From Derris elliptica

Rotenone (Figure 56-1) is obtained from Derris elliptica, D mallaccensis, Lonchocarpus utilis, and L urucu. The oral ingestion of rotenone produces gastrointestinal irritation. Conjunctivitis, dermatitis, pharyngitis, and rhinitis can also occur. Treatment is symptomatic. 

A systematic investigation of the free amino acids of the Leguminosae led to the isolation of a novel ninhydrin-positive compound from the leaves of Derris elliptica Benth. (Papilionidae) (93). This substance was analyzed as C6H,3N04 (microanalysis and high resolution mass spectrometry) and was shown to be an amino alcohol. The absence of a carbonyl in the 1R, the loss of 31 mass units in the mass spectrum, and a positive periodate cleavage reaction were best embodied into a dihydroxydihydroxymethylpyrrolidine structure. The relative simplicity of the NMR spectra (three peaks in the 13C spectrum four spin-system in the H spectrum) pointed out a symmetrical structure. Inasmuch as the material was optically active ([a]D 56.4, c = 7, H20), meso structures were ruled out, and the 2R, 3R, 4R, 5R relative configuration was retained (93). This structure (53) was further confirmed by an X-ray determination (94). 

Derr is or rotenone is a poisonous alkaloid that has long been used by indigenous peoples of Southeast Asia as arrow and fish poisons. Rotenone is now used widely as a rodenticide to kill small mammals and as an insecticide to kill pest insects. This chemical is mostly extracted from the plants Derris elliptica and D. malaccensis. 

A new natural imino-alcohol, 3,4-dihydroxy-2,5-dihydroxymethylpyrrolidine (1) has been isolated from the roots and leaves of Derris elliptica. Its structure and configuration have been settled principally by n.m.r. and mass spectrometry. It appears to be the first example of the occurrence of an iminopolyol in the vegetable kingdom. Trichostachine (2) has been found in the fruit of Piper guineense Schum,... 

Rotenone 30, the toxic principle from the roots of derris elliptica, is a natural insecticide. Its structure shows an unique combination of benzannelated dihydropyran, dihydro-4-pyrone and dihydrofuran ring systems. 

A series of piperidine alkaloids with hydroxyl substitutions have been isolated from a number of higher plants (54-56) (Fig. 29.19) (Herbert, 1986, 1988). Among these plant species are Lonchocarpus sericeus, L. costaricensis and Derris elliptica (Fabaceae), Moms species (Moraceae), Fagopyrum esculentum (Polygonaceae), and a fern of the... 

Dideoxy-2,5-imino-D-mannito I Alkaloid from the leaves of Derris elliptica and the seeds of Lonchocarpus sericeus (Leguminosae). Glycosidase inhibitor. Cryst. (EtOH/MezCO/EtOAc). 

Obt. from Derris malaccensis. Occurs in Crotalaria burhia also D. elliptica, Tephrosia odorata and T. toxicaria. 

Another class of i. are rotenoids derived from the roots and seeds of Derris (Deguelia) elliptica and Derris malaccensis (Leguminosae) and over 60 other plant species. A most active compound is ro-tenone [83-79-4], a polycylic compound that can be applied to food crops shortly before use, due to its rapid degradation after exposure to sunlight. Rotenone-containing i. are applied as dust, powder or emulsions. 

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