2'-Deoxymugineic acid (BioDeep_00000010739)

 

Secondary id: BioDeep_00001028542

human metabolite natural product


代谢物信息卡片


1-{3-carboxy-3-[(3-carboxy-3-hydroxypropyl)amino]propyl}azetidine-2-carboxylic acid

化学式: C12H20N2O7 (304.127)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 46.38%

分子结构信息

SMILES: O=C(O)C(O)CCNC(CCN1CCC1C(=O)O)C(=O)O
InChI: InChI=1S/C12H20N2O7/c15-9(12(20)21)1-4-13-7(10(16)17)2-5-14-6-3-8(14)11(18)19/h7-9,13,15H,1-6H2,(H,16,17)(H,18,19)(H,20,21)

描述信息

Isolated from wheat (Triticum aestivum). 2-Deoxymugineic acid is found in many foods, some of which are pot marjoram, kumquat, ginger, and pineappple sage.
2-Deoxymugineic acid is found in cereals and cereal products. 2-Deoxymugineic acid is isolated from wheat (Triticum aestivum).

同义名列表

7 个代谢物同义名

1-{3-carboxy-3-[(3-carboxy-3-hydroxypropyl)amino]propyl}azetidine-2-carboxylic acid; 1-{3-carboxy-3-[(3-carboxy-3-hydroxypropyl)amino]propyl}azetidine-2-carboxylate; (13c4)-2-Deoxymugineic acid; 2-Deoxymugineic acid; 2-Deoxymugineate; 2-Dma; 2'-Deoxymugineic acid



数据库引用编号

15 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)

