Flavonoids from Genista ephedroides

Abstract

Three new flavonoids (1-3) and 11 known compounds (genistein, isoprunetin, wighteone, laburnetin, alpinumisoflavone, genistin, genistein 8-C-glucoside, apigenin, isokaempferide, licoflavone C, and D-pinitol) were isolated from the aerial parts of Genista ephedroides. The structures of the new compounds were established as hydroxyalpinumisoflavone (1) [4', 5-dihydroxy-2"-methyl-2"-hydroxymethylpyrano(5",6":6,7)isoflavone], ephedroidin (2) [4',5, 7-trihydroxy-8-(2-hydroxy-3-methyl-3-butenyl)flavone], and genisteone (3) (7-O-glucosylwighteone) by means of spectroscopic methods.

Rapid Identification of Antioxidant Compounds of Genista saharae Coss. & Dur. by Combination of DPPH Scavenging Assay and HPTLC-MS

“…, 3',4',5,7-tetrahydroxyisoflavone ( 1 ). The MS analysis of the third spot gave also one major ion at m / z 351.2 and a database search for the genus Genista gave only one output: hydroxyalpinumisoflavone ( 2 ), previously reported from Genista ephedroides [17]. Despite the nice isotopic peak observed in the mass spectrum of A4 at m / z 465.2, no conclusion could be made on the identity of this compound.…”

Isoflavonoids of the Leguminosae

“…141 Another Sardinian endemic, G. ephedroides DC., yielded hydroxyalpinumisoflavone as a constituent of the aerial parts of the plant. 142 This compound had the same planar structure as erysubin B (49), 131 but opposite optical rotation, suggesting a possible enantiomeric relationship.…”

“…A soybean product (molasses) also yielded the first triacylated isoflavone glycoside, a 2,4,6-tri-O-acetyl derivative (117) 181 of glycitein 7-O-b-glucopyranoside (glycitin). Two glycosides of prenylated isoflavones were obtained from the same source (113,142). 181 The majority of isoflavone glycosides characterised to date are either 7-O-, 4 -O-or 7,4 -di-O-glycosides.…”

Isoflavonoids of the Leguminosae

“…92 In an earlier publication from the same research group, genisteone, the 7-O-bglucopyranoside of 5,7,4 0 -trihydroxy-6-prenylisoavone (the biosynthetic precursor of alpinumisoavone), was recorded as a constituent of the aerial parts of Genista ephedroides. 108 A 4 0 -O-bglucopyranoside of glycitein (77) isolated from MeOH extracts of the stem bark of Styphnolobium japonicum showed mild inhibition of aldose reductase. 93 Two O-glycosides of dimethyl ethers of 6,7,4 0 -trihydroxyisoavone have been reported as caragiside A (78) and maackiaisoavonoside (79).…”