Estrogenic and chemopreventive activities of xanthones and flavones of Syngonanthus (Eriocaulaceae).

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-ß-glucopyranoside, 7=7-methoxyluteolin-6-C-ß-glucopyranoside, 8=7,3'-dimethoxyluteolin-6-C-ß-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.

Flavonoids and a naphthopyranone from Eriocaulon ligulatum and their mutagenic activity.

A new acylated flavonoid, 6,4'-dimethoxyquercetin-3-O-beta-D-6''[3,4,5-trihydroxy (E)-cinnamoyl]glucopyranoside, and a naphthopyranone dimer, named eriocauline, together with 2 other known flavonoids, 6-methoxyapigenin-7-O-beta-D-glucopyranoside and 6-methoxyapigenin-7-O-beta-D-allopyranoside, have been isolated from the capitulae of Eriocaulon ligulatum. The compounds were identified using spectroscopic methods (HR-ESI-MS, and 1-D and 2-D NMR). The methanol extract exhibited mutagenic activity in the Salmonella/microsome assay, in strains TA100, TA97a and TA102 and for dichloromethane extract tested in strain TA98.