Carboxyatractyloside

{{Chembox

| Name = Carboxyatractyloside

| ImageFile = Carboxyatractyloside.svg

| IUPACName = 15α-Hydroxy-2β-[2-O-(3-methylbutanoyl)-3,4-di-O-sulfono-β-D-glucopyranosyloxy]-5β,8α,9β,10α,13α-kaur-16-ene-18,19-dioic acid

| SystematicName = (2S,4aS,6aR,7S,9R,11aS,11bS)-7-Hydroxy-2-({(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-3-[(3-methylbutanoyl)oxy]oxan-2-yl}oxy)-11b-methyl-8-methylidenedodecahydro-6a,9-methanocyclohepta[a]naphthalene-4,4(1H)-dicarboxylic acid

| OtherNames = CATR

| Section1 = {{Chembox Identifiers

| ChemSpiderID = 16737649

| PubChem = 20055804

| CASNo = 33286-30-5

| DrugBank = DB02426

| EC_number = 251-444-9

| UNII = SNP1XL23E6

| StdInChI=1S/C31H46O18S2/c1-14(2)9-21(33)47-24-23(49-51(42,43)44)22(48-50(39,40)41)18(13-32)46-26(24)45-17-11-29(4)19-6-5-16-10-30(19,25(34)15(16)3)8-7-20(29)31(12-17,27(35)36)28(37)38/h14,16-20,22-26,32,34H,3,5-13H2,1-2,4H3,(H,35,36)(H,37,38)(H,39,40,41)(H,42,43,44)/t16-,17+,18-,19+,20+,22-,23+,24-,25+,26-,29+,30-/m1/s1

| StdInChIKey = AQFATIOBERWBDY-LNQSNDDKSA-N

| SMILES = CC(CC(=O)O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1OS(=O)(=O)O)OS(=O)(=O)O)CO)O[C@@H]2C[C@@]([C@@H]3[C@@](C2)([C@H]4[C@@]5([C@H](C(=C)[C@@H](C5)CC4)O)CC3)C)(C(=O)O)C(=O)O)C

}}

| Section2 = {{Chembox Properties

| C=31|H=46|O=18|S=2

}}

}}

Carboxyatractyloside (CATR) is a highly toxic diterpene glycoside that inhibits the ADP/ATP translocase. It is about 10 times more potent than its analog atractyloside.{{cite journal | vauthors = Kedrov A, Hellawell AM, Klosin A, Broadhurst RB, Kunji ER, Müller DJ | title = Probing the interactions of carboxy-atractyloside and atractyloside with the yeast mitochondrial ADP/ATP carrier | journal = Structure | volume = 18 | issue = 1 | pages = 39–46 | date = January 2010 | pmid = 20152151 | doi = 10.1016/j.str.2009.11.009 | doi-access = free }} While atractyloside is effective in the inhibition of oxidative phosphorylation, carboxyatractyloside is considered to be more effective.{{cite journal | vauthors = Luciani S, Martini N, Santi R | title = Effects of carboxyatractyloside a structural analogue of atractyloside on mitochondrial oxidative phosphorylation | journal = Life Sciences | volume = 10 | issue = 17 Pt 2 | pages = 961–968 | date = September 1971 | pmid = 4255019 | doi = 10.1016/0024-3205(71)90099-3 | url = https://pubmed.ncbi.nlm.nih.gov/4255019/}} The effects of carboxyatractyloside on the ADP/ATP translocase are not reversed by increasing the concentration of adenine nucleotides, unlike its counterpart atractyloside. Carboxyatractyloside behavior resembles bongkrekic acid while in the mitochondria. Carboxyatractyloside is poisonous to humans as well as livestock, including cows{{cite journal |vauthors=Botha CJ, Lessing D, Rösemann M, van Wilpe E, Williams JH |date=September 2014 |title=Analytical confirmation of Xanthium strumarium poisoning in cattle |journal=J Vet Diagn Invest |volume=26 |issue=5 |pages=640–645 |doi=10.1177/1040638714542867 |pmid=25012081 |doi-access=free |hdl=2263/42413 |hdl-access=free }} and horses.{{cite book |last=Wilson |first=DA |date=2011 |title=Clinical Veterinary Advisor – The Horse |url=https://www.sciencedirect.com/book/9781416099796/clinical-veterinary-advisor |location=University of Missouri, Columbia, Missouri |publisher=Elsevier |chapter=Cocklebur Toxicosis |pages=115–116 |isbn=978-1-4160-9979-6}}

Symptoms of carboxyatractyloside poisoning may include abdominal pain, nausea and vomiting, drowsiness, palpitations, sweating and trouble breathing.{{cite journal |vauthors=Turgut M, Alhan CC, Gürgöze M, Kurt A, Doğan Y, Tekatli M, Akpolat N, Aygün AD |date=June 2005 |title=Carboxyatractyloside poisoning in humans |url=https://pubmed.ncbi.nlm.nih.gov/15949201/ |journal= Annals of Tropical Medicine and Public Health |volume=25 |issue=2 |pages=125–134 |doi=10.1179/146532805X45728 |pmid=15949201 |s2cid = 25371968 |access-date=1 January 2021}} In severe cases, convulsions, liver failure and loss of consciousness may develop, which can lead to death.

Carboxyatractyloside can be found in Xanthium species plants, including Xanthium strumarium. {{cite book |last=Plumlee |first=Konnie |date=2004 |title=Clinical Veterinary Toxicology |chapter=Chapter 25: Plants |chapter-url=https://www.sciencedirect.com/science/article/pii/B032301125X500285 |publisher=Mosby |isbn=978-0-323-01125-9}} Consumption of Xanthium containing the toxin led to the deaths of at least 19 people in Sylhet, Bangladesh during a period of food scarcity. {{cite journal | vauthors = Gurley ES, Rahman M, Hossain MJ, Nahar N, Faiz MA, Islam N, Sultana R, Khatun S, Uddin MZ, Haider MS, Islam MS, Ahmed BN, Rahman MW, Mondal UK, Luby SP | title = Fatal outbreak from consuming Xanthium strumarium seedlings during time of food scarcity in northeastern Bangladesh | journal = PLOS ONE | volume = 5 | issue = 3 | pages = e9756 | date = March 2010 | pmid = 20305785 | pmc = 2841199 | doi = 10.1371/journal.pone.0009756 | bibcode = 2010PLoSO...5.9756G | doi-access = free }} Along with atractyloside, it is also one of the main poisonous substances in the Atractylis gummifera thistle.{{cite journal | vauthors = Daniele C, Dahamna S, Firuzi O, Sekfali N, Saso L, Mazzanti G | title = Atractylis gummifera L. poisoning: an ethnopharmacological review | journal = Ethnopharmacology | volume = 97 | issue = 3 | pages = 175–181 | date = February 2005 | pmid = 15707749 | doi = 10.1016/j.jep.2004.11.025 | url = https://pubmed.ncbi.nlm.nih.gov/15707749/}}