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Food spoilage is a widely neglected problem and the constant use of synthetic fungicides could develop resistant fungi. The objective of this study was to evaluate the chemical composition and antimicrobial activity of Tetradenia riparialeaf essential oil against foodborne disease microorganisms. Leaf essential oil was obtained by hydrodistillation and identified by gas chromatography coupled to mass spectrometry. The antimicrobial activity was studied by broth microdilution. The major compounds identified were oxygenated sesquiterpenes (43.6%): 14-hydroxy-9-epi-(E)-cariophylene (20.8%) and τ-cadinol (18.4%); followed by oxygenated diterpenes (24.6%): 6,7-dehydroroyleanone (12.6%) and 9ß, 13ß-epoxy-7-abiethene (10.6%); sesquiterpenic hydrocarbons (17.1%) and oxygenated monoterpenes (7.4%): fenchone (5.6%). The essential oil had broad antibacterial and antifungal activity, mainly against A. versicolor and P. ochrochloron with fungistatic and fungicidal activities and B. cereus, L. monocytogenes, and S. aureuswith bacteriostatic and bactericidal activities. T. riparialeaf essential oil is a potential alternative to control microorganisms-

El deterioro de los alimentos es un problema ampliamente desatendido y el uso constante de fungicidas sintéticos podría desarrollar hongos resistentes. El objetivo de este estudio fue evaluar la composición química y la actividad antimicrobiana del aceite esencial de hoja de Tetradenia riparia contra microorganismos patógenos transmitidos por los alimentos. El aceite esencial de hoja se obtuvo por hidrodestilación y se identificó mediante cromatografía de gases acoplada a espectrometría de masas. La actividad antimicrobiana estudiada fue por microdilución en caldo. Los compuestos principales del aceite esencial se identificaron como sesquiterpenos oxigenados (43,6%): 14-hidroxi-9-epi-(E)-cariofileno (20,8%) y τ-cadinol (18,4%); seguido de diterpenos oxigenados (24,6%): 6-7-deshidroroileanona (12,6%) y 9ß, 13ß-epoxi-7-abieteno (10,6%); hidrocarburos sesquiterpénicos (17,1%) y monoterpenos oxigenados (7,4%): fenchona (5,6%). Tenía amplia actividad antibacteriana y antifúngica, principalmente contra A. versicolor y P. ochrochloron con actividades fungistáticas y fungicidas, y principalmente contra B. cereus, L. monocytogenes y S. aureus con actividades bacteriostáticas y bactericidas. El aceite esencial de hoja de T. riparia es una alternativa potencial para controlar microorganismos.

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Propolis comprises a complex resinous product composed of plant's parts or exudates, pollen, bee wax, and enzymes. Brazilian brown propolis from Araucaria sp displays several biological activities. Considering the lack of validated analytical methods for its analysis, we are reporting the development of a validated high-performance liquid chromatography with photodiode array detector method to analyze Araucaria brown propolis. The crude propolis were extracted and chromatographed, furnishing six main diterpenes. The isolated standards were used to draw the analytical curves, allowing the studies of selectivity, precision, accuracy, recovery, robustness, the determination of limits of detection and limits of quantification. The mobile phase consisted of 0.1% acetic acid in water and acetonitrile, using an octadecylsilane column, 1 mL/min flow rate and detection at 200 or 241 nm. Relative standard deviation values obtained for intra-day and inter-day precision were lower than 4% for all diterpenes. From the five parameters for robustness, wavelength detection and flow rate were the critical ones. Limits of detection and quantification ranged from 0.808 to 10.359 µg/mL and from 2.448 to 31.392 µg/mL, respectively. The recoveries were between 105.03 and 108.13%, with relative standard deviation values around 5.0%. The developed method is precise, sensitive, and reliable for analyzing Araucaria brown propolis.

