去乙酰基海杧果素(英語:deacetyltanghinin)是一種有細胞毒性的強心苷,屬於黃夾竹桃糖苷,化學式C30H44O9,可見於海杧果[1][2]、海檬樹[3]等物種。海杧果樹葉、樹皮和種子中均有分佈[1],其中在種子內是最主要的甾體糖苷[4]。其可由海杧果素在碳酸氫鉀作用下,糖基中的乙酰基離去得到[5]。研究表明其對口腔人類表皮樣癌細胞、人類乳腺癌細胞和人類小細胞肺癌細胞具有細胞毒性[1][6]。
Quick Facts 去乙酰基海杧果素, 識別 ...
去乙酰基海杧果素
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英文名
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deacetyltanghinin
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識別
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CAS號
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4589-95-1
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PubChem
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21637810
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ChemSpider
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10273192
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SMILES
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- CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C46C(O6)CC3C2)O)C7=CC(=O)OC7)C)C)O)OC)O
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InChI
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- InChI=1S/C30H44O9/c1-15-23(32)25(35-4)24(33)26(37-15)38-18-5-8-27(2)17(12-18)13-21-30(39-21)20(27)7-9-28(3)19(6-10-29(28,30)34)16-11-22(31)36-14-16/h11,15,17-21,23-26,32-34H,5-10,12-14H2,1-4H3/t15-,17-,18-,19+,20+,21-,23-,24-,25+,26-,27-,28+,29+,30+/m0/s1
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InChIKey
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LVGNJQMAMYJAIL-FWMNQDIBSA-N
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ChEBI
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66193
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性質
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化學式
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C30H44O9
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摩爾質量
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548.66 g·mol−1
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若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。
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Sarot Cheenpracha; Chatchanok Karalai; Yanisa Rat-A-Pa; Chanita Ponglimanont; Kan Chantrapromma. New cytotoxic cardenolide glycoside from the seeds of Cerbera manghas. Chemical & Pharmaceutical Bulletin. 2004, 52 (8). doi:10.1248/CPB.52.1023 (英語).
FUMIKO ABE; TATSUO YAMAUCHI. Studies on Cerbera. I. Cardiac glycosides in the seeds, bark, and leaves of Cerbera manghas L.. Chemical & Pharmaceutical Bulletin. 1977, 25 (10). doi:10.1248/CPB.25.2744.
TATSUO YAMAUCHI; FUMIKO ABE; ALFRED S.C. WAN. Cerbera. III. Cardenolide monoglycosides from the leaves of Cerbera odollam and Cerbera manghas.. Chemical & Pharmaceutical Bulletin. 1987, 35 (7). doi:10.1248/CPB.35.2744.
Jérémy Carlier, Jérôme Guitton, Fabien Bévalot, Laurent Fanton, Yvan Gaillard. The principal toxic glycosidic steroids in Cerbera manghas L. seeds: Identification of cerberin, neriifolin, tanghinin and deacetyltanghinin by UHPLC–HRMS/MS, quantification by UHPLC–PDA-MS. Journal of Chromatography B. 2014, 962: 1-8. doi:10.1016/j.jchromb.2014.05.014.