Novel Study on Chemical Characterization and Antimicrobial, Antioxidant, and Anticholinesterase Activity of Essential Oil from Ecuadorian Bryophyte Syzygiella rubricaulis (Nees) Stephani.

Our research focuses on exploring the chemical composition and some biological properties of the essential oil derived from Syzygiella rubricaulis (Nees) Stephani, a bryophyte species. To conduct a comprehensive analysis, we utilized a DB5MS capillary column along with gas chromatography coupled to mass spectrometry (GC-MS) and flame ionization (GC-FID). The qualitative and quantitative examination revealed the presence of 50 compounds, with hydrocarbon sesquiterpenes (48.35%) and oxygenated sesquiterpenes (46.89%) being the predominant constituents. Noteworthy compounds identified include bicyclogermacrene (12.004%), cedranone <5-> (9.034%), spathulenol (6.835%), viridiflorol (6.334%), silphiperfol-5,7(14)-diene (6.216%), biotol <ß-> (6.075%), guaiol (4.607%), viridiflorene (4.65%), and α-guaienol (3.883%). Furthermore, we assessed the antimicrobial, antioxidant, and anticholinesterase activity of the essential oil, revealing a compelling inhibitory effect against acetylcholinesterase (AChE) with an IC50 value of 26.75 ± 1.03 µg/mL and a moderate antimicrobial (MIC 500 µg/mL, Enterococcus faecium, Lysteria monocytogenes) and antioxidant effect (ABTS: SC50 343.38 and DPPH 2650.23 µg/mL). These findings suggest the potential therapeutic application of the bryophyte essential oil in the treatment of Alzheimer's disease due to its potent anticholinesterase properties.

A Study of the Essential Oil Isolated from Ageratina dendroides (Spreng.) R.M. King & H. Rob.: Chemical Composition, Enantiomeric Distribution, and Antimicrobial, Antioxidant, and Anticholinesterase Activities.

Ageratina dendroides is an aromatic species native to Ecuador. In this study, the chemical composition, enantiomeric distribution, and antifungal, antibacterial, antioxidant, and anticholinesterase activities of the essential oil isolated from aerial parts of Ageratina dendroides were determined. The quantitative chemical composition was determined using gas chromatography equipped with a flame ionization detector. The qualitative chemical composition was determined using gas chromatography coupled with mass spectrometry. The enantiomeric distribution was determined using an enantioselective chromatographic column. A broth microdilution method was used to determine the antibacterial activity. This antibacterial activity was tested against three Gram-negative bacilli bacteria and three Gram-positive cocci bacteria. The antifungal activity was tested against two fungi, a fungus, and a yeast. The antioxidant activity was determined using the ABTS (2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)) method and DPPH (2,2-diphenyl-1-picrylhydrazyl) method. The anticholinesterase activity was analyzed using the spectrophotometric method. Sixty-eight volatile compounds were identified in the essential oil. These compounds represent 99.49% of the total composition. In terms of the number of compounds and their relative abundance, the most representative group was sesquiterpene hydrocarbons, with thirty-four compounds and an abundance of 49.22%. The main constituents were found to be andro encecalinol (14.41 ± 1.26%), germacrene D (8.86 ± 1.06%), amorpha-4,9-dien-14-al (7.68 ± 0.70%), ß-sesquiphellandrene (7.01 ± 1.49%), α-muurolol (5.89 ± 0.93%), and 7-epi-α-selinene (5.68 ± 0.53%). Five pairs of enantiomers were identified in the essential oil of Ageratina dendroides. The essential oil did not report antimicrobial activity at the maximum concentration tested (MIC > 4000 µg/mL) against any of the microorganisms tested. The antioxidant activity of the essential oil was strong in the ABTS method, with an SC50 of 33.2 ± 1.4 µg/mL. Additionally, the Ageratina dendroides essential oil reported moderate anticholinesterase activity, with an IC50 of 297.8 ± 1.03 µg/mL.

Chemical Constituents, Enantiomer Content, Antioxidant and Anticholinesterase Activities of Valeriana microphylla Kunth Essential Oil.

