Ginkgolide C | CAS:15291-76-6 | Manufacturer ChemFaces

Ginkgolide C

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Description:

Ginkgolide C is a potent inhibitor of collagen-stimulated platelet aggregation, it may increase intracellular cAMP and cGMP production and MMP-9 activity, inhibit intracellular Ca(2+) mobilization and TXA(2) production. Ginkgolide C has anti-adipogenic and ameliorating Alzheimer disease effects; it also can increase△LVP significantly,enhances the myocardial systolic and diastolic function of rats,but has no significant effect on HR while it shows inotropic activity.

Targets:

MMP(e.g.TIMP) | Calcium Channel | cAMP | AMPK | TXA(2)

In vitro:

Evid Based Complement Alternat Med. 2015; 2015: 298635.

Ginkgolide C Suppresses Adipogenesis in 3T3-L1 Adipocytes via the AMPK Signaling Pathway[Pubmed: 26413119]

Ginkgolide C, isolated from Ginkgo biloba leaves, is a flavone reported to have multiple biological functions, from decreased platelet aggregation to ameliorating Alzheimer disease. The study aim was to evaluate the antiadipogenic effect of Ginkgolide C in 3T3-L1 adipocytes.
METHODS AND RESULTS:
Ginkgolide C was used to treat differentiated 3T3-L1 cells. Cell supernatant was collected to assay glycerol release, and cells were lysed to measure protein and gene expression related to adipogenesis and lipolysis by western blot and real-time PCR, respectively. Ginkgolide C significantly suppressed lipid accumulation in differentiated adipocytes. It also decreased adipogenesis-related transcription factor expression, including peroxisome proliferator-activated receptor and CCAAT/enhancer-binding protein. Furthermore, Ginkgolide C enhanced adipose triglyceride lipase and hormone-sensitive lipase production for lipolysis and increased phosphorylation of AMP-activated protein kinase (AMPK), resulting in decreased activity of acetyl-CoA carboxylase for fatty acid synthesis. In coculture with an AMPK inhibitor (compound C), Ginkgolide C also improved activation of sirtuin 1 and phosphorylation of AMPK in differentiated 3T3-L1 cells.
CONCLUSIONS:
The results suggest that Ginkgolide C is an effective flavone for increasing lipolysis and inhibiting adipogenesis in adipocytes through the activated AMPK pathway.

In vivo:

Proceeding of Clinical Medicine, 2013, 22(7):524-6.

Effect of Ginkgolide C in cardiac function of rats in the body.[Reference: WebLink]

To study the effect of Ginkgolide C(GC) in cardiac function of rats in the body.
METHODS AND RESULTS:
: Normal rats after anesthetized,inserted the intubate which connecting the pressure transducer into left ventricular from the right common carotid artery,then detected the cardiac function by the PowerLab biological signal acquisition system.Gave each of saline,1‰dimethyl sulfoxide(DMSO),100 μ mol / L GC,1 000 μ mol / L GC 1ml from the jugular vein,detected the cardiac function before and after administration by continuous recording the left ventricular systolic pressure(LVSP),left ventricular end diastolic pressure(LVEDP),the maximal rate of pressure increase in systole phase(+dp / dtmax),maximal rate of pressure decrease in diastole phase(-dp / dtmax) and heart rate(HR).Compared with normal conditions,when given 100 μ mol / L GC,there are no significant effect on cardiac function;when given 1 000 μ mol / L GC,it showed inotropic activity by increasing △LVP,+dp / dtmax,-dp / dtmax significantly,but had no significant effect on HR.
CONCLUSIONS:
Ginkgolide C can increase△LVP significantly,enhances the myocardial systolic and diastolic function of rats,but has no significant effect on HR while it shows inotropic activity.

Ginkgolide C Description

Source:	The leaves of Ginkgo biloba L.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

Biol Pharm Bull. 2007 Dec;30(12):2340-4.

Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9.[Pubmed: 18057723 ]

METHODS AND RESULTS:
In this report, we investigated the effect of Ginkgolide C (GC) from Ginkgo biloba leaves in collagen (10 mug/ml)-stimulated platelet aggregation. It has been known that matrix metalloproteinase-9 (MMP-9) is released from human platelets, and that it significantly inhibited platelet aggregation stimulated by collagen. Zymographic analysis confirmed that pro-MMP-9 (92-kDa) was activated by GC to form an activated MMP-9 (86-kDa) on gelatinolytic activities. And then, GC dose-dependently inhibited platelet aggregation, intracellular Ca(2+) mobilization, and thromboxane A(2) (TXA(2)) formation in collagen-stimulated platelets. In addition, GC significantly increased the formation of cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP), which have an anti-platelet function in both resting and collagen-stimulated platelets. Therefore, we demonstrate that the inhibitory effect of GC on platelet aggregation might be involved into the following pathways. GC may increase intracellular cAMP and cGMP production and MMP-9 activity, inhibit intracellular Ca(2+) mobilization and TXA(2) production, thereby leading to inhibition of platelet aggregation.
CONCLUSIONS:
These results strongly indicate that GC is a potent inhibitor of collagen-stimulated platelet aggregation. It may be a suitable tool for a negative regulator during platelet activation.

