Oleandrin (BioDeep_00000000245)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate

化学式: C32H48O9 (576.3298158)
中文名称: 欧夹竹桃甙丙, 欧夹竹桃苷, 夹竹桃育齐墩果君欧莲素, 欧夹竹桃苷丙
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 4.27%

分子结构信息

SMILES: C1[C@@]2(C)[C@]([H])(CC[C@]3([H])[C@]2([H])CC[C@]2(C)[C@@]([H])(C4COC(=O)C=4)[C@@H](OC(=O)C)C[C@]32O)C[C@@H](O[C@H]2C[C@H](OC)[C@@H](O)[C@H](C)O2)C1
InChI: InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1

描述信息

Oleandrin is a steroid saponin that consists of oleandrigenin having a 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl residue attached to the oxygen function at position 3. It is a cardenolide glycoside, a 14beta-hydroxy steroid, a steroid ester and a steroid saponin. It is functionally related to an oleandrigenin.
Oleandrin has been used in trials studying the treatment of Lung Cancer and Chemotherapeutic Agent Toxicity.
Oleandrin is a natural product found in Daphnis nerii, Plumeria, and other organisms with data available.
Oleandrin is a lipid soluble cardiac glycoside with potential antineoplastic activity. Upon administration, oleandrin specifically binds to and inhibits the alpha3 subunit of the Na/K-ATPase pump in human cancer cells. This may inhibit the phosphorylation of Akt, upregulate MAPK, inhibit NF-kb activation and inhibit FGF-2 export and may downregulate mTOR thereby inhibiting p70S6K and S6 protein expression. All of this may lead to an induction of apoptosis. As cancer cells with relatively higher expression of the alpha3 subunit and with limited expression of the alpha1 subunit are more sensitive to oleandrin, one may predict the tumor response to treatment with lipid-soluble cardiac glycosides such as oleandrin based on the tumors Na/K-ATPase pump protein subunit expression. Overexpression of the alpha3 subunit in tumor cells correlates with tumor proliferation.
See also: Nerium oleander leaf (part of).
A steroid saponin that consists of oleandrigenin having a 2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl residue attached to the oxygen function at position 3.
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2262
Oleandrin (PBI-05204) inhibits the Na+, K+-ATPase activity with an IC50 of 620 nM.
Oleandrin (PBI-05204) inhibits the Na+, K+-ATPase activity with an IC50 of 620 nM.

同义名列表

34 个代谢物同义名

[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate; [(3S,8R,9S,10S,13R,14S,16S,17R)-14-Hydroxy-3-[(4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate; CARD-20(22)-ENOLIDE, 16-(ACETYLOXY)-3-((2,6-DIDEOXY-3-O-METHYL-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.,5.BETA.,16.BETA.)-; Card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3-beta,5-beta,16-beta)-; Card-20(22)-enolide, 16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy)-14-hydroxy-, (3beta,5beta,16beta)-; (3beta,5beta,16beta)-16-(acetyloxy)-3-[(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy]-14-hydroxy-card-20(22)-enolide; (3beta,5beta,16beta)-16-acetoxy-3-[(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide; (3beta,5beta,16beta)-16-acetoxy-3-((2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)oxy)-14-hydroxycard-20(22)-enolide; (3 beta,16 beta)-16-(acetyloxy)-3-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide; (3beta,16beta)-16-(Acetyloxy)-3-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxy card-20(22)-enolide; 16beta-(Acetyloxy)-3beta-((2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyl)oxy)-14-hydroxycard-20-(22)-enolide; 16beta-Acetoxy-3beta-(2,6-dideoxy-3-O-methyl-L-arabino-hexopyranosyloxy)-14-hydroxycard-20(22)-enolide; (3beta,5beta,16beta)-16-(Acetyloxy)-3-; Oleandrigenin oleandroside; Oleandrin, >=98\\% (HPLC); Oleandrina [Spanish]; OLEANDRIN [WHO-DD]; UNII-II95UDU7I4; OLEANDRIN [MI]; II95UDU7I4; Oleandrina; Foliandrin; Neriostene; Oleandrine; Folinevin; Oleandrin; Folinerin; Neriolin; Corrigen; Anvirzel; Neriol; NSC254670; PBI-05204; Oleandrin



