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4 pages, 196 KiB

Open AccessEditorial

Biological Activity of Essential Oils

by Francesca Mancianti and Valentina Virginia Ebani

Molecules 2020, 25(3), 678; https://doi.org/10.3390/molecules25030678 - 5 Feb 2020

Cited by 70 | Viewed by 5190

Abstract

Essential oils (EOs) have for a long time been recognized to possess several different biological activities [...] Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

Research

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12 pages, 781 KiB

Open AccessArticle

Bigger Data Approach to Analysis of Essential Oils and Their Antifungal Activity against Aspergillus niger, Candida albicans, and Cryptococcus neoformans

by Chelsea N. Powers, Prabodh Satyal, John A. Mayo, Hana McFeeters and Robert L. McFeeters

Molecules 2019, 24(16), 2868; https://doi.org/10.3390/molecules24162868 - 7 Aug 2019

Cited by 22 | Viewed by 4934

Abstract

With increasing drug resistance and the poor state of current antifungals, the need for new antifungals is urgent and growing. Therefore, we tested a variety of essential oils for antifungal activity. We report the minimum inhibitory concentrations (MIC) values for a common set [...] Read more.

With increasing drug resistance and the poor state of current antifungals, the need for new antifungals is urgent and growing. Therefore, we tested a variety of essential oils for antifungal activity. We report the minimum inhibitory concentrations (MIC) values for a common set of 82 essential oils against Aspergillus niger, Candida albicans, and Cryptococcus neoformans. Generally, narrow-spectrum activity was found. However, C. neoformans was much more susceptible to inhibition by essential oils with over one-third of those tested having MIC values below 160 ppm. GC-MS analysis showed the essential oils to be chemically diverse, yet, the potentially active major constituents typically fell into a few general categories (i.e., terpenes, terpenoids, terpenols). While essential oils remain a rich source of potential antifungals, focus should shift to prioritizing activity from novel compounds outside the commonalities reported here, instead of simply identifying antifungal activity. Further, capitalizing on bigger data approaches can provide significant returns in expediting the identification of active components. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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10 pages, 1000 KiB

Open AccessArticle

Liquid and Vapour Phase of Lavandin (Lavandula × intermedia) Essential Oil: Chemical Composition and Antimicrobial Activity

by Stefania Garzoli, Giovanni Turchetti, Pierluigi Giacomello, Antonio Tiezzi, Valentina Laghezza Masci and Elisa Ovidi

Molecules 2019, 24(15), 2701; https://doi.org/10.3390/molecules24152701 - 25 Jul 2019

Cited by 34 | Viewed by 5823

Abstract

Essential oils from Lavandula genus and the obtained hybrids are widely used for different purposes such as perfume production in the cosmetic field and for its biological properties. This is the first study on the liquid and vapour phase of Lavandula × intermedia [...] Read more.

Essential oils from Lavandula genus and the obtained hybrids are widely used for different purposes such as perfume production in the cosmetic field and for its biological properties. This is the first study on the liquid and vapour phase of Lavandula × intermedia “Grosso” essential oil grown in the Lazio Region, Italy, investigated using headspace coupled to gas chromatography and mass spectrometry (HS-GC/MS). The results showed the most abundant components were linalool and linalyl acetate, followed by 1,8-cineole and terpinen-4-ol, while lavandulyl acetate and borneol were identified as minor compounds, maintaining the same proportion in both the liquid and vapour phase. Furthermore, we tested lavandin liquid and vapour phase essential oil on gram-negative bacteria (Escherichia coli, Acinetobacter bohemicus, and Pseudomonas fluorescens) and gram-positive bacteria (Bacillus cereus and Kocuria marina). Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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15 pages, 2811 KiB

Open AccessArticle

Extraction, Chemical Composition, and Anticancer Potential of Origanum onites L. Essential Oil

by Katerina Spyridopoulou, Eleni Fitsiou, Eleni Bouloukosta, Angeliki Tiptiri-Kourpeti, Manolis Vamvakias, Antigoni Oreopoulou, Eleni Papavassilopoulou, Aglaia Pappa and Katerina Chlichlia

Molecules 2019, 24(14), 2612; https://doi.org/10.3390/molecules24142612 - 18 Jul 2019

Cited by 61 | Viewed by 6681

Abstract

Origanum species are plants rich in volatile oils that are mainly used for culinary purposes. In recent years, there has been a growing interest in the biological activities of their essential oils. Origanum onites L. is a plant mainly found in Greece, Turkey, [...] Read more.

