Bilobalide | CAS#33570-04-6 | Ginkgo Biloba

MedKoo Cat#: 326714 | Name: Bilobalide

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Description:

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

Bilobalide is a biologically active terpenic trilactone present in Ginkgo biloba. Bilobalide is important for producing several of the effects of Gingko biloba extracts. It has neuroprotective effects, as well as effects inducing the liver enzymes CYP3A1 and 1A2, which may be partially responsible for interactions between gingko and other herbal medicines or pharmaceutical drugs. Bilobalide has recently been found to be a negative allosteric modulator at the GABAA and GABAA-rho receptors. Of GABAA, it may possibly be selective for the subunits predominantly implicated in cognitive and memory functioning such as α1.

Chemical Structure

Bilobalide

CAS#33570-04-6

Theoretical Analysis

MedKoo Cat#: 326714

Name: Bilobalide

CAS#: 33570-04-6

Chemical Formula: C15H18O8

Exact Mass: 326.1002

Molecular Weight: 326.30

Elemental Analysis: C, 55.21; H, 5.56; O, 39.23

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 600.00	2 Weeks
100mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

(-)-Bilobalide; Bilobalide; Bilobalid.

IUPAC/Chemical Name

4H,5aH,9H-Furo(2,3-b)furo(3',2':2,3)cyclopenta(1,2-c)furan-2,4,7(3H,8H)-trione, 9-(1,1-dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-, (5aR-(3aS*,5aalpha,8beta,8aS*,9alpha,10aalpha))-

InChi Key

MOLPUWBMSBJXER-YDGSQGCISA-N

InChi Code

InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8-,11-,13-,14+,15+/m0/s1

SMILES Code

O=C(O1)C[C@@]2([C@]1([H])C[C@]3(C(C)(C)C)O)[C@@]34[C@](OC([C@@H]4O)=O)([H])OC2=O

Appearance

Solid powder

Purity

>95% (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, not in water

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bilobalide is a biologically active terpenic trilactone present in Ginkgo biloba.

In vitro activity:

The results showed that LPS stimulation induced the release of proinflammatory cytokines, including TNF-α, IL-6 and IL-1β (Figure 1B-D). However, bilobalide (100, 200 nM) significantly reduced LPS-induced proinflammatory cytokine release, while 50 nM bilobalide treatment had no significant effects (Figure 1B-D). Reference: Am J Transl Res. 2021; 13(4): 2021–2040. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8129331/

In vivo activity:

Herein, this study explored functional and mechanistic effects of BI (bilobalide) treatment in a rodent model of DSS-induced UC. These analyses revealed that BI treatment was sufficient to reduce disease severity, increase colon length, and normalize colon histological characteristics relative to those observed in DSS-treated model mice. Reference: Food Funct. 2021 Jul 21;12(14):6226-6239. https://pubmed.ncbi.nlm.nih.gov/34096560/

	Solvent	mg/mL	mM
Solubility
	DMSO	82.5	252.83
	Ethanol	65.0	199.20

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 326.30 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

Formulation protocol:

1. Qin YR, Ma CQ, Wang DP, Zhang QQ, Liu MR, Zhao HR, Jiang JH, Fang Q. Bilobalide alleviates neuroinflammation and promotes autophagy in Alzheimer's disease by upregulating lincRNA-p21. Am J Transl Res. 2021 Apr 15;13(4):2021-2040. PMID: 34017373; PMCID: PMC8129331. 2. Liu J, Geng Z, Zhang Y, Alharbi SA, Shi Y. Sesquiterpenoid bilobalide inhibits gastric carcinoma cell growth and induces apoptosis both in vitro and in vivo models. J Biochem Mol Toxicol. 2021 May;35(5):e22723. doi: 10.1002/jbt.22723. Epub 2021 Jan 28. PMID: 33511709. 3. Zhang H , Wang Y , Su Y , Fang X , Guo W . The alleviating effect and mechanism of Bilobalide on ulcerative colitis. Food Funct. 2021 Jul 21;12(14):6226-6239. doi: 10.1039/d1fo01266e. Epub 2021 Jun 7. PMID: 34096560. 4. Zhao M, Qin J, Shen W, Wu A. Bilobalide Enhances AMPK Activity to Improve Liver Injury and Metabolic Disorders in STZ-Induced Diabetes in Immature Rats via Regulating HMGB1/TLR4/NF-κB Signaling Pathway. Biomed Res Int. 2021 Apr 17;2021:8835408. doi: 10.1155/2021/8835408. PMID: 33959665; PMCID: PMC8075671.