数据库引用编号

30 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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INOH(0)

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30 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

  • Canan Eroğlu Güneş, Fatma Seçer Çelik, Mücahit Seçme, Levent Elmas, Yavuz Dodurga, Ercan Kurar. Glycoside oleandrin downregulates toll-like receptor pathway genes and associated miRNAs in human melanoma cells. Gene. 2022 Nov; 843(?):146805. doi: 10.1016/j.gene.2022.146805. [PMID: 35964872]
  • Robert A Newman, Christopher C L Chase, Jose R Matos, Karim Abdelsalam, Robin Buterbaugh, Sonja Van Holland, Hadia Abdelaal, Amelia Woolum, K Jagannadha Sastry. Efficacy of oleandrin and PBI-05204 against bovine viruses of importance to commercial cattle health. Antiviral chemistry & chemotherapy. 2022 Jan; 30(?):20402066221103960. doi: 10.1177/20402066221103960. [PMID: 35611441]
  • C Combe, J Guitton, A Daudé, T Le Bricon, N Guibert, C Bosset, T Girardot. [Multidisciplinary management of voluntary pink oleander poisoning: How to estimate the quantities ingested?]. Annales pharmaceutiques francaises. 2022 Jan; 80(1):76-80. doi: 10.1016/j.pharma.2021.04.003. [PMID: 33878309]
  • Kenneth S Plante, Varun Dwivedi, Jessica A Plante, Diana Fernandez, Divya Mirchandani, Nathen Bopp, Patricia V Aguilar, Jun-Gyu Park, Paula Pino Tamayo, Jennifer Delgado, Vinay Shivanna, Jordi B Torrelles, Luis Martinez-Sobrido, Rick Matos, Scott C Weaver, K Jagannadha Sastry, Robert A Newman. Antiviral activity of oleandrin and a defined extract of Nerium oleander against SARS-CoV-2. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Jun; 138(?):111457. doi: 10.1016/j.biopha.2021.111457. [PMID: 33721754]
  • Anna Carfora, Raffaella Petrella, Renata Borriello, Lucia Aventaggiato, Roberto Gagliano-Candela, Carlo Pietro Campobasso. Fatal poisoning by ingestion of a self-prepared oleander leaf infusion. Forensic science, medicine, and pathology. 2021 Mar; 17(1):120-125. doi: 10.1007/s12024-020-00338-w. [PMID: 33237522]
  • Jeffrey Suchard, Alexandra Greb. Negligible Oleandrin Content of Hot Dogs Cooked on Nerium oleander Skewers. Journal of medical toxicology : official journal of the American College of Medical Toxicology. 2021 01; 17(1):57-60. doi: 10.1007/s13181-020-00805-4. [PMID: 32803693]
  • Ana F M Botelho, Ana L S Miranda, Thalita G Freitas, Paula F Milani, Tatiane Barreto, Jáder S Cruz, Marília M Melo. Comparative Cardiotoxicity of Low Doses of Digoxin, Ouabain, and Oleandrin. Cardiovascular toxicology. 2020 12; 20(6):539-547. doi: 10.1007/s12012-020-09579-1. [PMID: 32488807]
  • Marc T Roth, Dana Backlund Cardin, Erkut Hasan Borazanci, Margaux Steinbach, Vincent J Picozzi, Alexander Rosemury, Raymond Couric Wadlow, Robert A Newman, Jordan Berlin. A Phase II, Single-Arm, Open-Label, Bayesian Adaptive Efficacy and Safety Study of PBI-05204 in Patients with Stage IV Metastatic Pancreatic Adenocarcinoma. The oncologist. 2020 10; 25(10):e1446-e1450. doi: 10.1634/theoncologist.2020-0440. [PMID: 32452588]
  • Lavinia L Ruta, Claudia V Popa, Ileana C Farcasanu. Cytotoxicity of Oleandrin Is Mediated by Calcium Influx and by Increased Manganese Uptake in Saccharomyces cerevisiae Cells. Molecules (Basel, Switzerland). 2020 Sep; 25(18):. doi: 10.3390/molecules25184259. [PMID: 32957533]
