An antineoplastic and piscicidal rotenoid
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Tephrosin (synthetic)

Item No. 19840

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(7aR,13aR)-13,13a-dihydro-7a-hydroxy-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7(7aH)-one
CAS Number
76-80-2
Synonyms
  • Deguelinol I
  • Hydroxydeguelin
Molecular Formula
C23H22O7
Formula Weight
410.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: soluble
SMILES
CC(C=C1)(C)OC2=C1C(O3)=C(C=C2)C([C@@]([C@@]3([H])CO4)(O)C5=C4C=C(OC)C(OC)=C5)=O
InChi Code
InChI=1S/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1
InChi Key
AQBZCCQCDWNNJQ-AUSIDOKSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    Cayman Chemical
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    Product Description

    Tephrosin is a rotenoid first isolated from the leaves and seeds of T. purpurea and T. vogelii that exhibits antineoplastic and piscicidal activities. The toxic actions of this compound are attributed to its ability to inhibit the NADH:ubiquinone oxidoreductase with an IC50 value of 98nM.1 Tephrosin is also reported to induce ornithine decarboxylase activity with an IC50 value of 147 nM.1 Tephrosin has been shown to enhance the cytotoxic activity of 2-deoxy-D-glucose (Item No. 14325) against various cancer human cancer cell lines, depleting intracellular ATP and inducing apoptosis.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fang, N., and Casida, J.E. Anticancer action of cubé insecticide: Correlation for rotenoid constituents between inhibition of NADH: Ubiquinone oxidoreductase and induced ornithine decarboxylase activities. Proc. Natl. Acad. Sci. USA 95(7), 3380-3384 (1998).

    2. Choi, Y., and Lee, J.H. The combination of tephrosin with 2-deoxy-D-glucose enhances the cytotoxicity via accelerating ATP depletion and blunting autophagy in human cancer cells. Cancer Biol.Ther. 12(11), 989-996 (2011).