Senecionine (BioDeep_00000000416)

 

Secondary id: BioDeep_00000171859, BioDeep_00000395565

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-

化学式: C18H25NO5 (335.173264)
中文名称: 千里光宁, 千里光碱
谱图信息: 最多检出来源 Homo sapiens(feces) 0.07%

分子结构信息

SMILES: C/C=C\1/C[C@@H](C)[C@](C)(C(=O)OCC2=CCN3CC[C@H]([C@@H]23)OC1=O)O
InChI: InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3

描述信息

Senecionine is a pyrrolizidine alkaloid isolated from the plant species of the genus Senecio. It has a role as a plant metabolite. It is a lactone, a pyrrolizidine alkaloid and a tertiary alcohol. It is functionally related to a senecionan. It is a conjugate base of a senecionine(1+).
Senecionine is a natural product found in Dorobaea pimpinellifolia, Crotalaria micans, and other organisms with data available.
Senecionine is an organic compound with the chemical formula C18H25NO5. It is classified as a pyrrolizidine alkaloid.
See also: Petasites hybridus root (part of); Tussilago farfara flower (part of); Tussilago farfara leaf (part of).
A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.
D000970 - Antineoplastic Agents
Annotation level-1
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2251
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 122
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 102
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 142
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 152
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 162
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 172
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 132
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 112
[Raw Data] CB082a_Senecionine_pos_40eV_CB000034.txt
[Raw Data] CB082a_Senecionine_pos_10eV_CB000034.txt
[Raw Data] CB082a_Senecionine_pos_30eV_CB000034.txt
[Raw Data] CB082a_Senecionine_pos_20eV_CB000034.txt
[Raw Data] CB082a_Senecionine_pos_50eV_CB000034.txt
Senecionine (Senecionan-11,16-dione, 12-hydroxy-) is a pyrrolizidine alkaloid could be isolated from Senecio vulgaris. Senecionine decreases the activities of glutathione S-transferase, aminopyrine demethylase and arylhydrocarbon hydroxylase (AHH)[1][2][3].
Senecionine (Senecionan-11,16-dione, 12-hydroxy-) is a pyrrolizidine alkaloid could be isolated from Senecio vulgaris. Senecionine decreases the activities of glutathione S-transferase, aminopyrine demethylase and arylhydrocarbon hydroxylase (AHH)[1][2][3].

同义名列表

28 个代谢物同义名

(1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-; [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-; [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione,3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-,(3Z,5R,6R,14aR,14bR)-; (5R,6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione; (1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione; WLN: T55-12- 1A Q EN IOVY OVO BUTJ KU2 M1 NQ N1; WLN: T55-12-1A Q EN IOVY OVO BUTJ KU2 M NQ N; (Z)-ethylidene-hydroxy-dimethyl-[?]dione; Senecionan-11,16-dione, 12-hydroxy-; Senecionine, analytical standard; 12-Hydroxysenecionan-11,16-dione; Senecionine, >=95.0\\% (GC); Senecionan-11, 12-hydroxy-; senecionine citrate (1:1); senecionine, (15E)-isomer; senecionine citratre; SENECIONINE [MI]; (-)-SENECIONINE; UNII-BO6N1U5YG6; intergerrimine; integerrimine; Senecionine; squalidine; BO6N1U5YG6; Senecionin; AI3-51771; 1ST40300; Aureine



数据库引用编号

99 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)

