Brassinin (BioDeep_00000017410)

 

Secondary id: BioDeep_00000618387

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


CARBAMODITHIOIC ACID, N-(1H-INDOL-3-YLMETHYL)-, METHYL ESTER

化学式: C11H12N2S2 (236.04418719999998)
中文名称: 芸苔宁
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 9.76%

分子结构信息

SMILES: CSC(=S)NCC1=CNC2=C1C=CC=C2
InChI: InChI=1S/C11H12N2S2/c1-15-11(14)13-7-8-6-12-10-5-3-2-4-9(8)10/h2-6,12H,7H2,1H3,(H,13,14)

描述信息

Isolated from Chinese cabbage (Brassica campestris sspecies pekinensis)(Cruciferae) heads inoculated with Pseudomonas cichorii. Brassinin is found in cauliflower, chinese cabbage, and brassicas.
Brassinin is a dithiocarbamic ester and an indole phytoalexin.
Brassinin is a natural product found in Pseudomonas cichorii, Brassica juncea, and other organisms with data available.
Brassinin is found in brassicas. Brassinin is isolated from Chinese cabbage (Brassica campestris ssp. pekinensis)(Cruciferae) heads inoculated with Pseudomonas cichorii.

同义名列表

24 个代谢物同义名

CARBAMODITHIOIC ACID, N-(1H-INDOL-3-YLMETHYL)-, METHYL ESTER; Methyl hydrogen [(1H-indol-3-yl)methyl]carbonodithioimidate; Carbamodithioic acid,N-(1H-indol-3-ylmethyl)-,methyl ester; Carbamodithioic acid, (1H-indol-3-ylmethyl)-, methyl ester; N-[(1H-indol-3-yl)methyl](methylsulfanyl)carbothioamide; Brassinine;Methyl (1H-indol-3-ylmethyl)carbamodithioate; 1H-(Indol-3-ylmethyl)-dithiocarbamic acid,methyl ester; N-(1H-indol-3-ylmethyl)(methylsulfanyl)carbothioamide; Methyl (1H-indol-3-ylmethyl)carbamodithioate, 9CI; Methyl (1H-indol-3-ylmethyl)dithiocarbamic acid; methyl N-(1H-indol-3-ylmethyl)-carbamodithioate; methyl N-(1H-indol-3-ylmethyl)carbamodithioate; methyl ((1H-indol-3-yl)methyl)carbamodithioate; methyl (1H-indol-3-yl)methylcarbamodithioate; Methyl (1H-indol-3-ylmethyl)carbamodithioate; methyl (1H-indol-3-ylmethyl)dithiocarbamate; Brassinin, >=98\\% (HPLC); UNII-J2IBO1B8VH; Brassinin, 1; SMP2_000288; J2IBO1B8VH; Brassinine; Brassinin; BSN



数据库引用编号

13 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)

