Narciclasine is a plant growth inhibitor that can be isolated from Narcissus bulbs. At 1 μM, it has been shown to induce apoptosis-mediated cytotoxicity in human cancer cells in vitro but not in normal fibroblasts. Narciclasine has been shown to regulate the Rho/Rho kinase/LIM kinase/cofilin signaling pathway by increasing GTPase RhoA activity, as well as inducing actin stress fiber formation in a RhoA-dependent manner.
The bulbs of several Narcissus species contain this alkaloid which crystallizes in
the form of pale yellow needles with a pronounced yellow-green fluorescence. It
is best purified by recrystallization from either acetic acid or an aqueous mixture
of methoxyethyl alcohol. It is dextrorotatory with [α]589 + 145° or [Qh64 +
983° (c 1.5, EtOH). The ultraviolet spectrum in neutral solution (EtOH) has
absorption maxima at 252, 302 and 329 mil, while that in alkaline solution
(0.01 N/NaOH) has the maxima at 219, 249,310 and 355 mil. The O-methyl
ether forms shiny needles which also exhibit a strong blue fluorescence. The tri_x0002_acetate has been prepared as an amorphous, non-crystallizable substance. With
FeC13 the alkaloid gives a violet colour.
Narciclasine is an antiproliferative and pro-apoptotic inducer.
Narciclasine is reasonably abundant in some Narcissus spp. and has served as a very useful intermediate for synthetic conversion into (+)-pancratistatin and to conduct a series of structure–activity relationship studies . Bicolorine, another member of the narciclasine series, is an unusual, completely aromatized quaternary alkaloid with an N-methyl group.
ChEBI: A natural product found in Narcissus pseudonarcissus.
Immunology & Inflammation related
Ceriotti., Nature, 213,595 (1967)
Piozzi et al., Tetrahedron, 24, 1119 (1968)
Revised structure:
Mondon, Krohn., Tetrahedron Lett., 2123 (1970)
Savona, Piozzi, Marino., Chern. Cornrnun., 1006 (1970)
Absolute configuration:
Fuganti, Mazza.,J. Chern. Soc., Chern. Cornrnun., 239 (1972)
Crystal structure:
Immirzi, Fuganti., J. Chern. Soc., Chern. Cornrnun., 240 (1972)
Stereochemistry:
Mondon, Krohn., Tetrahedron Lett., 2085 (1972)
