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Merck

B9031

Sigma-Aldrich

(−)-Bilobalide from Ginkgo biloba leaves

≥93% (HPLC)

Sinónimos:

Bilobalide

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About This Item

Fórmula empírica (notación de Hill):
C15H18O8
Número de CAS:
Peso molecular:
326.30
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.28

biological source

plant leaves (Ginkgo biloba)

Quality Level

assay

≥93% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white

storage temp.

−20°C

SMILES string

CC(C)(C)[C@]1(O)CC2OC(=O)C[C@@]23C(=O)OC4OC(=O)[C@H](O)[C@]134

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

InChI key

MOLPUWBMSBJXER-YDGSQGCISA-N

General description

Bilobalide is a biologically active terpenic trilactone (terpenoid) extracted from Ginkgo biloba. It is synthesized from geranylgeranyl pyrophosphate (GGPP).

Application

(-)-Bilobalide from Ginkgo biloba leaves has been used as a reference substance to study the antimicrobial activity of different fractions of G.biloba leaves against a number of Gram-positive and negative bacteria and yeasts.

Biochem/physiol Actions

Bilobalide is an inducer of cytochrome P450 enzymes CYP3A1 and CYP1A2. It exhibits neuroprotective, anti-inflammatory, anti-oxidative and anti-apoptotic properties. Bilobalide, a γ-aminobutyric acid (GABA) AA-rho, 5-hydroxytryptamine type 3 (5-HT(3)) receptor antagonist, may be used to study the function of these receptors in the brain processes such as cognition and memory. It serves as a specific platelet-activating factor receptor antagonist, which helps in the treatment of cardiovascular (Alzheimer′s disease) and cerebrovascular diseases.
Bioactive terpenoid found in Ginkgo biloba.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Protective and therapeutic role of Bilobalide in cuprizone-induced demyelination
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International Immunopharmacology, 66, 69-81 (2019)
Molecular cloning, characterization, and functional analysis of acetyl-CoA C-acetyltransferase and mevalonate kinase genes involved in terpene trilactone biosynthesis from Ginkgo biloba
Chen Q, et al.
Molecules (Basel), 22(1), 74-74 (2017)
Antimicrobial investigation of semipurified fractions of Ginkgo biloba leaves
Mazzanti G, et al.
Journal of Ethnopharmacology, 71(1-2), 83-88 (2000)
Induction of cytochrome P450 3A by the Ginkgo biloba extract and bilobalides in human and rat primary hepatocytes
Zhou SF, et al.
Drug Metabolism Letters, 2(1), 60-66 (2008)
Soo Lim et al.
PloS one, 6(6), e20301-e20301 (2011-06-10)
EGb761, a standardized Ginkgo biloba extract, has antioxidant and antiplatelet aggregation and thus might protect against atherosclerosis. However, molecular and functional properties of EGb761 and its major subcomponents have not been well characterized. We investigated the effect of EGb761 and

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