Naringenin 7-rutinoside

Synonyms cas 10236-47-2 NARINGENIN-7-RHAMNOGLUCOSIDE NARINGENIN-7-RUTINOSIDE AURANTIIN... 

Several investigators have used HPLC to analyze for the individual flavonoids in juices. Fisher and Wheaton (126) used a reverse phase /i-Bondapak C-18 (Waters Associates) column to separate and quantify naringin and naringenin rutinoside. 

Among aglycones, the best known are naringenin and hesperidin. Their glycosylated forms occur commonly as O- or C-glycosides, usually as rutinosides (6-O-a-L-rhamnosyl-D-glucosides) and neohesperidosides (2-O-a-L-rhamnosyl-D-glucosides) attached at position 7. Flavanones contribute to the flavour of citrus [19]. Table 12 reports the structures of some common flavanones. 

Fig. (12). HPLC chromatogram of tomato peel phenolics (1) chlorogenic acid, (2) quercetin 3-rutinoside, and (3) naringenin chalcone. HPLC conditions RP Cjg column (12 x 0.4 cm particle size S pm). Mobile phase acidified water (5% formic acid) and methanol. Gradient 0 min- 10% B, 30 min- 40% B, 40 min- 80% B. Flow rate 1 mL/min.

Figure 6.1. Flavonoids shown to be of nutritional significance are, for the most part, derivatives of either flavone or flavanone, e.g. quercetin (3,3,4,5,7-pentahydroxyflavone), rutin (quercetin-3-rutinoside), naringenin (4,5,7-trihydroxy flavanone), hesperetin (3,5,7-tri-hydroxy-4-methoxyflavanone) and hesperidin (hesperetin-7-rutinoside)...

The main flavonoids which had accumulated in tomato fruits were naringenin and rutin (quercetin-3-rutinoside), predominantly detected in the peel [43, 44]. 

Fig. 51.4 Comparison of flavonoid levels in wild type and transgenic skin of fruit at the red stage of ripening. Naringenin levels (X .290 nm) in the wild type and transgenic skin (of almost three) red uits. Outline of llavonols biosynthesis and profiles of accumulation of rutin and kaempferol-rutinoside (X .370 nm) in skin of transgenic tomatoes compared with those of wild type...

Q, quercetin I, isorhamnetin K, kaempferol L, luteolin N, naringenin H, hesperidin A, apigenin Ac, acacetin D, diosmetin E, eriodictyol Glu, glucoside rut, rutinoside glue, glucuionide gly, glucoside. 

Hesperetin shows cytotoxic effects, at concentrations of 40 and 80 pM, through caspase 3 activation in HL-60 cells and is more cytotoxic than hesperidin. The rutinoside group present at C-7 of hesperidin attenuates the apoptotic cell death in HL-60 cells [52], Naringenin induces apoptosis of KATOIII and MKN-7 gastric cancer cells and HepG2,... 

---