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In this work, cashew gum (CG) and gelatin (GE) complexation was explored to encapsulate green coffee oil (GCO), rich in cafestol and kahweol, for use as ingredient in fruit juice. The microcapsules were loaded with 25, 50 and 75% (w/w) GCO and characterized by scanning electron microscopy, encapsulation efficiency and accelerated oxidation by Rancimat. Gas chromatography coupled to the mass detector was used to cafestol quantification in simulated gastrointestinal digestion and during fruit juice storage. Particles with 25% GCO (14.56 ± 6.36 µm) presented good encapsulation efficiency (85.57 ± 1.41%), reduced the GCO oxidation by six-fold and were resisted in the pasteurization conditions. The beverage added of capsules showed good sensory quality when compared to the control formulation. For the first time, the incorporation of GCO capsules into fruit juice has been reported, promoting a diterpene-rich drink with good rheological and sensory properties.

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Jatropha dioica is a popular plant used in Mexican herbal medicine to treat several diseases. Cytotoxicity, antimicrobial and antiviral activities have been reported for root extracts, while riolozatrione, 6-epi-riolozatrione, citlalitrione and jatrophatrione, among others, have been identified as the principal components. In this work, an HPLC/DAD method for the analysis of riolozatrione and other major compounds in extracts of different polarities was validated. The analysis was carried out on an AccQ-Tag column with a water-acetonitrile mixture as mobile phase. Flow rate was 0.2 mL/min, and the separation was carried out in gradient mode with UV detection set at 254 nm. The resulting method showed good reproducibility in both retention times and peak areas of riolozatrione, 6-epi-riolozatrione, citlalitrione and jatrophatrione, with relative standard variations lower than 4.5 and 10.5% respectively. In addition, this method provides a good performance for riolozatrione quantitation, with recoveries between 102 and 108% and RSDs lower than 2.5%. The polarity of the extracting solvent did not affect the performance of the chromatographic method. The developed method was applied for the analysis and quantification of riolozatrione in extracts of Jatropha dioica collected in several seasonal stages and years (2014-2017).

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Abstract Commercial roasted and ground coffees are usually blends of Coffea arabica and Coffea canephora. Considering the differences in price and sensory characteristics between these two species, the identification of the presence of each species in commercial blends is of great interest. The aim of this study was to describe typical profiles of caffeine and diterpenes (kahweol and cafestol) contents and the ratios among these compounds to support the characterization of Coffea species in roasted coffees. 32 good cup quality Brazilian C. arabica coffees (from coffee quality contests) produced using different postharvest treatments were studied. All analysis were performed by HPLC. Higher ranges were observed in diterpene contents - kahweol varied from 1.75 to 10.68 g/kg (coefficient of variation of 510%) and cafestol from 1.76 to 9.66 g/kg (449%) - than caffeine, that varied from 5.1 to 16.2 g/kg (coefficient of variation of 218%). Wide ranges of the kahweol/cafestol ratio (0.63 to 2.77) and the caffeine/kahweol ratio (0.84 to 5.15) were also observed. Hence it was proposed the additional use of a new parameter, the ratio of caffeine/sum of diterpenes (kahweol + cafestol) that presents values from 0.54 to 2.39. The results indicated that the combined use of these parameters could be a potential tool for discriminating Coffea species in blends of roasted and ground coffee. It was proposed as potentially indicative of C. arabica: values of kahweol/cafestol ratio above 0.50, associated with caffeine/kahweol ratio lower than 5.50 and caffeine/sum of diterpenes ratio lower than 2.50.

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This research aimed to correlate the composition of green Arabica coffee beans with the sensory quality coffee brews. The chemical composition of green Arabica coffee bean (66 samples) from three coffee quality contests was analyzed by near-infrared spectroscopy. Coffee brews with lower quality scores were correlated with high levels of caffeine, protein, chlorogenic acids and total titratable acidity (TTA) in the green coffee beans. High sucrose/TTA and cafestol/kahweol ratios in the green coffee beans were usually associated with higher scores for the coffee brews. By multivariate analysis techniques, the samples were separated into groups according to production years indicating a strong influence of the environmental conditions on the chemical composition. The profile of the composition of the crude coffee can be indicative of the sensory quality of the coffee brews, relevant information for producers and industry since the green beans are the material used for trading and purchasing coffee.

