膠蒼朮苷

膠蒼朮苷
	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
	系統名; (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
別名	CATR，羧基蒼朮苷
識別
CAS號	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
性質
化學式	C31H46O18S2
摩爾質量	770.82 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

膠蒼朮苷（英語：Carboxyatractyloside，CATR）是一種二萜糖苷，屬於ADP/ATP轉位酶（英語：Adenine nucleotide translocator）抑制劑。其抑制能力是其同系物蒼朮苷的十倍^[1]。且其氧化磷酸化抑制能力被認為比蒼朮苷更有效^[2]。與蒼朮苷不同，膠蒼朮苷對ADP/ATP轉位酶的作用不會因腺嘌呤核苷酸的濃度增加而逆轉^[2]。在線粒體中，其毒性行為和米酵菌酸類似^[2]。膠蒼朮苷對人類和包括牛和馬在內的牲畜都有毒性^[3]^[4]。

膠蒼朮苷中毒症狀可能包括腹痛、噁心嘔吐、嗜睡、心悸、出汗和呼吸困難。在嚴重的情況下，可能會出現抽搐、肝功能衰竭和意識喪失，並可能導致死亡^[5]。

膠蒼朮苷存在於蒼耳屬植物中，如蒼耳等^[6]。孟加拉國錫爾赫特專區在饑荒期間曾有食用含有膠蒼朮苷的蒼耳屬植物導致的至少19人死亡事例^[7]。

膠蒼朮苷與蒼朮苷一起作為膠脂蒼朮（英語：Chamaeleon gummifer）（Chamaeleon gummifer）主要的毒性物質^[8]。

參考文獻

^ 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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參考文獻