Flavanones hesperidin

Manach, C., Morand, C., Gil-Izquierdo, A., Bouteloup-Demange, C., and Remesy, C., Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice, Eur. J. Clin. Nutr., 57, 235, 2003. 

Flavanones Hesperidin Naringenin Eriodictyol Taxifolin Fisetin Citrus fruit, orange juice, grapefruitjuice, lemon... 

Flavanones Hesperidin, neohesperidin naringin, and isonaringin. Found mainly in citms fruits, also in tomato cuticles. Antiproliferative effect (73, 75(, Antiatherogenic properties [113], Cardiovascular properties (prevention of platelet aggregation, haemorrhoids, etc) [96,97], 1,500-5,000... 

Flavonoids also showed, to some extent, some antifungal and antiviral activity. In this case, there is an important structure-activity relationship. The flavonol quercetin and the flavanone hesperidin exhibit inhibition activity towards the infective capacity and/or replication of herpes simplex type viruses and polio viruses, while the flavanone naringenin totally lacks this ability [124]. For researchers the impossibility to dissociate, the viruses from the flavonol quercetin after 1 hour of interaction, either by dialysis or ultracentrifugation suggests the formation of quercetin-virus complexes, which may have lost the ability to induce infection. With respect to the antiviral activity of the methoxylated flavones, this is strongly related to a substitution pattern based on... 

Flavanones hesperidin, hesperetin, Naringin Oranges, limes, lemons... 

Cheigh, C.-L Chung, E.-Y. Chung, M.-S. Enhanced extraction of flavanones hesperidin and narirutin from Citrus unshiu peel using subcritical water. J. Food Eng. v. 110, p. 472-477,2012. 

Figure 1.10 Structures of the flavanones hesperidin, neohesperidin and naringin.

The flavanone hesperetin has been detected in citrus honeys but not in honey samples of any other origins (Ferreres et al., 1993). It is a constitutive phenolic compound of citrus nectar, where it is present as a glycoside (hesperidin). 

Different extracts of Citrus were subjected to SPE on Cig cartridges to remove polar components. The retained flavonoids (mainly flavanones) were eluted with methanol-dimethyl sulfoxide, which enhanced solubility of hesperidin, diosmin, and diosmetin. Recoveries of eriocitrin, naringin, hesperidin, and tangeretin from spiked samples of mesocarp tissue exceeded 96%. Flavones were relatively abundant in the leaves. ... 

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. 

The flavanones have received less attention in comparison to flavonols and isoflavones, although their intake from the diet can be high and they exhibit promising biological activity. Little information is available about the absorption or the kinetic behavior of the flavanones naringenin, hesperetin and their glycosylated forms naringin, hesperidin, and narirutin. 

Dilute citrus juice (5 ml) with dimethylformamide (DMF, 10 ml) and 50 mM ammonium oxalate (10 ml), and then steam-bath for 10 min at 90°C. Cooling, adjust the volume to 50 ml with water, centrifuge (10 min at 2500 g), and then filter (Acrodisc, 5 and 0.45 /nm) the clarified juice. For standard preparation, prepare hesperidin (20 ppm) in DMF-water (2 1) solution and other flavanone glycosides (neohesperidin, eriocitrin, neoeriocitrin, naringin, and narirutin, 10 ppm) in the mobile phase. 

Hesperidin Solubility. Hesperidin, a tasteless flavanone glycoside, is the least soluble of all citrus flavonoids. It is found in practically every variety of citrus (5) and is the major flavonoid in sweet oranges and lemons. In fruit or leaves, hesperidin is found as a soluble complex which can be extracted with water or alcohol (5). During juice extraction, the complex is destroyed and hesperTdin slowly precipitates as fine, white, needle-shaped crystals. Once in the solid form, hesperidin can be redissolved in formamide, pyridine or in dilute alkali. 

One of the earliest methods to measure the bitter naringin and other flavanones in grapefruit juice was developed by W. B. Davis in 1947 (12). This test is based on the reaction of dilute alkali with flavanones to form the corresponding yellow chalcones. The flavanone concentration is then determined by measuring the absorbance of the chalcones at 427 nm. Davis pointed out that the procedure was not specific for any flavanone but could be used to determine the principle flavanones in citrus juice, i.e., naringin in grapefruit juice and hesperidin in orange juice. 

Phenolics. The phenolics of citrus represent a varied and widely studied class of compounds. They range from the lipid-soluble methoxylated coumarins and psoralens to the water-soluble glycosides of the flavanones and flavones. They include the intensely bitter naringin and the highly insoluble hesperidin. Different classes within the group have characteristic UV spectra which have been used to detect adulterations in juices and oils. 

The flavonol glycoside rutin (Figure 4.42) from buckwheat (Fagopyrum esculentum Polygo-naceae) and rue (Ruta graveolens Rutaceae), and the flavanone glycoside hesperidin from Citrus... 

Flavanone glycosides hesperidin and naringin are responsible for the bitterness in oranges and grapefruit, respectively. 

Honey contains an extensive diversity of phenolic compounds as secondary constituents, notably flavonoids and phenolic acids (Arraez-Roman et al., 2006 Baltrusaityte et al., 2007 Estevinho et al., 2008). The flavonoid content reaches about 6000 mg/kg, consisting mainly of flavanones and flavones (Anklam, 1998). The main flavonoids are myricetin, tricetin, quercetin, hesperidin, luteolin, kaempferol, pinocembrin, chrysin, pinobanksin,... 

Hesperidin (= 3, 5,7-Trihydroxy-4 -methoxyflavanone-7-rutinoside) (flavanone-O-glycoside) Hyssopus, Mentha (Lamiaceae), Citrus spp., Poncirus trifoliata (Rutaceae) ACE (23% inhibition at 300 pM) [76]... 

Hesperidin (= Ciratin Hesperetin 7-0-Rut 5,7,3, 4 - Tetrahydroxy-flavanone 4 -methyl ether 7-0-Rha-Glc) (flavanone glycoside)... 

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