A cardenolide and an active metabolite of periplocin with diverse biological activities
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Parent Compound(s)
25216Periplocin
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Periplogenin

Item No. 35047

Technical Information
Formal Name
3β,5β,14-trihydroxy-card-20(22)-enolide
CAS Number
514-39-6
Synonyms
  • Desoxostrophanthidin
  • 5β-hydroxy Digitoxigenin
Molecular Formula
C23H34O5
Formula Weight
Purity
≥98%
Formulation
A solid
λmax
218 nm
SMILES
O[C@@]12[C@@]3([H])[C@@](CC[C@@]1([C@](C4=CC(OC4)=O)([H])CC2)C)([H])[C@@]5([C@](CC3)(C[C@H](CC5)O)O)C
InChi Code
InChI=1S/C23H34O5/c1-20-7-3-15(24)12-22(20,26)9-5-18-17(20)4-8-21(2)16(6-10-23(18,21)27)14-11-19(25)28-13-14/h11,15-18,24,26-27H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,20+,21+,22-,23-/m0/s1
InChi Key
QJPCKAJTLHDNCS-FBAXFMHRSA-N
Origin
Plant/Periploca sepium
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Periplogenin is a cardenolide and an active metabolite of periplocin (Item No. 25216) that has been found in P. graeca and has diverse biological activities.1,2,3 It reduces the activity of porcine Na+/K+ ATPase when used at concentrations of 0.3 or 0.6 µM.1 Periplogenin induces apoptosis in U937 and PC3 prostate cancer cells, as well as inhibits the proliferation of these cells (EC50s = 1.41 and 1.2 µM, respectively), when used at concentrations of 0.1 or 0.2 µM. It increases the production of reactive oxygen species (ROS) and induces necroptosis in HaCaT keratinocytes when used at a concentration of 2 µg/ml.3 Topical application of periplogenin reduces ear thickness in a mouse model of psoriasis induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bloise, E., Braca, A., De Tommasi, N., et alPro-apoptotic and cytostatic activity of naturally occurring cardenolides. Cancer Chemother. Pharmacol. 64(4), 793-802 (2009).

    2. He, J., Bo, F., Tu, Y., et alA validated LC-MS/MS assay for the simultaneous determination of periplocin and its two metabolites, periplocymarin and periplogenin in rat plasma: Application to a pharmacokinetic study. J. Pharm. Biomed. Anal. 114, 292-295 (2015).

    3. Zhang, W.-J., Song, Z.-B., Bao, Y.-L., et alPeriplogenin induces necroptotic cell death through oxidative stress in HaCaT cells and ameliorates skin lesions in the TPA- and IMQ-induced psoriasis-like mouse models. Biochem. Pharmacol. 105, 66-79 (2016).