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Merck
CN

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:
33570-04-6
Molecular Weight:
326.30
NACRES:
NA.28
PubChem Substance ID:
24892116
UNSPSC Code:
85151701
MDL number:
MFCD00238547

Key Documents

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Product Name

(−)-Bilobalide from Ginkgo biloba leaves, ≥93% (HPLC)

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

SMILES string

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

InChI key

MOLPUWBMSBJXER-YDGSQGCISA-N

biological source

plant leaves (Ginkgo biloba)

assay

≥93% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white

storage temp.

−20°C

Quality Level

100

Related Categories

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.

General description

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT2415
MKCD7001
MKBV8377V
MKBR7959V
SLBH4004V

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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)
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)
Protective and therapeutic role of Bilobalide in cuprizone-induced demyelination
Sui RX, et al.
International Immunopharmacology, 66, 69-81 (2019)
Flaubert Tchantchou et al.
Journal of Alzheimer's disease : JAD, 18(4), 787-798 (2009-08-08)
Loss of synapses has been correlated with dementia in Alzheimer's disease (AD) as an early event during the disease progression. Hence, synaptogenesis and neurogenesis in adulthood could serve as a therapeutic target for the prevention and treatment of AD. Recently
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