1ST40320 (BioDeep_00000396796)

Main id: BioDeep_00000002342

 

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-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)-

化学式: C18H25NO6 (351.168179)
中文名称: 倒千里光碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC=C1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(CO)O)C
InChI: InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-/m1/s1

描述信息

Retrorsine is a macrolide.
Retrorsine is a natural product found in Crotalaria spartioides, Senecio malacitanus, and other organisms with data available.
D000970 - Antineoplastic Agents
Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury[1][2].
Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury[1][2].

同义名列表

30 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-6-(hydroxymethyl)-5-methyl-, (3Z,5R,6S,14aR,14bR)-; (5R,6S,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[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-6-hydroxymethyl-5-methyl(1,6)dioxacyclododeca(2,3,4-gh)pyrrolizidine-2,7-dione; (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0??,??]heptadec-11-ene-3,8-dione; trans-15-Ethylidene-12beta-hydroxy-12alpha-hydroxymethyl-13beta-methylsenec-1-enine; (Z)-ethylidene-hydroxy-(hydroxymethyl)-methyl-[?]dione; (15Z)-12,18-dihydroxysenecionan-11,16-dione; Senecionan-11,16-dione, 12,18-dihydroxy-; cis-Retronecic acid ester of retronecine; 12,18-Dihydroxy-senecionan-11,16-dione; 12,18-Dihydroxysenecionan-11,16-dione; BCJMNZRQJAVDLD-CQRYIUNCSA-N; Retrorsine, >=90\\% (HPLC); retrorsine hydrochloride; retrorsine, (15E)-isomer; RETRORSINE [HSDB]; RETRORSINE [IARC]; Prestwick3_000637; Prestwick2_000637; beta-Longilobine; UNII-XJ86XWL8IY; RETRORSINE [MI]; BPBio1_000698; retrorsine; XJ86XWL8IY; Retrorcine; Retrorsin; Usaramine; Isatidine; 1ST40320



数据库引用编号

7 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)