99 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

  • Rui-Kun Zhang, Kun Yan, Hai-Feng Chen, Yang Zhang, Gui-Jin Li, Xiao-Gang Chen, Lin-Pu Ge, Feng Cheng, Zhi-Neng Chen, Xin-Miao Yao. Anti-osteoporotic drugs affect the pathogenesis of gut microbiota and its metabolites: a clinical study. Frontiers in cellular and infection microbiology. 2023; 13(?):1091083. doi: 10.3389/fcimb.2023.1091083. [PMID: 37475958]
  • Yan Chen, Wei-Qian Wang, Xia-Li Jia, Chang-Hong Wang, Li Yang, Zheng-Tao Wang, Ai-Zhen Xiong. Firm evidence for the detoxification of senecionine-induced hepatotoxicity via N-glucuronidation in UGT1A4-humanized transgenic mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Jul; 165(?):113185. doi: 10.1016/j.fct.2022.113185. [PMID: 35636643]
  • Weiqian Wang, Yan Chen, Yue Yin, Xunjiang Wang, Xuanling Ye, Kaiyuan Jiang, Yi Zhang, Jiwei Zhang, Wei Zhang, Yuzheng Zhuge, Li Chen, Chao Peng, Aizhen Xiong, Li Yang, Zhengtao Wang. A TMT-based shotgun proteomics uncovers overexpression of thrombospondin 1 as a contributor in pyrrolizidine alkaloid-induced hepatic sinusoidal obstruction syndrome. Archives of toxicology. 2022 07; 96(7):2003-2019. doi: 10.1007/s00204-022-03281-7. [PMID: 35357534]
  • Kai-Yuan Jiang, Yi Zhang, Xuan-Ling Ye, Fen Xiong, Yan Chen, Xia-Li Jia, Yi-Xin Zhang, Li Yang, Ai-Zhen Xiong, Zheng-Tao Wang. Bear bile powder attenuates senecionine-induced hepatic sinusoidal obstruction syndrome in mice. Chinese journal of natural medicines. 2022 Apr; 20(4):270-281. doi: 10.1016/s1875-5364(22)60169-9. [PMID: 35487597]
  • Danyan Qiu, Yizhi Ye, Mingjing Ke, Nuohan Xu, Zhenyan Zhang, Fan Zhang, Jian Kang, Yitian Yu, Tao Lu, Haifeng Qian. Effects of chiral herbicide dichlorprop on Arabidopsis thaliana metabolic profile and its implications for microbial communities in the phyllosphere. Environmental science and pollution research international. 2022 Apr; 29(19):28256-28266. doi: 10.1007/s11356-021-17936-y. [PMID: 34988791]
  • Anne-Margarethe Enge, Florian Kaltner, Christoph Gottschalk, Angelina Kin, Michael Kirstgen, Joachim Geyer, Anja These, Helen Hammer, Oliver Pötz, Albert Braeuning, Stefanie Hessel-Pras. Organic Cation Transporter I and Na+ /taurocholate Co-Transporting Polypeptide are Involved in Retrorsine- and Senecionine-Induced Hepatotoxicity in HepaRG cells. Molecular nutrition & food research. 2022 01; 66(2):e2100800. doi: 10.1002/mnfr.202100800. [PMID: 34826203]
  • Qi Zhang, Yizhi Ye, Qian Qu, Yitian Yu, Mingkang Jin, Tao Lu, Haifeng Qian. Enantioselective metabolomic modulations in Arabidopsis thaliana leaf induced by the herbicide dichlorprop. The Science of the total environment. 2021 Nov; 797(?):149015. doi: 10.1016/j.scitotenv.2021.149015. [PMID: 34346373]
  • Hui Chen, Yongxiang Qin, Jiawei Pu, Jinxing Hu, Yuezhong Wen. Phytotoxicity of the chiral herbicide dichlorprop: Cross-talk between nitric oxide, reactive oxygen species and phytohormones. The Science of the total environment. 2021 Sep; 788(?):147866. doi: 10.1016/j.scitotenv.2021.147866. [PMID: 34134377]
  • Julia Buchmueller, Heike Sprenger, Johanna Ebmeyer, Josef Daniel Rasinger, Otto Creutzenberg, Dirk Schaudien, Jan G Hengstler, Georgia Guenther, Albert Braeuning, Stefanie Hessel-Pras. Pyrrolizidine alkaloid-induced transcriptomic changes in rat lungs in a 28-day subacute feeding study. Archives of toxicology. 2021 08; 95(8):2785-2796. doi: 10.1007/s00204-021-03108-x. [PMID: 34185104]
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  • Johanna Ebmeyer, Josef Daniel Rasinger, Jan G Hengstler, Dirk Schaudien, Otto Creutzenberg, Alfonso Lampen, Albert Braeuning, Stefanie Hessel-Pras. Hepatotoxic pyrrolizidine alkaloids induce DNA damage response in rat liver in a 28-day feeding study. Archives of toxicology. 2020 05; 94(5):1739-1751. doi: 10.1007/s00204-020-02779-2. [PMID: 32419051]
  • Stefanie Hessel-Pras, Albert Braeuning, Georgia Guenther, Alshaimaa Adawy, Anne-Margarethe Enge, Johanna Ebmeyer, Colin J Henderson, Jan G Hengstler, Alfonso Lampen, Raymond Reif. The pyrrolizidine alkaloid senecionine induces CYP-dependent destruction of sinusoidal endothelial cells and cholestasis in mice. Archives of toxicology. 2020 01; 94(1):219-229. doi: 10.1007/s00204-019-02582-8. [PMID: 31606820]
  • Siyu Chen, Hui Chen, Zunwei Chen, Yuezhong Wen, Weiping Liu. Enantioselective Phytotoxic Disturbances of Fatty Acids in Arabidopsis thaliana by Dichlorprop. Environmental science & technology. 2019 Aug; 53(15):9252-9259. doi: 10.1021/acs.est.9b03744. [PMID: 31290320]
