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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H18O8
Molecular Weight 326.2992
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BILOBALIDE

SMILES

CC(C)(C)[C@@]1(C[C@@]2([H])[C@@]3(CC(=O)O2)C(=O)O[C@@]4([H])[C@]31[C@]([H])(C(=O)O4)O)O

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

Molecular Formula C15H18O8
Molecular Weight 326.2992
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26604665

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.

Approval Year

Targets

Targets

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

Cmax

ValueDoseCo-administeredAnalytePopulation
11.16 ng/mL
1974.96 μg single, oral
dose: 1974.96 μg
route of administration: Oral
experiment type: SINGLE
co-administered: GINKGOLIDE A|ginkgolide B
BILOBALIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
29.38 ng × h/mL
1974.96 μg single, oral
dose: 1974.96 μg
route of administration: Oral
experiment type: SINGLE
co-administered: GINKGOLIDE A|ginkgolide B
BILOBALIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.52 h
1974.96 μg single, oral
dose: 1974.96 μg
route of administration: Oral
experiment type: SINGLE
co-administered: GINKGOLIDE A|ginkgolide B
BILOBALIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Protective effect of bilobalide against nitric oxide-induced neurotoxicity in PC12 cells.
2000 May
[Analysis and structure identification of trace constituent in the total ginkgolide by using LC/DAD/ESI/MS].
2001 Aug
Neuroprotective effects of bilobalide, a component of the Ginkgo biloba extract (EGb 761), in gerbil global brain ischemia.
2001 Dec 20
Induction of heme oxygenase-1 by Ginkgo biloba extract but not its terpenoids partially mediated its protective effect against lysophosphatidylcholine-induced damage.
2001 Jan
Mitochondrial respiratory chain as a new target for anti-ischemic molecules.
2002 Apr 19
Chemical analysis of Ginkgo biloba leaves and extracts.
2002 Aug 16
Simultaneous determination of terpene lactones and flavonoid aglycones in Ginkgo biloba by high-performance liquid chromatography with evaporative light scattering detection.
2002 Aug 22
Effects of bilobalide on amino acid release and electrophysiology of cortical slices.
2002 Jun
Liquid chromatography-electrospray mass spectrometric studies of ginkgolides and bilobalide using simultaneous monitoring of proton, ammonium and sodium adducts.
2002 May
Efficient extraction of ginkgolides and bilobalide from Ginkgo biloba leaves.
2002 Oct
Effects of chronic administration of bilobalide on amino acid levels in mouse brain.
2002 Sep
Bilobalide, a component of the Ginkgo biloba extract (EGb 761), protects against neuronal death in global brain ischemia and in glutamate-induced excitotoxicity.
2002 Sep
Liquid chromatography/atmospheric pressure chemical ionization ion trap mass spectrometry of terpene lactones in plasma of animals.
2003 Aug 8
Terpene trilactones from Ginkgo biloba are antagonists of cortical glycine and GABA(A) receptors.
2003 Dec 5
Development and validation of a gas chromatographic-mass spectrometric method for simultaneous identification and quantification of marker compounds including bilobalide, ginkgolides and flavonoids in Ginkgo biloba L. extract and pharmaceutical preparations.
2003 Jan 31
Neuroprotective effects of bilobalide, a component of Ginkgo biloba extract (EGb 761) in global brain ischemia and in excitotoxicity-induced neuronal death.
2003 Jun
Effects of bilobalide on cerebral amino acid neurotransmission.
2003 Jun
Excitotoxic hippocampal membrane breakdown and its inhibition by bilobalide: role of chloride fluxes.
2003 Jun
Structure-activity studies with Ginkgo biloba extract constituents as receptor-gated chloride channel blockers and modulators.
2003 Jun
Pharmacokinetics of Ginkgo biloba extracts.
2003 Jun
Cognitive and other behavioral effects of EGb 761 in animal models.
2003 Jun
Pharmacological studies supporting the therapeutic use of Ginkgo biloba extract for Alzheimer's disease.
2003 Jun
An anxiolytic-like effect of Ginkgo biloba extract and its constituent, ginkgolide-A, in mice.
2003 Oct
Electropharmacological actions of Ginkgo biloba extract on vascular smooth and heart muscles.
2004 Apr
Inhibition of human cytochromes P450 by components of Ginkgo biloba.
2004 Aug
Effect of bilobalide on peripheral nerve regeneration.
2004 Feb
Sample preparation and determination of ginkgo terpene trilactones in selected beverage, snack, and dietary supplement products by liquid chromatography with evaporative light-scattering detection.