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

  • Yongguo Dai, Qi Guo, Kequan Xu, Zheng Gong, Shuaikai Qiu, Xiaoxiang Sun, Jie Liu, Yuxi Wang, Zhixin Yang, Hui Wang, Yu Guo. Lactational retrorsine exposure changes maternal milk components and disturbs metabolism homeostasis of offspring rats. The Science of the total environment. 2023 Jun; ?(?):164929. doi: 10.1016/j.scitotenv.2023.164929. [PMID: 37329908]
  • Weiwei Li, Ting Cheng, Tingting Jiang, Mengyue Zhou, Bowen Gong, Guode Zhao, Jing Li, Rong Tan, Xiaojing Yang, Kandarp Joshi, Ying Peng, Maosheng Cheng, Ting Liu, Dan Ohtan Wang, Jiang Zheng. Hepatic RNA adduction derived from metabolic activation of retrorsine in vitro and in vivo. Chemico-biological interactions. 2022 Sep; 365(?):110047. doi: 10.1016/j.cbi.2022.110047. [PMID: 35917946]
  • Lin Zhu, Junyi Xue, Yisheng He, Qingsu Xia, Peter P Fu, Ge Lin. Correlation Investigation between Pyrrole-DNA and Pyrrole-Protein Adducts in Male ICR Mice Exposed to Retrorsine, a Hepatotoxic Pyrrolizidine Alkaloid. Toxins. 2022 05; 14(6):. doi: 10.3390/toxins14060377. [PMID: 35737038]
  • Feifei Lin, Yan Ma, Anni Pan, Yang Ye, Jia Liu. Quantification of Usaramine and its N-Oxide Metabolite in Rat Plasma Using Liquid Chromatography-Tandem Mass Spectrometry. Journal of analytical toxicology. 2022 May; 46(5):512-518. doi: 10.1093/jat/bkab060. [PMID: 34086913]
  • Jing Li, Mengyue Zhou, Xiaoqiong Lai, Yang Wang, Ying Zou, Kunna Li, Weiwei Li, Jiang Zheng. Toxicokinetic and bioavailability studies on retrorsine in mice, and ketoconazole-induced alteration in toxicokinetic properties. Biomedical chromatography : BMC. 2022 Feb; 36(2):e5270. doi: 10.1002/bmc.5270. [PMID: 34727371]
  • Jiang Ma, Chunyuan Zhang, Yisheng He, Xinmeng Chen, Ge Lin. Fasting augments pyrrolizidine alkaloid-induced hepatotoxicity. Archives of toxicology. 2022 02; 96(2):639-651. doi: 10.1007/s00204-021-03193-y. [PMID: 34792613]
  • 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]
  • Lin Zhu, Chunyuan Zhang, Wei Zhang, Qingsu Xia, Jiang Ma, Xin He, Yisheng He, Peter P Fu, Wei Jia, Yuzheng Zhuge, Ge Lin. Developing urinary pyrrole-amino acid adducts as non-invasive biomarkers for identifying pyrrolizidine alkaloids-induced liver injury in human. Archives of toxicology. 2021 10; 95(10):3191-3204. doi: 10.1007/s00204-021-03129-6. [PMID: 34390356]
  • Li Guo, Li Zhang, Haiman Xu, Pei Yu, Zhigang Wang, Danyi Lu, Min Chen, Baojian Wu. Diurnal hepatic CYP3A11 contributes to chronotoxicity of the pyrrolizidine alkaloid retrorsine in mice. Xenobiotica; the fate of foreign compounds in biological systems. 2021 Sep; 51(9):1019-1028. doi: 10.1080/00498254.2021.1950867. [PMID: 34311664]
  • Xiaoyan Pang, Chongzhuang Tang, Peng Cao, Lei Zhou, Xiaoyan Chen. Metabolic Activation of Retrorsine may Disrupt Bile Acid Homeostasis in Mice through the Nrf2 Pathway. Current drug metabolism. 2021; 22(11):870-881. doi: 10.2174/1389200222666210427124332. [PMID: 33906588]
  • Xiaoyan Pang, Chongzhuang Tang, Fandi Kong, Meixia Chen, Xiaoyan Chen. CYP2C and CYP2B Mediated Metabolic Activation of Retrorsine in Cyp3a Knockout Mice. Current drug metabolism. 2020; 21(13):1040-1051. doi: 10.2174/1389200221666201202101715. [PMID: 33267758]
  • Yu Guo, Di Xiao, Xiaojing Yang, Jiang Zheng, Shuwei Hu, Panfeng Wu, Xiaoxia Li, Hao Kou, Hui Wang. Prenatal exposure to pyrrolizidine alkaloids induced hepatotoxicity and pulmonary injury in fetal rats. Reproductive toxicology (Elmsford, N.Y.). 2019 04; 85(?):34-41. doi: 10.1016/j.reprotox.2019.02.006. [PMID: 30771476]
  • Xiaojie Liu, Klaas Vrieling, Peter G L Klinkhamer. Phytochemical Background Mediates Effects of Pyrrolizidine Alkaloids on Western Flower Thrips. Journal of chemical ecology. 2019 Feb; 45(2):116-127. doi: 10.1007/s10886-018-1009-2. [PMID: 30221331]
  • Xiaojing Yang, Weiwei Li, Hui Li, Xu Wang, Yan Chen, Xiucai Guo, Ying Peng, Jiang Zheng. A Difference in Internal Exposure Makes Newly Weaned Mice More Susceptible to the Hepatotoxicity of Retrorsine Than Adult Mice. Chemical research in toxicology. 2018 12; 31(12):1348-1355. doi: 10.1021/acs.chemrestox.8b00220. [PMID: 30427168]
