A natural inhibitor of p23 A natural inhibitor of p23
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Gedunin

Item No. 17328

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-5-(acetyloxy)-1-(3-furanyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyl-oxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione
CAS Number
2753-30-2
Synonyms
  • NSC 113497
Molecular Formula
C28H34O7
Formula Weight
482.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: 1 mg/mlDMSO: 100 mMEthanol: 1 mg/mlMethanol: 1 mg/ml
λmax
220 nm
SMILES
O=C1[C@@H]2[C@]3(O2)[C@]4(C)[C@H](OC(C)=O)C[C@@]5([H])C(C)(C)C(C=C[C@]5(C)[C@@]4([H])CC[C@@]3(C)[C@H](C6=COC=C6)O1)=O
InChi Code
InChI=1S/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
InChi Key
YJXDGWUNRYLINJ-BHAPSIHVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $134

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    Product Description

    Gedunin is a natural inhibitor of the heat shock protein (Hsp90; Item Nos. 22734 | 22735) co-chaperone p23 that also inhibits Hsp90 expression in human teratocarcinomal NTERA-2 cells in vitro at 5 µg/ml.1 This tetranortriterpenoid, which is isolated from A. indica, binds to and blocks the chaperone activity of p23 to induce apoptosis in HeLa-PRB cells in vitro at a concentration of 20 µM.2 Gedunin inhibits breast cancer cell proliferation in vitro, with IC50 values of 8.84 and 3.22 µM in MCF-7 and SKBr-3 cells, respectively, and inhibits the growth of PANC-1 pancreatic cancer cells (IC50 = 25 µM) by targeting the sonic hedgehog pathway to induce apoptosis.3,4 It also exerts anti-inflammatory effects in vivo. In a mouse model of articular inflammation induced by zymosan (Item No. 21175), gedunin (0.05-0.5 mg/kg, i.p.) reduces edema formation and the production of inflammatory cytokines.5 Gedunin (0.5 mg/kg) also inhibits the pleural accumulation of eosinophils and activated T lymphocytes in an ovalbumin-sensitized mouse model of allergic inflammation when administered prior to ovalbumin rechallenge.6 It also targets the lipopolysaccharide binding site and thus blocks Toll-like receptor 4 (TLR4) signaling in macrophages in vitro at a concentration of 10 µM.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tharmarajah, L., Samarakoon, S.R., Ediriweera, M.K., et al. In vitro anticancer effect of gedunin on human teratocarcinomal (NTERA-2) cancer stem-like cells. Biomed. Res. Int. 2017, 2413197 (2017).

    2. Patwardhan, C.A., Fauq, A., Peterson, L.B., et al. Gedunin inactivates the co-chaperone p23 protein causing cancer cell death by apoptosis. The Journal of Biological Chemisty 288(10), 7313-7325 (2013).

    3. Brandt, G.E.L., Schmidt, M.D., Prisinzano, T.E., et al. Gedunin, a novel hsp90 inhibitor: Semisynthesis of derivatives and preliminary structure-activity relationships. J. Med. Chem. 51(20), 6495-6502 (2008).

    4. Subramani, R., Gonzalez, E., Nandy, S.B., et al. Gedunin inhibits pancreatic cancer by altering sonic hedgehog signaling pathway. Oncotarget 8(7), 10891-10904 (2017).

    5. Conte, F.P., Kerraris, F.K., Costa, T.E.M.M., et al. Effect of gedunin on acute articular inflammation and hypernociception in mice. Molecules 20(2), 2636-2657 (2015).

    6. Ferraris, F.K., Moret, K.H., Figueiredo, A.B.C., et al. Gedunin, a natural tetranortriterpenoid, modulates T lymphocyte responses and ameliorates allergic inflammation. Int. Immunopharmacol. 14(1), 82-93 (2012).

    7. Borges, P.V., Moret, K.H., Maya-Monteiro, C.M., et al. Gedunin binds to myeloid differentiation protein 2 and impairs lipopolysaccharide-induced toll-like receptor 4 signaling in macrophages. Mol. Pharm. 88(5), 949-961.