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O-去甲基加兰他敏

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O-去甲基加兰他敏
英文名 Sanguinine，O-desmethylgalantamine
识别
CAS号 60755-80-8
PubChem 443722
ChemSpider 391832
SMILES
 
  • CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)O)O
InChI
 
  • InChI=1S/C16H19NO3/c1-17-7-6-16-5-4-11(18)8-13(16)20-15-12(19)3-2-10(9-17)14(15)16/h2-5,11,13,18-19H,6-9H2,1H3/t11-,13-,16-/m0/s1
InChIKey OYSGWKOGUVOGFQ-RBOXIYTFSA-N
ChEBI 32117
性质
化学式 C16H19NO3
摩尔质量 273.33 g·mol−1
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

O-去甲基加兰他敏（Sanguinine）是一种有毒生物碱，化学式C16H19NO3，可见于血红石蒜[1][2]、香石蒜[3]、金花石蒜[4]等石蒜属[5]以及包括22种观赏水仙在内的水仙属[6]等物种。在结构上为加兰他敏上苯环上的甲氧基脱去甲基变成酚羟基得到。因结构中含有N-甲基结构，所以为乙酰胆碱酯酶强抑制剂（IC50=0.06 μM），且抑制作用远高于加兰他敏（IC50=0.35 μM）[6][5]。

参考资料

  1. ^ O Abdallah. Minor alkaloids from Lycoris sanguinea. Phytochemistry. 1995-05, 39 (2). doi:10.1016/0031-9422(94)00929-N. 
  2. ^ Shigeru Kobayashi; Kimihito Satoh; Atsushi Numata; Tetsuro Shingu; Masaru Kihara. Alkaloid N-oxides from Lycoris sanguinea. Phytochemistry. 1991-01, 30 (2). doi:10.1016/0031-9422(91)83751-6. 
  3. ^ Masaru KIHARA; Lai XU; Keiji KONISHI; Kiyoshi KIDA; Yoshimitsu NAGAO; Shigeru KOBAYASHI; Tetsuro SHINGU. Isolation and Structure Elucidation of a Novel Alkaloid, Incartine, a Supposed Biosynthetic Intermediate, from Flowers of Lycoris incarnata.. Chemical & Pharmaceutical Bulletin. 1994, 42 (2). doi:10.1248/CPB.42.289. 
  4. ^ Yu Yang; Yi-Min Zhao; Qin-Shi Zhao. Alkaloids from the Bulbs ofLycoris aurea. Helvetica Chimica Acta. 2005-09, 88 (9). doi:10.1002/HLCA.200590193. 
  5. ^ 5.0 5.1 Jean Paulo de Andrade, Raquel B. Giordani, Laura Torras-Claveria; et al. The Brazilian Amaryllidaceae as a source of acetylcholinesterase inhibitory alkaloids. Phytochemistry Reviews. 2016, 15: 147–160. doi:10.1007/s11101-015-9411-7. 
  6. ^ 6.0 6.1 Laura Torras-Claveria, Strahil Berkov, Carles Codina, Francesc Viladomat, Jaume Bastida. Daffodils as potential crops of galanthamine. Assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity. Industrial Crops and Products. 2013, 43: 237-244. doi:10.1016/j.indcrop.2012.07.034. 
检索自“https://zh.wikipedia.org/w/index.php?title=O-去甲基加兰他敏&oldid=84598306”