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Effective URL: https://passwordupdate1e.z13.web.core.windows.net/
Submission: On January 07 via manual from IN — Scanned from CA
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</tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div>
<p><b>Atractyloside</b> (ATR) is a natural, toxic <a href="/wiki/Glycoside" title="Glycoside">glycoside</a> present in numerous plant species worldwide in the <a href="/wiki/Daisy_family" class="mw-redirect" title="Daisy family">daisy family</a> including <i><a href="/wiki/Atractylis_gummifera" class="mw-redirect" title="Atractylis gummifera">Atractylis gummifera</a></i> and <i><a href="/w/index.php?title=Callilepis_laureola&action=edit&redlink=1" class="new" title="Callilepis laureola (page does not exist)">Callilepis laureola</a></i>,<sup id="cite_ref-Obatomi1998_1-0" class="reference"><a href="#cite_note-Obatomi1998-1">[1]</a></sup> and it's used for a variety of therapeutic, religious, and toxic purposes.<sup id="cite_ref-Stewart2000_2-0" class="reference"><a href="#cite_note-Stewart2000-2">[2]</a></sup> Exposure to ATR via ingestion or physical contact is toxic and can be fatal for both humans and animals, especially by kidney and liver failure.<sup id="cite_ref-Daniele2005_3-0" class="reference"><a href="#cite_note-Daniele2005-3">[3]</a></sup> ATR acts as an effective <a href="/wiki/ADP/ATP_translocase" class="mw-redirect" title="ADP/ATP translocase">ADP/ATP translocase</a> inhibitor which eventually halts ADP and ATP exchange and the cell dies due to lack of energy. Historically, atractyloside poisoning has been challenging to verify and quantify toxicologically, though recent literature has described such methods within acceptable standards of forensic science.<sup id="cite_ref-Carlier2014_4-0" class="reference"><a href="#cite_note-Carlier2014-4">[4]</a></sup>
</p>
<div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none" /><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><span class="toctogglespan"><label class="toctogglelabel" for="toctogglecheckbox"></label></span></div>
<ul>
<li class="toclevel-1 tocsection-1"><a href="#Sources"><span class="tocnumber">1</span> <span class="toctext">Sources</span></a></li>
<li class="toclevel-1 tocsection-2"><a href="#History"><span class="tocnumber">2</span> <span class="toctext">History</span></a></li>
<li class="toclevel-1 tocsection-3"><a href="#Structure_and_reactivity"><span class="tocnumber">3</span> <span class="toctext">Structure and reactivity</span></a></li>
<li class="toclevel-1 tocsection-4"><a href="#Mechanism_of_action"><span class="tocnumber">4</span> <span class="toctext">Mechanism of action</span></a></li>
<li class="toclevel-1 tocsection-5"><a href="#Poisoning"><span class="tocnumber">5</span> <span class="toctext">Poisoning</span></a>
<ul>
<li class="toclevel-2 tocsection-6"><a href="#Symptoms"><span class="tocnumber">5.1</span> <span class="toctext">Symptoms</span></a></li>
<li class="toclevel-2 tocsection-7"><a href="#Identification_/_Quantification"><span class="tocnumber">5.2</span> <span class="toctext">Identification / Quantification</span></a></li>
<li class="toclevel-2 tocsection-8"><a href="#Lethality"><span class="tocnumber">5.3</span> <span class="toctext">Lethality</span></a></li>
</ul>
</li>
<li class="toclevel-1 tocsection-9"><a href="#See_also"><span class="tocnumber">6</span> <span class="toctext">See also</span></a></li>
<li class="toclevel-1 tocsection-10"><a href="#References"><span class="tocnumber">7</span> <span class="toctext">References</span></a></li>
</ul>
</div>
<h2><span class="mw-headline" id="Sources">Sources</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=1" title="Edit section: Sources">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
<div class="thumb tleft"><div class="thumbinner" style="width:222px;"><a href="/wiki/File:Atractylis_gummifera.jpg" class="image"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Atractylis_gummifera.jpg/220px-Atractylis_gummifera.jpg" decoding="async" width="220" height="165" class="thumbimage" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Atractylis_gummifera.jpg/330px-Atractylis_gummifera.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Atractylis_gummifera.jpg/440px-Atractylis_gummifera.jpg 2x" data-file-width="1280" data-file-height="960" /></a> <div class="thumbcaption"><div class="magnify"><a href="/wiki/File:Atractylis_gummifera.jpg" class="internal" title="Enlarge"></a></div>Distaff thistle (<i><a href="/wiki/Atractylis_gummifera" class="mw-redirect" title="Atractylis gummifera">Atractylis gummifera</a></i>) contains atractyloside</div></div></div>
