A Comparative Study on Chemical Compositions and Biological Activities of Four Amazonian Ecuador Essential Oils: Curcuma longa L. (Zingiberaceae), Cymbopogon citratus (DC.) Stapf, (Poaceae), Ocimum campechianum Mill. (Lamiaceae), and Zingiber officinale Roscoe (Zingiberaceae) (original) (raw)
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CHEMICAL ANALYSIS OF AMAZONIAN ESSENTIAL OILS OF AN ECUADORIAN SHUAR COMMUNITY
This research was carried out with the aim of determining the chemical composition of the essential oils of four Amazonian species from the Antuash community, Morona canton, province of Morona Santiago. These species belong to the main aromatic families of Ecuador. The essential oils (EO) of Critoniopsis pycnantha (Benth.) H. Rob., Myrcia aliena McVaugh, Piper macrotrichum C. DC. and Siparuna schimpffii Diels were obtained from the dry leaves by analytical steam distillation; a percentage yield of 0.24 %, 0.80 %, 0.44 %, and 0.32 % was achieved respectively. EO were qualitatively analyzed by gas chromatography coupled to mass spectrometry (GC-MS) and quantitatively analyzed by gas chromatography coupled to flame ionization detector (GC-FID) with a DB-5ms apolar column. The compounds were identified based on mass spectra and the Van Den Dool and Kratz retention indices. They were quantified by calculating the relative response factors based on the combustion enthalpies. M. aliena and P. macrotrichum resulted rich in monoterpenes, and C. pycnantha and S. schimpffii in sesquiterpenes. The major compounds for the essential oils of C. pycnantha were γ-muurolene, bicyclogermacrene, (E)-caryophyllene α-ylangene and α-humulene; M. aliena: α-pinene and β-pinene; P. macrotrichum δ-3-carene, eugenol and chavibetol acetate; and S. schimpffii: spathulenol, 2-undecanone, bicyclogermacrene and (E)-Isocroweacin.
Bioprospecting the Cerrado’s Aromatic Flora: Chemical and Biological Studies of Three Essential Oils
Brazilian Archives of Biology and Technology, 2023
Chemical and pharmacological potentials of botanical species found in the Cerrado are well-known and widely studied. Chemical diversity of secondary metabolites produced by plants that belong to this Brazilian biome has triggered several studies in the fields of farming, pharmaceutical and cosmetic industries. Therefore, this study aimed at evaluating the chemical composition of essential oils (EOs) from fresh leaves of three species found in the Brazilian Cerrado: Cardiopetalum calophyllum Schltdl. (EO-CC), Campomanesia adamantium (Cambess.) O. Berg (EO-CA) and Protium ovatum Engl. (EO-PO) and at determining their anti-Malassezia furfur and anti-inflammatory activities. Both GC-FID and GC-MS showed that the most abundant chemical class of the oils was the one of sesquiterpene hydrocarbons. The major constituents identified in EO-CC were germacrene D (34.9%) and bicyclogermacrene (26.8%). EO-CA exhibited mainly germacrene D (21.7%) while EO-PO had high concentrations of germacrene D (25.0%) and γ-muurolene (18.6%). EOs were tested by the broth microdilution method on 96-well microplates and exhibited satisfactory activity against M. furfur, i. e., EO-CA had MIC = 375 µg/mL while EO-CC and EO-PO HIGHLIGHTS • The sesquiterpene germacrene D was the major constituent in the three EOs under investigation. • EO from Campomanesia adamantium was considered active against Malassezia furfur. • All EOs exhibited in vitro anti-inflammatory activity by the chemotaxis model. • The most abundant metabolite class of all EOs under study was formed by sesquiterpene hydrocarbons.
Molecules, 2019
The chemical composition and biological activity of essential oils isolated from the leaves of Siparuna aspera, Siparuna macrotepala, Piper leticianum, Piper augustum and the rhizome of Hedychium coronarium were evaluated. These species are used medicinally in different ways by the Amazonian communities that live near the Kutukú mountain range. Chemical studies revealed that the main components for the two Siparuna species were germacrene D, bicyclogermacrene, α-pinene, δ-cadinene, δ-elemene, α-copaene and β-caryophyllene; for the two Piper species β-caryophyllene, germacrene D, α-(E,E)-farnesene, β-elemene, bicyclogermacrene, δ-cadinene and for H. coronarium 1,8-cineole, β-pinene, α-pinene and α-terpineol. The antioxidant activity of all essential oils was evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), photochemiluminescence (PCL) quantitative assays, and DPPH and ABTS bioautographic profiles, with different results for each of them. Antimicrobial activity studies were carried out on three yeasts, six Gram positive and four Gram negative bacteria, by means of the disc diffusion method. The essential oil of H. coronarium showed the most relevant results on L. grayi, K. oxytoca and S. mutans, P. augustum and P. leticianum on S. mutans. An antibacterial bioautographic test for H. coronarium was also carried out and highlighted the potential activity of terpinen-4-ol and 1,8-cineole.
