Chemical Profiles and Cytotoxic Activities of Essential Oils from Six Species of Baccharis Subgenus Coridifoliae (Asteraceae)

Several Baccharis species are popularly known in traditional medicine as “carquejas”, “vassouras”, “ervas-santas” and “mio-mios”, and are used as anti-inflammatories, digestives, and diuretics. This study aimed to investigate the chemical compositions and cytotoxic activities of essential oils (EOs) of six Baccharis species belonging to subgenus Coridifoliae, namely B. albilanosa, B. coridifolia, B. erigeroides, B. napaea, B. ochracea, and B. pluricapitulata. GC/MS analyses of the EOs showed that the oxygenated sesquiterpenes spathulenol (7.32–38.22 %) and caryophyllene oxide (10.83–16.75 %) were the major components for all the species. The EOs of almost all species were cytotoxic against cancer (BT-549, KB, SK-MEL and SK-OV-3) and normal kidney (VERO and LLC-PK1) cell lines, whereas B. erigeroides EO showed cytotoxicity only against LLC-PK1. This article augments the current knowledge about the chemical-biological properties of Baccharis subgenus Coridifoliae and discusses the therapeutic potentials of these economically unexploited plants.     

Chemical Composition and Biological Screening of the Essential Oils of Micromeria macrosiphon and M. arganietorum (Lamiaceae)

The chemical composition and in vitro biological activities of the essential oil (EO) of Micromeria macrosiphon Coss. and M. arganietorum (J. Emb.) R. Morales, two Lamiaceae endemic to south Morocco, were investigated. GC/MS analysis resulted in the identification of 36 metabolites from the EO of M. macrosiphon, 45 from M. arganietorum. Borneol was the major metabolite in both oils and together with related derivatives such as camphor, accounted for 2/3 of the EO of M. macrosiphon, 1/3 of those of M. arganietorum. Pinene and terpinene derivatives were also present in high proportions. From a chemotaxonomic point of view, the composition of the examined samples may be related to those of other species endemic to Macaronesia. Both EOs showed significant toxicity towards liver HepG2 and melanoma B16 4A5 tumor cell lines at 100 μg/mL; however, they were also cytotoxic towards S17 normal cell lines, with a selectivity index <1. No antibacterial activity was noticed against 52 strains at 100 μg/mL.     

Chemical Composition and Activity of Essential Oils of Carissa macrocarpa (Eckl.) A.DC. Cultivated in Tunisia and Its Anatomical Features

This is the first study investigating the chemical composition of essential oils (EOs) isolated from different tissues of Carissa macrocarpa (Eckl .) A.DC., their antimicrobial activity and the anatomical characters of the aerial organs and the fruits. The main EO components were pentadecanal and tetradecan‐1‐ol (31.9 and 16.5% in fresh leaf EO, respectively), (E)‐nerolidol and caryophyllene oxide (27.3 and 15.0% in fruit EO, respectively), linalool and hexahydrofarnesyl acetone (30.9 and 24.9% in stem EO, respectively), benzyl benzoate (24.3% in flower EO). The fruit EO was more active against Candida albicans (MIC = 0.46 mg/mL) compared to the reference antibiotic (17.66 mg/mL). Furthermore, at this concentration it inhibited all the Gram‐positive bacteria. Concerning the anatomical features, it is noteworthy to mention the presence of a large cluster of calcium oxalate crystals inside some parenchymatous cells. Large ducts corresponding to non articulated laticifers were identified in the cortex of leaf, stem and fruit pericarp. The laticifers categories and their distribution are taxonomically important to discriminate this species from others acclimated in different countries. Considering the obtained results, EOs of C. macrocarpa can be a good source of antimicrobial compounds, contributing to solve the problem of microbial resistance to antibiotics.     

Chemodiversity Associated with Cytotoxicity and Antimicrobial Activity of Piper aduncum var. ossanum

Chemical analysis, antimicrobial activity and cytotoxic effects of essential oils (EOs) from leaves of Piper aduncum var. ossanum from two localities Bauta (EO‐B) and Ceiba (EO‐C), Artemisa Province, Cuba, were determined. EOs were obtained by hydrodistillation and analyzed by gas chromatography/mass spectrometry. EO‐B demonstrated higher activity against S. aureus and L. amazonensis; while a lower cytotoxicity on mammalian cells was observed. Both EOs displayed the same activity against Plasmodium falciparum, Trypanosoma cruzi, Trypanosoma brucei, and Leishmania infantum. Both EOs were inactive against Escherichia coli and Candida albicans.     

