LIPID MAPS

Structure Database (LMSD)

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Common Name

Tephrosin

Systematic Name

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

Synonyms

LM ID

LMPK12060047

Formula

C₂₃H₂₂O₇

Exact Mass

Calculate m/z

410.136555

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

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 against various cancer human cancer cell lines, depleting intracellular ATP and inducing apoptosis.²

This information has been provided by Cayman Chemical

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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

Tephrosia vogelii (#1157238)

Magnoliopsida (#3398)

TEPHROSIN. I. THE COMPOSITION OF TEPHROSIN AND ITS RELATION TO DEGUELIN,
Journal of the American Chemical Society, 1931

DOI: 10.1021/ja01353a042

String Representations

InChiKey (Click to copy)

AQBZCCQCDWNNJQ-AUSIDOKSSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C12OC(C)(C)C=CC1=C1O[C@]3([H])COC4C=C(OC)C(OC)=CC=4[C@]3(O)C(=O)C1=CC=2