Ginkgolide J

CAS# 107438-79-9

Ginkgolide J

Catalog No. BCN5939----Order now to get a substantial discount!

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Chemical structure

Ginkgolide J

3D structure

Chemical Properties of Ginkgolide J

Cas No. 107438-79-9 SDF Download SDF
PubChem ID 24721483 Appearance White powder
Formula C20H24O10 M.Wt 424.40
Type of Compound Diterpenoids Storage Desiccate at -20°C
Synonyms 7-Hydroxyginkgolide A
Solubility Soluble in methan
Chemical Name (1R,3R,6R,7S,8S,9R,10S,13S,16S,17R)-8-tert-butyl-6,9,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
SMILES CC1C(=O)OC2C1(C34C(=O)OC5C3(C2)C6(C(C5O)C(C)(C)C)C(C(=O)OC6O4)O)O
Standard InChIKey LMEHVEUFNRJAAV-XNSMQBOTSA-N
Standard InChI InChI=1S/C20H24O10/c1-6-12(23)27-7-5-17-11-8(21)9(16(2,3)4)18(17)10(22)13(24)29-15(18)30-20(17,14(25)28-11)19(6,7)26/h6-11,15,21-22,26H,5H2,1-4H3/t6-,7+,8-,9+,10+,11-,15+,17?,18+,19-,20-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Ginkgolide J

The seed of Ginkgo biloba L.

Biological Activity of Ginkgolide J

DescriptionGinkgolide J has neuroprotective activity, it can prevent A beta(1-42) induced inhibition of long-term potentiation in the CA1 region of mouse hippocampal slices, it is also capable of inhibiting cell death of rodent hippocampal neurons caused by A beta(1-42). Ginkgolide J can inhibit platelet aggregation induced by ADP or PAF.
TargetsPDE | Beta Amyloid
In vitro

Protection against beta-amyloid induced abnormal synaptic function and cell death by Ginkgolide J.[Pubmed: 17640772]

Neurobiol Aging. 2009 Feb;30(2):257-65. Epub 2007 Jul 20.


METHODS AND RESULTS:
A new Ginkgo biloba extract P8A (TTL), 70% enriched with terpene trilactones, prevents A beta(1-42) induced inhibition of long-term potentiation in the CA1 region of mouse hippocampal slices. This neuroprotective effect is attributed in large part to Ginkgolide J that completely replicates the effect of the extract. Ginkgolide J is also capable of inhibiting cell death of rodent hippocampal neurons caused by A beta(1-42).
CONCLUSIONS:
This beneficial and multi-faceted mode of action of the ginkgolide makes it a new and promising lead in designing therapies against Alzheimer's disease.

Antioxidative activity of ginkgolides against superoxide in an aprotic environment.[Pubmed: 9413545]

Chem Biol Interact. 1997 Oct 24;106(3):183-90.


METHODS AND RESULTS:
The terpene lactones ginkgolide A, ginkgolide B, ginkgolide C, Ginkgolide J and bilobalide, which are components of a standardized extract (EGb 761) from leaves of Ginkgo biloba, as well as ginkgolide M from roots of G. biloba were studied regarding their reaction against superoxide (O2-) and hydroperoxyl radicals (HO2) in dimethyl sulfoxide as an aprotic solvent. It was found that the ginkgolides B, C, J, M as well as bilobalide react with superoxide and its protonated form as demonstrated by EPR and UV/VIS spectroscopy. The initial reaction rate with these oxygen-derived radicals is in the order of 100 M-1/s and below. Ginkgolide A does not react with superoxide under these conditions.
CONCLUSIONS:
From these findings it can be suggested that the superoxide scavenging effect of the ginkgolides B, C, J, M and bilobalide contributes to the antioxidant properties of G. biloba.

Ginkgolides protect primary cortical neurons from potassium cyanide-induced hypoxic injury.[Pubmed: 17225090 ]

Exp Brain Res. 2007 Jun;179(4):665-71.

In this study, we investigated the effects of ginkgolides (ginkgolide A, ginkgolide B, ginkgolide C and Ginkgolide J), the main constituent of the non-flavone fraction of EGb 761, on hypoxic injury induced by potassium cyanide (KCN) in primary cortical neurons.
METHODS AND RESULTS:
The neurons were pretreated with or without ginkgolides for 24 h before incubation with KCN for 4 h. The results demonstrated that KCN (0.05 mmol/l) significantly decreased cell viability and increased LDH release (P < 0.05 versus the control). The characteristic changes of neuronal morphology induced by KCN were observed. However, pretreatment of neurons with 37.5 microg/ml of ginkgolides (ginkgolides + KCN group) led to a significant increase in cell viability, a decrease in LDH release (P < 0.05 versus the KCN group) and a remarkable improvement in cellular morphology in hypoxic neurons compared with the KCN group.
CONCLUSIONS:
The data suggested that ginkgolides have a significant role to protect the primary cortical neurons from hypoxic injury induced by KCN.

Protocol of Ginkgolide J

Structure Identification
Chinese Journal of Clinicians, 2013,7(24):11569-73.

