Carboxyatractyloside

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Carboxyatractyloside
Carboxyatractyloside.svg
Names
IUPAC name
15α-Hydroxy-2β-[2-O-(3-methylbutanoyl)-3,4-di-O-sulfo-β-D-glucopyranosyloxy]-5β,8α,9β,10α,13α-kaur-16-ene-18,19-dioic acid
Preferred IUPAC name
(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
Other names
CATR
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
EC Number
  • 251-444-9
UNII
  • InChI=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
    Key: AQFATIOBERWBDY-LNQSNDDKSA-N
  • 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
Properties
C31H46O18S2
Molar mass 770.81 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1] While atractyloside is effective in the inhibition of oxidative phosphorylation, carboxyatractyloside is considered to be more effective.[2] The effects of carboxyatractyloside on the ADP/ATP translocase are not reversed by increasing the concentration of adenine nucleotides, unlike its counterpart atractyloside.[2] Carboxyatractyloside behavior resembles bongkrekic acid while in the mitochondria.[2] Carboxyatractyloside is poisonous to humans as well as livestock, including cows[3] and horses.[4]

Symptoms of carboxyatractyloside poisoning may include abdominal pain, nausea and vomiting, drowsiness, palpitations, sweating and trouble breathing.[5] In severe cases, convulsions, liver failure and loss of consciousness may develop, which can lead to death.[5]

Carboxyatractyloside can be found in Xanthium species plants, including Xanthium strumarium.[6] Consumption of Xanthium containing the toxin led to the deaths of at least 19 people in Sylhet, Bangladesh during a period of food scarcity.[7] Along with atractyloside, it is also one of the main poisonous substances in the Atractylis gummifera thistle.[8]

References[edit]

  1. ^ Kedrov A, Hellawell AM, Klosin A, Broadhurst RB, Kunji ER, Müller DJ (January 2010). "Probing the interactions of carboxy-atractyloside and atractyloside with the yeast mitochondrial ADP/ATP carrier". Structure. 18 (1): 39–46. doi:10.1016/j.str.2009.11.009. PMID 20152151.
  2. ^ a b c Luciani S, Martini N, Santi R (September 1971). "Effects of carboxyatractyloside a structural analogue of atractyloside on mitochondrial oxidative phosphorylation". Life Sciences. 10 (17, Pt. 2): 961–8. doi:10.1016/0024-3205(71)90099-3. PMID 4255019.
  3. ^ Botha CJ, Lessing D, Rösemann M, van Wilpe E, Williams JH (September 2014). "Analytical confirmation of Xanthium strumarium poisoning in cattle". J Vet Diagn Invest. 26 (5): 640–645. doi:10.1177/1040638714542867. PMID 25012081.
  4. ^ Wilson, DA (2011). "Cocklebur Toxicosis". Clinical Veterinary Advisor - The Horse. University of Missouri, Columbia, Missouri: Elsevier. p. 115-116. ISBN 978-1-4160-9979-6.
  5. ^ a b Turgut M, Alhan CC, Gürgöze M, Kurt A, Doğan Y, Tekatli M, et al. (June 2005). "Carboxyatractyloside poisoning in humans". Annals of Tropical Medicine and Public Health. 25 (2): 125–134. doi:10.1179/146532805X45728. PMID 15949201. S2CID 25371968. Retrieved 1 January 2021.
  6. ^ Plumlee, Konnie (2004). "Chapter 25 - Plants". Clinical Veterinary Toxicology. Mosby. ISBN 978-0-323-01125-9.
  7. ^ Gurley ES, Rahman M, Hossain MJ, Nahar N, Faiz MA, Islam N, et al. (March 2010). "Fatal outbreak from consuming Xanthium strumarium seedlings during time of food scarcity in northeastern Bangladesh". PLOS ONE. 5 (3): e9756. Bibcode:2010PLoSO...5.9756G. doi:10.1371/journal.pone.0009756. PMC 2841199. PMID 20305785.
  8. ^ Daniele C, Dahamna S, Firuzi O, Sekfali N, Saso L, Mazzanti G (February 2005). "Atractylis gummifera L. poisoning: an ethnopharmacological review". Ethnopharmacol. 97 (3): 175–181. doi:10.1016/j.jep.2004.11.025. PMID 15707749.