New natural rotenoid and pterocarpanoid analogues from Neorautanenia Amboensis

Caeruleanone A, a Rotenoid with a New Arrangement of the D-Ring from the Fruits of Millettia caerulea

“…Eleven known rotenoids inclusive of deguelin, 8 6a,12a-dehydrodeguelin, 8 11-hydroxy-6a,12a-dehydrodeguelin, 8 erythynone, 19 12a-hydroxyerythynone, 19 millettosin, 3 , 20 12a-hydroxyisomillettone, 21 rotenone, 22 cis -(6aβ,12aβ)-hydroxyrotenone, 22 tephrosin, 8 and 11-hydroxytephrosin 8 were also purified in this study. This corresponds to the second isolation of erythynone, 12a-hydroxyerythynone, and 12a-hydroxyisomillettone.…”

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.…”

Prenylated Flavonoids from the Roots of Tephrosia rhodesica

“…The structures of the isolated secondary metabolites were determined by NMR spectroscopic, mass spectrometric, and single-crystal X-ray diffractometric analyses. In addition to the five new secondary metabolites (1−5), the known tephrowatsin B (6), 8 tephrinone (7), 9 glabranin (8), 10 quercetol B (9), 11 maackiain (10), 12 6a-hydroxymaackiain (11), 13 pisatin (12), 14 tephrosin (13), 15 rotenone ( 14), 15 6hydroxyrotenone (15), 16 12a-hydroxyrotenone ( 16), 17 hildecarpin (17), 18 3-hydroxy-2-methoxy-8,9-methylenedioxypterocarpene (18), 19 isoliquirtigenin (19), 20 D-pinitol (20), 21 and tephrowatsin A (21) 8 were identified by comparison of their observed and reported spectroscopic data (see pages S22−S34 in the Supporting Information).…”

“… 14 The fractions eluted with 8% EtOAc in iso -hexane were subjected to column chromatography on a silica gel (200 g) with 3% EtOAc in iso -hexane to give tephrowatsin A ( 21 , 10 mg), 8 with 5% EtOAc in iso -hexane to give rhodiflavan A ( 2 , 50 mg), and with 10% EtOAc in iso -hexane to provide rhodiflavan B ( 3 , 20 mg) and rhodiflavan C ( 4 , 15 mg), which were further purified by preparative HPLC (CH 3 OH–H 2 O gradient elution). The fractions eluted with 9%–10% EtOAc in iso -hexane were combined and purified by column chromatography on a Sephadex LH-20 column (CH 2 Cl 2 –CH 3 OH; 1:1), and subsequently by preparative HPLC (CH 3 OH–H 2 O gradient elution) to give tephrosin ( 13 , 10 mg), 15 rotenone ( 14 , 15 mg), 15 6-hydroxyrotenone ( 15 , 10 mg), 16 12a-hydroxyrotenone ( 15 , 10 mg), 17 rhodacarpin ( 5 , 10 mg), hildecarpin ( 17 , 10 mg), 18 and 3-hydroxy-2-methoxy-8–9-methylenedioxypterocarpene ( 18 , 15 mg). 19 The fractions eluted with 12% EtOAc in iso -hexane gave isoliquirtigenin ( 19 , 15 mg), 20 and those eluted with 20% EtOAc in iso -hexane gave d -pinitol ( 20 , 900 mg).…”