(+)-FANGCHINOLINE Chemical Properties

Melting point:

240～242℃

Boiling point:

709.7±60.0 °C(Predicted)

Density 

1.204±0.06 g/cm3(Predicted)

storage temp. 

4°C, protect from light

solubility 

Soluble in chloroform and methanol;

pka

9.38±0.20(Predicted)

form 

powder to crystal

color 

White to Orange to Green

Water Solubility 

slightly soluble in water

Safety Information

HS Code 

2939.79.0000

(+)-FANGCHINOLINE Usage And Synthesis

Description

A bisbenzylisoquino!ine alkaloid obtained from Limacia cuspidata (Miers.) Hook. f. et Thorn., the base crystallizes from Me2CO in the form of long, colourless needles. It is strongly laevorotatory with [α]_D - 2120 (CHCI3) and has been shown to be the optical antipode of fanchinoline (q.v.).

Description

Fangchinoline is an alkaloid that has been found in S. tetrandrae and has diverse biological activities, including anti-inflammatory, neuroprotective, and anticancer properties. It inhibits the activity of sheep COX and decreases IL-6-induced proliferation of MH60 mouse hybridoma cells with IC₅₀ values of 129 and 3.7 μM, respectively. Fangchinoline (1 and 10 μM) reduces cyanide-induced increases in secreted glutamate levels and cell death in primary neonatal rat cerebellar granule neurons. It decreases proliferation of PC3 human prostate cancer cells by 63 and 86% when used at concentrations of 20 and 30 μM, respectively. Fangchinoline reduces tumor growth in a PC3 mouse xenograft model when administered at a dose of 5 mg/kg per day for 12 days.

Uses

(+)-Fangchinoline is an isolate from Stephania Tetrandra that shows anti-cancer activity. It inhibits breast adenocarcinoma proliferation through apoptosis induction. In addition, it has been shown to inhibit HIV-Type 1 replication.

Definition

ChEBI: A bisbenzylisoquinoline alkaloid that is (1beta)- berbaman which has been substituted by methyl groups at the 2 and 2' positions, by methoxy groups at the 6, 6', and 12 positions, and by a hydroxy group at position 7. Isolated from S ephania tetrandra, it has been found to possess neuroprotective and anti-tumour activity.

References

Tomita, Furukawa., Tetrahedron Lett., 4293 (1966)

(+)-FANGCHINOLINE(436-77-1)Related Product Information

• D-Tetrandrine
• veratramine
• Daurinoline
• VERATRINE
• ISOTETRANDRINE
• menisdaurin
• Xanthiside
• ISOCOLUMBIN
• Indigo
• Musk ketone
• Polysaccharide
• Protocatechualdehyde
• FORSYTHIN
• Glabridin
• Magnolia officinalis P.E.
• 7-O-isopropyl fangchinoline
• FANGCHINOLINE >90% BY HPLC
• 7-O-ethyl fangchinoline