Thaxtomin A (BioDeep_00000412274)
natural product
代谢物信息卡片
Thaxtomin A
化学式: C22H22N4O6 (438.1539272)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CN1C(C(=O)N(C(C1=O)(CC2=CC(=CC=C2)O)O)C)CC3=CNC4=C3C(=CC=C4)[N+](=O)[O-]
InChI: InChI=1S/C22H22N4O6/c1-24-18(10-14-12-23-16-7-4-8-17(19(14)16)26(31)32)20(28)25(2)22(30,21(24)29)11-13-5-3-6-15(27)9-13/h3-9,12,18,23,27,30H,10-11H2,1-2H3/t18-,22+/m0/s1
数据库引用编号
9 个数据库交叉引用编号
- PubChem: 180098
- ChEMBL: CHEMBL2270642
- CAS: 122380-18-1
- MoNA: CCMSLIB00005724275
- MoNA: CCMSLIB00005724274
- MoNA: CCMSLIB00005724284
- MoNA: CCMSLIB00005723290
- MoNA: CCMSLIB00005723291
- MoNA: CCMSLIB00005723298
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)
0 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
- Corrie V Vincent, Dawn R D Bignell. Regulation of virulence mechanisms in plant-pathogenic Streptomyces.
Canadian journal of microbiology.
2024 Jun; 70(6):199-212. doi:
10.1139/cjm-2023-0171. [PMID: 38190652] - Chloe Casey, Thomas Köcher, Clément Champion, Katharina Jandrasits, Magdalena Mosiolek, Clémence Bonnot, Liam Dolan. Reduced coenzyme Q synthesis confers non-target site resistance to the herbicide thaxtomin A.
PLoS genetics.
2023 01; 19(1):e1010423. doi:
10.1371/journal.pgen.1010423. [PMID: 36608112] - Christopher R Clarke, Charles G Kramer, Raghavendhar R Kotha, Devanand L Luthria. The Phytotoxin Thaxtomin A Is the Primary Virulence Determinant for Scab Disease of Beet, Carrot, and Radish Caused by Streptomyces scabiei.
Phytopathology.
2022 Nov; 112(11):2288-2295. doi:
10.1094/phyto-03-22-0072-r. [PMID: 35694886] - Lu Liu, Liaoyang Hao, Ning Liu, Yonglong Zhao, Naiqin Zhong, Pan Zhao. iTRAQ-Based Proteomics Analysis of Response to Solanum tuberosum Leaves Treated with the Plant Phytotoxin Thaxtomin A.
International journal of molecular sciences.
2021 Nov; 22(21):. doi:
10.3390/ijms222112036. [PMID: 34769466] - Nathalie Beaudoin, Iauhenia Isayenka, Audrey Ducharme, Sophie Massie, André Gagnon, Richard Hogue, Carole Beaulieu, Dominique Michaud. Habituation to thaxtomin A increases resistance to common scab in 'Russet Burbank' potato.
PloS one.
2021; 16(6):e0253414. doi:
10.1371/journal.pone.0253414. [PMID: 34133457] - Fatima Awwad, Guillaume Bertrand, Michel Grandbois, Nathalie Beaudoin. Auxin protects Arabidopsis thaliana cell suspension cultures from programmed cell death induced by the cellulose biosynthesis inhibitors thaxtomin A and isoxaben.
BMC plant biology.
2019 Nov; 19(1):512. doi:
10.1186/s12870-019-2130-2. [PMID: 31752698] - Yuting Li, Jingyu Liu, Damilola Adekunle, Luke Bown, Kapil Tahlan, Dawn R D Bignell. TxtH is a key component of the thaxtomin biosynthetic machinery in the potato common scab pathogen Streptomyces scabies.
Molecular plant pathology.