18 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。

亚细胞结构定位 关联基因列表


文献列表

  • Tianqi Wang, Nanqi Wang, Qiaofang Lu, Shanshan Lang, Kunguang Wang, Lei Niu, Motofumi Suzuki, Yuanmei Zuo. The active Fe chelator proline-2'-deoxymugineic acid enhances peanut yield by improving soil Fe availability and plant Fe status. Plant, cell & environment. 2023 01; 46(1):239-250. doi: 10.1111/pce.14459. [PMID: 36207784]
  • Xin Zhang, Ke Xiao, Suzhen Li, Jie Li, Jiaxing Huang, Rumei Chen, Sen Pang, Xiaojin Zhou. Genome-wide analysis of the NAAT, DMAS, TOM, and ENA gene families in maize suggests their roles in mediating iron homeostasis. BMC plant biology. 2022 Jan; 22(1):37. doi: 10.1186/s12870-021-03422-7. [PMID: 35039017]
  • Motofumi Suzuki, Atsumi Urabe, Sayaka Sasaki, Ryo Tsugawa, Satoshi Nishio, Haruka Mukaiyama, Yoshiko Murata, Hiroshi Masuda, May Sann Aung, Akane Mera, Masaki Takeuchi, Keijo Fukushima, Michika Kanaki, Kaori Kobayashi, Yuichi Chiba, Binod Babu Shrestha, Hiromi Nakanishi, Takehiro Watanabe, Atsushi Nakayama, Hiromichi Fujino, Takanori Kobayashi, Keiji Tanino, Naoko K Nishizawa, Kosuke Namba. Development of a mugineic acid family phytosiderophore analog as an iron fertilizer. Nature communications. 2021 03; 12(1):1558. doi: 10.1038/s41467-021-21837-6. [PMID: 33692352]
  • Qian Li, Lei Chen, An Yang. The Molecular Mechanisms Underlying Iron Deficiency Responses in Rice. International journal of molecular sciences. 2019 Dec; 21(1):. doi: 10.3390/ijms21010043. [PMID: 31861687]
  • Raviraj Banakar, Ana Alvarez Fernandez, Changfu Zhu, Javier Abadia, Teresa Capell, Paul Christou. The ratio of phytosiderophores nicotianamine to deoxymugenic acid controls metal homeostasis in rice. Planta. 2019 Oct; 250(4):1339-1354. doi: 10.1007/s00425-019-03230-2. [PMID: 31278466]
  • Jing Che, Kengo Yokosho, Naoki Yamaji, Jian Feng Ma. A Vacuolar Phytosiderophore Transporter Alters Iron and Zinc Accumulation in Polished Rice Grains. Plant physiology. 2019 09; 181(1):276-288. doi: 10.1104/pp.19.00598. [PMID: 31331995]
  • Jesse T Beasley, Julien P Bonneau, Jose T Sánchez-Palacios, Laura T Moreno-Moyano, Damien L Callahan, Elad Tako, Raymond P Glahn, Enzo Lombi, Alexander A T Johnson. Metabolic engineering of bread wheat improves grain iron concentration and bioavailability. Plant biotechnology journal. 2019 08; 17(8):1514-1526. doi: 10.1111/pbi.13074. [PMID: 30623558]
  • Jesse T Beasley, Jonathan J Hart, Elad Tako, Raymond P Glahn, Alexander A T Johnson. Investigation of Nicotianamine and 2' Deoxymugineic Acid as Enhancers of Iron Bioavailability in Caco-2 Cells. Nutrients. 2019 Jun; 11(7):. doi: 10.3390/nu11071502. [PMID: 31262064]
  • Kosuke Namba, Yoshiko Murata. Organic Chemistry Research on the Mechanistic Elucidation of Iron Acquisition in Barley. Biological & pharmaceutical bulletin. 2018; 41(10):1502-1507. doi: 10.1248/bpb.b18-00070. [PMID: 30270318]
  • Raviraj Banakar, Ana Alvarez Fernandez, Pablo Díaz-Benito, Javier Abadia, Teresa Capell, Paul Christou. Phytosiderophores determine thresholds for iron and zinc accumulation in biofortified rice endosperm while inhibiting the accumulation of cadmium. Journal of experimental botany. 2017 10; 68(17):4983-4995. doi: 10.1093/jxb/erx304. [PMID: 29048564]
  • Khurram Bashir, Tomoko Nozoye, Seiji Nagasaka, Sultana Rasheed, Nanako Miyauchi, Motoaki Seki, Hiromi Nakanishi, Naoko K Nishizawa. Paralogs and mutants show that one DMA synthase functions in iron homeostasis in rice. Journal of experimental botany. 2017 03; 68(7):1785-1795. doi: 10.1093/jxb/erx065. [PMID: 28369596]
  • Jesse T Beasley, Julien P Bonneau, Alexander A T Johnson. Characterisation of the nicotianamine aminotransferase and deoxymugineic acid synthase genes essential to Strategy II iron uptake in bread wheat (Triticum aestivum L.). PloS one. 2017; 12(5):e0177061. doi: 10.1371/journal.pone.0177061. [PMID: 28475636]
