BILOBALIDE

Synonyms. (5aR-(3aS',5aalpha,8beta,8aS',9alpha,10aalpha))-9-(1,1-Dimethylethyl)-10,10a-dihydro-8,9-dihydroxy- 4H,5aH,9H-furo(2,3-b)furo(3',2':2,3)cyclopenta(1,2-c)furan-2,4,7(3H,8H)-trione;

BILOBALIDE

 

PRODUCT IDENTIFICATION

CAS RN

33570-04-6

EINECS RN

 

FORMULA

C15H18O8

MOLE WEIGHT

326.30

H.S CODE

2932.29.5050

SMILES

C1([C@@]23[C@@]4([C@@](C[C@@H]2OC(C3)=O)(C(C)(C)C)O)[C@H] (O1)OC ([C@@H]4O)=O)=O

CLASSIFICATION

Ginkgolide

EXTRA NOTES

Bioactive main constituent of the terpenoids found in Ginkgo biloba.

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white to off-white powder

MELTING POINT

 

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

 

SOLVENT SOLUBILITY Soluble in alcohol, DMSO

VAPOR DENSITY

 

log P(octanol-water)

 

VAPOR PRESSURE

 

AUTOIGNITION TEMP

 
pH

 

REFRACTIVE INDEX

 

FLASH POINT

 

 

STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents

POLYMERIZATION

Has not been reported

NFPA RATINGS

 

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking

Google Scholar Search

Drug Information Portal (U.S. National Library of Medicine) - Bilobalide

PubChem Compound Summary - Bilobalide

Drug Bank - Bilobalide

KEGG (Kyoto Encyclopedia of Genes and Genomes) -  Bilobalide

http://www.ebi.ac.uk/chebi/ -  Bilobalide

http://www.ncbi.nlm.nih.gov/ - Bilobalide

http://sydney.edu.au/
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 g-aminobutyric acid (GABA) on recombinant a1h2g2L GABAA receptors. The effect of bilobalide on the direct action of GABA at a1h2g2L GABAA receptors expressed in Xenopus laevis oocytes using two-electrode voltage-clamp method was evaluated and compared with the effects of the classical GABAA receptor competitive antagonist bicuculline and noncompetitive antagonist picrotoxinin. Bilobalide (IC50 = 4.6F0.5 AM) was almost as potent as bicuculline and pictrotoxinin (IC50 = 2.0F0.1 and 2.4F0.5 AM, respectively) at a1h2g2L GABAA receptors against 40 AM GABA (GABA EC50). While bilobalide and picrotoxinin were clearly noncompetitive antagonists, the potency of bilobalide decreased at high GABA concentrations suggesting a component of competitive antagonism.

http://www.columbia.edu/
Ginkgo biloba, the ginkgo tree, is the oldest living tree, with a long history of use in traditional Chinese medicine. In recent years, the leaf extracts have been widely sold as phytomedicine in Europe and as a dietary supplement worldwide. Effects of Ginkgo biloba extracts have been postulated to include improvement of memory, increased blood circulation, as well as beneficial effects to sufferers of Alzheimer's disease. The most unique components of the extracts are the terpene trilactones, that is, ginkgolides and bilobalide. These structurally complex molecules have been attractive targets for total synthesis. Terpene trilactones are believed to be partly responsible for the neuromodulatory properties of Ginkgo biloba extracts, and several biological effects of the terpene trilactones have been discovered in recent years, making them attractive pharmacological tools that could provide insight into the effects of Ginkgo biloba extracts.

Local
Ginkgo biloba extract contain specific terpenoids called ginkgolides (ginkgolide A, ginkgolide B, ginkgolide C - diterpenes) and bilobalide (pentanorditerpene). Ginkgolide A (GA) and ginkgolide B (GB) are the main molecular forms of ginkgolides. These compounds are non-competitive antagonists of the GABAA and glycine receptors, and are structurally related to picrotoxin (PTX), also a non-competitive antagonist of these receptors. These compounds are thought to bind in the channel of these receptors.
The medical benefits of GINKGO BILOBA EXTRACT rely primarily on two groups of active components: the ginkgo flavone glycosides and the terpene lactones. The ginkgo flavone glycoside designation on GBE labels indicates the carefully measured balance of bioflavonoids. These bioflavonoids are primarily responsible for GBE's antioxidant activity and ability to inhibit platelet aggregation. These two actions may help GBE prevent circulatory diseases such as atherosclerosis and support the brain and central nervous system. The unique terpene lactone components found in GBE, known as ginkgolides and bilobalide typically make up 6% of the extract. They are associated with increased circulation to the brain and other parts of the body as well as exert a protective action on nerve cells. Ginkgolides may improve circulation and inhibit platelet-activating factor. Bilobalide is known to protect the cells of the nervous system.

 

SALES SPECIFICATION

APPEARANCE

white to off-white powder

ASSAY

98.0% min

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not regulated

HAZARD SYMBOL

 
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

Not known

GHS

 

SIGNAL WORD

 

PICTOGRAMS

 

HAZARD STATEMENTS

 

P STATEMENTS

 

EC DIRECTIVES

 

HAZARD CODES

 

RISK PHRASES

36/37/38

SAFETY PHRASES

22-24/25

 

PACKING

 

 

PRICE INFORMATION