Sinapine (BioDeep_00000398006)

Main id: BioDeep_00000000492

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


Sinapoylcholine

化学式: [C16H24NO5]+ (310.16543939999997)
中文名称: 芥子碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C[N+](C)(C)CCOC(=O)/C=C/C1=CC(=C(C(=C1)OC)O)OC
InChI: InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1

描述信息

Acquisition and generation of the data is financially supported by the Max-Planck-Society
IPB_RECORD: 2601; CONFIDENCE confident structure
Sinapine is an alkaloid isolated from seeds of the cruciferous species. Sinapine exhibits anti-inflammatory, anti-oxidant, anti-tumor, anti-angiogenic and radio-protective effects. Sinapine is also an acetylcholinesterase (AChE) inhibitor and can be used for the research of Alzheimer’s disease, ataxia, myasthenia gravis, and Parkinson’s disease[1][2][3][4].
Sinapine is an alkaloid isolated from seeds of the cruciferous species. Sinapine exhibits anti-inflammatory, anti-oxidant, anti-tumor, anti-angiogenic and radio-protective effects. Sinapine is also an acetylcholinesterase (AChE) inhibitor and can be used for the research of Alzheimer’s disease, ataxia, myasthenia gravis, and Parkinson’s disease[1][2][3][4].

同义名列表

2 个代谢物同义名

Sinapoylcholine; Sinapine



数据库引用编号

22 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)