Biochemical Systematics and Ecology, 2003
Air-dried samples of 20 Brazilian populations of Cunila galioides were extracted by steam distillation and analyzed using GS and GS-MS. A total of 40 volatile compounds were detected and identified. Fourteen compounds were presented in high concentration, (Ͼ10% of the essential oils) in at least one of the populations, and were used to analyze the relationship between the populations. Three affinity groups, which can be considered as chemotypes, were formed by the average linkage cluster analysis. The citral group was characterized by high concentrations of neral and geranial (28 ± 1.49% and 40.5 ± 1.73%, respectively), the ocimene group by high concentration of trans-β-ocimene (33.05 ± 2.54%), and the menthene group by the presence of 1,8-cineole (10.69 ± 2.93%), trans-p-2,8-menthadiene-1-ol (11.46 ± 1.54%), 1,3,8menthatriene (10.39 ± 1.41%), and 1,5,8-p-menthatriene (7.75 ± 2.32%), as their main constituents. Geographically, the chemotypes containing citral originated from the northeast plateau of Rio Grande do Sul, whereas chemotypes containing ocimene originated from the grasslands of high altitudes of the Atlantic range, and those of the menthene group were found in a transition area between the two regions. The chemovariation observed appear to be genetically determined.
Comparison of leaf anatomy and essential oils from
Botanical Studies, 2014
Background: Drimys brasiliensis Miers is native to Brazil, where it is mainly found in montane forests and flooded areas in the South and Southeast regions of the country. The objectives of the present study were to compare the leaf anatomy and the chemical constitution of the essential oils from D. brasiliensis present in two altitude levels (1900 and 2100 m), in a Montane Cloud Forest, in Itamonte, MG, Brazil. Results: A higher number of sclereids was observed in the mesophyll of the leaves at 1900 m altitude. At 2100 m, the formation of papillae was observed on the abaxial surface of the leaves, as well as an increase in the stomatal density and index, a reduction in leaf tissue thickness, an increase in the abundance of intercellular spaces in the mesophyll and an increase in stomatal conductance and in carbon accumulation in the leaves. Fifty-nine constituents have been identified in the oils, with the predominance of sesquiterpenes. Two trends could be inferred for the species in relation to its secondary metabolism and the altitude. The biosyntheses of sesquiterpene alcohols at 1900 m, and phenylpropanoids and epi-cyclocolorenone at 2100 m, were favored. Conclusions: D. brasiliensis presented a high phenotypic plasticity at the altitude levels studied. In relation to its leaf anatomy, the species showed adaptive characteristics, which can maximize the absorption of CO 2 at 2100 m altitude, where a reduction in the partial pressure of this atmospheric gas occurs. Its essential oils presented promising compounds for the future evaluation of biological potentialities.
GC-MS analysis of pesticidal essential oils from four Kenyan plants
African Journal of Biotechnology, 2015
Essential oils are complex mixtures of odours and steam volatile compounds which are deposited by plants in the subcuticular space of glandular hairs, in excretory cavities and canals or exceptionally in heart wood. Essential oils have been found to have no specific biological functions in plants, but constitute many compounds that are insect repellents or act to alter insect feeding behavior, growth and development, ecdysis (moulting) and behavior during mating and oviposition. Others possess antifungal, insecticidal and antiseptic properties. Essential oils of leaves of Tagetes minuta L. (Asteraceae), Fuerstia africana T.C.E. Friers (Labiaae), Tephrosia vogelii Hook. f. (Leguminosae) and Sphaeranthus ukambensis were obtained by steam distillation using the Clevenger apparatus (Guenter, 1949). Compounds in the essential oils were identified by gas chromatography-mass spectrometry (GC-MS). The characteristic volatiles isolated from the four plants were identified as follows: major constituents of the essential oils from F. africana included the following: limonene (39.1%), (Z)-β-ocimene (30.5%), targetone (26.2%), E-targetone (59%), λ-terpinene (26.2 %), peripitenone 23.7%, ocimene allo (22.8%) and Z-targetone (100%). The compounds with the highest relative abundance value in the essential oils included Z-targetone, E-targetone and (Z)-β-Ocimene. Analysis of T. minuta also revealed a number of compounds which included mycene (20.1%), verbinene (8.0%), Z-ocimenone (35.2%), E-caryophylene (25.5%), α-Humelene (11.8%), germacrene D (21.4%) and camphene (2%). The major constituent of T. minuta was Z-ocimene, caryophylene E and mycene. Essential oils from T. vogelii as revealed by the GC-MS analysis were pinene α (32.7%), limonene (35.1%), copaene α (22.9%), βelemene (36.7%), Z-nerolidol (77.7%), δ-cadinene (67.6%), α humelene (69.6%) and-4-α-ol-(β)copaene (65.7%). The highest proportion of the essential oils constituted Z-nerolidol δ-cadinene, α-humelene and 4-α-ol-β. Copaene. The compounds in essential oils obtained from S. ukambensis were α-copaene (23.8%), β-bourbonene (25.5%), αgurjunene (14.3%), cymene<2, 5-dimethoxy-para (87.7%), α-humelene (100%), λ-muurolene (17.9%), λ-cadinene (77.3%), caryophylene oxide (54.7%) and δ-cadinene (61.9%). The major compounds contained in essential oils from S. ukambensis were α-humele, λ-cadinene, δ-cadinene and cymene<2, 5-dimethoxy-para. The compounds which were common in the four test plants included: α-pinene, α-humele, ocimene allo and (E) β-ocimene. Each of the test plant secreted essential oils constituting numerous volatiles known to exhibit acaricidal, insecticidal and/or arthropod repellent properties. These plants may be useful sources of compounds for use in the control of arthropods of medical, veterinary and agricultural importance.