Origanum species are plants rich in volatile oils that are mainly used for culinary purposes. In recent years, there has been a growing interest in the biological activities of their essential oils. Origanum onites L. is a plant mainly found in Greece, Turkey, and Sicily, whose oil is rich in carvacrol, a highly bioactive phytochemical. The aim of this study was to analyze the chemical composition of Origanum onites essential oil (OOEO), and investigate its potential anticancer effects in vitro and in vivo. GC/MS analysis identified carvacrol as OOEO’s main constituent. In vitro antiproliferative activity was assayed with the sulforhodamine B (SRB) assay against human cancer cell lines from four tumor types. HT-29, a colorectal cancer cell line, was the most sensitive to the antiproliferative activity of OOEO. Wound-healing assay and Annexin V-PI staining were employed to investigate the antimigratory and the pro-apoptotic potential of OOEO, respectively, against human (HT-29) and murine (CT26) colon cancer cells. Notably, OOEO attenuated migration and induced apoptosis-related morphological changes in both cell lines. Prophylactic oral administration of the oil in a BALB/c experimental mouse model inhibited the growth of syngeneic CT26 colon tumors. As far as we know, this is the first report on the antitumor potential of orally administered OOEO. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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16 pages, 1984 KiB

Open AccessArticle

Essential Oil of Algerian Eryngium campestre: Chemical Variability and Evaluation of Biological Activities

by Ali Medbouhi, Fethi Benbelaïd, Nassim Djabou, Claire Beaufay, Mourad Bendahou, Joëlle Quetin-Leclercq, Aura Tintaru, Jean Costa and Alain Muselli

Molecules 2019, 24(14), 2575; https://doi.org/10.3390/molecules24142575 - 15 Jul 2019

Cited by 29 | Viewed by 4072

Abstract

The chemical composition of essential oils extracted from aerial parts of Eryngium campestre collected in 37 localities from Western Algeria was characterized using GC-FID and GC/MS analyses. Altogether, 52 components, which accounted for 70.1 to 86.8% of the total composition oils were identified. [...] Read more.

The chemical composition of essential oils extracted from aerial parts of Eryngium campestre collected in 37 localities from Western Algeria was characterized using GC-FID and GC/MS analyses. Altogether, 52 components, which accounted for 70.1 to 86.8% of the total composition oils were identified. The main compounds were Germacrene D (0.4–53.4%), Campestrolide (1.6–35.3%), Germacrene B (0.2–21.5%), Myrcene (0.1–8.4%), α-Cadinol (0.2–7.6%), Spathulenol (0.1–7.6%), Eudesma-4(15)-7-dien-1-β-ol (0.1–7.6%) and τ-Cadinol (0.3–5.5%). The chemical compositions of essential oils obtained from separate organs and during the complete vegetative cycle of the plant were also studied. With the uncommon 17-membered ring lactone named Campestrolide as the main component, Algerian E. campestre essential oils exhibited a remarkable chemical composition. A study of the chemical variability using statistical analysis allowed the discrimination of two main clusters according to the geographical position of samples. The study contributes to the better understanding of the relationship between the plant and its environment. Moreover, the antimicrobial activity of the essential oil was assessed against twelve strains bacteria and two yeasts involved in foodborne and nosocomial infections using paper disc diffusion and dilution agar assays. The in vitro study demonstrated a strong activity against Gram-positive strains such as S. aureus, B. cereus, and E. faecalis. The cytotoxicity and antiparasitic activities (on Lmm and Tbb) of the collective essential oil and one sample rich in campestrolide, as well as some enriched fractions or fractions containing other terpenic compounds, were also analyzed. Campestrolide seems to be one compound responsible for the cytotoxic and antileishmanial effect, while myrcene or/and trans-β-farnesene have a more selective antitrypanosomal activity. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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13 pages, 5328 KiB

