Squalidin (BioDeep_00000395565)

Main id: BioDeep_00000000416

 

PANOMIX_OTCML-2023 Volatile Flavor Compounds


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-, (3E,5R,6R,14AR,14BR)-

化学式: C18H25NO5 (335.173264)
中文名称: 全缘千里光碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C/C=C1/C[C@@H](C)[C@](C)(O)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23
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/b12-4+/t11-,14-,15-,18-/m1/s1

描述信息

Integerrimine is a macrolide.
Integerrimine is a natural product found in Crotalaria micans, Tussilago farfara, and other organisms with data available.
See also: Petasites hybridus root (part of).
D000970 - Antineoplastic Agents

同义名列表

21 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-, (3E,5R,6R,14AR,14BR)-; (5R,6R,9a1R,14aR,E)-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,4E,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; Senecionan-11,16-dione, 12-hydroxy-;Aureine;Senecionin; Senecionan-11,16-dione, 12-hydroxy-, (15E)-; (15E)-12-Hydroxysenecionan-11,16-dione; SENECIONINE C15-TRANS ISOMER [MI]; SENECIONINE C15-TRANS ISOMER; senecionine citrate (1:1); senecionine, (15E)-isomer; senecionine citratre; (-)-Integerrimine; intergerrimine; integerrimine; Inegerrimine; Senecionine; squalidine; Squalidin; 1ST160719; Integerrimine; Integerrimine



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)

