TY - JOUR T1 - Estrogenic and chemopreventive activities of xanthones and flavones of Syngonanthus (Eriocaulaceae). AU - de Oliveira,Ana Paula Siqueira, AU - de Sousa,Juliana Ferreira, AU - da Silva,Marcelo Aparecido, AU - Hilário,Felipe, AU - Resende,Flávia Aparecida, AU - de Camargo,Mariana Santoro, AU - Vilegas,Wagner, AU - dos Santos,Lourdes Campaner, AU - Varanda,Eliana Aparecida, Y1 - 2013/07/25/ PY - 2013/03/05/received PY - 2013/07/12/revised PY - 2013/07/16/accepted PY - 2013/7/30/entrez PY - 2013/7/31/pubmed PY - 2014/4/18/medline KW - +S9 KW - 1 KW - 1,3,6,8-tetrahydroxy-2,5-dimethoxyxanthone KW - 1,3,6,8-tetrahydroxy-5-methoxyxanthone KW - 1,5,7-trihydroxy-3,6-dimethoxyxanthone KW - 17β-estradiol KW - 2 KW - 3 KW - 4 KW - 4-nitro-O-phenylenediamine, B[a]P, benzo[a]pyrene KW - 5 KW - 6 KW - 6-hydroxyluteolin KW - 7 KW - 7,3′-dimethoxyluteolin-6-C-β-glucopyranoside KW - 7-methoxyluteolin-6-C-β-glucopyranoside KW - 7-methoxyluteolin-8-C-β-glucopyranoside KW - 8 KW - 9 KW - AFB(1) KW - Antimutagenicity KW - BAW KW - CNPq KW - Conselho Nacional de Desenvolvimento Científico e Tecnológico KW - DES KW - DMSO KW - E(2) KW - EEQ KW - ER KW - ER-RBA KW - Eriocaulaceae KW - Estrogenicity KW - Ex-DCM KW - Ex-Hex KW - Ex-MeOH KW - FAPESP KW - Fundação de Amparo à Pesquisa do Estado de São Paulo KW - HRT KW - HSCCC KW - I% KW - MI KW - Mutagenicity KW - NPD KW - Phytoestrogens KW - RYA KW - SA KW - SD KW - SERMs KW - Sd KW - Sm KW - Sn KW - Ss KW - Standard Deviation KW - UV KW - aflatoxin B(1) KW - dimethylsulfoxide KW - estradiol equivalent KW - estrogen diethylstilbestrol KW - estrogen receptor KW - estrogen receptor relative binding affinity KW - hexane extract KW - high speed counter current chromatography KW - hormone replacement therapy KW - luteolin KW - methanol extract KW - methanolic extract of capitula of Syngonanthus dealbatus KW - methanolic extract of capitula of Syngonanthus macrolepsis KW - methanolic extract of capitula of Syngonanthus nitens KW - methanolic extract of capitula of Syngonanthus suberosus KW - methylene chloride extract KW - mix of A-1,3,6-trihydroxy-2-methoxyxanthone and B-1,3,6-trihydroxy-2,5-dimethoxyxanthone KW - mutagenic index KW - n-butanol, acetic acid and water solution KW - percent of inhibition of reversion in bacterial strains KW - recombinant yeast assay KW - selective estrogen receptor modulators KW - sodium azide, 2-AA, 2-anthramine, MMC, mitomycin C KW - ultraviolet light KW - with metabolization KW - without metabolization KW - −S9 SP - 1053 EP - 63 JF - Steroids JO - Steroids VL - 78 IS - 11 N2 - The possible benefits of some bioactive flavones and xanthones present in plants of the genus Syngonanthus prompted us to screen them for estrogenic activity. However, scientific research has shown that such substances may have undesirable properties, such as mutagenicity, carcinogenicity and toxicity, which restrict their use as therapeutic agents. Hence, the aim of this study was to assess the estrogenicity and mutagenic and antimutagenic properties. We used recombinant yeast assay (RYA), with the strain BY4741 of Saccharomyces cerevisiae, and Ames test, with strains TA100, TA98, TA97a and TA102 of Salmonella typhimirium, to evaluate estrogenicity, mutagenicity and antimutagenicity of methanolic extracts of Syngonanthus dealbatus (S.d.), Syngonanthus macrolepsis (S.m.), Syngonanthus nitens (S.n.) and Syngonanthus suberosus (S.s.), and of 9 compounds isolated from them (1=luteolin, 2=mix of A-1,3,6-trihydroxy-2-methoxyxanthone and B-1,3,6-trihydroxy-2,5-dimethoxyxanthone, 3=1,5,7-trihydroxy-3,6-dimethoxyxanthone, 4=1,3,6,8-tetrahydroxy-2,5-dimethoxyxanthone, 5=1,3,6,8-tetrahydroxy-5-methoxyxanthone, 6=7-methoxyluteolin-8-C-β-glucopyranoside, 7=7-methoxyluteolin-6-C-β-glucopyranoside, 8=7,3'-dimethoxyluteolin-6-C-β-glucopyranoside and 9=6-hydroxyluteolin). The results indicated the estrogenic potential of the S. nitens methanol extract and four of its isolated xanthones, which exhibited, respectively, 14.74±1.63 nM; 19.54±6.61; 7.20±0.37; 6.71±1.02 e 10.01±4.26 nM of estradiol-equivalents (EEQ). None of the extracts or isolated compounds showed mutagenicity in any of the test strains and all of them showed antimutagenic potential, in particular preventing mutations caused by aflatoxin B1 (AFB1) and benzo[a]pyrene (B[a]P). The results show that the xanthones, only isolated from the methanol extract of S. nitens capitula, probably were the responsible for its estrogenic activity and could be useful as phytoestrogens, providing a new opportunity to develop hormonal agents. In addition, flavones and xanthones could also be used as a new antimutagenic agent. Since, the mutagens are involved in the initiation and promotion of several human diseases, including cancer, the significance of novel bioactive phytocompounds in counteracting these pro-mutagenic and carcinogenic effects is now gaining credence. SN - 1878-5867 UR - https://www.unboundmedicine.com/medline/citation/23891669/Estrogenic_and_chemopreventive_activities_of_xanthones_and_flavones_of_Syngonanthus__Eriocaulaceae__ DB - PRIME DP - Unbound Medicine ER -