The study of the essential oil (EO) from aerial parts (stems and leaves) of Valeriana microphylla Kunth (Valerianaceae), collected from the Saraguro community in the southern region of Ecuador, was analyzed for the first time. A total of 62 compounds were identified in V. microphylla EO by GC-FID and GC-MS on nonpolar DB-5ms and polar HP-INNOWax columns. The most abundant components (>5%) detected on DB-5ms and polar HP-INNOWax columns were α-gurjunene (11.98, 12.74%), germacrene D (11.47, 14.93%), E-caryophyllene (7.05, 7.78%), and α-copaene (6.76, 6.91%), respectively. In addition, the enantioselective analysis, carried out on a chiral column, showed (+)-α-pinene and (R)-(+)-germacrene as enantiomerically pure compounds (enantiomeric excess = 100%). The antioxidant activity was high for the radicals ABTS (SC50 = 41.82 µg/mL) and DPPH (SC50 = 89.60 µg/mL), and finally, the EO was shown to be inactive to the enzyme acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), as both values were >250 µg/mL.

Chemical Composition, Enantiomeric Distribution and Biological Activity of Essential Oil from Morella pubescens (Humb. & Bonpl. ex Willd.) Wilbur.

The species Morella pubescens, commonly known as wax laurel, is a tree belonging to the Myricaceae family that can be found from Costa Rica to Bolivia. In this study, the chemical composition, enantiomeric distribution, and biological activity of essential oil isolated from the leaves of this species was determined. Hydrodistillation was used to isolate the essential oil (EO). Gas chromatography coupled with mass spectrometry was used to determine the qualitative composition, gas chromatography equipped with a flame ionization detector was used to determine quantitative composition, and gas chromatography on an enantioselective column was used to determine enantiomeric distribution. The broth microdilution method was employed to assess the antibacterial capacity of the essential oil against seven opportunistic microorganisms, including three Gram-positive cocci bacteria, a Gram-positive bacilli bacterium and three Gram-negative bacilli bacteria. 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid radical cation and 2,2-diphenyl-1-picrylhydryl free radical were used as reagents to determine the antioxidant activity of essential oil. The spectrophotometric method was used to analyze the acetylcholinesterase inhibitory effect of the essential oil. The extraction method afforded a low yield of around 0.076 ± 0.008% (v/w). Fifty-eight chemical compounds, which represent 97.9% of the total composition, were identified in the essential oil. Sesquiterpene hydrocarbons were the most representative group with 24 compounds (67.8%). The principal constituents were (E)-caryophyllene (27.5 ± 1.3%), limonene (11.8 ± 0.6%), δ-selinene (9.1 ± 0.2%), ß-selinene (8.0 ± 0.2%), selina-3,7(11)-diene (5.3 ± 0.2%) and germacrene B (5.0 ± 0.5%). Three pairs of enantiomers were identified in the essential oil of Morella pubescens. Essential oil presented strong activity against the bacterium Enterococcus faecium (ATCC 27270) with an MIC of 250 µg/mL. The antioxidant activity of essential oil was very strong in the ABTS method with an SC50 of 46.4 ± 1.0 µg/mL and was strong in the DPPH method with an SC50 of 237.1 ± 1.8 µg/mL. Additionally, the essential oil reported strong anticholinesterase activity with an IC50 of 133.5 ± 1.06 µg/mL.

Study of the Chemical Composition and Biological Activity of the Essential Oil from Congona (Peperomia inaequalifolia Ruiz and Pav.).

The species Peperomia inaequalifolia, commonly known as congona, is a succulent herbaceous plant belonging to the Piperaceae family, which is used for different purposes in traditional medicine. In this study, the chemical composition, enantiomeric distribution, and biological activity of essential oil isolated from the leaves of this species was determined. Hydrodistillation was used to isolate the essential oil. Gas chromatography coupled to mass spectrometry was used to determine the qualitative composition, a gas chromatograph equipped with a flame ionization detector was used to determine quantitative composition, and gas chromatography on an enantioselective column was used to determine enantiomeric distribution. Antibacterial activity was determined using the broth microdilution method, for which we used three Gram-positive cocci bacteria, a Gram-positive bacilli bacterium, and three Gram-negative bacilli bacteria. 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical cations and 2,2-diphenyl-1-picrylhydryl (DPPH) radicals were used as reagents for determining the antioxidant activity of the essential oil. The spectrophotometric method was used to analyze the acetylcholinesterase inhibitory effect of the essential oil. The yield of leaves in essential oil was 0.16 ± 0.01% (v/w). Forty-three chemical compounds were identified in the essential oil, which represent 97.46% of the total composition. Sesquiterpene hydrocarbons were the most representative group, with 24 compounds (21.63%). The principal constituents were found to be elemicin (27.44 ± 1.35%), bisabolol <α-> (17.76 ± 1.38), myristicin (15.45 ± 0.86), methyl eugenol (6.22 ± 0.24), viridiflorene (6.81 ± 0.10), and safrole (6.68 ± 0.23). Three pairs of enantiomers were identified in the essential oil of Peperomia inaequalifolia. Essential oil presented a minimum inhibitory concentration (MIC) of 4000 µg/mL against Enterococcus faecalis, Enterococcus faecium, Staphylococcus aureus, Listeria monocytogenes, and Escherichia coli. The antioxidant activity of the essential oil was strong according to the DPPH and ABTS methods, with a half radical scavenging capacity (SC50) of 293.76 ± 3.12 µg/mL and 226.86 ± 0.05 µg/mL, respectively. Additionally, the essential oil reported moderate anticholinesterase activity, with an IC50 of 43.93 ± 1.05 µg/mL.

