Ginkgolide A
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MedKoo CAT#: 540161

CAS#: 15291-75-5

Description: Ginkgolide A is GSK-3β inhibitor and potential PXR agonist found in Ginkgo. It decreases phosphorylation of Tau protein, prevents neointimal hyperplasia and decreases anxiety.

Chemical Structure

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Ginkgolide A
CAS# 15291-75-5
Instruction

Theoretical Analysis

MedKoo Cat#: 540161
Name: Ginkgolide A
CAS#: 15291-75-5
Chemical Formula: C20H24O9
Exact Mass: 408.14
Molecular Weight: 408.400
Elemental Analysis: C, 58.82; H, 5.92; O, 35.26

Price and Availability

Size Price Availability Quantity
5mg USD 215 2 Weeks
10mg USD 350 2 Weeks
25mg USD 555 2 Weeks
50mg USD 790 2 Weeks
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Synonym: Ginkgolide A; BN 52020; BN 52020; BN-52020;

IUPAC/Chemical Name: 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, 3-(1,1-dimethylethyl)hexahydro-4,7b-dihydroxy-8-methyl-, (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-

InChi Key: FPUXKXIZEIDQKW-VKMVSBOZSA-N

InChi Code: InChI=1S/C20H24O9/c1-7-12(22)26-10-6-17-9-5-8(16(2,3)4)18(17)11(21)13(23)28-15(18)29-20(17,14(24)27-9)19(7,10)25/h7-11,15,21,25H,5-6H2,1-4H3/t7-,8+,9-,10+,11+,15+,17-,18+,19-,20-/m1/s1

SMILES Code: C[C@@H]1C(O[C@@H]2[C@@]1(O)[C@@]34C(O[C@H]5[C@@]3([C@]6([C@@H](O)C(O[C@H]6O4)=O)[C@H](C(C)(C)C)C5)C2)=O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 408.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Ma S, Liu X, Xu Q, Zhang X. Transport of ginkgolides with different lipophilicities based on an hCMEC/D3 cell monolayer as a blood-brain barrier cell model. Life Sci. 2014 Oct 2;114(2):93-101. doi: 10.1016/j.lfs.2014.08.006. Epub 2014 Aug 17. PubMed PMID: 25139831.

2: Li J, Li D, Hu J, Bi Y, Xiao W, Wang Z. Simultaneous determination of ginkgolides A, B, C and bilobalide by LC-MS/MS and its application to a pharmacokinetic study in rats. Biomed Chromatogr. 2015 Dec;29(12):1907-12. doi: 10.1002/bmc.3515. Epub 2015 Jul 23. PubMed PMID: 26010697.

3: Zhao Q, Gao C, Cui Z. Ginkgolide A reduces inflammatory response in high-glucose-stimulated human umbilical vein endothelial cells through STAT3-mediated pathway. Int Immunopharmacol. 2015 Apr;25(2):242-8. doi: 10.1016/j.intimp.2015.02.001. Epub 2015 Feb 11. PubMed PMID: 25681539.

4: Huang P, Zhang L, Chai C, Qian XC, Li W, Li JS, Di LQ, Cai BC. Effects of food and gender on the pharmacokinetics of ginkgolides A, B, C and bilobalide in rats after oral dosing with ginkgo terpene lactones extract. J Pharm Biomed Anal. 2014 Nov;100:138-44. doi: 10.1016/j.jpba.2014.07.030. Epub 2014 Aug 2. PubMed PMID: 25165009.

5: Ye N, Wang H, Hong J, Zhang T, Lin C, Meng C. PXR Mediated Protection against Liver Inflammation by Ginkgolide A in Tetrachloromethane Treated Mice. Biomol Ther (Seoul). 2016 Jan;24(1):40-8. doi: 10.4062/biomolther.2015.077. Epub 2016 Jan 1. PubMed PMID: 26759700; PubMed Central PMCID: PMC4703351.

6: Wang X, Jiang CM, Wan HY, Wu JL, Quan WQ, Wu KY, Li D. Neuroprotection against permanent focal cerebral ischemia by ginkgolides A and B is associated with obstruction of the mitochondrial apoptotic pathway via inhibition of c-Jun N-terminal kinase in rats. J Neurosci Res. 2014 Feb;92(2):232-42. doi: 10.1002/jnr.23306. Epub 2013 Nov 4. PubMed PMID: 24327346.

7: Chen Y, Wang C, Hu M, Pan J, Chen J, Duan P, Zhai T, Ding J, Xu C. Effects of ginkgolide A on okadaic acid-induced tau hyperphosphorylation and the PI3K-Akt signaling pathway in N2a cells. Planta Med. 2012 Aug;78(12):1337-41. doi: 10.1055/s-0032-1314965. Epub 2012 Jun 14. PubMed PMID: 22700047.