Chemical Composition and Cytotoxic Activity of Eucalyptus torquata Luehm. and Eucalyptus salmonophloia F. Muell. Trunk Bark Essential Oils against Human SW620 and MDA-MB-231 Cancer Cell Lines

In recent years, there has been a growing interest in the screening of natural active ingredients from Eucalyptus essential oils because of their evident importance in practical utility and their undeniable therapeutic properties. Based on this, the aim of the present study was to investigate the chemical profile of the essential oils of the trunk bark of Eucalyptus torquata Luehm. (ETEO), and E. salmonophloia F. Muell. (ESEO), growing in Tunisia. The in vitro cytotoxic properties of the extracted EOs were also evaluated against two human cancer cell lines: breast carcinoma cell lines MDA-MB-231 and colorectal cancer cell lines SW620. The analysis by gas chromatography coupled with mass spectrometry (GC/MS) led to the identification of 32 compounds from the ETEO, with the dominant constituents being the monoterpenes trans-myrtanol (73.4 %) and myrtenol (4.7 %), and the apocarotene (E)-β-ionone (3.9 %). In the case of ESEO, 29 compounds were identified with trans-myrtanol (25.0 %), decanoic acid (22.1 %), nonanoic acid (9.8 %), γ-elemene (6.5 %), γ-maaliene (5.5 %), and α-terpineol (5.3 %) as the main components. The cytotoxicity of EOs against the two chosen cell lines was tested using Crystal Violet Staining (CVS) assay and 5-fluorouracil as a reference drug. The two EOs exhibited a significant dose-dependent inhibition against the viability of the used cell lines. Their inhibitory effects were particularly observed towards SW620 colon carcinoma cells with IC₅₀ values of 26.71±1.22 and 22.21±0.85 μg/mL, respectively, indicating that both oils were more cytotoxic for SW620 cells compared to MDA-MB-231 one.     

Essential Oil Variability and Biological Activities of Tetraclinis articulata (Vahl) Mast. Wood According to the Extraction Time

In the present work, the hydrodistillation (HD) and microwave‐assisted hydrodistillation (MAHD) kinetics of essential oil (EO) extracted from Tetraclinis articulata (Vahl ) Mast. wood was conducted, in order to assess the impact of extraction time and technique on chemical composition and biological activities. Gas chromatography (GC) and GC/mass spectrometry analyses showed significant differences between the extracted EOs, where each family class or component presents a specific kinetic according to extraction time, technique and especially for the major components: camphene, linalool, cedrol, carvacrol and α‐acorenol. Furthermore, our findings showed a high variability for both antioxidant and anti‐inflammatory activities, where each activity has a specific effect according to extraction time and technique. The highlighted variability reflects the high impact of extraction time and technique on chemical composition and biological activities, which led to conclude that we should select EOs to be investigated carefully depending on extraction time and technique, in order to isolate the bioactive components or to have the best quality of EO in terms of biological activities and preventive effects in food.     

Inhibitory effect of Ocotea quixos (Lam.) Kosterm. and Piper aduncum L. essential oils from Ecuador on West Nile virus infection

West Nile virus (WNV) is a mosquito-borne flavivirus responsible of neuroinvasive manifestations. Natural products are well-known for their biological activities and pharmaceutical application. In this study, the inhibitory effects of essential oils (EOs) of Ocotea quixos (Lam.) Kosterm. and Piper aduncum L. on WNV replication were investigated. WNV was incubated with EOs before adsorption on Vero cells, viral replication was carried out in the absence or presence of EO. Cells were exposed to EO before the adsorption of untreated-virus. GC-MS and GC-FID were used for chemical characterization of EOs. Cell protection from infection was observed for both EOs. P. aduncum EO was characterized by dillapiole as main compound (48.21%) and O. quixos EO by 1,8-cineole (39.15%). Further investigations, such as the study of molecular and cellular mechanisms of action and in vivo evaluation, should be performed on these essential oils to derive new potential drugs against WNV.     

