Flavonoids from Artocarpus anisophyllus and their bioactivities.
Two new prenylated flavonoids, 4',5-dihydroxy-6,7-(2,2-dimethylpyrano)-2'-methoxy-8-γ,γ-dimethylallylflavone 1 and 3'-hydroxycycloartocarpin 2 along with six known flavonoids, 5,7-dihydroxy-4'-methoxy-8-prenylflavanone 3, isobavachalcone 4, pyranocycloartobiloxanthone A 5, artocarpin 6, chaplashin 7 and cycloartocarpin 8 were isolated for the first time from the leaves and the heartwoods of Artocarpus anisophyllus Miq. The structures of isolated flavonoids were elucidated spectroscopically using 1D and 2D NMR, FTIR, MS, UV and also by comparison with literature data. These flavonoids were screened for their antioxidant and tyrosinase inhibitory activities. The dichloromethane and ethyl acetate crude extracts together with 3'-hydroxycycloartocarpin 2, pyranocycloartobiloxanthone A 5 and artocarpin 6 showed DPPH (2,2-diphenyl-l-picrylhydrazyl) radical scavenging activity with SC50 values of 80.2, 40.0, 152.9, 20.2 and 140.0 μg/mL in 30 min, respectively. Pyranocycloartobiloxanthone A 5 exhibited significant tyrosinase inhibitory activity against tyrosinase from mushroom with IC50 values of 60.5 μg/mL.
Siti Mariam Abdul
SM
Lathiff
Noraini
N
Jemaon
Siti Awanis
SA
Abdullah
Shajarahtunnur
S
Jamil
D031622:Artocarpus / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology*; D016166:Free Radical Scavengers; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000378:metabolism; D010851:Picrates / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D014934:Wood / Q000737:chemistry
D001713:Biphenyl Compounds; D005419:Flavonoids; D016166:Free Radical Scavengers; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl; D014442:Monophenol Monooxygenase