<p>Atractyloside is found in numerous plant species in the <a href="/wiki/Daisy_family" class="mw-redirect" title="Daisy family">daisy family</a> e.g. <i><a href="/wiki/Atractylis_gummifera" class="mw-redirect" title="Atractylis gummifera">Atractylis gummifera</a></i>, <i><a href="/w/index.php?title=Callilepis_laureola&action=edit&redlink=1" class="new" title="Callilepis laureola (page does not exist)">Callilepis laureola</a></i>, <i><a href="/wiki/Xanthium_strumarium" title="Xanthium strumarium">Xanthium strumarium</a></i>, <i><a href="/w/index.php?title=Iphiona_alsoeri&action=edit&redlink=1" class="new" title="Iphiona alsoeri (page does not exist)">Iphiona alsoeri</a></i>, <i><a href="/w/index.php?title=Pascalia_glauca&action=edit&redlink=1" class="new" title="Pascalia glauca (page does not exist)">Pascalia glauca</a></i>, <i><a href="/w/index.php?title=Wedelia_glauca&action=edit&redlink=1" class="new" title="Wedelia glauca (page does not exist)">Wedelia glauca</a></i>, and <i><a href="/w/index.php?title=Iphiona_aucheri&action=edit&redlink=1" class="new" title="Iphiona aucheri (page does not exist)">Iphiona aucheri</a></i> among others. It is also found in very low concentrations in <i><a href="/wiki/Coffea_arabica" title="Coffea arabica">Coffea arabica</a></i>.<sup id="cite_ref-Obatomi1998_1-1" class="reference"><a href="#cite_note-Obatomi1998-1">[1]</a></sup>
</p><p>The widespread regions across all of these plants' native areas of growth results in ATR's easy availability worldwide.
</p><p>However the ATR concentration found in plants is dependent upon the species, season, and origin. For example, the ATR content measured in dried Atractlyis gummifera between Sardinia, Italy and Sicily, Italy revealed a higher content in the Sicilian region by nearly a factor of five, and a higher content in colder months across both regions.<sup id="cite_ref-Daniele2005_3-1" class="reference"><a href="#cite_note-Daniele2005-3">[3]</a></sup>
</p><p>Additionally, the preparation of plants with atractyloside in some traditional medicines affects the atractyloside content. The preparation technique, such as <a href="/wiki/Decoction" title="Decoction">decoction</a> or <a href="/wiki/Infusion" title="Infusion">infusion</a>, extracts the desired chemical compound, after which the contents could be diluted or concentrated.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5">[5]</a></sup>
</p>
<h2><span class="mw-headline" id="History">History</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=2" title="Edit section: History">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
<p>Atractylosides have been used as poisons since at least 100 AD, though it was not isolated and characterized until 1868 by LeFranc, after extracting it from <i><a href="/wiki/Atractylis_gummifera" class="mw-redirect" title="Atractylis gummifera">Atractylis gummifera</a></i>.<sup id="cite_ref-Lefranc_6-0" class="reference"><a href="#cite_note-Lefranc-6">[6]</a></sup><sup id="cite_ref-Stewart2000_2-1" class="reference"><a href="#cite_note-Stewart2000-2">[2]</a></sup> After high-profile accidental poisonings—children in Italy and Algeria ate parts of the plant in 1955 and 1975, respectively—renewed interest in atractyloside resulted in future research.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7">[7]</a></sup>
</p><p>Historically, the ATR plant sources have been used for numerous reasons: whether for its therapeutic properties, magico-religious purposes, or its toxicity. While its therapeutic uses may be due to the coincidental presence of other compounds, some uses of ATR-containing plants include treating sinusitis, headaches, syphilitic ulcers, and whitening teeth among other applications. Separately, the <i><a href="/wiki/Atractylis_gummifera" class="mw-redirect" title="Atractylis gummifera">Atractylis gummifera</a></i> is a traditional herb used in North Africa while <i><a href="/w/index.php?title=Callilepis_laureola&action=edit&redlink=1" class="new" title="Callilepis laureola (page does not exist)">Callilepis laureola</a></i> is well known to the <a href="/wiki/Zulu_people#Religion_and_beliefs" title="Zulu people">Zulu people</a> in South Africa for both therapeutical applications and its spiritual context to ward away evil spirits.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8">[8]</a></sup>