  • Nazia Kanwal, Azhar Rasul, Ghulam Hussain, Haseeb Anwar, Muhammad Ajmal Shah, Iqra Sarfraz, Ammara Riaz, Rabia Batool, Muhammad Shahbaz, Arif Hussain, Zeliha Selamoglu. Oleandrin: A bioactive phytochemical and potential cancer killer via multiple cellular signaling pathways. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Sep; 143(?):111570. doi: 10.1016/j.fct.2020.111570. [PMID: 32640345]
  • Luigi Ceci, Flavia Girolami, Maria Teresa Capucchio, Elena Colombino, Carlo Nebbia, Fabio Gosetti, Emilio Marengo, Fabrizio Iarussi, Grazia Carelli. Outbreak of Oleander (Nerium oleander) Poisoning in Dairy Cattle: Clinical and Food Safety Implications. Toxins. 2020 07; 12(8):. doi: 10.3390/toxins12080471. [PMID: 32722138]
  • Yanzhi Zhang, Xubing Chen, Yang Zhou, Jinjun Hou, Huali Long, Zijia Zhang, Min Lei, Wanying Wu. Synthesis of oleandrin derivatives and their cytotoxic activity. Steroids. 2020 07; 159(?):108650. doi: 10.1016/j.steroids.2020.108650. [PMID: 32360418]
  • Svetlana V Malysheva, Patrick P J Mulder, Julien Masquelier. Development and Validation of a UHPLC-ESI-MS/MS Method for Quantification of Oleandrin and Other Cardiac Glycosides and Evaluation of Their Levels in Herbs and Spices from the Belgian Market. Toxins. 2020 04; 12(4):. doi: 10.3390/toxins12040243. [PMID: 32283845]
  • Giorgia Montrucchio, Stefano Bosso, Martina Scanu, Andrea Mina, Maria R Imeneo, Luca Brazzi. Oleander poisoning: an old toxic in the modern era. Minerva anestesiologica. 2020 03; 86(3):355-356. doi: 10.23736/s0375-9393.19.14066-7. [PMID: 31818086]
  • Cui Zhou, Fangjun Yu, Peng Zeng, Tianpeng Zhang, Hao Huang, Wenying Chen, Baojian Wu. Circadian sensitivity to the cardiac glycoside oleandrin is associated with diurnal intestinal P-glycoprotein expression. Biochemical pharmacology. 2019 11; 169(?):113622. doi: 10.1016/j.bcp.2019.08.024. [PMID: 31472126]
  • Silva Rubini, Sabina Strano Rossi, Serena Mestria, Sara Odoardi, Sara Chendi, Andrea Poli, Giuseppe Merialdi, Giuseppina Andreoli, Paolo Frisoni, Rosa Maria Gaudio, Anna Baldisserotto, Piergiacomo Buso, Stefano Manfredini, Guido Govoni, Stefania Barbieri, Cinzia Centelleghe, Giorgia Corazzola, Sandro Mazzariol, Carlo Alessandro Locatelli. A Probable Fatal Case of Oleander (Nerium oleander) Poisoning on a Cattle Farm: A New Method of Detection and Quantification of the Oleandrin Toxin in Rumen. Toxins. 2019 07; 11(8):. doi: 10.3390/toxins11080442. [PMID: 31349685]
  • Elena Azzalini, Marzia Bernini, Sara Vezzoli, Anna Antonietti, Andrea Verzeletti. A fatal case of self-poisoning through the ingestion of oleander leaves. Journal of forensic and legal medicine. 2019 Jul; 65(?):133-136. doi: 10.1016/j.jflm.2019.05.016. [PMID: 31153008]
  • J X Zhai, H Yan, M Shen, B H Shen, W Liu. Determination of Oleandrin in Blood and Liver Samples by LC-MS/MS. Fa yi xue za zhi. 2018 Jun; 34(6):585-589. doi: 10.12116/j.issn.1004-5619.2018.06.002. [PMID: 30896093]
  • 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]
  • Michael J Van Kanegan, Denise E Dunn, Linda S Kaltenbach, Bijal Shah, Dong Ning He, Daniel D McCoy, Peiying Yang, Jiangnan Peng, Li Shen, Lin Du, Robert H Cichewicz, Robert A Newman, Donald C Lo. Dual activities of the anti-cancer drug candidate PBI-05204 provide neuroprotection in brain slice models for neurodegenerative diseases and stroke. Scientific reports. 2016 05; 6(?):25626. doi: 10.1038/srep25626. [PMID: 27172999]