Effects of the main monomer ingredients of Ginkgo Biloba extract on phosphodiesterase 3 activity of platelet[Pubmed: 15501258]

Ginkgolides A, B, C and J, together with bilobalide, are unique terpenoid components of the Ginkgo biloba tree. Due to similar chemical properties, their separation is quite tedious.
METHODS AND RESULTS:
We have developed an efficient and rapid protocol for separation of individual ginkgolides and bilobalide from G. biloba extracts. The procedure takes advantage of enhanced susceptibility of ginkgolides B and C to benzylation and the ease of separation of these products from ginkgolides A and J which do not react.
CONCLUSIONS:
The protocol is applicable to the previously reported enriched extracts prepared from G. biloba leaves. A single chromatographic step prior to benzylation provides bilobalide and mixture of ginkgolides A, B, C, and J. After benzylation, the individual ginkgolides are separated by chromatography.

Ginkgolide J Dilution Calculator

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Ginkgolide J Molarity Calculator

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Preparing Stock Solutions of Ginkgolide J

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3563 mL 11.7813 mL 23.5627 mL 47.1254 mL 58.9067 mL
5 mM 0.4713 mL 2.3563 mL 4.7125 mL 9.4251 mL 11.7813 mL
10 mM 0.2356 mL 1.1781 mL 2.3563 mL 4.7125 mL 5.8907 mL
50 mM 0.0471 mL 0.2356 mL 0.4713 mL 0.9425 mL 1.1781 mL
100 mM 0.0236 mL 0.1178 mL 0.2356 mL 0.4713 mL 0.5891 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Ginkgolide J

Isolation of ginkgolides A, B, C, J and bilobalide from G. biloba extracts.[Pubmed:15501258]

Phytochemistry. 2004 Nov;65(21):2897-902.

Ginkgolides A, B, C and J, together with bilobalide, are unique terpenoid components of the Ginkgo biloba tree. Due to similar chemical properties, their separation is quite tedious. We have developed an efficient and rapid protocol for separation of individual ginkgolides and bilobalide from G. biloba extracts. The procedure takes advantage of enhanced susceptibility of ginkgolides B and C to benzylation and the ease of separation of these products from ginkgolides A and J which do not react. The protocol is applicable to the previously reported enriched extracts prepared from G. biloba leaves. A single chromatographic step prior to benzylation provides bilobalide and mixture of ginkgolides A, B, C, and J. After benzylation, the individual ginkgolides are separated by chromatography.

Ginkgolides protect primary cortical neurons from potassium cyanide-induced hypoxic injury.[Pubmed:17225090]

Exp Brain Res. 2007 Jun;179(4):665-71.

In this study, we investigated the effects of ginkgolides (Gins A, B, C and J), the main constituent of the non-flavone fraction of EGb 761, on hypoxic injury induced by potassium cyanide (KCN) in primary cortical neurons. The neurons were pretreated with or without ginkgolides for 24 h before incubation with KCN for 4 h. Cell viability was then determined by a MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyletrazolium bromide] assay and lactate dehydrogenase (LDH) release from neurons into the medium was measured. The morphological changes of neurons were observed under inverse microscopy and electron microscopy. The results demonstrated that KCN (0.05 mmol/l) significantly decreased cell viability and increased LDH release (P < 0.05 versus the control). The characteristic changes of neuronal morphology induced by KCN were observed. However, pretreatment of neurons with 37.5 microg/ml of ginkgolides (ginkgolides + KCN group) led to a significant increase in cell viability, a decrease in LDH release (P < 0.05 versus the KCN group) and a remarkable improvement in cellular morphology in hypoxic neurons compared with the KCN group. The data suggested that ginkgolides have a significant role to protect the primary cortical neurons from hypoxic injury induced by KCN.

Antioxidative activity of ginkgolides against superoxide in an aprotic environment.[Pubmed:9413545]

Chem Biol Interact. 1997 Oct 24;106(3):183-90.

The terpene lactones ginkgolide A, ginkgolide B, ginkgolide C, Ginkgolide J and bilobalide, which are components of a standardized extract (EGb 761) from leaves of Ginkgo biloba, as well as ginkgolide M from roots of G. biloba were studied regarding their reaction against superoxide (O2-) and hydroperoxyl radicals (HO2) in dimethyl sulfoxide as an aprotic solvent. It was found that the ginkgolides B, C, J, M as well as bilobalide react with superoxide and its protonated form as demonstrated by EPR and UV/VIS spectroscopy. The initial reaction rate with these oxygen-derived radicals is in the order of 100 M-1/s and below. Ginkgolide A does not react with superoxide under these conditions. From these findings it can be suggested that the superoxide scavenging effect of the ginkgolides B, C, J, M and bilobalide contributes to the antioxidant properties of G. biloba.

Protection against beta-amyloid induced abnormal synaptic function and cell death by Ginkgolide J.[Pubmed:17640772]

Neurobiol Aging. 2009 Feb;30(2):257-65.

A new Ginkgo biloba extract P8A (TTL), 70% enriched with terpene trilactones, prevents A beta(1-42) induced inhibition of long-term potentiation in the CA1 region of mouse hippocampal slices. This neuroprotective effect is attributed in large part to Ginkgolide J that completely replicates the effect of the extract. Ginkgolide J is also capable of inhibiting cell death of rodent hippocampal neurons caused by A beta(1-42). This beneficial and multi-faceted mode of action of the ginkgolide makes it a new and promising lead in designing therapies against Alzheimer's disease.

Description

Ginkgolide J is a main constituent of the non-flavone fraction of Ginkgo biloba with an IC50 range of 12-54 µM, has neuroprotective and anti neuronal apoptotic ability.

Keywords:

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