</p><p>When in high dosages, ATR's toxicity has been utilized for suicide and murder, though there have been no especially high-profile incidents reported, at least somewhat due to difficulties identifying ATR poisoning. More commonly than suicide or murder, ATR is a result of accidental poisoning: livestock grazing can poison animals,<sup id="cite_ref-Stewart2000_2-2" class="reference"><a href="#cite_note-Stewart2000-2">[2]</a></sup> while an unintended overdose or exposure of a plant containing ATR can poison humans. Particularly, the <i><a href="/wiki/Atractylis_gummifera" class="mw-redirect" title="Atractylis gummifera">Atractylis gummifera</a></i> is easily confused with wild artichoke and other vegetables, and its sweet-tasting roots facilitate its consumption.<sup id="cite_ref-Daniele2005_3-2" class="reference"><a href="#cite_note-Daniele2005-3">[3]</a></sup>
</p>
<h2><span class="mw-headline" id="Structure_and_reactivity">Structure and reactivity</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=3" title="Edit section: Structure and reactivity">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
<p>Atractyloside is a hydrophilic glycoside. A modified <a href="/wiki/Glucose" title="Glucose">glucose</a> is linked to the hydrophobic <a href="/wiki/Diterpene" title="Diterpene">diterpene</a> atractyligenin by a β1-<a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic bond</a>. A <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl group</a> is positioned at the C4 position in the axial position. The glucose part is esterified with <a href="/wiki/Isovaleric_acid" class="mw-redirect" title="Isovaleric acid">isovaleric acid</a> on the C2' atom, and <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> on the C3' and C4' atoms. By <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> a molecule of <small>D</small>-(+)-glucose, isovaleric acid, atractyligenin, and two molecules of sulfuric acid could be obtained. The two sulfate groups and the carboxyl group in ATR are in a <a href="/wiki/Deprotonated" class="mw-redirect" title="Deprotonated">deprotonated</a> form under physiological conditions. Thus, ATR is triple negatively charged.
</p>
<div class="thumb tright"><div class="thumbinner" style="width:222px;"><a href="/wiki/File:ATR-CATR_Numbered_Diagram.png" class="image"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/ATR-CATR_Numbered_Diagram.png/220px-ATR-CATR_Numbered_Diagram.png" decoding="async" width="220" height="166" class="thumbimage" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/ATR-CATR_Numbered_Diagram.png/330px-ATR-CATR_Numbered_Diagram.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/ATR-CATR_Numbered_Diagram.png/440px-ATR-CATR_Numbered_Diagram.png 2x" data-file-width="4127" data-file-height="3105" /></a> <div class="thumbcaption"><div class="magnify"><a href="/wiki/File:ATR-CATR_Numbered_Diagram.png" class="internal" title="Enlarge"></a></div>Numbered chemical structure of protonated ATR/CATR. The R group difference is depicted for ATR and CATR.</div></div></div>
<div class="thumb tright"><div class="thumbinner" style="width:222px;"><a href="/wiki/File:Atractyligenin_Numbered_Diagram.png" class="image"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Atractyligenin_Numbered_Diagram.png/220px-Atractyligenin_Numbered_Diagram.png" decoding="async" width="220" height="149" class="thumbimage" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Atractyligenin_Numbered_Diagram.png/330px-Atractyligenin_Numbered_Diagram.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Atractyligenin_Numbered_Diagram.png/440px-Atractyligenin_Numbered_Diagram.png 2x" data-file-width="2378" data-file-height="1611" /></a> <div class="thumbcaption"><div class="magnify"><a href="/wiki/File:Atractyligenin_Numbered_Diagram.png" class="internal" title="Enlarge"></a></div>Numbered atractyligenin chemical structure.</div></div></div>
<p>A modified variant of the atractylenolide carries an additional carboxyl group at the C4 atom of the atractyligenin, which is then referred to as <i>carboxy-atractyloside</i> (CATR), sometimes referred to as "gummiferin".<sup id="cite_ref-9" class="reference"><a href="#cite_note-9">[9]</a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10">[10]</a></sup> The ATR/CATR chemical structure on the right indicates this difference between compounds.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11">[11]</a></sup>