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Egletes viscosa (L.) Less (Asteraceae) is a tropical aromatic herb whose flower buds are used for gastrointestinal disorders. Its gastroprotective properties have been attributed to the flavonoid ternatin and the furan diterpenes tanabalin and centipedic acid. The aim of this study was to develop a method of ultra-performance liquid chromatography coupled to electrospray ionization and mass spectrometry (UPLC-ESI-MS) for identifying the constituents from E. viscosa flower buds as well as quantifying its bioactive compounds in herbal products. Infusions and tincture from wild and commercial E. viscosa materials were directly injected on a UPLC-quadrupole-time-of-flight system (UPLC-q-TOF). Afterwards, reference standards were used to quantify ternatin, tanabalin and centipedic acid in these samples, employing a UPLC-single quadrupole system set up for positive mode and Selected Ion Monitoring (SIM). Seventeen compounds were identified, including caffeic acid derivatives, flavonoids and diterpenes, from which seven have been reported for the first time in this specie. The quantification method showed good linearity (R > 0.99), accuracy, precision and sensitivity. The intra-day and inter-day precisions presented relative standard deviations inferior to 6.04 and 8.78%, respectively. The recoveries of all the analytes varied 82.25-117.87%. The limits of detection and quantification ranged between 10-25 µg/L and 25-75 µg/L, respectively. For the samples, the contents of ternatin, tanabalin and centipedic acid ranged from 0.89 to 8.03 mg/L, 0.84-16.8 mg/L and 3.21-16.8 mg/L, respectively. The method demonstrated to be rapid, sensitive and reliable for the quality control of E. viscosa-based products, besides being applicable to other plant extracts containing flavonoids and diterpenes.

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INTRODUCTION: Kaurene diterpenes (KDs) constitute a chemical class often found in the genus Annona with interesting biological activities. To date, chromatographic tools have been mostly used to determine KDs. Quantitative nuclear magnetic resonance (qNMR) has distinguished itself in quantitative estimation of natural products and is an interesting choice to assess total KD contents. OBJECTIVE: To establish a 1 H qNMR method for determining the total KD contents in extracts and fractions obtained from Annona vepretorum stems. METHODOLOGY: Stems were extracted with hexane and methanol, resulting in the hexane extract (HEX-E) and the methanol extract (MeOH-E). The former was partitioned with the acid-base method to obtain the total alkaloid fraction (TA-F) and the neutral dichloromethane fraction (NDM-F). 1 H qNMR measurements were performed on 400 MHz with samples solubilized in deuterated dimethyl sulfoxide. Quantification was carried out using the signals at 4.71 and 4.78 ppm related to hydrogens of the exocyclic double bond of the basic skeleton of KDs and gallic acid as the standard reference. The selectivity, intra- and inter-day precision, reproducibility, limit of detection, limit of quantification, and robustness of the methodology were evaluated. RESULTS: Using the newly developed method, the total KD contents (in µg/mg) were 653.80 ± 12.15 (HEX-E), 458.90 ± 25.94 (NDM-F), 375.60 ± 27.52 (TA-F), and 315.10 ± 19.20 (MeOH-E). For determining the most promising bioactive sample, the KD contents and the sample discriminations obtained by principal component analysis were correlated to the antibacterial activity. Such approach pointed out HEX-E as a potential source of KDs. CONCLUSION: The developed method offers a fast and simple way of determining total KD contents.

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In this study two cultivars of Coffea arabica L., Bourbon (reference) and IPR101 (crossing) were analyzed. The extracts were prepared according to a simplex centroid design with four components, ethanol, ethyl acetate, dichloromethane, and hexane. Multiway data were obtained by HPLC-DAD analysis of the fifteen different mixtures for each cultivar. The PARAFAC methodology was used to investigate the chromatographic fingerprint. For both cultivars, Factor 1 was able to discriminate mixtures containing ethyl acetate as solvent. Factor 2 indicated that mixtures in pure ethanol and binary mixtures containing ethanol were the most efficient in extracting chlorogenic acids and factor 3 identified methylxanthines through spectrophotometric profile in all mixtures. Higher concentrations were obtained by the ethanol, dichloromethane and hexane ternary mixture for the Bourbon cultivar and by the quaternary mixture of these solvents with ethyl acetate for the IPR101 cultivar. Trigonelline and cafestol were extracted in both cultivars. The reference coffee showed higher relative abundances of cafestol ester, chlorogenic acids and trigonelline whereas the crossed coffee showed higher levels of caffeine. To confirm these results, UPLC-MS was used as a complementary method to confirm the presence of the metabolites in these extracts. The three way PARAFAC strategy determines correlations of HPLC-DAD chromatographic and spectral data simultaneously with samples permitting a more unambiguous assignment of metabolic groups than can be obtained treating chromatographic and spectral data separately by two way methods. This can provide higher quality chromatographic fingerprints for food chemistry.