7 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

  • Bobin Kang, Chae Young Kim, Jisu Hwang, Hyung Joo Suh, Hyeon-Son Choi. Brassinin, a phytoalexin in cruciferous vegetables, suppresses obesity-induced inflammatory responses through the Nrf2-HO-1 signaling pathway in an adipocyte-macrophage co-culture system. Phytotherapy research : PTR. 2019 May; 33(5):1426-1437. doi: 10.1002/ptr.6333. [PMID: 30848529]
  • M Soledade C Pedras, Abbas Abdoli, Vijay K Sarma-Mamillapalle. Inhibitors of the Detoxifying Enzyme of the Phytoalexin Brassinin Based on Quinoline and Isoquinoline Scaffolds. Molecules (Basel, Switzerland). 2017 Aug; 22(8):. doi: 10.3390/molecules22081345. [PMID: 28805743]
  • Andrew P Klein, Elizabeth S Sattely. Biosynthesis of cabbage phytoalexins from indole glucosinolate. Proceedings of the National Academy of Sciences of the United States of America. 2017 02; 114(8):1910-1915. doi: 10.1073/pnas.1615625114. [PMID: 28154137]
  • Akhil Srivastava, Il Kyu Cho, Yangrae Cho. The Bdtf1 gene in Alternaria brassicicola is important in detoxifying brassinin and maintaining virulence on Brassica species. Molecular plant-microbe interactions : MPMI. 2013 Dec; 26(12):1429-40. doi: 10.1094/mpmi-07-13-0186-r. [PMID: 23945003]
  • M Soledade C Pedras, Abbas Abdoli, Paulos B Chumala, Pijus Saha, Gabriele Schatte. Unprecedented spirocyclization of 3-methyleneindoline-2-thiones during hydrolysis of the phytoalexin cyclobrassinin. Bioorganic & medicinal chemistry letters. 2013 Jan; 23(2):484-7. doi: 10.1016/j.bmcl.2012.11.042. [PMID: 23232058]
  • M Soledade C Pedras, Vijay K Sarma-Mamillapalle. Metabolism and metabolites of dithiocarbamates in the plant pathogenic fungus Leptosphaeria maculans. Journal of agricultural and food chemistry. 2012 Aug; 60(32):7792-8. doi: 10.1021/jf302038a. [PMID: 22823278]
  • M Soledade C Pedras, Zoran Minic. Differential protein expression in response to the phytoalexin brassinin allows the identification of molecular targets in the phytopathogenic fungus Alternaria brassicicola. Molecular plant pathology. 2012 Jun; 13(5):483-93. doi: 10.1111/j.1364-3703.2011.00765.x. [PMID: 22111639]
  • William W Li, Vincent W Li, Michelle Hutnik, Albert S Chiou. Tumor angiogenesis as a target for dietary cancer prevention. Journal of oncology. 2012; 2012(?):879623. doi: 10.1155/2012/879623. [PMID: 21977033]
  • M Soledade C Pedras, Zoran Minic, Sajjad Hossain. Discovery of inhibitors and substrates of brassinin hydrolase: Probing selectivity with dithiocarbamate bioisosteres. Bioorganic & medicinal chemistry. 2012 Jan; 20(1):225-33. doi: 10.1016/j.bmc.2011.11.009. [PMID: 22137599]
  • Marcel Jenny, Angela Wondrak, Elissaveta Zvetkova, Nguyen Thi Ngoc Tram, Phan Thi Phi Phi, Harald Schennach, Zoran Culig, Florian Ueberall, Dietmar Fuchs. Crinum latifolium leave extracts suppress immune activation cascades in peripheral blood mononuclear cells and proliferation of prostate tumor cells. Scientia pharmaceutica. 2011 Apr; 79(2):323-35. doi: 10.3797/scipharm.1011-13. [PMID: 21773069]
  • M Soledade C Pedras, Sajjad Hossain, Ryan B Snitynsky. Detoxification of cruciferous phytoalexins in Botrytis cinerea: spontaneous dimerization of a camalexin metabolite. Phytochemistry. 2011 Feb; 72(2-3):199-206. doi: 10.1016/j.phytochem.2010.11.018. [PMID: 21176925]
  • Aymeric Joubert, Nelly Bataille-Simoneau, Claire Campion, Thomas Guillemette, Piétrick Hudhomme, Béatrice Iacomi-Vasilescu, Thibault Leroy, Stéphanie Pochon, Pascal Poupard, Philippe Simoneau. Cell wall integrity and high osmolarity glycerol pathways are required for adaptation of Alternaria brassicicola to cell wall stress caused by brassicaceous indolic phytoalexins. Cellular microbiology. 2011 Jan; 13(1):62-80. doi: 10.1111/j.1462-5822.2010.01520.x. [PMID: 20812995]
  • M Soledade C Pedras, Estifanos E Yaya, Sajjad Hossain. Unveiling the phytoalexin biosynthetic puzzle in salt cress: unprecedented incorporation of glucobrassicin into wasalexins A and B. Organic & biomolecular chemistry. 2010 Nov; 8(22):5150-8. doi: 10.1039/c0ob00265h. [PMID: 20848032]
  • M Soledade C Pedras, Zoran Minic, Vijay K Sarma-Mamillapalle, Mojmir Suchy. Discovery of inhibitors of brassinin oxidase based on the scaffolds of the phytoalexins brassilexin and wasalexin. Bioorganic & medicinal chemistry. 2010 Apr; 18(7):2456-63. doi: 10.1016/j.bmc.2010.02.054. [PMID: 20303277]