</p>
<h2><span class="mw-headline" id="Mechanism_of_action">Mechanism of action</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=4" title="Edit section: Mechanism of action">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
<p>In biochemical studies of <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>, the effect of atractyloside on the ADP/ATP transport was recognized even before the actual transporter was identified. ATR or CATR bind to the <a href="/wiki/ADP/ATP_translocase" class="mw-redirect" title="ADP/ATP translocase">ADP/ATP translocase</a>, which is located on the <a href="/wiki/Inner_mitochondrial_membrane" title="Inner mitochondrial membrane">inner mitochondrial membrane</a>. ATR binds competitively to the translocase <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive</a> up to a concentration of 5 <a href="/wiki/Mmol" class="mw-redirect" title="Mmol">mmol</a> while CATR binds in a <a href="/wiki/Non-competitive_inhibition" title="Non-competitive inhibition">non-competitive</a> manner. As a result, the exchange of <a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a> and <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> is no longer carried out and the cell dies due to lack of energy.
</p><p>The chemical structure and charge distribution of atractyloside is similar to that of ADP: the sulfate groups correspond to the phosphate groups, the glucose part corresponds to the ribose part, and the hydrophobic atractyligenine residue corresponds to the hydrophobic purine residue of ADP.
</p><p>The carboxyl group on the C4 atom of the atractyligenin is important for toxicity. If this is reduced to a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> (<i>atractylitriol</i>), the substance becomes non-toxic. Modification of any of the <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> groups renders the compound non-toxic.<sup id="cite_ref-Viggi_12-0" class="reference"><a href="#cite_note-Viggi-12">[12]</a></sup>
On the other hand, the free hydroxy group on the C6 atom of the <a href="/wiki/Glucose" title="Glucose">glucose</a> moiety can be modified without loss of compound potency.
</p>
<h2><span class="mw-headline" id="Poisoning">Poisoning</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=5" title="Edit section: Poisoning">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
<h3><span class="mw-headline" id="Symptoms">Symptoms</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=6" title="Edit section: Symptoms">edit</a><span class="mw-editsection-bracket">]</span></span></h3>
<p>Consumption of atractyloside (ATR) in plants will oftentimes also contain <a href="/wiki/Carboxyatractyloside" title="Carboxyatractyloside">carboxyatractyloside</a> (CATR), a highly toxic glycoside.<sup id="cite_ref-Daniele2005_3-3" class="reference"><a href="#cite_note-Daniele2005-3">[3]</a></sup>
</p><p>Ingestion of <i>A. gummifera</i>, <i>C. laureola</i>, <i>Xanthium</i>, or their extracts, may result in symptoms of <a href="/wiki/Abdominal_pain" title="Abdominal pain">gastrointenstinal pain</a>, nausea, diarrhea, and vomiting. Also possible is <a href="/wiki/Hypoventilation" title="Hypoventilation">respiratory depression</a> which may cause hypoxemia, leading to tissue hypoxia, spasms, stiffness, and convulsions.<sup id="cite_ref-Carlier2014_4-1" class="reference"><a href="#cite_note-Carlier2014-4">[4]</a></sup> In several cases, these symptoms are followed by <a href="/wiki/Coma" title="Coma">coma</a>. Postmortem analysis may indicate <a href="/wiki/Acute_liver_failure" title="Acute liver failure">hepatocellular damage</a> and <a href="/wiki/Kidney_failure" title="Kidney failure">renal failure</a>.<sup id="cite_ref-Daniele2005_3-4" class="reference"><a href="#cite_note-Daniele2005-3">[3]</a></sup>
</p><p>More recent literature has described sustained application of ATR on skin causing the symptoms described above, including <a href="/wiki/Hepatorenal_syndrome" title="Hepatorenal syndrome">hepatorenal injury</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13">[13]</a></sup>
</p>
