narciclasine Chemical Properties

Melting point:

250-252℃

Boiling point:

447.77°C (rough estimate)

Density 

1.85±0.1 g/cm3 (20 ºC 760 Torr)

refractive index 

1.5300 (estimate)

storage temp. 

Store at -20°C

solubility 

DMSO: ≥10mg/mL

pka

7.72±0.70(Predicted)

form 

Solid

color 

white to off-white

Safety Information

Hazard Codes 

Xn

Risk Statements 

46

Safety Statements 

36

narciclasine Usage And Synthesis

Description

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.

Description

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.

Uses

Narciclasine is an antiproliferative and pro-apoptotic inducer.

Uses

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.

Definition

ChEBI: A natural product found in Narcissus pseudonarcissus.

target

Immunology & Inflammation related

storage

Store at -20°C

References

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)

narciclasine(29477-83-6)Related Product Information

• Daurinoline
• daurisoline
• Colchicine
• 2,4-Dihydroxy-N-(2-hydroxyethyl)benzamide
• 1-(3,4-Methylenedioxyphenyl)-2-butanamine
• N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine
• narciclasine
• 1-PHENYL-1-CYCLOHEXENE
• 4-Methoxysalicylamide
• 6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE
• 7,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]ISOQUINOLIN-5(6H)-ONE
• 6-METHYL-BENZO[1,3]DIOXOLE-5-CARBALDEHYDE
• 8-HYDROXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• 7-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• 7-HYDROXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• (R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL
• 6,7-DIHYDROXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• 6-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE