Rotenone and rotenoids

One of the most important methods of rotenoid synthesis is that of Miyano 

7-dimethoxychroman-3-one-pyrrolidyl enamine (43) with tubaic acid chloride (44). 

Owing to the structural similarity of rotenoids and isoflavonoides, Griesbach and Otlis (1961), and later Crombie and Thomas (1967), assumed a biogenetic relation between the two families of compounds. Combos et al. (1974) were the first to isolate flavanones, the biointerm iates of rotenoids. 

Fukami et al. (1959) found a close relatio iship between the insecticidal efficiency of rotenoids and the degree of glutamate oxidation inhibition. The effect is accompanied by a substantial decrease in oxygen uptake. Lindahl and Oberg (1961) found that rotenone inhibits the aerobic oxidation of pyruvate. This effect can be counteracted with methylene blue, which permits the conclusion that rotenone inhibits mitochondrial respiration by reducing the activity of NADH -dehydro-genase. Hull and Whereat (1967) came to similar conclusions from their experimental results. 

The toxicity of rotenoids to warm-blooded animals varies within wide limits and depends on the mode of application and on the species of the test animal. Similarly, great differences are observed with respect to insecticidal toxicity, depending on the insect species. The action develops slowly, which constitutes a practical disadvantage in the case of insects which chew rapidly. 

---

Fukami H, Nakajima M (1971) Rotenone and rotenoids. In Jacobson M, Crosby DG (eds) Naturally occurring insecticides. Marcel Dekker, New York, p 71... 

---