Open AccessArticle

Endlicheria bracteolata (Meisn.) Essential Oil as a Weapon Against Leishmania amazonensis: In Vitro Assay

by Mariana Margatto Rottini, Ana Claudia Fernandes Amaral, José Luiz Pinto Ferreira, Edinilze Souza Coelho Oliveira, Jefferson Rocha de Andrade Silva, Noemi Nosomi Taniwaki, Arith Ramos dos Santos, Fernando Almeida-Souza, Celeste da Silva Freitas de Souza and Kátia da Silva Calabrese

Molecules 2019, 24(14), 2525; https://doi.org/10.3390/molecules24142525 - 10 Jul 2019

Cited by 20 | Viewed by 3411

Abstract

The difficulties encountered and the numerous side effects present in the treatment of cutaneous leishmaniasis have encouraged the research for new compounds that can complement or replace existing treatment. The growing scientific interest in the study of plants, which are already used in [...] Read more.

The difficulties encountered and the numerous side effects present in the treatment of cutaneous leishmaniasis have encouraged the research for new compounds that can complement or replace existing treatment. The growing scientific interest in the study of plants, which are already used in folk remedies, has led our group to test Endlicheria bracteolata essential oil against Leishmania amazonensis. Several species of the Lauraceae family, or their compounds, have relevant antiprotozoal activities Therefore, the biological potential on L. amazonensis forms from the essential oil of Endlicheria bracteolata leaves was verified for the first time in that work. The antileishmanial activity was evaluated against promastigotes and intracellular amastigotes, and cytotoxicity were performed with J774.G8, which were incubated with different concentrations of E. bracteolata essential oil. Transmission electron microscopy and flow cytometry were performed with E. bracteolata essential oil IC₅₀. Promastigote forms showed E. bracteolata essential oil IC₅₀ of 7.945 ± 1.285 µg/mL (24 h) and 6.186 ± 1.226 µg/mL (48 h), while for intracellular amastigote forms it was 3.546 ± 1.184 µg/mL (24 h). The CC₅₀ was 15.14 ± 0.090 µg/mL showing that E. bracteolata essential oil is less toxic to macrophages than to parasites. Transmission electron microscopy showed that E. bracteolata essential oil treatment is capable of inducing mitochondrial damage to promastigote and intracellular amastigote forms, while flow cytometry showed ΔѰm disruption in treated parasites. These results could bring about new possibilities to develop products based on E. bracteolata essential oil to treat cutaneous leishmaniasis, especially for people who cannot receive the conventional therapy. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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13 pages, 2878 KiB

Open AccessArticle

Peppermint Essential Oil-Doped Hydroxyapatite Nanoparticles with Antimicrobial Properties

by Monica Luminita Badea, Simona Liliana Iconaru, Andreea Groza, Mariana Carmen Chifiriuc, Mircea Beuran and Daniela Predoi

Molecules 2019, 24(11), 2169; https://doi.org/10.3390/molecules24112169 - 9 Jun 2019

Cited by 41 | Viewed by 6520

Abstract

This study aimed at developing an antimicrobial material based on hydroxyapatite (HAp) and peppermint essential oil (P-EO) in order to stimulate the antimicrobial activity of hydroxyapatite. The molecular spectral features and morphology of the P-EO, HAp and hydroxyapatite coated with peppermint essential oil [...] Read more.

This study aimed at developing an antimicrobial material based on hydroxyapatite (HAp) and peppermint essential oil (P-EO) in order to stimulate the antimicrobial activity of hydroxyapatite. The molecular spectral features and morphology of the P-EO, HAp and hydroxyapatite coated with peppermint essential oil (HAp-P) were analyzed using Fourier-transform infrared (FTIR) spectroscopy and scanning electron microscopy (SEM). The coating of the HAp with the P-EO did not affect the ellipsoidal shape of the nanoparticles. The overlapping of IR bands of P-EO and HAp in the HAp-P spectrum determined the formation of the broad molecular bands that were observed in the spectral regions of 400–1000 cm⁻¹ and 1000–1200 cm⁻¹. The antibacterial activity of the P-EO, HAp and HAp-P were also tested against different Gram-positive bacteria (methicillin-resistant Staphylococcus aureus (MRSA) 388, S. aureus ATCC 25923, S. aureus ATCC 6538, E. faecium DSM 13590), Gram-negative bacteria (Escherichia coli ATCC 25922, E. coli C5, P. aeruginosa ATCC 27853, P. aeruginosa ATCC 9027) and a fungal strain of Candida parapsilosis. The results of the present study revealed that the antimicrobial activity of HAp-P increased significantly over that of HAp. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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14 pages, 1603 KiB