2004 Jul-Aug
Ginkgo biloba--an appraisal.
2004 Jul-Sep
Determination of ginkgolide A, B, and bilobalide in biloba L. extracts by microdialysis-HPLC.
2004 Jun
Age-related changes in the vasodilating actions of Ginkgo biloba extract and its main constituent, bilobalide, in rat aorta.
2005 Apr
HPLC determination of certain flavonoids and terpene lactones in selected Ginkgo biloba L. phytopharmaceuticals.
2005 Jun-Jul
Suppression of pacemaker activity by Ginkgo biloba extract and its main constituent, bilobalide in rat sino-atrial nodal cells.
2005 Nov 19
Terpene trilactones from Gingko biloba: from ancient times to the 21st century.
2005 Sep 1
Mixed antagonistic effects of bilobalide at rho1 GABAC receptor.
2006
Determination of terpene trilactones in Ginkgo biloba solid oral dosage forms using HPLC with evaporative light scattering detection.
2006 Apr 11
In vitro peroxynitrite scavenging activity of 6-hydroxykynurenic acid and other flavonoids from Gingko biloba yellow leaves.
2006 Dec
Identification of class 2 1-deoxy-D-xylulose 5-phosphate synthase and 1-deoxy-D-xylulose 5-phosphate reductoisomerase genes from Ginkgo biloba and their transcription in embryo culture with respect to ginkgolide biosynthesis.
2006 Feb
Distinct role of bilobalide and ginkgolide A in the modulation of rat CYP2B1 and CYP3A23 gene expression by Ginkgo biloba extract in cultured hepatocytes.
2006 Feb
Molecular determinants of ginkgolide binding in the glycine receptor pore.
2006 Jul
Single-laboratory validation for the determination of terpene lactones in Ginkgo biloba dietary supplement crude materials and finished products by high-performance liquid chromatography with evaporative light-scattering detection.
2007 May-Jun
Restoration of impaired phosphorylation of cyclic AMP response element-binding protein (CREB) by EGb 761 and its constituents in Abeta-expressing neuroblastoma cells.
2007 Nov
Analysis of flavonol aglycones and terpenelactones in Ginkgo biloba extract: A comparison of high-performance thin-layer chromatography and column high-performance liquid chromatography.
2007 Sep-Oct
Simultaneous determination of ginkgo flavonoids and terpenoids in plasma: ammonium formate in LC mobile phase enhancing electrospray ionization efficiency and capacity.
2008 Mar
Simultaneous determination of ginkgolides A, B, C and bilobalide in plasma by LC-MS/MS and its application to the pharmacokinetic study of Ginkgo biloba extract in rats.
2008 Mar 15
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Also was used subcutaneously. In focal cerebral ischemia models, the administration of bilobalide (5-20 mg/kg, s. c.) 60 min before ischemia dose-dependently reduced the infarct area in mouse brain and the infarct volume in rat brain 2 days after the onset of the injury. https://www.ncbi.nlm.nih.gov/pubmed/13130383
Oral administration of bilobalide at 3 and 6 mg/kg/day
Route of Administration: Oral
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:00:54 UTC 2021
Edited
by admin
on Sat Jun 26 08:00:54 UTC 2021
Record UNII
M81D2O8H7U
Record Status Validated (UNII)
Record Version
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Name Type Language
BILOBALIDE
MI  
Common Name English
BILOBALIDE [WHO-DD]
Common Name English
BILOBALIDE [MI]
Common Name English
BILOBALIDE (CONSTITUENT OF GINKGO) [DSC]
Common Name English
BILOBALID
Common Name English
(-)-BILOBALIDE
Common Name English
4H,5AH,9H-FURO(2,3-B)FURO(3',2':2,3)CYCLOPENTA(1,2-C)FURAN-2,4,7(3H,8H)-TRIONE, 9-(1,1-DIMETHYLETHYL)-10,10A-DIHYDRO-8,9-DIHYDROXY-, (3AS,5AR,8R,8AS,9R,10AS)-
Common Name English
Code System Code Type Description
MERCK INDEX
M2494
Created by admin on Sat Jun 26 08:00:54 UTC 2021 , Edited by admin on Sat Jun 26 08:00:54 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
BILOBALIDE
Created by admin on Sat Jun 26 08:00:54 UTC 2021 , Edited by admin on Sat Jun 26 08:00:54 UTC 2021
PRIMARY
PUBCHEM
73581
Created by admin on Sat Jun 26 08:00:54 UTC 2021 , Edited by admin on Sat Jun 26 08:00:54 UTC 2021
PRIMARY
CAS
33570-04-6
Created by admin on Sat Jun 26 08:00:54 UTC 2021 , Edited by admin on Sat Jun 26 08:00:54 UTC 2021
PRIMARY
EVMPD
SUB184976
Created by admin on Sat Jun 26 08:00:54 UTC 2021 , Edited by admin on Sat Jun 26 08:00:54 UTC 2021
PRIMARY
FDA UNII
M81D2O8H7U
Created by admin on Sat Jun 26 08:00:54 UTC 2021 , Edited by admin on Sat Jun 26 08:00:54 UTC 2021
PRIMARY
Related Record Type Details
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