13 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

  • Simeng Chu, Fukui Shen, Wenjuan Liu, Jin Zhang, Xiaoying Wang, Min Jiang, Gang Bai. Sinapine targeting PLCβ3 EF hands disrupts Gαq-PLCβ3 interaction and ameliorates cardiovascular diseases. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Apr; 126(?):155200. doi: 10.1016/j.phymed.2023.155200. [PMID: 38387273]
  • Jian-Li Huang, Yi-Hua Xu, Xin-Wei Yang, Jie Wang, Yu Zhu, Xian-Bo Wu. Jiawei guomin decoction regulates the degranulation of mast cells in atopic dermatitis mice via the HIS/PAR-2 pathway. Journal of ethnopharmacology. 2024 Mar; 321(?):117485. doi: 10.1016/j.jep.2023.117485. [PMID: 38008276]
  • Ying Huang, Xueqin Gao, Yang An, Ping Zeng, Changming Chen, Wukai Ma, Xueming Yao. Inhibitory Effect of Jinwujiangu Prescription on Peripheral Blood Osteoclasts in Patients with Rheumatoid Arthritis and the Relevant Molecular Mechanism. Mediators of inflammation. 2023; 2023(?):4814412. doi: 10.1155/2023/4814412. [PMID: 36816744]
  • Yufei Feng, Shuyuan Chang, Zhongxu Jing, Haibo Jiang, Yuwei Liu, Guozhao Qin. Transdermal delivery of sinapine thiocyanate by gelatin microspheres and hyaluronic acid microneedles for allergic asthma in guinea pigs. International journal of pharmaceutics. 2022 Jul; 623(?):121899. doi: 10.1016/j.ijpharm.2022.121899. [PMID: 35710072]
  • Min Shao, Qi Jiang, Chao Shen, Zhong Liu, Lihong Qiu. Sinapine induced ferroptosis in non-small cell lung cancer cells by upregulating transferrin/transferrin receptor and downregulating SLC7A11. Gene. 2022 Jun; 827(?):146460. doi: 10.1016/j.gene.2022.146460. [PMID: 35358657]
  • Guillaume N Menard, Mollie Langdon, Rupam Kumar Bhunia, Aishwarya R Shankhapal, Clarice Noleto-Dias, Charlotte Lomax, Jane L Ward, Smita Kurup, Peter J Eastmond. Diverting phenylpropanoid pathway flux from sinapine to produce industrially useful 4-vinyl derivatives of hydroxycinnamic acids in Brassicaceous oilseeds. Metabolic engineering. 2022 03; 70(?):196-205. doi: 10.1016/j.ymben.2022.01.016. [PMID: 35121114]
  • Huida Guan, Qiyan Lin, Chao Ma, Zhengcai Ju, Changhong Wang. Metabolic profiling and pharmacokinetic studies of sinapine thiocyanate by UHPLC-Q/TOF-MS and UHPLC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2022 Jan; 207(?):114431. doi: 10.1016/j.jpba.2021.114431. [PMID: 34710728]
  • Hera Nadeem, Pieter Malan, Amir Khan, Mohd Asif, Mansoor Ahmad Siddiqui, Simon Tuhafeni Angombe, Faheem Ahmad. New insights on the utilization of ultrasonicated mustard seed cake: chemical composition and antagonistic potential for root-knot nematode, Meloidogyne javanica. Journal of Zhejiang University. Science. B. 2021 Jul; 22(7):563-574. doi: 10.1631/jzus.b2000746. [PMID: 34269009]
  • Atsuhiro Iguchi, Shigesaburo Ogawa, Yukihiro Yamamoto, Setsuko Hara. Facile Preparation of Purified Sinapate Ethyl Ester from Rapeseed Meal Extracts Using Cation-exchange Resin in Dual Role as Adsorber and Catalyst. Journal of oleo science. 2021 Jul; 70(7):1007-1012. doi: 10.5650/jos.ess21036. [PMID: 34121031]
  • Hong Chen, Ling Peng, Marta Pérez de Nanclares, Michaela P Trudeau, Dan Yao, Zaixing Cheng, Pedro E Urriola, Liv Torunn Mydland, Gerald C Shurson, Margareth Overland, Chi Chen. Identification of Sinapine-Derived Choline from a Rapeseed Diet as a Source of Serum Trimethylamine N-Oxide in Pigs. Journal of agricultural and food chemistry. 2019 Jul; 67(27):7748-7754. doi: 10.1021/acs.jafc.9b02950. [PMID: 31203621]
  • Kyari Yates, Franziska Pohl, Maike Busch, Annika Mozer, Louis Watters, Andrey Shiryaev, Paul Kong Thoo Lin. Determination of sinapine in rapeseed pomace extract: Its antioxidant and acetylcholinesterase inhibition properties. Food chemistry. 2019 Mar; 276(?):768-775. doi: 10.1016/j.foodchem.2018.10.045. [PMID: 30409660]
  • Zhen Zhang, Xia Xiang, Jianbin Shi, Fenghong Huang, Xiaoyang Xia, Mingming Zheng, Ling Han, Hu Tang. A cationic conjugated polymer and graphene oxide: Application to amplified fluorescence detection of sinapine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2018 Oct; 203(?):370-374. doi: 10.1016/j.saa.2018.05.110. [PMID: 29886167]