Open AccessArticle

Exploring Ecological Alternatives for Crop Protection Using Coriandrum sativum Essential Oil

by Renata Maria Sumalan, Ersilia Alexa, Iuliana Popescu, Monica Negrea, Isidora Radulov, Diana Obistioiu and Ileana Cocan

Molecules 2019, 24(11), 2040; https://doi.org/10.3390/molecules24112040 - 28 May 2019

Cited by 23 | Viewed by 3725

Abstract

Essential oils (EOs) are a natural source of active compounds with antifungal, antimycotoxigenic, and herbicidal potential, and have been successfully used in organic agriculture, instead of chemical compounds obtained by synthesis, due to their high bioactivity and the absence of toxicity. The aim [...] Read more.

Essential oils (EOs) are a natural source of active compounds with antifungal, antimycotoxigenic, and herbicidal potential, and have been successfully used in organic agriculture, instead of chemical compounds obtained by synthesis, due to their high bioactivity and the absence of toxicity. The aim of this study was to highlight the importance of Coriandrum sativum essential oil (CEO) as a potential source of bioactive constituents and its applications as an antifungal and bioherbicidal agent. The CEO was obtained by steam distillation of coriander seeds and GC-MS technique was used to determine the chemical composition. Furthermore, in vitro tests were used to determine the antifungal potential of CEO on Fusarium graminearum mycelia growth through poisoned food technique, resulting in the minimum fungistatic (MCFs) and fungicidal concentrations (MCFg). The antifungal and antimycotoxigenic effect of CEO was studied on artificially contaminated wheat seeds with F. graminearum spores. Additionally, the herbicidal potential of CEO was studied by fumigating monocotyledonous and dicotyledonous weed seeds, which are problematic in agricultural field crops in Romania. The in vitro studies showed the antifungal potential of CEO, with a minimum concentration for a fungistatic effect of 0.4% and the minimum fungicidal concentration of 0.6%, respectively. An increase in the antifungal effects was observed in the in vivo experiment with F. graminearum, where a mixture of CEO with Satureja hortensis essential oil (SEO) was used. This increase is attributed to the synergistic effect of both EOs. Moreover, the synthesis of deoxynivalenol (DON)-type mycotoxins was found to be less inhibited. Hence, CEO has shown an herbicidal potential on weed seeds by affecting inhibition of germination. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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12 pages, 1293 KiB

Open AccessArticle

Effect of Clove and Thyme Essential Oils on Candida Biofilm Formation and the Oil Distribution in Yeast Cells

by Katarzyna Rajkowska, Paulina Nowicka-Krawczyk and Alina Kunicka-Styczyńska

Molecules 2019, 24(10), 1954; https://doi.org/10.3390/molecules24101954 - 21 May 2019

Cited by 48 | Viewed by 6733

Abstract

Candida biofilm structure is particularly difficult to eradicate, since biofilm is much more resistant to antifungal agents than planktonic cells. In this context, a more effective strategy seems to be the prevention of biofilm formation than its eradication. The aim of the study [...] Read more.

