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ginkgolide A
(1S,3R,7S,8S,9R,10S,12R,16S)-6,9,12,17-tetrahydroxy-16-methyl-8-(2-methyl-2-propanyl)-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione

Supplier Sponsors

CAS Number: 15291-75-5Picture of molecule3D/inchi
Other(deleted CASRN):119677-04-2
FDA UNII: TAZ2DPR77B
MDL:MFCD00133365
XlogP3-AA:0.60 (est)
Molecular Weight:408.40408000
Formula:C20 H24 O9
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 813.76 °C. @ 760.00 mm Hg (est)
Flash Point: 556.00 °F. TCC ( 291.40 °C. ) (est)
logP (o/w): 0.159 (est)
Soluble in:
 water, 2.331e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Ginkgolide A 98%
BOC Sciences
For experimental / research use only.
Ginkgolide A >98%
Odor: characteristic
Use: Ginkgolide A is an extract from in Ginkgo biloba and a g-aminobutyric acid (GABA) antagonist with a Ki of 14.5 ?M.
ExtraSynthese
For experimental / research use only.
Ginkgolide A (HPLC) ≥98%
Nacalai USA
For experimental / research use only.
Ginkgolide A
Santa Cruz Biotechnology
For experimental / research use only.
Ginkgolide A ≥98%
Sigma-Aldrich
For experimental / research use only.
Ginkgolide A from Ginkgo biloba leaves ≥90% (HPLC)
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for ginkgolide A usage levels up to:
 not for fragrance use.
 
Recommendation for ginkgolide A flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9909368
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0015291755
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9909368
Pubchem (sid):135347530
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C07601
HMDB (The Human Metabolome Database):HMDB36862
FooDB:FDB015816
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 ginkgo biloba
Search Trop Picture
 
Synonyms:
(1S,3R,7S,8S,9R,10S,12R,16S)-6,9,12,17-tetrahydroxy-16-methyl-8-(2-methyl-2-propanyl)-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
 

Articles:

