Digitoxigenin (BioDeep_00000408957)

   

natural product


代谢物信息卡片


4-(3,14-DIHYDROXY-10,13-DIMETHYL-HEXADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-17-YL)-5H-FURAN-2-ONE

化学式: C23H34O4 (374.24569640000004)
中文名称: 毛地黄毒苷配基
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 66.67%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])(C5COC(=O)C=5)CC[C@]4(O)[C@]3([H])CC[C@]2([H])C[C@@H](O)C1
InChI: 1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1

描述信息

D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 23

同义名列表

24 个代谢物同义名

Digitoxigenin; 4-(3,14-DIHYDROXY-10,13-DIMETHYL-HEXADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-17-YL)-5H-FURAN-2-ONE; 3-beta,14beta-dihydroxy-5-beta-card-20(22)-enolide; 3,14,21-Trihydroxy-20(22)-norcholenic acid lactone; 3beta,14-Dihydroxy-5beta,20(22)-cardenolide; 5beta,20(22)-Cardenolide-3beta,14-diol; nchembio.2007.53-comp9; Prestwick0_000436; Prestwick2_000436; Prestwick1_000436; Prestwick3_000436; BPBio1_000498; BSPBio_000452; Prestwick_169; STOCK1N-24175; LMST01120001; SPBio_002391; CHEBI:42219; D9404_SIGMA; 37020_FLUKA; 143-62-4; DTX; ST 23:3;O4; Digitoxigenine



数据库引用编号

25 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)