  • José Manuel Calderón-Montaño, Estefanía Burgos-Morón, Emilio Guillén-Mancina, Miguel López-Lázaro. Does the Nerium oleander extract PBI-05204 have potential for pancreatic cancer therapy?. Investigational new drugs. 2015 Jun; 33(3):787. doi: 10.1007/s10637-014-0204-4. [PMID: 25698441]
  • D S Hong, H Henary, G S Falchook, A Naing, S Fu, S Moulder, J J Wheler, A Tsimberidou, J B Durand, R Khan, P Yang, M Johansen, R A Newman, R Kurzrock. First-in-human study of pbi-05204, an oleander-derived inhibitor of akt, fgf-2, nf-κΒ and p70s6k, in patients with advanced solid tumors. Investigational new drugs. 2014 Dec; 32(6):1204-12. doi: 10.1007/s10637-014-0127-0. [PMID: 24919855]
  • S L Fink, T E Robey, A F Tarabar, M E Hodsdon. Rapid detection of convallatoxin using five digoxin immunoassays. Clinical toxicology (Philadelphia, Pa.). 2014 Aug; 52(7):659-63. doi: 10.3109/15563650.2014.932366. [PMID: 24980812]
  • Nune Raviprakash, Sunil Kumar Manna. Short-term exposure to oleandrin enhances responses to IL-8 by increasing cell surface IL-8 receptors. British journal of pharmacology. 2014 Jul; 171(14):3339-51. doi: 10.1111/bph.12493. [PMID: 24172227]
  • Michael J Van Kanegan, Dong Ning He, Denise E Dunn, Peiying Yang, Robert A Newman, Anne E West, Donald C Lo. BDNF mediates neuroprotection against oxygen-glucose deprivation by the cardiac glycoside oleandrin. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2014 Jan; 34(3):963-8. doi: 10.1523/jneurosci.2700-13.2014. [PMID: 24431454]
  • Amitava Dasgupta, Kerry J Welsh, Shen-An Hwang, Myrtle Johnson, Jeffrey K Actor. Bidirectional (negative/positive) interference of oleandrin and oleander extract on a relatively new Loci digoxin assay using Vista 1500 analyzer. Journal of clinical laboratory analysis. 2014 Jan; 28(1):16-20. doi: 10.1002/jcla.21637. [PMID: 24375780]
  • Bina Shaheen Siddiqui, Nasima Khatoon, Sabira Begum, Ahsana Dar Farooq, Kehkashan Qamar, Huma Aslam Bhatti, Syed Kashif Ali. Flavonoid and cardenolide glycosides and a pentacyclic triterpene from the leaves of Nerium oleander and evaluation of cytotoxicity. Phytochemistry. 2012 May; 77(?):238-44. doi: 10.1016/j.phytochem.2012.01.001. [PMID: 22281382]
  • Luigi Papi, Alessandro Bassi Luciani, David Forni, Mario Giusiani. Unexpected double lethal oleander poisoning. The American journal of forensic medicine and pathology. 2012 Mar; 33(1):93-7. doi: 10.1097/paf.0b013e31822d33d4. [PMID: 21926903]
  • Heidrun Weidemann. 'The Lower Threshold' phenomenon in tumor cells toward endogenous digitalis-like compounds: Responsible for tumorigenesis?. Journal of carcinogenesis. 2012; 11(?):2. doi: 10.4103/1477-3163.92999. [PMID: 22438768]
  • Faizah Bt Harun, Syed Mohsin Syed Sahil Jamalullail, Khoo Boon Yin, Zulkhairi Othman, Anita Tilwari, Prabha Balaram. Autophagic cell death is induced by acetone and ethyl acetate extracts from Eupatorium odoratum in vitro: effects on MCF-7 and vero cell lines. TheScientificWorldJournal. 2012; 2012(?):439479. doi: 10.1100/2012/439479. [PMID: 22666123]
  • Gabriele Multhoff, Jürgen Radons. Radiation, inflammation, and immune responses in cancer. Frontiers in oncology. 2012; 2(?):58. doi: 10.3389/fonc.2012.00058. [PMID: 22675673]
  • Aryamitra A Banerjee, Kamala K Vasu, Harit Pancholi, Mandapati Rajani, Manish A Nivsarkar. Detoxification of Nerium indicum roots based on Indian system of medicine: phytochemical and toxicity evaluations. Acta poloniae pharmaceutica. 2011 Nov; 68(6):905-11. doi: ". [PMID: 22125956]
  • Jing Liu, Ye Zhang, Jinglei Qu, Ling Xu, Kezuo Hou, Jingdong Zhang, Xiujuan Qu, Yunpeng Liu. β-Elemene-induced autophagy protects human gastric cancer cells from undergoing apoptosis. BMC cancer. 2011 May; 11(?):183. doi: 10.1186/1471-2407-11-183. [PMID: 21595977]