<h3><span id="Identification_.2F_Quantification"></span><span class="mw-headline" id="Identification_/_Quantification">Identification / Quantification</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=7" title="Edit section: Identification / Quantification">edit</a><span class="mw-editsection-bracket">]</span></span></h3>
<p>The detection of herbal toxins has generally caused a diagnostic problem due to wide variety of plants and limited standard screening.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14">[14]</a></sup><sup id="cite_ref-Steenkamp2006_15-0" class="reference"><a href="#cite_note-Steenkamp2006-15">[15]</a></sup> For a long time, the identification of ATR poisoning was limited to postmortem analysis of one's kidneys or liver. Subsequent developments made to identify the presence of ATR in bodily fluids (blood or urine) only worked with high concentrations of ATR. Now, more recent research has established the necessary sensitivity and specificity to be applied to forensic toxicology.<sup id="cite_ref-Carlier2014_4-2" class="reference"><a href="#cite_note-Carlier2014-4">[4]</a></sup>
</p><p>The development of the below procedure relied on findings from unsuccessful methods of identification, primarily traced to the following literature in which the specificity and sensitivity was improved over time. Due to the limited research on the subject of ATR identification, this literature represents the primary sources to review:
</p>
<ul><li>1999: Established first quantifiable measurement of atractyloside in whole blood with <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">high-performance liquid chromatography</a>-<a href="/wiki/Tandem_mass_spectrometry" title="Tandem mass spectrometry">tandem mass spectrometry</a> (HPLC-MS-MS);<sup id="cite_ref-16" class="reference"><a href="#cite_note-16">[16]</a></sup></li>
<li>2001: GC-MS method required derivitization to detect atractyloside fragments;<sup id="cite_ref-17" class="reference"><a href="#cite_note-17">[17]</a></sup></li>
<li>2004: <a href="/wiki/Liquid_chromatography%E2%80%93mass_spectrometry" title="Liquid chromatography–mass spectrometry">LC-MS</a> (EI) using Waters Thermabeam detector resulted in complete fragmentation of the molecule; gentler ionization technique (<a href="/wiki/Electrospray_ionization" title="Electrospray ionization">ESI</a>) was successfully used to detect ATR after chromatographic separation;<sup id="cite_ref-Steenkamp2004_18-0" class="reference"><a href="#cite_note-Steenkamp2004-18">[18]</a></sup></li>
<li>2006: Further development of procedure with <a href="/wiki/Electrospray_ionization" title="Electrospray ionization">ESI</a>, eluent composition, and other experimental conditions, though still lacking specificity for forensic science.<sup id="cite_ref-Steenkamp2006_15-1" class="reference"><a href="#cite_note-Steenkamp2006-15">[15]</a></sup></li></ul>
<p>The procedure by <i>Carlier et al.</i> uses <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">high-performance liquid chromatography</a> coupled with high-resolution <a href="/wiki/Tandem_mass_spectrometry" title="Tandem mass spectrometry">tandem mass spectrometry</a> (HPLC-HRMS/MS). After the extraction of ATR and CATR from the blood or urine sample, separation was performed by reverse-phase HPLC. The MS detection used a quadrupole-orbitrap high-resolution detector after heated electrospray in negative ionization mode. These extraction techniques yielded 71.1% and 48.3% of ATR and CATR, respectively, in which these results met acceptable international criteria for forensic science: precision (≤15% or ≤20% at the <a href="/wiki/Calibration_curve" title="Calibration curve">LLOQ</a>) and accuracy (between 80 and 115% or 80-120% at the <a href="/wiki/Calibration_curve" title="Calibration curve">LLOQ</a>).<sup id="cite_ref-Carlier2014_4-3" class="reference"><a href="#cite_note-Carlier2014-4">[4]</a></sup>
</p><p>For reference, additional sources have fully characterized atractyloside in <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a>, MS, IR, etc.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19">[19]</a></sup>
</p>
<h3><span class="mw-headline" id="Lethality">Lethality</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=8" title="Edit section: Lethality">edit</a><span class="mw-editsection-bracket">]</span></span></h3>