2019 10; 20(10):1379-1393. doi:
10.1111/mpp.12843. [PMID: 31282068] - María Inés Lapaz, Andrés López, José Carlos Huguet-Tapia, Martín Fabián Pérez-Baldassari, Cesar Iglesias, Rosemary Loria, Guillermo Moyna, María Julia Pianzzola. Isolation and structural characterization of a non-diketopiperazine phytotoxin from a potato pathogenic Streptomyces strain.
Natural product research.
2019 Oct; 33(20):2951-2957. doi:
10.1080/14786419.2018.1511554. [PMID: 30304960] - Sören Planckaert, Samuel Jourdan, Isolde M Francis, Benoit Deflandre, Sébastien Rigali, Bart Devreese. Proteomic Response to Thaxtomin Phytotoxin Elicitor Cellobiose and to Deletion of Cellulose Utilization Regulator CebR in Streptomyces scabies.
Journal of proteome research.
2018 11; 17(11):3837-3852. doi:
10.1021/acs.jproteome.8b00528. [PMID: 30229651] - L Lin, X Xu, Y Zheng, C Zhang. Effects of AttM lactonase on the pathogenicity of Streptomyces scabies.
Letters in applied microbiology.
2018 Sep; 67(3):270-277. doi:
10.1111/lam.13019. [PMID: 29897616] - Shachi Joglekar, Mohamed Suliman, Michael Bartsch, Vivek Halder, Jens Maintz, Jaqueline Bautor, Jürgen Zeier, Jane E Parker, Erich Kombrink. Chemical Activation of EDS1/PAD4 Signaling Leading to Pathogen Resistance in Arabidopsis.
Plant & cell physiology.
2018 Aug; 59(8):1592-1607. doi:
10.1093/pcp/pcy106. [PMID: 29931201] - Yucheng Zhang, Guangde Jiang, Yousong Ding, Rosemary Loria. Genetic background affects pathogenicity island function and pathogen emergence in Streptomyces.
Molecular plant pathology.
2018 07; 19(7):1733-1741. doi:
10.1111/mpp.12656. [PMID: 29316196] - Michael Winn, Daniel Francis, Jason Micklefield. De novo Biosynthesis of 'Non-Natural' Thaxtomin Phytotoxins.
Angewandte Chemie (International ed. in English).
2018 06; 57(23):6830-6833. doi:
10.1002/anie.201801525. [PMID: 29603527] - Guangde Jiang, Yucheng Zhang, Magan M Powell, Peilan Zhang, Ran Zuo, Yi Zhang, Dimitris Kallifidas, Albert M Tieu, Hendrik Luesch, Rosemary Loria, Yousong Ding. High-Yield Production of Herbicidal Thaxtomins and Thaxtomin Analogs in a Nonpathogenic Streptomyces Strain.
Applied and environmental microbiology.
2018 06; 84(11):. doi:
10.1128/aem.00164-18. [PMID: 29602787] - Yucheng Zhang, Rosemary Loria. Emergence of Novel Pathogenic Streptomyces Species by Site-Specific Accretion and cis-Mobilization of Pathogenicity Islands.
Molecular plant-microbe interactions : MPMI.
2017 01; 30(1):72-82. doi:
10.1094/mpmi-09-16-0190-r. [PMID: 27977935] - Yucheng Zhang, Dawn R D Bignell, Ran Zuo, Qiurong Fan, Jose C Huguet-Tapia, Yousong Ding, Rosemary Loria. Promiscuous Pathogenicity Islands and Phylogeny of Pathogenic Streptomyces spp.
Molecular plant-microbe interactions : MPMI.
2016 08; 29(8):640-50. doi:
10.1094/mpmi-04-16-0068-r. [PMID: 27502745] - Samuel Jourdan, Isolde Maria Francis, Min Jung Kim, Joren Jeico C Salazar, Sören Planckaert, Jean-Marie Frère, André Matagne, Frédéric Kerff, Bart Devreese, Rosemary Loria, Sébastien Rigali. The CebE/MsiK Transporter is a Doorway to the Cello-oligosaccharide-mediated Induction of Streptomyces scabies Pathogenicity.