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Copaifera (Leguminoseae) species produce a commercially interesting oleoresin that displays several biological activities, including antimicrobial and anti-inflammatory properties. Labdane-type diterpenes are the main chemical constituents of these oleoresins, and copalic acid is the only compound that has been detected in all Copaifera oleoresins. In this study, we investigate some aspects of the gas-phase fragmentation reactions involved in the formation of the product ions from the deprotonated compounds (-)-ent-copalic acid (1), (-)-ent-3ß-hydroxy-copalic acid (2), (-)-ent-3ß-acetoxy-copalic acid (3), and (-)-ent-agathic acid (4) by electrospray ionization tandem mass spectrometry (ESI-MS/MS) and multiple stage mass spectrometry (MSn ). Our results reveal that the product ion with m/z 99 is common to all the analyzed compounds, whereas the product ion with m/z 217 is diagnostic for compounds 2 and 3. Moreover, only compound 4 undergoes CO2 (44 u) and acetic acid (60 u) elimination from the precursor ion. Thermochemical data obtained by computational chemistry at the B3LYP/6-31G(d) level of theory support the proposed ion structures. These data helped us to identify these compounds in a crude commercial Copaifera langsdorffii oleoresin by selective multiple reaction monitoring (MRM). Finally, a precursor ion scan (PIS) strategy aided screening of labdane-type acid diterpenes other than 1 to 4 in the same Copaifera oleoresin sample and led us to propose the structures of 8,17-dihydro-ent-agathic acid (5) and 3-keto-ent-copalic acid (6), which have not been previously reported in Copaifera oleoresins.

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The results found in the literature concerning the effect of consuming filter coffee brews on increasing the blood cholesterol levels due to the presence of diterpenes, are divergent. Thus the present research evaluated the diterpene (cafestol and kahweol) concentrations in filter coffee brews prepared with paper filters of different sizes, colors and origins (Brazil, Japan, The United States of America, Germany, France and the Netherlands), with and without micro perforations. This is the first study that reports the physical characteristics of paper filter and its importance to obtain filter coffee brew with low cafestol content. Thus, a sample of Catuai cultivar coffee with high cafestol content was roasted to a medium-light degree and used to prepare the brews in a 1:10 ratio (coffee powder to water). The diterpenes were extracted by direct saponification and quantified and identified by HPLC-DAD-MS/MS. The paper filters were physically characterized by measuring their grammage, and the fat permeation rate calculated in order to better understand the differences between the filters which allow one to obtain higher or lower diterpene contents. The cafestol and kahweol concentrations in the brews varied from 1.62 to 2.98 mg/L and from 0.73 to 1.96 mg/L, respectively. The highest cafestol and kahweol concentrations were obtained using paper filters with micro perforations, considering similar sized paper filters. The paper filters showed high fat permeability and grammages between 50.46 and 67.48 g/m2. The diterpene retention capacities of the filters produced in the different countries were similar. The results showed that the porosity of the paper filter and the particle size of the ground roasted coffee were determinant factors in obtaining filter coffee brews with lower cafestol contents.