Major bioactivities and mechanism of action of essential oils and their components
Essential oils are gaining increasing interest for their antimicrobial and antiviral properties, as well as for their preventive and therapeutic actions against many human pathologies. Herein, we present an overview on new discoveries in essential oil research, discussing antimicrobial activity, as well as immunomodulatory, anti-apoptotic, anti-angiogenic and anti-tumoural properties. In addition, we emphasize recent advances in the identification of bioactive components and understanding of their mechanism of action. We discuss their molecular diversity and wide spectrum of activity as well as their structure-activity relationships and capability of targeting paradoxical responses triggered by different genes and pathways. Finally, we emphasize the effort required to isolate and identify the bioactive components of essential oils and to determine their cytotoxicity as their specificity. Thus, new approaches to specifically address bioactive components to selected targets could enhance the latter property in order to accommodate any cytotoxicity towards dysfunctioning loci.
Food Chemistry, 2011
Croton lechleri essential oil has been obtained by steam distillation of fresh stem bark from Amazonian Ecuador adult plants (yield: 0.61 ml/kg [0.061%]; density: 1.01 g/ml), and then chemically characterised by GC (Gas Chromatography) and GC-MS (gas chromatography-mass spectrometry). Seventy-four chemicals were detected and identified; the most abundant in descending order, were the sesquiterpenes sesquicineole (17.29%), a-calacorene (11.29%), 1,10-di-epi-cubenol (4.75%), b-calacorene (4.34%) and epicedrol (4.09%). Monoterpenes checked with a relative peak area higher than 2.0% were a-pinene (2.01%), p-cymene (2.61%), limonene (4.20%) and borneol (2.67%). The structure of the main chemicals were confirmed by GC-MS and 1 H NMR analyses. Spectrophotometric 1,1-diphenyl-2-picrylhydrazyl (DPPH) and DPPH-(high performance) thin layer chromatography (DPPH-(HP)TLC) bioautographic assays showed a lower radical scavenging capacity (IC 50 ) with respect to commercial thyme essential oil and BHA (butylated hydroxyl anisole), pointing out, however, that the C. lechleri essential oil fraction, characterised by a-calacorene, b-calacorene and d-cadalene, was the most involved in the bioactivity. Similar results were obtained with b-carotene bleaching assay, where the IC 50 values were 0.291 ± 0.024 mg/ ml for C. lechleri essential oil, 0.164 ± 0.013 and 1.34 Â 10 À4 ± 10 À5 mg/ml for thyme essential oil and BHA, respectively. (HP)TLC-bioautographic assay performed with Gram positive and Gram negative bacteria revealed a minimum inhibitory concentration (MIC) values comprised between 0.10 mg/ml (Escherichia coli) and 10.10 mg/ml (for e.g. Pseudomonas aeruginosa), and the fraction mainly characterised by sesquicineole (97.38%) as the most involved in antibacterial capacity. Ames test employing Salmonella typhimurium TA98 and TA100 with and without a metabolic activation mixture (S9 mix) demonstrated the absence of mutagenicity of the C. lechleri essential oil between a concentration range of 10 À2 and 100 mg/plate. The same results were achieved by Saccharomyces cerevisiae D7 strain assay. An interesting mutagen-protective efficacy was evidenced by a 30% and 33% revertants reduction of TA98 strain treated with 2-aminoanthracene and nitrofluorene (2 lg/plate), suggesting, above all, the possibility to employ C. lechleri essential oil as a new flavouring protective ingredient for foods or dietary supplements against potential mutagens formed during cooking and/or processing in general.
Records of Natural Products
Twelve Unonopsis specimens, comprising five species commonly found at Amazonas state (Brazil) were collected in three different sites. The leaves of the specimens were extracted by hydrodistillation and analyzed by gas chromatography coupled to mass spectrometry (GC-MS). The data were treated by chemometric analysis with the objective of verify the potential of their chemical profiles for chemotaxonomic approaches. Despite the essential oils presented spathulenol and caryophyllene oxide as a main constituent in most samples, the multivariate analysis showed significant differences between the species and their collection sites. The obtained results suggest high chemical similarity between U. floribunda and U. rufescens species and proved that U. guatterioides has a distinct chemistry when compared to the analyzed species. The chemical identification points to α-guaiene, α-calacorene and widdrol as possible chemical markers for U. floribunda and U. rufescens species.