Flavonoids hesperidin

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. 

A rapid HPLC method for the simultaneous determination of the flavonoids hesperidin and naringin and their aglycones (hesperetin and naringenin) in soft drinks, marmalades, candies, yogurts, biscuits, and salad dressings was also developed (153). Samples were refluxed with 60% aqueous methanol at 90°C and chromatographed on a semimicro column and detected at 283 nm by UV. The detection limit for these phenolics was 0.5 /zg/g. 

Paprika was imported to European countries from the Far East such as China and India. The first blossoming of paprika in science was in 1930 when the Nobel Prize winner, Albert Szent-Gyorgyi of Hungary discovered vitamin P (mixture of flavonoids hesperidin and rutin) with the antiscorbutic substance ascorbic acid, vitamin C [1-3]. 

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

Treated citrus penl Citrus peel Flavonoids, hesperidin. sugars Water ... 

Fig. 2.26 A characteristic furocoumaiin (bergamottin), a limonoid (nomilin) and polyphenolic compound (the flavonoid hesperidin) described in grapefruit and the synthetic benzethonium chloride—no chemical relationship. (Authors own work)...

The reduction in signal density and hence overlap made possible the distinction of the flavonoids hesperidin and naringin, that are present in citrus fruits. They occur as diastereoisomers whose proportions depend on the ripeness of the fiuit. Aguilar et al. predicted that the most common 2D NMR experiments could be adapted to decoupling methods of Zangger— Sterk of constant-time type such that pure-shift 2D correlation spectra could be produced. They would be of enormous value in structure elucidation and analyses of mixtures. 

Flavonoids are representative plant polyphenols and commonly recognized as nonnutri-tional dietary components. The diphenylpropane structure with one or more phenolic groups is a characteristic of flavonoids. In 1936, Szent-Gyorgyi first reported that citrus flavonoids (hesperidin and rutin) reduced capillary fragility and permeability in human blood vessels... 

Rosemary is composed of various phenolics such as rosmarinic acid, the flavonoid hesperidin, and the terpenoids camosic acid, camasol, and rosmanol (Al-Sereiti et al. 1999). Rosemary is well known for antioxidant and antimicrobial activity (Naghibi et al. 2005). Multiple extracts and bioactive constituents of rosemary were evaluated for in vitro effect on human cancer cells (Yesil-Celiktas etal. 2010). These included human small cell lung, prostate, liver, breast, and myeloid leukemia, all rosemary extracts and finctionated compounds were toxic to the cell lines at low doses but camosic acid was most effective (Yesil-Celiktas et al. 2010). Bakirel etal. reported in 2007 that ethanol extracts of rosemary reduced blood glucose, and increased insulin levels of rabbits with induced diabetes. They also noted increased levels of the antioxidants SOD and CAT in these animals. 

From citrus flavonoids, hesperidin is the most abundant in lemons, limes, sweet oranges, tangors and tangelos ( 15 mg/100 g edible fruit) [12]. Owing to the importance of hesperidin for food and pharmaceutical industries, several efforts have been made for its extraction and purification. 

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. 

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. 2.45. 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].

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... 

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. ... 

For lemon juice, the flavonoid composition was characterized by HPLC with photodiode detection at 287 nm (108), the HPLC condition based on a procedure proposed by Kirksey et al. (103) for the detection of fruit juice adulteration. Hesperidin and eriocitrin were the characteristic flavonoids of lemon juice. Flavonoid content by HPLC was used to study the effects of processing and pulp removal on flavonoid composition in lemon juice. Eriocitrin is also used in distinguishing lemon juice from grapefruit and orange juices, which do not contain this flavonoid. 

In addition to variations in citrus extracts, there are features of bioflavonoid effects on the mammalian body which may have contributed greatly to the controversy concerning flavonoid action. In 1940 Yosida (13) and in 1955 Rinehart (14) reported effects of hesperidin on rheumatic fever. Yosida determined the erythrocyte sedimentation rate (ESR) before and after injecting hesperidin into patients. In 26 sets of determinations the ESR was retarded in 19, unchanged in 3 and accelerated in 4 cases. Rinehart administered hesperidin to 26 patients, 22 showed a decreased ESR, 1 an unchanged and 3 an increased ESR. Hence, by the usual interpretation that an increased ESR indicates pathology, hesperidin in some cases showed beneficial effects, in others no effect and in still others made the disease worse. 

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