  • Yao Lu, Jiang Ma, Zijing Song, Yang Ye, Peter P Fu, Ge Lin. The role of formation of pyrrole-ATP synthase subunit beta adduct in pyrrolizidine alkaloid-induced hepatotoxicity. Archives of toxicology. 2018 11; 92(11):3403-3414. doi: 10.1007/s00204-018-2309-6. [PMID: 30244272]
  • Xiu-Ren Hu, Gui-Xin Chou, Cheng-Gang Zhang. Flavonoids, alkaloids from the seeds of Crotalaria pallida and their cytotoxicity and anti-inflammatory activities. Phytochemistry. 2017 Nov; 143(?):64-71. doi: 10.1016/j.phytochem.2017.07.010. [PMID: 28777979]
  • 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]
  • Lin Zhu, Junyi Xue, Qingsu Xia, Peter P Fu, Ge Lin. The long persistence of pyrrolizidine alkaloid-derived DNA adducts in vivo: kinetic study following single and multiple exposures in male ICR mice. Archives of toxicology. 2017 Feb; 91(2):949-965. doi: 10.1007/s00204-016-1713-z. [PMID: 27125825]
  • Themístocles da Silva Negreiros Neto, Dale Gardner, Fernando Hallwass, Ana Jéssica Matias Leite, Camila Guimarães de Almeida, Laura Nunes Silva, Alan de Araújo Roque, Fernanda Gobbi de Bitencourt, Euzébio Guimarães Barbosa, Tiana Tasca, Alexandre José Macedo, Mauro Vieira de Almeida, Raquel Brandt Giordani. Activity of pyrrolizidine alkaloids against biofilm formation and Trichomonas vaginalis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2016 Oct; 83(?):323-329. doi: 10.1016/j.biopha.2016.06.033. [PMID: 27399809]
  • Eva Castells, Patrick P J Mulder, Míriam Pérez-Trujillo. Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): implications for toxicity. Phytochemistry. 2014 Dec; 108(?):137-46. doi: 10.1016/j.phytochem.2014.09.006. [PMID: 25269662]
  • Damjan Janeš, Samo Kreft. TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound. Acta pharmaceutica (Zagreb, Croatia). 2014 Dec; 64(4):503-8. doi: 10.2478/acph-2014-0031. [PMID: 25531790]
  • Gonzalo J Diaz, Leidy X Almeida, Dale R Gardner. Effects of dietary Crotalaria pallida seeds on the health and performance of laying hens and evaluation of residues in eggs. Research in veterinary science. 2014 Oct; 97(2):297-303. doi: 10.1016/j.rvsc.2014.06.011. [PMID: 25062989]
  • Meijuan Tu, Liping Li, Hongmei Lei, Zhiyuan Ma, Zhongjian Chen, Siyuan Sun, Siyun Xu, Hui Zhou, Su Zeng, Huidi Jiang. Involvement of organic cation transporter 1 and CYP3A4 in retrorsine-induced toxicity. Toxicology. 2014 Aug; 322(?):34-42. doi: 10.1016/j.tox.2014.04.007. [PMID: 24799337]
  • 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]
  • T Tsuchida, Y-W Zheng, R-R Zhang, T Takebe, Y Ueno, K Sekine, H Taniguchi. The development of humanized liver with Rag1 knockout rats. Transplantation proceedings. 2014 May; 46(4):1191-3. doi: 10.1016/j.transproceed.2013.12.026. [PMID: 24815157]
  • Petra Krause, Kirsten Unthan-Fechner, Irmelin Probst, Sarah Koenig. Cultured hepatocytes adopt progenitor characteristics and display bipotent capacity to repopulate the liver. Cell transplantation. 2014; 23(7):805-17. doi: 10.3727/096368913x664856. [PMID: 23485196]
  • Jiayin Han, Aihu Liang, Yan Yi. [Developmental toxicity of retrorsine on mouse embryos in vitro]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jul; 36(14):1901-4. doi: NULL. [PMID: 22016956]
  • Biao Zhang, Mitsuhiro Inagaki, Bojian Jiang, Masaaki Miyakoshi, Jun Arikura, Katsuhiro Ogawa, Shinichi Kasai. Effects of bone marrow and hepatocyte transplantation on liver injury. The Journal of surgical research. 2009 Nov; 157(1):71-80. doi: 10.1016/j.jss.2008.12.013. [PMID: 19345373]
  • Takayuki Hamada, Susumu Eguchi, Mitsuhisa Takatsuki, Kosho Yamanouchi, Nozomu Sugiyama, Yujo Kawashita, Sadayuki Okudaira, Yoshitsugu Tajima, Takehisa Ishii, Takashi Kanematsu. Low-dose recombinant human hepatocyte growth factor enhances effect of hepatocyte transplantation in rats treated with retrorsine. Hepato-gastroenterology. 2009 Sep; 56(94-95):1466-70. doi: . [PMID: 19950811]
