Antimutagenic Constituents of Casimiroa edulis with Potential Cancer Chemopreventive Activity

Abstract

An ethyl acetate extract derived from the seeds of the medicinal and food plant Casimiroa edulis inhibited mutagenicity induced by 7,12-dimethylbenz[a]anthracene (DMBA) with Salmonella typhimurium strain TM677. It also showed complete inhibition of DMBA-induced preneoplastic lesions with an in vitro mouse mammary gland organ culture system at a concentration of 10 μg/mL. Bioassay-guided phytochemical investigation of this extract using antimutagenicity as a monitor led to the isolation of four furocoumarins, constituted by the known compounds phellopterin (1) and isopimpinellin (2) and the novel compounds (R,S)-5-methoxy-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen (3) and (R,S)-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen (4). Four known alkaloids, casimiroin (5), 4-methoxy-1-methyl-2(1H)-quinolinone (6), 5-hydroxy-1-methyl-2-phenyl-4-quinolone (7), and γ-fagarine (8), and two known flavonoids, zapotin (9) and 5,6,2‘-trimethoxyflavone (10), were also isolated. Of these isolates, compounds 3 and 5 showed the most potent antimutagenic effects in the forward mutagen assay utilizing S. typhimurium strain TM677, whereas casimiroin (5) and 5,6,2‘-trimethoxyflavone (10) significantly inhibited the formation of DMBA-induced preneoplastic lesions in mouse mammary gland organ culture. Keywords: Casimiroa edulis; Rutaceae; furocoumarins; (R,S)-5-methoxy-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen; (R,S)-8-[(6,7-dihydroxy-3,7-dimethyl-2-octenyl)oxy]psoralen; alkaloids; flavonoids; antimutagens; mouse mammary organ culture assay; cancer chemoprevention

Lipophilic flavones of Primula veris L. from field cultivation and in vitro cultures

“…We wish to present the 1 H and 13 C NMR data of the isolated compounds in Tables 1 and 2. Our HSQC and HMBC data for zapotin (1) indicate that previously reported 13 C NMR shifts for C-9 (d C 119.4) and C-10 (d C 149.6) (Ito et al, 1998) need to be interchanged. 2 0 -Hydroxyflavone (3) exhibited B ring protons signals at somewhat different shifts than reported earlier (Blaskó et al, 1988), probably owing to the low concentration of our sample, and exhibited a 2 0 -hydroxyl signal at d H 10.79, not previously reported.…”

“…The remaining compounds were identified by interpretation of their 1 H NMR, 13 C NMR, EIMS and UV spectral data and by comparisons to those available in the literature, as the known flavones -5,6,2 0 ,6 0 -tetramethoxyflavone (zapotin) (1) (Dreyer and Bertelli, 1967;Ito et al, 1998), 2 0 -hydroxyflavone (3) (Blaskó et al, 1988;Wollenweber et al, 1988), 3 0 ,4 0 -dimethoxyflavone (4) (Mabry et al, 1970;Miyake et al, 2003;Ahmed et al, 2003), 3 0 ,4 0 ,5 0 -trimethoxyflavone (5) (Gaydou and Bianchini, 1978;Obrecht, 1989;Iinuma et al, 1992), 2 0 ,5 0 -dimethoxyflavone (7) (Gallagher et al, 1953;Iinuma et al, 1980;Tanaka et al, 1986), 2 0 -methoxyflavone (8) (Freeman et al, 1981;Blaskó et al, 1988), 3 0 -methoxyflavone (9) (Iinuma et al, 1980;Freeman et al, 1981), and flavone (10) (Mabry et al, 1970;Blaskó et al, 1988).…”

Phenolic compounds from leaves of Casimiroa edulis showed adipogenesis activity

“…The structures of compounds 3 and 4 were determined and identified by comparison to previous data as 5,6,2ʹ,3ʹ,5ʹ,6ʹ-hexamethoxyflavone (3) 18) and 5.6.2'-trimethoxyflavone (4), 14,18) respectively. Fig.…”

Estudo em raiz e ráquis foliar de spathelia excelsa: fitoquímica e atividade frente ao fungo Moniliophthora perniciosa associado ao cupuaçuzeiro (Theobroma grandiflorum)

“…Os dados de RMN de 1 H e 13 C permitiram a identificação dos alcaloides folinina e casimiroina (3a,b), 11 em mistura, bem como da casimiroina isolada (3b). Com base nas intensidades dos sinais, da folinina (δ 7,52; 7,06, e 7,01) e da casimiroina (δ 7,46 e 6,71), a folinina é predominante (aprox.…”