蝦夷扇貝毒素

蝦夷扇貝毒素
	IUPAC名; (2S,4aS,5aR,6R,6aS,7aR,8S,10aS,11aR,13aS,14aR,15aS,16aR,18S,19R,20aS,21aR,22aS,23aR,24aS,25aR,26aS,27aR,28aS,29aR)-6-Hydroxy-2-[(2R,3E)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-5a,8,10a,11a,19-pentamethyl-3-methylidene-19-[2-(sulfooxy)ethyl]octatriacontahydropyrano[2′′′,3′′′:5′′,6′′]pyrano[2′′,3′′:5′,6′]pyrano[2′,3′:5,6]pyrano[3,2-b]pyrano[2′′′′′,3′′′′′:5′′′′,6′′′′]pyrano[2′′′′,3′′′′:5′′′,6′′′]pyrano[2′′′,3′′′:5′′,6′′]pyrano[2′′,3′′:6′,7′]oxepino[2′,3′:5,6]pyrano[2,3-g]oxocin-18-yl hydrogen sulfate
識別
CAS號	112514-54-2
PubChem	6440821
ChemSpider	4945067
SMILES	O=S(=O)(O)O[C@H]4C[C@H]5O[C@H]6C[C@H]7O[C@H]8CC[C@]9(O[C@@]%10(C)CC[C@H](C)[C@H]%11O[C@@H]1[C@H](O[C@H]2C[C@H]3O[C@@H](C(=C)\C[C@@H]3O[C@]2(C)[C@@H]1O)[C@](O)(\C=C\C(=C)C\C=C)C)C[C@@H]%11O[C@@H]%10C[C@@H]9O[C@@H]8C[C@@H]7O[C@@H]6C[C@@H]5O[C@]4(C)CCOS(=O)(=O)O)C;
InChI	1/C55H82O21S2/c1-10-11-28(2)12-15-51(5,57)50-30(4)20-39-38(71-50)26-46-55(9,74-39)49(56)48-42(70-46)24-41-47(72-48)29(3)13-16-53(7)44(69-41)27-43-54(8,76-53)17-14-31-32(68-43)21-34-33(65-31)22-35-36(66-34)23-40-37(67-35)25-45(75-78(61,62)63)52(6,73-40)18-19-64-77(58,59)60/h10,12,15,29,31-50,56-57H,1-2,4,11,13-14,16-27H2,3,5-9H3,(H,58,59,60)(H,61,62,63)/b15-12+/t29-,31-,32+,33+,34-,35-,36+,37+,38+,39-,40-,41-,42+,43-,44+,45-,46-,47+,48+,49+,50-,51+,52+,53-,54+,55-/m0/s1;
InChIKey	HCYDZFJGUKMTQB-AVHIVUAZBJ
性質
化學式	C55H82O21S2
摩爾質量	1143.36 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

蝦夷扇貝毒素（英語：Yessotoxin，YTX）一種聚醚類赤潮藻類毒素，在結構上與雪卡毒素相似^[1]。由赤潮元兇之一的甲藻產生，特別是多邊舌甲藻（英語：Lingulodinium polyedrum）（Lingulodinium polyedrum）和具刺膝溝藻（英語：Gonyaulax spinifera）（Gonyaulax spinifera）兩種著名的甲藻^[2]。

當這些產蝦夷扇貝毒素的甲藻大量繁殖時，毒素會在雙殼綱扇貝（包括貽貝、扇貝和蛤蜊）可食用部分進行生物積累，從而進入食物鏈，對人類健康造成威脅^[3]。

歷史

蝦夷扇貝毒素在20世紀60年代在蝦夷盤扇貝（Patinopecten yessoensis）中發現^[4]，後面又在海藻和其他貝類中發現了許多類蝦夷扇貝毒素，包括45-羥基蝦夷扇貝毒素和羧基蝦夷扇貝毒素等^[1]。

科學家最初將蝦夷扇貝毒素錯誤地將其歸類為與氮雜螺環酸（英語：Azaspiracid）（原多甲藻酸）、岡田酸（軟海綿酸）類似的腹瀉性貝毒素（DSP）中。這類毒素可導致極度胃腸不適並促進癌症生長。當科學家意識到蝦夷扇貝毒素不具有與其他毒素相同的毒理學作用機制（蛋白磷酸酶抑制劑）時，蝦夷扇貝毒素因此被劃分到新的分類中^[5]。

