Ginkgolide J | CAS#107438-79-9 | prevents amyloid-β-induced cell death | suppresses superoxide and hydroxyperoxyl radical formation

MedKoo Cat#: 540164 | Name: Ginkgolide J

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ginkgolide J is found in Ginkgo. It prevents amyloid-β-induced cell death and suppresses superoxide and hydroxyperoxyl radical formation.

Chemical Structure

Ginkgolide J

CAS#107438-79-9

Theoretical Analysis

MedKoo Cat#: 540164

Name: Ginkgolide J

CAS#: 107438-79-9

Chemical Formula: C20H24O10

Exact Mass: 424.1369

Molecular Weight: 424.40

Elemental Analysis: C, 56.60; H, 5.70; O, 37.70

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 750.00	2 Weeks
100mg	USD 1,350.00	2 Weeks

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Related CAS #

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Synonym

Ginkgolide J; Ginkgolide-J;7-beta-Hydroxyginkgolide A; 7beta-Hydroxyginkgolide A; BN 52024; BN-52024; BN52024;

IUPAC/Chemical Name

(1R,3R,6R,7S,8S,9R,10S,11S,13S,16S,17R)-8-tert-butyl-6,9,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione

InChi Key

LMEHVEUFNRJAAV-NCRQBLAGSA-N

InChi Code

InChI=1S/C20H24O10/c1-6-12(23)27-7-5-17-11-8(21)9(16(2,3)4)18(17)10(22)13(24)29-15(18)30-20(17,14(25)28-11)19(6,7)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8+,9-,10+,11-,15?,17-,18?,19-,20-/m1/s1

SMILES Code

[H]C1[C@]2([H])OC(=O)[C@@H](C)[C@]2(O)[C@@]34OC5OC(=O)[C@H](O)C56[C@@H]([C@H](O)[C@@H](OC3=O)[C@@]146)C(C)(C)C

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 424.40 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.

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

1: 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. 2: 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. 3: 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. 4: Jaracz S, Malik S, Nakanishi K. Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts. Phytochemistry. 2004 Nov;65(21):2897-902. PubMed PMID: 15501258. 5: Dew TP, Wang G, Williamson G. Urinary excretion of ginkgolide terpene lactones following acute consumption of Ginkgo biloba extract. Biofactors. 2014 Mar-Apr;40(2):268-74. doi: 10.1002/biof.1151. Epub 2013 Nov 20. PubMed PMID: 24255015. 6: Vitolo O, Gong B, Cao Z, Ishii H, Jaracz S, Nakanishi K, Arancio O, Dzyuba SV, Lefort R, Shelanski M. Protection against beta-amyloid induced abnormal synaptic function and cell death by Ginkgolide J. Neurobiol Aging. 2009 Feb;30(2):257-65. Epub 2007 Jul 20. PubMed PMID: 17640772; PubMed Central PMCID: PMC2646106. 7: Scholtyssek H, Damerau W, Wessel R, Schimke I. Antioxidative activity of ginkgolides against superoxide in an aprotic environment. Chem Biol Interact. 1997 Oct 24;106(3):183-90. PubMed PMID: 9413545. 8: Lau AJ, Yang G, Rajaraman G, Baucom CC, Chang TK. Human pregnane X receptor agonism by Ginkgo biloba extract: assessment of the role of individual ginkgolides. J Pharmacol Exp Ther. 2010 Dec;335(3):771-80. doi: 10.1124/jpet.110.172338. Epub 2010 Aug 25. PubMed PMID: 20739453. 9: Jaracz S, Strømgaard K, Nakanishi K. Ginkgolides: selective acetylations, translactonization, and biological evaluation. J Org Chem. 2002 Jun 28;67(13):4623-6. PubMed PMID: 12076171. 10: Kondratskaya EL, Pankratov YV, Lalo UV, Chatterjee SS, Krishtal OA. Inhibition of hippocampal LTP by ginkgolide B is mediated by its blocking action on PAF rather than glycine receptors. Neurochem Int. 2004 Feb;44(3):171-7. PubMed PMID: 14568560. 11: 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. 12: 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. 13: Lau AJ, Yang G, Rajaraman G, Baucom CC, Chang TK. Evaluation of Ginkgo biloba extract as an activator of human glucocorticoid receptor. J Ethnopharmacol. 2013 Jan 30;145(2):670-5. doi: 10.1016/j.jep.2012.11.038. Epub 2012 Dec 5. PubMed PMID: 23220176. 14: Napolitano JG, Lankin DC, Chen SN, Pauli GF. Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba. Magn Reson Chem. 2012 Aug;50(8):569-75. doi: 10.1002/mrc.3829. Epub 2012 Jun 22. PubMed PMID: 22730238; PubMed Central PMCID: PMC3590027. 15: Avula B, Wang YH, Smillie TJ, Khan IA. Column liquid chromatography/electrospray ionization-time of flight-mass spectrometry and ultraperformance column liquid chromatography/mass spectrometry methods for the determination of ginkgolides and bilobalide in the leaves of Ginkgo biloba and dietary supplements. J AOAC Int. 2009 Mar-Apr;92(2):645-52. PubMed PMID: 19485226. 16: Jensen AG, Ndjoko K, Wolfender JL, Hostettmann K, Camponovo F, Soldati F. Liquid chromatography-atmospheric pressure chemical ionisation/mass spectrometry: a rapid and selective method for the quantitative determination of ginkgolides and bilobalide in ginkgo leaf extracts and phytopharmaceuticals. Phytochem Anal. 2002 Jan-Feb;13(1):31-8. PubMed PMID: 11899603. 17: Ahlemeyer B, Möwes A, Krieglstein J. Inhibition of serum deprivation- and staurosporine-induced neuronal apoptosis by Ginkgo biloba extract and some of its constituents. Eur J Pharmacol. 1999 Feb 19;367(2-3):423-30. PubMed PMID: 10079019. 18: Lau AJ, Yang G, Chang TK. Isoform-selective activation of human constitutive androstane receptor by Ginkgo biloba extract: functional analysis of the SV23, SV24, and SV25 splice variants. J Pharmacol Exp Ther. 2011 Nov;339(2):704-15. doi: 10.1124/jpet.111.186130. Epub 2011 Aug 23. PubMed PMID: 21862659. 19: Ahlemeyer B, Krieglstein J. Pharmacological studies supporting the therapeutic use of Ginkgo biloba extract for Alzheimer's disease. Pharmacopsychiatry. 2003 Jun;36 Suppl 1:S8-14. Review. PubMed PMID: 13130383. 20: Croom E, Pace R, Paletti A, Sardone N, Gray D. Single-laboratory validation for the determination of terpene lactones in Ginkgo biloba dietary supplement crude materials and finished products by high-performance liquid chromatography with evaporative light-scattering detection. J AOAC Int. 2007 May-Jun;90(3):647-58. PubMed PMID: 17580616; PubMed Central PMCID: PMC4086663.