U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O9
Molecular Weight 408.3992
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GINKGOLIDE A

SMILES

C[C@@H]1C(=O)O[C@H]2C[C@@]34[C@H]5C[C@@H](C(C)(C)C)[C@@]36[C@@H](O)C(=O)O[C@H]6O[C@@]4(C(=O)O5)[C@@]12O

InChI

InChIKey=FPUXKXIZEIDQKW-VKMVSBOZSA-N
InChI=1S/C20H24O9/c1-7-12(22)26-10-6-17-9-5-8(16(2,3)4)18(17)11(21)13(23)28-15(18)29-20(17,14(24)27-9)19(7,10)25/h7-11,15,21,25H,5-6H2,1-4H3/t7-,8+,9-,10+,11+,15+,17-,18+,19-,20-/m1/s1

HIDE SMILES / InChI

Description

Ginkgolide A (GA, BN52020), is a terpene lactone constituent of Ginkgo biloba, the ginkgo tree, is the oldest living tree, with a long history of use in traditional Chinese medicine. Ginkgolide A is an effective antagonist of platelet activating factor, an ubiquitous phospholipid that acts as a mediator of numerous pathophysiological conditions. Ginkgolide A displays anxiolytic, antiinflammatory properties, protects from cerebral ischemia in animal models.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
9.7 µM [IC50]
14.5 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Daily administration of ginkgolide-A in mice (1 or 2 mg/kg, po) resulted in an anxiolytic-like effect by the third treatment, with the maximal effect observed after the fifth administration. Ginkgolide A (GA, BN52020) (ED50 = 1.1 mg/kg i.v.) inhibit bronchospasms, hypotension and concomitant generation of TXA2-like activity induced by PAF-acether in anaesthetized guinea-pigs. Combined pre- and post-treatment with the Ginkgolide A (2 x 25 mg/kg, s.c.) significantly reduced the resulting neuronal damage of the CA1 and CA3 hippocampal subfields and of the occipital and parietal cerebral cortex in rat.
Route of Administration: Other
In Vitro Use Guide
The endothelial production of high-glucose-induced interleukin (IL)-4, IL-6, IL-13 and signal transducer and activator of transcription-3 (STAT-3) phosphorylation were significantly inhibited by the pretreatment with Ginkgolide A at concentrations of 10, 15 and 20μM