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Lipids, including the diterpenes cafestol and kahweol, are key compounds that contribute to the quality of coffee beverages. We determined total lipid content and cafestol and kahweol concentrations in green beans and genotyped 107 Coffea arabica accessions, including wild genotypes from the historical FAO collection from Ethiopia. A genome-wide association study was performed to identify genomic regions associated with lipid, cafestol and kahweol contents and cafestol/kahweol ratio. Using the diploid Coffea canephora genome as a reference, we identified 6,696 SNPs. Population structure analyses suggested the presence of two to three groups (K = 2 and K = 3) corresponding to the east and west sides of the Great Rift Valley and an additional group formed by wild accessions collected in western forests. We identified 5 SNPs associated with lipid content, 4 with cafestol, 3 with kahweol and 9 with cafestol/kahweol ratio. Most of these SNPs are located inside or near candidate genes related to metabolic pathways of these chemical compounds in coffee beans. In addition, three trait-associated SNPs showed evidence of directional selection among cultivated and wild coffee accessions. Our results also confirm a great allelic richness in wild accessions from Ethiopia, especially in accessions originating from forests in the west side of the Great Rift Valley.

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Coffee brew presents sensory, stimulatory and antioxidant properties highly appreciated by consumers, despite being associated with an increase in the level of blood cholesterol due to the effects of the diterpenes, especially cafestol, present in the lipid fraction. Although it is believed that the paper filter retains the brew diterpenes, new studies have shown that sometimes coffee filtered through paper can also increase the blood cholesterol level, putting in doubt the efficiency of the paper filter in retaining the diterpenes. Thus the objective of the present study was to verify the distribution of cafestol between the paper filter, the spent coffee and the coffee brew itself, from two coffee samples containing high and low cafestol contents selected from 13 samples of different cultivars and from different locations. In addition, the effect of the roasting degree on the cafestol contents of the roasted coffee was evaluated and the relationship between particle size of the roasted coffee and the extraction of solids. The highest cafestol content was found in the lightly roasted coffee, and the coffee brew presented higher solids contents when the particle size of the coffee powder was below 500µm. The results showed that of the initial cafestol concentration present in the roasted coffee, the paper filter retained 12.41%, the spent coffee 87.45% and the brew 0.15%. Thus, one can conclude that the greater part of the coffee cafestol is retained by the spent coffee, due to the low extraction of the lipid fraction by the hot water.

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Species of Copaifera genus (Fabaceae - Caesalpinoiodidaeae) produces an important commercial oleoresin that displays many medicinal properties. Copaifera oleoresins (COR) are composed mainly of a mixture of diterpenes and sequiterpenes, and the main reported acid diterpenes for this genus are kaurenoic, copalic, hardwickiic and polyaltic acids. An ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method was developed and validated for identification and quantification of nine acid diterpenes. The developed method was applied in the analyses of 10 authentic COR samples collected in the North and Southeast of Brazil and six commercial COR samples. Samples preparation consisted of simple dilution of oleoresins in methanol followed by filtration. Validation parameters of the method for nine acid diterpenes were satisfactory: selectivity/specificity was defined by retention time and MS/MS analyses for each analyte; generally all analytical curves presented r2>0.99, Lack-of-fit test not significant and RSD<20% for all concentration levels; limit of detection and limit of quantification were on the scale of nanogram per milliliter; inter- and intra-day precision and accuracy were adequate. Regarding the robustness, the method was sensible to small deliberate variations of temperature and additives to the mobile phase, such as formic acid and ammonium hydroxide. Results of 16 analyzed samples of COR showed qualitative and quantitative differences of acid diterpenes among all samples. The diterpenes ent-kaurenoic acid 1, ent-polyalthic acid 3, ent-copalic acid 5 and, ent-3-ß-acetoxy copalic acid 9 were found with more frequency in COR analyzed samples. Additionally, the content of the acid diterpenes found in 16 Copaifera oleoresin samples was analyzed by Principal Component Analysis (PCA), suggesting a botanical origin for the commercial samples. The developed UPLC method was shown to be reliable for the analysis of acid diterpenes in commercial Copaifera oleoresins.