Chemical Profiling, Anticholinesterase, Antioxidant, and Antibacterial Potential of the Essential Oil from Myrcianthes discolor (Kunth) McVaugh, an Aromatic Tree from Southern Ecuador.

Myrcianthes discolor, an aromatic native tree from southern Ecuador, was collected to determine the chemical composition and the biological activity of its essential oil (EO). The EO was obtained by steam-distillation and analyzed by gas chromatography coupled to a mass and a FID detector (GC-MS and GC-FID) and a non-polar DB5-MS column. Enantioselective GC-MS analysis was performed in a chiral capillary column. The antimicrobial, antioxidant, and anticholinesterase potency of the EO was carried out by the broth microdilution method, radical scavenging assays using 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, and by measuring the inhibition of the acetylcholinesterase (AChE) enzyme. A total of 58 chemical compounds were identified, corresponding to 94.80% of the EO composition. Sesquiterpenes hydrocarbons represented more than 75% of the composition. The main compounds detected were E-caryophyllene with 29.40 ± 0.21%, bicyclogermacrene with 7.45 ± 0.16%, ß-elemene with 6.93 ± 0.499%, α-cubebene with 6.06 ± 0.053%, α-humulene with 3.96 ± 0.023%, and δ-cadinene with 3.02 ± 0.002%. The enantiomeric analysis revealed the occurrence of two pairs of pure enantiomers, (-)-ß-pinene and (-)-α-phellandrene. The EO exerted a strong inhibitory effect against AChE with an IC50 value of 6.68 ± 1.07 µg/mL and a moderate antiradical effect with a SC50 value of 144.93 ± 0.17 µg/mL for the ABTS radical and a weak or null effect for DPPH (3599.6 ± 0.32 µg/mL). In addition, a strong antibacterial effect against Enterococcus faecium was observed with a MIC of 62.5 µg/mL and Enterococcus faecalis with a MIC of 125 µg/mL. To the best of our knowledge, this is the first report of the chemical composition and biological profile of the EO of M. discolor, and its strong inhibitory effect over AChE and against two Gram-positive pathogenic bacteria, which encourage us to propose further studies to validate its pharmacological potential.

Study of Essential Oil Isolated from Achiote (Bixa orellana) Leaves: Chemical Composition, Enantiomeric Distribution and Antimicrobial, Antioxidant and Anticholinesterase Activities.

Bixa orellana is a native and cultivated species of Ecuador commonly known as achiote (annatto), this species is very versatile with a wide variety of uses and applications of its leaves, fruits and seeds. In this study, the chemical composition, enantiomeric distribution and biological activity of essential oil isolated from the leaves of Bixa orellana were determined. Hydrodistillation was used to isolate the essential oil. Gas chromatography coupled with mass spectrometry was used to determine the qualitative composition, a gas chromatograph equipped with a flame ionization detector was used to determine quantitative composition and gas chromatography on an enantioselective column was used to determine enantiomeric distribution. Antibacterial activity was determined using the broth microdilution method, for which we used three Gram-positive cocci bacteria, a Gram-positive bacilli bacterium and three Gram-negative bacilli bacteria. 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic (ABTS) acid radical cation and 2,2-diphenyl-1-picrylhydryl (DPPH) free radical were used as reagents for determining the antioxidant activity of the essential oil. The spectrophotometric method was used to analyze acetylcholinesterase inhibitory effect of the essential oil. The yield of leaves in essential oil was 0.13 ± 0.01% (v/w). A total of 56 chemical compounds, which represent 99.25% of the total composition, were identified in the essential oil. Sesquiterpene hydrocarbons were the most representative group in number of compounds and relative abundance with 31 compounds and 69.06%, respectively. The principal constituents were found to germacrene D (17.87 ± 1.20%), bicyclogermacrene (14.27 ± 0.97%), caryophyllene < (E)- > (8.56 ± 1.24%) and pinene <α-> (6.34 ± 0.13%). Six pairs of enantiomers were identified in the essential oil of Bixa orellana. The essential oil presented strong activity against the Enterococcus faecium (ATCC 27270) with an MIC of 250 µg/mL and weak activity against Enterococcus faecalis (ATCC 19433) and Staphylococcus aureus (ATCC 25923) with an MIC of 1000 µg/mL. The antioxidant activity of the essential oil was strong according to ABTS methods with a SC50 of 61.49 ± 0.04 µg/mL and was moderate in DPPH with a SC50 of 224.24 ± 6,4 µg/mL. Additionally, the essential oil reported moderate anticholinesterase activity with an IC50 of 39.45 ± 1.06 µg/mL.