Phytochemical and Biological Profile of Essential Oils of Elionurus muticus (Spreng.) Growing in Northeastern Argentina

The purpose of this study was to investigate essential oils (EOs) from leaves of Elionurus muticus growing in Northeastern Argentina regarding their physicochemical profiles as well as their biological potential. Roots of a selected E. muticus population were investigated too. For this purpose, EOs of fresh materials were obtained by steam distillation and the chemical composition was characterized by gas chromatography GC/MS-FID. Antibacterial, antioxidant and eco-toxicity activities of the essential oils (EOs) were tested by in vitro assays. The EOs showed three E. muticus chemotypes: citral (neral+geranial), acorenone+bisabolone, acorenone+geranial. EO of roots of citral population contains mainly acorenone derivatives. EOs have high antibacterial effect against Staphylococcus aureus, being found minor antibacterial effect against Gram-negative bacteria. The half-maximal inhibitory concentration of EOs against DPPH⋅ were 7.1–30.0 mg/mL and the eco-toxicity was high with LD₅₀ <39 μg/mL. Based on the findings, given the high variability in their chemical composition and biological activity of E. muticus EO and the promising yields, it could be potentially chosen for industrial applications.     

Cyclopentenone Derivatives and Polyhydroxylated Steroids from the Soft Coral Sinularia acuta

Four new polyhydroxylated steroids, 1 – 4 , and the racemic form of cyclopentenone 9 , together with four known steroids, 5 – 8 , one known cyclopentenone derivative, 10 , and one known butenolide derivative, 11 , were isolated from the soft coral Sinularia acuta collected from Weizhou Island of Guangxi Province, P. R. China. Their structures were elucidated on the basis of spectroscopic analyses and by comparison of the corresponding data with those previously reported. The cytotoxicities of the isolates 1 – 11 in vitro against the selected tumor cell lines HL‐60, HeLa, and K562 were evaluated. Compounds 2 and 5 showed potent cytotoxicities against HL‐60 cell lines with IC₅₀ values of 7.3 and 9.9 μM , respectively. Compounds 5 and 6 showed moderate activities against K562 cell lines with IC₅₀ values of 10.9 and 11.7 μM , respectively, while compounds 1, 2 , and 6 showed weak activities against HeLa cell lines with respective IC₅₀ values of 44.8, 27.1, and 18.2 μM . This is the first report on chemical and bioactivity research of S. acuta.     

Polycyclic Polyprenylated Acylphloroglucinols and Chromone O‐Glucosides from Hypericum henryi subsp. uraloides

Two new C(30)‐epimeric polycyclic polyprenylated acylphloroglucinols (PPAPs), named uralodins B and C ( 1 and 2 , resp.), were isolated from the aerial parts of Hypericum henryi subsp. uraloides together with two new chromone glucosides, urachromones A and B ( 3 and 4 , resp.), as well as 16 known compounds. Their structures were established by extensive NMR techniques and MS analysis. The epimers 1 and 2 always behaved like a single compound when examined by TLC, and were separated by HPLC. Their configuration was distinguished by comparative analysis of the NMR data with known analogues together with the ROESY experiment. All the isolated PPAPs were evaluated for their cytotoxic activities against HepG2, SGC7901, HL‐60, and K562 cell lines. Compound 1 showed modest cytotoxic activities against SGC7901 and HL‐60 cell lines, and 2 showed modest cytotoxic activities against HepG2, SGC7901, HL‐60, and K562 cell lines.     

Design,synthesis, and quantitative structure–activity relationship of cytotoxic γ-carboline derivatives

Three series of γ-carboline derivatives were designed and synthesized. All the compounds were tested for their cytotoxic activities in vitro against five human tumor cell lines (A549, SGC, HCT116, MCF-7, K562) and one multi-drug resistant subline (K562R). Most compounds showed moderate to potent cytotoxic activities against the tested cell lines. Sulfonate 11f exhibited more potent cytotoxic activities against almost all of the tested cells in comparison with the positive control, taxol, with IC₅₀ values ranging from 0.15 to 4.5 μM. The structure–activity relationships were discussed and a statistically reliable QSAR model (r² = 0.936, q² = 0.581) was established by the CoMFA analysis performed using the cytotoxic data against K562 cell line as a template.     

