Ginkgolide B | CAS#15291-77-7 | GlyR agonist | ATP release inhibitor

MedKoo Cat#: 540162 | Name: Ginkgolide B

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Description:

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

Ginkgolide B is a GlyR agonist found in Ginkgo. It inhibits ATP release from thrombin-activated platelets, protects neurons against ischemic injury, prevents edema and inflammation, and increases activation of PKA, Ca+2 signaling, and glutamate release.

Chemical Structure

Ginkgolide B

CAS#15291-77-7

Theoretical Analysis

MedKoo Cat#: 540162

Name: Ginkgolide B

CAS#: 15291-77-7

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
25mg	USD 350.00	2 Weeks
100mg	USD 750.00	2 Weeks

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Related CAS #

No Data

Synonym

Bilobalide B; Ginkgolide B; Ginkolide B; GKB; BN 52021; BN52021; BN-52021; BN 5205; BN52051; BN-52051

IUPAC/Chemical Name

(1R,3R,6R,7S,8S,10R,11R,12S,13S,16S,17R)-8-tert-butyl-6,12,17-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

SQOJOAFXDQDRGF-INETUYANSA-N

InChi Code

InChI=1S/C20H24O10/c1-6-12(23)28-11-9(21)18-8-5-7(16(2,3)4)17(18)10(22)13(24)29-15(17)30-20(18,14(25)27-8)19(6,11)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

O=C(O1)[C@@H](C)[C@@]2(O)[C@]1([H])[C@H](O)C34[C@@]25OC6C3([C@@H](O)C(O6)=O)[C@H](C(C)(C)C)C[C@H]4OC5=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