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In this study, the temperature and pressure of supercritical CO2 extraction were evaluated to obtain oleoresin of Brunfelsia uniflora leaves and flowers. The oleoresin compounds were identified by gas chromatography-mass spectrometry. The antioxidant activity was evaluated by three different methods. The highest oleoresin yields were 3.32% at 40°C and 200 bar for the leaves, and 1.03% at 60°C and 200 bar for the flowers. The main extracted compounds from leaves were phytol varying from 11.95 to 36.42% and α-tocopherol from 15.53 to 43.10%, and from flowers were geranyl linalool from 11.05 to 21.42% and α-amyrin from 9.66 to 22.12%. Oleoresin obtained at 60°C and 150 bar from leaves presented high antioxidant activity by DPPH (IC50 1.90 mg/mL) and by FRAP (1.8 µmol Fe2+/mg). ß-carotene/linoleic acid co-oxidation oleoresin from leaves at 0.25 mg/mL presented higher antioxidant activity than Trolox. The total phenolic content of the oleoresin from leaves ranged from 66.20 to 83.33 µg/mg and from flowers it was just up to 12.46 µg/mg. The extraction conditions affected yield, chemical composition, and antioxidant activity of oleoresin from leaves and flowers. This is the first report on the antioxidant activity of B. uniflora oleoresin from leaves and flowers and provides subsidies for potential applications in chemical, pharmaceutical, and food industries.

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CONTEXT: Jatropha isabellei Müll. Arg. (Euphorbiaceae) has been used in the traditional medicine to treat arthritis. OBJECTIVE: To evaluate the anti-inflammatory and antinociceptive activities of the dichloromethane fraction (DFJi) from underground parts of J. isabellei, and to develop an analytical method to quantify the diterpene jatrophone. MATERIALS AND METHODS: Anti-inflammatory and antinociceptive activities of the DFji were determined by an acute arthritis model through assessment of the paw elevation time (PET) and articular diameter (AD) of Wistar rats treated orally (50, 100 or 200 mg/kg in a single-dose), and intravenously (0.1, 1, 10, 25 or 50 mg/kg in a bolus administration). The isolation of jatrophone from the DFji was carried out and confirmed by spectroscopic techniques. A UFLC-DAD method was developed and validated. RESULTS: When orally administered, the highest dose (200 mg/kg) of DFJi was able to significantly reduce the PET to 24.8 ± 1.4 s (p < 0.01), when compared with the control group (33.7 ± 1.8 s). The administration of the intravenous dose of 10 mg/kg reduced the PET to 14.8 ± 0.3 s (p < 0.001). The oral and intravenous administration of the DFJi at dose of 200 and 10 mg/kg significantly prevented the formation of edema, reducing the AD in 25.3% and 32.5% (p < 0.01), respectively. The UFLC-DAD method allowed the quantification of jatrophone, which was found to be around 90 µg/mg of fraction. DISCUSSION AND CONCLUSION: The DFJi displayed antinociceptive and antiedematogenic activities, representing a promising plant product for the arthritis treatment.

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Lipids are among the major chemical compounds present in coffee beans, and they affect the flavor and aroma of the coffee beverage. Coffee oil is rich in kaurene diterpene compounds, mainly cafestol (CAF) and kahweol (KAH), which are related to plant defense mechanisms and to nutraceutical and sensorial beverage characteristics. Despite their importance, the final steps of coffee diterpenes biosynthesis remain unknown. To understand the molecular basis of coffee diterpenes biosynthesis, we report the content dynamics of CAF and KAH in several Coffea arabica tissues and the transcriptional analysis of cytochrome P450 genes (P450). We measured CAF and KAH concentrations in leaves, roots, flower buds, flowers and fruit tissues at seven developmental stages (30-240 days after flowering - DAF) using HPLC. Higher CAF levels were detected in flower buds and flowers when compared to fruits. In contrast, KAH concentration increased along fruit development, peaking at 120 DAF. We did not detect CAF or KAH in leaves, and higher amounts of KAH than CAF were detected in roots. Using P450 candidate genes from a coffee EST database, we performed RT-qPCR transcriptional analysis of leaves, flowers and fruits at three developmental stages (90, 120 and 150 DAF). Three P450 genes (CaCYP76C4, CaCYP82C2 and CaCYP74A1) had transcriptional patterns similar to CAF concentration and two P450 genes (CaCYP71A25 and CaCYP701A3) have transcript accumulation similar to KAH concentration. These data warrant further investigation of these P450s as potential candidate genes involved in the final stages of the CAF and KAH biosynthetic pathways.