127 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

  • Xiaoqin Zhong, Wei Feng, Lianjie Liu, Qingping Liu, Qiang Xu, Minying Liu, Xiaobao Liu, Shudi Xu, Minzhen Deng, Changsong Lin. Periplogenin inhibits pathologic synovial proliferation and infiltration in rheumatoid arthritis by regulating the JAK2/3-STAT3 pathway. International immunopharmacology. 2024 Feb; 128(?):111487. doi: 10.1016/j.intimp.2024.111487. [PMID: 38183911]
  • Yang Li, Xinchi Feng, Feng Qiu. Determination of Two Wound Healing Components in Streptocaulon juventas (Lour.) Merr.: Periplogenin and Digitoxigenin. Chemistry & biodiversity. 2024 Jan; 21(1):e202301585. doi: 10.1002/cbdv.202301585. [PMID: 38061998]
  • Shohei Takase, Young Sook Yun, Fuki Moriya, Saaya Sekine, Satoshi Yotsumoto, Katsunori Miyake, Tadahiro Yahagi, Akihiro Ito, Hideshi Inoue. 17β-neriifolin from unripe fruits of Cerbera manghas suppressed cell proliferation via the inhibition of HOXA9-dependent transcription and the induction of apoptosis in the human AML cell line THP-1. Journal of natural medicines. 2023 Jan; 77(1):180-187. doi: 10.1007/s11418-022-01659-6. [PMID: 36266527]
  • Shuyao Wang, Xin Yu, Siyang Wu, Wei Yang, Yang Gao, Weihua Wang, Qiutao Wang, Mengmeng Wei, Mingying Zhu, Jiarui Wu, Zheng Yuan, Yingfei Li. Simultaneous determination of periplocin, periplocymarin, periplogenin, periplocoside M and periplocoside N of Cortex Periplocae in rat plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2022 Mar; 36(3):e5283. doi: 10.1002/bmc.5283. [PMID: 34816469]
  • Jéssica Martins de Moura Valadares, Sumit O Bajaj, Hongyan Li, Hua-Yu L Wang, Simone Cavalcante Silva, Israel José Pereira Garcia, Duane Gischewiski Pereira, Pedro Azalim, Luis Eduardo Menezes Quintas, François Noël, Vanessa Faria Cortes, George Augustine O'Doherty, Leandro Augusto Barbosa. Cytotoxic effect of carbohydrate derivatives of digitoxigenin involves modulation of plasma membrane Ca2+ -ATPase. Journal of cellular biochemistry. 2021 12; 122(12):1903-1914. doi: 10.1002/jcb.30150. [PMID: 34553411]
  • Dasom Shin, Hui-Seung Kang, Eun Mi Park, Jungju Kim, Jeongeun Kwon, Junghyuck Suh, Guiim Moon. Authentication of tejocote (Crataegus mexicana) dietary supplements based on DNA barcoding and chemical profiling. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Dec; 38(12):1985-1994. doi: 10.1080/19440049.2021.1964701. [PMID: 34415825]
  • Yunhui Xu, Pauline Marck, Minqi Huang, Jeffrey X Xie, Tong Wang, Joseph I Shapiro, Liquan Cai, Feng Feng, Zijian Xie. Biased Effect of Cardiotonic Steroids on Na/K-ATPase-Mediated Signal Transduction. Molecular pharmacology. 2021 03; 99(3):217-225. doi: 10.1124/molpharm.120.000101. [PMID: 33495275]
  • Camila S Freitas, João A Oliveira-da-Silva, Daniela P Lage, Rafaella R Costa, Débora V C Mendonça, Vívian T Martins, Thiago A R Reis, Luciana M R Antinarelli, Amanda S Machado, Grasiele S V Tavares, Fernanda F Ramos, Vinicio T S Coelho, Rory C F Brito, Fernanda Ludolf, Miguel A Chávez-Fumagalli, Bruno M Roatt, Gabriela S Ramos, Jennifer Munkert, Flaviano M Ottoni, Priscilla R V Campana, Maria V Humbert, Elaine S Coimbra, Fernão C Braga, Rodrigo M Pádua, Eduardo A F Coelho. Digitoxigenin presents an effective and selective antileishmanial action against Leishmania infantum and is a potential therapeutic agent for visceral leishmaniasis. Parasitology research. 2021 Jan; 120(1):321-335. doi: 10.1007/s00436-020-06971-2. [PMID: 33191446]
  • Yingjuan Yang, Yana Liu, Yanhua Zhang, Wei Ji, Lan Wang, Shao C Lee. Periplogenin Activates ROS-ER Stress Pathway to Trigger Apoptosis via BIP-eIF2α- CHOP and IRE1α-ASK1-JNK Signaling Routes. Anti-cancer agents in medicinal chemistry. 2021; 21(1):61-70. doi: 10.2174/1871520620666200708104559. [PMID: 32640963]
