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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
Terpene trilactones from Ginkgo biloba are antagonists of cortical glycine and GABA(A) receptors.
2003 Dec 5
Neuroprotective effects of bilobalide, a component of Ginkgo biloba extract (EGb 761) in global brain ischemia and in excitotoxicity-induced neuronal death.
2003 Jun
Analysis of ginkgolides and bilobalide in Ginkgo biloba L. extract injections by high-performance liquid chromatography with evaporative light scattering detection.
2003 Nov 24
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
A method for extraction and quantification of Ginkgo terpene trilactones.
2004 Aug 1
Effect of bilobalide on peripheral nerve regeneration.
2004 Feb
Effect of Ginkgo biloba extract on rat hepatic microsomal CYP1A activity: role of ginkgolides, bilobalide, and flavonols.
2004 Jan
Comparative vasodilating actions among terpenoids and flavonoids contained in Ginkgo biloba extract.
2004 Jan
Preventive effects of extract of leaves of ginkgo (Ginkgo biloba) and its component bilobalide on azoxymethane-induced colonic aberrant crypt foci in rats.
2004 Jul 16
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
Chemistry and biology of terpene trilactones from Ginkgo biloba.
2004 Mar 19
[Studies on the cell growth, differentiation and terpene lactone accumulation in Ginkgo biloba cell suspension cultures].
2004 May
Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts.
2004 Nov
Biological activities of Ginkgo extracts.
2005 Apr
Age-related changes in the vasodilating actions of Ginkgo biloba extract and its main constituent, bilobalide, in rat aorta.
2005 Apr
[Quantitative determination of ginkgolides by liquid chromatography-electrospray mass spectrometry].
2005 Dec
[Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts].
2005 Jan
Effects of ginkgo biloba extract on cation currents in rat ventricular myocytes.
2005 Jan 21
HPLC determination of certain flavonoids and terpene lactones in selected Ginkgo biloba L. phytopharmaceuticals.
2005 Jun-Jul
Liquid chromatography/electrospray tandem mass spectrometry of terpenoid lactones in Ginkgo biloba.
2005 Mar
Suppression of pacemaker activity by Ginkgo biloba extract and its main constituent, bilobalide in rat sino-atrial nodal cells.
2005 Nov 19
Preparative isolation of terpene trilactones from Ginkgo biloba leaves.
2005 Oct 21
A picrotoxin-specific conformational change in the glycine receptor M2-M3 loop.
2005 Oct 28
Ginkgolides and bilobalide: their physical, chromatographic and spectroscopic properties.
2005 Sep 1
Terpene trilactones from Gingko biloba: from ancient times to the 21st century.
2005 Sep 1
Development of a ginkgo biloba fingerprint chromatogram with UV and evaporative light scattering detection and optimization of the evaporative light scattering detector operating conditions.
2005 Sep 2
Quantitative determination of major active components in Ginkgo biloba dietary supplements by liquid chromatography/mass spectrometry.
2006
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
Analysis of ginkgolides and bilobalide in food products using LC-APCI-MS.
2006 Aug 28
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
Application of reverse-flow micellar electrokinetic chromatography for the simultaneous determination of flavonols and terpene trilactones in Ginkgo biloba dosage forms.
2006 Jul 28
Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: identification of isorhamnetin, kaempferol, and quercetin as potent inhibitors of CYP1B1.
2006 May 15
Effect of supplementing terpenoid biosynthetic precursors on the accumulation of bilobalide and ginkgolides in Ginkgo biloba cell cultures.
2006 May 3
Treating senile dementia with traditional Chinese medicine.
2007
Bilobalide prevents ischemia-induced edema formation in vitro and in vivo.
2007 Jan 5
Drug treatment improves memory in mice.
2007 Jul
Bilobalide in Ginkgo biloba extract is a major substance inducing hepatic CYPs.
2007 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
Effect of Ginkgo biloba extract on oxidative metabolism of valproic acid in hepatic microsomes from donors with the CYP2C9*1/*1 genotype.
2007 Sep
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
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