  • Xia Xiang, Ling Han, Zhen Zhang, Fenghong Huang. Graphene oxide-based fluorescent sensor for sensitive turn-on detection of sinapine. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2017 Mar; 174(?):75-79. doi: 10.1016/j.saa.2016.11.025. [PMID: 27886646]
  • Sachin Kajla, Arundhati Mukhopadhyay, Akshay K Pradhan. Development of transgenic Brassica juncea lines for reduced seed sinapine content by perturbing phenylpropanoid pathway genes. PloS one. 2017; 12(8):e0182747. doi: 10.1371/journal.pone.0182747. [PMID: 28787461]
  • Karina Hettwer, Christoph Böttcher, Andrej Frolov, Juliane Mittasch, Andreas Albert, Edda von Roepenack-Lahaye, Dieter Strack, Carsten Milkowski. Dynamic metabolic changes in seeds and seedlings of Brassica napus (oilseed rape) suppressing UGT84A9 reveal plasticity and molecular regulation of the phenylpropanoid pathway. Phytochemistry. 2016 Apr; 124(?):46-57. doi: 10.1016/j.phytochem.2016.01.014. [PMID: 26833384]
  • Yanzhou Zhang, Xunhang Li, Zhikui Hao, Ruchun Xi, Yujie Cai, Xiangru Liao. Hydrogen Peroxide-Resistant CotA and YjqC of Bacillus altitudinis Spores Are a Promising Biocatalyst for Catalyzing Reduction of Sinapic Acid and Sinapine in Rapeseed Meal. PloS one. 2016; 11(6):e0158351. doi: 10.1371/journal.pone.0158351. [PMID: 27362423]
  • Yuxin An, Xia Li, Huanmei Sun, Wenhai Bian, Zijian Li, Youyi Zhang, Xinfeng Zhao, Xiaohui Zheng. Target-directed screening of the bioactive compounds specifically binding to β₂-adrenoceptor in Semen brassicae by high-performance affinity chromatography. Journal of molecular recognition : JMR. 2015 Oct; 28(10):628-34. doi: 10.1002/jmr.2478. [PMID: 25982051]
  • Yanxing Niu, Mulan Jiang, Mian Guo, Chuyun Wan, Shuangxi Hu, Hu Jin, Fenghong Huang. Characterization of the factors that influence sinapine concentration in rapeseed meal during fermentation. PloS one. 2015; 10(1):e0116470. doi: 10.1371/journal.pone.0116470. [PMID: 25606856]
  • Stefania Colombini, Glen A Broderick, Incoronata Galasso, Tommaso Martinelli, Luca Rapetti, Roberto Russo, Remo Reggiani. Evaluation of Camelina sativa (L.) Crantz meal as an alternative protein source in ruminant rations. Journal of the science of food and agriculture. 2014 Mar; 94(4):736-43. doi: 10.1002/jsfa.6408. [PMID: 24105894]
  • Juliane Mittasch, Christoph Böttcher, Andrej Frolov, Dieter Strack, Carsten Milkowski. Reprogramming the phenylpropanoid metabolism in seeds of oilseed rape by suppressing the orthologs of reduced epidermal fluorescence1. Plant physiology. 2013 Apr; 161(4):1656-69. doi: 10.1104/pp.113.215491. [PMID: 23424250]
  • Jeremiah Dubie, Aaron Stancik, Matthew Morra, Caleb Nindo. Antioxidant extraction from mustard (Brassica juncea) seed meal using high-intensity ultrasound. Journal of food science. 2013 Apr; 78(4):E542-8. doi: 10.1111/1750-3841.12085. [PMID: 23488824]
  • Gian Carlo Tenore, Jacopo Troisi, Raffaele Di Fiore, Adriana Basile, Ettore Novellino. Chemical composition, antioxidant and antimicrobial properties of Rapa Catozza Napoletana (Brassica rapa L. var. rapa DC.) seed meal, a promising protein source of Campania region (southern Italy) horticultural germplasm. Journal of the science of food and agriculture. 2012 Jun; 92(8):1716-24. doi: 10.1002/jsfa.5537. [PMID: 22173690]
  • Hans-Joachim Harloff, Susanne Lemcke, Juliane Mittasch, Andrej Frolov, Jian Guo Wu, Felix Dreyer, Gunhild Leckband, Christian Jung. A mutation screening platform for rapeseed (Brassica napus L.) and the detection of sinapine biosynthesis mutants. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2012 Mar; 124(5):957-69. doi: 10.1007/s00122-011-1760-z. [PMID: 22198204]
  • Jingjing Fang, Michael Reichelt, William Hidalgo, Sara Agnolet, Bernd Schneider. Tissue-specific distribution of secondary metabolites in rapeseed (Brassica napus L.). PloS one. 2012; 7(10):e48006. doi: 10.1371/journal.pone.0048006. [PMID: 23133539]
  • Dejuan Huang, Liping Luo, Cuicui Jiang, Jing Han, Jiang Wang, Tingting Zhang, Jie Jiang, Zhiquan Zhou, Huanwen Chen. Sinapine detection in radish taproot using surface desorption atmospheric pressure chemical ionization mass spectrometry. Journal of agricultural and food chemistry. 2011 Mar; 59(6):2148-56. doi: 10.1021/jf103725f. [PMID: 21332204]
