Ginkgolide CCAS# 15291-76-6 |
Quality Control & MSDS
3D structure
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| Cas No. | 15291-76-6 | SDF | Download SDF |
| PubChem ID | 6325205 | Appearance | White powder |
| Formula | C20H24O11 | M.Wt | 440.4 |
| Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
| Synonyms | BN-52022; Ginkgolide-C | ||
| Solubility | DMSO : ≥ 300 mg/mL (681.20 mM) *"≥" means soluble, but saturation unknown. | ||
| SMILES | CC1C(=O)OC2C1(C34C(=O)OC5C3(C2O)C6(C(C5O)C(C)(C)C)C(C(=O)OC6O4)O)O | ||
| Standard InChIKey | AMOGMTLMADGEOQ-WYRVYBOWSA-N | ||
| Standard InChI | InChI=1S/C20H24O11/c1-5-12(24)28-11-8(22)18-10-6(21)7(16(2,3)4)17(18)9(23)13(25)30-15(17)31-20(18,14(26)29-10)19(5,11)27/h5-11,15,21-23,27H,1-4H3/t5-,6-,7?,8?,9?,10-,11+,15+,17?,18?,19-,20-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| 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 | Ginkgolide C Suppresses Adipogenesis in 3T3-L1 Adipocytes via the AMPK Signaling Pathway[Pubmed: 26413119]Evid Based Complement Alternat Med. 2015; 2015: 298635.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. |
| In vivo | Effect of Ginkgolide C in cardiac function of rats in the body.[Reference: WebLink]Proceeding of Clinical Medicine, 2013, 22(7):524-6.To study the effect of Ginkgolide C(GC) in cardiac function of rats in the body. |
| Kinase Assay | Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9.[Pubmed: 18057723 ]Biol Pharm Bull. 2007 Dec;30(12):2340-4.
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| 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. |
Ginkgolide C Dilution Calculator
Ginkgolide C Molarity Calculator
| 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 |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Ginkgolide C is a flavone isolated from Ginkgo biloba leaves, possessing multiple biological functions, such as decreasing platelet aggregation and ameliorating Alzheimer disease.
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].
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.
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Ginkgolide C inhibits platelet aggregation in cAMP- and cGMP-dependent manner by activating MMP-9.[Pubmed:18057723]
Biol Pharm Bull. 2007 Dec;30(12):2340-4.
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. 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.
Ginkgolide C Suppresses Adipogenesis in 3T3-L1 Adipocytes via the AMPK Signaling Pathway.[Pubmed:26413119]
Evid Based Complement Alternat Med. 2015;2015:298635.
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. 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. The results suggest that Ginkgolide C is an effective flavone for increasing lipolysis and inhibiting adipogenesis in adipocytes through the activated AMPK pathway.
Three ginkgolide hydrates from Ginkgo biloba L.: ginkgolide A monohydrate, ginkgolide C sesquihydrate and ginkgolide J dihydrate, all determined at 120 K.[Pubmed:11870327]
Acta Crystallogr C. 2002 Mar;58(Pt 3):o195-8. Epub 2002 Feb 28.
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-dihy droxy-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. 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. 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.
