Ginkgolide B CAS 15291-77-7
Introduction：Basic information about Ginkgolide B CAS 15291-77-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 |
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 | Solid |
| 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 |
| 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) |
Safety Information
| Safety Statements | 24/25 |
| WGK Germany | 3 |
| F | 10-21 |
| HS Code | 29322090 |
| 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] EVA FÜLDES-FILEP Janos F Pierre Braquet. Inhibition by BN 52021 (Ginkgolide B) of the binding of [3h]- Platelet-activating factor to human neutrophil granulocytes[J]. Biochemical and biophysical research communications, 1987, 148 3: Pages 1412-1417. DOI:10.1016/s0006-291x(87)80289-9 [2] STÉPHANIE DESQUAND . Interference of BN 52021 (ginkgolide B) with the bronchopulmonary effects of PAF-acether in the guinea-pig[J]. European journal of pharmacology, 1986, 127 1: Pages 83-95. DOI:10.1016/0014-2999(86)90208-6 [3] KARYN M MACLENNAN Paul F S Cynthia L Darlington. The CNS effects of Ginkgo biloba extracts and ginkgolide B[J]. Progress in Neurobiology, 2002, 67 3: Pages 235-257. DOI:10.1016/s0301-0082(02)00015-1 [4] LE LI. Neuroprotective effect of ginkgolide B on bupivacaine-induced apoptosis in SH-SY5Y cells.[J]. Oxidative Medicine and Cellular Longevity, 2013: 159864. DOI:10.1155/2013/159864 [5] XUAN WANG. 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]. Journal of Neuroscience Research, 2013, 92 2: 232-242. DOI:10.1002/jnr.23306 |
Ginkgolide B Preparation Products And Raw materials
| Raw materials | Ginkgolide C |
