Ginkgolide C

Names

[ Name ]:
Ginkgolide C

[Synonym ]:
Ginkgolid C
MFCD02094178
(1R,3R,7S,8S,9R,10S,11R,13S,16S,17R)-8-tert-Butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0.0.0.0]nonadecane-5,15,18-trione
(1R,3R,7S,8S,9R,10S,11R,13S,16S,17R)-6,9,12,17-Tetrahydroxy-16-methyl-8-(2-methyl-2-propanyl)-2,4,14,19-tetraoxahexacyclo[8.7.2.0.0.0.0]nonadecane-5,15,18-trione
6H-9,4a-(Epoxymethano)-3aH,9H-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-2,6,13(1H)-trione, 11-(1,1-dimethylethyl)hexahydro-1,4b,8,10-tetrahydroxy-5-methyl-, (3aR,4aR,4bR,5S,7aS,8aR,9S,10R,11S,11aS)-
1,7-DIHYDROXY-GINKGOLIDE A
Gingkolide C
1,3,7,10-Tetrahydroxyginkgolid
GinkgolideC

Biological Activity

[Description]:

Ginkgolide C is a flavone isolated from Ginkgo biloba leaves, possessing multiple biological functions, such as decreasing platelet aggregation and ameliorating Alzheimer disease.

[Related Catalog]:

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

Natural Products >> Terpenoids and Glycosides

[Target]

AMPK

MMP-9

Sirtuin

[In Vitro]

Ginkgolide C (3-100 μM) has no significant effect on 3T3-L1 cell viability, but suppresses adipogenesis in 3T3-L1 cells followling 24 h treatment. Ginkgolide C (10-100 μM) significantly suppresses lipid accumulation compared with the control group and also significantly promotes glycerol release in 3T3-L1 adipocytes. Ginkgolide C suppresses PPAR-α and PPAR-γ expression and decreases C/EBPα, C/EBPβ, and SREBP-1c expression in differentiated 3T3-L1 adipocytes. In addition, Ginkgolide C (3-100 μM) suppress adipogenesis-related protein (FAS, LPL, and aP2) and mRNA expression in a dose-dependent manner in differentiated 3T3-L1 adipocytes. Ginkgolide C (3-100 μM) also significantly promotes Sirt1 production and increases phosphorylation of AMPKα and ACC-1 in a concentration-dependent manner[1]. Ginkgolide C (1, 10, 50, 100, 500 mM) significantly reduces the collagen (10 mg/mL)-stimulated rat platelet aggregation in a dose-dependent manner. Ginkgolide C (50, 100 mM) causes pro-MMP-9 (92-kDa) to form an activated MMP-9 (86-kDa) in collagen-stimulated platelets[2].

[Cell Assay]

3T3-L1 cells are treated with various concentrations of ginkgolide C in 96-well plates for 24 h. Cell viability is analyzed by the MTT assay. The culture medium is removed, and the cells are incubated with 100 μL MTT solution (5 mg/mL) for 4 h at 37°C. After plates are washed, isopropanol is added to dissolve formazone crystals, followed by absorbance detection with a spectrophotometer at 570 nm[1].

[References]

[1]. Liou CJ, et al. Ginkgolide C Suppresses Adipogenesis in 3T3-L1 Adipocytes via the AMPK Signaling Pathway. Evid Based Complement Alternat Med. 2015;2015:298635.

[2]. Ginkgolide C, et al. Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9. Biol Pharm Bull. 2007 Dec;30(12):2340-4.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
813.8±65.0 °C at 760 mmHg

[ Melting Point ]:
>3000ºC

[ Molecular Formula ]:
C₂₀H₂₄O₁₁

[ Molecular Weight ]:
440.398

[ Flash Point ]:
291.4±27.8 °C

[ Exact Mass ]:
440.131866

[ PSA ]:
169.05000

[ LogP ]:
0.16

[ Vapour Pressure ]:
0.0±6.6 mmHg at 25°C

[ Index of Refraction ]:
1.671

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Mechanistic evaluation of Ginkgo biloba leaf extract-induced genotoxicity in L5178Y cells.

Toxicol. Sci. 139(2) , 338-49, (2014)

Ginkgo biloba has been used for many thousand years as a traditional herbal remedy and its extract has been consumed for many decades as a dietary supplement. Ginkgo biloba leaf extract is a complex m...