Scientific reports.
2016 06; 6(?):27144. doi:
10.1038/srep27144. [PMID: 27250236] - Robert S Tegg, Sergey Shabala, Tracey A Cuin, Calum R Wilson. Mechanisms of thaxtomin A-induced root toxicity revealed by a thaxtomin A sensitive Arabidopsis mutant (ucu2-2/gi-2).
Plant cell reports.
2016 Feb; 35(2):347-56. doi:
10.1007/s00299-015-1888-4. [PMID: 26518425] - Joanna K Fyans, Luke Bown, Dawn R D Bignell. Isolation and Characterization of Plant-Pathogenic Streptomyces Species Associated with Common Scab-Infected Potato Tubers in Newfoundland.
Phytopathology.
2016 Feb; 106(2):123-31. doi:
10.1094/phyto-05-15-0125-r. [PMID: 26524546] - Tanya Arseneault, Claudia Goyer, Martin Filion. Pseudomonas fluorescens LBUM223 Increases Potato Yield and Reduces Common Scab Symptoms in the Field.
Phytopathology.
2015 Oct; 105(10):1311-7. doi:
10.1094/phyto-12-14-0358-r. [PMID: 25961336] - Hongbo Zhang, Qingpeng Wang, Xin Ning, Hang Hang, Jing Ma, Xiande Yang, Xiaolin Lu, Jiabao Zhang, Yonghong Li, Congwei Niu, Haoran Song, Xin Wang, Peng George Wang. Synthesis and biological evaluations of a series of thaxtomin analogues.
Journal of agricultural and food chemistry.
2015 Apr; 63(14):3734-41. doi:
10.1021/jf506153t. [PMID: 25804187] - Isolde M Francis, Samuel Jourdan, Steven Fanara, Rosemary Loria, Sébastien Rigali. The cellobiose sensor CebR is the gatekeeper of Streptomyces scabies pathogenicity.
mBio.
2015 Feb; 6(2):e02018. doi:
10.1128/mbio.02018-14. [PMID: 25714708] - Dawn R D Bignell, Isolde M Francis, Joanna K Fyans, Rosemary Loria. Thaxtomin A production and virulence are controlled by several bld gene global regulators in Streptomyces scabies.
Molecular plant-microbe interactions : MPMI.
2014 Aug; 27(8):875-85. doi:
10.1094/mpmi-02-14-0037-r. [PMID: 24678834] - D R D Bignell, J K Fyans, Z Cheng. Phytotoxins produced by plant pathogenic Streptomyces species.
Journal of applied microbiology.
2014 Feb; 116(2):223-35. doi:
10.1111/jam.12369. [PMID: 24131731] - Robert S Tegg, Sergey N Shabala, Tracey A Cuin, Noel W Davies, Calum R Wilson. Enhanced resistance to the cellulose biosynthetic inhibitors, thaxtomin A and isoxaben in Arabidopsis thaliana mutants, also provides specific co-resistance to the auxin transport inhibitor, 1-NPA.
BMC plant biology.
2013 May; 13(?):76. doi:
10.1186/1471-2229-13-76. [PMID: 23638731] - Lan Lin, Hui Ming Ge, Tong Yan, Yan Hua Qin, Ren Xiang Tan. Thaxtomin A-deficient endophytic Streptomyces sp. enhances plant disease resistance to pathogenic Streptomyces scabies.
Planta.
2012 Dec; 236(6):1849-61. doi:
10.1007/s00425-012-1741-8. [PMID: 22922880] - Sarah M Barry, Johan A Kers, Evan G Johnson, Lijiang Song, Philip R Aston, Bhumit Patel, Stuart B Krasnoff, Brian R Crane, Donna M Gibson, Rosemary Loria, Gregory L Challis. Cytochrome P450–catalyzed L-tryptophan nitration in thaxtomin phytotoxin biosynthesis.
Nature chemical biology.
