Uses
The lotus leaf alkaloid has the effect of weight loss and lipid reduction, and can be used for content determination/identification/pharmacological experiments.
Description
Nuciferine is an aporphine alkaloid from Nelumbo lutea, the ba~e yields colourless crystals
when crystallized from EtOH. It is laevorotatory, the following specific rotations
having been recorded; [α]
22D- 157.5° and - 215°. The ultraviolet spectrum has
three absorption maxima at 230, 272 and 310 mp. Two methoxyl groups and
one methylimino group are present and the alkaloid may be characterized as the
hydrochloride, m.p. 241°C (in vacuo) and the methiodide, m.p. 177-8°C. The
optically inactive base has been synthesized and has m.p. 136-7°C, giving a
hydrochloride in the form of small colourless prisms from H20, m.p. 258°C
(dec.).
Chemical Properties
Soluble in benzene, ether, chloroform, halogenated alkanes and other organic solvents of low polarity, in acetone, ethanol and other hydrophilic organic solvents also have good solubility, but less soluble or almost insoluble in water Derived from the dried leaves of Lotus japonicus, family Water Lily
Uses
Nuciferin is an drug candidate for the treatment of obesity-related diseases. It is not well studied and its pharmacokinetics in vivo have not been fully investigated.
Safety Profile
Poison by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic fumes of NOx.
Synthesis
Nuciferine can be synthesized from readily available (2-nitroethenyl)benzene derivatives through sequential Pictet–Spengler and radical cyclization, or in a six-step longest linear sequence from commercially available benzaldehyde in 21% overall yield, with Bu3SnH-mediated radical cyclization of an aryl bromide and Pictet–Spengler reaction of an N-substituted amine with an aldehyde as the key transformations[1].
References
Gulland, Haworth., J. Chern. Soc., 590 (1928)
Yunusov, Konovalova, Orekhov., Bull. Soc. Chim. Fr., 70 (1940)
Arthur, Cheung., J. Chern. Soc., 2306 (1959)
Kupchan et al., Tetrahedron, 19, 227 (1963)
[1]
Chang, C.-F., Huang, C.-Y., Huang, Y.-C., Lin, K.-Y., Lee, Y.-J., Wang, C.-J. (2010). Total Synthesis of (±)-Armepavines and (±)-Nuciferines From (2-Nitroethenyl)benzene Derivatives. Synthetic Communications, 40(23), 3452–3466.
https://doi.org/10.1080/00397910903435411
