O-去甲基加蘭他敏

O-去甲基加蘭他敏
英文名	Sanguinine，O-desmethylgalantamine
識別
CAS號	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
性質
化學式	C16H19NO3
摩爾質量	273.33 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

O-去甲基加蘭他敏（Sanguinine）是一種有毒生物鹼，化學式C₁₆H₁₉NO₃，可見於血紅石蒜^[1]^[2]、香石蒜^[3]、金花石蒜^[4]等石蒜屬^[5]以及包括22種觀賞水仙在內的水仙屬^[6]等物種。在結構上為加蘭他敏上苯環上的甲氧基脫去甲基變成酚羥基得到。因結構中含有N-甲基結構，所以為乙醯膽鹼酯酶強抑制劑（IC₅₀=0.06 μM），且抑制作用遠高於加蘭他敏（IC₅₀=0.35 μM）^[6]^[5]。

參考資料

^ O Abdallah. Minor alkaloids from Lycoris sanguinea. Phytochemistry. 1995-05, 39 (2). doi:10.1016/0031-9422(94)00929-N.
^ 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.
^ 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.
^ 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.
^ ^5.0 ^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.
^ ^6.0 ^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.

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