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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H18O8
Molecular Weight 326.2986
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BILOBALIDE

SMILES

[H][C@]12C[C@@](O)(C(C)(C)C)[C@]34[C@@H](O)C(=O)O[C@@]3([H])OC(=O)[C@]14CC(=O)O2

InChI

InChIKey=MOLPUWBMSBJXER-YDGSQGCISA-N
InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8-,11-,13-,14+,15+/m0/s1

HIDE SMILES / InChI

Description

The sesquiterpene trilactone bilobalide is one of the active constituents of the 50:1 Ginkgo biloba leaf extract widely used to enhance memory and learning. Bilobalide was found to antagonise the direct action of gamma-aminobutyric acid (GABA) on recombinant alpha(1)beta(2)gamma(2L) GABA(A) receptors. Bilobalide showed anticonvulsant properties through the activation of glutamic acid decarboxylase (GAD) enzyme, which is a key enzyme in biosynthesis of GABA. Bilobalide has been proposed to exert protective and trophic effects on neurons. Bilobalide may be useful in developing therapy for diseases involving age-associated neurodegeneration. Bilobalide is an active component of EGb, a standardised extract of Ginkgo biloba leaves. Bilobalide accounts for about 3% of the total extract.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.6 µM [IC50]
12.0 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
11.16 ng/mL
1974.96 μg single, oral
BILOBALIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
29.38 ng × h/mL
1974.96 μg single, oral
BILOBALIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.52 h
1974.96 μg single, oral
BILOBALIDE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
Oral administration of bilobalide at 3 and 6 mg/kg/day
Route of Administration: Oral
In Vitro Use Guide
Bilobalide at 3, 10 and 30 uM increased GABA EC50 values: 1.5 times (56.0 –82.0 uM), 1.8 times (54.1 – 95.9 uM) and 2.7 times (67.7 –182.0 uM), respectively in in Xenopus laevis oocytes