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Zastosowanie kwercetyny, moryny i ich sulfonowych pochodnych w terapii i przemyśle spożywczym

Kopacz M., Kuźniar A.

Wiadomości Chemiczne

2005

[Z] 59, 7-8

723--735

Flavonoids (derivatives of 2-phenylo-y-benzopyrone) are a large group of biologically active plant products. As a common component of daily nutrition, flavonoids can modulate many biological processes. Therapeutic properties of flavonoids have been well known for many years. Originally, the object of interest was medicinal plants. The papers by Szent-Gyorgy in the thirties of the 20-th century aroused interest in flavonoids. Szent-Gyorgy revealed that a lemon compound belonging to flavonoids - hesperidin has a synergic effect with Vitamin C and prevents scurvy. Quercetin (3,5,7,3',4'-pentahydroxyflavone) and morin (3,5,7,2',4'-pentahydroxyflavone), Fig. 1, are the most widespread flavonoids. Due to their properties these compounds find application in therapy as viral antigens, bactericide and antitumor agents. Owing to a convenient position of oxygen in the 5C-OH and 4C=O as well as 3C-OH and 4C=O groups, morin and quercetin form chelate complexes with ions of p-, d- and f-electron metals. Some researchers think, that biological activity of flavonoids is connected with their complexation capacity. Therapeutic action can show both the molecule and its metabolite. The application of quercetin and morin is restricted due to their insolubility in water. Their sulfonic derivatives are well soluble in water and show biological activity as their mother compounds. Therefore, the latter can be more useful for therapy purposes.

Sulfonowe pochodne niektórych flawonoidów i ich właściwości

Kopacz M., Nowak D.

Wiadomości Chemiczne

2004

[Z] 58, 7-8

661--670

Flavonoids belong to a large group of natural compounds of substantial biological activity. Some examples are rutin and hesperidin which are widely used in medical treatment. Recent growing interest in these compounds comes of their possible application as natural antioxidant protecting against harmful action of free radicals. Moreover, flavonols could complex metal cations and some of them are used as analytical reagents [6-8]. The major reason for limited application of flavonoids is their weak solubility in water. Sulfonic derivatives of flavonoids due to the presence of sulfonic group in the molecule are well soluble in water. They form complexes with metal ions like their mother compounds and the complexation range is significantly wider than bioflavonoids. It in proposed to use quercetin-5'-sulfonic acid (QSA) (1) and sodium salt of morin-5'-sulfonic acid (NaMSA) (6) as new reagents in spectrophotometric determination of metals [18, 19]. Some of the compounds of Al, Ga and In with quercetin-5'-sulfonic acid and sodium salt of morin-5'-sulfonic acid show strong luminescence and for this reason can be used in laser technology. It has been found that sulfonic derivatives of quercetin could be an effective antidote against heavy metals - Hg(II), Cd, Pb(II) and as reported [37, 38] sodium salt of quercetin-5'-sulfonic acid (2) is a particularly active one. Sulfonic derivatives of quercetin, morin and chrysin, exhibit also the activity in different biological systems. It is supposed that sulfonic derivatives of flavonoids could have greater practical application than their mother compounds.