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

CAS: 15291-75-5 C20 H24 O9 MW: 408.40408000

Identification

Nameginkgolide A
CAS Number15291-75-5
FDA UNIITAZ2DPR77B
Molecular FormulaC20 H24 O9
Molecular Weight408.40408000
MDL NumberMFCD00133365

Regulatory

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)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for ginkgolide A usage levels up tonot for fragrance use.
Recommendation for ginkgolide A flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

ginkgo biloba

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 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.