Seasonal and circadian variation of non-volatile metabolites in Lippia alba leaves.

The present study describes the seasonal and circadian variations of the major compounds from Lippia alba leaves. SPSS was used to identify, quantify, and associate the variations in the secondary metabolites of this species through HPLC/DAD analysis of the leaves hydroethanolic extracts of six selected L. alba specimens. For the circadian study, the samples were collected at four different daily hours in each year's season. For the seasonal study, the samples were collected monthly from the same individuals for two consecutive years (2018 and 2019). These samples were analyzed and quantified using a validated HPLC method for flavonoids, iridoids, and phenyl ethanoid glycoside. Mussaenoside, acteoside, and tricin-7-O-diglucuronide showed a moderate positive correlation between their biosynthesis and the precipitation index, while epi-loganin had a moderate negative correlation. Acteoside showed a moderate positive correlation between the minimum registered temperature and its production. Compared with previous studies, a drastic reduction (about 95%) in the production of tricin-7-O-diglucuronide compared with previous study and this difference could be attributed to the plant's aging. Thus, the data demonstrated that lower temperatures and high rainfall could favor the production of the major L. alba active compounds (acteoside and tricin-7-O-diglucuronide) and that older plants harm their production.

New dimer and trimer of chalcone derivatives from anti-inflammatory and antinociceptive extracts of Schinopsis brasiliensis roots.

ETHNOPHARMACOLOGY RELEVANCE: Schinopsis brasiliensis Engl. is an endemic tree of the Brazilian semi-arid regions belonging to the Anacardiaceae family. It is the main representative of the genus Schinopsis, mostly native to Brazil and popularly known as "braúna" or "baraúna". Different parts of this plant are employed in Brazilian folk medicines to treat inflammation in general, sexual impotence, cough, and influenza. AIM OF THE STUDY: This work describes the antinociceptive (acetic acid-induced writhing and formalin-induced nociception) and anti-inflammatory (paw edema and neutrophil migration) activities of the extract of the root of S. brasiliensis. Besides, the evaluation of total phenolic compounds and antioxidant, antimicrobial (including MRSA bacteria), and acetylcholinesterase inhibition activities were also determined. MATERIAL AND METHODS: The pure compounds were isolated by different chromatographic techniques and their chemical structures have been unambiguously elucidated based on extensive spectroscopic methods, including 1D (1H, 13C, DEPT, and NOEdiff) and 2D (HSQC, HMBC, and NOESY) NMR experiments, MS data, and comparison with the literature data of similar compounds. The antinociceptive and anti-inflammatory activities were evaluated by acid acetic writhing test, formalin paw edema, and by the investigation of neutrophil migration to the peritoneal cavities of mice. For antimicrobial evaluation were determined MIC and MBC, antioxidant activities were obtained by TPC and DPPH tests, and AChE inhibition by Elmann's methodology. RESULTS: The extracts showed antinociceptive and anti-inflammatory activities and two unusual new compounds, a cyclobutanyl chalcone trimer (schinopsone A) and a cyclohexene-containing chalcone dimer (schinopsone B), with six known compounds were isolated from the active extracts. Additionally, the acetylcholinesterase inhibitory activity for isolated compounds was reported for the first time in this study. Molecular docking studies indicated that the isolated compounds are responsible for the interaction with anti-inflammatory targets (COX 1 and 2 and LOX) with variable binding affinities, indicating a possible mechanism of action of these compounds. CONCLUSIONS: These findings indicate for the first time the correlation between the anti-inflammatory activity different enriched polyphenol-organic soluble fractions of S. brasiliensis, and it contributes to the understanding of the anti-inflammatory potential of S. brasiliensis.

Evaluation of anti-inflammatory, antinociceptive and biological activities of Cenostigma macrophyllum standardized extracts and determination and quantification of the main metabolites.

