| Identification | Back Directory | [Name]
(+)-FANGCHINOLINE | [CAS]
436-77-1 | [Synonyms]
(+)-limacine
Tetrandrine B
Hanfangichin B
FANGCHINO-LINE
(+)-FANGCHINOLINE
FANGCHINOLINE (RG)
7-o-demethyltetrandrine
12-O-MethylatherosperMoline
Hanfangchin B（Fangchinoline）
Fangchinoline,
Demethyltetrandrine
6,6',12-TRIMETHOXY-2,2'-DIMETHYLBERBAMAN-7-OL
(1S)-6,6',12-Trimethoxy-2,2'-dimethylberbaman-7-ol
2’-dimethyl-6,6’,12-trimethoxy-(1-beta)-berbaman-7-o
(1-beta)-2,2’-dimethyl-6,6’,12-trimethoxyberbaman-7-ol
Berbaman-7-ol,6,6',12-trimethoxy-2,2'-dimethyl-, (1β)-
(1S)-7-Hydroxy-6,6',12-trimethoxy-2,2'-dimethylberbaman | [Molecular Formula]
C37H40N2O6 | [MDL Number]
MFCD00221726 | [MOL File]
436-77-1.mol | [Molecular Weight]
608.72 |
| Chemical Properties | Back Directory | [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; | [form ]
powder to crystal | [pka]
9.38±0.20(Predicted) | [color ]
White to Orange to Green | [Water Solubility ]
slightly soluble in water | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChIKey]
IIQSJHUEZBTSAT-VMPREFPWSA-N | [SMILES]
OC1C(=CC2CCN([C@@]3([H])CC4=CC=C(C(OC5=CC=C(C=C5)C[C@]5([H])N(CCC6=CC(=C(C=C65)OC=1C3=2)OC)C)=C4)OC)C)OC |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [HS Code ]
2939.79.0000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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.1,2,3 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.1 Fangchinoline (1 and 10 μM) reduces cyanide-induced increases in secreted glutamate levels and cell death in primary neonatal rat cerebellar granule neurons.2 It decreases proliferation of PC3 human prostate cancer cells by 63 and 86% when used at concentrations of 20 and 30 μM, respectively.3 Fangchinoline reduces tumor growth in a PC3 mouse xenograft model when administered at a dose of 5 mg/kg per day for 12 days. | [Chemical Properties]
Derived from the burned root of Stephania tetrandra S. Moore, a plant of the Menispermaceae family | [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. | [IC 50]
HIV-1 | [References]
Tomita, Furukawa., Tetrahedron Lett., 4293 (1966) |
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