胶苍术苷

胶苍术苷
	IUPAC名; 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
	系统名; (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
别名	CATR，羧基苍术苷
识别
CAS号	33286-30-5
PubChem	20055804
ChemSpider	16737649
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;
DrugBank	DB02426
性质
化学式	C31H46O18S2
摩尔质量	770.82 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

胶苍术苷（英語：Carboxyatractyloside，CATR）是一种二萜糖苷，属于ADP/ATP转位酶（英语：Adenine nucleotide translocator）抑制剂。其抑制能力是其同系物苍术苷的十倍^[1]。且其氧化磷酸化抑制能力被认为比苍术苷更有效^[2]。与苍术苷不同，胶苍术苷对ADP/ATP转位酶的作用不会因腺嘌呤核苷酸的浓度增加而逆转^[2]。在线粒体中，其毒性行为和米酵菌酸类似^[2]。胶苍术苷对人类和包括牛和马在内的牲畜都有毒性^[3]^[4]。

胶苍术苷中毒症状可能包括腹痛、恶心呕吐、嗜睡、心悸、出汗和呼吸困难。在严重的情况下，可能会出现抽搐、肝功能衰竭和意识丧失，并可能导致死亡^[5]。

胶苍术苷存在于苍耳属植物中，如苍耳等^[6]。孟加拉国锡尔赫特专区在饥荒期间曾有食用含有胶苍术苷的苍耳属植物导致的至少19人死亡事例^[7]。

胶苍术苷与苍术苷一起作为胶脂苍术（英语：Chamaeleon gummifer）（Chamaeleon gummifer）主要的毒性物质^[8]。

参考文献

^ Kedrov A, Hellawell AM, Klosin A, Broadhurst RB, Kunji ER, Müller DJ. Probing the interactions of carboxy-atractyloside and atractyloside with the yeast mitochondrial ADP/ATP carrier. Structure. January 2010, 18 (1): 39–46. PMID 20152151. doi:10.1016/j.str.2009.11.009 .
^ ^2.0 ^2.1 ^2.2 Luciani S, Martini N, Santi R. Effects of carboxyatractyloside a structural analogue of atractyloside on mitochondrial oxidative phosphorylation. Life Sciences. September 1971, 10 (17, Pt. 2): 961–8. PMID 4255019. doi:10.1016/0024-3205(71)90099-3.
^ Botha CJ, Lessing D, Rösemann M, van Wilpe E, Williams JH. Analytical confirmation of Xanthium strumarium poisoning in cattle. J Vet Diagn Invest. September 2014, 26 (5): 640–645. PMID 25012081. doi:10.1177/1040638714542867 . hdl:2263/42413 .
^ Wilson, DA. Cocklebur Toxicosis. Clinical Veterinary Advisor - The Horse. University of Missouri, Columbia, Missouri: Elsevier. 2011: 115-116. ISBN 978-1-4160-9979-6.
^ Turgut M, Alhan CC, Gürgöze M, Kurt A, Doğan Y, Tekatli M, et al. Carboxyatractyloside poisoning in humans. Annals of Tropical Medicine and Public Health. June 2005, 25 (2): 125–134 [1 January 2021]. PMID 15949201. S2CID 25371968. doi:10.1179/146532805X45728.
^ Plumlee, Konnie. Chapter 25 - Plants. Clinical Veterinary Toxicology. Mosby. 2004. ISBN 978-0-323-01125-9.
^ Gurley ES, Rahman M, Hossain MJ, Nahar N, Faiz MA, Islam N, et al. Fatal outbreak from consuming Xanthium strumarium seedlings during time of food scarcity in northeastern Bangladesh. PLOS ONE. March 2010, 5 (3): e9756. Bibcode:2010PLoSO...5.9756G. PMC 2841199 . PMID 20305785. doi:10.1371/journal.pone.0009756 .
^ Daniele C, Dahamna S, Firuzi O, Sekfali N, Saso L, Mazzanti G. Atractylis gummifera L. poisoning: an ethnopharmacological review. Ethnopharmacol. February 2005, 97 (3): 175–181. PMID 15707749. doi:10.1016/j.jep.2004.11.025.

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[1] Kedrov A, Hellawell AM, Klosin A, Broadhurst RB, Kunji ER, Müller DJ. Probing the interactions of carboxy-atractyloside and atractyloside with the yeast mitochondrial ADP/ATP carrier. Structure. January 2010, 18 (1): 39–46. PMID 20152151. doi:10.1016/j.str.2009.11.009 .

[Luciani71-2] 2.0 ^2.1 ^2.2 Luciani S, Martini N, Santi R. Effects of carboxyatractyloside a structural analogue of atractyloside on mitochondrial oxidative phosphorylation. Life Sciences. September 1971, 10 (17, Pt. 2): 961–8. PMID 4255019. doi:10.1016/0024-3205(71)90099-3.

[Botha14-3] Botha CJ, Lessing D, Rösemann M, van Wilpe E, Williams JH. Analytical confirmation of Xanthium strumarium poisoning in cattle. J Vet Diagn Invest. September 2014, 26 (5): 640–645. PMID 25012081. doi:10.1177/1040638714542867 . hdl:2263/42413 .

[Wilson11-4] Wilson, DA. Cocklebur Toxicosis. Clinical Veterinary Advisor - The Horse. University of Missouri, Columbia, Missouri: Elsevier. 2011: 115-116. ISBN 978-1-4160-9979-6.

[Turgut05-5] Turgut M, Alhan CC, Gürgöze M, Kurt A, Doğan Y, Tekatli M, et al. Carboxyatractyloside poisoning in humans. Annals of Tropical Medicine and Public Health. June 2005, 25 (2): 125–134 [1 January 2021]. PMID 15949201. S2CID 25371968. doi:10.1179/146532805X45728.

[xanthium-6] Plumlee, Konnie. Chapter 25 - Plants. Clinical Veterinary Toxicology. Mosby. 2004. ISBN 978-0-323-01125-9.

[xanthium_poisoning-7] Gurley ES, Rahman M, Hossain MJ, Nahar N, Faiz MA, Islam N, et al. Fatal outbreak from consuming Xanthium strumarium seedlings during time of food scarcity in northeastern Bangladesh. PLOS ONE. March 2010, 5 (3): e9756. Bibcode:2010PLoSO...5.9756G. PMC 2841199 . PMID 20305785. doi:10.1371/journal.pone.0009756 .

[Daniele05-8] Daniele C, Dahamna S, Firuzi O, Sekfali N, Saso L, Mazzanti G. Atractylis gummifera L. poisoning: an ethnopharmacological review. Ethnopharmacol. February 2005, 97 (3): 175–181. PMID 15707749. doi:10.1016/j.jep.2004.11.025.

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