  • Amitava Dasgupta, Kimberley Klein, Semyon A Risin, Jeffrey K Actor. Rapid detection of oleander poisoning by Dimension Vista digoxin assay (Flex Reagent Cartridge). Journal of clinical laboratory analysis. 2011; 25(2):105-9. doi: 10.1002/jcla.20441. [PMID: 21438002]
  • Veronika Bandara, Scott A Weinstein, Julian White, Michael Eddleston. A review of the natural history, toxinology, diagnosis and clinical management of Nerium oleander (common oleander) and Thevetia peruviana (yellow oleander) poisoning. Toxicon : official journal of the International Society on Toxinology. 2010 Sep; 56(3):273-81. doi: 10.1016/j.toxicon.2010.03.026. [PMID: 20438743]
  • Mohd Suhail. Na, K-ATPase: Ubiquitous Multifunctional Transmembrane Protein and its Relevance to Various Pathophysiological Conditions. Journal of clinical medicine research. 2010 Feb; 2(1):1-17. doi: 10.4021/jocmr2010.02.263w. [PMID: 22457695]
  • Behçet Al, Pınar Yarbil, Mehmet Dogan, Sinem Kabul, Cuma Yıldırım. A case of non-fatal oleander poisoning. BMJ case reports. 2010; 2010(?):. doi: 10.1136/bcr.02.2009.1573. [PMID: 22328901]
  • Jenny Felth, Linda Rickardson, Josefin Rosén, Malin Wickström, Mårten Fryknäs, Magnus Lindskog, Lars Bohlin, Joachim Gullbo. Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs. Journal of natural products. 2009 Nov; 72(11):1969-74. doi: 10.1021/np900210m. [PMID: 19894733]
  • Tania A Kozikowski, K Gary Magdesian, Birgit Puschner. Oleander intoxication in New World camelids: 12 cases (1995-2006). Journal of the American Veterinary Medical Association. 2009 Aug; 235(3):305-10. doi: 10.2460/javma.235.3.305. [PMID: 19650704]
  • Peiying Yang, David G Menter, Carrie Cartwright, Diana Chan, Susan Dixon, Milind Suraokar, Gabriela Mendoza, Norma Llansa, Robert A Newman. Oleandrin-mediated inhibition of human tumor cell proliferation: importance of Na,K-ATPase alpha subunits as drug targets. Molecular cancer therapeutics. 2009 Aug; 8(8):2319-28. doi: 10.1158/1535-7163.mct-08-1085. [PMID: 19671733]
  • Asheesh K Tiwary, Robert H Poppenga, Birgit Puschner. In vitro study of the effectiveness of three commercial adsorbents for binding oleander toxins. Clinical toxicology (Philadelphia, Pa.). 2009 Mar; 47(3):213-8. doi: 10.1080/15563650802590314. [PMID: 19274509]
  • Preetha Anand, Ajaikumar B Kunnumakkara, Ajaikumar B Kunnumakara, Chitra Sundaram, Kuzhuvelil B Harikumar, Sheeja T Tharakan, Oiki S Lai, Bokyung Sung, Bharat B Aggarwal. Cancer is a preventable disease that requires major lifestyle changes. Pharmaceutical research. 2008 Sep; 25(9):2097-116. doi: 10.1007/s11095-008-9661-9. [PMID: 18626751]
  • Ibrahim A Wasfi, Omar Zorob, Nawal A Al katheeri, Anwar M Al Awadhi. A fatal case of oleandrin poisoning. Forensic science international. 2008 Aug; 179(2-3):e31-6. doi: 10.1016/j.forsciint.2008.05.002. [PMID: 18602779]
  • Amitava Dasgupta, Semyon A Risin, Meredith Reyes, Jeffrey K Actor. Rapid detection of oleander poisoning by Digoxin III, a new Digoxin assay: impact on serum Digoxin measurement. American journal of clinical pathology. 2008 Apr; 129(4):548-53. doi: 10.1309/cc6791dff20qpcx3. [PMID: 18343781]
  • Robert A Newman, Yasuko Kondo, Tomohisa Yokoyama, Susan Dixon, Carrie Cartwright, Diana Chan, Mary Johansen, Peiying Yang. Autophagic cell death of human pancreatic tumor cells mediated by oleandrin, a lipid-soluble cardiac glycoside. Integrative cancer therapies. 2007 Dec; 6(4):354-64. doi: 10.1177/1534735407309623. [PMID: 18048883]
