Chemical Composition and Evaluation of Antibacterial, Antibiofilm, and Mutagenic Potentials of a Propolis Sample from the Atlantic Forest of Midwest Brazil.

Sixteen triterpenoids with various skeletal types, five phenylpropanoid derivatives, and two flavonoids were isolated from a propolis sample produced by Apis mellifera collected in the Atlantic Forest of Midwest Brazil. Among these compounds, six triterpenes, namely 3ß,20R-dihydroxylanost-24-en-3-yl-palmitate, (23E)-25-methoxycycloartan-23-en-3-one, 24-methylenecycloartenone, epi-lupeol, epi-α-amyrin, and epi-ß-amyrin are being reported for the first time in propolis, while cycloartenone, (E)-cinnamyl benzoate, and (E)-cinnamyl cinnamate are new findings in Brazilian propolis. The presence of cycloartane- and lanostane-type triterpenoids, the latter being a class of compounds of restricted distribution in propolis worldwide, has not been reported in propolis from Midwest Brazil until now. The ethyl acetate phase obtained from the ethanol extract was effective in preventing biofilm formation by Staphylococcus aureus, with an inhibition rate of about 96 % at 0.5 mg.mL-1 , and with quercetin isolated as one of its active constituents. In contrast, the hexane phase exhibited notable antibacterial activity against Pseudomonas aeruginosa, inhibiting bacterial growth by 92 % at 0.5 mg.mL-1 ; however, none of the triterpenoids isolated from this phase proved active against this pathogen. The ethanol extract was neither toxic nor mutagenic at the concentrations tested, as determined by the in vivo SMART assay on Drosophila melanogaster, even under conditions of high metabolic activation.

Anti-hyperglycemic potential and chemical constituents of Aristolochia triangularis Cham. leaves - A medicinal species native to Brazilian forests.

ETHNOPHARMACOLOGICAL RELEVANCE: Aristolochia triangularis Cham. has been used in Brazilian traditional medicine for various therapeutic purposes, including as a leaf-based infusion for diabetes management. AIM OF THE STUDY: This study was designed to chemically characterize an infusion of in natura A. triangularis leaves and evaluate the in vivo anti-hyperglycemic properties of this infusion. MATERIALS AND METHODS: Chemical composition was examined using liquid-liquid extraction procedure, chromatographic methods, NMR, and LC-MS/MS. The in vivo anti-hyperglycemic activity of the freeze-dried infusion of A. triangularis leaves (Inf-L-At) was assessed using oral glucose tolerance test (OGTT). Initially, normoglycemic male rats were pre-treated with orally administered Inf-L-At at doses of 62.5, 125, and 250 mg/kg for two consecutive days. On the day of the OGTT, fasting animals received a glucose load (4 g/kg) 30 min after treatment with Inf-L-At, and the blood glucose levels were verified at 15, 30, 60, and 180 min. Intestinal maltase, lactase, and sucrase activities and muscle and liver glycogen contents were also assessed after the OGTT. RESULTS: Inf-L-At extract led to glycemic reduction with no dose-response at 15, 30, and 60 min comparable to that of the antidiabetic drug glibenclamide and was accompanied by an increase in hepatic and muscle glycogen contents. Additionally, there was a significant statistically decrease in the in vitro activity of disaccharidases. Maltase and sucrase activities were inhibited at all doses, whereas lactase activity was inhibited only at 62.5 and 250 mg/kg. In total, 75 compounds were found in the infusion, including seven new ones, (7S*,8S*,7ꞌS*,8ꞌR*)-4,4ꞌ-dihydroxy-3,3ꞌ-dimethoxy-7,9ꞌ-epoxylignan-7ꞌ-ol; 4ꞌ-hydroxy-3ꞌ-methoxy-3,4-methylenedioxy-7,9ꞌ-epoxylignan-9,7ꞌ-diol; triangularisines A, B, and C; N-ethyl-N-methyl-affineine; and N-methyl pachyconfine, and one previously not described as a natural product, epi-secoisolariciresinol monomethyl ether. CONCLUSION: The results demonstrated the anti-hyperglycemic activity of the infusion from A. triangularis leaves and showed that it is a rich source of lignoids, alkaloids, and glycosylated flavonoids, which are known to exhibit antidiabetic effects and other biological properties that can be beneficial for patients with chronic hyperglycemia, thus certifying the popular use of this herbal drink.

Myricitrin from Combretum lanceolatum Exhibits Inhibitory Effect on DNA-Topoisomerase Type IIα and Protective Effect Against In Vivo Doxorubicin-Induced Mutagenicity.

Flavonoids-compounds abundant in balanced daily diets-have been extensively investigated for biological activity. The pronounced antiproliferative effects of flavonoids have prompted studies to elucidate their mode of action against tumor cells. The anticancer properties of myricetin, a 3',4',5'-tri-hydroxylated flavonol, have been confirmed for a number of neoplasms, but myricitrin, its 3-O-rhamnoside derivative found in fruits and other parts of edible plants, has been scarcely investigated as a chemopreventive agent. This study evaluated the antiproliferative potential of myricitrin obtained from Combretum lanceolatum (Combretaceae) against MCF7 (breast), PC-3 (prostate), HT-29 (colon), 786-0 (kidney), and HL-60 (acute promyelocytic leukemia) cancer cell lines, using the sulforhodamine B and tetrazolium salt assays. Myricitrin proved most effective in inhibiting growth of HL-60 cells (GI50 = 53.4 µmol·L-1), yet showed weak antiproliferative activity against other cell lines. Possible cytotoxic mechanisms involving inhibition of topoisomerases I and IIα by myricitrin were also evaluated, revealing inhibitory activity only against topoisomerase IIα. The results suggested that topoisomerase IIα inhibition is the probable mechanism responsible for the antiproliferative activity of myricitrin. In vivo mutagenicity by myricitrin and its possible antimutagenic effect on doxorubicin-induced DNA damage were also investigated by performing the somatic mutation and recombination test (SMART) on Drosophila melanogaster. Myricitrin proved nonmutagenic to the offspring of standard (ST) and high-bioactivation (HB) crosses, while cotreatments with doxorubicin revealed the antimutagenic properties of myricitrin, even under conditions of high metabolic activation.

Genotoxicity and Antigenotoxicity Assessments of the Flavonoid Vitexin by the Drosophila melanogaster Somatic Mutation and Recombination Test.

Vitexin is a C-glycosylated flavone found in various medicinal plants with several proven biological properties such as anti-inflammatory, antispasmodic, antimicrobial, cytotoxic, and antioxidant activities. Considering that the human population consumes many foods that contain this flavonoid, the objective of this study was to investigate the genotoxic and the antigenotoxic potentials of vitexin by the SMART (Somatic Mutation and Recombination Test) in Drosophila melanogaster wings, in vivo. To evaluate the genotoxic activity, larvae obtained from standard (ST) and high bioactivation (HB) crosses were chronically treated with different concentrations of vitexin (0.15, 0.3, and 0.6 mM). For the evaluation of antigenotoxic activity, the same vitexin concentrations were associated with two damage inducing agents: doxorubicin (0.2 mM) and benzo[a]pyrene (1.0 mM). The results obtained for genotoxic activity showed that vitexin did not induce a statistically significant increment in the frequency of mutant spots, when compared to control. The results for the evaluation of antigenotoxicity indicated that the flavonoid statistically reduced the frequency of mutant spots, when compared to those treated with only the damage inducing agents. Thus, this article presents results that have demonstrated the antigenotoxic activity of vitexin, which could be applied in new studies for the development of drugs with chemoprotective effects.