33570-04-6 Usage
Description
Bilobalide is a sesquiterpene lactone derived from the extracts of Ginkgo biloba, a tree native to China. It has been recognized for its neuroprotective properties and is known to protect against cerebral edema, decrease cortical infarct volume, and reduce cerebral ischemic damage. Bilobalide also exhibits the ability to reduce the release of glycine and glutamate from hippocampal slices under ischemic conditions and activate the rat constitutive androstane receptor, increasing the levels and activities of several cytochrome P450 isoforms in rat liver microsomes.
Uses
Used in Pharmaceutical Industry:
Bilobalide is used as a reference standard in the analysis of herbal medicinal products, particularly those containing Ginkgo biloba extracts. Its presence in these products is essential for ensuring their quality, efficacy, and safety.
Used in Neuroprotection:
Bilobalide is used as a neuroprotective agent for protecting against learning and memory impairment. It achieves this by reducing free radical injury and inhibiting neuronal apoptosis in the brain cortex and hippocampal CA1 region in induced vascular dementia rats.
Used in Cerebral Edema Treatment:
Bilobalide is used as a therapeutic agent for treating cerebral edema, a condition characterized by an excessive accumulation of fluid in the brain, which can lead to increased intracranial pressure and potential brain damage.
Used in Cerebral Ischemic Damage Reduction:
Bilobalide is used as a treatment to decrease cortical infarct volume and reduce cerebral ischemic damage, which can result from a lack of blood flow to the brain due to various causes, such as stroke or other vascular events.
Used in Neurotransmitter Release Regulation:
Bilobalide is used as a regulator of neurotransmitter release, specifically reducing the release of glycine and glutamate from hippocampal slices under ischemic conditions. This regulation can help maintain the balance of neurotransmitters in the brain and potentially improve cognitive function.
Used in Cytochrome P450 Activation:
Bilobalide is used as an activator of the rat constitutive androstane receptor at 100 μM, which in turn increases the levels and activities of several cytochrome P450 isoforms in rat liver microsomes. This activation can have implications for drug metabolism and detoxification processes in the body.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 33570-04-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,5,7 and 0 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 33570-04:
(7*3)+(6*3)+(5*5)+(4*7)+(3*0)+(2*0)+(1*4)=96
96 % 10 = 6
So 33570-04-6 is a valid CAS Registry Number.
InChI:InChI=1/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
33570-04-6Relevant articles and documents
Concise asymmetric synthesis of (?)-bilobalide
Baker, Meghan A.,Demoret, Robert M.,Ohtawa, Masaki,Shenvi, Ryan A.
, p. 643 - 646 (2019)
The Ginkgo biloba metabolite bilobalide is widely ingested by humans but its effect on the mammalian central nervous system is not fully understood1–4. Antagonism of γ-aminobutyric acid A receptors (GABAARs) by bilobalide has been linked to the rescue of cognitive deficits in mouse models of Down syndrome5. A lack of convulsant activity coupled with neuroprotective effects have led some to postulate an alternative, unidentified target4; however, steric congestion and the instability of bilobalide1,2,6 have prevented pull-down of biological targets other than the GABAΑRs. A concise and flexible synthesis of bilobalide would facilitate the development of probes for the identification of potential new targets, analogues with differential selectivity between insect and human GABAΑRs, and stabilized analogues with an enhanced serum half-life7. Here we exploit the unusual reactivity of bilobalide to enable a late-stage deep oxidation that symmetrizes the molecular core and enables oxidation states to be embedded in the starting materials. The same overall strategy may be applicable to G. biloba congeners, including the ginkgolides—some of which are glycine-receptor-selective antagonists8. A chemical synthesis of bilobalide should facilitate the investigation of its biological effects and its therapeutic potential.
Separation Of Ginkgolides And Bilobalide From G. Biloba
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Page/Page column 7, (2008/12/04)
The subject invention provides a method for separating a terpene trilactone from Ginkgo biloba plant material or from an extract of Ginkgo biloba comprising a mixture of terpene trilactones, the process comprising the steps of: a) subjecting the Ginkgo biloba plant material or the extract to column chromatography with an appropriate solvent system to produce at least a first fraction containing the terpene trilactone bilobalide, a second fraction eluted after the first fraction containing the terpene trilactones GA and GB, and a third fraction eluted after the second fraction containing at least a preponderance of the terpene trilactones GC and GJ; and b) alkylating the terpene trilactone GB of the second fraction so as to produce a first mixture including terpene trilactone GA and alkylated terpene trilactone GB; or alkylating the terpene trilactone GC of the third fraction so as produce a second mixture including terpene trilactone GJ and alkylated terpene trilactone GC, so as to thereby isolate a terpene trilactone.
Chemistry of Ginkgolides, III. - Bilobalide/iso-Bilobalide - Structure Determination by X-ray Analysis
Weinges, Klaus,Hepp, Michael,Huber-Patz, Ursula,Irngartinger, Hermann
, p. 1079 - 1086 (2007/10/02)
Bilobalide (1a) shows remarkable biological effects and uncommon chemical properties.Its striking characteristic is the tendency to isomerize under mild acylation conditions to yield the diacyl derivatives 2e-g of the spiro compound 2a.The structures of biobalide (1a) and 10,12-di-O-pivaloyl-iso-bilobalide (2f) are determined by X-ray analysis.
