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
SMILES
CC(C)(C)[C@]1(O)C[C@@H]2OC(=O)C[C@@]23C(=O)O[C@@H]4OC(=O)[C@H](O)[C@]134
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
| Molecular Formula | C15H18O8 |
| Molecular Weight | 326.2986 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12600688 | https://www.ncbi.nlm.nih.gov/pubmed/12457632Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26604665
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12600688 | https://www.ncbi.nlm.nih.gov/pubmed/12457632
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095172 |
4.6 µM [IC50] | ||
Target ID: GO:0051402 |
12.0 µM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11.16 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
29.38 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.52 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20041430 |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Spectroscopic investigation of Ginkgo biloba terpene trilactones and their interaction with amyloid peptide Abeta(25-35). | 2008-04 |
|
| 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. | 2008-03-15 |
|
| Simultaneous determination of ginkgo flavonoids and terpenoids in plasma: ammonium formate in LC mobile phase enhancing electrospray ionization efficiency and capacity. | 2008-03 |
|
| Restoration of impaired phosphorylation of cyclic AMP response element-binding protein (CREB) by EGb 761 and its constituents in Abeta-expressing neuroblastoma cells. | 2007-11 |
|
| Analysis of flavonol aglycones and terpenelactones in Ginkgo biloba extract: A comparison of high-performance thin-layer chromatography and column high-performance liquid chromatography. | 2007-10-25 |
|
| Effect of Ginkgo biloba extract on oxidative metabolism of valproic acid in hepatic microsomes from donors with the CYP2C9*1/*1 genotype. | 2007-09 |
|
| Characterization of a suite of ginkgo-containing standard reference materials. | 2007-09 |
|
| Drug treatment improves memory in mice. | 2007-07 |
|
| 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. | 2007-06-22 |
|
| Bilobalide in Ginkgo biloba extract is a major substance inducing hepatic CYPs. | 2007-06 |
|
| Acute cognitive effects of standardised Ginkgo biloba extract complexed with phosphatidylserine. | 2007-06 |
|
| Role of GABAergic antagonism in the neuroprotective effects of bilobalide. | 2007-01-12 |
|
| Bilobalide prevents ischemia-induced edema formation in vitro and in vivo. | 2007-01-05 |
|
| Treating senile dementia with traditional Chinese medicine. | 2007 |
|
| In vitro peroxynitrite scavenging activity of 6-hydroxykynurenic acid and other flavonoids from Gingko biloba yellow leaves. | 2006-12 |
|
| A screening platform for compounds with potential immuno-regulatory activities using human cord blood mononuclear cells. | 2006-12 |
|
| Analysis of ginkgolides and bilobalide in food products using LC-APCI-MS. | 2006-08-28 |
|
| Application of reverse-flow micellar electrokinetic chromatography for the simultaneous determination of flavonols and terpene trilactones in Ginkgo biloba dosage forms. | 2006-07-28 |
|
| Molecular determinants of ginkgolide binding in the glycine receptor pore. | 2006-07 |
|
| Effect of Ginkgo biloba extract on procarcinogen-bioactivating human CYP1 enzymes: identification of isorhamnetin, kaempferol, and quercetin as potent inhibitors of CYP1B1. | 2006-05-15 |
|
| Effect of supplementing terpenoid biosynthetic precursors on the accumulation of bilobalide and ginkgolides in Ginkgo biloba cell cultures. | 2006-05-03 |
|
| Determination of terpene trilactones in Ginkgo biloba solid oral dosage forms using HPLC with evaporative light scattering detection. | 2006-04-11 |
|
| 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. | 2006-02 |
|
| Distinct role of bilobalide and ginkgolide A in the modulation of rat CYP2B1 and CYP3A23 gene expression by Ginkgo biloba extract in cultured hepatocytes. | 2006-02 |
|
| Ginkgo biloba--an appraisal. | 2006-01-10 |
|
| 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 |
|
| [Quantitative determination of ginkgolides by liquid chromatography-electrospray mass spectrometry]. | 2005-12 |
|
| Suppression of pacemaker activity by Ginkgo biloba extract and its main constituent, bilobalide in rat sino-atrial nodal cells. | 2005-11-19 |
|
| A picrotoxin-specific conformational change in the glycine receptor M2-M3 loop. | 2005-10-28 |
|
| Preparative isolation of terpene trilactones from Ginkgo biloba leaves. | 2005-10-21 |
|
| Development of a ginkgo biloba fingerprint chromatogram with UV and evaporative light scattering detection and optimization of the evaporative light scattering detector operating conditions. | 2005-09-02 |
|
| Ginkgolides and bilobalide: their physical, chromatographic and spectroscopic properties. | 2005-09-01 |
|
| Terpene trilactones from Gingko biloba: from ancient times to the 21st century. | 2005-09-01 |
|
| Biological activities of Ginkgo extracts. | 2005-04 |
|
| Age-related changes in the vasodilating actions of Ginkgo biloba extract and its main constituent, bilobalide, in rat aorta. | 2005-04 |
|
| Liquid chromatography/electrospray tandem mass spectrometry of terpenoid lactones in Ginkgo biloba. | 2005-03 |
|
| Effects of ginkgo biloba extract on cation currents in rat ventricular myocytes. | 2005-01-21 |
|
| [Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts]. | 2005-01 |
|
| Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts. | 2004-11 |
|
| HPLC determination of certain flavonoids and terpene lactones in selected Ginkgo biloba L. phytopharmaceuticals. | 2004-09-23 |
|
| Sample preparation and determination of ginkgo terpene trilactones in selected beverage, snack, and dietary supplement products by liquid chromatography with evaporative light-scattering detection. | 2004-08-07 |
|
| A method for extraction and quantification of Ginkgo terpene trilactones. | 2004-08-01 |
|
| Inhibition of human cytochromes P450 by components of Ginkgo biloba. | 2004-08 |
|
| Preventive effects of extract of leaves of ginkgo (Ginkgo biloba) and its component bilobalide on azoxymethane-induced colonic aberrant crypt foci in rats. | 2004-07-16 |
|
| Determination of ginkgolide A, B, and bilobalide in biloba L. extracts by microdialysis-HPLC. | 2004-06 |
|
| [Studies on the cell growth, differentiation and terpene lactone accumulation in Ginkgo biloba cell suspension cultures]. | 2004-05 |
|
| Electropharmacological actions of Ginkgo biloba extract on vascular smooth and heart muscles. | 2004-04 |
|
| Chemistry and biology of terpene trilactones from Ginkgo biloba. | 2004-03-19 |
|
| Effect of Ginkgo biloba extract on rat hepatic microsomal CYP1A activity: role of ginkgolides, bilobalide, and flavonols. | 2004-01 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
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| Record UNII |
M81D2O8H7U
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| Record Status |
Validated (UNII)
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| Record Version |
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m2494
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BILOBALIDE
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DTXSID10873207
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33570-04-6
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SUB184976
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M81D2O8H7U
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