Bilobalide

Bilobalide Property

Melting point:

>300°

alpha 

57820 -64.3° (c = 2 in acetone)

Boiling point:

651.7±55.0 °C(Predicted)

Density 

1.56±0.1 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

Acetone (Slightly), Methanol (Slightly)

pka

11.74±0.40(Predicted)

form 

Solid

color 

White to Off-White

biological source

plant leaves (Ginkgo biloba)

Merck 

14,1220

Stability:

Hygroscopic

InChI

InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8-,11-,13-,14+,15+/m0/s1

InChIKey

MOLPUWBMSBJXER-YDGSQGCISA-N

SMILES

O1C(=O)[C@]23CC(=O)O[C@@]2([H])C[C@](C(C)(C)C)(O)[C@]23[C@@H](O)C(=O)O[C@@]12[H]

LogP

-0.450 (est)

CAS DataBase Reference

33570-04-6(CAS DataBase Reference)

Safety

Safety Statements 

24/25

WGK Germany 

3

RTECS 

LV1665000

F 

10

HS Code 

29322090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

Bilobalide Chemical Properties,Usage,Production

Description

Bilobalide is a sesquiterpene lactone which is found in extracts of G. biloba. It has been shown to protect against cerebral edema, decrease cortical infarct volume, and reduce cerebral ischemic damage. Bilobalide, at 10 μM, reduces the release of glycine and glutamate from hippocampal slices under ischemic conditions. It also activates the rat constitutive androstane receptor at 100 μM and increases the levels and activities of several cytochrome P450 isoforms in rat liver microsomes.

Chemical Properties

Derived from the dried leaves of Ginkgo biloba L.

Uses

Bilobalide provides protection against learning and memory impairment by reducing free radical injury and inhibiting neuronal apoptosis in the brain cortex and hippocampal CA1 region in induced vascular dementia rats.

Uses

Reference Standard in the analysis of herbal medicinal products

Definition

ChEBI: A terpenoid trilactone found in extracts of Ginkgo biloba.

General Description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Enzyme inhibitor

This plant natural product (FW = 326.30 g/mol; CAS 33570-04-6) from the gingko tree (Ginkgo biloba) is a terpene trilactone that exhibits anticonvulsant properties. Bilobalide has multiple mechanisms of action (e.g., acting as a GABAA receptor antagonist (/1), preserving mitochondrial ATP synthesis, inhibiting staurosporine-induced apoptotic damage, suppressing hypoxia-induced membrane deterioration in the brain, and increasing the expression the mitochondrial DNA-encoded COX III subunit of cytochrome c oxidase and the ND1 subunit of NADH dehydrogenase). Bilobalide was later synthesized in E. J. Corey’s laboratory in the late 1980s.

References

[1] DEFEUDIS F V. BILOBALIDE AND NEUROPROTECTION[J]. Pharmacological research, 2002, 46 6: Pages 565-568. DOI: 10.1016/s1043-6618(02)00233-5
[2] CORNELIA KIEWERT . Role of glycine receptors and glycine release for the neuroprotective activity of bilobalide[J]. Brain Research, 2008, 1201: Pages 143-150. DOI: 10.1016/j.brainres.2008.01.052
[3] DOROTHEE LANG . Neuroprotective effects of bilobalide are accompanied by a reduction of ischemia-induced glutamate release in vivo[J]. Brain Research, 2011, 1425: Pages 155-163. DOI: 10.1016/j.brainres.2011.10.005
[4] AIK JIANG LAU. Species-dependent and receptor-selective action of bilobalide on the function of constitutive androstane receptor and pregnane X receptor.[J]. Drug Metabolism and Disposition, 2012, 40 1: 178-186. DOI: 10.1124/dmd.111.042879
[5] Y DENG. Induction of cytochrome P450s by terpene trilactones and flavonoids of the Ginkgo biloba extract EGb 761 in rats.[J]. Xenobiotica, 2008, 38 5: 465-481. DOI: 10.1080/00498250701883233