GINKGOLIDE A

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 Search

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

Molecular Formula	C20H24O9
Molecular Weight	408.3992
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15038029
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26604665

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 Target	Pharmacology	Potency
platelet activating factor metabolic process 2 Target ID: GO:0046469 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2820421	Inhibitor 8504	9.7 µM [IC50]
Pregnane X receptor 36 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22393123 \| https://www.ncbi.nlm.nih.gov/pubmed/20739453 \| https://www.ncbi.nlm.nih.gov/pubmed/26759700	Agonist 2752
GABA-A receptor; alpha-1/beta-2/gamma-2 28 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15212966 \| https://www.ncbi.nlm.nih.gov/pubmed/26953225	Antagonist 2849	14.5 µM [Ki]
Platelet activating factor receptor 20 Target ID: CHEMBL250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26604665 \| https://www.ncbi.nlm.nih.gov/pubmed/2850196 \| https://www.ncbi.nlm.nih.gov/pubmed/12076171	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Hepatitis 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26759700	Primary	Basic research	Unknown Approved Use Unknown
Anxiety 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14575433/	Primary	Basic research	Unknown Approved Use Unknown
Stroke 144 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3432553 https://www.ncbi.nlm.nih.gov/pubmed/8095559 https://www.ncbi.nlm.nih.gov/pubmed/24327346	Primary	Basic research	Unknown Approved Use Unknown
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3099317	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Modulation of CYP1A1 activity by a Ginkgo biloba extract in the human intestinal Caco-2 cells.	2011-05-10	21329749
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.	2009-04	19034627
Induction of cytochrome P450s by terpene trilactones and flavonoids of the Ginkgo biloba extract EGb 761 in rats.	2008-05	18421621
Ginkgolide A contributes to the potentiation of acetaminophen toxicity by Ginkgo biloba extract in primary cultures of rat hepatocytes.	2006-12-01	17045319
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	16258077
Ginkgolide A, B, and huperzine A inhibit nitric oxide-induced neurotoxicity.	2002-10	12433056

Patents

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:31:32 GMT 2025` Edited by `admin` on `Mon Mar 31 21:31:32 GMT 2025`
Record UNII	TAZ2DPR77B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GINKGOLIDE A

Common Name

English

9H-1,7A-(EPOXYMETHANO)-1H,6AH-CYCLOPENTA(C)FURO(2,3-B)FURO(3',2':3,4)CYCLOPENTA(1,2-D)FURAN-5,9,12(4H)-TRIONE, 3-(1,1-DIMETHYLETHYL)HEXAHYDRO-4,7B-DIHYDROXY-8-METHYL-, (1R,3S,3AS,4R,6AR,7AR,7BR,8S,10AS,11AS)-

Preferred Name

English

BN-52020

Common Name

English

Ginkgolide A [WHO-DD]

Common Name

English

GINKGOLIDE A [MI]

Common Name

English

GINKGOLIDE A (CONSTITUENT OF GINKGO) [DSC]

Common Name

English

Classification Tree Code System Code

DSLD

2519 (Number of products:2)