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This article reports the chemical composition of the essential oils obtained by hydrodistillation of male and female H. scabrum fresh leaves. The essential oils, HSMO and HSFO, respectively, were analyzed by GC/MS and GC-FID. A total of 93 components were detected, accounting for 94.8% and 95.3% of HSMO and HSFO, respectively. The prevalent constituents of HSMO were pinocarvone (13.1%), d-germacren-4-ol (12.6%), 1,8-cineole (10.8%), α-pinene (6.4%), and β-pinene (4.8%), whereas the major components of HSFO were 1,8-cineole (20.5%), linalool (16.5%), α-pinene (15.0%), β-pinene (6.4%), and sabinene (6.3%). The different enantiomeric distribution of β-pinene, sabinene, limonene, linalool in the two oils, was determined. The non-volatile esters of p-coumaric and ferulic acids with borneol (1 and 4), cis-chrysanthenol (2 and 5), and cis-pinocarveol (3 and 6) were identified in the leaves after basic hydrolysis and analysis of the NMR spectra of the free acids, and GC/MS spectra of the monoterpene alcohols, respectively. Compounds 2, 3, 5, and 6 have been found in nature for the first time. These findings demonstrated that, from a chemical point of view, male and female individuals of H. scabrum collected in Ecuador seem quite differentiated between each other and from samples of the same species growing in Bolivia and in Peru., (© 2018 Wiley-VHCA AG, Zurich, Switzerland.)

The phytochemical investigation of both volatile and fixed metabolites of Clinopodium taxifolium (Kunth) Govaerts (Lamiaceae) was performed for the first time. It allowed the isolation and characterization of the essential oil and six known compounds: carvacrol ( 1 ), squalane ( 2 ), uvaol ( 3 ), erythrodiol ( 4 ), ursolic acid ( 5 ), and salvigenin ( 6 ). Their structures were identified and characterized by Nuclear Magnetic Resonance (NMR) and Gas Chromatography coupled to Mass Spectroscopy (GC-MS), and corroborated by literature. The essential oil of the leaves was obtained by hydrodistillation in two different periods and analyzed by GC-MS and GC coupled to Flame Ionization Detector (GC-FID). A total of 54 compounds were detected, of which 42 were identified (including trace constituents). The major constituents were carvacrol methyl ether (18.9-23.2%), carvacrol (13.8-16.3%) and, carvacryl acetate (11.4-4.8%). The antibacterial activities were determined as Minimum Inhibition Concentration (MIC) against Staphylococcus aureus , Enterococcus faecalis , Escherichia coli , Klebsiella pneumoniae , Proteus vulgaris , Pseudomonas aeruginosa and Micrococcus luteus . The hexane and methanol extracts exhibited activity only against Klebsiella pneumoniae (250 and 500 μg/mL respectively), while the ethyl acetate extract was inactive. The hypoglycemic activity was evaluated by the in vitro inhibition of α-glucosidase. The ethyl acetate (EtOAc) extract showed strong inhibitory activity with IC 50 = 24.88 µg/mL, however methanolic and hexanic extracts showed weak activity. As a pure compound, only ursolic acid showed a strong inhibitory activity, with IC 50 = 72.71 μM., Competing Interests: The authors declare no conflict of interest.

This study describes the GC-FID, GC/MS, GC-O, and enantioselective GC analysis of the essential oil hydrodistilled from leaves of Lepechinica mutica (Lamiaceae), collected in Ecuador. GC-FID and GC/MS analyses allowed the characterization and quantification of 79 components, representing 97.3% of the total sample. Sesquiterpene hydrocarbons (38.50%) and monoterpene hydrocarbons (30.59%) were found to be the most abundant volatiles, while oxygenated sesquiterpenes (16.20%) and oxygenated monoterpenes (2.10%) were the minor components. In order to better characterize the oil aroma, the most important odorants, from the sensorial point of view, were identified by Aroma Extract Dilution Analysis (AEDA) GC-O. They were α-Pinene, β-Phellandrene, and Dauca-5,8-diene, exhibiting the characteristic woody, herbaceus, and earthy odors, respectively. Enantioselective GC analysis of L. mutica essential oil revealed the presence of twelve couples and two enantiomerically pure chiral monoterpenoids. Their enantiomeric excesses were from a few percent units to 100%. Moreover, the essential oil exhibited moderate in vitro activity against five fungal strains, being especially effective against M. canis, which is a severe zoophilic dermatophyte causal agent of pet and human infections., (© 2017 Wiley-VHCA AG, Zurich, Switzerland.)

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)-β-ocimene (29.64%). The enantiomeric ratio of (+)/(-)-β-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 IC 50 value of 11.5 μg/mL. Pure acorenone B showed inhibitory activity against both acetylcholinesterase and butyrylcholinesterase, with IC 50 values of 40.8 μg/mL and 10.9 μg/mL, respectively., Competing Interests: The authors declare no conflict of interest.