Candida biofilm structure is particularly difficult to eradicate, since biofilm is much more resistant to antifungal agents than planktonic cells. In this context, a more effective strategy seems to be the prevention of biofilm formation than its eradication. The aim of the study was to examine whether the process of initial colonization of materials (glass, polyethylene terephthalate, polypropylene) by food-borne Candida sp. can be impeded by clove and thyme essential oils, used at their minimal inhibitory concentrations. In the presence of clove oil, 68.4–84.2% of the yeast tested showed a statistically significant reduction in biofilm formation, depending on the material. After treatment with thyme oil, statistically significant decrease in biofilm cell numbers was observed for 63.2–73.7% of yeasts. Confocal laser scanning microscopy showed diverse compounds of clove and thyme oils that were disparately located in C. albicans cell, on a cell wall and a cell membrane, in cytoplasm, and in vacuoles, depicting the multidirectional action of essential oils. However, essential oils that were used in sub-inhibitory concentration were sequestrated in the yeast vacuoles, which indicate the activation of Candida defense mechanisms by cell detoxification. Clove and thyme essential oils due to their anti-biofilm activity can be efficiently used in the prevention of the tested abiotic surfaces colonization by Candida sp. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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11 pages, 605 KiB

Open AccessArticle

Chemical Composition, Antioxidant, and Antimicrobial Activities of Vetiveria zizanioides (L.) Nash Essential Oil Extracted by Carbon Dioxide Expanded Ethanol

by Andreea David, Fang Wang, Xiaoming Sun, Hongna Li, Jieru Lin, Peilei Li and Gang Deng

Molecules 2019, 24(10), 1897; https://doi.org/10.3390/molecules24101897 - 17 May 2019

Cited by 40 | Viewed by 5695

Abstract

In the present study, the composition of essential oil isolated from the roots of Vetiveria zizanioides (L.) Nash, harvested in China, was studied, along with the bioactivities. A green novel method using an eco-friendly solvent, CO₂-pressurized ethanol, or carbon dioxide expanded [...] Read more.

In the present study, the composition of essential oil isolated from the roots of Vetiveria zizanioides (L.) Nash, harvested in China, was studied, along with the bioactivities. A green novel method using an eco-friendly solvent, CO₂-pressurized ethanol, or carbon dioxide expanded ethanol (CXE) was employed to isolate the essential oil from the root of Vetiveria zizanioides (L.) Nash with the purpose of replacing the traditional method and supercritical fluid extraction (SFE). After investigating the major operating factors of CXE, the optimal conditions were obtained as follows: 8.4 MPa, 50 °C, 5 mL/min ethanol, and 0.22 mole fraction of CO₂, presenting an extraction oil that ranged from 5.12% to 7.42%, higher than that of hydrodistillation (HD) or indirect vapor distillation (IVD). The Gas Chromatography-Mass Spectrometry (GC-MS) analysis showed that three major components, including valerenol (18.48%), valerenal (10.21%), and β-Cadinene (6.23%), are found in CXE oil, while a total of 23 components were identified, 48 components less than using conventional hydrodistillation. Furthermore, the antimicrobial activities of root oils were evaluated by the microdilution method, which showed that CXE oil exhibited an ability against Gram-positive bacteria, especially Staphylococcus aureus, approximately equivalent to traditional samples. Additionally, the DPPH free radical scavenging assay demonstrated that the antioxidant abilities of root oils were sorted in the descending order: IVD > HD > CXE > SFE. In conclusion, after a comprehensive comparison with the conventional methods, the CXE-related technique might be a promising green manufacturing pattern for the production of quality vetiver oil, due to the modification of ethanol by the variable addition of non-polar compressible CO₂, ultimately resulting in a prominent dissolving capability for the extraction of vetiver solutes. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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16 pages, 2251 KiB

Open AccessArticle

Biological Activities and Chemical Constituents of Essential Oils from Piper cubeba Bojer and Piper nigrum L.

by Yusuf Andriana, Tran Dang Xuan, Tran Ngoc Quy, Hoang-Dung Tran and Quang-Tri Le

Molecules 2019, 24(10), 1876; https://doi.org/10.3390/molecules24101876 - 15 May 2019

Cited by 47 | Viewed by 9577

Abstract

In this study, we evaluated antioxidant, antihyperuricemic, and herbicidal activities of essential oils (EOs) from Piper cubeba Bojer and Piper nigrum L.; two pepper species widely distributed in tropics, and examined their chemical compositions. Dried berries of P. cubeba and P. nigrum were [...] Read more.

