Intra- and Interspecies Differences of Two Cecropia Species from Tabasco, Mexico, Determined through the Metabolic Analysis and 1H-NMR-Based Fingerprinting of Hydroalcoholic Extracts.

The genus Cecropia is used in the traditional medicine of Tabasco, Mexico, in diabetes and hypertension treatments, mainly without distinction of the species. This contribution aimed to carry out the metabolic analysis and Proton Nuclear Magnetic Resonance (1H-NMR) spectroscopy-based fingerprinting of the hydroalcoholic leaf extracts of Cecropia peltata (Cp) and Cecropia obtusifolia (Co) collected in five sub-regions of the State of Tabasco (Cp1, "Centro"; Cp2, "Chontalpa"; Cp3, "Pantanos"; Cp4, "Ríos" and Co5, "Sierra"). Firstly, the extracts were evaluated for their Total Phenol Content (TPC) and Total Flavonoid Content (TFC) by spectrophotometric methods. In addition, metabolic analysis was performed using High-Performance Liquid Chromatography with Diode-Array Detection HPLC-DAD, which allowed the quantification of the chemical markers: chlorogenic acid, isoorientin, and orientin, as well as a vitexin analog. Finally, metabolomic analysis was carried out based on the 1H-NMR spectra. The Cp4 extract (C. peltata from the "Ríos" sub-region) presented the highest values of TPC (155 ± 9.1 mg GAE/g E) and TFC (724 ± 22.2 mg RE/g E). The metabolic analysis was similar among the five samples; the highest concentrations of the four chemical markers were found in Cp3 (C. peltata from the "Pantanos" sub-region) for chlorogenic acid (39.8 ± 2.3 mg/g) and isoorientin (51.5 ± 2.9 mg/g), in Cp4 for orientin (49.9 ± 0.6 mg/g), and in Cp2 (C. peltata from the "Chontalpa" sub-region) for the vitexin analog (6.2 ± 0.2 mg/g). The metabolic analysis and the 1H-NMR fingerprint analysis showed intraspecies differences among the C. peltata samples and interspecies between C. peltata and C. obtusifolia, which were attributed to variations in the metabolite groups as well as in the proportion of sugars such as glucose and xylose.

Preliminary Phytochemical Profile and Bioactivity of Inga jinicuil Schltdl & Cham. ex G. Don.

Several Mesoamerican cultures have used Inga jinicuil as traditional medicine for the treatment of gastrointestinal, inflammatory, and infectious issues. The aims of this contribution were to elucidate the phytochemical profile of the organic extracts from the bark and leaves of I. jinicuil and to assess the anti-inflammatory and antibacterial properties of these extracts. The preliminary chemical profile was determined by HPLC-PDA and GC-MS; the anti-inflammatory activity was evaluated with a mouse ear edema model, whereas the antibacterial activity was screened against several bacteria. The phytochemical profile of both organs (bark and leaves) of I. jinicuil led to the identification of 42 compounds, such as polyphenolic, flavonoids, triterpenes, prenol-type lipids, and aliphatic and non-aliphatic esters. This molecular diversity gave moderate anti-inflammatory activity (67.3 ± 2.0%, dichloromethane bark extract) and excellent antibacterial activity against Pseudomona aeruginosa and methicillin-resistant Sthaphylococcus aureus (MIC values of ˂3.12 and 50 µg/mL, respectively). These results contribute to the chemotaxonomic characterization and the rational use in traditional medicine of Inga jinicuil Schltdl & Cham. ex G. Don.

Ellagitannin, Phenols, and Flavonoids as Antibacterials from Acalypha arvensis (Euphorbiaceae).

There is a significant need to gain access to new and better antibacterial agents. Acalypha arvensis, a plant from the Euphorbiaceae family, has been used in traditional medicine for centuries to treat infectious diseases. This manuscript reports the isolation, characterization, and antibacterial screening of 8 natural products extracted from maceration of aerial parts of Acalypha arvensis. Specifically, three extracts were assessed (n-hexane, ethyl acetate, and ethanol), in which antibacterial activity was evaluated against diverse bacterial strains. The ethanolic extract showed the best activity against methicillin-sensitive and methicillin-resistant Staphylococcus aureus, Klebsiella pneumoniae, and Pseudomonas aeruginosa strains, which supports the medicinal properties attributed to this plant. The chromatographic fractions AaR4 and AaR5 were the most bioactive, in which the ellagitannin natural product known as corilagin (1) was identified for the first time in this plant. Therefore, it can be said that this is the main chemical responsible for the observed antibacterial activity. However, we also identified chlorogenic acid (2), rutin (3), quercetin-3-O-glucoside (4), caffeic acid (5), among others (6-8). Hence, this plant can be considered to be a good alternative to treat health-related issues caused by various bacteria.

Anxiolytic effect of the heartwood of Haematoxylum campechianum L. and sappanchalcone in an in vivo model in mice.