2012 Oct; 8(10):814-6. doi:
10.1038/nchembio.1048. [PMID: 22941045] - Sylvain Lerat, Martin Forest, Annie Lauzier, Gilles Grondin, Serge Lacelle, Carole Beaulieu. Potato suberin induces differentiation and secondary metabolism in the genus Streptomyces.
Microbes and environments.
2012; 27(1):36-42. doi:
10.1264/jsme2.me11282. [PMID: 22129602] - Geneviève S Legault, Sylvain Lerat, Philippe Nicolas, Carole Beaulieu. Tryptophan regulates thaxtomin A and indole-3-acetic acid production in Streptomyces scabiei and modifies its interactions with radish seedlings.
Phytopathology.
2011 Sep; 101(9):1045-51. doi:
10.1094/phyto-03-11-0064. [PMID: 21521002] - Alison L Dann, Calum R Wilson. Comparative assessment of genetic and epigenetic variation among regenerants of potato (Solanum tuberosum) derived from long-term nodal tissue-culture and cell selection.
Plant cell reports.
2011 Apr; 30(4):631-9. doi:
10.1007/s00299-010-0983-9. [PMID: 21210276] - Renée St-Onge, Vijay J Gadkar, Tanya Arseneault, Claudia Goyer, Martin Filion. The ability of Pseudomonas sp. LBUM 223 to produce phenazine-1-carboxylic acid affects the growth of Streptomyces scabies, the expression of thaxtomin biosynthesis genes and the biological control potential against common scab of potato.
FEMS microbiology ecology.
2011 Jan; 75(1):173-83. doi:
10.1111/j.1574-6941.2010.00992.x. [PMID: 21073487] - Viviane Brochu, Marie Girard-Martel, Isabelle Duval, Sylvain Lerat, Gilles Grondin, Olivier Domingue, Carole Beaulieu, Nathalie Beaudoin. Habituation to thaxtomin A in hybrid poplar cell suspensions provides enhanced and durable resistance to inhibitors of cellulose synthesis.
BMC plant biology.
2010 Dec; 10(?):272. doi:
10.1186/1471-2229-10-272. [PMID: 21143977] - Calum R Wilson, Robert S Tegg, Annabel J Wilson, Gregory A Luckman, Alieta Eyles, Zi Qing Yuan, Leon H Hingston, Anthony J Conner. Stable and extreme resistance to common scab of potato obtained through somatic cell selection.
Phytopathology.
2010 May; 100(5):460-7. doi:
10.1094/phyto-100-5-0460. [PMID: 20373967] - Sylvain Lerat, Anne-Marie Simao-Beaunoir, Run Wu, Nathalie Beaudoin, Carole Beaulieu. Involvement of the plant polymer Suberin and the disaccharide cellobiose in triggering thaxtomin A biosynthesis, a phytotoxin produced by the pathogenic agent streptomyces scabies.
Phytopathology.
2010 Jan; 100(1):91-6. doi:
10.1094/phyto-100-1-0091. [PMID: 19968554] - Sylvain Lerat, Amadou H Babana, Mohamed El Oirdi, Abdelbassed El Hadrami, Fouad Daayf, Nathalie Beaudoin, Kamal Bouarab, Carole Beaulieu. Streptomyces scabiei and its toxin thaxtomin A induce scopoletin biosynthesis in tobacco and Arabidopsis thaliana.
Plant cell reports.
2009 Dec; 28(12):1895-903. doi:
10.1007/s00299-009-0792-1. [PMID: 19859716] - Evan G Johnson, Stuart B Krasnoff, Dawn R D Bignell, Wen-Chuan Chung, Tao Tao, Ronald J Parry, Rosemary Loria, Donna M Gibson. 4-Nitrotryptophan is a substrate for the non-ribosomal peptide synthetase TxtB in the thaxtomin A biosynthetic pathway.
Molecular microbiology.
