Dehydro-6-hydroxyrotenoid and lupenone from Tephrosia villosa

Two new geranyl flavanones from Tephrosia villosa

“…(Leguminosae) is an erect herb used widely in traditional Indian medicine in the treatment of dropsy and diabetes (Ambasta, 1986;Thammanna, Narayana Rao, & Madhava Chetty, 1994). Previous phytochemical studies on different parts of this species have led to the isolation of a number of flavonoids and isoflavonoids (Chandrasekharan, Amalraj, Khan, & Ghanim, 1983;Jayaraman, Ghanim, & Khan, 1980;Krupadanam, Sarma, Srimannarayana, & Rao, 1977;Krupadanam, Srimannarayana, & Rao, 1978;Prashant & Krupadanam, 1993a, 1993bRao & Srimannarayana 1980, 1981Sarma, Srimannarayana, & Rao, 1976). In our systematic search for polyphenolic constituents from Indian medicinal plants, we have investigated the roots of T. villosa for minor constituents and report here the isolation and characterisation of two new flavonoids, (2S)-5,4 0 -dihydroxy-7-O-[(E)-3, 7-dimethyl-2,6-octadienyl]flavanone (1) and (2S)-5,4 0 -dihydroxy-7-O-[(E)-3,7-dimethyl-2,6-octadienyl]-8-C-[(E)-3,7-dimethyl-2,6-octadienyl]-flavanone (2), together with three known compounds, 7-O-methylglabranin (3), tephcalostan (4) and 12a-dehydro-6-hydroxysumatrol (5).…”

“…Compounds 3-5 were identified by comparison of their spectral data with the literature values as 7-O-methylglabranin (3) (Jayaraman et al, 1980), tephcalostan (4) (Hari Kishore et al, 2003) and 12a-dehydro-6-hydroxysumatrol (5) (Prashant & Krupadanam, 1993a).…”

Elucidation of a new oleanane glycoside from Barringtonia asiatica

“…The samples were silylated and compared with silylated known standards. All NMR spectra were obtained using a Varian VXR-500S spectrometer with standard Varian pulse sequences and parameters, and standard 5 mm tubes and 20 mg samples at ambient temperature in pyridine-d 5 . Materials.…”

“…2 The Tephrosia species has been extensively studied, and it's piscicidal activity has been ascribed to various biologically active rotenoid compounds isolated from the roots of these plants. [3][4][5] The most well-known rotenoid natural product is rotenone, which has found commercial application both as a useful insecticide and as a piscicide for controlling unwanted fish species in recreational and other waterways 6 The biological activity of this compound has been ascribed to its ability to inhibit mitochondrial electron transport and consequently block oxidative phosphorylation. 7,8 There has been considerably less published on the Barringtonia species and no report on the principle compounds responsible for the reported piscicidal activity.…”

Antibacterial Triterpenoids from the Bark of Sonneratia alba (Lythraceae)

“…The methylene protons of H-2 at  H 1.48 and 1.75 were correlated to an oxygenated carbon at  C 79.8, whereas the oxygenated proton at  H 3.20 was correlated to the sp 3 carbon at C-2 ( C 27.6) and the quaternary sp 3 carbon at  C 40.2 (C-4), indicated that the hydroxyl group was located at C-3. The coupling constants of H-3 ( H 3.20, dd, J = 10.5, 5.5 Hz) observed in the 1 H NMR spectrum indicated a -orientation of the hydroxyl group at C-3 [17][18][19]. The relative configuration of 1 was identical to that of dihydrobetulinic acid, lupeol and and lupan-3-ol based on the J value and the chemical shifts in the 1 H NMR spectrum [20][21][22].…”