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Details

Stereochemistry RACEMIC
Molecular Formula C18H19NO3
Molecular Weight 297.349
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AEGELINE

SMILES

COc1ccc(cc1)C(CN=C(/C(/[H])=C(\[H])/c2ccccc2)O)O

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+

HIDE SMILES / InChI
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

Targets

Primary TargetPharmacologyConditionPotency
76 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Effects of aegeline, a main alkaloid of Aegle Marmelos Correa leaves, on the histamine release from mast cells.
2011 Jul
Two new cytotoxic furoquinoline alkaloids isolated from Aegle marmelos (Linn.) Correa.
2016 Nov
Patents

Sample Use Guides

Rats: Treatment with Aegeline lowered the blood glucose by
Route of Administration: Oral
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.
Name Type Language
AEGELINE
Common Name English
EGELINE
Common Name English
EGELINE [USP-RS]
Common Name English
2-PROPENAMIDE, N-(2-HYDROXY-2-(4-METHOXYPHENYL)ETHYL)-3-PHENYL-, (E)-(+/-)-
Systematic Name English
AEGELIN
Common Name English
Code System Code Type Description
FDA UNII
60T59LN3SG
Created by admin on Sat Jun 26 04:45:28 UTC 2021 , Edited by admin on Sat Jun 26 04:45:28 UTC 2021
PRIMARY
CAS
456-12-2
Created by admin on Sat Jun 26 04:45:28 UTC 2021 , Edited by admin on Sat Jun 26 04:45:28 UTC 2021
PRIMARY
USP_CATALOG
1234260
Created by admin on Sat Jun 26 04:45:28 UTC 2021 , Edited by admin on Sat Jun 26 04:45:28 UTC 2021
PRIMARY USP-RS
PUBCHEM
15558419
Created by admin on Sat Jun 26 04:45:28 UTC 2021 , Edited by admin on Sat Jun 26 04:45:28 UTC 2021
PRIMARY
EVMPD
SUB129641
Created by admin on Sat Jun 26 04:45:28 UTC 2021 , Edited by admin on Sat Jun 26 04:45:28 UTC 2021
PRIMARY