PubMed:[Microfluidic evaporative light scattering detector coupled with capillary liquid chromatography and its application to Ginkgo biloba extract analysis].
PubMed:Two new nonacosanetriols from Ginkgo biloba sarcotesta.
PubMed:Ginkgolide X is a potent antagonist of anionic Cys-loop receptors with a unique selectivity profile at glycine receptors.
PubMed:Pharmacokinetics of bilobalide, ginkgolide A and B after administration of three different Ginkgo biloba L. preparations in humans.
PubMed:Chemical constituents of the bark of Machilus wangchiana and their biological activities.
PubMed:Self-emulsifying drug delivery systems for improving oral absorption of ginkgo biloba extracts.
PubMed:Transport of ginkgolides with different lipophilicities based on an hCMEC/D3 cell monolayer as a blood-brain barrier cell model.
PubMed:Interactions of pharmacokinetic profile of different parts from Ginkgo biloba extract in rats.
PubMed:Rapid process development of chromatographic process using direct analysis in real time mass spectrometry as a process analytical technology tool.
PubMed:Functional Module Connectivity Map (FMCM): a framework for searching repurposed drug compounds for systems treatment of cancer and an application to colorectal adenocarcinoma.
PubMed:Hepatoprotective effect of Ginkgo biloba leaf extract on lantadenes-induced hepatotoxicity in guinea pigs.
PubMed:Resistin increases monolayer permeability of human coronary artery endothelial cells.
PubMed:[Microfluidic evaporative light scattering detector coupled with capillary liquid chromatography and its application to Ginkgo biloba extract analysis].
PubMed:Neuroprotection against permanent focal cerebral ischemia by ginkgolides A and B is associated with obstruction of the mitochondrial apoptotic pathway via inhibition of c-Jun N-terminal kinase in rats.
PubMed:Toxicology and carcinogenesis studies of Ginkgo biloba extract (CAS No. 90045-36-6) in F344/N rats and B6C3F1/N mice (Gavage studies).
PubMed:Two new nonacosanetriols from Ginkgo biloba sarcotesta.
PubMed:Ginkgolic acid inhibits HIV protease activity and HIV infection in vitro.
PubMed:Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba.
PubMed:Effects of ginkgolide A on okadaic acid-induced tau hyperphosphorylation and the PI3K-Akt signaling pathway in N2a cells.
PubMed:Selective agonism of human pregnane X receptor by individual ginkgolides.
PubMed:Preconditioning with Ginkgo biloba (EGb 761®) provides neuroprotection through HO1 and CRMP2.
PubMed:Isoform-selective activation of human constitutive androstane receptor by Ginkgo biloba extract: functional analysis of the SV23, SV24, and SV25 splice variants.
PubMed:[Pharmacokinetics of ginkgolides sustained-release tablet].
PubMed:Ginkgolide A-gold nanoparticles inhibit vascular smooth muscle proliferation and migration in vitro and reduce neointimal hyperplasia in a mouse model.
PubMed:The combined effects of ginkgo biloba extracts and aspirin on viability of sk-N-mc, neuroblastoma cell line in hypoxia and reperfusion condition.
PubMed:Heme oxygenase 1, beneficial role in permanent ischemic stroke and in Gingko biloba (EGb 761) neuroprotection.
PubMed:EGb 761 (Ginkgo biloba) protects cochlear hair cells against ototoxicity induced by gentamicin via reducing reactive oxygen species and nitric oxide-related apoptosis.
PubMed:Plasma and brain levels of terpene trilactones in rats after an oral single dose of standardized Ginkgo biloba extract EGb 761®.
PubMed:Ginkgolide X is a potent antagonist of anionic Cys-loop receptors with a unique selectivity profile at glycine receptors.
PubMed:Chemical constituents of the bark of Machilus wangchiana and their biological activities.
PubMed:Inhibition of intestinal and hepatic glucuronidation of mycophenolic acid by Ginkgo biloba extract and flavonoids.
PubMed:Optimization of extraction technique and validation of developed RP-HPLC-ELSD method for determination of terpene trilactones in Ginkgo biloba leaves.
PubMed:Column liquid chromatography/electrospray ionization-time of flight-mass spectrometry and ultraperformance column liquid chromatography/mass spectrometry methods for the determination of ginkgolides and bilobalide in the leaves of Ginkgo biloba and dietary supplements.
PubMed:Roles and mechanisms of human immunodeficiency virus protease inhibitor ritonavir and other anti-human immunodeficiency virus drugs in endothelial dysfunction of porcine pulmonary arteries and human pulmonary artery endothelial cells.
PubMed:Chemical analysis and quality control of Ginkgo biloba leaves, extracts, and phytopharmaceuticals.
PubMed:Bioactive terpenoids and flavonoids from Ginkgo biloba extract induce the expression of hepatic drug-metabolizing enzymes through pregnane X receptor, constitutive androstane receptor, and aryl hydrocarbon receptor-mediated pathways.
PubMed:Self-emulsifying drug delivery systems for improving oral absorption of ginkgo biloba extracts.
PubMed:Validation of capillary gas chromatographic method for determination of bilobalide and ginkgolides A, B, C in Ginkgo biloba dry and liquid extracts.
PubMed:[Optimized preparation of ginkgolides A and B long-circulating solid lipid nanoparticles by central composite design and response surface method].
PubMed:Induction of cytochrome P450s by terpene trilactones and flavonoids of the Ginkgo biloba extract EGb 761 in rats.
PubMed: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.
PubMed:Structure-activity analysis of ginkgolide binding in the glycine receptor pore.
PubMed:Effect of Ginkgo biloba extract on oxidative metabolism of valproic acid in hepatic microsomes from donors with the CYP2C9*1/*1 genotype.
PubMed:Analysis of flavonol aglycones and terpenelactones in Ginkgo biloba extract: A comparison of high-performance thin-layer chromatography and column high-performance liquid chromatography.
PubMed:Spectroscopic investigation of Ginkgo biloba terpene trilactones and their interaction with amyloid peptide Abeta(25-35).
PubMed:Induction of cyp3a in primary cultures of human hepatocytes by ginkgolides a and B.
PubMed: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.
PubMed:Acute cognitive effects of standardised Ginkgo biloba extract complexed with phosphatidylserine.
PubMed:Ginkgo biloba and ovarian cancer prevention: epidemiological and biological evidence.
PubMed:Amyloid-beta-induced pathological behaviors are suppressed by Ginkgo biloba extract EGb 761 and ginkgolides in transgenic Caenorhabditis elegans.