Biological Activities and Chemical Composition of Essential Oil from Hedyosmum purpurascens (Todzia)-An Endemic Plant in Ecuador.

Hedyosmum purpurascens is an endemic species found in the Andes of Ecuador and it is characterized by its pleasant smell. In this study, essential oil (EO) from H. purpurascens was obtained by the hydro-distillation method with a Clevenger-type apparatus. The identification of the chemical composition was carried out by GC-MS and GC-FID in two capillary columns, DB-5ms and HP-INNOWax. A total of 90 compounds were identified, representing more than 98% of the total chemical composition. Germacrene-D, ϒ-terpinene, α-phellandrene, sabinene, O-cymene, 1,8-cineole and α-pinene accounted for more than 59% of the EO composition. The enantioselective analysis of the EO revealed the occurrence of (+)-α-pinene as a pure enantiomer; in addition, four pairs of enantiomers were found (α-phellandrene, o-cymene, limonene and myrcene). The biological activity against microbiological strains and antioxidants and the anticholinesterase properties were also evaluated and the EO showed a moderate anticholinesterase and antioxidant effect, with an IC50 value of 95.62 ± 1.03 µg/mL and a SC50 value of 56.38 ± 1.96. A poor antimicrobial effect was observed for all the strains, with MIC values over 1000 µg/mL. Based on our results, the H. purpurasens EO presented remarkable antioxidant and AChE activities. Despite these promising results, further research seems essential to validate the safety of this medicinal species as a function of dose and time. Experimental studies on the mechanisms of action are essential to validate its pharmacological properties.

Chemical Composition and Biological Activity of Essential Oil from Leaves and Fruits of Limoncillo (Siparuna muricata (Ruiz & Pav.) A. DC.).

Siparuna muricata is an aromatic native shrub or tree from Ecuador known as "limoncillo" or "limón de la sierra" due to its citrus odor. In this study, the chemical composition and biological activity of essential oil from the leaves and fruits of this species was determined. The essential oil was isolated by subjected to hydrodistillation. The chemical composition was determined by gas chromatography equipped with a flame ionization detector and gas chromatography coupled to mass spectrometry. The enantiomeric distribution was determined by gas chromatography using an enantioselective column. The antimicrobial activity against three Gram-positive bacteria, two Gram-negative bacteria and two fungi was determined by the broth microdilution method. The antioxidant activity was analyzed using the 2,2-diphenyl-1-picrylhydryl free radical and 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid radical cation scavenging activity of essential oil. The acetylcholinesterase inhibitory effect of the essential oil was measured using a spectrophotometric method. The yield was 1.2 ± 0.1 mL/kg for leaves and 1.8 ± 0.2 mL/kg for fruits. A total of 51 compounds were identified in the leaves of the essential oil and 41 in the fruits. In both cases, the chemical compositions were dominated by the group of monoterpene hydrocarbons compounds. The main compound was α-pinene with 23.22 ± 1.03% in essential oil of the leaves and limonene with 24.92 ± 1.20% in the fruits. In both essential oils, five pairs of enantiomers with different enantiomeric excesses were identified. The essential oil of limoncillo leaves presented a strong activity against the fungus Aspergillus niger (ATTC 10231) and Gram-positive bacterium Enterococcus faecium (ATCC 27270) with a MIC of 250 µg/mL and 500 µg/mL, respectively. The essential oil from fruits and leaves of Siparuna muricata presented a moderate antioxidant activity with the ABTS method with a SC50 of 775.3 ± 1.3 µg/mL and 963.3 ± 1.6 µg/mL, respectively. Additionally, the leaves essential oil reported an IC50 value of 52.98 ± 1.04 µg/mL and the fruits essential oil an IC50 value of 98.84 ± 1.04 µg/mL, which can be considered a very strong anticholinesterase activity.

