Flavonoids from Artocarpus anisophyllus and their Bioactivities

Abstract

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-1-picrylhydrazyl) radical scavenging activity with SC 50 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 IC 50 values of 60.5 µg/mL.

The Antioxidant Activity of Prenylflavonoids

“…This is the most abundant class of prenylated flavonoids with antioxidant activity, being a great number of the natural derivatives obtained from different extracts of hops [12][13][14][15][16][17], belonging to the Cannabaceae family. A limited number of derivatives can be obtained from Moraceae [18][19][20], Fabaceae [21][22][23] and Asteraceae [24] families. More than half of the chalcones, mainly derivatives of xanthohumol, were prepared by synthesis [12][13][14][25][26][27][28][29] (compounds 1-44, Table 1).…”

“…Flavone derivatives. The naturally-occurring derivatives were obtained mainly from Moraceae family, belonging to Artocarpus [18,19,21,[30][31][32][33][34][35][36], Dorstenia [20,37] and Cudrania [38,39] species (compounds 47-76, Table 3 [22,40] and Euphorbieaceae [41,42] families were also isolated. Only three analogues were synthesized and were O-prenylated ones (7-O-prenyl-73, 7-O-geranyl-74 and 7-O-farnesylbaicalein 75) ( Table 3 and Figure 6) [43].…”

“…angustone C Azorella madreporica aerial part [53] Xanthone-type compounds. All prenylated xanthone-type derivatives were isolated from different species of Artocarpus: A. altilis [35], A. anisophyllus [18], A. communis [34], A. elasticus [31], A. heterophyllus [12], A. incisa [32], A. integer [36], A. kemando [54], A. nobilis [33], A. obtusus [55], A. scortechinii [19], which belongs to Moraceae family (compounds 131-150, Table 7). In this group we can find compounds with at least four-fused rings which structures may result from the cyclization of the prenyl group in the flavone unit to give a pyran ring ( Figure 10) or can be xanthone nucleus, saturated or not, possessing other rings attached to the main core, leading to compounds with at most six-fused rings ( Figure 11).…”

Prediction of Anti‐Alzheimer's Activity of Flavonoids Targeting Acetylcholinesterase in silico

“…The isolation and characterisation of the flavonoids were achieved by vacuum liquid chromatography (VLC), gravity column chromatography (CC), one-dimensional (1D) and two-dimensional (2D) NMR, FT-IR, UV, MS and by direct comparison with literature data (Lathiff et al, 2015).…”

“…The Artocarpus species are rich in phenolic compounds especially prenylated and pyranoflavonoids with various bioactivities including anti-microbial, antiinflammatory, anti-oxidant, anti-proliferative, anti-cholinergic, AChE inhibitory and tyrosinase inhibitory activities (Arung et al, 2006;Fang, et al, 2008;Lin et al, 2009;Ma et al, 2010;Okoth et al, 2013;Somashekhar et al, 2013). Compound 1 is inactive towards 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radicals, but possesses significant tyrosinase inhibitory activity (Lathiff et al, 2015). In this present work, the bioactivity of the isolated compounds was studied in silico using several screening methods, which include drug likeness, ADME/Tox screening, molecular docking and quantitative structure-activity relationship (QSAR).…”