2009 Aug; 73(3):409-18. doi:
10.1111/j.1365-2958.2009.06780.x. [PMID: 19570136] - Isabelle Duval, Nathalie Beaudoin. Transcriptional profiling in response to inhibition of cellulose synthesis by thaxtomin A and isoxaben in Arabidopsis thaliana suspension cells.
Plant cell reports.
2009 May; 28(5):811-30. doi:
10.1007/s00299-009-0670-x. [PMID: 19198845] - Russell R King, Larry A Calhoun. The thaxtomin phytotoxins: sources, synthesis, biosynthesis, biotransformation and biological activity.
Phytochemistry.
2009 May; 70(7):833-41. doi:
10.1016/j.phytochem.2009.04.013. [PMID: 19467551] - Volker Bischoff, Sarah Jane Cookson, Shuang Wu, Wolf-Rüdiger Scheible. Thaxtomin A affects CESA-complex density, expression of cell wall genes, cell wall composition, and causes ectopic lignification in Arabidopsis thaliana seedlings.
Journal of experimental botany.
2009; 60(3):955-65. doi:
10.1093/jxb/ern344. [PMID: 19269997] - Rosemary Loria, Dawn R D Bignell, Simon Moll, José C Huguet-Tapia, Madhumita V Joshi, Evan G Johnson, Ryan F Seipke, Donna M Gibson. Thaxtomin biosynthesis: the path to plant pathogenicity in the genus Streptomyces.
Antonie van Leeuwenhoek.
2008 Jun; 94(1):3-10. doi:
10.1007/s10482-008-9240-4. [PMID: 18392685] - R Errakhi, A Dauphin, P Meimoun, A Lehner, D Reboutier, P Vatsa, J Briand, K Madiona, J P Rona, M Barakate, D Wendehenne, C Beaulieu, F Bouteau. An early Ca2+ influx is a prerequisite to thaxtomin A-induced cell death in Arabidopsis thaliana cells.
Journal of experimental botany.
2008; 59(15):4259-70. doi:
10.1093/jxb/ern267. [PMID: 19015217] - Michael J Wach, Stuart B Krasnoff, Rosemary Loria, Donna M Gibson. Effect of carbohydrates on the production of thaxtomin A by Streptomyces acidiscabies.
Archives of microbiology.
2007 Jul; 188(1):81-8. doi:
10.1007/s00203-007-0225-x. [PMID: 17340119] - Lea H Hiltunen, Into Laakso, Vladimír Chobot, Kati S Hakala, Anja Weckman, Jari P T Valkonen. Influence of thaxtomins in different combinations and concentrations on growth of micropropagated potato shoot cultures.
Journal of agricultural and food chemistry.
2006 May; 54(9):3372-9. doi:
10.1021/jf060270m. [PMID: 16637698] - Stuart B Krasnoff, Emil B Lobkovsky, Michael J Wach, Rosemary Loria, Donna M Gibson. Chemistry and phytotoxicity of thaxtomin A alkyl ethers.
Journal of agricultural and food chemistry.
2005 Nov; 53(24):9446-51. doi:
10.1021/jf051614w. [PMID: 16302760] - Isabelle Duval, Viviane Brochu, Mathieu Simard, Carole Beaulieu, Nathalie Beaudoin. Thaxtomin A induces programmed cell death in Arabidopsis thaliana suspension-cultured cells.
Planta.
2005 Nov; 222(5):820-31. doi:
10.1007/s00425-005-0016-z. [PMID: 16025344] - Robert Steven Tegg, Lolita Melian, Calum Rae Wilson, Sergey Shabala. Plant cell growth and ion flux responses to the streptomycete phytotoxin thaxtomin A: calcium and hydrogen flux patterns revealed by the non-invasive MIFE technique.
Plant & cell physiology.
2005 Apr; 46(4):638-48. doi:
10.1093/pcp/pci069. [PMID: 15753107] - Michael J Wach, Johan A Kers, Stuart B Krasnoff, Rosemary Loria, Donna M Gibson. Nitric oxide synthase inhibitors and nitric oxide donors modulate the biosynthesis of thaxtomin A, a nitrated phytotoxin produced by Streptomyces spp.