Ethnobotanical and Ethnomedicinal Relevance: This study concerns seven Huperzia species (Lycopodiaceae), namely H. brevifolia, H. columnaris, H. compacta, H. crassa, H. espinosana, H. tetragona, H. weberbaueri, which are considered sacred plants by the Saraguro community, living in the Southern Andes of Ecuador; these plants are widely used in traditional medicine and ritual ceremonies., Material and Methods: The plants were selected on the basis of written interviews with 10 visionary healers (yachak) (2 women, 8 men), indicated as the most credible by the Saraguro Healers Council. The Informant Consensus Factor (F ic ) was determined. The first phytochemical study of the plants was performed by standard procedures, while the AChE and MAO-A inhibition by fractions enriched in high MW alkaloids, was measured in vitro., Aims of the Study: i) to investigate the uses of some Huperzia plants in healing and magical-religious practices of Saraguros; ii) to identify the main components of plant hydromethanolic extracts; iiì) to test the effects of alkaloidal fractions on the activity of two enzymes linked to mental health., Results: All the interviewed Saraguro yachak showed a high consensus about the uses of the seven Huperzia plants as purgatives and against supernatural diseases, such as the "espanto" (startle). In admixtures with other plants, some species also induce a state of trance or hallucinations in participants in magical-religious rituals. GC-MS of the volatile alkaloid fractions allowed the identification of some lycodine-type and lycopodine-type alkaloids (1-5) in H. compacta, H. columnaris, and H. tetragona. The flavones selgin) (6) and tricin (7) were isolated from H. brevifolia and H. espinosana. Tricin (7) was also detected in the other five species. The rare serratene triterpenes serratenediol (8) serratenediol-3-O-acetate (9), 21-episerratenediol (10), and 21-episerratenediol-3-O-acetate (11) were isolated from H. crassa. In addition, the presence of an unprecedented group of high molecular weight alkaloids has been determined. Alkaloid fractions of H. brevifolia, H. compacta, H. espinosana, and H. tetragona significantly inhibited AChE and MAO-A activities in vitro., Conclusions: The first phytochemical and ethnopharmacological study of seven Huperzia plants, widely used by Saraguro healers, led to the identification of several alkaloids and triterpenoids with different remarkable biological activities. In addition, alkaloid fractions exhibited a significant AChE and MAO-A inhibitory activity. These results may support the use of these plants in brews prepared for inducing psychoactive effects in participants in magical-religious ceremonies. This study confirms the rich traditional medical knowledge of Saraguro healers which must be documented and preserved for future generations., (Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.)

The phytochemical investigation of Muehlenbeckia tamnifolia , collected in Loja-Ecuador, led to the isolation of nine known compounds identified as: lupeol acetate ( 1 ); cis - p -coumaric acid ( 2 ); lupeol ( 3 ); β-sitosterol ( 4 ) trans - p -coumaric acid ( 5 ); linoleic acid ( 6 ) (+)-catechin ( 7 ); afzelin ( 8 ) and quercitrin ( 9 ). The structures of the isolated compounds were determined based on analysis of NMR and MS data, as well as comparison with the literature. The hypoglycemic activity of crude extracts and isolated compounds was assessed by the ability to inhibit α-amylase and α-glucosidase enzymes. The hexane extract showed weak inhibitory activity on α-amylase, with an IC 50 value of 625 µg·mL -1 , while the other extracts and isolated compounds were inactive at the maximum dose tested. The results on α-glucosidase showed more favorable effects; the hexanic and methanolic extracts exhibited a strong inhibitory activity with IC 50 values of 48.22 µg·mL -1 and 19.22 µg·mL -1 , respectively. Four of the nine isolated compounds exhibited strong inhibitory activity with IC 50 values below 8 µM, much higher than acarbose (377 uM). Linoleic acid was the most potent compound (IC 50 = 0.42 µM) followed by afzelin, (+)-catechin and quercitrin.

Ecuador owns many high quantity and wealthy ecosystems that contain an elevated biodiversity in flora and fauna. The use of native medicinal plants has been maintained by at least 18 different indigenous cultures; furthermore, this country has been the witness of the discovery of important medicinal plants, such as Cinchona, and is an understudied resource of new natural products. The objective of this review is to update the ethnopharmacological and phytochemical studies accomplished on the Ecuadorian flora, pointing to the 253 native families and more than 15,000 species registered at present.

Coussarea macrophylla (Mart.) Müll.Arg. (Rubiaceae) was collected in Ecuador, and the bark was extracted with AcOEt. Chromatographic separation afforded six novel 3,4-secocycloartane and 3,4-secodammarane triterpenes, named macrocoussaric acids A-F, together with the known metabolites secaubryenol and 3,4-secodammara-4(28),20,24-triene-3,26-dioic acid. The structures of the new compounds were determined on the basis of their spectroscopic data. This is the first report of 3,4-secocycloartane and 3,4-secodammarane triterpenes occurring in a Coussarea species. Macrocoussaric acids A and B (2 and 3, resp.) were found to be moderately cytotoxic against five different tumor cell lines., (Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.)