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The geochemical characterization of petroleum is an essential task to develop new strategies and technologies when analyzing the commercial potential of crude oils for exploitation. Due to the chemical complexity of these samples, the use of modern analytical techniques along with multivariate exploratory data analysis approaches is an interesting strategy to extract relevant geochemical characteristics about the oils. In this work, important geochemical information obtained from crude oils from different production basins were obtained analyzing the maltene fraction of the oils by comprehensive two-dimensional gas chromatography coupled to quadrupole mass spectrometry (GC×GC-QMS), and performing multiway principal component analysis (MPCA) of the chromatographic data. The results showed that four MPC explained 93.57% of the data variance, expressing mainly the differences on the profiles of the saturated hydrocarbon fraction of the oils (C13-C18 and C19-C30n-alkanes and the pristane/phytane ratio). The MPC1 grouped the samples severely biodegraded oils, while the type of the depositional paleoenvironments of the oils and its oxidation conditions (as well as their thermal maturity) could be inferred analysing others relevant MPC. Additionally, considerations about the source of the oil samples was also possible based on the overall distribution of relevant biomarkers such as the phenanthrene derivatives, tri-, tetra- and pentacyclic terpanes.

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Coumarin, o-coumaric, and kaurenoic acid are bioactive compounds usually found in the leaves of Mikania laevigata. Genetic and environmental variations in the secondary metabolites of plants may have implications for their biological effects. Three different accessions of M. laevigata cultivated in four sites between the Equator and the Tropic of Capricorn in Brazil were evaluated aiming to present potential raw materials and discuss relationships among these three bioactive compounds. The results revealed effects of plant accessions and environmental factors and suggested two contrasting chemical phenotypes of M. laevigata. The first phenotype presented the highest levels of kaurenoic acid (2283 ± 316 mg/100 g) besides lower levels of coumarin (716 ± 61 mg/100 g), which was also stimulated by the environment and mild climate at the site nearest to the Tropic of Capricorn. The other phenotype presented the lowest levels of kaurenoic acid (137 ± 17 mg/100 g) besides higher levels of coumarin (1362 ± 108 mg/100 g), which was also stimulated by the environment and tropical climate at the site nearest to the Equatorial beach.

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CONTEXT: The aerial parts of Sphagneticola trilobata (L.) Pruski (Asteraceae) are popularly used to treat topical inflammation, but have not been fully investigated. OBJECTIVE: To identify polar compounds in S. trilobata extracts and develop a new topical phytomedicine based on the kaurenoic acid (KA) content while monitoring and demonstrating its topical anti-inflammatory activity. MATERIALS AND METHODS: Ethanol spray-dried extract of S. trilobata was analysed by LC-MS while the KA content from semisolid was analysed by LC-UV. The extent of ear edema induced by applying 20 µL of croton oil (2.5%), arachidonic acid (AA; 2 mg/ear) and decanoylphorbol-13-acetate (TPA; 2.5 mg/ear) in mice was used to evaluate the biological activity of the semisolids, which were applied 30 min before the phlogistic agents. RESULTS: Eight phenylpropanoids and four oleanane-type triterpenoid saponins were identified, majority of them reported for the first time in this species, in addition to KA. The semisolid containing 1.0% of dried extract reduced the ear edema induced by croton oil [77.2 ± 4.5%; ID50 = 0.49 (0.28-0.87%)], TPA (81.5 ± 2.4%) and AA (39.1 ± 6.9%), with decreasing effect at higher KA concentrations. This was accompanied by neutrophil migration inhibition as investigated by biochemical and histological assays. DISCUSSION AND CONCLUSION: The anti-inflammatory effects were (at least in part) due to the interference in protein kinase C (PKC) activation, AA-cascade products and neutrophil migration inhibition, demonstrating the efficacy of the folk topical usage of this plant. The results support the development of a novel topical anti-inflammatory phytomedicine properly standardized to treat inflammatory dermatological diseases.

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