去乙酰基海杧果素

化合物

去乙酰基海杧果素(英語:deacetyltanghinin)是一种有细胞毒性强心苷,属于黄夹竹桃糖苷,化学式C30H44O9,可见于海杧果[1][2]海檬树英语Cerbera odollam[3]等物种。海杧果树叶、树皮和种子中均有分布[1],其中在种子内是最主要的甾体糖苷[4]。其可由海杧果素碳酸氢钾作用下,糖基中的乙酰基离去得到[5]。研究表明其对口腔人类表皮样癌细胞、人类乳腺癌细胞和人类小细胞肺癌细胞具有细胞毒性[1][6]

去乙酰基海杧果素
英文名 deacetyltanghinin
识别
CAS号 4589-95-1
PubChem 21637810
ChemSpider 10273192
SMILES
 
  • CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C46C(O6)CC3C2)O)C7=CC(=O)OC7)C)C)O)OC)O
InChI
 
  • 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
InChIKey LVGNJQMAMYJAIL-FWMNQDIBSA-N
ChEBI 66193
性质
化学式 C30H44O9
摩尔质量 548.66 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

参考资料

  1. ^ 1.0 1.1 1.2 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 (英语). 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 李荣芷,王云雯,陈毓群. 海芒果Cerbera odollam果仁中强心甙的分离鉴定. 药学学报. 1981, 16 (05): 361-365. 
  6. ^ Deacetyltanghinin. PubChem. 美国国立卫生研究院.