  • Amitava Dasgupta, Dollett White. Stability of oleander extract and oleandrin in sera stored in plastic serum separator tubes. Annals of clinical biochemistry. 2007 Sep; 44(Pt 5):485-7. doi: 10.1258/000456307781646003. [PMID: 17761037]
  • Wilhelm Schoner, Georgios Scheiner-Bobis. Endogenous and exogenous cardiac glycosides: their roles in hypertension, salt metabolism, and cell growth. American journal of physiology. Cell physiology. 2007 Aug; 293(2):C509-36. doi: 10.1152/ajpcell.00098.2007. [PMID: 17494630]
  • Brian J Poindexter, Wei Feng, Amitava Dasgupta, Roger J Bick. Oleandrin produces changes in intracellular calcium levels in isolated cardiomyocytes: a real-time fluorescence imaging study comparing adult to neonatal cardiomyocytes. Journal of toxicology and environmental health. Part A. 2007 Mar; 70(6):568-74. doi: 10.1080/15287390600882408. [PMID: 17365610]
  • Pongali B Raghavendra, Yashin Sreenivasan, Sunil K Manna. Oleandrin induces apoptosis in human, but not in murine cells: dephosphorylation of Akt, expression of FasL, and alteration of membrane fluidity. Molecular immunology. 2007 Mar; 44(9):2292-302. doi: 10.1016/j.molimm.2006.11.009. [PMID: 17173971]
  • Pongali B Raghavendra, Yashin Sreenivasan, Govindarajan T Ramesh, Sunil K Manna. Cardiac glycoside induces cell death via FasL by activating calcineurin and NF-AT, but apoptosis initially proceeds through activation of caspases. Apoptosis : an international journal on programmed cell death. 2007 Feb; 12(2):307-18. doi: 10.1007/s10495-006-0626-3. [PMID: 17203245]
  • ". Nerium oleander (Oleandrin). Journal of the Society for Integrative Oncology. 2007; 5(1):43-4. doi: ". [PMID: 17309813]
  • Cecilia Gechtman, Federico Guidugli, Alessandro Marocchi, Adriano Masarin, Francesco Zoppi. Unexpectedly dangerous escargot stew: oleandrin poisoning through the alimentary chain. Journal of analytical toxicology. 2006 Nov; 30(9):683-6. doi: 10.1093/jat/30.9.683. [PMID: 17137529]
  • Nguyen-Hai Nam. Naturally occurring NF-kappaB inhibitors. Mini reviews in medicinal chemistry. 2006 Aug; 6(8):945-51. doi: 10.2174/138955706777934937. [PMID: 16918500]
  • Sunil K Manna, Yashin Sreenivasan, Abira Sarkar. Cardiac glycoside inhibits IL-8-induced biological responses by downregulating IL-8 receptors through altering membrane fluidity. Journal of cellular physiology. 2006 Apr; 207(1):195-207. doi: 10.1002/jcp.20555. [PMID: 16331685]
  • Amitava Dasgupta, Edward Kang, Pradip Datta. The new enzyme-linked immunosorbent digoxin assay on the ADVIA Integrated Modular System is virtually free from oleander interference. Therapeutic drug monitoring. 2006 Apr; 28(2):282-5. doi: 10.1097/01.ftd.0000195616.69721.ec. [PMID: 16628146]
  • Nevruz Turan, Kadriye Akgün-Dar, Serap Erdem Kuruca, Tülay Kiliçaslan-Ayna, Vildan G Seyhan, Belkis Atasever, Filiz Meriçli, Mahmut Carin. Cytotoxic effects of leaf, stem and root extracts of Nerium oleander on leukemia cell lines and role of the p-glycoprotein in this effect. Journal of experimental therapeutics & oncology. 2006; 6(1):31-8. doi: ". [PMID: 17228522]
  • Amit K Garg, Thomas A Buchholz, Bharat B Aggarwal. Chemosensitization and radiosensitization of tumors by plant polyphenols. Antioxidants & redox signaling. 2005 Nov; 7(11-12):1630-47. doi: 10.1089/ars.2005.7.1630. [PMID: 16356126]
  • J Pietsch, R Oertel, S Trautmann, K Schulz, B Kopp, J Dressler. A non-fatal oleander poisoning. International journal of legal medicine. 2005 Jul; 119(4):236-40. doi: 10.1007/s00414-005-0548-6. [PMID: 15906057]
  • Elizabeth R Tor, Michael S Filigenzi, Birgit Puschner. Determination of oleandrin in tissues and biological fluids by liquid chromatography-electrospray tandem mass spectrometry. Journal of agricultural and food chemistry. 2005 Jun; 53(11):4322-5. doi: 10.1021/jf050201s. [PMID: 15913289]