In this study, we evaluated antioxidant, antihyperuricemic, and herbicidal activities of essential oils (EOs) from Piper cubeba Bojer and Piper nigrum L.; two pepper species widely distributed in tropics, and examined their chemical compositions. Dried berries of P. cubeba and P. nigrum were hydro-distilled to yield essential oil (EO) of 1.23 and 1.11% dry weight, respectively. In the antioxidant assay, the radical scavenging capacities of P. cubeba EO against DPPH and ABTS free radicals were 28.69 and 24.13% greater than P. nigrum, respectively. In the antihyperuricemic activity, P. cubeba EO also exhibited stronger inhibitory effects on xanthine oxidase (IC₅₀ = 54.87 µg/mL) than P. nigrum EO (IC₅₀ = 77.11 µg/mL). In the herbicidal activity, P. cubeba EO showed greater inhibition on germination and growth of Bidens pilosa and Echinochloa crus-galli than P. nigrum EO. Besides, P. cubeba EO decreased 15.98–73.00% of photosynthesis pigments of B. pilosa and E. crus-galli, while electrolyte leakages, lipid peroxidations, prolines, phenolics, and flavonoids contents were increased 10.82–80.82% at 1.93 mg/mL dose. Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) analyses revealed that P. nigrum and P. cubeba EOs principally possessed complex mixtures of monoterpenes and sesquiterpenes. Terpinen-4-ol (42.41%), α-copaene (20.04%), and γ-elemene (17.68%) were the major components of P. cubeba EO, whereas β-caryophyllene (51.12%) and β-thujene (20.58%) were the dominant components of P. nigrum EO. Findings of this study suggest both P. cubeba and P. nigrum EOs were potential to treat antioxidative stress and antihyperuricemic related diseases. In addition, the EOs of the two plants may be useful to control B. pilosa and E. crus-galli, the two invasive and problematic weeds in agriculture practice. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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17 pages, 8831 KiB

Open AccessArticle

Neutrophil Immunomodulatory Activity of Natural Organosulfur Compounds

by Igor A. Schepetkin, Liliya N. Kirpotina, Andrei I. Khlebnikov, Narayanaganesh Balasubramanian and Mark T. Quinn

Molecules 2019, 24(9), 1809; https://doi.org/10.3390/molecules24091809 - 10 May 2019

Cited by 39 | Viewed by 4786

Abstract

Organosulfur compounds are bioactive components of garlic essential oil (EO), mustard oil, Ferula EOs, asafoetida, and other plant and food extracts. Traditionally, garlic (Allium sativum) is used to boost the immune system; however, the mechanisms involved in the putative immunomodulatory effects [...] Read more.

Organosulfur compounds are bioactive components of garlic essential oil (EO), mustard oil, Ferula EOs, asafoetida, and other plant and food extracts. Traditionally, garlic (Allium sativum) is used to boost the immune system; however, the mechanisms involved in the putative immunomodulatory effects of garlic are unknown. We investigated the effects of garlic EO and 22 organosulfur compounds on human neutrophil responses. Garlic EO, allyl propyl disulfide, dipropyl disulfide, diallyl disulfide, and allyl isothiocyanate (AITC) directly activated Ca²⁺ flux in neutrophils, with the most potent being AITC. Although 1,3-dithiane did not activate neutrophil Ca²⁺ flux, this minor constituent of garlic EO stimulated neutrophil reactive oxygen species (ROS) production. In contrast, a close analog (1,4-dithiane) was unable to activate neutrophil ROS production. Although 1,3-dithiane-1-oxide also stimulated neutrophil ROS production, only traces of this oxidation product were generated after a 5 h treatment of HL60 cells with 1,3-dithiane. Evaluation of several phosphatidylinositol-3 kinase (PI3K) inhibitors with different subtype specificities (A-66, TGX 221, AS605240, and PI 3065) showed that the PI3K p110δ inhibitor PI 3065 was the most potent inhibitor of 1,3-dithiane-induced neutrophil ROS production. Furthermore, 1,3-dithiane enhanced the phosphorylation of extracellular signal-regulated kinase 1/2 (ERK1/2), glycogen synthase kinase 3 α/β (GSK-3α/β), and cAMP response element binding (CREB) protein in differentiated neutrophil-like HL60 cells. Density functional theory (DFT) calculations confirmed the reactivity of 1,3-dithiane vs. 1,4-dithiane, based on the frontier molecular orbital analysis. Our results demonstrate that certain organosulfur compounds can activate neutrophil functional activity and may serve as biological response modifiers by augmenting phagocyte functions. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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12 pages, 716 KiB