  • Kathleen Clauss, Edda von Roepenack-Lahaye, Christoph Böttcher, Mary R Roth, Ruth Welti, Alexander Erban, Joachim Kopka, Dierk Scheel, Carsten Milkowski, Dieter Strack. Overexpression of sinapine esterase BnSCE3 in oilseed rape seeds triggers global changes in seed metabolism. Plant physiology. 2011 Mar; 155(3):1127-45. doi: 10.1104/pp.110.169821. [PMID: 21248075]
  • Jun Huang, Kevin Rozwadowski, V S Bhinu, Ulrike Schäfer, Abdelali Hannoufa. Manipulation of sinapine, choline and betaine accumulation in Arabidopsis seed: towards improving the nutritional value of the meal and enhancing the seedling performance under environmental stresses in oilseed crops. Plant physiology and biochemistry : PPB. 2008 Jul; 46(7):647-654. doi: 10.1016/j.plaphy.2008.04.014. [PMID: 18515127]
  • Samija Amar, Wolfgang Ecke, Heiko C Becker, Christian Möllers. QTL for phytosterol and sinapate ester content in Brassica napus L. collocate with the two erucic acid genes. TAG. Theoretical and applied genetics. Theoretische und angewandte Genetik. 2008 May; 116(8):1051-61. doi: 10.1007/s00122-008-0734-2. [PMID: 18335203]
  • Ling He, Hai-Tao Li, Sheng-Wei Guo, Li-Fang Liu, Jia-Bin Qiu, Fu Li, Bao-Chang Cai. [Inhibitory effects of sinapine on activity of acetylcholinesterase in cerebral homogenate and blood serum of rats]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Apr; 33(7):813-5. doi: . [PMID: 18589789]
  • Kathleen Clauss, Alfred Baumert, Manfred Nimtz, Carsten Milkowski, Dieter Strack. Role of a GDSL lipase-like protein as sinapine esterase in Brassicaceae. The Plant journal : for cell and molecular biology. 2008 Mar; 53(5):802-13. doi: 10.1111/j.1365-313x.2007.03374.x. [PMID: 18036206]
  • Diana Weier, Juliane Mittasch, Dieter Strack, Carsten Milkowski. The genes BnSCT1 and BnSCT2 from Brassica napus encoding the final enzyme of sinapine biosynthesis: molecular characterization and suppression. Planta. 2008 Jan; 227(2):375-85. doi: 10.1007/s00425-007-0624-x. [PMID: 17882453]
  • Lifang Liu, Yuxin Wang, Haiyan Li, Ying Ji. [Study of distribution of sinapine in commonly used crude drugs from cruciferous plants]. Se pu = Chinese journal of chromatography. 2006 Jan; 24(1):49-51. doi: ". [PMID: 16827311]
  • R N Bennett, T Wenke, B Freudenberg, F A Mellon, J Ludwig-Müller. The tu8 mutation of Arabidopsis thaliana encoding a heterochromatin protein 1 homolog causes defects in the induction of secondary metabolite biosynthesis. Plant biology (Stuttgart, Germany). 2005 Jul; 7(4):348-57. doi: 10.1055/s-2005-837634. [PMID: 16025407]
  • Hui Zhou, Yinxi Huang, Tomonori Hoshi, Yoshitomo Kashiwagi, Jun-Ichi Anzai, Genxi Li. Electrochemistry of sinapine and its detection in medicinal plants. Analytical and bioanalytical chemistry. 2005 Jun; 382(4):1196-201. doi: 10.1007/s00216-005-3241-1. [PMID: 15906009]
  • Carsten Milkowski, Alfred Baumert, Diana Schmidt, Lilian Nehlin, Dieter Strack. Molecular regulation of sinapate ester metabolism in Brassica napus: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation. The Plant journal : for cell and molecular biology. 2004 Apr; 38(1):80-92. doi: 10.1111/j.1365-313x.2004.02036.x. [PMID: 15053762]
  • B Matthäus. Antioxidant activity of extracts obtained from residues of different oilseeds. Journal of agricultural and food chemistry. 2002 Jun; 50(12):3444-52. doi: 10.1021/jf011440s. [PMID: 12033809]
  • R B Nair, R W Joy, E Kurylo, X Shi, J Schnaider, R S Datla, W A Keller, G Selvaraj. Identification of a CYP84 family of cytochrome P450-dependent mono-oxygenase genes in Brassica napus and perturbation of their expression for engineering sinapine reduction in the seeds. Plant physiology. 2000 Aug; 123(4):1623-34. doi: 10.1104/pp.123.4.1623. [PMID: 10938378]
  • Q Li, F Q Guo, R Q Gu. [Radiation protection effects of sinapine on Drosophila melanogaster in a sex-linked recessive lethal test system]. Shi yan sheng wu xue bao. 1993 Sep; 26(3):269-74. doi: . [PMID: 8191802]
  • G R Fenwick. The assessment of a new protein source--rapeseed. The Proceedings of the Nutrition Society. 1982 Sep; 41(3):277-88. doi: 10.1079/pns19820043. [PMID: 6294671]
  • E Josefsson, B Uppström. Influence of sinapine and p-hydroxybenzylglucosinolate on the nutritional value of rapeseed and white mustard meals. Journal of the science of food and agriculture. 1976 May; 27(5):438-42. doi: 10.1002/jsfa.2740270509. [PMID: 131880]