LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

(-)-cis-Deguelin

Systematic Name

(7aS,13aS)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7 (7aH)-one

Synonyms

LM ID

LMPK12060019

Formula

C₂₃H₂₂O₆

Exact Mass

Calculate m/z

394.14164

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

(−)-Deguelin is a rotenoid that has been found in T. vogelii and has diverse biological activities.^1,2,3,4 It inhibits mitochondrial complex I, also known as NADH dehydrogenase, activity in bovine heart electron transport particles and phorbol 12-myristate 13-acetate-induced ornithine decarboxylase (ODC) activity in MCF-7 breast cancer cells (IC50s = 6.9 and 11 nM, respectively).² (−)-Deguelin (100 nM) induces apoptosis in MCF-7 and SK-BR-3 breast cancer cells.³ It induces mortality in adult bruchid beetles (C. maculatus) when used at concentrations ranging from 10 to 500 ppm.¹ (−)-Deguelin (6 mg/kg) induces nigrostriatal dopaminergic degeneration in rats.⁴

This information has been provided by Cayman Chemical

References

1. Belmain, S.R., Amoah, B.A., Nyirenda, S.P., et al. Highly variable insect control efficacy of Tephrosia vogelii chemotypes. J. Agric. Food Chem. 60(40), 10055-10063 (2012).

2. 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).

3. Peng, X.H., Karna, P., O'Regan, R.M., et al. Down-regulation of inhibitor of apoptosis proteins by deguelin selectively induces apoptosis in breast cancer cells. Mol. Pharmacol. 71(1), 101-111 (2007).

4. Caboni, P., Sherer, T.B., Zhang, N., et al. Rotenone, deguelin, their metabolites, and the rat model of Parkinson’s disease. Chem. Res. Toxicol. 17(11), 1540-1548 (2004).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

Derris trifoliata (#185716)

Magnoliopsida (#3398)

7a-O-methyldeguelol, a modified rotenoid with an open ring-C, from the roots of Derris trifoliata,
Phytochemistry, 2005

DOI: 10.1016/j.phytochem.2005.02.005

String Representations

InChiKey (Click to copy)

ORDAZKGHSNRHTD-UXHICEINSA-N

InChi (Click to copy)

InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1

SMILES (Click to copy)

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