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Flavonoid Overview and Naringin

Flavonoids are naturally occurring phenolic compounds with a diverse range of bioactivities. Approximately 4000 flavonoids have so far been discovered, mainly from fruits, vegetables, and herbs . The basic flavonoid structure consists of 15 carbon atoms, and 3 rings of which 2 are benzene rings connected with a 3-carbon chain . Several types of flavonoids are found in plants, such as flavones, flavanones, flavonols, isoflavones, anthocyanidins, and flavanols . These flavonoids are good scavengers of free radicals and prevent oxidative stress in vivo.

Naringin (with the molecular formula C27H32O14 and a molecular weight of 580.4 g/mol) is a flavanone glycoside found in grapes and citrus fruits . It possesses the distinct bitter taste of grapefruit juice. Two rhamnose units are attached to its aglycon portion, naringenin, at the 7-carbon position. Both naringin and naringenin are strong antioxidants ; however, naringin is less potent compared with naringenin because the sugar moiety in the former causes steric hindrance of the scavenging group. Naringin is moderately soluble in water. The gut microflora breaks down naringin to its aglycon naringenin in the intestine; it is then absorbed from the gut .

Although the average daily human intake of naringin or flavonoids is not known, the total intake of polyphenols was suggested as ∼1 g/d . However, this value is higher than found in some recent findings. Recent evidence suggests that the total daily intake of flavonoids varies among nations and cultures. The consumption of total flavonoids ranges from ∼20 mg/d (United States, Denmark, Finland) to >70 mg/d (The Netherlands) . Chun et al. estimated flavonoid intake by combining the USDA flavonoids database and 24-h dietary recall in NHANES 1999–2002 data. The daily mean intake of flavonoids was found from tea (157 mg), citrus fruit juices (8 mg), wine (4 mg), and citrus fruits (3 mg). Another study, conducted in the Australian population, estimated a flavonoid intake of 128 mg/d from 15 flavonoids except for isoflavones . The ambiguity of a daily intake value for flavonoids is mainly due to the lack of comprehensive food composition data for ≥1 flavonoid subclasses .

There are also very few studies performed with a detailed analysis of the pharmacokinetics of naringin and naringenin. Most of the work reported was mainly conducted in rat models. Naringenin is rapidly metabolized in the liver and converted into glucuronide intermediates . This liver metabolism may limit the bioavailability of naringin in plasma in vivo. It was also reported that a single dose of naringenin and naringin, administered to rats via an i.v. bolus and oral route, rapidly underwent conjugation (glucuronoids and sulfates). The serum concentrations of naringenin and naringin sulfates and glucuronides were found almost exclusively in the bloodstream . Moreover, the concentration of naringenin sulfates was much higher than that of naringenin glucuronides. A number of other studies also reported the presence of naringenin in urine and plasma after an oral dose of naringin or grapefruit juice.

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