| Identification | More | [Name]
Ginkgolide B | [CAS]
15291-77-7 | [Synonyms]
7-DEOXYGINKGOLIDE C
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)- | [EINECS(EC#)]
604-876-0 | [Molecular Formula]
C20H24O10 | [MDL Number]
MFCD05662347 | [Molecular Weight]
424.4 | [MOL File]
15291-77-7.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [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. ]
2-8°C
| [solubility ]
Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 10 mg/ml). | [form ]
neat | [pka]
pKa1 7.14; pKa2 8.60; pKa3 11.89(at 25℃) | [color ]
White | [Water Solubility ]
Soluble in DMSO. Slightly soluble in water and ethanol | [Usage]
Family of bioactive terpenes treating cardiovascular and cerebrovascular diseases. Specific platelet activating factor (PAF) antagonists | [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 | [SMILES]
[C@@]12(O)[C@]34C(=O)O[C@@H]5C[C@@H](C(C)(C)C)C6([C@@H](O)C(=O)O[C@@]6([H])O3)C45[C@H](O)[C@]1([H])OC(=O)[C@H]2C | [LogP]
2.070 (est) | [CAS DataBase Reference]
15291-77-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [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 | [storage]
Store at 2-8°C Dry, sealed and protect from light | [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 |
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