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

  • 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]
  • 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]
  • 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]
  • Jean-François Picron, Florian Philippe, Nelly Dubrulle, Els Van Hoeck, Nicole Giraud, Séverine Goscinny, Céline Vanhee. Targeted LC-MS/MS combined with multilocus DNA metabarcoding as a combinatory approach to determine the amount and the source of pyrrolizidine alkaloids contamination in popular cooking herbs, seeds, spices and leafy vegetables. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Jun; 38(6):962-977. doi: 10.1080/19440049.2021.1889043. [PMID: 33780325]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Carlos H Z Martins, Beatriz P Cunha, Vera N Solferini, José R Trigo. Feeding on Host Plants with Different Concentrations and Structures of Pyrrolizidine Alkaloids Impacts the Chemical-Defense Effectiveness of a Specialist Herbivore. PloS one. 2015; 10(10):e0141480. doi: 10.1371/journal.pone.0141480. [PMID: 26517873]
  • Elizabeth M Mudge, A Maxwell P Jones, Paula N Brown. Quantification of pyrrolizidine alkaloids in North American plants and honey by LC-MS: single laboratory validation. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2015; 32(12):2068-74. doi: 10.1080/19440049.2015.1099743. [PMID: 26482059]
  • Tri R Nuringtyas, Robert Verpoorte, Peter G L Klinkhamer, Monique M van Oers, Kirsten A Leiss. Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays. Journal of chemical ecology. 2014 Jun; 40(6):609-16. doi: 10.1007/s10886-014-0459-4. [PMID: 24981118]
  • Aizhen Xiong, Fan Yang, Lianxiang Fang, Li Yang, Yuqi He, Yu-Jui Yvonne Wan, Yvonne Yu-Jui Wan, Ying Xu, Meng Qi, Xiuli Wang, Kate Yu, Karl Wah-Keung Tsim, Zhengtao Wang. Metabolomic and genomic evidence for compromised bile acid homeostasis by senecionine, a hepatotoxic pyrrolizidine alkaloid. Chemical research in toxicology. 2014 May; 27(5):775-86. doi: 10.1021/tx400451q. [PMID: 24641316]
  • 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]
  • Fabiana Elias, Andreia O Latorre, Fernando Pípole, Mitsue Haraguchi, Silvana L Górniak, Isis M Hueza. Haematological and immunological effects of repeated dose exposure of rats to integerrimine N-oxide from Senecio brasiliensis. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Sep; 49(9):2313-9. doi: 10.1016/j.fct.2011.06.032. [PMID: 21722699]
  • Changhong Wang, Yan Li, Jiangguo Gao, Yuqi He, Aizhen Xiong, Li Yang, Xuemei Cheng, Yueming Ma, Zhengtao Wang. The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS. Analytical and bioanalytical chemistry. 2011 Jul; 401(1):275-87. doi: 10.1007/s00216-011-5075-3. [PMID: 21573843]
  • Aizhen Xiong, Li Yang, Xuejing Yang, Changhong Wang, Zhengtao Wang. [Simultaneous quantitation of adonifoline and senecionine in Senecio herbs by UPLC-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Mar; 36(6):702-5. doi: . [PMID: 21710732]
  • Qingning Liang, Yuchen Sheng, Ping Jiang, Lili Ji, Yuye Xia, Yang Min, Zhengtao Wang. The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury. Toxicology. 2011 Feb; 280(1-2):61-9. doi: 10.1016/j.tox.2010.11.010. [PMID: 21126554]
  • Yu-Qi He, Yong Liu, Bin-Feng Zhang, Hui-Xin Liu, Yan-Liu Lu, Li Yang, Ai-zhen Xiong, Ling-Ling Xu, Chang-Hong Wang, Ling Yang, Zheng-Tao Wang. Identification of the UDP-glucuronosyltransferase isozyme involved in senecionine glucuronidation in human liver microsomes. Drug metabolism and disposition: the biological fate of chemicals. 2010 Apr; 38(4):626-34. doi: 10.1124/dmd.109.030460. [PMID: 20056725]
  • Yu-Qi He, Li Yang, Hui-Xin Liu, Jiang-Wei Zhang, Yong Liu, Alan Fong, Ai-Zhen Xiong, Yan-Liu Lu, Ling Yang, Chang-Hong Wang, Zheng-Tao Wang. Glucuronidation, a new metabolic pathway for pyrrolizidine alkaloids. Chemical research in toxicology. 2010 Mar; 23(3):591-9. doi: 10.1021/tx900328f. [PMID: 20092275]
  • Aizhen Xiong, Yan Li, Li Yang, Jiangguo Gao, Yuqi He, Changhong Wang, Zhengtao Wang. Simultaneous determination of senecionine, adonifoline and their metabolites in rat serum by UPLC-ESIMS and its application in pharmacokinetic studies. Journal of pharmaceutical and biomedical analysis. 2009 Dec; 50(5):1070-4. doi: 10.1016/j.jpba.2009.06.037. [PMID: 19616399]
  • Annika Reinhard, Martina Janke, Werner von der Ohe, Michael Kempf, Claudine Theuring, Thomas Hartmann, Peter Schreier, Till Beuerle. Feeding deterrence and detrimental effects of pyrrolizidine alkaloids fed to honey bees (Apis mellifera). Journal of chemical ecology. 2009 Sep; 35(9):1086-95. doi: 10.1007/s10886-009-9690-9. [PMID: 19777310]