Essential Oil of Deverra tortuosa Aerial Parts: Detailed Chemical Profile,Allelopathic, Antimicrobial,and Antioxidant Activities

Essential oils (EOs) are a promising group of natural products of the aromatic plants due to their various biological effects such as allelopathic, antioxidant, antimicrobial activities. The present study aimed to construct the detailed chemical profile of the EO derived from Deverra tortuosa aerial parts along with assessing its allelopathic, antimicrobial, and antioxidant potentialities. The EO was extracted by hydrodistillation and analyzed via gas chromatography-mass spectrometry (GC/MS). The allelopathic activity of the EO was assessed against the germination and seedling growth of the weed Chenopodium murale. Also, the EO was tested against five microbes. The antioxidant activity was determined using the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS). The GC/MS analysis of EO revealed the presence of 86 compounds with a preponderance of oxygenated sesquiterpenes and monoterpene hydrocarbons. Widdrol, β-phellandrene, piperitol, cubedol, α-terpinene, (E)-10-heptadecen-8-ynoic acid methyl ester, citronellyl tiglate, and m-cymene were the major compounds. A comparative profile was established between the EOs constituents of our study with the documented EOs of D. tortuosa and the other Deverra species around the world via agglomerative hierarchical clustering (AHC) and principal components analysis (PCA). The EO showed a substantial allelopathic activity against C. murale, as well as it showed considerable antimicrobial and antioxidant activities. Thereby, the EO of D. tortuosa could be considered as a promising environmental-friendly bioherbicide against weeds. Also, it could be integrated into food preservation due to its potent antimicrobial and antioxidant activities. However, further study is recommended for more characterization of the major compounds and evaluation of their activities, either singular or synergistic, and assess their efficiency and biosafety.     

Chemical Composition,Antimicrobial and Insecticidal Activities of Flowers Essential Oils of Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm. from Martinique Island

Alpinia species, used as ornamental plants and flavoring agents, are renowned for their therapeutic properties and their subsequent use in traditional medicines throughout the world. Alpinia zerumbet (Pers .) B.L.Burtt & R.M.Sm . is the most common Alpinia species encountered in Martinique. Several essential oils (EOs) obtained by hydrodistillation of A. zerumbet flowers collected in various locations on the island at different seasons were analysed to evaluate the influence of the collection period and area on the EOs’ chemical compositions and to assess their bioactivity. A combination of GC‐FID and GC/MS techniques was used to examine the volatile constituents, leading to the identification of a total of 71 components accounting for 97.8 – 99.3% of the respective total GC‐FID areas: among them, nineteen compounds were characterized for the first time in A. zerumbet EOs. The antimicrobial activity of these EOs was assessed against eight bacterial, yeast and fungal strains and two multi‐resistant strains: some significant bacteriostatic and fungistatic activities of A. zerumbet flower oils were evidenced. Finally, an interesting insecticidal activity of the flower EO was highlighted for the first time against Aedes aegypti.     

Interference of Seasonal Variation on the Antimicrobial and Cytotoxic Activities of the Essential Oils from the Leaves of Iryanthera polyneura in the Amazon Rain Forest

The essential oils (EOs) obtained from the leaves of Iryanthera polyneura Ducke trees was chemically Assessed and tested for the ability of inhibiting the growth of Candida albicans, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Streptococcus mutans and S. sanguinis. The oil was also tested against breast (MCF‐7) and prostate (PC‐3) cancer cell lines. Minimum bactericidal concentrations (MBCs) and 50 % inhibition concentrations (IC₅₀) values were obtained. EOs were active against Gram‐positive bacteria. Spathulenol, α‐cadinol and τ‐muurolol were major components of EOs. The oils showed a higher cytotoxicity against PC‐3 than MCF‐7 cells, although the oils were active against both cell types. Oils obtained from leaves collected in the dry season were more active against E. faecalis, S. aureus and PC‐3, while the oils obtained from leaves collected in the rainy season were more active against S. mutans, S. sanguinis and MCF‐7. The antibacterial and cytotoxic activities of the essential oils from the leaves of I. polyneura are related to the seasonal climate variation and are influenced by compounds that are minor components of the oils.     

