A terpenoid lactone with diverse biological activities
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Ginkgolide A

Item No. 24970

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3S,3aS,4R,6aR,7aR,7bR,8S,10aS,11aS)-3-(1,1-dimethylethyl)hexahydro-4,7b-dihydroxy-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
CAS Number
15291-75-5
Synonyms
  • BN-52020
Molecular Formula
C20H24O9
Formula Weight
408.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 3 mg/ml
λmax
218 nm
SMILES
O=C(O1)[C@@H](C)[C@@]2(O)[C@]1([H])C[C@]34[C@@]25O[C@@]6([H])C3([C@@H](O)C(O6)=O)[C@H](C(C)(C)C)C[C@H]4OC5=O
InChi Code
InChI=1S/C20H24O9/c1-7-12(22)26-10-6-17-9-5-8(16(2,3)4)18(17)11(21)13(23)28-15(18)29-20(17,14(24)27-9)19(7,10)25/h7-11,15,21,25H,5-6H2,1-4H3/t7-,8+,9-,10+,11+,15+,17-,18?,19-,20-/m1/s1
InChi Key
FPUXKXIZEIDQKW-XUYRAXNCSA-N
Origin
Plant/Ginkgo biloba L.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ginkgolide A is a terpenoid lactone originally isolated from G. biloba leaves with diverse biological activities.1 Ginkgolide A inhibits platelet activating factor-dependent aggregation of human platelets (IC50 = 15.8 μg/ml).2 It also inhibits GABA-induced currents in Xenopus oocytes expressing human α1β2γ2L GABAA receptors with an IC50 value of 12 μM.3 Ginkgolide A (100 μM) reduces the proliferation rate of OVCA429 ovarian cancer cells by 40%.4 In vivo, ginkgolide A (1-2 mg/kg, p.o.) increases the time spent in the open arms of the elevated plus maze by 3-fold without altering activity level in mice, indicating anxiolytic-like activity.5 Ginkgolide A (10 mg/kg, p.o.) also reduces hexobarbital-induced sleeping time in mice by 44%.6 Ginkolide A (30 mg/kg per day) increases activity of the cytochrome P450 (CYP450) isoforms CYP1A2 and CYP2E1 by 1.82- and 1.27-fold, respectively, in rats.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Deng, Y., Bi, H.C., Zhao, L.Z., et al. Induction of cytochrome P450s by terpene trilactones and flavonoids of the Ginkgo biloba extract EGb 761 in rats. Xenobiotica 38(5), 465-481 (2008).

    2. Koch, E. Inhibition of platelet activating factor (PAF)-induced aggregation of human thrombocytes by ginkgolides: Considerations on possible bleeding complications after oral intake of Ginkgo biloba extracts. Phytomedicine 12(1-2), 10-16 (2005).

    3. Huang, S.H., Duke, R.K., Chebib, M., et al. Ginkgolides, diterpene trilactones of Ginkgo biloba, as antagonists at recombinant α1β2γ2L GABAA receptors. Eur. J. Pharmacol. 494(2-3), 131-138 (2004).

    4. Ye, B., Aponte, M., Dai, Y., et al. Ginkgo biloba and ovarian cancer prevention: Epidemiological and biological evidence. Cancer Lett. 251(1), 43-52 (2007).

    5. Kuribara, H., Weintraub, S.T., Yoahihama, T., et al. An anxiolytic-like effect of Ginkgo biloba extract and its constituent, ginkgolide-A, in mice. J. Nat. Prod. 66(10), 1333-1337 (2003).

    6. Wada, K., Sasaki, K., Miura, K., et al. Isolation of bilobalide and ginkgolide A from Ginkgo biloba L. shorten the sleeping time induced in mice by anesthetics. Biol. Pharm. Bull. 16(2), 210-212 (1993).