  • Heather C Rowe, Daniel J Kliebenstein. All mold is not alike: the importance of intraspecific diversity in necrotrophic plant pathogens. PLoS pathogens. 2010 Mar; 6(3):e1000759. doi: 10.1371/journal.ppat.1000759. [PMID: 20361052]
  • Yves A Millet, Cristian H Danna, Nicole K Clay, Wisuwat Songnuan, Matthew D Simon, Danièle Werck-Reichhart, Frederick M Ausubel. Innate immune responses activated in Arabidopsis roots by microbe-associated molecular patterns. The Plant cell. 2010 Mar; 22(3):973-90. doi: 10.1105/tpc.109.069658. [PMID: 20348432]
  • M Soledade C Pedras, Zoran Minic, Vijay K Sarma-Mamillapalle. Substrate specificity and inhibition of brassinin hydrolases, detoxifying enzymes from the plant pathogens Leptosphaeria maculans and Alternaria brassicicola. The FEBS journal. 2009 Dec; 276(24):7412-28. doi: 10.1111/j.1742-4658.2009.07457.x. [PMID: 19922473]
  • Rocío González-Lamothe, Gabriel Mitchell, Mariza Gattuso, Moussa S Diarra, François Malouin, Kamal Bouarab. Plant antimicrobial agents and their effects on plant and human pathogens. International journal of molecular sciences. 2009 Jul; 10(8):3400-3419. doi: 10.3390/ijms10083400. [PMID: 20111686]
  • M Soledade C Pedras, Zoran Minic, Vijay K Sarma-Mamillapalle. Synthetic inhibitors of the fungal detoxifying enzyme brassinin oxidase based on the phytoalexin camalexin scaffold. Journal of agricultural and food chemistry. 2009 Mar; 57(6):2429-35. doi: 10.1021/jf803666s. [PMID: 19243099]
  • Adrienne C Sexton, Zoran Minic, Anton J Cozijnsen, M Soledade C Pedras, Barbara J Howlett. Cloning, purification and characterisation of brassinin glucosyltransferase, a phytoalexin-detoxifying enzyme from the plant pathogen Sclerotinia sclerotiorum. Fungal genetics and biology : FG & B. 2009 Feb; 46(2):201-9. doi: 10.1016/j.fgb.2008.10.014. [PMID: 19041410]
  • M Soledade C Pedras, Paulos B Chumala, Wei Jin, Mohammed S Islam, Dominic W Hauck. The phytopathogenic fungus Alternaria brassicicola: phytotoxin production and phytoalexin elicitation. Phytochemistry. 2009 Feb; 70(3):394-402. doi: 10.1016/j.phytochem.2009.01.005. [PMID: 19223049]
  • M S C Pedras, Zoran Minic, Mukund Jha. Brassinin oxidase, a fungal detoxifying enzyme to overcome a plant defense -- purification, characterization and inhibition. The FEBS journal. 2008 Jul; 275(14):3691-705. doi: 10.1111/j.1742-4658.2008.06513.x. [PMID: 18549452]
  • M Soledade C Pedras, Mukund Jha, Zoran Minic, Oladapo G Okeola. Isosteric probes provide structural requirements essential for detoxification of the phytoalexin brassinin by the fungal pathogen Leptosphaeria maculans. Bioorganic & medicinal chemistry. 2007 Sep; 15(18):6054-61. doi: 10.1016/j.bmc.2007.06.040. [PMID: 17616463]
  • M Soledade C Pedras, Mohammad Hossain. Design, synthesis, and evaluation of potential inhibitors of brassinin glucosyltransferase, a phytoalexin detoxifying enzyme from Sclerotinia sclerotiorum. Bioorganic & medicinal chemistry. 2007 Sep; 15(17):5981-96. doi: 10.1016/j.bmc.2007.05.072. [PMID: 17590338]
  • M Soledade C Pedras, Ravi S Gadagi, Mukund Jha, Vijay K Sarma-Mamillapalle. Detoxification of the phytoalexin brassinin by isolates of Leptosphaeria maculans pathogenic on brown mustard involves an inducible hydrolase. Phytochemistry. 2007 Jun; 68(11):1572-8. doi: 10.1016/j.phytochem.2007.03.020. [PMID: 17467751]
  • Slávka Bekesová, Vladimír Kovácik, Igor Tvaroska, Zuzana Curillová, L'udovít Skultéty, Pavel Rehulka. Elimination of isocyanate and isothiocyanate molecules at the electrospray ionization ion trap, electrospray ionization quadrupole time-of-flight and matrix-assisted laser desorption/ionization time-of-flight tandem mass spectrometry fragmentation of sodium cationized brassitin, brassinin and their glycosides. European journal of mass spectrometry (Chichester, England). 2007; 13(2):147-54. doi: 10.1255/ejms.847. [PMID: 17881781]
  • M Soledade C Pedras, Mukund Jha. Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin. Bioorganic & medicinal chemistry. 2006 Jul; 14(14):4958-79. doi: 10.1016/j.bmc.2006.03.014. [PMID: 16616505]
