Die Konstitution des Pachyrrhizins

Rautandiols A and B, Pterocarpans and Cytotoxic Constituents from Neorautanenia mitis,1

“…Neorautanenia species of the Fabaceae are widespread in central and south Africa. These plants are used by indigenous populations as fish poisons, as insecticides, and to treat syphilis. − Several chemical studies on Neorautanenia species, including N. edulis , , N. pseudopachyrrhiza , , and N. amboensis , − and on the closely related Pachyrrhiza erosus − have been reported previously. A study on Neorautanenia mitis in 1987 16a,b led to the purification of dehydroneotenone, dolineone, 12-hydroxydolineone, 12-hydroxyrotenone, neodulin, neotenone, and pachyrrhizine.…”

Isolation and Structural Elucidation of Potentially Insecticidal and Acaricidal Isoflavone-Type Compounds from Neorautanenia mitis

“…The petroleum ether total extract of N. mitis roots showed significant acaricidal properties that were attributed to the presence of 12a-hydroxyrotenone [7].Neorautanenia species are a widespread group of Fabaceae (Papilionaceae) plants of Central and South Africa and are known for their poisonous properties (1). These plants are used by the native population as fish poison (2-5) and insecticide (6,7), while in the traditional medicine of Central Africa they are used against syphilis (8) and the treatment of female frigidity.4 The possible use of some of these plants for killing bilharziacarrying fresh water snails of the genera Bulinus and Biophalaria has also been reported (9).Several chemical studies have been performed already on Neorautanenia species, among others N. ficifolia (3,14,15), N. edulis (2,4,12,16,18), N. pseudopachyrrhiza (10,11,13), N. amboensis (5,12,17,19), and the related Pachyrrhizus erosus (20)(21)(22). In the course of our investigation on medicinal plants from Rwanda (Central Africa) we investigated Neorautanenia mitis (A.…”

“…Several chemical studies have been performed already on Neorautanenia species, among others N. ficifolia (3,14,15), N. edulis (2,4,12,16,18), N. pseudopachyrrhiza (10,11,13), N. amboensis (5,12,17,19), and the related Pachyrrhizus erosus (20)(21)(22). In the course of our investigation on medicinal plants from Rwanda (Central Africa) we investigated Neorautanenia mitis (A.…”

Modified coumarins. 29. Synthesis of structural analogs of natural 6-arylfuro[3,2-g]chromen-7-ones

“…However, compounds containing aryl substituents in these positions have been isolated from natural sources. Examples of such secondary metabolites based on the 3-arylcoumarin core are pachyrrhizin {6-(6-methoxy-1,3-benzodioxol-5-yl)furo[3,2-g]chromen-7-one}, which was isolated from the plants Pachyrrhizus erosus [3][4][5], P. tuberosus [6], Neorautassenia pseudopachyrriza [7], and N. edulis [8][9][10]; neofolin {9-methoxy-6-(6-methoxy-1,3-benzodioxol-5-yl)furo[3,2-g]chromen-7-one}, which was isolated from Neorautanenia ficifolia [11]; and 6-(2,4,5-trimethoxyphenyl)furo[3,2-g]chromen-7-one, which is produced by P. tuberosus [6].We synthesized substituted 6-arylfuro[3,2-g]chromen-7-ones, structural analogs of natural furocoumarins, based on the 3-arylcoumarin core.7-Acetoxycoumarins 1-5 were prepared by a Perkin-Oglialoro reaction [12] of 2,4-dihydroxybenzaldehyde and substituted phenylacetic acids in acetic anhydride in the presence of pyridine. Acidolysis of 1-5 formed 7-hydroxy-3-arylcoumarins 6-10 that were required for further transformations.…”

“…However, compounds containing aryl substituents in these positions have been isolated from natural sources. Examples of such secondary metabolites based on the 3-arylcoumarin core are pachyrrhizin {6-(6-methoxy-1,3-benzodioxol-5-yl)furo[3,2-g]chromen-7-one}, which was isolated from the plants Pachyrrhizus erosus [3][4][5], P. tuberosus [6], Neorautassenia pseudopachyrriza [7], and N. edulis [8][9][10]; neofolin {9-methoxy-6-(6-methoxy-1,3-benzodioxol-5-yl)furo[3,2-g]chromen-7-one}, which was isolated from Neorautanenia ficifolia [11]; and 6-(2,4,5-trimethoxyphenyl)furo[3,2-g]chromen-7-one, which is produced by P. tuberosus [6].…”