Chemical and Biological Activity Profiling of Hedyosmum strigosum Todzia Essential Oil, an Aromatic Native Shrub from Southern Ecuador

The present study aimed to determine the chemical composition, enantiomeric distribution and the biological profile of Hedyosmum strigosum essential oil (EO). The antioxidant properties and anticholinesterase effect were measured by spectroscopic methods and antimicrobial potency assessed against 8 bacteria and two fungi. H. strigosum is a native shrub, particularly found in Ecuador and Colombia at 2000 to 3500 m a.s.l. Chemical composition was determined by GC-MS and GC-FID. A total of 44 compounds were detected, representing more than 92% of the EO composition. The main compounds were thymol (24.35, 22.48%), α-phellandrene (12.15, 13.93%), thymol acetate (6.59, 9.39%) and linalool (8.73, 5.82%), accounting for more than 51% of the EO. The enantioselective analysis revealed the presence of 5 pure enantiomers and 3 more as a racemic mixture. The EO exerted a strong antioxidant capacity, determined by ABTS assay, with a SC50 of 25.53 µg/mL and a strong and specific antimicrobial effect against Campylobacter jejuni with a MIC value of 125 µg/mL. A moderate acetylcholinesterase inhibitory effect was also observed with an IC50 value of 137.6 µg/mL. To the best of our knowledge this is the first report of the chemical composition and biological profile of H. strigosum EO.

Chemical Composition, Enantiomeric Distribution and Anticholinesterase and Antioxidant Activity of the Essential Oil of Diplosthephium juniperinum.

The aim of this study was to extract and identify the chemical compounds of Diplosthephium juniperinum essential oil (EO) from Ecuador and to assess its anticholinesterase and antioxidant properties. The EO chemical composition was determined by GC−MS. A total of 74 constituents of EO were identified, representing 97.27% in DB-5ms and 96.06% in HP-INNOWax of the total EO. The major constituents (>4.50%) identified were: α-pinene (21.52, 22.04%), geranyl acetate (10.54, 7.78%), silphiper-fol-5-ene (8.67, 7.38%), α-copaene (8.26, 8.18%), 7-epi-silphiperfol-5-ene (4.93, 5.95%), and germacrene D (4.91, 6.00%). Enantioselective analysis of the volatile fraction of D. juniperinum showed: (+)-α-pinene as a pure enantiomer and 5 pairs of enantiomeric compounds. Among them, (−)-ß-Pinene and (−)-Germacrene D presented a high enantiomeric excess of 93.23 and 84.62%, respectively, while (−)-α-Thujene, (−)-Sabinene and (S)-4-Terpineol with a lower enantiomeric excess of 56.34, 47.84 and 43.11%, respectively. A moderate inhibitory effect was observed for Acetylcholinesterase (AChE) and Butyrylcholinesterase (BuChE) enzymes with IC50 values of 67.20 ± 7.10 and 89.00 ± 9.90 µg/mL, respectively. A lower antioxidant potential was observed for the EO measured through DPPH and ABTS radical scavenging assays with SC50 values of 127.03 and >1000 µg/mL, respectively. To the best of our knowledge, this is the first report of the chemical composition, enantiomeric distribution and, anticholinesterase and antioxidant potential of the EO of D. juniperinum. As future perspective, further in-vivo studies could be conducted to confirm the anticholinesterase potential of the EO.

Enantiomeric Composition, Antioxidant Capacity and Anticholinesterase Activity of Essential Oil from Leaves of Chirimoya (Annona cherimola Mill.).

Annona cherimola Mill. is a native species of Ecuador cultivated worldwide for the flavor and properties of its fruit. In this study, hydrodistillation was used to isolate essential oil (EO) of fresh Annona cherimola leaves collected in Ecuadorian Sierra. The EO chemical composition was determined using a non-polar and a polar chromatographic column and enantiomeric distribution with an enantioselective column. The qualitative analysis was carried out by gas chromatography coupled to a mass spectrometer and quantitative analysis using gas chromatography equipped with a flame ionization detector. The antibacterial potency was assessed against seven Gram-negative bacteria and one Gram-positive bacterium. ABTS and DPPH assays were used to evaluate the radical scavenging properties of the EO. Spectrophotometric method was used to measure acetylcholinesterase inhibitory activity. GC-MS analysis allowed us to identify more than 99% of the EO chemical composition. Out of the fifty-three compounds identified, the main were germacrene D (28.77 ± 3.80%), sabinene (3, 9.05 ± 1.69%), ß-pinene (4, 7.93 ± 0.685), (E)-caryophyllene (10.52 ± 1.64%) and bicyclogermacrene (11.12 ± 1.39%). Enantioselective analysis showed the existence of four pairs of enantiomers, the (-)-ß-Pinene (1S, 5S) was found pure (100%). Chirimoya essential oil exhibited a strong antioxidant activity and a very strong anticholinesterase potential with an IC50 value of 41.51 ± 1.02 µg/mL. Additionally, EO presented a moderate activity against Campylobacter jejuni and Klebsiella pneumoniae with a MIC value of 500 µg/mL.