The results of the first investigation of secondary metabolites occurring in intact and damaged fruiting bodies of the European mushrooms Lactarius aurantiacus, L. subdulcis, and Russula sanguinaria are reported. The pattern of sesquiterpenes in injured R. sanguinaria is dramatically different from that of Lactarius. The structure of the new furanolactarane 4, isolated from L. aurantiacus, was established on the basis of spectral data.

Two rare cadinane-type sesquiterpenes, lyophyllone A (1) and lyophyllanetriol A (2), were isolated from the mushroom Lyophyllum transforme. The structures were elucidated on the basis of exhaustive NMR techniques, together with MS, UV-Vis and molecular modelling. The absolute configuration of lyophyllone A was determined by ab initio theoretical CD calculation performed by Density Functional Theory (DFT) using the B3PW91/6-31G(d,p) basis set. The experimental CD were found to be in good agreement with the corresponding population-weighted theoretical CD spectra, allowing for the determination of the absolute stereochemistry of the compound., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

The volatile fractions isolated from Prangos peucedanifolia FENZL leaves and flowers were investigated for their phytochemical composition and biological properties. Flower and leaf hydrodistillation afforded 3.14 and 0.49 g of yellowish oils in 1.25 and 0.41% yields, respectively, from dry vegetable materials. According to the GC-FID and GC/MS analyses, 36 (99.35% of the total oil composition) and 26 compounds (89.12%) were identified in the two oils, respectively. The major constituents in the flower volatile fraction were β-pinene (35.58%), α-pinene (22.13%), and β-phellandrene (12.54%), while m-cresol (50.38%) was the main constituent of the leaf volatile fraction. The antimicrobial activity was evaluated against several bacterial and fungal strains, on the basis of the minimum inhibitory concentration (MIC) by the micro- and macrodilution methods. The two volatile fractions showed moderate antifungal and antibacterial activities, especially against Trichophyton rubrum (MIC of 2×10(3) μg/ml), Streptococcus mutans, Streptococcus pyogenes, and Staphylococcus aureus (MIC≤1.9×10(3) μg/ml for all)., (Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.)

Phytochemical investigation of secondary metabolites of the Ecuadorian plant Schistocarpha eupatorioides (Fenzl) Kuntze (Asteraceae) afforded three phytyl fatty acid esters along with a mixture of unidentified polyprenols, the very well known sterols beta-sitosterol and stigmasterol, and their corresponding fatty acid esters and glucosyl derivatives. The structures of the compounds were elucidated on the basis of various spectroscopic means. In addition, a volatile fraction was separated the composition of which, comprising sesquiterpene hydrocarbons as the main fraction, was determined by GC-MS.

An essential oil, obtained by steam distillation of Clinopodium tomentosum (Kunth) Govaerts (Lamiaceae), collected in Ecuador, was analyzed by gas chromatography-olfactometry (GC-O) and GC-MS techniques. To our knowledge, the composition of this essential oil is described here for the first time, both from the chemical and olfactometric viewpoints. A preliminary analysis by GC-MS and using Kovats' retention indexes, lead to characterize and quantify the oil constituents, while GC-O was then applied for the identification of the main odorants. By the incremental dilution method (AEDA, CHARM Analysis), applied to the GC-O technique, the flavor dilution (FD) chromatogram was obtained. In order to calculate the TOC values of the main odorants, the relationship between the odorant concentration at the sniffing port and that one in the injected solution was established. This relationship was calculated by comparing the injected amount with the TOC value of a reference compound (limonene), obtained by dynamic dilution olfactometry. A good agreement was found between calculated and measured TOC values of few odorants.

Chrysotriones A (1) and B (2), two new 2-acylcyclopentene-1,3-dione derivatives, were isolated from the fruiting bodies of the Basidiomycete Hygrophorus chrysodon, and their structures were established by spectroscopic data and synthesis of compound 2. They represent the first examples of 2-acylcyclopentene-1,3-diones found in mushrooms and suggest an unprecedented biosynthetic pathway, starting from fatty acid derivatives. Initial tests indicated interesting antifungal activity of chrysotriones against Fusarium verticillioides, one of the common worldwide pathogens of cultivated plants.

Four enyne derivatives (1-4) and quercitrin were isolated during a bioassay-guided chromatographic separation of a methanolic extract of Erigeron apiculatus. Matricarialactone (1) and lachnophyllumlactone (2) showed a high fungitoxic activity against Pyricularia oryzae. Matricaria acid methyl ester (3) and lachnophyllum acid methyl ester (4) were, instead, less active.