Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H19NO3 |
Molecular Weight | 297.3484 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1)C(O)CNC(=O)\C=C\C2=CC=CC=C2
InChI
InChIKey=QRFDENJATPJOKG-KPKJPENVSA-N
InChI=1S/C18H19NO3/c1-22-16-10-8-15(9-11-16)17(20)13-19-18(21)12-7-14-5-3-2-4-6-14/h2-12,17,20H,13H2,1H3,(H,19,21)/b12-7+
Aegeline is a compound extracted from Aegle marmelos (bael), a plant that has a long history of use in Ayurvedic medicine. Aegeline inhibited the histamine release from RBL-2H3 cells induced by DNP(24)-BSA. Aegeline showed strong inhibition when RBL-2H3 cells induced by Ca(2+) stimulants such as thapsigargin and ionomycin. Tthe inhibitory effects of aegeline on the histamine release from mast cells depended on the type of mast cell and also involved some mechanisms related to intracellular Ca(2+) signaling events via the same target of the action of thapsigargin or downstream process of intracellular Ca(2+) signaling in mast cells. Aegeline has shown antihyperglycemic as well as antidyslipidemic activities in the validated animal models of type 2 diabetes mellitus. Although some evidence from animal studies suggests that aegeline might lower blood sugar, this potential effect has never been studied in humans. This compound has been used as an ingredient in weight-loss aid products too, but again there is no evidence that it is effective for weight loss in humans. FDA recently issued an information update stating that FDA along with the Centers for Disease Control and Prevention are investigating more that 50 cases of liver damage. FDA also issued a warning letter to a company marketing a dietary supplement that contains aegeline, because it is not currently recognized as a legitimate ingredient for dietary supplements.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21930379 |
|||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26247834 |
76.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17197179
Rats: Treatment with Aegeline lowered the blood glucose by
12.9% at 5 h and 16.9% at 24 h at 100 mg/kg body.
Hamsters: Aegeline was administered orally at the dose of 50 mg/kg body weight for seven consecutive days weight dose.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23972792
Aegeline was screened for the adipogenesis inhibition at 50 and 100 uM concentrations. Aegeline was showing 16.29±0.85% lipid content at 100 μM.
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SUBSTANCE RECORD