A phthalide with diverse biological activities
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Levistolide A

Item No. 34386

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1Z,5S,5aS,8Z,10bS,10cS)-1,8-dibutylidene-5,5a,6,7,8,10b-hexahydro-1H-5,10c-ethanonaphtho[1,2-c:7,8-c′]difuran-3,10-dione
CAS Number
88182-33-6
Synonyms
  • (Z,Z')-Diligustilide
  • Z-Ligustilide Dimer
Molecular Formula
C24H28O4
Formula Weight
380.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:2): 0.3 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/ml
λmax
231, 277 nm
SMILES
CCC/C=C1[C@@]23[C@@]4([H])C5=C(CC[C@@]4([H])[C@H](CC3)C=C2C(O/1)=O)/C(OC5=O)=C/CCC
InChi Code
InChI=1S/C24H28O4/c1-3-5-7-18-16-10-9-15-14-11-12-24(21(15)20(16)23(26)27-18)17(13-14)22(25)28-19(24)8-6-4-2/h7-8,13-15,21H,3-6,9-12H2,1-2H3/b18-7-,19-8-/t14-,15+,21-,24+/m1/s1
InChi Key
UBBRXVRQZJSDAK-ZJHGLIIDSA-N
Origin
Plant/Ligusticum chuanxiong
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $167

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    10 mg

    $255

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    25 mg

    $437

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    Product Description

    Levistolide A is a phthalide that has been found in Angelica tenuissima and has diverse biological activities.1,2,3,4 It inhibits histamine release induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) and A23187 from HMC-1 human mast cell leukemia cells when used at a concentration of 10 µM.1 Levistolide A (100 µM) induces the production of reactive oxygen species (ROS), endoplasmic reticulum (ER) stress, and apoptosis in HCT116 colon cancer cells.2 It prevents ethanol-induced gastric ulcers in rats when administered at a dose of 10 mg/kg.3 Levistolide A (2 mg/kg) decreases aggregation of amyloid-β in brain and improves spatial and learning memory in the APP/PS1 transgenic mouse model of Alzheimer’s disease.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Choi, H.G., Je, I.-G., Kim, G.J., et al. Chemical constituents of the root of Angelica tenuissima and their anti-allergic inflammatory activity. Nat. Prod. Commun. 12(5), 779-780 (2017).

    2. Yang, Y., Zhang, Y., Wang, L., et al. Levistolide A induces apoptosis via ROS-mediated ER stress pathway in colon cancer cells. Cell. Physiol. Biochem. 42(3), 929-938 (2017).

    3. Velázquez-Moyado, J.A., Martínez-González, A., Linares, E., et al. Gastroprotective effect of diligustilide isolated from roots of Ligusticum porteri coulter & rose (Apiaceae) on ethanol-induced lesions in rats. J. Ethnopharmacol. 174, 403-409 (2015).

    4. Qu, X., Guan, P., Han, L., et al. Levistolide A attenuates Alzheimer’s pathology through activation of the PPARγ pathway. Neurotherapeutics 18(1), 326-339 (2021).