Endgültige konstitutionsaufklärung und synthese von narirutin, didymin, rhoifolin, poncirin und fortunellin

Secondary Metabolites from Satureja Species. New Triterpenoid from Satureja acinos

“…A material insoluble in CHC13 and also present in the crude extract of S. acinos was identified as naringenin 7 -(6"-0-a-L-rhamnopyranosylß -Dglucopyranoside), considering theand 13C-nmr data obtained with the natural compound and its peracetylated derivative and the glc results obtained with the TMSi derivatives of the sugar moiety. Although previously isolated (5) and synthetized (7), to our knowledge (14-16) no 13C-nmr data of this glycoside has been previously published (see Experimental section). This is also the case for eriodictyol 7-(6"-0-a-L-rhamnopyranosyl^-D-glucopyranoside) previously found in lemon peels (6) and isolated now from S. montana.…”

Synthesis of [Ring B-13C6] Diosmin

“…The product was recrystallized from EtOAc/pentane to give the product 3: yield 2.8 g (35%); mp 157-160°. The structure was confirmed by *Hnmr spectrometry (19): 3.85 ppm (3H, OMe), 4.55 ppm(1.2 H, CO-CH2-CO corresponding to the keto form), 4.90 ppm (2H, CH2-Ph), 5.12 ppm (2H, CH2-Ph), 5.18 ppm (2H, CH2-Ph), 6.15-6.40 ppm (2H, H-3 and H-5), 6.95 ppm (1H, H-5'), 7.18 ppm (0.8 H, =CH, corresponding to the enol form), 7.30-7.40 ppm (15 H, aromatic rings), 7.40-7.55 ppm (2H, H-2' and H-6'), 12.5 ppm(lH, OH), 13.6ppm(lH, OH). Comparing the intensities of the 7.18 ppm and 4.55 ppm peaks, it is concluded that the enol form predominates.…”

“…[Ring B^C^-diosmetin [4],-The ß-diketone (5 g, 0.0085 mol) was dissolved under argon in glacial HOAc (80 ml), and anisóle (8 ml) and 48% HBr in HOAc (10 ml) were added. The mixture was stirred and heated at 90°until complete dissolution; the mixture was then set aside overnight at 70°.…”