<p>The mean <a href="/wiki/Lethal_dose" title="Lethal dose">lethal dose</a> in rats (<a href="/wiki/Intraperitoneal_injection" title="Intraperitoneal injection">i.p.</a>) for ATR is 143 mg/kg and for CATR is 2.9 mg/kg. This lethal dose of ATR takes approximately 150–180 minutes after injection until <a href="/wiki/Acute_tubular_necrosis" title="Acute tubular necrosis">acute tubular necrosis</a> occurred.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20">[20]</a></sup> This lethal dose varies across species and method of exposure. For example, the mean lethal dose of ATR in rats (<a href="/wiki/Subcutaneous_injection" title="Subcutaneous injection">s.c.</a>) is 155 mg/kg. Published mean lethal doses of ATR in other species includes 250 mg/kg (<a href="/wiki/Subcutaneous_injection" title="Subcutaneous injection">s.c.</a>) for rabbit, 200 mg/kg (<a href="/wiki/Intraperitoneal_injection" title="Intraperitoneal injection">i.p.</a>) for guinea pig, and 15 mg/kg (<a href="/wiki/Intravenous_therapy" title="Intravenous therapy">i.v.</a>) for dog.<sup id="cite_ref-Obatomi1998_1-2" class="reference"><a href="#cite_note-Obatomi1998-1">[1]</a></sup>
</p>
<h2><span class="mw-headline" id="See_also">See also</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=9" title="Edit section: See also">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
<ul><li><a href="/wiki/Carboxyatractyloside" title="Carboxyatractyloside">Carboxyatractyloside</a></li></ul>
<h2><span class="mw-headline" id="References">References</span><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Atractyloside&action=edit&section=10" title="Edit section: References">edit</a><span class="mw-editsection-bracket">]</span></span></h2>
<style data-mw-deduplicate="TemplateStyles:r1011085734">.mw-parser-output .reflist{font-size:90%;margin-bottom:0.5em;list-style-type:decimal}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist">
<div class="mw-references-wrap mw-references-columns"><ol class="references">
<li id="cite_note-Obatomi1998-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Obatomi1998_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Obatomi1998_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Obatomi1998_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r999302996">.mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .id-lock-free a,.mw-parser-output .citation .cs1-lock-free a{background:linear-gradient(transparent,transparent),url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited a,.mw-parser-output .id-lock-registration a,.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:linear-gradient(transparent,transparent),url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription a,.mw-parser-output .citation .cs1-lock-subscription a{background:linear-gradient(transparent,transparent),url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:linear-gradient(transparent,transparent),url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}</style><cite id="CITEREFObatomiBach1998" class="citation journal cs1">Obatomi, D.K; Bach, P.H (April 1998). "Biochemistry and Toxicology of the Diterpenoid Glycoside Atractyloside". <i>Food and Chemical Toxicology</i>. <b>36</b> (4): 335–346. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0278-6915%2898%2900002-7">10.1016/S0278-6915(98)00002-7</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/9651051">9651051</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+and+Chemical+Toxicology&rft.atitle=Biochemistry+and+Toxicology+of+the+Diterpenoid+Glycoside+Atractyloside&rft.volume=36&rft.issue=4&rft.pages=335-346&rft.date=1998-04&rft_id=info%3Adoi%2F10.1016%2FS0278-6915%2898%2900002-7&rft_id=info%3Apmid%2F9651051&rft.aulast=Obatomi&rft.aufirst=D.K&rft.au=Bach%2C+P.H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtractyloside" class="Z3988"></span></span>
</li>
<li id="cite_note-Stewart2000-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Stewart2000_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Stewart2000_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Stewart2000_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r999302996"/><cite id="CITEREFStewartSteenkamp2000" class="citation journal cs1">Stewart, Michael J.; Steenkamp, Vanessa (December 2000). "The Biochemistry and Toxicity of Atractyloside: A Review". <i>Therapeutic Drug Monitoring</i>. <b>22</b> (6): 641–649. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00007691-200012000-00001">10.1097/00007691-200012000-00001</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/11128230">11128230</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:5905401">5905401</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Therapeutic+Drug+Monitoring&rft.atitle=The+Biochemistry+and+Toxicity+of+Atractyloside%3A+A+Review&rft.volume=22&rft.issue=6&rft.pages=641-649&rft.date=2000-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5905401%23id-name%3DS2CID&rft_id=info%3Apmid%2F11128230&rft_id=info%3Adoi%2F10.1097%2F00007691-200012000-00001&rft.aulast=Stewart&rft.aufirst=Michael+J.&rft.au=Steenkamp%2C+Vanessa&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtractyloside" class="Z3988"></span></span>