ETHNOPHARMACOLOGICAL RELEVANCE: Haematoxylum campechianum L., is a well-known plant in the southeast region of Mexico, where it is named as "palo tinto" or "palo de Campeche", in English there are vernacular names such as "redwood", "bloodwood tree" or "campeachy wood". Traditional medicine refers its use for the treatment of different disorders including depression. AIM OF THE STUDY: Considering the traditional use of this plant for the alleviation of depression, the aim of this study was the evaluation of the anxiolytic effect of the methanolic and hydroalcoholic extracts from the heartwood of Haematoxylum campechianum L., and the sappanchalchone (Sapp). Additionally, it is presented the characterization of the new compound 4-hydroxyhematoxylol (2) isolated from the hydroalcoholic extract. MATERIAL AND METHODS: The anxiolytic effect of the extracts and Sapp was evaluated by using the Elevated Plus Maze (EPM) additionally the sedative effect was assessed with the Open Field Test (OFT). The chemical characterization of Sapp and 2 was performing by 1D and 2D NMR experiments. RESULTS: The EPM test showed that the administration of the plant extracts increased the percentage of time spent in open arms (76.32 ± 6.35 and 66.68 ± 20.64%, respectively for the methanolic and hydroalcoholic extracts), whereas the administration of Sapp increased the percentage of time spent in open arms by 60.07 ± 14.28%, these results are similar to Diazepam (DZP, positive control) which caused an increment of 74.06 ± 23.42%. For the OFT, all of the doses evaluated for both extracts and Sapp diminished the number of rearing (R) and total corssing (TC) behavior in a similar way to the positive control (DZO) and statistically different with respect to the vehicle. CONCLUSION: The results obtained showed that the polar extracts from the heartwood of Haematoxylum campechianum L. possess both anxiolytic and sedative effect and that the chalcone-type compound Sapp, isolated from the methanolic extract, is partially responsible of these activities.

Antinociceptive Effect of Hinokinin and Kaurenoic Acid Isolated from Aristolochia odoratissima L.

Aristolochia odoratissima L. is employed for the treatment of pain and as an antidote against the poison of venomous animals in traditional medicine. However, reports have not been found, to our knowledge, about the evaluation of the antinociceptive activity of extracts nor about the presence of compounds associated with this activity. Thus, the purpose of this work was to evaluate the antinociceptive activity of extracts and compounds isolated from the stems of Artistolochia odoratissima L. The extracts were obtained with solvents of increasing polarity and the compounds were isolated and characterized by column chromatography, HPLC, and NMR. The antinociceptive activity was carried out by the formalin test in mice. Ethyl acetate (AoEA) and methanolic (AoM) extracts decreased the paw licking in both phases of the formalin test. The isolated compounds (kaurenoic acid and hinokinin) from AoEA showed the highest antinociceptive activity in both phases of the formalin test. These results confirmed the analgesic effect of this specie described in traditional medicine and provided a base for a novel analgesic agent. They also allowed an approach for the development of standardized plant extracts with isolated metabolites.

Antibacterial activity of Morinda citrifolia Linneo seeds against Methicillin-Resistant Staphylococcus spp.

In traditional medicine, Morinda citrifolia (Noni) is used to treat various ailments, including skin and respiratory-tract infections. In this work, a bio-directed study (seed extracts) with five bacteria was carried out against four clinical isolates of Methicillin-Resistant Staphylococcus (MRS) and Staphylococcus aureus ATCC 29213 strain to find molecules capable of inhibiting them. Three organic extracts were obtained by maceration of the noni seeds with ascending polarity solvents (n-hexane, dichloromethane and methanol) that were evaluated as antibacterial in the model of bioautography and broth microdilution techniques. The results showed that the methanolic extract was the most active against all bacteria (MIC = 16 mg/mL). The chromatographic fractionation performed on this extract allowed obtaining six fractions (EMF1-EMF6), of which F1, F2 and F5 exhibited activity against some of the bacteria. EMF1 fraction reached an MIC of 25 µg/mL against S. haemolyticus twice as much as the positive control, in which the chemical content is mainly composed of a mixture of γ-butyrolactones (1-2) and esterified fatty acids (3-9); chemical characterization of the nine compounds was carried out based on gas chromatography coupled to masses. EMF2 fraction, presented an MIC of 200 µg/mL against S. aureus 0198 and S. haemolyticus 562B, where a coumarin known as scopoletin (10) was isolated and active against S. aureus 0198 (MIC = 100 µg/mL). EMF5 fraction demonstrated an MIC of 200 µg/mL against S. aureus 0198, S. haemolyticus 562B and S. epidermidis 1042, in which a neolignan known as americanin A (11) was identified, showing activity against S. haemolyticus 562B and S. epidermidis 1042 (MIC = 100 µg/mL). The chemical characterization of isolated compounds 10 and 11 was performed by the analysis of 1H and 13C NMR. Therefore, the methanolic extract, identified and isolated compounds showed important antibacterial activity against the MRS, validating its use in traditional medicine.

Sessein and isosessein with anti-inflammatory, antibacterial and antioxidant activity isolated from Salvia sessei Benth.

