Hesperidine

A mixture of 72 g hesperidin, 288 ml acetic anhydride and 300 ml glacial acetic acid were boiled in reflux with 15 ml pyridine as the catalyst for 144 hours until during the control of the reaction the band disappeared at a wave length between 264 to 280 nm, and a new maximum appeared at 330 nm. Thereafter in a rotation evaporator the reaction mixture was concentrated by evaporation under vacuum conditions. 

After drying at 60°C there was obtained a pure yield of 9.2 g diosmin (65% based upon the employed hesperidin) having a bromine content of 0.07%. 

Several complexes of [Bu2Sn(IV)] with flavonoid glycosides 3-[6-0-(6-deoxy-a-L-mannopyranosyl)-(jS-D-glucopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-H-l-benzopyran-4-one (rutin) and 2, 4, 3-trihydroxy-5, 4-dimetoxychalcone 4-rutinoside (hesperidin) and flavonoid aglycones (quercetin, morin, hesperitin, and other flavones) (Figure 5) were prepared. 

GB 1 494 625 (Unilever appl. 4.2.1974 valid from 4.2.1975). combination with rutin, hesperidin, eriodictin esculoside ... 

Di Manro, A. et al.. Recovery of hesperidin from orange peel by concentration of extract son styrene-divinylbenzene resin, J. Agric. Food Chem., 47, 4391, 1999. 

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). 

Besides being powerful antioxidants, flavonoids are the most important family of phlebotropic drugs. Their properties of vein protection have proved to be of great help in the treatment of venous insufficiency. Daflon 500 mg (Servier Laboratories, France) is a micronized fraction of flavonoids composed of a mixture of diosmin (90%) and hesperidin (10%), which has become one of the preferred medicines for the treatment of chronic venous deficiency. This drug facilitates the contractility of the venous wall,... 

Sakata K, Hirose Y, Qiao Z, Tanaka T and Mori H. 2003. Inhibition of inducible isoforms of cyclooxygenase and nitric oxide synthase by flavonoid hesperidin in mouse macrophage cell line. Cancer Lett 199(2)439-145. 

Fig. 2.45. Gradient elution chromatogram of flavonoids investigated. Peak identification 1 = naringin 2 = hesperidin 3 = quercitrin 4 = myricetin 5 = naringenin 6 = hesperetin 7 = luteolin 8 = apigenin 9 = flavone 10 = acacetin. Reprinted with permission from M. A. Hawryt et al. [136].

Fig. 2.72. Examples of HPLC chromatograms (a) calibration standards (b) commercial orange fruit juice sample (c) hand-sqeezed grapefruit juice sample. Peaks (d) diosmin (h) hesperidin (n) naringin (IS) rhoifolin (internal standard). Reprinted with permission from. F. I. Kanaze et al. [190],...

CONCENTRATIONS OF DIOSMIN. HESPERIDIN. AND NARINGIN IN COMMERCIAL AND HAND-SQUEEZED CITRUS FRUIT JUICE SAMPLES (pG/ML). AND IN TABLETS... 

Citrus fruit juice samples Diosmin (pg/mT) Hesperidin (jug/ml) Naringin (pg/ml)... 

Fig. 2.85. Examples of chromatograms, (a) extract of 1ml blank plasma (b) plasma sample obtained from a female healthy subject 2h after oral administration of a Daflon tablet (diosmin/hesperidin, 450/50 mg) containing 61.2 ng/ml of diosmetin. Peaks I = internal standard, 7-ethoxycoumarin II = diosmetin. Reprinted with permission from F. I. Kanaze el al. [205].

Fig. 2.90. Electropherograms of sterile root exudate before (a) and after incubation with Mesorhizobium loti (b) and Rhizobium leguminosarum bv. trifolii (c). From their UV spectra, peaks 1-6 were identified as resorcinol, rhamnetin, catechin, quercetin glycoside, quercetin aglycone and hesperidin. Differences in the retention times of the same compounds in different samples could be due to the variations in buffer temperature or sample composition. Reprinted with permission from H. L. Steele et al. [213].

T. Guardia, A.E. Rotelli, A.O. Juarez and L.E. Pelzer, Antiinflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjucant arthritis in rat. Framaco 56... 

Fig. 6.1 Biosynthesis of naringin, neohesperidin, narirutin, and hesperidin in Citnis...

Hendrickson R, Kesterson JW (1964) Hesperidin in florida oranges. Univ Fla Exp Stn Bull 684... 

Barthe GA, Jourdan PS, McIntosh CA, Mansell RL (1988) Radioimmunoassay for the quantitative determination of hesperidin in Citrus sinensis. Phytochemistry 27 249-254... 

Heat capacity change, 269 Height equivalent to a theoretical plate. 8 Helium sparge, 188 Hemodialysis, 283 Heptane, 72,76. 173 Heptanoic acid, 260 1-Heptanol, 182, 183 Herbicides, analysis by RPC, 292 Herbicides, chromatography on polar sorbents, 103 Hesperidin, 293... 

Heptane, 3-4-dimethyl Gall Tiss° Hesperidin Dried Lf ... 

Both enantiomers of rhamnose, 6-deoxy-mannose, occur naturally. L-Rhamno-se is a constituent of glycosides such as naringin (89) as well as hesperidin, and a constituent in plant tissues as well as of bacterial cell walls. a-L-Rhamnosida-ses have been employed to debitter fruit juices [145]. 

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. ... 

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