</li>
<li id="cite_note-Daniele2005-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Daniele2005_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Daniele2005_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Daniele2005_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Daniele2005_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Daniele2005_3-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r999302996"/><cite id="CITEREFDanieleDahamnaFiruziSekfali2005" class="citation journal cs1">Daniele, C.; Dahamna, S.; Firuzi, O.; Sekfali, N.; Saso, L.; Mazzanti, G. (February 2005). "Atractylis gummifera L. poisoning: an ethnopharmacological review". <i>Journal of Ethnopharmacology</i>. <b>97</b> (2): 175–181. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jep.2004.11.025">10.1016/j.jep.2004.11.025</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/15707749">15707749</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Ethnopharmacology&rft.atitle=Atractylis+gummifera+L.+poisoning%3A+an+ethnopharmacological+review&rft.volume=97&rft.issue=2&rft.pages=175-181&rft.date=2005-02&rft_id=info%3Adoi%2F10.1016%2Fj.jep.2004.11.025&rft_id=info%3Apmid%2F15707749&rft.aulast=Daniele&rft.aufirst=C.&rft.au=Dahamna%2C+S.&rft.au=Firuzi%2C+O.&rft.au=Sekfali%2C+N.&rft.au=Saso%2C+L.&rft.au=Mazzanti%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtractyloside" class="Z3988"></span></span>
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<li id="cite_note-Carlier2014-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Carlier2014_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Carlier2014_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Carlier2014_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Carlier2014_4-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r999302996"/><cite id="CITEREFCarlierRomeufGuittonPriez-Barallon2014" class="citation journal cs1">Carlier, Jérémy; Romeuf, Ludovic; Guitton, Jérôme; Priez-Barallon, Cédric; Bévalot, Fabien; Fanton, Laurent; Gaillard, Yvan (December 2014). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjat%2Fbku078">"A Validated Method for Quantifying Atractyloside and Carboxyatractyloside in Blood by HPLC-HRMS/MS, a Non-Fatal Case of Intoxication with Atractylis gummifera L."</a> <i>Journal of Analytical Toxicology</i>. <b>38</b> (9): 619–627. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="cs1-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjat%2Fbku078">10.1093/jat/bku078</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/24990875">24990875</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Analytical+Toxicology&rft.atitle=A+Validated+Method+for+Quantifying+Atractyloside+and+Carboxyatractyloside+in+Blood+by+HPLC-HRMS%2FMS%2C+a+Non-Fatal+Case+of+Intoxication+with+Atractylis+gummifera+L.&rft.volume=38&rft.issue=9&rft.pages=619-627&rft.date=2014-12&rft_id=info%3Adoi%2F10.1093%2Fjat%2Fbku078&rft_id=info%3Apmid%2F24990875&rft.aulast=Carlier&rft.aufirst=J%C3%A9r%C3%A9my&rft.au=Romeuf%2C+Ludovic&rft.au=Guitton%2C+J%C3%A9r%C3%B4me&rft.au=Priez-Barallon%2C+C%C3%A9dric&rft.au=B%C3%A9valot%2C+Fabien&rft.au=Fanton%2C+Laurent&rft.au=Gaillard%2C+Yvan&rft_id=%2F%2Fdoi.org%2F10.1093%252Fjat%252Fbku078&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtractyloside" class="Z3988"></span></span>
