A New Prenylated Dehydrorotenoid from Tephrosia villosa Seeds

Abstract

From the seeds oiTephrosia villosa, a new prenylated dehydrorotenoid, identified as a 6a, 12a-dehydro-2,3,6-trimethoxy-8-(3',3'-dimethylallyl)-9,11-dihydroxyrotenone [1], has been isolated along with 12a-hydroxy-a-toxicarol (11-hydroxytephrosin) [2] and lupeol. Their structures were established on the basis of spectral evidence.

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).…”

Antidiabetic and Cytotoxic Activities of Rotenoids and Isoflavonoids Isolated from Millettia pachycarpa Benth

“…Compounds 1 – 7 were isolated from the root extract, whereas compounds 8 – 16 were isolated from the leaf extract. The known compounds were identified as 6a,12a-dehydro-α-toxicarol ( 1 ), (−)-6-hydroxy-6a,12a-dehydro-α-toxicarol ( 2 ), (+)-(6a R ,12a R )-12a-hydroxy-α-toxicarol ( 4 ), , (+)-α-toxicarol ( 5 ), , (−)-sumatrol ( 6 ), , toxicurol isoflavone ( 7 ), 6,8-diprenylorobol ( 8 ), 6,8-di- C -prenylpratensein ( 9 ), 6,8-diprenylgenistein ( 10 ), isolupalbigenin ( 11 ), , lupalbigenin ( 12 ), isoerysenegalensein E ( 13 ), , erysenegalensein E ( 14 ), euchrenone b10 ( 15 ), and senegalensin ( 16 ) by analysis of their spectroscopic data and by comparisons of these data with those reported.…”

Natural Products from the Genus Tephrosia

“…Forty-two isoflavones, 94 – 13 5 , have been isolated and identified from this genus [5,22,64,65,66,67,68,69,70,71,72,73,74,75,76,77,78,79,80,81,82,83,84,85,86,87,88,89,90,91]. Among them, 111 – 125 were identified as rotenoids [74,75,76,77,78,79,80,81,82], 94 and 126 – 13 5 were identified as coumestan derivatives [22,83,84,85,86,87,88,89,90,91].…”