  • Zhao-hua Yin, Yan Li, Chun-qing Zhang, Cui-cui Yang, Cheng-lai Wu, Xiang-pan Liu, Ming-ming Wang. Cloning and promoter activity analyses of the promoter of 2'-deoxymugineic acid (DMA) secretion channel gene YS3 in maize. Yi chuan = Hereditas. 2016 06; 38(6):560-568. doi: 10.16288/j.yczz.15-174. [PMID: 27655317]
  • Tadakatsu Yoneyama, Satoru Ishikawa, Shu Fujimaki. Route and Regulation of Zinc, Cadmium, and Iron Transport in Rice Plants (Oryza sativa L.) during Vegetative Growth and Grain Filling: Metal Transporters, Metal Speciation, Grain Cd Reduction and Zn and Fe Biofortification. International journal of molecular sciences. 2015 Aug; 16(8):19111-29. doi: 10.3390/ijms160819111. [PMID: 26287170]
  • Ryoichi Araki, Kosuke Namba, Yoshiko Murata, Jun Murata. Phytosiderophores revisited: 2'-deoxymugineic acid-mediated iron uptake triggers nitrogen assimilation in rice (Oryza sativa L.) seedlings. Plant signaling & behavior. 2015; 10(6):e1031940. doi: 10.1080/15592324.2015.1031940. [PMID: 26023724]
  • Ryoichi Araki, Kayoko Kousaka, Kosuke Namba, Yoshiko Murata, Jun Murata. 2'-Deoxymugineic acid promotes growth of rice (Oryza sativa L.) by orchestrating iron and nitrate uptake processes under high pH conditions. The Plant journal : for cell and molecular biology. 2015 Jan; 81(2):233-46. doi: 10.1111/tpj.12722. [PMID: 25393516]
  • Martin R Walter, Daniel Artner, Christian Stanetty. Synthesis of [13C4]-labeled 2'-deoxymugineic acid. Journal of labelled compounds & radiopharmaceuticals. 2014 Nov; 57(13):710-4. doi: 10.1002/jlcr.3242. [PMID: 25385205]
  • Eva Oburger, Barbara Gruber, Yvonne Schindlegger, Walter D C Schenkeveld, Stephan Hann, Stephan M Kraemer, Walter W Wenzel, Markus Puschenreiter. Root exudation of phytosiderophores from soil-grown wheat. The New phytologist. 2014 Sep; 203(4):1161-1174. doi: 10.1111/nph.12868. [PMID: 24890330]
  • Yvonne Schindlegger, Eva Oburger, Barbara Gruber, Walter D C Schenkeveld, Stephan M Kraemer, Markus Puschenreiter, Gunda Koellensperger, Stephan Hann. Accurate LC-ESI-MS/MS quantification of 2'-deoxymugineic acid in soil and root related samples employing porous graphitic carbon as stationary phase and a ¹³C₄-labeled internal standard. Electrophoresis. 2014 May; 35(9):1375-85. doi: 10.1002/elps.201300551. [PMID: 24464840]
  • Hongchun Xiong, Yusuke Kakei, Takanori Kobayashi, Xiaotong Guo, Mikio Nakazono, Hirokazu Takahashi, Hiromi Nakanishi, Hongyun Shen, Fusuo Zhang, Naoko K Nishizawa, Yuanmei Zuo. Molecular evidence for phytosiderophore-induced improvement of iron nutrition of peanut intercropped with maize in calcareous soil. Plant, cell & environment. 2013 Oct; 36(10):1888-902. doi: 10.1111/pce.12097. [PMID: 23496756]
  • Rongli Shi, Günther Weber, Jessica Köster, Mohammad Reza-Hajirezaei, Chunqin Zou, Fusuo Zhang, Nicolaus von Wirén. Senescence-induced iron mobilization in source leaves of barley (Hordeum vulgare) plants. The New phytologist. 2012 Jul; 195(2):372-383. doi: 10.1111/j.1469-8137.2012.04165.x. [PMID: 22591276]
  • Reiko Nishiyama, Mariyo Kato, Shinji Nagata, Shuichi Yanagisawa, Tadakatsu Yoneyama. Identification of Zn-nicotianamine and Fe-2'-Deoxymugineic acid in the phloem sap from rice plants (Oryza sativa L.). Plant & cell physiology. 2012 Feb; 53(2):381-90. doi: 10.1093/pcp/pcr188. [PMID: 22218421]
  • Basuki Widodo, Martin R Broadley, Terry Rose, Michael Frei, Juan Pariasca-Tanaka, Tadashi Yoshihashi, Michael Thomson, John P Hammond, Alessio Aprile, Timothy J Close, Abdelbagi M Ismail, Matthias Wissuwa. Response to zinc deficiency of two rice lines with contrasting tolerance is determined by root growth maintenance and organic acid exudation rates, and not by zinc-transporter activity. The New phytologist. 2010 Apr; 186(2):400-14. doi: 10.1111/j.1469-8137.2009.03177.x. [PMID: 20100202]
