| Identification | More | [Name]
Bilobalide | [CAS]
33570-04-6 | [Synonyms]
3',5-DIHYDROXY-3,4',6,7-TETRAMETHOXY FLAVONE
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)-10,10A-DIHYDRO-8,9-DIHYDROXY-, [5AR-(3AS*,5A,8,8AS*,9,10A)]-
5,3'-DIHYDROXY-3,6,7,4'-TETRAMETHOXYFLAVONE
BILOBALID
(-)-BILOBALIDE
BILOBALIDE
CASTICIN
VITEXICARPIM
VITEXICARPIN
(-)-bilobalidefromginkgoleaves
BILOBALIDE: 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)-10,10A-DIHYDRO-8,9-DIHYDROXY-, [5AR-(3AS*,5A,8,8AS*,9,10A)]-,
(-)-bilobalide from ginkgo biloba leaves
BILOBALIDE(AHP)
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)-10,10a-dihydro-8,9-dihydroxy-,[5aR-(3aS*,5aα,8β,8aS*,9α,10aα)]- | [EINECS(EC#)]
608-892-9 | [Molecular Formula]
C19H18O8 | [MDL Number]
MFCD00210481 | [Molecular Weight]
374.34 | [MOL File]
33570-04-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
>300° | [alpha ]
57820 -64.3° (c = 2 in acetone) | [Boiling point ]
651.7±55.0 °C(Predicted) | [density ]
1.56±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Acetone (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
11.74±0.40(Predicted) | [color ]
White to Off-White | [biological source]
plant leaves (Ginkgo biloba) | [Merck ]
14,1220 | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8-,11-,13-,14+,15+/m0/s1 | [InChIKey]
MOLPUWBMSBJXER-YDGSQGCISA-N | [SMILES]
O1C(=O)[C@]23CC(=O)O[C@@]2([H])C[C@](C(C)(C)C)(O)[C@]23[C@@H](O)C(=O)O[C@@]12[H] | [LogP]
-0.450 (est) | [CAS DataBase Reference]
33570-04-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Bilobalide is a sesquiterpene lactone which is found in extracts of G. biloba. It has been shown to protect against cerebral edema, decrease cortical infarct volume, and reduce cerebral ischemic damage.1 Bilobalide, at 10 μM, reduces the release of glycine and glutamate from hippocampal slices under ischemic conditions.2,3 It also activates the rat constitutive androstane receptor at 100 μM and increases the levels and activities of several cytochrome P450 isoforms in rat liver microsomes.4,5 | [Uses]
Reference Standard in the analysis of herbal medicinal products | [Definition]
ChEBI: A terpenoid trilactone found in extracts of Ginkgo biloba. | [General Description]
Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate. | [Enzyme inhibitor]
This plant natural product (FW = 326.30 g/mol; CAS 33570-04-6) from the gingko tree (Ginkgo biloba) is a terpene trilactone that exhibits anticonvulsant properties. Bilobalide has multiple mechanisms of action (e.g., acting as a GABAA receptor antagonist (/1), preserving mitochondrial ATP synthesis, inhibiting staurosporine-induced apoptotic damage, suppressing hypoxia-induced membrane deterioration in the brain, and increasing the expression the mitochondrial DNA-encoded COX III subunit of cytochrome c oxidase and the ND1 subunit of NADH dehydrogenase). Bilobalide was later synthesized in E. J. Corey’s laboratory in the late 1980s. | [storage]
Store at -20°C | [References]
[1] DEFEUDIS F V. BILOBALIDE AND NEUROPROTECTION[J]. Pharmacological research, 2002, 46 6: Pages 565-568. DOI: 10.1016/s1043-6618(02)00233-5
[2] CORNELIA KIEWERT . Role of glycine receptors and glycine release for the neuroprotective activity of bilobalide[J]. Brain Research, 2008, 1201: Pages 143-150. DOI: 10.1016/j.brainres.2008.01.052
[3] DOROTHEE LANG . Neuroprotective effects of bilobalide are accompanied by a reduction of ischemia-induced glutamate release in vivo[J]. Brain Research, 2011, 1425: Pages 155-163. DOI: 10.1016/j.brainres.2011.10.005
[4] AIK JIANG LAU. Species-dependent and receptor-selective action of bilobalide on the function of constitutive androstane receptor and pregnane X receptor.[J]. Drug Metabolism and Disposition, 2012, 40 1: 178-186. DOI: 10.1124/dmd.111.042879
[5] Y DENG. Induction of cytochrome P450s by terpene trilactones and flavonoids of the Ginkgo biloba extract EGb 761 in rats.[J]. Xenobiotica, 2008, 38 5: 465-481. DOI: 10.1080/00498250701883233 |
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