Substance
ID:449388
Names and Identifiers
IUPAC name
(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
Synonyms
RotenoneParaderilDerrinNicoulineNoxfishDactinolDerrisDri-kilTubotoxin
IUPAC Traditional name
(1S,6R,13S)-16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
Registration numbers
CAS Number
Properties
Product Information
Application(s)
Antineoplastic agent
Potent mitochondrial poison
Contact insecticide and pesticide
Biological Source
Constit. of the root of Derris elliptica .
Widely distrib. in the Leguminosae (Papilionoideae) e.g. in many other Derris spp. Lonchocarpus spp. Millettia spp., Tephrosia spp., Amorpha fruticosa,
Antheroporum pierrei, Crotalaria burhia, Crotalaria medicaginea, Mundulea pauciflora, Mundulea sericea, Neorautanenia amboensis, Neorautanenia ficifolia, Ormocarpum glabrum, Pachyrrhizus erosus,
Piscidia erythrina, Piscidia mollis, Poiretia tetraphylla and Spatholobus roxburghii.
Also in Verbascum thapsus (Scrophulariaceae)
Pharmacology Properties
Mechanism of Action
Inhibits the transfer of electrons from Fe-S centers in Complex I to ubiquinone
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 99A, (ir)
• Abidi, S.L., J. Het. Chem., 1987, 24, 845, (hplc, resoln)
• Blasko, G. et al., J. Nat. Prod., 1989, 52, 1363, (cmr)
• Crombie, L. et al., Phytochemistry, 1998, 49, 1479-1507, (rev, biosynth)
• Reed, R.I. et al., J.C.S., 1963, 5949, (ms)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1424, (occur)
• Unai, T. et al., Agric. Biol. Chem., 1973, 37, 387; 897, (synth)
• Sasaki, I. et al., Agric. Biol. Chem., 1979, 43, 137, (synth)
• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A363
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1131
• Ingham, J.L., Prog. Chem. Org. Nat. Prod., 1983, 43, 1, (rev, occur)
• Bhandari, P. et al., J.C.S. Perkin 1, 1992, 839; 851, (biosynth)
• Handbook of Pesticide Toxicology, (Eds. Hayes, W.J. et al), Academic Press, 1991, 599, (tox, rev)
• Carlson, D.G. et al., Tetrahedron, 1973, 29, 2731, (pmr)
• Dangerous Prop. Ind. Mater. Rep., 1989, 9, 74, (rev, tox)
• Hayashi, H. et al., Biosci., Biotechnol., Biochem., 1997, 61, 914-916, (activity)
• Pesticide Manual, 9th edn., 1991, No. 10610
• Bchi, G. et al., J.C.S., 1961, 2843, (abs config)
• Crombie, L. et al., J.C.S. Perkin 1, 1973, 1277; 1285; 1975, 1497, (synth, biosynth, cmr)
• Begley, M.J. et al., Chem. Comm., 1975, 850, (cryst struct)
• Nunlist, R. et al., J. Het. Chem., 1988, 25, 351, (pmr, cmr)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, RNZ000
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 923A, (nmr)
• Haley, T.J., J. Environ. Pathol. Toxicol., 1978, 1, 315, (rev)
• Rossi, M. et al., Bioorg. Chem., 1988, 16, 376, (cryst struct, conformn)