Hesperidin Diosmin

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. ... 

Main components Up to 1% essential oil, tannins, flavonoids (hesperidin, diosmin and others), the bitter constituent marrubiin, ursolic and oleanolic acid, a-sitosterol. 

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%. 

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,... 

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].

Buchu leaves Diosmin, hesperidin Reflux with MeOH, filtration C-18 MeOH-H20 HPLC/UV (345 nm) 5 mg/L 30... 

El-Shafae AM and El-Domiaty MM, Improved LC methods for the determination of diosmin and/or hesperidin in plant extracts and pharmaceutical formulations. J Pharm Biomed Anal 26 539-545 (2001). 

Fig. 2 Separation of 25 flavonoid standards (1—eriocitrin 2— neoeriocitrin 3—robinetin 4—narirutin 5—naringin 6— rutin 7— hesperidin 8—neohesperidin 9—isorhoifolin 10— rhoifolin 11—diosmin 12—neodiosmin 13—neoponcirin 14—quercetin 15— poncirin 16—luteolin 17—kaempferol 18—apigenin 19—isorhamnetin 20—diosmetin 21— rhamnetin 22—isosakuranetin 23— sinensetin 24—acacetin 25—tangeretin) using Cig Lichrospher 100, 250 x 4.0 mm, 5 pm, Merck gradient elution with 0.01 M phosphoric acid-methanol with flow rate of 0.6 mL/min at 40°C and detection at 285 nm. (From Ref. [8].)...

There is an obvious connection between crystal chemistry and natural products. Crystals appear in plant material (3,4)—calcium oxalate is extremely common potassium acid tartrate in outer perisperm cells of nutmeg hesperidin and diosmin in cells of many of the Rutaceae calcium carbonate in cells of Cannabinaceae silica in the cells of the sclerenchymatous layer of cardamom seeds. The crystallizing temperature of the solid complex between 1,8-cineoIe and o-cresol forms the basis for official assay of oil of eucalyptus (4). Also worth noting is the fact that alkaloids, particularly brucine, are widely used to resolve optically active acids by diastereoisomer fractional crystallization (5). 

The results presented in table 2 show that when 3-hydroxyl is absent or substituted, its contribution to electron dislocation is substantially reduced and so is consequently the flavonoid antioxidant activity, although this reduction is smaller when this hydroxyl group is substituted (rutin) than when it is absent (diosmin). These results confirm the importance of the 3-hydroxyl group for a better capacity to revert radicals [29, 138, 159, 163], However, the presence of a double bond between C2 and C3 when 3-hydroxyl group is absent (diosmin) does not significantly increase the antioxidant capacity of flavonoids in respect to those that do not present this double bond (hesperidin) in spite of the fact that the double bond should increase the conjugation of the structure according to the aforementioned [139],... 

Another important structural requirement for the antioxidant activity is the number and distribution of hydroxyl groups [163], When just one hydroxyl group is present in B ring (naringenin) the antioxidant activity is strongly reduced when compared with other compounds that have catechol structure or a methoxy substitution (hesperidin), in a similar way as discussed above for rutin and diosmin. This suggests that a lone hydroxyl in the B ring does not contribute at all to the antioxidant activity. 

Lemon Hesperidin, eriocitrin rutin, diosmin 6,8-di-C-glucosyl diosmetin, 6-C-glucosyldiosmetin ... 

Tanaka, T., Modulation of N-methyl-N-amylnitrosamine-induced rat oesophageal tumourigenesis by dietary feeding of diosmin and hesperidin, both alone and in combination. Carcinogenesis, 18,761,1997. 

Agathosma betulina (buchu) contains diosmin (also known as venosmine), a bioflavonoid, and a synthetic form of diosmin is also available. Hidrosmin is 3, 5-di-0-(2-hydroxyethyl)diosmin. Diosmin is marketed as Daflon and Detralex, which contain 90% diosmin plus 10% hesperidin, a flavanone glycoside found in citrus fruits. 

Yang M, Tanaka T, Hirose Y et al (1997) Chemopreventive effects of diosmin and hesperidin on N-butyl-N-(4-hydroxybutyl)nitrosamine-induced urinary-bladder carcinogenesis in male ICR mice. Int J Cancer 73 719-724... 

Tanaka T, MaMta H, Ohnishi H, Mori H, Satoh K, Hara A, Sumida T, Fukntani K, Tanaka T, Ogawa H (1997) Chtanoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis in rats by flavonoids diosmin and hesperidin, each alone and in combinatimi. Cancer Res 57 246... 

A formulation containing 90% diosmin and 10% hesperidin has been used in the treatment of acute hemorrhoids " and chronic venous insufficiency. 

Contains 0.3-2% volatile oil hyssopin (a glucoside) syringoylglycerol glucosides 5-8% tannin flavonoid glycosides (5-6% hesperidin and 3-6% diosmin) sterols and triterpenes ursolic acid, oleanolic acid, stig-masterol, 3-sitosterol marrubiin (a bitter substance, see horehound) a polysaccharide (MAR-10) resin, gum, and others (karrer ... 

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