Derris elliptica

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). 

In 1976, 1-deoxynojirimycin (2) was discovered as a natural product in a Moms species and coined moranoline.26 Incidentally, in the same year, a novel type of alkaloid was found in the liana plant, Derris elliptica, a native of Borneo but widespread in the tropics, and it was identified as 2,5-dideoxy-2,5-imino-D-mannitol (7, Scheme 3), also known as DMDP (2,5-dihydroxymethyl-3,4-dihy droxypyrrolidine).27... 

A. Welter, J. Jadot, G. Dardenne, M. Marlier, and J. Casimir, 2,5-Dihydroxymethyl 3,4-dihydrox-ypyrrolidine dans les feuilles de Derris elliptica, Phytochemistry, 15 (1976) 747-749. 

Other natural products in the group are built up by ring fusions of several types of ring systems. They include the garden insecticide rotenone (sometimes sold in the crude form as derris powder, the pulverized bark of the plant 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. 

Rotenone thus provides an excellent biodegradable insecticide, and is used as such either in pure or powdered plant form. Roots of Derris elliptica or Lonchocarpus species are rich sources of rotenone. 

Rotenone is the principal active insecticidal constituent of derris, the dried rhizome and roots of Derris elliptica, D. malaccensis (Leguminosae) and other species of Derris, and of lonchocarpus, the dried root of Lonchocarpus utilis, L. urucu and other species of Lonchocarpus (Leguminosae). 

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. 

Welter, A, Jadot, J, Dardenne, G, Marlier, M, Casimir, J, 2,5-Dihydroxymethyl-3,4-dihydroxy-pyrrolidine in the leaves of Derris elliptica. Phytochemistry, 15, 747-749, 1976. 

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,... 

DERRIS Derridis radix The drug consists the dried roots of Derris elliptica (Wallich) Benth. and Derris malaccensis Prain, family Fabaceae these Derris species grow in South East Asia, where they also are cultivated. They contain as active ingredient an iso-fla-vonoid rotenone, which has a pronounced insecticidal effect. Rotenone and similar substances have the great advantage that they do not leave any toxic residues. 

Danaus chrysippus L. (rosmarinine), 244 Danaus plexippus L. (rosmarinine), 244 Derris elliptica... 

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). 

Found in Crotalaria burhia, C. medicaginea, Derris elliptica, D. malaccensis, Lonchocarpus spp., Mundulea sericea, Piscidia mollis and Tephrosia spp. Some of these samples are the (—)-form, some the ( )-form and others have unreported opt. activity. 

Nitrogen-containing sugar analogs have recently been described fi-om several Fabaceae species. One of them, 2-5-dihydroxymethyl-3,4-hydroxypyrrolidine (DMDP), was first isolated form leaves and roots of Derris elliptica (10). These sugar mimics were shown to be powerfid glucosidadse inhibitors (11). DMDP acts as an antifeedant for locusts and is toxic for certain caterpillars and beetles. It was isolated in our laboratory fi-om the roots of Derris urucu (Mathias, L. Parente, J. P., unpublished data.)... 

---