  • Aizhen Xiong, Youlin Shao, Lianxiang Fang, Xiao Yang, Suocai Zhang, Jian Zheng, Wenxing Ding, Li Yang, Zhengtao Wang. Comparative analysis of toxic components in different medicinal parts of Gynura japonica and its toxicity assessment on mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Feb; 54(?):77-88. doi: 10.1016/j.phymed.2018.06.015. [PMID: 30668385]
  • Johanna Ebmeyer, Jessica Behrend, Mario Lorenz, Georgia Günther, Raymond Reif, Jan G Hengstler, Albert Braeuning, Alfonso Lampen, Stefanie Hessel-Pras. Pyrrolizidine alkaloid-induced alterations of prostanoid synthesis in human endothelial cells. Chemico-biological interactions. 2019 Jan; 298(?):104-111. doi: 10.1016/j.cbi.2018.11.007. [PMID: 30465738]
  • Julia Waizenegger, Albert Braeuning, Markus Templin, Alfonso Lampen, Stefanie Hessel-Pras. Structure-dependent induction of apoptosis by hepatotoxic pyrrolizidine alkaloids in the human hepatoma cell line HepaRG: Single versus repeated exposure. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Apr; 114(?):215-226. doi: 10.1016/j.fct.2018.02.036. [PMID: 29458164]
  • Zunwei Chen, Jia Wang, Siyu Chen, Yuezhong Wen. Enantioselective disturbance of chiral herbicide dichlorprop to nitrogen metabolism of Arabidopsis thaliana: Regular analysis and stable isotope attempt. The Science of the total environment. 2017 Dec; 603-604(?):533-540. doi: 10.1016/j.scitotenv.2017.06.037. [PMID: 28645051]
  • Mengbi Yang, Jianqing Ruan, Hong Gao, Na Li, Jiang Ma, Junyi Xue, Yang Ye, Peter Pi-Cheng Fu, Jiyao Wang, Ge Lin. First evidence of pyrrolizidine alkaloid N-oxide-induced hepatic sinusoidal obstruction syndrome in humans. Archives of toxicology. 2017 Dec; 91(12):3913-3925. doi: 10.1007/s00204-017-2013-y. [PMID: 28620673]
  • Zunwei Chen, Jia Wang, Hui Chen, Yuezhong Wen, Weiping Liu. Enantioselective Phytotoxicity of Dichlorprop to Arabidopsis thaliana: The Effect of Cytochrome P450 Enzymes and the Role of Fe. Environmental science & technology. 2017 Oct; 51(20):12007-12015. doi: 10.1021/acs.est.7b04252. [PMID: 28906105]
  • Xiao Yang, Hua Wang, Hong-Min Ni, Aizhen Xiong, Zhengtao Wang, Hiromi Sesaki, Wen-Xing Ding, Li Yang. Inhibition of Drp1 protects against senecionine-induced mitochondria-mediated apoptosis in primary hepatocytes and in mice. Redox biology. 2017 08; 12(?):264-273. doi: 10.1016/j.redox.2017.02.020. [PMID: 28282614]
  • Xiaojie Liu, Peter G L Klinkhamer, Klaas Vrieling. The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips. Phytochemistry. 2017 Jun; 138(?):93-103. doi: 10.1016/j.phytochem.2017.02.027. [PMID: 28267991]
  • Zunwei Chen, Hui Chen, Yuqin Zou, Yuezhong Wen. Stomatal behaviors reflect enantioselective phytotoxicity of chiral herbicide dichlorprop in Arabidopsis thaliana. The Science of the total environment. 2016 08; 562(?):73-80. doi: 10.1016/j.scitotenv.2016.03.205. [PMID: 27092421]
  • Xiaoxiao Feng, Jianlei Yu, Lixiang Pan, Guochun Song, Hongyan Zhang. Dissipation and Residues of Dichlorprop-P and Bentazone in Wheat-Field Ecosystem. International journal of environmental research and public health. 2016 05; 13(6):. doi: 10.3390/ijerph13060534. [PMID: 27240385]
  • Claudia Luckert, Stefanie Hessel, Dido Lenze, Alfonso Lampen. Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis. Toxicology in vitro : an international journal published in association with BIBRA. 2015 Oct; 29(7):1669-82. doi: 10.1016/j.tiv.2015.06.021. [PMID: 26100227]
  • Reuel A Field, Bryan L Stegelmeier, Steven M Colegate, Ammon W Brown, Benedict T Green. An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides. Toxicon : official journal of the International Society on Toxinology. 2015 Apr; 97(?):36-45. doi: 10.1016/j.toxicon.2015.02.001. [PMID: 25666399]
  • Pavel Kerchev, Per Mühlenbock, Jordi Denecker, Kris Morreel, Frank A Hoeberichts, Katrien Van Der Kelen, Micheal Vandorpe, Long Nguyen, Dominique Audenaert, Frank Van Breusegem. Activation of auxin signalling counteracts photorespiratory H2O2-dependent cell death. Plant, cell & environment. 2015 02; 38(2):253-65. doi: 10.1111/pce.12250. [PMID: 26317137]
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  • Stefanie Hessel, Christoph Gottschalk, Dania Schumann, Anja These, Angelika Preiss-Weigert, Alfonso Lampen. Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine. Molecular nutrition & food research. 2014 May; 58(5):995-1004. doi: 10.1002/mnfr.201300707. [PMID: 24375927]
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