(-)-Bilobalide

Names

[ Name ]:
(-)-Bilobalide

[Synonym ]:
()-Bilobalide
(5aR,8R,8aS,9R,10aS)-9-tert-Butyl-8,9-dihydroxydihydro-9H-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-2,4,7(3H,8H)-trione
BILOBALIDE
MFCD00210481
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)dihydro-8,9-dihydroxy-, (3aS,5aR,8R,8aS,9R,10aS)-
(−)-Bilobalide from Ginkgo biloba leaves
(−)-Bilobalide
(-)-Bilobalide from Ginkgo biloba leaves
(3aS,5aR,8R,8aS,9R,10aS)-8,9-Dihydroxy-9-(2-methyl-2-propanyl)dihydro-9H-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-2,4,7(3H,8H)-trione

Biological Activity

[Description]:

Bilobalide is a biologically active terpenic trilactone present in Ginkgo biloba. An increasing number of studies have demonstrated its neuroprotective effects.IC50 Value: 3.33 (pIC50 Value) [1]Target: neuroprotectivein vitro: Inhibition by BB and GB was abolished in mutant receptors containing T6'S and S12'A substitutions, but their potencies were enhanced (42- and 125-fold, respectively) in S2'A mutant receptors [1]. BB enhanced the secretion of α-secretase-cleaved soluble amyloid precursor protein (sAPPα, a by-product of non-amyloidogenic processing of APP) and decreased the β amyloid protein (Aβ, a by-product of amyloidogenic processing of APP) via PI3K-dependent pathway [2].in vivo: Oral administration of bilobalide (10-30 mg/kg) significantly inhibited thermal hyperalgesia in response to carrageenan, capsaicin and paw incision, independent of dose, with an efficacy similar to that of diclofenac. In the carrageenan model, mechanical hypersensitivity and paw oedema were also significantly reduced after treatment with bilobalide (10-30 mg/kg) [3]. BB(4 and 8 mg/kg) significantly protected VD rats against cognitive deficits in the Morris water maze. Biochemical assessment showed that BB (4 and 8 mg/kg) increased superoxide dismutase (SOD) activity and glutathione (GSH) content, and decreased nitric oxide synthase (NOS) activity and malondialdehyde (MDA) content [4].Clinical trial: N/A

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Natural Products >> Terpenoids and Glycosides

Research Areas >> Neurological Disease

[References]

[1]. Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor. Mol Pharmacol. 2011 Jul;80(1):183-90.

[2]. Shi C, Wu F, Xu J, Bilobalide regulates soluble amyloid precursor protein release via phosphatidyl inositol 3 kinase-dependent pathway. Neurochem Int. 2011 Aug;59(1):59-64.

[3]. Goldie M, Dolan S. Bilobalide, a unique constituent of Ginkgo biloba, inhibits inflammatory pain in rats. Behav Pharmacol. 2013 Aug;24(4):298-306.

[4]. Li WZ, Wu WY, Huang H, Protective effect of bilobalide on learning and memory impairment in rats with vascular dementia. Mol Med Rep. 2013 Sep;8(3):935-41.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
651.7±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₁₈O₈

[ Molecular Weight ]:
326.299

[ Flash Point ]:
247.5±25.0 °C

[ Exact Mass ]:
326.100159

[ PSA ]:
119.36000

[ LogP ]:
-0.45

[ Vapour Pressure ]:
0.0±4.4 mmHg at 25°C

[ Index of Refraction ]:
1.606

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LV1665000

Articles

Bilobalide attenuates hypoxia induced oxidative stress, inflammation, and mitochondrial dysfunctions in 3T3-L1 adipocytes via its antioxidant potential.

Free Radic. Res. 48(10) , 1206-17, (2014)

Excessive expansion of white adipose tissue leads to hypoxia which is considered as a key factor responsible for adipose tissue dysfunction in obesity. Hypoxia induces inflammation, insulin resistance...

Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba.

Magn. Reson. Chem. 50(8) , 569-75, (2012)

The complete and unambiguous (1)H NMR assignments of ten marker constituents of Ginkgo biloba are described. The comprehensive (1)H NMR profiles (fingerprints) of ginkgolide A, ginkgolide B, ginkgolid...

Mechanistic evaluation of Ginkgo biloba leaf extract-induced genotoxicity in L5178Y cells.

Toxicol. Sci. 139(2) , 338-49, (2014)

Ginkgo biloba has been used for many thousand years as a traditional herbal remedy and its extract has been consumed for many decades as a dietary supplement. Ginkgo biloba leaf extract is a complex m...