  • Kate E Brilliant, David R Mills, Helen M Callanan, Douglas C Hixson. Engraftment of syngeneic and allogeneic endothelial cells, hepatocytes and cholangiocytes into partially hepatectomized rats previously treated with mitomycin C. Transplantation. 2009 Aug; 88(4):486-95. doi: 10.1097/tp.0b013e3181b0b98a. [PMID: 19696631]
  • 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]
  • Yu-Ping Wang, Peter P Fu, Ming W Chou. Metabolic activation of the tumorigenic pyrrolizidine alkaloid, retrorsine, leading to DNA adduct formation in vivo. International journal of environmental research and public health. 2005 Apr; 2(1):74-9. doi: 10.3390/ijerph2005010074. [PMID: 16705803]
  • W H G Hol, A Van Veen. Pyrrolizidine alkaloids from Senecio jacobaea affect fungal growth. Journal of chemical ecology. 2002 Sep; 28(9):1763-72. doi: 10.1023/a:1020557000707. [PMID: 12449504]
  • A N Irani, H Malhi, S Slehria, G R Gorla, I Volenberg, M L Schilsky, S Gupta. Correction of liver disease following transplantation of normal rat hepatocytes into Long-Evans Cinnamon rats modeling Wilson's disease. Molecular therapy : the journal of the American Society of Gene Therapy. 2001 Mar; 3(3):302-9. doi: 10.1006/mthe.2001.0271. [PMID: 11273771]
  • S Laconi, S Pillai, P P Porcu, D A Shafritz, P Pani, E Laconi. Massive liver replacement by transplanted hepatocytes in the absence of exogenous growth stimuli in rats treated with retrorsine. The American journal of pathology. 2001 Feb; 158(2):771-7. doi: 10.1016/s0002-9440(10)64019-9. [PMID: 11159214]
  • G J Gordon, W B Coleman, J W Grisham. Induction of cytochrome P450 enzymes in the livers of rats treated with the pyrrolizidine alkaloid retrorsine. Experimental and molecular pathology. 2000 Aug; 69(1):17-26. doi: 10.1006/exmp.2000.2308. [PMID: 10891289]
  • G Lin, I P Nnane, T Y Cheng. The effects of pretreatment with glycyrrhizin and glycyrrhetinic acid on the retrorsine-induced hepatotoxicity in rats. Toxicon : official journal of the International Society on Toxinology. 1999 Sep; 37(9):1259-70. doi: 10.1016/s0041-0101(98)00263-3. [PMID: 10400287]
  • A González, C Rossini, M Eisner, T Eisner. Sexually transmitted chemical defense in a moth (Utetheisa ornatrix). Proceedings of the National Academy of Sciences of the United States of America. 1999 May; 96(10):5570-4. doi: 10.1073/pnas.96.10.5570. [PMID: 10318925]
  • R Oren, M D Dabeva, P M Petkov, E Hurston, E Laconi, D A Shafritz. Restoration of serum albumin levels in nagase analbuminemic rats by hepatocyte transplantation. Hepatology (Baltimore, Md.). 1999 Jan; 29(1):75-81. doi: 10.1002/hep.510290147. [PMID: 9862853]
  • E Laconi, R Oren, D K Mukhopadhyay, E Hurston, S Laconi, P Pani, M D Dabeva, D A Shafritz. Long-term, near-total liver replacement by transplantation of isolated hepatocytes in rats treated with retrorsine. The American journal of pathology. 1998 Jul; 153(1):319-29. doi: 10.1016/s0002-9440(10)65574-5. [PMID: 9665494]
  • N Aston, P Morris, S Tanner. Retrorsine in breast milk influences copper handling in suckling rat pups. Journal of hepatology. 1996 Nov; 25(5):748-55. doi: 10.1016/s0168-8278(96)80248-0. [PMID: 8938555]
  • 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]
  • P Morris, D O'Neill, S Tanner. Synergistic liver toxicity of copper and retrorsine in the rat. Journal of hepatology. 1994 Nov; 21(5):735-42. doi: 10.1016/s0168-8278(94)80232-7. [PMID: 7890887]
  • 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]
  • P S Chu, M W Lamé, H J Segall. In vivo metabolism of retrorsine and retrorsine-N-oxide. Archives of toxicology. 1993; 67(1):39-43. doi: 10.1007/bf02072033. [PMID: 8452478]
  • E Leidinger, G Loupal, R Gutleb, I Miller, R Chizzola. [Toxic effects in rabbits after immunization against the pyrrolizidine alkaloid retrorsine]. DTW. Deutsche tierarztliche Wochenschrift. 1992 Aug; 99(8):332-5. doi: . [PMID: 1425325]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]
  • P S Chu, H J Segall. Species difference in the urinary excretion of isatinecic acid from the pyrrolizidine alkaloid retrorsine. Comparative biochemistry and physiology. C, Comparative pharmacology and toxicology. 1991; 100(3):683-6. doi: 10.1016/0742-8413(91)90061-w. [PMID: 1687569]