Phytochemical Investigation of Tephrosia candida: Hplc Separation of Tephrosin and 12a-Hydroxyrotenone

Abstract

Tephrosia candida (Roxb.) DC. (Papilionaceae) is a shrub; an extract of its seeds has been tested for insecticidal properties and found to be quite effective (1). Previous phytochemical studies have yielded a glycoside with anticancer activity (2), candidin (3), 6a, 12a-dehydrodeguelin (4), pongachin (4), and a corresponding chalcone (4). In the present paper, we report the isolation from the seeds and the separation of tephrosin and 12a-hydroxyrotenone by hplc; caffeic acid, ß-sitosterol, and its glucoside were also isolated.These compounds have been isolated for the first time from this genus, and the mixture of tephrosin and 12a-hydroxyrotenone has been resolved for the first time using hplc.

Urease inhibitory isoflavonoids from different parts ofCalopogonium mucunoides(Fabaceae)

“…These compounds were identified with the aid of their obtained spectral data (one and two dimension NMR and MS) and further confirmed by comparison of published data. The identified compounds include 4′-O-methylalpinumisoflavone (1), 4′-O-methylderrone (2) 3 , alpinumisoflavone (3) 4 , atalantoflavone (4) 16 , Calopogonium isoflavone A (5) 3,4 , daidzeine (6) 17 , 2′,4′,5′,7-tetramethoxyisoflavone (7) 4 , 7-O-methylcuneantin (8) 18 , cabreuvin (9) and 7-O-methylpseudobaptigenin (10) 4 and 6a,12a-dehydroxydegueline (11) 19 . Among all characterized constituents, daidzeine, 7-O-methylcuneantin, atalantoflavone and 6a, 12a-dehydroxydegueline have been isolated for the first time from C. mucunoides.…”

Inhibitory Effects of Thermolysis Transformation Products of Rotenone on Nitric Oxide Production

“…Isoflavonoid skeleton compounds 2 – 5 were isolated and characterized from Derris , Tephrosia , and Lonchocarpus from the family Fabaceae containing mother rotenone [ 20 , 21 ]. The phenolic acid, (−)-tubaic acid ( 6 ), was first identified in Derris roots [ 19 ], and it was reported as a transformed product induced by the alkaline degradation of rotenone [ 22 ].…”

Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata

“…Extraction of the air dried roots of T. aequilata with CH 2 Cl 2 /CH 3 OH (1:1) at room temperature, followed by chromatographic separation, afforded 11 compounds. Of these, obovatin methyl ether ( 5 ) [ 6 , 7 ], obovatachalcone ( 6 ) [ 7 ], praecansone B ( 7 ) [ 8 ], Z -praecansone A ( 8 ) [ 9 ], candidone ( 9 ) [ 2 ], isopongaflavone ( 10 ) [ 10 , 11 ], and β - sitostrol-3- O -glucoside ( 11 ) [ 12 ] are known, and were identified by comparison of their observed and reported spectroscopic and physical data. Compounds 1 – 4 ( Figure 1 ) are new and were identified by NMR spectroscopic and mass spectrometric analyses.…”

“…The fraction eluted with 10% EtOAc was purified by PTLC (7% EtOAc in n -hexane) to give candidone ( 9 , 10 mg) [ 2 ]. The fractions eluted with 15%–20% EtOAc in n -hexane were combined and subjected to column chromatography over Sephadex LH-20 (CH 2 Cl 2 /CH 3 OH, 1:1) to give isopongaflavone ( 10 , 1.2 g) [ 10 , 11 ]. The fraction eluted with EtOAc:MeOH (1:1) was crystallized from MeOH to yield β-sitosterol-3- O -glucoside ( 11 , 50 mg) [ 29 ].…”