PubMed:Ginkgolide A contributes to the potentiation of acetaminophen toxicity by Ginkgo biloba extract in primary cultures of rat hepatocytes.
PubMed:Ginkgo biloba leaf extract reverses amyloid beta-peptide-induced isoprostane production in rat brain in vitro.
PubMed:Ginkgolide A attenuates homocysteine-induced endothelial dysfunction in porcine coronary arteries.
PubMed:Molecular determinants of ginkgolide binding in the glycine receptor pore.
PubMed:Paradoxical effects of ginkgolide B on cardiomyocyte contractile function in normal and high-glucose environments.
PubMed:[Quantitative determination of ginkgolides by liquid chromatography-electrospray mass spectrometry].
PubMed:Determination of terpene trilactones in Ginkgo biloba solid oral dosage forms using HPLC with evaporative light scattering detection.
PubMed:LC-MS characterization of terpene lactones in plasma of experimental animals treated with Ginkgo biloba extracts Correlation with pharmacological activity.
PubMed:Ginkgolides induce apoptosis and decrease cell numbers in mouse blastocysts.
PubMed:Distinct role of bilobalide and ginkgolide A in the modulation of rat CYP2B1 and CYP3A23 gene expression by Ginkgo biloba extract in cultured hepatocytes.
PubMed:Lactone-free ginkgolides via regioselective DIBAL-H reduction.
PubMed:[Studies on the cell growth, differentiation and terpene lactone accumulation in Ginkgo biloba cell suspension cultures].
PubMed:HPLC determination of certain flavonoids and terpene lactones in selected Ginkgo biloba L. phytopharmaceuticals.
PubMed:Biological activities of Ginkgo extracts.
PubMed:Comparative Electropharmacological Actions of Some Constituents from Ginkgo biloba Extract in Guinea-pig Ventricular Cardiomyocytes.
PubMed:Effects of ginkgo biloba extract on cation currents in rat ventricular myocytes.
PubMed:Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts.
PubMed:Microglial calcium responses to platelet-activating factor are inhibited by analogue CAS 99103-16-9 and dihydropyridine PCA 4248 but not by ginkgolide A.
PubMed:A new geranylgeranyl diphosphate synthase gene from Ginkgo biloba, which intermediates the biosynthesis of the key precursor for ginkgolides.
PubMed:Effect of ginkgolides on beta-amyloid-suppressed acetylocholine release from rat hippocampal slices.
PubMed:A method for extraction and quantification of Ginkgo terpene trilactones.
PubMed:Ginkgolides, diterpene trilactones of Ginkgo biloba, as antagonists at recombinant alpha1beta2gamma2L GABAA receptors.
PubMed:[Determination of GA, GB and GC in total lactone of ginkgo (TLG) raw material].
PubMed:Determination of ginkgolide A, B, and bilobalide in biloba L. extracts by microdialysis-HPLC.
PubMed:An anxiolytic-like effect of Ginkgo biloba extract and its constituent, ginkgolide-A, in mice.
PubMed:Pharmacological studies supporting the therapeutic use of Ginkgo biloba extract for Alzheimer's disease.
PubMed:Liquid chromatography/atmospheric pressure chemical ionization ion trap mass spectrometry of terpene lactones in plasma of animals.
PubMed:Homocysteine stimulates inducible nitric oxide synthase expression in macrophages: antagonizing effect of ginkgolides and bilobalide.
PubMed: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.
PubMed:[Inhibitory effects of ginkgolide B on proliferation of bovine aortic smooth muscle cells].
PubMed:[Analysis and structure identification of trace constituent in the total ginkgolide by using LC/DAD/ESI/MS].
PubMed:Rapid analysis of terpene lactones in extract of Ginkgo biloba L. by high performance liquid chromatography.
PubMed:Influence of pharmaceutical quality on the bioavailability of active components from Ginkgo biloba preparations.
PubMed:Identification and the retention index of bilobalide and ginkgolides using capillary gas chromatography.
PubMed:Ginkgolide A, B, and huperzine A inhibit nitric oxide-induced neurotoxicity.
PubMed:Simultaneous determination of terpene lactones and flavonoid aglycones in Ginkgo biloba by high-performance liquid chromatography with evaporative light scattering detection.
PubMed:Effects of extract of Ginkgo biloba leaves and its constituents on carcinogen-metabolizing enzyme activities and glutathione levels in mouse liver.
PubMed:Three ginkgolide hydrates from Ginkgo biloba L.: ginkgolide A monohydrate, ginkgolide C sesquihydrate and ginkgolide J dihydrate, all determined at 120 K.
PubMed:Synthesis and biological activity of amide derivatives of ginkgolide A.
PubMed:Ginkgolide A, B, and huperzine A inhibit nitric oxide production from rat C6 and human BT325 glioma cells.
PubMed:Inhibition by ginkgolides and bilobalide of the production of nitric oxide in macrophages (THP-1) but not in endothelial cells (HUVEC).
PubMed:Complementary cardioprotective effects of flavonoid metabolites and terpenoid constituents of Ginkgo biloba extract (EGb 761) during ischemia and reperfusion.
PubMed:Immunomodulating components from chinese medicines.
PubMed:Effects of single intraperitoneal injections of an extract of Ginkgo biloba (EGb 761) and its terpene trilactone constituents on barbital-induced narcosis in the mouse.
PubMed:Inhibitory effects of ginkgolides on nitric oxide production in neonatal rat microglia in vitro.
PubMed:Bioavailability of ginkgolides and bilobalide from extracts of ginkgo biloba using GC/MS.
PubMed:Inhibition of serum deprivation- and staurosporine-induced neuronal apoptosis by Ginkgo biloba extract and some of its constituents.
PubMed:Effects of ginkgolides on interleukin-1, tumor necrosis factor-alpha and nitric oxide production by rat microglia stimulated with lipopolysaccharides in vitro.
PubMed:Antioxidative activity of ginkgolides against superoxide in an aprotic environment.
PubMed:Cardioprotective and anti-oxidant effects of the terpenoid constituents of Ginkgo biloba extract (EGb 761).
PubMed:In vivo regulation of peripheral-type benzodiazepine receptor and glucocorticoid synthesis by Ginkgo biloba extract EGb 761 and isolated ginkgolides.
PubMed:[Pharmacokinetic properties of Bilobalide and Ginkgolides A and B in healthy subjects after intravenous and oral administration of Ginkgo biloba extract (EGb 761)].
PubMed:Ginkgolide B accelerates vestibular compensation of spontaneous ocular nystagmus in guinea pig following unilateral labyrinthectomy.
PubMed:Isolation of bilobalide and ginkgolide A from Ginkgo biloba L. shorten the sleeping time induced in mice by anesthetics.
 
Notes:
Bitter principle from Ginkgo biloba (ginkgo)
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