ETHNOPHARMACOLOGICAL RELEVANCE: Salvia sessei Benth, popularly known as "pipilolxochitl" or "sabanito", is a plant utilized in Mexico in traditional medicine for the treatment of erysipela. To date, only one report, to our knowledge, has been found in which a royleanone-type diterpene of the aerial parts of the species was isolated but, again to our knowledge, studies have not been conducted on the pharmacological activity of extracts and compounds isolated from this plant. AIM OF THE STUDY: The objective of the study was to evaluate the anti-inflammatory, antibacterial and antioxidant activity of the organic extracts of the aerial parts of Salvia sessei Benth and sessein and isosessein isomers isolated from this. MATERIALS AND METHODS: Anti-inflammatory activity was evaluated in a model of edema in mouse ear at 1 mg/ear of the isolated extracts and compounds (1 and 2), a dose-response curve was performed on these latter and one-half of the effective dose (ED50) was determined; antibacterial activity was determined through minimal inhibitory concentration (MIC) by microdilution at 100, 50, 25, and 12.5 µg/mL, and antioxidant capacity, by means of DPPH, ABTS, and FRAP assays where, for the first two assays noted, the inhibitory concentration 50% (IC50) was calculated for the extracts as well as for the compounds isolated. RESULTS: The hexanic extracts (40.55 ±â€¯0.5%), dichloromethanic (56.01 ±â€¯1.1%) and methanolic (66.05 ±â€¯0.3%), as well as isolated compounds 1 (79.85 ±â€¯3.5%) and 2 (54.36 ±â€¯1.7%), demonstrated anti-inflammatory activity; the methanolic extract presented the greatest percentage of inhibition, while isolated compounds 1 and 2 did not present a difference in their ED50; additionally, compound 1 exerted a similar effect to that of the drug-of-reference at the same dose (75.24 ±â€¯2.4%). The antibacterial activity of the extracts and compounds was principally against Gram-positive bacteria: the hexanic extract presented activity against Staphylococcus hominis and the methanolic and dichloromethanic extracts, and compound 1 exhibited activity against Staphylococcus haemolyticus, S. hominis, E. faecalis, in addition to that Escherichia coli was sensitive to compound 1, while isomer 2 showed activity against Staphylococcus aureus, Staphylococcus haemolyticus, Staphylococcus epidermis and Streptococcus pyogenes bacteria related to erysipela. In the three assays, the extract demonstrating greatest antioxidant capacity was the methanolic extract, while that of the isolated compounds was compound 1. CONCLUSIONS: The results show that the three extracts evaluated in the three models presented activity and the chromatographic separation of the dichloromethanic extract permitted the isolation of compounds 1 and 2 royleanone-type isomers, which also presented significant activities such as anti-inflammatory, antibacterial and antioxidant, thus validate the use of this species in traditional medicine.

Homoisoflavonoids and Chalcones Isolated from Haematoxylum campechianum L., with Spasmolytic Activity.

Haematoxylum campechianum is a medicinal plant employed as an astringent to purify the blood and to treat stomach problems such as diarrhea and dysentery. A bio-guided chemical fractionation of the methanolic extract obtained from this plant allowed for the isolation of five compounds: two chalcones known as sappanchalcone (1); 3-deoxysappanchalcone (2); three homoisoflavonoids known as hematoxylol A (3); 4-O-methylhematoxylol (4); and, hematoxin (5). The spasmolytic activity was determined in an in vitro model (electrically induced contractions of guinea pig ileum), and allowed to demonstrate that the methanolic extract (EC50 = 62.11 ± 3.23) fractions HcF7 (EC50 = 61.75 ± 3.55) and HcF9 (EC50 = 125.5 ± 10.65) and compounds 1 (EC50 = 16.06 ± 2.15) and 2 (EC50 = 25.37 ± 3.47) of Haematoxylum campechianum present significant relaxing activity as compared to papaverine (EC50 = 20.08 ± 2.0) as a positive control.

Synthesis and anti-inflammatory activity of three nitro chalcones.

The aim of this study was to synthesize three nitro substituted chalcones and to evaluate their anti-inflammatory activity in the model of carrageenan induced edema in rats. The nitro chalcone were prepared by aldol condensation using of mechanical agitation and environmentally friendly solvents with 72-73% yields in approximately 2h. The three structures were evaluated on biological activity at dose of 200mg/kg and they showed anti-inflammatory protective effect by both oral and intraperitoneal administration, this effect was time dependent.

Second monoclinic form of (E)-3-(4-fluoro-phen-yl)-1-phenyl-prop-2-en-1-one.

The unit-cell dimensions and space group of the second monoclinic polymorph of the title compound, C15H11FO, differ from those of the previously reported form [Jing (2009 ▶). Acta Cryst. E65, o2515]. The title compound shows an E conformation of the C=C bond with the 4-fluoro-phenyl group opposite to the benzoyl group. The torsion angle of between the planes of the 4-fluoro-phenyl and benzoyl groups is 10.53 (6)°. In the crystal, weak C-H⋯O and C-H⋯F inter-actions form a cross-linked packing motif, building sheets parallel to (-102).