Chemical composition, enantiomeric analysis and anticholinesterase activity of Lepechinia betonicifolia essential oil from Ecuador.

CONTEXT: Due to the interesting potential of essential oils (EO) against cholinesterases and their close relation in Alzheimer's disease, the EO of Lepechinia betonicifolia (Lam) Epling (Lamiaceae), a native shrub from Ecuador, was assessed. Chemical profiling and enantiomeric distribution were also recorded for the first time. OBJECTIVE: To analyse the chemical profile including the enantiomeric composition and anticholinesterase effect exerted by EO of L. betonicifolia. MATERIALS AND METHODS: The EO of L. betonicifolia fresh aerial parts was obtained by hydrodistillation in a Clevenger-type apparatus. Physical properties were determined according to standard norms. The chemical composition was determined by GC-MS and GC-FID. Enantioselective GC-MS analysis was carried out by using a capillary chiral column. Anticholinesterase effect was assessed by Ellman's method with acetylthiocoline as substrate and Ellman's reagent (DTNB) to detect its hydrolysis at 405 nm for 60 min. Donepezil was used as a reference drug. EO was dissolved in methanol to reach 10 mg/mL concentration and two more 10× dilutions were included. RESULTS: Thirty-nine constituents were identified corresponding to 97.55% of the total oil composition. The main components were ß-pinene (30.45%), sabinene (27.98%), α-pinene (4.97%), ß-phellandrene (4.79%), E-caryophyllene (4.44%) and limonene (3.84%). L. betonicifolia EO exerted a strong inhibitory effect over the AChE enzyme with an IC50 value of 74.97 ± 1.17 µg/mL. DISCUSSION AND CONCLUSIONS: Current chemical characterisation and anticholinesterase effect of EO of L. betonicifolia encourage us to propose this EO as a candidate for the preparation of functional foods or as adjuvant therapy for Alzheimer's disease.

Chemical Constituents of the Essential Oil from Ecuadorian Endemic Species Croton ferrugineus and Its Antimicrobial, Antioxidant and α-Glucosidase Inhibitory Activity.

Croton ferrugineus Kunth is an endemic species of Ecuador used in traditional medicine both for wound healing and as an antiseptic. In this study, fresh Croton ferrugineus leaves were collected and subjected to hydrodistillation for extraction of the essential oil. The chemical composition of the essential oil was determined by gas chromatography equipped with a flame ionization detector and gas chromatography coupled to a mass spectrometer using a non-polar and a polar chromatographic column. The antibacterial activity was assayed against three Gram-positive bacteria, one Gram-negative bacterium and one dermatophyte fungus. The radical scavenging properties of the essential oil was evaluated by means of DPPH and ABTS assays. The chemical analysis allowed us to identify thirty-five compounds representing more than 99.95% of the total composition. Aliphatic sesquiterpene hydrocarbon trans-caryophyllene was the main constituent with 20.47 ± 1.25%. Other main compounds were myrcene (11.47 ± 1.56%), ß-phellandrene (10.55 ± 0.02%), germacrene D (7.60 ± 0.60%), and α-humulene (5.49 ± 0.38%). The essential oil from Croton ferrugineus presented moderate activity against Candida albicans (ATCC 10231) with an MIC of 1000 µg/mL, a scavenging capacity SC50 of 901 ± 20 µg/mL with the ABTS method, and very strong antiglucosidase activity with an IC50 of 146 ± 20 µg/mL.

Phytochemical profile, antimicrobial and antioxidant activities of essential oil extracted from Ecuadorian species Piper ecuadorense sodiro.