  • Yusuke Kakei, Isomaro Yamaguchi, Takanori Kobayashi, Michiko Takahashi, Hiromi Nakanishi, Takashi Yamakawa, Naoko K Nishizawa. A highly sensitive, quick and simple quantification method for nicotianamine and 2'-deoxymugineic acid from minimum samples using LC/ESI-TOF-MS achieves functional analysis of these components in plants. Plant & cell physiology. 2009 Nov; 50(11):1988-93. doi: 10.1093/pcp/pcp141. [PMID: 19880395]
  • Takahiro Aoyama, Takanori Kobayashi, Michiko Takahashi, Seiji Nagasaka, Kanako Usuda, Yusuke Kakei, Yasuhiro Ishimaru, Hiromi Nakanishi, Satoshi Mori, Naoko K Nishizawa. OsYSL18 is a rice iron(III)-deoxymugineic acid transporter specifically expressed in reproductive organs and phloem of lamina joints. Plant molecular biology. 2009 Aug; 70(6):681-92. doi: 10.1007/s11103-009-9500-3. [PMID: 19468840]
  • Haruhiko Inoue, Takanori Kobayashi, Tomoko Nozoye, Michiko Takahashi, Yusuke Kakei, Kazumasa Suzuki, Mikio Nakazono, Hiromi Nakanishi, Satoshi Mori, Naoko K Nishizawa. Rice OsYSL15 is an iron-regulated iron(III)-deoxymugineic acid transporter expressed in the roots and is essential for iron uptake in early growth of the seedlings. The Journal of biological chemistry. 2009 Feb; 284(6):3470-9. doi: 10.1074/jbc.m806042200. [PMID: 19049971]
  • Günther Weber, Nicolaus von Wirén, Heiko Hayen. Investigation of ascorbate-mediated iron release from ferric phytosiderophores in the presence of nicotianamine. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine. 2008 Oct; 21(5):503-13. doi: 10.1007/s10534-008-9137-8. [PMID: 18322653]
  • Longjun Cheng, Fang Wang, Huixia Shou, Fangliang Huang, Luqing Zheng, Fei He, Jinhui Li, Fang-Jie Zhao, Daisei Ueno, Jian Feng Ma, Ping Wu. Mutation in nicotianamine aminotransferase stimulated the Fe(II) acquisition system and led to iron accumulation in rice. Plant physiology. 2007 Dec; 145(4):1647-57. doi: 10.1104/pp.107.107912. [PMID: 17951455]
  • Yuko Ogo, Reiko Nakanishi Itai, Hiromi Nakanishi, Takanori Kobayashi, Michiko Takahashi, Satoshi Mori, Naoko K Nishizawa. The rice bHLH protein OsIRO2 is an essential regulator of the genes involved in Fe uptake under Fe-deficient conditions. The Plant journal : for cell and molecular biology. 2007 Aug; 51(3):366-77. doi: 10.1111/j.1365-313x.2007.03149.x. [PMID: 17559517]
  • Koralie A Hill, Leonard W Lion, Beth A Ahner. Reduced Cd accumulation in Zea mays: a protective role for phytosiderophores?. Environmental science & technology. 2002 Dec; 36(24):5363-8. doi: 10.1021/es020695z. [PMID: 12521162]
  • Suzanne M Reichman, David R Parker. Revisiting the metal-binding chemistry of nicotianamine and 2'-deoxymugineic acid. Implications for iron nutrition in strategy II plants. Plant physiology. 2002 Aug; 129(4):1435-8. doi: 10.1104/pp.005009. [PMID: 12177457]
  • M L Guerinot. Improving rice yields--ironing out the details. Nature biotechnology. 2001 May; 19(5):417-8. doi: 10.1038/88067. [PMID: 11329003]
  • T Kobayashi, H Nakanishi, M Takahashi, S Kawasaki, N K Nishizawa, S Mori. In vivo evidence that Ids3 from Hordeum vulgare encodes a dioxygenase that converts 2'-deoxymugineic acid to mugineic acid in transgenic rice. Planta. 2001 Apr; 212(5-6):864-71. doi: 10.1007/s004250000453. [PMID: 11346963]
  • N von Wirén, R Gibrat, J F Briat. In vitro characterization of iron-phytosiderophore interaction with maize root plasma membranes: evidences for slow association kinetics. Biochimica et biophysica acta. 1998 Apr; 1371(1):143-55. doi: 10.1016/s0005-2736(98)00022-4. [PMID: 9565671]