8: Lau AJ, Yang G, Yap CW, Chang TK. Selective agonism of human pregnane X receptor by individual ginkgolides. Drug Metab Dispos. 2012 Jun;40(6):1113-21. doi: 10.1124/dmd.112.045013. Epub 2012 Mar 5. PubMed PMID: 22393123.

9: Lan K, Li XJ, Du G, Xu L. Characterizations of the hydrolyzed products of ginkgolide A and ginkgolide B by liquid chromatography coupled with mass spectrometry. J Pharm Biomed Anal. 2016 Jan 25;118:113-22. doi: 10.1016/j.jpba.2015.10.029. Epub 2015 Oct 26. PubMed PMID: 26540626.

10: Wang S, Ouyang B, Aa J, Geng J, Fei F, Wang P, Wang J, Peng Y, Geng T, Li Y, Huang W, Wang Z, Xiao W, Wang G. Pharmacokinetics and tissue distribution of ginkgolide A, ginkgolide B, and ginkgolide K after intravenous infusion of ginkgo diterpene lactones in a rat model. J Pharm Biomed Anal. 2016 Jul 15;126:109-16. doi: 10.1016/j.jpba.2016.04.035. Epub 2016 Apr 25. PubMed PMID: 27182682.

11: Jin M, Guo Q, Sun X, Zhang X, Lv Y, Xiao W. [Pharmacokinetics of ginkgolides sustained-release tablet]. Zhongguo Zhong Yao Za Zhi. 2011 Apr;36(8):1011-4. Chinese. PubMed PMID: 21809574.

12: Jensen AA, Bergmann ML, Sander T, Balle T. Ginkgolide X is a potent antagonist of anionic Cys-loop receptors with a unique selectivity profile at glycine receptors. J Biol Chem. 2010 Mar 26;285(13):10141-53. doi: 10.1074/jbc.M109.079319. Epub 2010 Jan 27. PubMed PMID: 20106969; PubMed Central PMCID: PMC2843176.

13: Si HH, Geng T, Sun XP, Zhao J, Xue J. [Absolute bioavailability of ginkgolide compounds in rats]. Zhongguo Zhong Yao Za Zhi. 2015 Jul;40(14):2882-6. Chinese. PubMed PMID: 26666044.

14: Weakley SM, Wang X, Mu H, Lü J, Lin PH, Yao Q, Chen C. Ginkgolide A-gold nanoparticles inhibit vascular smooth muscle proliferation and migration in vitro and reduce neointimal hyperplasia in a mouse model. J Surg Res. 2011 Nov;171(1):31-9. doi: 10.1016/j.jss.2011.03.018. Epub 2011 Apr 1. PubMed PMID: 21571322; PubMed Central PMCID: PMC3161135.

15: Li XJ, Yang K, Du G, Xu L, Lan K. Understanding the regioselective hydrolysis of ginkgolide B under physiological environment based on generation, detection, identification, and semi-quantification of the hydrolyzed products. Anal Bioanal Chem. 2015 Oct;407(26):7945-56. doi: 10.1007/s00216-015-8963-0. Epub 2015 Aug 25. PubMed PMID: 26302962.

16: Zhao J, Muhammad I, Dunbar DC, Khan IA, Fischer NH, Fronczek FR. Three ginkgolide hydrates from Ginkgo biloba L.: ginkgolide A monohydrate, ginkgolide C sesquihydrate and ginkgolide J dihydrate, all determined at 120 K. Acta Crystallogr C. 2002 Mar;58(Pt 3):o195-8. Epub 2002 Feb 28. PubMed PMID: 11870327.

17: He N, Cai HB, Xie HG, Collins X, Edeki TI, Strom SC. Induction of cyp3a in primary cultures of human hepatocytes by ginkgolides a and B. Clin Exp Pharmacol Physiol. 2007 Jul;34(7):632-5. PubMed PMID: 17581220.

18: Rajaraman G, Chen J, Chang TK. Ginkgolide A contributes to the potentiation of acetaminophen toxicity by Ginkgo biloba extract in primary cultures of rat hepatocytes. Toxicol Appl Pharmacol. 2006 Dec 1;217(2):225-33. Epub 2006 Sep 12. PubMed PMID: 17045319.

19: Chang TK, Chen J, Teng XW. Distinct role of bilobalide and ginkgolide A in the modulation of rat CYP2B1 and CYP3A23 gene expression by Ginkgo biloba extract in cultured hepatocytes. Drug Metab Dispos. 2006 Feb;34(2):234-42. Epub 2005 Oct 28. PubMed PMID: 16258077.

20: Ding H, Zhang Z, Cao S, Xu Y, Yu J. Transformation of multi-component ginkgolide into ginkgolide B by Coprinus comatus. BMC Biotechnol. 2015 Mar 14;15:17. doi: 10.1186/s12896-015-0133-0. PubMed PMID: 25887229; PubMed Central PMCID: PMC4372035.