Phytochemical evaluation and in vitro antifungal activities of Melaleuca styphelioides leaves: comparison between volatile and non-volatile extracts

Abstract

Melaleuca styphelioides is considered as medicinal plant. This study was carried out to evaluate for the first time the phytochemical composition and to compare the antifungal activities of essential oil (EOs), methanol and aqueous extracts of M. styphelioides Sm. leaves against three fungi (Aspergillus niger, Rhizopus nigricans and Penicillium digitatum). A total of 10 components of the EO were identified, with the principal compound being methyl eugenol (87.2%). Results of the phytochemical analysis of leaves extract exhibited the presence of different phytoconstituents (phenolic compounds, flavonoids, tannins and anthocyanins). Volatile and non-volatile extracts were found to express dose-dependent inhibition against all tested fungi. Indeed, the EO oil showed significant inhibition of fungal growth and the IC₅₀ was 2.08?µL/mL for A. niger indicating that M. styphelioides leaf EO was particularly effective against this pathogen. The most susceptible species for the aqueous extract was P. digitatum (IC₅₀= 9.54?mg/mL) whereas R. nigricans was found to be more susceptible to the methanolic extract (IC₅₀= 8.31?mg/mL). Thus, the EO and aqueous as well as methanol extracts of M. styphelioides leaves possess antifungal activity and hence, it can be suggested for use in the food or pharmaceutical industries as an alternative to chemical preservatives.     

Chemical Composition and Antimicrobial Activity of the Essential Oil of Ruta chalepensis L. Growing Wild in Lebanon

The essential oils (EOs) isolated from the fresh aerial parts of Ruta chalepensis L. collected in North Lebanon were obtained by solvent‐free microwave extraction (Milestone®), yielding 0.12% EO from both the leaves and a mixture of stems and leaves. The EOs were characterized by GC/MS analysis, and 27 components were identified, which were primarily ketones (88.0–93.2%). The main components were nonan‐2‐one and undecan‐2‐one. The antimicrobial activity of the EOs against a Gram‐positive and a Gram‐negative bacterium, a yeast, and a dermatophyte was evaluated using the broth‐microdilution technique and expressed as minimal inhibitory concentration (MIC). The EOs revealed moderate in vitro antifungal activity against Trichophyton rubrum and Candida albicans.     

Influence of Environmental Factors on Essential Oil Variability in Origanum compactum Benth. Growing Wild in Morocco

The present study aimed to evaluate the influence of environmental factors on essential oils (EOs) composition of Origanum compactum populations sampled all over the distribution area of the species in Morocco, and to determine the extent of the chemical profiles throughout the geographical distribution of the species. The chemical compositions were submitted to canonical correlation analysis and canonical discriminant analysis that indicated a significant relationship between oil components and some environmental factors. According to their chemical composition and edapho‐climatic characteristics, two major groups of populations were differentiated. The first group was composed of samples growing in regions with humid climate, clayey, sandy, and alkaline soils. These samples showed high thymol, α‐terpineol, linalool, and carvacryl methyl oxide content. The second group consisted of plants belonging to semi‐arid climate, and growing at high altitudes and silty soils. These samples were characterized by high carvacrol, α‐thujene, α‐terpinene, and myrcene content. However, populations exposed to sub‐humid climate, appeared less homogeneous and belong mainly either to the first or second group. A significant correlation between some edaphic factors (pH, K₂O content, soil texture) and the EOs yield of O. compactum plants was evidenced. In spite of the correlation obtained for the oil composition with edapho‐climatic factors and the variance explained by the environmental data set, the observed EO diversity might be also genetically determined.     