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<li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r999302996"/><cite id="CITEREFChenHuChang2013" class="citation journal cs1">Chen, Liang-Yu; Hu, Anren; Chang, Chih-Jui (5 February 2013). <a rel="nofollow" class="external text" href="//www.ncbi.nlm.nih.gov/pmc/articles/PMC6270218">"The Degradation Mechanism of Toxic Atractyloside in Herbal Medicines by Decoction"</a>. <i>Molecules</i>. <b>18</b> (2): 2018–2028. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fmolecules18022018">10.3390/molecules18022018</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="cs1-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="//www.ncbi.nlm.nih.gov/pmc/articles/PMC6270218">6270218</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/23385339">23385339</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecules&rft.atitle=The+Degradation+Mechanism+of+Toxic+Atractyloside+in+Herbal+Medicines+by+Decoction&rft.volume=18&rft.issue=2&rft.pages=2018-2028&rft.date=2013-02-05&rft_id=%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6270218%23id-name%3DPMC&rft_id=info%3Apmid%2F23385339&rft_id=info%3Adoi%2F10.3390%2Fmolecules18022018&rft.aulast=Chen&rft.aufirst=Liang-Yu&rft.au=Hu%2C+Anren&rft.au=Chang%2C+Chih-Jui&rft_id=%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6270218&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtractyloside" class="Z3988"></span></span>
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<li id="cite_note-Steenkamp2004-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-Steenkamp2004_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r999302996"/><cite id="CITEREFSteenkampHardingHeerdenWyk2004" class="citation journal cs1">Steenkamp, Paul A.; Harding, Nial M.; Heerden, Fanie R. van; Wyk, Ben-Erik van (November 2004). "Determination of atractyloside in Callilepis laureola using solid-phase extraction and liquid chromatography–atmospheric pressure ionisation mass spectrometry". <i>Journal of Chromatography A</i>. <b>1058</b> (1–2): 153–162. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.chroma.2004.07.099">10.1016/j.chroma.2004.07.099</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chromatography+A&rft.atitle=Determination+of+atractyloside+in+Callilepis+laureola+using+solid-phase+extraction+and+liquid+chromatography%E2%80%93atmospheric+pressure+ionisation+mass+spectrometry&rft.volume=1058&rft.issue=1%E2%80%932&rft.pages=153-162&rft.date=2004-11&rft_id=info%3Adoi%2F10.1016%2Fj.chroma.2004.07.099&rft.aulast=Steenkamp&rft.aufirst=Paul+A.&rft.au=Harding%2C+Nial+M.&rft.au=Heerden%2C+Fanie+R.+van&rft.au=Wyk%2C+Ben-Erik+van&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtractyloside" class="Z3988"></span></span>
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<li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r999302996"/><cite id="CITEREFBrucoliBorrelloStapletonParkinson2012" class="citation journal cs1">Brucoli, Federico; Borrello, Maria T.; Stapleton, Paul; Parkinson, Gary N.; Gibbons, Simon (17 May 2012). "Structural Characterization and Antimicrobial Evaluation of Atractyloside, Atractyligenin, and 15-Didehydroatractyligenin Methyl Ester". <i>Journal of Natural Products</i>. <b>75</b> (6): 1070–1075. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fnp300080w">10.1021/np300080w</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="//pubmed.ncbi.nlm.nih.gov/22594797">22594797</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Natural+Products&rft.atitle=Structural+Characterization+and+Antimicrobial+Evaluation+of+Atractyloside%2C+Atractyligenin%2C+and+15-Didehydroatractyligenin+Methyl+Ester&rft.volume=75&rft.issue=6&rft.pages=1070-1075&rft.date=2012-05-17&rft_id=info%3Adoi%2F10.1021%2Fnp300080w&rft_id=info%3Apmid%2F22594797&rft.aulast=Brucoli&rft.aufirst=Federico&rft.au=Borrello%2C+Maria+T.&rft.au=Stapleton%2C+Paul&rft.au=Parkinson%2C+Gary+N.&rft.au=Gibbons%2C+Simon&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtractyloside" class="Z3988"></span></span>
</li>
<li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r999302996"/><cite id="CITEREFBhoola1983" class="citation book cs1">Bhoola, K.D.N. (1983). <i>A clino-pathological and biochemical study of the toxicity of Callilepis laureola (impila)</i>. Durban. pp. 128–131.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+clino-pathological+and+biochemical+study+of+the+toxicity+of+Callilepis+laureola+%28impila%29&rft.place=Durban&rft.pages=128-131&rft.date=1983&rft.aulast=Bhoola&rft.aufirst=K.D.N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAtractyloside" class="Z3988"></span></span>
</li>
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email-address Sign in Terms of use Privacy & cookies Passwort eingeben Ich habe mein Passwort vergessen Passwort eingeben Ich habe mein Passwort vergessen Passwort eingeben Ich habe mein Passwort vergessen Aktion abgeschlossen Sie werden weitergeleitet. Was ist das?