Biosynthesis of rotenone and amorphigenin. Study of …

T1 - Synthesis of (2-[11C]methoxy)rotenone, a marker of mitochondrial complex I activity

Rotenone. XXVI. Synthesis of the Parent Substances of …

The increased fatty acid de novo synthesis provided the essential building blocks for TAG synthesis. To further support our notion, we determined the expression levels of glycerol phosphate acyltransferase (GPAT), a rate-limiting enzyme for TAG synthesis and found significant elevation of GPAT expression in cells after treatment with rotenone (). Consistent with the elevated mRNA level, GPAT protein content was increased as well (). These results further supported the finding that rotenone induces TAG deposition.

The first stereoselective total synthesis of rotenone is described in this dissertation.

Rotenone activated fatty acid synthesis

Rat liver mitochondria respond to changes in energy demand by modulating the amount of RNA synthesized. Coupled rat liver mitochondria were used to determine the relationship between mitochondrial respiration, ATP levels, and mitochondrial transcription. This system included oxidizable substrates (malate and glutamate) and constituents that could support both mitochondrial respiration and transcription. The respiratory inhibitor rotenone, phosphorylation inhibitor oligomycin, and the uncoupler of oxidative phosphorylation carbonyl-cyanide p-triflouromethoxyphehylhydrazone inhibited RNA synthesis. Addition of ADP stimulated mitochondrial transcription and peak RNA synthesis was observed at 1-2 mM ADP. At ADP concentrations above 2 mM, RNA synthesis decreased. These results demonstrate that mitochondrial transcription is tightly coupled to ATP levels.

Furthermore, as it has three stereogenic centres, rotenone poses an interesting and challenging synthetic target for organic chemists.

Three series of novel spin-labeled rotenone derivatives were synthesized and evaluated for cytotoxicity against four tumor cell lines, A-549, DU-145, KB and KBvin. All of the derivatives showed promising in vitro cytotoxic activity against the tumor cell lines tested, with IC 50 values ranging from 0.075 to 0.738 μg/mL. Remarkably, all of the compounds were more potent than paclitaxel against KBvin in vitro, and compounds 3a and 3d displayed the highest cytotoxicity against this cell line (IC 50 0.075 and 0.092 μg/mL, respectively). Based on the observed cytotoxicity, structure-activity relationships have been described.

Having constructed the dihydrobenzofuran in an enantiomeric excess of 94.8%, the chromene part of rotenone could then be synthesised.


Rotenone blocks ATP synthesis by:

In developed countries, scientists have learned that dried roots of rotenone producing plants can be ground into a powder that is useful as a garden insecticide. For many years, it was also a widely used agricultural insecticide applied to crops and livestock to control insect pests. Unfortunately, because rotenone producing plants grow only in the wild, the supply is dependent on natives who locate, dig, and dry theroots for sale to wholesalers. In recent years, agricultural uses of rotenone have declined in the face of new synthetic pesticides that can be mass produced but fishery needs have continued.

Synthesis of (2-( 11 C)methoxy)rotenone, a ..

In recent years, we have heard a great deal about synthetic pesticides that were designed and produced in chemical laboratories. Some of these are so unique or unusual that they are not readily broken down by normal biological systems. Such synthetic compounds may persist for long periods in the environment. Where does rotenone fall in the gamut of modern pesticides?

Synthesis of elliptone from rotenone

A. Results of studies using DNA repair, cytogenic analysis of bone marrow cells, embryonic mouse cells, eukaryotic microbial tests, and DNA synthesis tests showed no evidence that rotenone causes mutations or chromosome damage.

Rotenone had no effect on AA synthesis ..

AB - Rat liver mitochondria respond to changes in energy demand by modulating the amount of RNA synthesized. Coupled rat liver mitochondria were used to determine the relationship between mitochondrial respiration, ATP levels, and mitochondrial transcription. This system included oxidizable substrates (malate and glutamate) and constituents that could support both mitochondrial respiration and transcription. The respiratory inhibitor rotenone, phosphorylation inhibitor oligomycin, and the uncoupler of oxidative phosphorylation carbonyl-cyanide p-triflouromethoxyphehylhydrazone inhibited RNA synthesis. Addition of ADP stimulated mitochondrial transcription and peak RNA synthesis was observed at 1-2 mM ADP. At ADP concentrations above 2 mM, RNA synthesis decreased. These results demonstrate that mitochondrial transcription is tightly coupled to ATP levels.

Does rotenone inhibit ATP synthesis?

T1 - Synthesis and biological evaluation in Mice of (2-[11C]methoxy)-6′,7′-dihydrorotenol, a second generation rotenoid for marking mitochondrial complex I activity