In the present research, the essential oil from Piper ecuadorense was analysed by GC/MS and GC/FID techniques. A total of forty-four chemical compounds were identified which represent 98.65% of the essential oil composition. The main compounds were bicyclogermacrene (12.98%), 3-thujopsanone (11.59%), α-phellandrene (6.89%), (E)-nerolidol (6.88%), δ-elemene (6.83%) and shyobunol (5.79%). The essential oil from P. ecuadorense exerted a strong activity against Gram-positive bacterium Staphylococcus aureus (ATCC 25923) with an MIC of 250 µg/mL, and a very strong activity against Trichophyton rubrum (ATCC 28188) and Trichophyton mentagrophytes (ATCC 28185) with an MIC of 62.5 µg/mL in both cases. The antioxidant activity of essential oil was explored using DPPH and ABTS method, through ABTS assay. The oils showed an IC50 of 1.81 ± 0.09 mg/mL. This is the first report on the chemical composition and biological activity of essential oil from this species.

Extraction and Study of the Essential Oil of Copal (Dacryodes peruviana), an Amazonian Fruit with the Highest Yield Worldwide.

Essential oils are highly demanded substances worldwide. They can be used without modification due to their different chemical and biological properties or as natural sources of chemical compounds. The limit in the use of these metabolites is their low yield. In the present investigation, the essential oil of fruits from Dacryodes peruviana collected in the Ecuadorian Amazon was extracted and studied. The essential oil was released from the plant matrix and isolated by hydrodistillation. The yields obtained were 4.8 ± 0.2% and 11.3 ± 0.2% for fresh and dried fruits, respectively, one of the highest yields on record to date. Twenty-five chemical compounds were identified by GC/MS and GC/FID techniques. The principal constituent was α-phellandrene, with 50.32 ± 3.32%. The antimicrobial activity of the oil was assayed against five Gram negative bacteria, two Gram positive bacteria and two fungi. The essential oil exerted a moderate activity against Staphylococcus aureus. The repellent activity of the oil was assayed against mosquitoes (Diptera: Culicidae); the samples with 3%, 2% and 1% essential oil were class 4, and the sample with 0.5% showed to be class 3. The essential oil showed a weak antioxidant activity through the DPPH and ABTS methods.

Staurosporine from Streptomyces sanyensis activates Programmed Cell Death in Acanthamoeba via the mitochondrial pathway and presents low in vitro cytotoxicity levels in a macrophage cell line.

Recently, the search for novel therapeutic agents against Acanthamoeba species has been focused on the evaluation of natural resources. Among them, marine microorganisms have risen as a source of bioactive compounds with the advantage of the ability to obtain unlimited and constant amounts of the compounds in contrast to other natural sources such as plants. Furthermore, marine actinomycetes have recently been reported as highly rich in bioactive agents including salinosporamides, xiamycines, indolocarbazoles, naphtyridines, phenols, dilactones such as antimycines and macrolides among others. In this study, staurosporine (STS) was isolated from a strain of Streptomyces sanyensis and tested against Acanthamoeba to characterize the therapeutic potential of STS against this protozoan parasite. We have established that STS is active against both stages of the Acanthamoeba life cycle, by the activation of Programmed Cell Death via the mitochondrial pathway of the trophozoite. We have also established that STS has relatively low toxicity towards a macrophage cell line. However, previous studies have highlighted higher toxicity levels induced on other vertebrate cell lines and future research to lower these toxicity issues should be developed.

Chemical composition and antimicrobial activity of Myrcianthes fragrans essential oil, a natural aromatizer of the traditional Ecuadorian beverage colada morada.

ETHNOBOTANICAL AND ETHNOMEDICINAL RELEVANCE: The importance given in Ecuador to the rescue of traditional knowledge and nutritional value of ancestral foods and drinks, has stimulated our investigation of the chemical composition and some biological activities of M. fragrans ('arrayán') essential oil, a natural aromatic additive used in the preparation of the traditional fruit-juice 'colada morada', which is typically drunk in the Day of the Dead or All Soul´s Day. MATERIAL AND METHODS: Different essential oils of Myrcianthes fragrans (Sw.) McVaught were obtained by hydrodistillation of the aerial parts of the plant collected in Cerro Villonaco (Loja-Ecuador) at three different phenological growth stages, i.e., during foliation (Fo), flowering (Fl) and fruiting (Fr) stages. The chemical compositions of the essential oils were determined by GC/MS and GC/FID techniques. The antimicrobial activities were determined by the broth microdilution method and reported as minimal inhibitory concentration (MIC, ug/mL). AIMS OF THE STUDY: i) to investigate the traditional uses of arrayán (M. fragrans) in the South region of Ecuador; ii) to identify the main components of the essential oils isolated at different phenological stages; iiì) to test the antimicrobial activity of the essential oils against bacteria and yeasts causing human ailments and a yeast causing food spoilage. RESULTS: 37, 46 and 38 compounds, representing 96.5%, 96.2%, and 95.6% of the three essential oils (Fo, Fl and Fr), respectively, have been identified. Oxygenated monoterpenes (OM) were the major components with percentages of 63.1 (Fo), 49.4 (Fl), and 61.9% (Fr), respectively. The main constituents of the essential oils were the monoterpene aldehydes geranial (1) and neral (2), the content of which varied, depending on the phenological development stage of the plant, spanning from 31.1% and 23.6% (Fo), to 23.6% and 17.8% (Fl), and 29.7% and 24.3% (Fr), respectively. In vitro antimicrobial tests showed that the essential oils from M. fragrans exhibited good activity against the Gram-negative bacteria, K. pneumoniae, and against the yeasts, C. albicans and S. cerevisiae. CONCLUSIONS: The oil is characterized by a high concentration of the monoterpene aldehydes geranial and neral (citral), that make the aroma of colada morada prepared in southern Ecuador quite different from the beverage made in other regions of the country, where other types of myrtles (Myrtaceae spp.) are used. Moreover, the oil may become a new rich source of the important industrial chemical citral. The pleasant aromatic properties and the good in vitro antimicrobial activity of arrayán oil suggest a plausible scientific explanation for the traditional uses of the plant not only as a natural aromatizer of a traditional beverage but also as a natural anti-infective and anti-yeast agent.