In vitro protocol:

In vivo protocol:

1. Zhang H , Wang Y , Su Y , Fang X , Guo W . The alleviating effect and mechanism of Bilobalide on ulcerative colitis. Food Funct. 2021 Jul 21;12(14):6226-6239. doi: 10.1039/d1fo01266e. Epub 2021 Jun 7. PMID: 34096560. 2. Zhao M, Qin J, Shen W, Wu A. Bilobalide Enhances AMPK Activity to Improve Liver Injury and Metabolic Disorders in STZ-Induced Diabetes in Immature Rats via Regulating HMGB1/TLR4/NF-κB Signaling Pathway. Biomed Res Int. 2021 Apr 17;2021:8835408. doi: 10.1155/2021/8835408. PMID: 33959665; PMCID: PMC8075671.

1: Qian YX, Kang JC, Luo YK, Zhao JJ, He J, Geng K. A Bilobalide-Producing Endophytic Fungus, Pestalotiopsis uvicola from Medicinal Plant Ginkgo biloba. Curr Microbiol. 2016 May 7. [Epub ahead of print] PubMed PMID: 27155842. 2: Ng CC, Duke RK, Hinton T, Johnston GA. GABAA receptor cysteinyl mutants and the ginkgo terpenoid lactones bilobalide and ginkgolides. Eur J Pharmacol. 2016 Apr 15;777:136-46. doi: 10.1016/j.ejphar.2016.03.007. Epub 2016 Mar 4. PubMed PMID: 26953225. 3: Lu L, Wang S, Fu L, Liu D, Zhu Y, Xu A. Bilobalide protection of normal human melanocytes from hydrogen peroxide-induced oxidative damage via promotion of antioxidase expression and inhibition of endoplasmic reticulum stress. Clin Exp Dermatol. 2016 Jan;41(1):64-73. doi: 10.1111/ced.12664. Epub 2015 Jul 14. PubMed PMID: 26178968. 4: 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. 5: Jiang M, Li J, Peng Q, Liu Y, Liu W, Luo C, Peng J, Li J, Yung KK, Mo Z. Neuroprotective effects of bilobalide on cerebral ischemia and reperfusion injury are associated with inhibition of pro-inflammatory mediator production and down-regulation of JNK1/2 and p38 MAPK activation. J Neuroinflammation. 2014 Sep 26;11:167. doi: 10.1186/s12974-014-0167-6. PubMed PMID: 25256700; PubMed Central PMCID: PMC4189683. 6: 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. 7: Priyanka A, Nisha VM, Anusree SS, Raghu KG. Bilobalide attenuates hypoxia induced oxidative stress, inflammation, and mitochondrial dysfunctions in 3T3-L1 adipocytes via its antioxidant potential. Free Radic Res. 2014 Oct;48(10):1206-17. doi: 10.3109/10715762.2014.945442. PubMed PMID: 25039303. 8: Liu M, Guo J, Wang J, Zhang L, Pang T, Liao H. Bilobalide induces neuronal differentiation of P19 embryonic carcinoma cells via activating Wnt/β-catenin pathway. Cell Mol Neurobiol. 2014 Aug;34(6):913-23. doi: 10.1007/s10571-014-0072-7. Epub 2014 May 18. PubMed PMID: 24838256. 9: Wang J, Ouyang J, Liu Y, Jia X, You S, He X, Di X. Development of a sensitive LC-MS/MS method for the determination of bilobalide in rat plasma with special consideration of ex vivo bilobalide stability: application to a preclinical pharmacokinetic study. J Pharm Biomed Anal. 2014 Jul;95:238-44. doi: 10.1016/j.jpba.2014.03.003. Epub 2014 Mar 12. PubMed PMID: 24704454. 