, Walter Berger. The Natural Fungal Metabolite Beauvericin Exerts Anticancer Activity In Vivo: A Pre-Clinical Pilot Study. Toxins. 2017 08; 9(9):. doi: 10.3390/toxins9090258. [PMID: 28837057]
  • Beatriz Mallebrera, Annalisa Maietti, Paola Tedeschi, Guillermina Font, Maria-Jose Ruiz, Vincenzo Brandolini. Antioxidant capacity of trans-resveratrol dietary supplements alone or combined with the mycotoxin beauvericin. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 Jul; 105(?):315-318. doi: 10.1016/j.fct.2017.04.027. [PMID: 28450129]
  • Vania C Liuzzi, Valentina Mirabelli, Maria Teresa Cimmarusti, Miriam Haidukowski, John F Leslie, Antonio F Logrieco, Rocco Caliandro, Francesca Fanelli, Giuseppina Mulè. Enniatin and Beauvericin Biosynthesis in Fusarium Species: Production Profiles and Structural Determinant Prediction. Toxins. 2017 01; 9(2):. doi: 10.3390/toxins9020045. [PMID: 28125067]
  • Lien Taevernier, Nathalie Bracke, Lieselotte Veryser, Evelien Wynendaele, Bert Gevaert, Kathelijne Peremans, Bart De Spiegeleer. Blood-brain barrier transport kinetics of the cyclic depsipeptide mycotoxins beauvericin and enniatins. Toxicology letters. 2016 Sep; 258(?):175-184. doi: 10.1016/j.toxlet.2016.06.1741. [PMID: 27349679]
  • Pierre Hellin, Géraldine Dedeurwaerder, Maxime Duvivier, Jonathan Scauflaire, Bart Huybrechts, Alfons Callebaut, Françoise Munaut, Anne Legrève. Relationship between Fusarium spp. diversity and mycotoxin contents of mature grains in southern Belgium. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2016 Jul; 33(7):1228-40. doi: 10.1080/19440049.2016.1185900. [PMID: 27181458]
  • Veli Hietaniemi, Sari Rämö, Tapani Yli-Mattila, Marika Jestoi, Sari Peltonen, Mirja Kartio, Elina Sieviläinen, Tauno Koivisto, Päivi Parikka. Updated survey of Fusarium species and toxins in Finnish cereal grains. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2016 May; 33(5):831-48. doi: 10.1080/19440049.2016.1162112. [PMID: 27002810]
  • Yelko Rodríguez-Carrasco, Daniela Heilos, Lennart Richter, Roderich D Süssmuth, Petra Heffeter, Michael Sulyok, Lukas Kenner, Walter Berger, Rita Dornetshuber-Fleiss. Mouse tissue distribution and persistence of the food-born fusariotoxins Enniatin B and Beauvericin. Toxicology letters. 2016 Apr; 247(?):35-44. doi: 10.1016/j.toxlet.2016.02.008. [PMID: 26892719]
  • Ana Belén Serrano, Anna Laura Capriotti, Chiara Cavaliere, Susy Piovesana, Roberto Samperi, Salvatore Ventura, Aldo Laganà. Development of a Rapid LC-MS/MS Method for the Determination of Emerging Fusarium mycotoxins Enniatins and Beauvericin in Human Biological Fluids. Toxins. 2015 Sep; 7(9):3554-71. doi: 10.3390/toxins7093554. [PMID: 26371043]
  • B Mallebrera, V Brandolini, G Font, M J Ruiz. Cytoprotective effect of resveratrol diastereomers in CHO-K1 cells exposed to beauvericin. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2015 Jun; 80(?):319-327. doi: 10.1016/j.fct.2015.03.028. [PMID: 25843362]
  • Cormac McElhinney, Pádraig O'Kiely, Chris Elliott, Martin Danaher. Development and validation of an UHPLC-MS/MS method for the determination of mycotoxins in grass silages. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2015; 32(12):2101-12. doi: 10.1080/19440049.2015.1094830. [PMID: 26374621]
  • Zhaojian Ding, Minhui Li, Fei Sun, Pinggen Xi, Longhua Sun, Lianhui Zhang, Zide Jiang. Mitogen-activated protein kinases are associated with the regulation of physiological traits and virulence in Fusarium oxysporum f. sp. cubense. PloS one. 2015; 10(4):e0122634. doi: 10.1371/journal.pone.0122634. [PMID: 25849862]
  • Ling Hu, Michael Rychlik. Occurrence of enniatins and beauvericin in 60 Chinese medicinal herbs. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2014; 31(7):1240-5. doi: 10.1080/19440049.2014.913813. [PMID: 24720681]
  • A Prosperini, A Juan-García, G Font, M J Ruiz. Beauvericin-induced cytotoxicity via ROS production and mitochondrial damage in Caco-2 cells. Toxicology letters. 2013 Oct; 222(2):204-11. doi: 10.1016/j.toxlet.2013.07.005. [PMID: 23850777]
  • G Meca, T Zhou, X Z Li, A Ritieni, J Mañes. Ciclohexadespipeptide beauvericin degradation by different strains of Saccharomyces cerevisiae. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Sep; 59(?):334-8. doi: 10.1016/j.fct.2013.06.010. [PMID: 23791659]
  • Łukasz Stępień, Grzegorz Koczyk, Agnieszka Waśkiewicz. Diversity of Fusarium species and mycotoxins contaminating pineapple. Journal of applied genetics. 2013 Aug; 54(3):367-80. doi: 10.1007/s13353-013-0146-0. [PMID: 23572446]
  • Mathias Devreese, Siegrid De Baere, Patrick De Backer, Siska Croubels. Quantitative determination of the Fusarium mycotoxins beauvericin, enniatin A, A1, B and B1 in pig plasma using high performance liquid chromatography-tandem mass spectrometry. Talanta. 2013 Mar; 106(?):212-9. doi: 10.1016/j.talanta.2012.11.068. [PMID: 23598119]
  • Lukasz Stępień, Agnieszka Waśkiewicz. Sequence divergence of the enniatin synthase gene in relation to production of beauvericin and enniatins in Fusarium species. Toxins. 2013 Mar; 5(3):537-55. doi: 10.3390/toxins5030537. [PMID: 23486233]
  • Manuel S López-Berges, Concepción Hera, Michael Sulyok, Katja Schäfer, Javier Capilla, Josep Guarro, Antonio Di Pietro. The velvet complex governs mycotoxin production and virulence of Fusarium oxysporum on plant and mammalian hosts. Molecular microbiology. 2013 Jan; 87(1):49-65. doi: 10.1111/mmi.12082. [PMID: 23106229]
  • Chunyu Li, Cunwu Zuo, Guiming Deng, Ruibin Kuang, Qiaosong Yang, Chunhua Hu, Ou Sheng, Sheng Zhang, Lijun Ma, Yuerong Wei, Jing Yang, Siwen Liu, Manosh Kumar Biswas, Altus Viljoen, Ganjun Yi. Contamination of bananas with beauvericin and fusaric acid produced by Fusarium oxysporum f. sp. cubense. PloS one. 2013; 8(7):e70226. doi: 10.1371/journal.pone.0070226. [PMID: 23922960]
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  • Li-Jian Xu, Yuan-Shuai Liu, Li-Gang Zhou, Jian-Yong Wu. Modeling of Fusarium redolens Dzf2 mycelial growth kinetics and optimal fed-batch fermentation for beauvericin production. Journal of industrial microbiology & biotechnology. 2011 Sep; 38(9):1187-92. doi: 10.1007/s10295-010-0895-2. [PMID: 21082211]
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