B9031
(−)-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
NACRES:
NA.28
PubChem Substance ID:
UNSPSC Code:
85151701
MDL number:
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
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)