扁桃苷

扁桃苷
IUPAC名
[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy](phenyl)acetonitrile
别名 苦杏仁苷
“维生素B17”
识别
CAS号 29883-15-6  checkY
858290-27-4（三水合物）  checkY
PubChem 34751
ChemSpider 4588479
SMILES
 
  • O[C@@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]3OC[C@H]2O[C@@H](OC(C#N)c1ccccc1)[C@H](O)[C@@H](O)[C@@H]2O
MeSH Amygdalin
性质
化学式 C20H27NO11
摩尔质量 457.43 g·mol−1
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。
维基百科中的醫學内容仅供参考，並不能視作專業意見。如需獲取醫療幫助或意見，请咨询专业人士。詳見醫學聲明。

扁桃苷（Amygdalin，源自希腊语“扁桃”ἀμυγδάλη amygdálē ），又名「苦杏仁苷」 ，是可從許多植物中發現的一種有毒的氰苷，但最常見於杏、苦杏仁、蘋果、桃及梅子等植物的種子中，易形成水合物。是1803年皮埃尔-让-洛比克（英语：Pierre Jean Robiquet）[1]与A. F. Boutron-Charlard从扁桃的种子中分离出的一种糖苷。李比希与维勒于1830年研究了这一物质。扁桃苷也存在于其他的李属植物，包括杏和黑樱桃中[2]，也存在於枇杷的葉、果和核裡。恩斯特·T·克雷布斯（Ernst T. Krebs）曾将这一物质命名为“维生素B17”，并认为可以治疗癌症，但随后的研究证明这一物质并不具有上述功效。[3][4][5]學界也不認為苦杏仁苷是一種維生素，因為苦杏仁苷並不符合維生素的定義。[6]

化学性质

扁桃苷的提取，可用扁桃或杏仁在乙醇中加热，之后蒸发溶剂并添加乙醚，即可得到细小的白色扁桃苷晶体。李比希和沃勒发现扁桃苷分解时生成三种产物：糖类、苯甲醛和氢氰酸[7]。之后的研究表明，硫酸催化下扁桃苷分解成葡萄糖，苯甲醛和氢氰酸，而盐酸使之分解为扁桃酸，D-葡萄糖和氨。[8]

在酶的催化下扁桃苷有两种分解：麦芽糖酶使之部分分解，生成D-葡萄糖与野黑樱苷（C6H5CH(CN)O·C6H11O5），一种苯乙腈葡糖苷的同分异构体。扁桃酶则可使之分解为苯甲醛、氰化物和两分子葡萄糖。这一反應出现在苦扁桃中，导致苦扁桃中通常含有自由的苯甲醛与氰化物。

参考资料

  1. ^ A chronology of significant historical developments in the biological sciences. Botany Online Internet Hypertextbook. University of Hamburg, Department of Biology. 2002-08-18 [2007-08-06]. （原始内容存档于2007-08-20）. 
  2. ^ Swain E, Poulton JE. Utilization of Amygdalin during Seedling Development of Prunus serotina. Plant physiology. October 1994, 106 (2): 437–445. PMC 159548 可免费查阅. PMID 12232341. doi:10.1104/pp.106.2.437. 
  3. ^ Ellison NM, Byar DP, Newell GR. Special report on Laetrile: the NCI Laetrile Review. Results of the National Cancer Institute's retrospective Laetrile analysis. N. Engl. J. Med. September 1978, 299 (10): 549–52. PMID 683212. 
  4. ^ Moertel CG, Ames MM, Kovach JS, Moyer TP, Rubin JR, Tinker JH. A pharmacologic and toxicological study of amygdalin. JAMA. February 1981, 245 (6): 591–4. PMID 7005480. doi:10.1001/jama.245.6.591. 
  5. ^ Moertel CG, Fleming TR, Rubin J; et al. A clinical trial of amygdalin (Laetrile) in the treatment of human cancer. N. Engl. J. Med. January 1982, 306 (4): 201–6 [2009-08-13]. PMID 7033783. doi:10.1007/s00520-006-0168-9. （原始内容存档于2003-04-21）. 
  6. ^ Lerner IJ. Laetrile: a lesson in cancer quackery. CA Cancer J Clin. 1981, 31 (2): 91–5. PMID 6781723. doi:10.3322/canjclin.31.2.91. 
  7. ^ F. Wöhler, J. Liebig. Ueber die Bildung des Bittermandelöls. Annalen der Pharmacie. 1837, 22 (1): 1–24. doi:10.1002/jlac.18370220102. 
  8. ^ J. W. Walker, V. K. Krieble. The hydrolysis of amygdalin by acids. Part I. Journal of the Chemical Society. 1909, 95 (11): 1369–77. doi:10.1039/CT9099501369. 

外部連結

維基學院中的相關研究或學習資源：维生素B17与癌症治疗

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