10: Zheng YQ, Liu JX, Xu L, Yao MJ, Song WT. [Study on effect of weinaokang and bilobalide on autophagy and neurogenesis induced by focal cerebral ischemia reperfusion]. Zhongguo Zhong Yao Za Zhi. 2013 Jul;38(13):2182-6. Chinese. PubMed PMID: 24079250. 11: Schwarzkopf TM, Hagl S, Eckert GP, Klein J. Neuroprotection by bilobalide in ischemia: improvement of mitochondrial function. Pharmazie. 2013 Jul;68(7):584-9. PubMed PMID: 23923641. 12: Schwarzkopf TM, Koch KA, Klein J. Neurodegeneration after transient brain ischemia in aged mice: beneficial effects of bilobalide. Brain Res. 2013 Sep 5;1529:178-87. doi: 10.1016/j.brainres.2013.07.003. Epub 2013 Jul 11. PubMed PMID: 23850645. 13: Goldie M, Dolan S. Bilobalide, a unique constituent of Ginkgo biloba, inhibits inflammatory pain in rats. Behav Pharmacol. 2013 Aug;24(4):298-306. doi: 10.1097/FBP.0b013e32836360ab. PubMed PMID: 23838965. 14: Li WZ, Wu WY, Huang H, Wu YY, Yin YY. Protective effect of bilobalide on learning and memory impairment in rats with vascular dementia. Mol Med Rep. 2013 Sep;8(3):935-41. doi: 10.3892/mmr.2013.1573. Epub 2013 Jul 8. PubMed PMID: 23835946. 15: Yin Y, Ren Y, Wu W, Wang Y, Cao M, Zhu Z, Wang M, Li W. Protective effects of bilobalide on Aβ(25-35) induced learning and memory impairments in male rats. Pharmacol Biochem Behav. 2013 May;106:77-84. doi: 10.1016/j.pbb.2013.03.005. Epub 2013 Mar 26. PubMed PMID: 23537729. 16: Ma L, Wang S, Tai F, Yuan G, Wu R, Liu X, Wei B, Yang X. Effects of bilobalide on anxiety, spatial learning, memory and levels of hippocampal glucocorticoid receptors in male Kunming mice. Phytomedicine. 2012 Dec 15;20(1):89-96. doi: 10.1016/j.phymed.2012.09.015. Epub 2012 Oct 17. PubMed PMID: 23083816. 17: Huang M, Qian Y, Guan T, Huang L, Tang X, Li Y. Different neuroprotective responses of Ginkgolide B and bilobalide, the two Ginkgo components, in ischemic rats with hyperglycemia. Eur J Pharmacol. 2012 Feb 29;677(1-3):71-6. doi: 10.1016/j.ejphar.2011.12.011. Epub 2011 Dec 16. PubMed PMID: 22197649. 18: Lang D, Kiewert C, Mdzinarishvili A, Schwarzkopf TM, Sumbria R, Hartmann J, Klein J. Neuroprotective effects of bilobalide are accompanied by a reduction of ischemia-induced glutamate release in vivo. Brain Res. 2011 Nov 24;1425:155-63. doi: 10.1016/j.brainres.2011.10.005. Epub 2011 Oct 6. PubMed PMID: 22032877; PubMed Central PMCID: PMC3217178. 19: Lau AJ, Yang G, Rajaraman G, Baucom CC, Chang TK. Species-dependent and receptor-selective action of bilobalide on the function of constitutive androstane receptor and pregnane X receptor. Drug Metab Dispos. 2012 Jan;40(1):178-86. doi: 10.1124/dmd.111.042879. Epub 2011 Oct 21. PubMed PMID: 22019630. 20: Shi C, Zheng DD, Wu FM, Liu J, Xu J. The phosphatidyl inositol 3 kinase-glycogen synthase kinase 3β pathway mediates bilobalide-induced reduction in amyloid β-peptide. Neurochem Res. 2012 Feb;37(2):298-306. doi: 10.1007/s11064-011-0612-1. Epub 2011 Sep 28. PubMed PMID: 21952928.