毒性

已開展了大量研究來評估蝦夷扇貝毒素的潛在毒性，但迄今為止這些研究均未強調蝦夷扇貝毒素對人體產生的任何毒性作用。然而，研究發現當蝦夷扇貝毒素通過腹膜內注射給小鼠時，會對小鼠產生毒性作用。所遇到的毒性作用與麻痹性貝類毒素相似，包括肝毒性、心臟毒性和神經毒性。當蝦夷扇貝毒素水平達到 100 μg/kg 時就會引起毒性作用。動物口服毒素後，僅觀察到有限的毒性作用。蝦夷扇貝毒素髮揮毒性作用的機制尚不清楚，目前正在對此進行研究。一些研究表明其毒性機制與體內鈣離子平衡改變有關^[6]。蝦夷扇貝毒素還被證實具有遺傳毒性^[7]^[8]。

雖然沒有直接數據表明蝦夷扇貝毒素對人體毒性有關，由於注意到顯著的動物毒性，蝦夷扇貝毒素潛在健康風險的問題仍然存在。蝦夷扇貝毒素與貝類中存在的其他藻類毒素一樣不會被加熱或冷凍破壞^[3]。因此，包括紐西蘭、日本和歐洲在內的多個國家都對貝類中的蝦夷扇貝毒素含量進行了監管。2002 年，歐盟規定每克供人類食用的貝類肉中含量不超過 1 μg YTX（1 mg/kg）^[2]。

蝦夷扇貝毒素同時會引發核糖體毒性應激^[9]。

參考文獻

^ ^1.0 ^1.1 A. Tubaro; V. Dell'Ovo; S. Sosa; C. Florio. Yessotoxins: A Toxicological Overview. Toxicon. 2010, 56 (2): 163–172. PMID 19660487. doi:10.1016/j.toxicon.2009.07.038.
^ ^2.0 ^2.1 M. D. A. Howard; M. Silver; R. M. Kudela. Yessotoxin detected in mussel (Mytilus californicus) and phytoplankton samples from the U.S. west coast. Harmful Algae. 2008, 7 (5): 646–652. doi:10.1016/j.hal.2008.01.003.
^ ^3.0 ^3.1 Marine biotoxins in shellfish – Summary on regulated marine biotoxins (pdf). Scientific opinion of the Panel on Contaminants in the Food Chain. European Food Safety Authority. 13 August 2009 [2024-07-12]. Question No EFSA-Q-2009-00685. （原始內容存檔於2024-07-12）.
^ M. Murata; M. Kumagi; J. S. Lee; T. Yasumoto. Isolation and Structure of Yessotoxin, a Novel Polyether Compound Implicated in Diarrhetic Shellfish Poisoning. Tetrahedron Letters. 1987, 28 (47): 5869–5872. doi:10.1016/S0040-4039(01)81076-5.
^ P. de la Iglesia; A. Gago-Martinez; T. Yasumoto. Advanced studies for the application of high-performance capillary electrophoresis for the analysis of yessotoxin and 45-hydroxyyessotoxin. Journal of Chromatography A. 2007, 1156 (1–2): 160–166. PMID 17239891. doi:10.1016/j.chroma.2006.12.084.
^ B. Paz; A. H. Daranas; M. Norte; P. Riobo; J. M. Franco; J. J. Fernandez. Yessotoxins, a group of marine polyether toxins; an overview. Marine Drugs. 2008, 6 (2): 73–102. PMC 2525482 . PMID 18728761. doi:10.3390/md6020073 .
^ Korsnes, Mónica S.; Korsnes, Reinert. Mitotic Catastrophe in BC3H1 Cells following Yessotoxin Exposure. Frontiers in Cell and Developmental Biology. 2017, 5: 30. PMC 5374163 . PMID 28409150. doi:10.3389/fcell.2017.00030 .
^ Korsnes, Mónica S.; Korsnes, Reinert. Single-Cell Tracking of A549 Lung Cancer Cells Exposed to a Marine Toxin Reveals Correlations in Pedigree Tree Profiles. Frontiers in Oncology. 2018, 8: 260. PMC 6039982 . PMID 30023341. doi:10.3389/fonc.2018.00260 .
^ Suárez Korsnes, Mónica; Skogtvedt Røed, Susan; Tranulis, Michael A.; Espenes, Arild; Christophersen, Berit. Yessotoxin triggers ribotoxic stress. Toxicology in Vitro. 2014, 28 (5): 975–981. PMID 24780217. doi:10.1016/j.tiv.2014.04.013 . hdl:11250/2574125 .