  • Amitava Dasgupta, Pradip Datta. Rapid detection of oleander poisoning using digoxin immunoassays: comparison of five assays. Therapeutic drug monitoring. 2004 Dec; 26(6):658-63. doi: 10.1097/00007691-200412000-00012. [PMID: 15570191]
  • Wojciech Wojtyna, Frank Enseleit. A rare cause of complete heart block after transdermal botanical treatment for psoriasis. Pacing and clinical electrophysiology : PACE. 2004 Dec; 27(12):1686-8. doi: 10.1111/j.1540-8159.2004.00704.x. [PMID: 15613134]
  • Sudhanshu Tiwari, Ajay Singh. Toxic and sub-lethal effects of oleandrin on biochemical parameters of fresh water air breathing murrel, Channa punctatus (Bloch.). Indian journal of experimental biology. 2004 Apr; 42(4):413-8. doi: . [PMID: 15088692]
  • Yashin Sreenivasan, Abira Sarkar, Sunil Kumar Manna. Oleandrin suppresses activation of nuclear transcription factor-kappa B and activator protein-1 and potentiates apoptosis induced by ceramide. Biochemical pharmacology. 2003 Dec; 66(11):2223-39. doi: 10.1016/j.bcp.2003.07.010. [PMID: 14609747]
  • Ming Yao, Hongjian Zhang, Saeho Chong, Mingshe Zhu, Richard A Morrison. A rapid and sensitive LC/MS/MS assay for quantitative determination of digoxin in rat plasma. Journal of pharmaceutical and biomedical analysis. 2003 Aug; 32(6):1189-97. doi: 10.1016/s0731-7085(03)00050-5. [PMID: 12907263]
  • Amitava Dasgupta, Shinian Cao, Alice Wells. Activated charcoal is effective but equilibrium dialysis is ineffective in removing oleander leaf extract and oleandrin from human serum: monitoring the effect by measuring apparent digoxin concentration. Therapeutic drug monitoring. 2003 Jun; 25(3):323-30. doi: 10.1097/00007691-200306000-00013. [PMID: 12766561]
  • Sachiko Nasu, Luka Milas, Shinichiro Kawabe, Uma Raju, Robert Newman. Enhancement of radiotherapy by oleandrin is a caspase-3 dependent process. Cancer letters. 2002 Nov; 185(2):145-51. doi: 10.1016/s0304-3835(02)00263-x. [PMID: 12169388]
  • Kimio Hamad, Asako Iwamoto, Shigeru Miyazaki, Noriko Yamanaka, Keerthi Siri Guruge. Determination of bovine blood oleandrin by high-performance liquid chromatography and postcolumn derivatization. Journal of chromatographic science. 2002 Oct; 40(9):515-8. doi: 10.1093/chromsci/40.9.555. [PMID: 12433114]
  • Dan Ni, Timothy L Madden, Mary Johansen, Edward Felix, Dah H Ho, Robert A Newman. Murine pharmacokinetics and metabolism of oleandrin, a cytotoxic component of Nerium oleander. Journal of experimental therapeutics & oncology. 2002 Sep; 2(5):278-85. doi: 10.1046/j.1359-4117.2002.01052.x. [PMID: 12416031]
  • Tomonori Arao, Chiaki Fuke, Hajime Takaesu, Masakazu Nakamoto, Yasumasa Morinaga, Tetsuji Miyazaki. Simultaneous determination of cardenolides by sonic spray ionization liquid chromatography-ion trap mass spectrometry--a fatal case of oleander poisoning. Journal of analytical toxicology. 2002 May; 26(4):222-7. doi: 10.1093/jat/26.4.222. [PMID: 12054363]
  • J A Smith, T Madden, M Vijjeswarapu, R A Newman. Inhibition of export of fibroblast growth factor-2 (FGF-2) from the prostate cancer cell lines PC3 and DU145 by Anvirzel and its cardiac glycoside component, oleandrin. Biochemical pharmacology. 2001 Aug; 62(4):469-72. doi: 10.1016/s0006-2952(01)00690-6. [PMID: 11448457]
  • X Wang, J B Plomley, R A Newman, A Cisneros. LC/MS/MS analyses of an oleander extract for cancer treatment. Analytical chemistry. 2000 Aug; 72(15):3547-52. doi: 10.1021/ac991425a. [PMID: 10952541]
