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Ginkgolide B

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Ginkgolide B Basic information

Product Name:
Ginkgolide B
Synonyms:
  • BN 52021
  • GINKGOLIDE B
  • ginkgolide B from ginkgo leaves
  • (1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11R,11aR)-3-(1,1-Dimethylethyl)hexahydro-4,7b,11-trihydroxy-8-methyl-9H-1,7a-(epoxymethano)-1H,6aH-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-5,9,12(4H)-trione
  • ginkgolide b from ginkgo biloba leaves
  • GinkgolideA,1-hydroxy-, (1β)-
  • Ginkgolide B, froM Ginkgo biloba
  • BGinkgolid
CAS:
15291-77-7
MF:
C20H24O10
MW:
424.4
EINECS:
604-876-0
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Inhibitors
  • Saponins
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • PAF receptor
Mol File:
15291-77-7.mol
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Ginkgolide B Chemical Properties

Melting point:
280°C (dec.)
alpha 
D24 -52.6° (c = 1 in ethanol)
Boiling point:
762.4±60.0 °C(Predicted)
Density 
1?+-.0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 10 mg/ml).
pka
pKa1 7.14; pKa2 8.60; pKa3 11.89(at 25℃)
form 
neat
color 
White
Water Solubility 
Soluble in DMSO. Slightly soluble in water and ethanol
BRN 
4727611
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months
InChIKey
SQOJOAFXDQDRGF-MMQTXUMRSA-N
LogP
2.070 (est)
CAS DataBase Reference
15291-77-7(CAS DataBase Reference)
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Safety Information

Safety Statements 
24/25
WGK Germany 
3
10-21
HS Code 
29322090

MSDS

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Ginkgolide B Usage And Synthesis

Description

Ginkgo biloba is a perennial tree belonging to Ginkgoaceae (Ginkgo biloba L., Yin Xing). Its seeds, also known as ginkgo, have a long history of application in traditional medicine for its medicinal value. With promoting blood circulation by removing blood stasis, Ginkgo biloba has a long history of its application in traditional Chinese medicine
In recent years, it has been widely used in the treatment of cerebral ischemic diseases. After further study, it was found that the effective component is ginkgolide compound, which laid the foundation for the development of small molecule drugs.

Chemical Properties

White Crystalline Solid

Physical properties

Appearance: ginkgolide B is a white powder. Solubility: weighed 0.98?g and dissolves in 1L water (calculation). Melting point: the compound melts at 280? °C (calculation)

History

The leaf of Ginkgo biloba is sweet, bitter, astringent, and mild. With activating blood circulation to remove blood stasis, dredging collaterals, relieving pain, and asthma, it is applied for treating blood stasis, chest pain, stroke, lung deficiency cough, and hyperlipidemia.
As early as in the 1930s, scientists began to study ginkgo and harvest a variety of ginkgolide . Ginkgolide B was isolated and its structure illustrated by Wan Shan et?al. in 1967. Subsequently, it was synthesized by Corey et?al. in 1988. The preparation of effective components of Ginkgo biloba has been listed at home and abroad with development.
The Ginkgo biloba extract consisting of ticlopidine is widely used in overseas market for the treatment of cerebral infarction. Intravenous injection of ginkgolide B is applied for the treatment of inflammation, but the project has been in the state, and there is no progress in it for many years. In addition, whether other extract of Ginkgo biloba can be used for the treatment of stable angina, cognitive impairment is still in preclinical research status.

Uses

Family of bioactive terpenes treating cardiovascular and cerebrovascular diseases. Specific platelet activating factor (PAF) antagonists

Uses

Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Uses

Ginkgolide B is used as a potent PAF-R antagonist. Ginkgolide B speeds up PAF hydrolysis by promoting PAF-AH I α2 homodimer activity. Additionally, this compound has been reported to inhibit neutrophil degranulation in vitro. Inhibits superoxide production in vitro and inhibits bronchoconstriction and is neuroprotective following oral administration in vivo.

Indications

The injection consists of multiple components, and there are three kinds of substance mainly in diterpene ginkgolides meglumine injection. It promotes blood circulation by removing blood stasis and activates the channels and collaterals for cerebral ischemia treatment.

Biological Activity

Platelet-activating factor (PAF) receptor antagonist (K i = 1.3 μ M). Inhibits neutrophil degranulation and superoxide production in vitro and inhibits bronchoconstriction and is neuroprotective following oral administration in vivo .

Pharmacology

Ginkgolide B has a variety of pharmacological effects, mainly in cardiovascular and cerebrovascular protection and neuroprotection. On the one hand, with the strongest activity in nature, the platelet-activating factor (PAF) receptor antagonist is recognized by the public . PAF can inhibit the downstream inflammatory cascade for anti-inflammatory. It also can alleviate cerebral infraction volume and cerebral edema induced by cerebral ischemia among the animal model of cerebral ischemia reperfusion through unknown mechanism. By inhibiting NF-κB and TNF-α, the apoptosis of nerve cell can be alleviated. The compound protects the abdominal cavity and intestinal tract by inhibiting release of neutrophil chemotactic protein by macrophage.

Clinical Use

Oral and injection preparations are applied widely in clinical therapy. Made in oral preparation, flavonoids are the main component of raw material. There are little chemical compounds in injection, and ginkgolides are the main component whose content is different from each other. Listed ginkgolide injection is applied for ischemia stroke formed by blood stasis with promoting blood circulation by removing blood stasis and clearing and activating the channels and collaterals. Compared with Shuxuening injection in clinical trials, ginkgolides injection is consistent in improving indicators effect, such as protection in nerve injury and others.

target

p38MAPK | IkB | Syk | Calcium Channel | LDL | Nrf2 | Akt | JNK | MMP(e.g.TIMP) | Caspase | NF-kB | TNF-α | NOS | p53 | Bcl-2/Bax | IKK

References

1) Foldes-Filep et al. (1987), Inhibition by BN 52021 (ginkgolide B) of the binding of [3H]-platelet-activating factor to human neutrophil granulocytes; Biochem. Biophys. Res. Commun., 148 1412 2) Desquand et al. (1986), Interference of BN 52021 (ginkgolide B) with the bronchopulmonary effects of PAF-acether in the guinea-pig; Eur. J. Pharmacol., 127 83 3) Maclennan et al. (2002), The CNS effects of Ginko biloba extracts and ginkgolide B; Prog. Neurobiol., 67 235 4) Li et al. (2013), Neuroprotective effect of ginkogolide B on bupivacaine-induced apoptosis in SH-SY5Y cells; Oxid. Med. Cell. Longev., 2013 159864 5) Wang et al. (2014), Neuroprotection against permanent focal cerebral ischemia by ginkgolides A and B is associated with obstruction of the mitochondrial apoptotic pathway via inhibition of c-Jun N-terminal kinase in rats; J. Neurosci. Res., 92 232

Ginkgolide BSupplier

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