Acorenone B: AChE and BChE Inhibitor as a Major Compound of the Essential Oil Distilled from the Ecuadorian Species Niphogeton dissecta (Benth.) J.F. Macbr.

This study investigated the chemical composition, physical proprieties, biological activity, and enantiomeric analysis of the essential oil from the aerial parts of Niphogeton dissecta (culantrillo del cerro) from Ecuador, obtained by steam distillation. The qualitative and quantitative analysis of the essential oil was realized by gas chromatographic and spectroscopic techniques (GC-MS and GC-FID). Acorenone B was identified by GC-MS and NMR experiments. The enantiomeric distribution of some constituents has been assessed by enantio-GC through the use of a chiral cyclodextrin-based capillary column. We identified 41 components that accounted for 96.46% of the total analyzed, the major components were acorenone B (41.01%) and (E)-ß-ocimene (29.64%). The enantiomeric ratio of (+)/(-)-ß-pinene was 86.9:13.1, while the one of (+)/(-)-sabinene was 80.9:19.1. The essential oil showed a weak inhibitory activity, expressed as Minimal Inhibitory Concentration (MIC), against Enterococcus faecalis (MIC 10 mg/mL) and Staphylococcus aureus (MIC 5 mg/mL). Furthermore, it inhibited butyrylcholinesterase with an IC50 value of 11.5 µg/mL. Pure acorenone B showed inhibitory activity against both acetylcholinesterase and butyrylcholinesterase, with IC50 values of 40.8 µg/mL and 10.9 µg/mL, respectively.

Antibacterial and cytotoxic activity from the extract and fractions of a marine derived bacterium from the Streptomyces genus.

CONTEXT: Marine natural products are a rich source of potent, selective, and structurally novel compounds. Marine bacteria are considered the most promising source of biologically active compounds which can be applied to treat a wide range of diseases. OBJECTIVE: The current study was designed to establish the bases for a future marine exploration in the Ecuadorian coast based on the molecular identification of a marine bacterium and its potential use as an antibacterial or cytotoxic compounds source. MATERIALS AND METHODS: Isolation and characterization of the marine bacterium were carried out through microbiological methods from desiccated sediment. Molecular identification was made by means of 16S rDNA analysis. MIC was measured by the microdilution broth method against six pathogenic bacteria: two Gram positive and four Gram negative strains. Cytotoxicity was evaluated by Crystal violet assay against breast adenocarcinoma (MCF7) and ductal carcinoma (T47D and ZR-75-30). RESULTS: Our present study has shown that EtOAc extract and fraction A1 obtained from marine Streptomyces sp. revealed the maximal antibacterial and cytotoxic activity. Enterococcus faecalis was found to be more sensitive strain (MIC 0.78 µg/ml) than the other five bacteria tested. ZR-75-30 and T47D cell lines were found to be more sensitive (IC50 value, 31.88 ± 0.05 and 68.35 ± 0.12 µg/ml) than adenocarcinoma MCF7 (IC50 value was 83.65 ± 0.06 µg/ml). DISCUSSION AND CONCLUSION: The results obtained herein indicate that EtOAc extract of Streptomyces sp. has shown a strong antibacterial activity as well as moderate cytotoxic activity which make it a good candidate for metabolite isolation.