The stem barks and leaves of Cenostigma macrophyllum are used in Brazilian folk medicines in the treatment of stomach and intestinal diseases. However, there are no reports of chromatographic methods used to evaluate the bioactives of its standardized extracts and for biological evaluation. An analytical method was developed and validated for simultaneous determination and quantification of the bioactive phenolics gallic acid, methyl gallate, ellagic acid and, the biflavonoids agathisflavone and amentoflavone in the leaves and stem bark of C. macrophyllum. HPLC operating conditions were optimized and the parameters such as selectivity, linearity, precision, accuracy, LOD, LOQ and, robustness of the method were also evaluated. Robustness was evaluated using a multivariate optimization technique. Linear relationships within the range of investigated concentrations were observed with their correlation coefficients greater than 0.9991. The method was validated for repeatability (RSD ≤ 2.88%), intermediate precision (RSD ≤ 3.38%) with recovery between 84.12 and 106.64% and the RSD less than 3.40% and proved to be robust. Besides, antioxidant, acetylcholinesterase inhibition, anti-inflammatory and antinociceptive activities of the standardized hydromethanolic extracts of leaves and stem bark of this species were evaluated. The method was successfully applied in the quantification of the gallic acid, methyl gallate, ellagic acid, agathisflavone and amentoflavone of standardized extracts. The results showed the present method developed was simple, sensitive, reproducible, accurate and precise. The standardized hydromethanolic extracts of leaves and stem bark of C. macrophyllum showed antioxidant activity (EC50 69.09 and 83.06 µg mL-1), acetylcholinesterase inhibition (52.23 and 83.36%) and they were able to inhibit the formalin-induced nociception and also reduced the edema formations at 100 mg kg-1 doses. The anti-inflammatory potentials were evaluated by the decrease of the Cg-induced neutrophils migrations at the same doses.

Toxicidade de extratos de Piper nigrum, piperina e piperamidas para o diplópodo Orthoporus fuscipes em condições de laboratório / Toxicity of extracts from Piper nigrum, piperine and piperamides to the millipede Orthoporus fuscipes under laboratory conditions

The toxicity of an ethanolic extract of black pepper (Piper nigrum), of piperine and of the synthetic amides adamantylpiperamide, sopentylpiperamide and diisopropylpiperamide was evaluated using the millipede Orthoporus fuscipes. For the experiments, the test organism was exposed to a diet of wheat bran and sugar (9:1) supplemented with the test substance in solution and mortality was monitored over a period of 17 days. Mortality was 100 percent for 0.3 g of the ethanolic extract of black pepper fruits and for diisopropylpiperamide after 4 and 14 days of exposure, respectively. Piperine at a concentration of 0.3 g resulted in 70 percent mortality after 4 days and remained at this rate until the end of the exposure period. Thus, among the compounds tested the ethanolic extract of black pepper fruit was the most effective and most promising for the control of Orthoporus fuscipes populations since it promoted a higher rate of mortality of the test organism within a shorter period of exposure.

A toxicidade do extrato etanólico da pimenta-do-reino (Piper nigrum), da piperina e amidas sintéticas: adamantilpiperamida, isopentilpiperamida e diisopropilpiperamida foi avaliada para o diplópodo Orthoporus fuscipes. Os experimentos consistiram na exposição dos organismos-teste a uma dieta de farelo de trigo e açúcar (9:1) a qual foi adicionada a substância teste em solução observando-se a mortalidade por um período de 17 dias. Verificou-se na dose contendo 0,3 g do extrato etanólico de frutos da pimenta-do-reino e da diisopropilpiperamida, 100 por cento de mortalidade após 04 e 14 dias de exposição, respectivamente. A piperina na concentração de 0,3 g causou 70 por cento de mortalidade após 4 dias, mantendo-se até o final do período de exposição. Dessa forma, dentre os compostos testados, o extrato etanólico do fruto da pimenta-do-reino foi considerado o mais eficiente e promissor no controle de populações de Orthoporus fuscipes, pois foi o que promoveu maior porcentagem de exposição.