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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O4
Molecular Weight 382.4528
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ISOCORYNOXEINE

SMILES

[H][C@@]12C[C@@H]([C@H](CN1CC[C@@]23C(=O)NC4=CC=CC=C34)C=C)C(=C/OC)\C(=O)OC

InChI

InChIKey=MUVGVMUWMAGNSY-VKCGGMIFSA-N
InChI=1S/C22H26N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h4-8,13-15,19H,1,9-12H2,2-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22-/m0/s1

HIDE SMILES / InChI

Description

Isocorynoxeine is one of four bioactive tetracyclic oxinole alkaloids which can be isolated from Uncaria hooks used in traditional Chinese and Kampo medicines. The traditional remedies are claimed to have sedative and anti-spasmodic effects, however, isocorynoxeine does not appear to cross the blood-brain barrier. It is suspected that one or more metabolites of isocorynoxeine produce the effect of lower blood pressure, vasodilation and protection against ischemic neural damage. Furthermore, isocoynoxine has also shown reduce the viability of multi-drug resistant cancer cells when used in conjunction with doxycycline

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
13.7 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Secondary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
An oral dose of 40 mg/kg of isocorynoxeine was fed to rats. After dosing bile was drained and analyzed by LC-MS in order to identify metabolites of isocorynoxeine.
Route of Administration: Oral
In Vitro Use Guide
Isocorynooxeine and several metabolites were tested for the ability to protect against 3 mM glutamate-induced cell death in immortalized an HT22-cell line. HT22 cells were cultured in DMEM supplemented with 10% FBS at 37 deg-C in a 5% CO2 and 95% air atmosphere. Cells were incubated 24 hours before being treated with 1 - 100 micro-M of each test sample and 3 mM glutamate. Isocorynoxeine exhibited significant neuroprotective effects against glutamate-induced cell death at the maximum concentration of 100 micro-M. However little neuroprotection was observed for the tested metabolites.