  • M Soledade C Pedras, Mukund Jha, Oladapo G Okeola. Camalexin induces detoxification of the phytoalexin brassinin in the plant pathogen Leptosphaeria maculans. Phytochemistry. 2005 Nov; 66(22):2609-16. doi: 10.1016/j.phytochem.2005.09.013. [PMID: 16266734]
  • Balakrishnan Venkatesh, Ursula Hettwer, Birger Koopmann, Petr Karlovsky. Conversion of cDNA differential display results (DDRT-PCR) into quantitative transcription profiles. BMC genomics. 2005 Apr; 6(?):51. doi: 10.1186/1471-2164-6-51. [PMID: 15807902]
  • M Pilátová, M Sarisský, P Kutschy, A Mirossay, R Mezencev, Z Curillová, M Suchý, K Monde, L Mirossay, J Mojzis. Cruciferous phytoalexins: antiproliferative effects in T-Jurkat leukemic cells. Leukemia research. 2005 Apr; 29(4):415-21. doi: 10.1016/j.leukres.2004.09.003. [PMID: 15725476]
  • M Soledade C Pedras, Pearson W K Ahiahonu, Mohammad Hossain. Detoxification of the cruciferous phytoalexin brassinin in Sclerotinia sclerotiorum requires an inducible glucosyltransferase. Phytochemistry. 2004 Oct; 65(19):2685-94. doi: 10.1016/j.phytochem.2004.08.033. [PMID: 15464156]
  • A Douglas Kinghorn, Bao-Ning Su, Dae Sik Jang, Leng Chee Chang, Dongho Lee, Jian-Qiao Gu, Esperanza J Carcache-Blanco, Alison D Pawlus, Sang Kook Lee, Eun Jung Park, Muriel Cuendet, Joell J Gills, Krishna Bhat, Hye-Sung Park, Eugenia Mata-Greenwood, Lynda L Song, Meishiang Jang, John M Pezzuto. Natural inhibitors of carcinogenesis. Planta medica. 2004 Aug; 70(8):691-705. doi: 10.1055/s-2004-827198. [PMID: 15326546]
  • M Soledade C Pedras, Sabine Montaut, Mojmir Suchy. Phytoalexins from the crucifer rutabaga: structures, syntheses, biosyntheses, and antifungal activity. The Journal of organic chemistry. 2004 Jun; 69(13):4471-6. doi: 10.1021/jo049648a. [PMID: 15202903]
  • Joanna Ruszkowska, Jerzy T Wróbel. Tryptophan-derived sulfur-containing phytoalexins--a general overview. Advances in experimental medicine and biology. 2003; 527(?):629-36. doi: 10.1007/978-1-4615-0135-0_72. [PMID: 15206782]
  • R Mezencev, J Mojzis, M Pilatova, P Kutschy. Antiproliferative and cancer chemopreventive activity of phytoalexins: focus on indole phytoalexins from crucifers. Neoplasma. 2003; 50(4):239-45. doi: . [PMID: 12937834]
  • Rajendra G Mehta, John M Pezzuto. Discovery of cancer preventive agents from natural products: from plants to prevention. Current oncology reports. 2002 Nov; 4(6):478-86. doi: 10.1007/s11912-002-0059-2. [PMID: 12354359]
  • M Soledade C Pedras, Corwin M Nycholat, Sabine Montaut, Yiming Xu, Abdul Q Khan. Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Phytochemistry. 2002 Mar; 59(6):611-25. doi: 10.1016/s0031-9422(02)00026-2. [PMID: 11867093]
  • Eun Jung Park, John M Pezzuto. Botanicals in cancer chemoprevention. Cancer metastasis reviews. 2002; 21(3-4):231-55. doi: 10.1023/a:1021254725842. [PMID: 12549763]
  • K S Gellatly, G J Ash, J L Taylor. Development of a method for mRNA differential display in filamentous fungi: comparison of mRNA differential display reverse transcription polymerase chain reaction and cDNA amplified fragment length polymorphism in Leptosphaeria maculans. Canadian journal of microbiology. 2001 Oct; 47(10):955-60. doi: 10.1139/w01-100. [PMID: 11718550]
  • M S Pedras, S Montaut, Y Xu, A Q Khan, A Loukaci. Assembling the biosynthetic puzzle of crucifer metabolites: indole-3-acetaldoxime is incorporated efficiently into phytoalexins but glucobrassicin is not. Chemical communications (Cambridge, England). 2001 Sep; ?(17):1572-3. doi: 10.1039/b103442c. [PMID: 12240387]
  • M S Pedras, F I Okanga. Strategies of cruciferous pathogenic fungi: detoxification of the phytoalexin cyclobrassinin by mimicry. Journal of agricultural and food chemistry. 1999 Mar; 47(3):1196-202. doi: 10.1021/jf980854r. [PMID: 10552437]
  • M S Pedras, A Loukaci, F I Okanga. The cruciferous phytoalexins brassinin and cyclobrassinin are intermediates in the biosynthesis of brassilexin. Bioorganic & medicinal chemistry letters. 1998 Nov; 8(21):3037-8. doi: 10.1016/s0960-894x(98)00564-2. [PMID: 9873671]
  • R G Mehta, J Liu, A Constantinou, M Hawthorne, J M Pezzuto, R C Moon, R M Moriarty. Structure-activity relationships of brassinin in preventing the development of carcinogen-induced mammary lesions in organ culture. Anticancer research. 1994 May; 14(3A):1209-13. doi: ". [PMID: 8074474]