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Key Documents

B9031

Sigma-Aldrich

(−)-Bilobalide from Ginkgo biloba leaves

≥93% (HPLC)

Synonym(s):

Bilobalide

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About This Item

Empirical Formula (Hill Notation):
C15H18O8
CAS Number:
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Protective and therapeutic role of Bilobalide in cuprizone-induced demyelination
Sui RX, et al.
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)
Chun Shi et al.
Apoptosis : an international journal on programmed cell death, 15(6), 715-727 (2010-03-25)
Bilobalide, a sesquiterpene trilactone constituent of Ginkgo biloba leaf extracts, has been proposed to exert protective and trophic effects on neurons. However, mechanisms underlying the protective effects of bilobalide remain unclear. Using human SH-SY5Y neuroblastoma cells and primary hippocampal neurons

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