A tricyclic diterpene
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Euphorbiasteroid

Item No. 27822

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
benzeneacetic acid, (1aR,2'R,2E,4aR,6S,7S,7aR,8S,11aS)-4a,8-bis(acetyloxy)-1,1a,4,4a,5,6,7,7a,8,10,11,11a-dodecahydro-1,1,3,6-tetramethyl-4-oxospiro[9H-cyclopenta[a]cyclopropa[f]cycloundecene-9,2'-oxiran]-7-yl ester
CAS Number
28649-59-4
Molecular Formula
C32H40O8
Formula Weight
552.7
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
λmax
273 nm
SMILES
C/C1=C/[C@@H](C2(C)C)[C@@H]2CC[C@]3(OC3)[C@@H](OC(C)=O)[C@]([C@@H](OC(CC4=CC=CC=C4)=O)[C@@H](C)C5)([H])[C@@]5(OC(C)=O)C1=O
InChi Code
InChI=1S/C32H40O8/c1-18-14-24-23(30(24,5)6)12-13-31(17-37-31)29(38-20(3)33)26-27(39-25(35)15-22-10-8-7-9-11-22)19(2)16-32(26,28(18)36)40-21(4)34/h7-11,14,19,23-24,26-27,29H,12-13,15-17H2,1-6H3/b18-14-/t19-,23-,24+,26+,27-,29-,31+,32+/m0/s1
InChi Key
SDGDWRYYHQOQOJ-QBGQQMMYSA-N
Origin
Plant/Euphorbia lathyris L.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $134

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    50 mg

    $253

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    100 mg

    $453

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    250 mg

    $1,058

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    Product Description

    Euphorbiasteroid is a tricyclic diterpene that has been found in the plant E. lathyris.1 It inhibits early-stage adipogenesis of 3T3-L1 cells, decreasing intracellular triglyceride accumulation when used at concentrations of 25 and 50 µM.2 It decreases the expression of Fas, C/EBPα, PPARγ, and SREBP-1c and increases phosphorylation of AMP-activated protein kinase (AMPK) and acetyl-coenzyme A carboxylase (ACC) in 3T3-L1 cells. Euphorbiasteroid inhibits proliferation of HL-60 cells in a concentration-dependent manner, as well as induces apoptosis and increases the expression of Fas and Fas ligand (FasL) and the activity of caspase-3 and caspase-8 in HL-60 cells.3 It increases P-glycoprotein activity, reverses multi-drug resistance, and restores cytotoxicity of the anticancer agents vinblastine (Item No. 11762), paclitaxel (Item No. 10461), and doxorubicin (Item No. 15007) to MES-SA/Dx5 sarcoma cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Adolf, W., Hecker, E., Balmain, A., et al. “Euphorbiasteroid” (epoxy-lathyrol). A new tricyclic diterpene from Euphorbia lathyris L. Tetrahedron Lett. 11(26), 2241-2244 (1970).

    2. Park, S.-J., Park, J.H., Han, A., et al. Euphorbiasteroid, a component of Euphorbia lathyris L., inhibits adipogenesis of 3T3-L1 cells via activation of AMP-activated protein kinase. Cell Biochem. Funct. 33(4), 220-225 (2015).

    3. Guo, F., Li, X., Zhang, C., et al. Roles and mechanisms of Fas/FasL in the apoptosis of HL-60 cells induced by euphorbiasteroid. J. Int. Oncology 41(9), 679-684 (2014).

    4. Choi, J.S., Kang, N.S., Min, Y.K., et al. Euphorbiasteroid reverses P-glycoprotein-mediated multi-drug resistance in human sarcoma cell line MES-SA/Dx5. Phytother. Res. 24(7), 1042-1046 (2010).