  • S K Manna, N K Sah, R A Newman, A Cisneros, B B Aggarwal. Oleandrin suppresses activation of nuclear transcription factor-kappaB, activator protein-1, and c-Jun NH2-terminal kinase. Cancer research. 2000 Jul; 60(14):3838-47. doi: . [PMID: 10919658]
  • D J McConkey, Y Lin, L K Nutt, H Z Ozel, R A Newman. Cardiac glycosides stimulate Ca2+ increases and apoptosis in androgen-independent, metastatic human prostate adenocarcinoma cells. Cancer research. 2000 Jul; 60(14):3807-12. doi: . [PMID: 10919654]
  • S Pathak, A S Multani, S Narayan, V Kumar, R A Newman. Anvirzel, an extract of Nerium oleander, induces cell death in human but not murine cancer cells. Anti-cancer drugs. 2000 Jul; 11(6):455-63. doi: 10.1097/00001813-200007000-00006. [PMID: 11001386]
  • S Singh, D K Singh. Effect of molluscicidal components of Abrus precatorius, Argemone mexicana and Nerium indicum on certain biochemical parameters of Lymnaea acuminata. Phytotherapy research : PTR. 1999 May; 13(3):210-3. doi: 10.1002/(sici)1099-1573(199905)13:3<210::aid-ptr421>3.0.co;2-f. [PMID: 10353159]
  • A Dasgupta, J Scott. Unexpected suppression of total digoxin concentrations by cross-reactants in the microparticle enzyme immunoassay: elimination of interference by monitoring free digoxin concentration. American journal of clinical pathology. 1998 Jul; 110(1):78-82. doi: 10.1093/ajcp/110.1.78. [PMID: 9661925]
  • A Tracqui, P Kintz, F Branche, B Ludes. Confirmation of oleander poisoning by HPLC/MS. International journal of legal medicine. 1998; 111(1):32-4. doi: 10.1007/s004140050107. [PMID: 9457536]
  • A Dasgupta, L Emerson. Neutralization of cardiac toxins oleandrin, oleandrigenin, bufalin, and cinobufotalin by digibind: monitoring the effect by measuring free digitoxin concentrations. Life sciences. 1998; 63(9):781-8. doi: 10.1016/s0024-3205(98)00333-6. [PMID: 9740315]
  • A Gupta, P Joshi, S A Jortani, R Valdes, T Thorkelsson, Z Verjee, S Shemie. A case of nondigitalis cardiac glycoside toxicity. Therapeutic drug monitoring. 1997 Dec; 19(6):711-4. doi: 10.1097/00007691-199712000-00018. [PMID: 9421116]
  • A Dasgupta, A P Hart. Rapid detection of oleander poisoning using fluorescence polarization immunoassay for digitoxin. Effect of treatment with digoxin-specific Fab antibody fragment (ovine). American journal of clinical pathology. 1997 Oct; 108(4):411-6. doi: 10.1093/ajcp/108.4.411. [PMID: 9322594]
  • P Datta, A Dasgupta. Interference of oleandrin and oleandrigenin in digitoxin immunoassays: minimal cross reactivity with a new monoclonal chemiluminescent assay and high cross reactivity with the fluorescence polarization assay. Therapeutic drug monitoring. 1997 Aug; 19(4):465-9. doi: 10.1097/00007691-199708000-00017. [PMID: 9263390]
  • S A Jortani, R A Helm, R Valdes. Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clinical chemistry. 1996 Oct; 42(10):1654-8. doi: . [PMID: 8855150]
  • Z Durakovic, A Durakovic, S Durakovic. Oleander poisoning treated by resin haemoperfusion. Journal of the Indian Medical Association. 1996 Apr; 94(4):149-50. doi: ". [PMID: 8854633]
  • G Rule, L G McLaughlin, J Henion. A quest for oleandrin in decayed human tissue. Analytical chemistry. 1993 Oct; 65(19):857A-863A. doi: 10.1021/ac00067a727. [PMID: 8238947]
  • L M Blum, F Rieders. Oleandrin distribution in a fatality from rectal and oral Nerium oleander extract administration. Journal of analytical toxicology. 1987 Sep; 11(5):219-21. doi: 10.1093/jat/11.5.219. [PMID: 3682781]
  • J Osterloh, S Herold, S Pond. Oleander interference in the digoxin radioimmunoassay in a fatal ingestion. JAMA. 1982 Mar; 247(11):1596-7. doi: NULL. [PMID: 7038154]