Biologically active flavonoids from Dodonaea viscosa and their structure–activity relationships
2015
Akhtar, Muhammad | Tel-Cayan, Gülsen | Özturk, Mehmet | Nadeem, Said | Duru, Mehmet E. | Anis, Itrat | Ng, Seik W. | Shah, Muhammad R.
Antioxidant and anticholinesterase activities of twelve flavonoids i.e. santin (1), penduletin (2), viscosine (3), 6,7-dimethylkaempferol (4), kaempferol-3-methylether (5), 3,4′-dimethoxy-5,7-dihydroxyflavone (6), 5,7,4′-trihydroxy-3′-(3-hydroxymethylbutyl)-3,6-dimethoxyflavone (7), 5,7-dihydroxy-3′-(2-hydroxy-3-methyl-3-butenyl)-3,6,4′-trimethoxy-flavone (8), 5,7-dihydroxy-3′-(3-hydroxy-methylbutyl)-3,6,4′-trimethoxyflavone (9), 5,7-dihydroxy-3′-(4′′-acetoxy-3′′-methylbutyl)-3,6,4′-trimethoxy flavone (10), aromadendrin, (2S,3S) 3,4′,5,7-tetrahydroxyflavanone (11), and pinocembrin (12), together with monohydrated crystal (1A) of 1 and anhydrous crystal (3A) of 3 – isolated from Dodonaea viscosa – were studied. The results are given as 50% inhibition concentrations (IC50). Their structure–activity relationships are discussed for both activities. Flavonoids 3 and 10 showed higher antioxidant activity in all tests. 3 Also showed moderate acetylcholinesterase (IC50: 182.97±1.25μM) and significant butyrylcholinesterase (IC50: 47.07±0.54μM) inhibitory activities. Compounds 2 (IC50: 55.78±1.01μM) and 3A (IC50: 58.72±1.02μM) were also moderate anticholinesterase agents against butyrylcholinesterase enzyme. Monohydrate crystal (1A) showed better antioxidant and anticholinesterase activities than its amorphous form (1). In contrast, the amorphous 3 exhibited better activity than the anhydrous crystal (3A). In hydrous crystal, the water molecule might be responsible for better activity. These natural flavonoids can be used as pharmaceuticals and/or preservatives in respective industries.
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