參考書目

J. Aasen; I. A. Samdal; C. O. Miles; E. Dahl; L. R. Briggs; T. Aune. Yessotoxins in Norwegian blue mussels (Mytilus edulis): Uptake from Protoceratium reticulatum, metabolism and depuration. Toxicon. 2005, 45 (3): 265–272. PMID 15683864. doi:10.1016/j.toxicon.2004.10.012.

[tubaro-1] 1.0 ^1.1 A. Tubaro; V. Dell'Ovo; S. Sosa; C. Florio. Yessotoxins: A Toxicological Overview. Toxicon. 2010, 56 (2): 163–172. PMID 19660487. doi:10.1016/j.toxicon.2009.07.038.

[howard-2] 2.0 ^2.1 M. D. A. Howard; M. Silver; R. M. Kudela. Yessotoxin detected in mussel (Mytilus californicus) and phytoplankton samples from the U.S. west coast. Harmful Algae. 2008, 7 (5): 646–652. doi:10.1016/j.hal.2008.01.003.

[efsa-3] 3.0 ^3.1 Marine biotoxins in shellfish – Summary on regulated marine biotoxins (pdf). Scientific opinion of the Panel on Contaminants in the Food Chain. European Food Safety Authority. 13 August 2009 [2024-07-12]. Question No EFSA-Q-2009-00685. （原始內容存檔於2024-07-12）.

[4] M. Murata; M. Kumagi; J. S. Lee; T. Yasumoto. Isolation and Structure of Yessotoxin, a Novel Polyether Compound Implicated in Diarrhetic Shellfish Poisoning. Tetrahedron Letters. 1987, 28 (47): 5869–5872. doi:10.1016/S0040-4039(01)81076-5.

[iglesia-5] P. de la Iglesia; A. Gago-Martinez; T. Yasumoto. Advanced studies for the application of high-performance capillary electrophoresis for the analysis of yessotoxin and 45-hydroxyyessotoxin. Journal of Chromatography A. 2007, 1156 (1–2): 160–166. PMID 17239891. doi:10.1016/j.chroma.2006.12.084.

[paz-6] B. Paz; A. H. Daranas; M. Norte; P. Riobo; J. M. Franco; J. J. Fernandez. Yessotoxins, a group of marine polyether toxins; an overview. Marine Drugs. 2008, 6 (2): 73–102. PMC 2525482 . PMID 18728761. doi:10.3390/md6020073 .

[Korsnes_and_Korsnes,_2017-7] Korsnes, Mónica S.; Korsnes, Reinert. Mitotic Catastrophe in BC3H1 Cells following Yessotoxin Exposure. Frontiers in Cell and Developmental Biology. 2017, 5: 30. PMC 5374163 . PMID 28409150. doi:10.3389/fcell.2017.00030 .

[Korsnes_and_Korsnes,_2018-8] Korsnes, Mónica S.; Korsnes, Reinert. Single-Cell Tracking of A549 Lung Cancer Cells Exposed to a Marine Toxin Reveals Correlations in Pedigree Tree Profiles. Frontiers in Oncology. 2018, 8: 260. PMC 6039982 . PMID 30023341. doi:10.3389/fonc.2018.00260 .

[9] Suárez Korsnes, Mónica; Skogtvedt Røed, Susan; Tranulis, Michael A.; Espenes, Arild; Christophersen, Berit. Yessotoxin triggers ribotoxic stress. Toxicology in Vitro. 2014, 28 (5): 975–981. PMID 24780217. doi:10.1016/j.tiv.2014.04.013 . hdl:11250/2574125 .

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