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: Nabavi SM, Habtemariam S, Daglia M, Braidy N, Loizzo MR, Tundis R, Nabavi SF. Neuroprotective Effects of Ginkgolide B Against Ischemic Stroke: A Review of Current Literature. Curr Top Med Chem. 2015;15(21):2222-32. Review. PubMed PMID: 26059355. 2: Wang GG, Chen QY, Li W, Lu XH, Zhao X. Ginkgolide B increases hydrogen sulfide and protects against endothelial dysfunction in diabetic rats. Croat Med J. 2015 Feb;56(1):4-13. PubMed PMID: 25727037; PubMed Central PMCID: PMC4364347. 3: Liu X, Yan Y, Bao L, Chen B, Zhao Y, Qi R. Ginkgolide B inhibits platelet release by blocking Syk and p38 MAPK phosphorylation in thrombin-stimulated platelets. Thromb Res. 2014 Nov;134(5):1066-73. doi: 10.1016/j.thromres.2014.08.025. Epub 2014 Sep 6. PubMed PMID: 25223809. 4: Liu X, Sun W, Zhao Y, Chen B, Wu W, Bao L, Qi R. Ginkgolide B Inhibits JAM-A, Cx43, and VE-Cadherin Expression and Reduces Monocyte Transmigration in Oxidized LDL-Stimulated Human Umbilical Vein Endothelial Cells. Oxid Med Cell Longev. 2015;2015:907926. doi: 10.1155/2015/907926. Epub 2015 Jul 12. PubMed PMID: 26246869; PubMed Central PMCID: PMC4515296. 5: Lee CM, Jung WK, Na G, Lee DS, Park SG, Seo SK, Yang JW, Yea SS, Lee YM, Park WS, Choi IW. Inhibitory effects of the platelet-activating factor receptor antagonists, CV-3988 and Ginkgolide B, on alkali burn-induced corneal neovascularization. Cutan Ocul Toxicol. 2015 Mar;34(1):53-60. doi: 10.3109/15569527.2014.903573. Epub 2014 Apr 22. PubMed PMID: 24754407. 6: Chi CL, Shen DF, Wang PJ, Li HL, Zhang L. Effect of ginkgolide B on brain metabolism and tissue oxygenation in severe haemorrhagic stroke. Int J Clin Exp Med. 2015 Mar 15;8(3):3522-9. eCollection 2015. PubMed PMID: 26064244; PubMed Central PMCID: PMC4443078. 7: 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. 8: Zhou T, You WT, Ma ZC, Liang QD, Tan HL, Xiao CR, Tang XL, Zhang BL, Wang YG, Gao Y. Ginkgolide B protects human umbilical vein endothelial cells against xenobiotic injuries via PXR activation. Acta Pharmacol Sin. 2016 Feb;37(2):177-86. doi: 10.1038/aps.2015.124. Epub 2016 Jan 18. PubMed PMID: 26775663; PubMed Central PMCID: PMC4753368. 9: Zhao WC, Hou ZH, Zhang Q, Zheng W. Transcellular transport characteristics of huperzine alone or in combination with ginkgolide B across Caco-2 and Madin-Darby canine kidney cell monolayer. Asian Pac J Trop Med. 2014 Nov;7(11):889-94. doi: 10.1016/S1995-7645(14)60155-3. Epub 2014 Oct 22. PubMed PMID: 25441989. 10: Zheng JL, Li BS, Cao XC, Zhuo WK, Zhang G. Alleviation of spinal cord injury by Ginkgolide B via the inhibition of STAT1 expression. Genet Mol Res. 2016 Jun 16;15(2). doi: 10.4238/gmr.15027673. PubMed PMID: 27323179. 11: Wang DL, Peng DY, Tao XH, Cao Y, Chen WD, Liang Y, Xie L, Liu XD. The pharmacokinetics and conversion of the lactone to the carboxylate forms of ginkgolide B in rat plasma. J Asian Nat Prod Res. 2013;15(4):337-43. doi: 10.1080/10286020.2013.764866. Epub 2013 Feb 19. PubMed PMID: 23421864. 12: Qin XF, Lu XJ, Ge JB, Xu HZ, Qin HD, Xu F. Ginkgolide B prevents cathepsin-mediated cell death following cerebral ischemia/reperfusion injury. Neuroreport. 2014 Mar 5;25(4):267-73. doi: 10.1097/WNR.0000000000000096. PubMed PMID: 24264075. 13: Zhao J, Geng T, Wang Q, Si H, Sun X, Guo Q, Li Y, Huang W, Ding G, Xiao W. Pharmacokinetics of Ginkgolide B after Oral Administration of Three Different Ginkgolide B Formulations in Beagle Dogs. Molecules. 2015 Nov 6;20(11):20031-41. doi: 10.3390/molecules201119678. Erratum in: Molecules. 2016;21(6). pii: E759. doi: 10.3390/molecules21060759. PubMed PMID: 26561795. 14: 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. 15: Ma L, Liu X, Zhao Y, Chen B, Li X, Qi R. Ginkgolide B reduces LOX-1 expression by inhibiting Akt phosphorylation and increasing Sirt1 expression in oxidized LDL-stimulated human umbilical vein endothelial cells. PLoS One. 2013 Sep 17;8(9):e74769. doi: 10.1371/journal.pone.0074769. eCollection 2013. PubMed PMID: 24069345; PubMed Central PMCID: PMC3775799. 16: Lu YM, Pan J, Zhang WN, Hui AL, Guo WQ, Huang L, Zhu QJ, Chen Y. Synthesis, in silico and in vivo blood brain barrier permeability of ginkgolide B cinnamate. Fitoterapia. 2015 Oct;106:110-4. doi: 10.1016/j.fitote.2015.08.012. Epub 2015 Aug 29. PubMed PMID: 26327588. 17: Zhang XT, Jiao HY, Suo QL. [Study on the pharmacokinetics of ginkgolide B for injection in rats]. Zhong Yao Cai. 2012 Mar;35(3):430-3. Chinese. PubMed PMID: 22876684. 18: Li XJ, Wang YQ, Yang J, Fan X, Wang L, Yang K, Lan K. Semi-quantitative determination of monocarboxylate forms of ginkgolide B in plasma by UPLC-MS. Anal Bioanal Chem. 2015 May;407(14):4121-9. doi: 10.1007/s00216-015-8628-z. Epub 2015 Mar 31. PubMed PMID: 25822160. 19: Sun L, He Z, Ke J, Li S, Wu X, Lian L, He X, He X, Hu J, Zou Y, Wu X, Lan P. PAF receptor antagonist Ginkgolide B inhibits tumourigenesis and angiogenesis in colitis-associated cancer. Int J Clin Exp Pathol. 2015 Jan 1;8(1):432-40. eCollection 2015. PubMed PMID: 25755731; PubMed Central PMCID: PMC4348885. 20: Zhang XT, Jiao HY, Suo QL. [Study on pharmacokinetics of ginkgolide B injection in Beagle dogs]. Zhong Yao Cai. 2012 May;35(5):762-5. Chinese. PubMed PMID: 23213741.