  • Mahdieh Mirzaei, Tobias Züst, Gordon C Younkin, Amy P Hastings, Martin L Alani, Anurag A Agrawal, Georg Jander. Less Is More: a Mutation in the Chemical Defense Pathway of Erysimum cheiranthoides (Brassicaceae) Reduces Total Cardenolide Abundance but Increases Resistance to Insect Herbivores. Journal of chemical ecology. 2020 Dec; 46(11-12):1131-1143. doi: 10.1007/s10886-020-01225-y. [PMID: 33180277]
  • Sudarat Kruakaew, Chonticha Seeka, Jantana Yahuafai, Pongpun Siripong, Somyote Sutthivaiyakit. Cytotoxic 20,22-Dihydrodigitoxigenin Glycosides and Other Constituents of Vallaris glabra Stems. Journal of natural products. 2019 12; 82(12):3494-3498. doi: 10.1021/acs.jnatprod.9b00803. [PMID: 31820973]
  • Renyuan Liu, Benwei Su, Feiying Huang, Mei Ru, Hui Zhang, Zhanmin Qin, Yonghua Li, Kaixin Zhu. Identification and analysis of cardiac glycosides in Loranthaceae parasites Taxillus chinensis (DC.) Danser and Scurrula parasitica Linn. and their host Nerium indicum Mill. Journal of pharmaceutical and biomedical analysis. 2019 Sep; 174(?):450-459. doi: 10.1016/j.jpba.2019.05.071. [PMID: 31220703]
  • Matthias Lingemann, Thomas McCarty, Xueqiao Liu, Ursula J Buchholz, Sonja Surman, Scott E Martin, Peter L Collins, Shirin Munir. The alpha-1 subunit of the Na+,K+-ATPase (ATP1A1) is required for macropinocytic entry of respiratory syncytial virus (RSV) in human respiratory epithelial cells. PLoS pathogens. 2019 08; 15(8):e1007963. doi: 10.1371/journal.ppat.1007963. [PMID: 31381610]
  • Wenjing Tu, Sheng Qian. Anti-epileptic effect of 16-O-acetyldigitoxigenin via suppressing mTOR signaling pathway. Cellular and molecular biology (Noisy-le-Grand, France). 2019 Jun; 65(5):59-63. doi: 10.14715/cmb/2019.65.5.10. [PMID: 31304908]
  • Birgit Lohberger, Susanne Wagner, Juliana Wohlmuther, Heike Kaltenegger, Nicole Stuendl, Andreas Leithner, Beate Rinner, Olaf Kunert, Rudolf Bauer, Nadine Kretschmer. Periplocin, the most anti-proliferative constituent of Periploca sepium, specifically kills liposarcoma cells by death receptor mediated apoptosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Dec; 51(?):162-170. doi: 10.1016/j.phymed.2018.10.008. [PMID: 30466613]
  • Izabella Thaís Silva, Jennifer Munkert, Elke Nolte, Naira Fernanda Zanchett Schneider, Sayonarah Carvalho Rocha, Ana Carolina Pacheco Ramos, Wolfgang Kreis, Fernão Castro Braga, Rodrigo Maia de Pádua, Alex G Taranto, Vanessa Cortes, Leandro Augusto Barbosa, Sven Wach, Helge Taubert, Cláudia Maria Oliveira Simões. Cytotoxicity of AMANTADIG - a semisynthetic digitoxigenin derivative - alone and in combination with docetaxel in human hormone-refractory prostate cancer cells and its effect on Na+/K+-ATPase inhibition. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Nov; 107(?):464-474. doi: 10.1016/j.biopha.2018.08.028. [PMID: 30107342]
  • Huaming Liu, Dandan Zhang, Zhidan Tang, Mengjie Sun, John Teye Azietaku, Huizi Ouyang, Yanxu Chang, Meng Wang, Jun He, Xiumei Gao. Tissue distribution study of periplocin and its two metabolites in rats by a validated LC-MS/MS method. Biomedical chromatography : BMC. 2018 Oct; 32(10):e4302. doi: 10.1002/bmc.4302. [PMID: 29809276]
  • Midori A Arai, Ryuta Akamine, Narumi Hayashi, Takashi Koyano, Thaworn Kowithayakorn, Masami Ishibashi. The Notch Inhibitors Isolated from Nerium indicum. Journal of natural products. 2018 05; 81(5):1235-1240. doi: 10.1021/acs.jnatprod.7b01031. [PMID: 29693393]