Nitric oxide : biology and chemistry.
2005 Feb; 12(1):46-53. doi:
10.1016/j.niox.2004.11.004. [PMID: 15631947] - Julie Beauséjour, Carole Beaulieu. Characterization of Streptomyces scabies mutants deficient in melanin biosynthesis.
Canadian journal of microbiology.
2004 Sep; 50(9):705-9. doi:
10.1139/w04-043. [PMID: 15644924] - Johan A Kers, Michael J Wach, Stuart B Krasnoff, Joanne Widom, Kimberly D Cameron, Raghida A Bukhalid, Donna M Gibson, Brian R Crane, Rosemary Loria. Nitration of a peptide phytotoxin by bacterial nitric oxide synthase.
Nature.
2004 May; 429(6987):79-82. doi:
10.1038/nature02504. [PMID: 15129284] - Wolf-Rüdiger Scheible, Barbara Fry, Andrej Kochevenko, Dana Schindelasch, Laurent Zimmerli, Shauna Somerville, Rosemary Loria, Chris R Somerville. An Arabidopsis mutant resistant to thaxtomin A, a cellulose synthesis inhibitor from Streptomyces species.
The Plant cell.
2003 Aug; 15(8):1781-94. doi:
10.1105/tpc.013342. [PMID: 12897252] - Annie Lauzier, Claudia Goyer, Luc Ruest, Ryszard Brzezinski, Don L Crawford, Carole Beaulieu. Effect of amino acids on thaxtomin A biosynthesis by Streptomyces scabies.
Canadian journal of microbiology.
2002 Apr; 48(4):359-64. doi:
10.1139/w02-031. [PMID: 12030709] - R A Bukhalid, T Takeuchi, D Labeda, Rosemary Loria. Horizontal transfer of the plant virulence gene, nec1, and flanking sequences among genetically distinct Streptomyces strains in the Diastatochromogenes cluster.
Applied and environmental microbiology.
2002 Feb; 68(2):738-44. doi:
10.1128/aem.68.2.738-744.2002. [PMID: 11823214] - R R King, C H Lawrence, J A Gray. Herbicidal properties of the thaxtomin group of phytotoxins.
Journal of agricultural and food chemistry.
2001 May; 49(5):2298-301. doi:
10.1021/jf0012998. [PMID: 11368592] - el-S A el-Sayed. Production of thaxtomin a by two species of Streptomyces causing potato scab.
Acta microbiologica et immunologica Hungarica.
2001; 48(1):67-79. doi:
10.1556/amicr.48.2001.1.7. [PMID: 11233701] - L Tóth, M Maeda, F Tanaka, K Kobayashi. Isolation and identification of pathogenic strains of Streptomyces acidiscabies from netted scab lesions of potato tubers in Hokkaido (Japan).
Acta microbiologica et immunologica Hungarica.
2001; 48(3-4):575-85. doi:
10.1556/amicr.48.2001.3-4.21. [PMID: 11791352] - F G Healy, M Wach, S B Krasnoff, D M Gibson, R Loria. The txtAB genes of the plant pathogen Streptomyces acidiscabies encode a peptide synthetase required for phytotoxin thaxtomin A production and pathogenicity.
Molecular microbiology.
2000 Nov; 38(4):794-804. doi:
10.1046/j.1365-2958.2000.02170.x. [PMID: 11115114] - R R King, C H Lawrence, L A Calhoun. Microbial glucosylation of thaxtomin A, a partial detoxification.
Journal of agricultural and food chemistry.
2000 Feb; 48(2):512-4. doi:
10.1021/jf990912o. [PMID: 10691667] - E S el-Sayed. Production of thaxtomin A by two species of Streptomyces causing potato scab.
Folia microbiologica.
2000; 45(5):415-22. doi:
10.1007/bf02817614. [PMID: 11357862]