Trypanocidal,trichomonacidal and cytotoxic components of cultivated Artemisia absinthium Linnaeus (Asteraceae) essential oil

Artemisia absinthium is an aromatic and medicinal plant of ethnopharmacological interest and it has been widely studied. The use ofA. absinthium based on the collection of wild populations can result in variable compositions of the extracts and essential oils (EOs). The aim of this paper is the identification of the active components of the vapour pressure (VP) EO from a selected and cultivated A. absinthiumSpanish population (T2-11) against two parasitic protozoa with different metabolic pathways: Trypanosoma cruzi andTrichomonas vaginalis. VP showed activity on both parasites at the highest concentrations. The chromatographic fractionation of the VP T2-11 resulted in nine fractions (VLC1-9). The chemical composition of the fractions and the antiparasitic effects of fractions and their main compounds suggest that the activity of the VP is related with the presence oftrans-caryophyllene and dihydrochamazulene (main components of fractions VLC1 and VLC2 respectively). Additionally, the cytotoxicity of VP and fractions has been tested on several tumour and no tumour human cell lines. Fractions VLC1 and VLC2 were not cytotoxic against the nontumoural cell line HS5, suggesting selective antiparasitic activity for these two fractions. The VP and fractions inhibited the growth of human tumour cell lines in a dose-dependent manner.     

Essential Oils from Piper caldense C. DC. and Piper xylosteoides (Kunth) Steud.: Seasonal Variation of the Chemical Composition and Antimicrobial Activity

The essential oils (EOs) chemical composition can be affected by several environmental factors, impacting their desired biological activities. In this sense, this work aimed to evaluate the seasonal variation of the chemical composition and antimicrobial activity of Piper caldense and Piper xylosteoides leaves EOs. Their chemical composition was determined by GC/MS and GC-FID analyses, resulting in the identification of eighty compounds. P. caldense EOs were mainly consisted of sesquiterpene hydrocarbons, whereas in P. xylosteoides EOs, monoterpene hydrocarbons were predominant. EOs from both species strongly inhibited B. subtilis (MIC=0.25 mg mL⁻¹), while only P. caldense EOs showed strong activity against S. aureus (MIC=0.50 mg mL⁻¹). P. caldense spring EO showed the broadest spectrum of antimicrobial action amongst all samples. For each species, PCA seasonally differentiated EOs chemical composition. In addition, as expected, PCA of all samples showed a distinction between the two species. This study has successfully demonstrated the importance of evaluating the seasonal variation of EOs chemical composition and antimicrobial activity in obtaining a product with the desired properties.     

Essential Oil from Bark of Aniba parviflora (Meisn.) Mez (Lauraceae) Reduces HepG2 Cell Proliferation and Inhibits Tumor Development in a Xenograft Model

Aniba parviflora (Meisn .) Mez (Lauraceae) is an aromatic plant of the Amazon rainforest, which has a tremendous commercial value in the perfumery industry; it is popularly used as flavoring sachets and aromatic baths. In Brazilian folk medicine, A. parviflora is used to treat victims of snakebites. Herein, we analyzed the chemical composition of A. parviflora bark essential oil (EO) and its effect on the growth of human hepatocellular carcinoma HepG2 cells in vitro and in vivo. EO was obtained by hydrodistillation and characterized by GC-MS and GC-FID. The main constituents of EO were linalool (16.3±3.15), α-humulene (14.5±2.41 %), δ-cadinene (10.2±1.09 %), α-copaene (9.51±1.12 %) and germacrene B (7.58±2.15 %). Initially, EO's cytotoxic effect was evaluated against five cancer cell lines (HepG2, MCF-7, HCT116, HL-60 and B16-F10) and one non-cancerous one (MRC-5), using the Alamar blue method after 72 h of treatment. The calculated IC₅₀ values were 9.05, 22.04, >50, 15.36, 17.57, and 30.46 μg/mL, respectively. The best selectivity was for HepG2 cells with a selective index of 3.4. DNA Fragmentation and cell cycle distribution were quantified in HepG2 cells by flow cytometry after a treatment period of 24 and 48 h. The effect of EO on tumor development in vivo was evaluated in a xenograft model using C.B-17 SCID mice engrafted with HepG2 cells. In vivo tumor growth inhibition of HepG2 xenograft at the doses of 40 and 80 mg/kg were 12.1 and 62.4 %, respectively.