  • Naira Fernanda Zanchett Schneider, Lara Persich, Sayonarah C Rocha, Ana Carolina Pacheco Ramos, Vanessa Faria Cortes, Izabella Thaís Silva, Jennifer Munkert, Rodrigo M Pádua, Wolfgang Kreis, Alex G Taranto, Leandro A Barbosa, Fernão C Braga, Cláudia M O Simões. Cytotoxic and cytostatic effects of digitoxigenin monodigitoxoside (DGX) in human lung cancer cells and its link to Na,K-ATPase. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jan; 97(?):684-696. doi: 10.1016/j.biopha.2017.10.128. [PMID: 29101813]
  • Yui Kaneta, Midori A Arai, Naoki Ishikawa, Kazufumi Toume, Takashi Koyano, Thaworn Kowithayakorn, Tetsuhiro Chiba, Atsushi Iwama, Masami Ishibashi. Identification of BMI1 Promoter Inhibitors from Beaumontia murtonii and Eugenia operculata. Journal of natural products. 2017 06; 80(6):1853-1859. doi: 10.1021/acs.jnatprod.7b00138. [PMID: 28598616]
  • Elke Nolte, Sven Wach, Izabella Thais Silva, Sabine Lukat, Arif B Ekici, Jennifer Munkert, Frieder Müller-Uri, Wolfgang Kreis, Cláudia Maria Oliveira Simões, Julio Vera, Bernd Wullich, Helge Taubert, Xin Lai. A new semisynthetic cardenolide analog 3β-[2-(1-amantadine)- 1-on-ethylamine]-digitoxigenin (AMANTADIG) affects G2/M cell cycle arrest and miRNA expression profiles and enhances proapoptotic survivin-2B expression in renal cell carcinoma cell lines. Oncotarget. 2017 Feb; 8(7):11676-11691. doi: 10.18632/oncotarget.14644. [PMID: 28099931]
  • Wen-Jing Zhang, Zhen-Bo Song, Yong-Li Bao, Wen-Liang Li, Xiao-Guang Yang, Qi Wang, Chun-Lei Yu, Lu-Guo Sun, Yan-Xin Huang, Yu-Xin Li. Periplogenin induces necroptotic cell death through oxidative stress in HaCaT cells and ameliorates skin lesions in the TPA- and IMQ-induced psoriasis-like mouse models. Biochemical pharmacology. 2016 Apr; 105(?):66-79. doi: 10.1016/j.bcp.2016.02.001. [PMID: 26850986]
  • Diana N Knittel, Peter Lorenz, Ursula Huber, Florian C Stintzing, Dietmar R Kammerer. Characterization of the cardiac glycoside and lipid profiles of Strophanthus kombé Oliv. seeds. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2016 Mar; 71(3-4):55-64. doi: 10.1515/znc-2015-0186. [PMID: 26974139]
  • Jun He, Fang Bo, Yaru Tu, John Teye Azietaku, Ting Dou, Huizi Ouyang, Yanxu Chang, Hong Liu, Xiumei Gao. A validated LC-MS/MS assay for the simultaneous determination of periplocin and its two metabolites, periplocymarin and periplogenin in rat plasma: Application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2015 Oct; 114(?):292-5. doi: 10.1016/j.jpba.2015.06.008. [PMID: 26093244]
  • Fang Bo, Ting Dou, Xingrui Wang, Paul Owusu Donkor, Huizi Ouyang, Yanxu Chang, Yaru Tu, Xiumei Gao, Jun He. A validated LC-MS/MS method for determination of periplogenin in rat plasma and its application in pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 May; 990(?):80-3. doi: 10.1016/j.jchromb.2015.03.017. [PMID: 25864008]
  • Juan J Araya, Kelly Kindscher, Barbara N Timmermann. Cytotoxic cardiac glycosides and other compounds from Asclepias syriaca. Journal of natural products. 2012 Mar; 75(3):400-7. doi: 10.1021/np2008076. [PMID: 22316168]
  • S Panda, A Kar. Periplogenin, isolated from Lagenaria siceraria, ameliorates L-T₄-induced hyperthyroidism and associated cardiovascular problems. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2011 Mar; 43(3):188-93. doi: 10.1055/s-0031-1271621. [PMID: 21287437]
  • Sanae Kanno, Kanako Watanabe, Itaru Yamagishi, Seishiro Hirano, Kayoko Minakata, Kunio Gonmori, Osamu Suzuki. Simultaneous analysis of cardiac glycosides in blood and urine by thermoresponsive LC-MS-MS. Analytical and bioanalytical chemistry. 2011 Jan; 399(3):1141-9. doi: 10.1007/s00216-010-4405-1. [PMID: 21076957]
  • Gerhard Prinsloo, J J Marion Meyer, Ahmed A Hussein, Eduardo Munoz, Rocio Sanchez. A cardiac glucoside with in vitro anti-HIV activity isolated from Elaeodendron croceum. Natural product research. 2010 Nov; 24(18):1743-6. doi: 10.1080/14786410903211912. [PMID: 20981615]