  • Zhangjian Jiang, Feng Liu, Jennifer Jia Lei Goh, Lijun Yu, Sam Fong Yau Li, Eng Shi Ong, Choon Nam Ong. Determination of senkirkine and senecionine in Tussilago farfara using microwave-assisted extraction and pressurized hot water extraction with liquid chromatography tandem mass spectrometry. Talanta. 2009 Jul; 79(2):539-46. doi: 10.1016/j.talanta.2009.04.028. [PMID: 19559918]
  • A F P Dimande, C J Botha, L Prozesky, L Bekker, G M Rösemann, L Labuschagne, E Retief. The toxicity of Senecio inaequidens DC. Journal of the South African Veterinary Association. 2007 Sep; 78(3):121-9. doi: 10.4102/jsava.v78i3.302. [PMID: 18237033]
  • Mirka Macel, Klaas Vrieling, Peter G L Klinkhamer. Variation in pyrrolizidine alkaloid patterns of Senecio jacobaea. Phytochemistry. 2004 Apr; 65(7):865-73. doi: 10.1016/j.phytochem.2004.02.009. [PMID: 15081286]
  • I Narberhaus, C Theuring, T Hartmann, S Dobler. Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology. 2003 Aug; 173(6):483-91. doi: 10.1007/s00360-003-0356-6. [PMID: 12802610]
  • Claudia Naumann, Thomas Hartmann, Dietrich Ober. Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae. Proceedings of the National Academy of Sciences of the United States of America. 2002 Apr; 99(9):6085-90. doi: 10.1073/pnas.082674499. [PMID: 11972041]
  • M T Skaanild, C Friis, L Brimer. Interplant alkaloid variation and Senecio vernalis toxicity in cattle. Veterinary and human toxicology. 2001 Jun; 43(3):147-51. doi: . [PMID: 11383654]
  • M Reina, A González-Coloma, C Gutiérrez, R Cabrera, M L Rodríguez, V Fajardo, L Villarroel. Defensive chemistry of Senecio miser. Journal of natural products. 2001 Jan; 64(1):6-11. doi: 10.1021/np000114o. [PMID: 11170657]
  • E Roeder, A Eckert, H Wiedenfeld. Pyrrolizidine alkaloids from Gynura divaricata. Planta medica. 1996 Aug; 62(4):386. doi: 10.1055/s-2006-957921. [PMID: 8792680]
  • T Langer, E Möstl, R Chizzola, R Gutleb. A competitive enzyme immunoassay for the pyrrolizidine alkaloids of the senecionine type. Planta medica. 1996 Jun; 62(3):267-71. doi: 10.1055/s-2006-957875. [PMID: 8693043]
  • M Bah, R Bye, R Pereda-Miranda. Hepatotoxic pyrrolizidine alkaloids in the Mexican medicinal plant Packera candidissima (Asteraceae: Senecioneae). Journal of ethnopharmacology. 1994 Jun; 43(1):19-30. doi: 10.1016/0378-8741(94)90112-0. [PMID: 7967646]
  • M Peterka, S Sarin, E Roeder, H Wiedenfeld, M Halasková. Differing embryotoxic effects of senecionine and senecionine-N-oxide on the chick embryo. Functional and developmental morphology. 1994; 4(2):89-92. doi: . [PMID: 7873804]
  • C L Miranda, W Chung, R E Reed, X Zhao, M C Henderson, J L Wang, D E Williams, D R Buhler. Flavin-containing monooxygenase: a major detoxifying enzyme for the pyrrolizidine alkaloid senecionine in guinea pig tissues. Biochemical and biophysical research communications. 1991 Jul; 178(2):546-52. doi: 10.1016/0006-291x(91)90142-t. [PMID: 1907134]
  • J E Estep, M W Lamé, A D Jones, H J Segall. N-acetylcysteine-conjugated pyrrole identified in rat urine following administration of two pyrrolizidine alkaloids, monocrotaline and senecionine. Toxicology letters. 1990 Nov; 54(1):61-9. doi: 10.1016/0378-4274(90)90056-r. [PMID: 2123045]
  • J E Estep, M W Lamé, H J Segall. Excretion and blood radioactivity levels following [14C]senecionine administration in the rat. Toxicology. 1990 Nov; 64(2):179-89. doi: 10.1016/0300-483x(90)90134-3. [PMID: 2219139]
  • D S Griffin, H J Segall. Lipid peroxidation and cellular damage caused by the pyrrolizidine alkaloid senecionine, the alkenal trans-4-hydroxy-2-hexenal, and related alkenals. Cell biology and toxicology. 1987 Dec; 3(4):379-90. doi: 10.1007/bf00119911. [PMID: 3507264]
  • D G Cai. [Solvent extraction and isolation of alkaloids A and B from Senecio fuberi]. Zhong yao tong bao (Beijing, China : 1981). 1987 Mar; 12(3):40, 44. doi: ". [PMID: 2957096]
  • H J Segall, D W Wilson, J L Dallas, W F Haddon. trans-4-Hydroxy-2-hexenal: a reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine. Science (New York, N.Y.). 1985 Aug; 229(4712):472-5. doi: 10.1126/science.4012327. [PMID: 4012327]
  • U Candrian, J Lüthy, C Schlatter. In vivo covalent binding of retronecine-labelled [3H]seneciphylline and [3H]senecionine to DNA of rat liver, lung and kidney. Chemico-biological interactions. 1985 Jun; 54(1):57-69. doi: 10.1016/s0009-2797(85)80152-6. [PMID: 4017105]
  • D F Eastman, G P Dimenna, H J Segall. Covalent binding of two pyrrolizidine alkaloids, senecionine and seneciphylline, to hepatic macromolecules and their distribution, excretion, and transfer into milk of lactating mice. Drug metabolism and disposition: the biological fate of chemicals. 1982 May; 10(3):236-40. doi: . [PMID: 6179729]