Structure Identification:

Acta Crystallogr C. 2002 Mar;58(Pt 3):o195-8.

Three ginkgolide hydrates from Ginkgo biloba L.: ginkgolide A monohydrate, ginkgolide C sesquihydrate and ginkgolide J dihydrate, all determined at 120 K.[Pubmed: 11870327]

A low-temperature structure of ginkgolide A monohydrate, (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-3-(1,1-dimethylethyl)-hexahydro-4,7b-dihydroxy-8-methyl-9H-1,7a-epoxymethano-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione monohydrate, C(20)H(24)O(9) x H(2)O, obtained from Mo K alpha data, is a factor of three more precise than the previous room-temperature determination.
METHODS AND RESULTS:
A refinement of the ginkgolide A monohydrate structure with Cu K alpha data has allowed the assignment of the absolute configuration of the series of compounds. Ginkgolide C sesquihydrate, (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11S,11aR)-3-(1,1-dimethylethyl)-hexahydro-2,4,7b,11-tetrahydroxy-8-methyl-9H-1,7a-epoxymethano-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione sesquihydrate, C(20)H(24)O(11) x 1.5H(2)O, has two independent diterpene molecules, both of which exhibit intramolecular hydrogen bonding between OH groups. Ginkgolide J dihydrate, (1S,2R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-3-(1,1-dimethylethyl)-hexahydro-2,4,7b-trihydroxy-8-methyl-9H-1,7a-epoxymethano-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione dihydrate, C(20)H(24)O(10) x 2H(2)O, has the same basic skeleton as the other ginkgolides, with its three OH groups having the same configurations as those in Ginkgolide C.
CONCLUSIONS:
The conformations of the six five-membered rings are quite similar across ginkgolides A-C and J, except for the A and F rings of ginkgolide A.

Product Name	Ginkgolide C
Price:	$30 / 20mg
CAS No.:	15291-76-6
Catalog No.:	CFN99639
Molecular Formula:	C₂₀H₂₄O₁₁
Molecular Weight:	440.4 g/mol
Purity:	>=98%
Type of Compound:	Diterpenoids
Physical Desc.:	Powder
Source:	The leaves of Ginkgo biloba L.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Neuroprotection Compound Library Cardioprotective Compound Library Anticoagulants Compound Library Anti-adipogenic Compound Library Diterpenoids Compound Library MMP(e.g.TIMP) Inhibitor Library cAMP Inhibitor Library Calcium Channel Inhibitor Library AMPK Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.2707 mL	11.3533 mL	22.7066 mL	45.4133 mL	56.7666 mL
5 mM	0.4541 mL	2.2707 mL	4.5413 mL	9.0827 mL	11.3533 mL
10 mM	0.2271 mL	1.1353 mL	2.2707 mL	4.5413 mL	5.6767 mL
50 mM	0.0454 mL	0.2271 mL	0.4541 mL	0.9083 mL	1.1353 mL
100 mM	0.0227 mL	0.1135 mL	0.2271 mL	0.4541 mL	0.5677 mL

CFN90670	Rhodojaponin V	37720-86-8	410.5	C₂₂H₃₄O₇
CFN99049	Itol A	1033747-78-2	368.5	C₂₀H₃₂O₆
CFN99638	Ginkgolide A	15291-75-5	408.4	C₂₀H₂₄O₉
CFN99149	Ginkgolide J	107438-79-9	424.40	C₂₀H₂₄O₁₀
CFN99640	Ginkgolide B	15291-77-7	424.4	C₂₀H₂₄O₁₀
CFN99639	Ginkgolide C	15291-76-6	440.4	C₂₀H₂₄O₁₁
CFN91009	Ginkgolide K	153355-70-5	406.4	C₂₀H₂₂O₉
CFN96287	Gopherenediol	916236-79-8	306.5	C₂₀H₃₄O₂
CFN90674	Rhodojaponin II	26116-89-2	410.51	C₂₂H₃₄O₇
CFN90673	Rhodojaponin III	26342-66-5	368.47	C₂₀H₃₂O₆