γ-Pyrone Compounds as Potential Anti-cancer Drugs

Abstract

The gamma-pyrones, artomunoxanthotrione epoxide, cyclocommunol, cyclomulberrin, and cyclocommunin exhibited potent inhibition of human PLC/PRF/5 and KB cells in-vitro. Dihydroisocycloartomunin showed significant and potent inhibition of human PLC/PRF/5 and KB cells in-vitro, respectively. Cyclomorusin, dihydrocycloartomunin and artomunoxanthone showed significant inhibition of KB cells in-vitro. Based on the above finding and the reported antileukaemic activity of xanthone psorospermin, a series of natural gamma-pyrones was prepared and the inhibition of human PLC/PRF/5 and KB cells in-vitro was measured. Structure-activity analysis indicated the epoxide group substituted at 3-hydroxyl and 2,6-; 3,6-; and 3,5-dihydroxyl xanthone enhanced the anti-tumour activity. The epoxide group substituted at the 6-hydroxyl group of 1,6-dihydroxyxanthone did not show anti-tumour activity.

Synthesis, biological evaluation, and molecular docking study of 3-(3′-heteroatom substituted-2′-hydroxy-1′-propyloxy) xanthone analogues as novel topoisomerase IIα catalytic inhibitor

“…Anthraquinone analogues, which are structurally similar to xanthones, possess aminoalkoxy substituents (6) and also exhibit enhanced inhibitory activity for topo II-mediated DNA cleavage [9]. These findings may support the possible transition of xanthone substitution from the epoxide to nucleophile-attached chain structures to increase the anti-cancer activity targeting the topoisomerase enzymes.…”

“…The simple structural scaffold and diverse pharmacological properties of xanthone derivatives have prompted many scientists to isolate these compounds from natural resources or synthesize them as novel drug candidates. Among those analogues, epoxy group substituted xanthones (2) exhibited good anti-cancer activity against the cancer cell lines tested [6,7]. Some epoxy xanthones and their ring-opened halohydrin xanthones (3) have shown effective cytotoxicity and topoisomerase type II (topo II) inhibition.…”

“…Xanthones have a diverse biological profile including antihypertensive [2], anticonvulsant [3], anti-thrombotic [4], anticholinesterase [5], and anti-cancer activities [6,7], which depend on their wide range of structures modified by substituents on the xanthone ring. The simple structural scaffold and diverse pharmacological properties of xanthone derivatives have prompted many scientists to isolate these compounds from natural resources or synthesize them as novel drug candidates.…”

Quantitative and qualitative determination of six xanthones in Garcinia mangostana L. by LC–PDA and LC–ESI-MS

“…It contains high amounts of xanthones, a class of polyphenolic compounds. Xanthones have antioxidant [4][5][6][7], antibacterial [8][9][10], antifungal [11], antiinflammatory [3,12,13] antitumor [5,[14][15][16][17][18][19][20][21], antiplatelet aggregation [22], antithrombotic [23] and vasorelaxant activities [24], prevent oxidative damage of LDL [4], histamine and serotonin receptor blockers [25,26], and also inhibit HIV [27]. However, there is no data from clinical trials to verify these effects in humans.…”

Atividade antioxidante de xantonas isoladas de espécies de Leiothrix (Eriocaulaceae)

“…De todas, talvez a mais interessante seja a ação inibitória da enzima monoaminooxidase (MAO), relacionada com o tratamento de estados depressivos; as xantonas apresentaram um grande potencial de utilização por terem demonstrado atividade inibitória potente, seletiva e reversível desta enzima (USDIN, 1984;THULLA et al, 1993;GNERRE et al, 2001). Diversos trabalhos têm apresentado as xantonas como potenciais substâncias para o tratamento do câncer (LIN et al, 1996;ASANO et al 1996;PACHUTA et al, 1986, LIOU et al, 1993PERMANA et al, 1994). Algumas xantonas (naturais e sintéticas) apresentaram, ainda, ação antimicrobiana, inclusive contra Mycobacterium tuberculosis CHAUDHURI, 1975;GHOSAL et al, 1978), ação antifúngica (ROCHA et al, 1994), entre outras.…”