CAS 33570-04-6|(-)-Bilobalide

Introduction：Basic information about CAS 33570-04-6|(-)-Bilobalide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. (-)-Bilobalide BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles32
6. Synonyms

Common Name	(-)-Bilobalide
CAS Number	33570-04-6	Molecular Weight	326.299
Density	1.6±0.1 g/cm3	Boiling Point	651.7±55.0 °C at 760 mmHg
Molecular Formula	C₁₅H₁₈O₈	Melting Point	/
MSDS	ChineseUSA	Flash Point	247.5±25.0 °C

Names

Name	bilobalide
Synonym	More Synonyms

(-)-Bilobalide BiologicalActivity

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: /
Related Catalog	Signaling Pathways >>Autophagy >>AutophagyNatural Products >>Terpenoids and GlycosidesResearch 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.

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: /

Related Catalog

Signaling Pathways >>Autophagy >>AutophagyNatural Products >>Terpenoids and GlycosidesResearch 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.

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
InChIKey	MOLPUWBMSBJXER-NRSGSQFTSA-N
SMILES	CC(C)(C)C1(O)CC2OC(=O)CC23C(=O)OC2OC(=O)C(O)C231
Storage condition	−20°C

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

Articles32

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...

Synonyms

()-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

Recommended......