  • Na Han, Jingyu Yang, Linwei Li, Bin Xiao, Sha Sha, Lequan Tran, Jun Yin, Chunfu Wu. Inhibitory activity of a phytochemically characterized fraction from Streptocaulon juventas on lung cancer in nude mice. Planta medica. 2010 Apr; 76(6):561-5. doi: 10.1055/s-0029-1240600. [PMID: 19918714]
  • Petr Obrdlik, Kerstin Diekert, Natalie Watzke, Christine Keipert, Ulrich Pehl, Catrin Brosch, Nicole Boehm, Inga Bick, Maarten Ruitenberg, Walter Volknandt, Bela Kelety. Electrophysiological characterization of ATPases in native synaptic vesicles and synaptic plasma membranes. The Biochemical journal. 2010 Mar; 427(1):151-9. doi: 10.1042/bj20091380. [PMID: 20100168]
  • Xiuhai Gan, Xin Zhou, Huaguo Chen, Xiaojian Gong, Chao Zhao. [Chemical constituents of Periploca forrestii]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Dec; 34(24):3225-8. doi: . [PMID: 20353006]
  • Sunanda Panda, Anand Kar. Periplogenin-3-O- -D-glucopyranosyl -(1-->6)- -D-glucopyaranosyl- -(1-->4) -D-cymaropyranoside, isolated from Aegle marmelos protects doxorubicin induced cardiovascular problems and hepatotoxicity in rats. Cardiovascular therapeutics. 2009; 27(2):108-16. doi: 10.1111/j.1755-5922.2009.00078.x. [PMID: 19426248]
  • Marianna Usai, Aldo Domenico Atzei, Mauro Marchetti. Cardenolides content in wild Sardinian Digitalis purpurea L. populations. Natural product research. 2007 Jul; 21(9):798-804. doi: 10.1080/14786410701218291. [PMID: 17654283]
  • Ming Zhao, Liming Bai, Liyan Wang, Asami Toki, Toshiaki Hasegawa, Midori Kikuchi, Mariko Abe, Jun-ichi Sakai, Ryo Hasegawa, Yuhua Bai, Tomokazu Mitsui, Hirotsugu Ogura, Takao Kataoka, Seiko Oka, Hiroko Tsushima, Miwa Kiuchi, Katutoshi Hirose, Akihiro Tomida, Takashi Tsuruo, Masayoshi Ando. Bioactive cardenolides from the stems and twigs of Nerium oleander. Journal of natural products. 2007 Jul; 70(7):1098-103. doi: 10.1021/np068066g. [PMID: 17595134]
  • Frank Schaller, Wolfgang Kreis. Cardenolide genin pattern in Isoplexis plants and shoot cultures. Planta medica. 2006 Oct; 72(12):1149-56. doi: 10.1055/s-2006-947194. [PMID: 16902853]
  • Thitima Lhinhatrakool, Somyote Sutthivaiyakit. 19-Nor- and 18,20-epoxy-cardenolides from the leaves of Calotropis gigantea. Journal of natural products. 2006 Aug; 69(8):1249-51. doi: 10.1021/np060249f. [PMID: 16933890]
  • Paolo Manunta, Mara Ferrandi, Elisabetta Messaggio, Patrizia Ferrari. A new antihypertensive agent that antagonizes the prohypertensive effect of endogenous ouabain and adducin. Cardiovascular & hematological agents in medicinal chemistry. 2006 Jan; 4(1):61-6. doi: 10.2174/187152506775268811. [PMID: 16529550]
  • Hiroyuki Nakano, Manabu Matsunawa, Atsutaka Yasui, Ryutaro Adachi, Katsuyoshi Kawana, Iichiro Shimomura, Makoto Makishima. Enhancement of ligand-dependent vitamin D receptor transactivation by the cardiotonic steroid bufalin. Biochemical pharmacology. 2005 Nov; 70(10):1479-86. doi: 10.1016/j.bcp.2005.08.012. [PMID: 16183038]
  • Miguel López-Lázaro, Nuria Pastor, Sami S Azrak, María Jesús Ayuso, Caroline A Austin, Felipe Cortés. Digitoxin inhibits the growth of cancer cell lines at concentrations commonly found in cardiac patients. Journal of natural products. 2005 Nov; 68(11):1642-5. doi: 10.1021/np050226l. [PMID: 16309315]
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  • Margarita Ramirez, Leonardo Del Valle, Alicia Sanchez-Mendoza, Fermin Alejandro Tenorio, Gabriela Zarco, Gustavo Pastelin. Effect of the digitoxigenin derivative, INCICH-D7, on Na+, K+-ATPase. Biochemical pharmacology. 2005 Sep; 70(6):851-7. doi: 10.1016/j.bcp.2005.06.020. [PMID: 16081050]
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