Open AccessArticle

Chemical Composition and Biological Activity of Five Essential Oils from the Ecuadorian Amazon Rain Forest

by Paco Noriega, Alessandra Guerrini, Gianni Sacchetti, Alessandro Grandini, Edwin Ankuash and Stefano Manfredini

Molecules 2019, 24(8), 1637; https://doi.org/10.3390/molecules24081637 - 25 Apr 2019

Cited by 31 | Viewed by 6186

Abstract

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 [...] Read more.

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. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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10 pages, 2771 KiB

Open AccessArticle

Antibacterial Activity and Mechanisms of Essential Oil from Citrus medica L. var. sarcodactylis

by Ze-Hua Li, Ming Cai, Yuan-Shuai Liu, Pei-Long Sun and Shao-Lei Luo

Molecules 2019, 24(8), 1577; https://doi.org/10.3390/molecules24081577 - 22 Apr 2019

Cited by 181 | Viewed by 9065

Abstract

In this work, antibacterial activity of finger citron essential oil (FCEO, Citrus medica L. var. sarcodactylis) and its mechanism against food-borne bacteria were evaluated. A total of 28 components in the oil were identified by gas chromatography-mass spectrometry, in which limonene (45.36%), [...] Read more.

In this work, antibacterial activity of finger citron essential oil (FCEO, Citrus medica L. var. sarcodactylis) and its mechanism against food-borne bacteria were evaluated. A total of 28 components in the oil were identified by gas chromatography-mass spectrometry, in which limonene (45.36%), γ-terpinene (21.23%), and dodecanoic acid (7.52%) were three main components. For in vitro antibacterial tests, FCEO exhibited moderately antibacterial activity against common food-borne bacteria: Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Micrococcus luteus. It showed a better bactericidal effect on Gram-positive bacteria than Gram-negative. Mechanisms of the antibacterial action were investigated by observing changes of bacteria morphology according to scanning electron microscopy, time-kill analysis, and permeability of cell and membrane integrity. Morphology of tested bacteria was changed and damaged more seriously with increased concentration and exposure time of FCEO. FCEO showed a significant reduction effect on the growth rate of surviving bacteria and lead to lysis of the cell wall, intracellular ingredient leakage, and consequently, cell death. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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11 pages, 1206 KiB

Open AccessArticle

Correlation between Chemical Composition and Antifungal Activity of Clausena lansium Essential Oil against Candida spp.

by Xiaowen He, Lantong Zhang, Jinping Chen, Jinlei Sui, Guohui Yi, Jinyan Wu and Yinzheng Ma

Molecules 2019, 24(7), 1394; https://doi.org/10.3390/molecules24071394 - 9 Apr 2019

Cited by 26 | Viewed by 3737

Abstract

Essential oils (EOs) have been shown to have a diversity of beneficial human health effects. Clausena is a large and highly diverse genus of plants with medicinal and cosmetic significance. The aim of this study was to analyze the composition of Clausena lansium [...] Read more.

Essential oils (EOs) have been shown to have a diversity of beneficial human health effects. Clausena is a large and highly diverse genus of plants with medicinal and cosmetic significance. The aim of this study was to analyze the composition of Clausena lansium EOs and to investigate their potential antifungal effects. The chemical compositions of Clausena lansium EOs obtained by hydrodistillation were analyzed by gas chromatography-mass spectrometry (GC-MS). A total of 101 compounds were identified among the diverse extracts of C. lansium. EOs of leaves and pericarps from different cultivars (Hainan local wampee and chicken heart wampee) collected in Hainan (China) were classified into four clusters based on their compositions. These clusters showed different antifungal activities against five Candida species (C. albicans, C. tropicalis, C. glabrata, C. krusei and C. parapsilosis) using the disc diffusion method. Clausena lansium EOs of pericarps displayed noteworthy antifungal activitives against all the tested Candida strains with inhibition zone diameters in the range of 11.1–23.1 mm. EOs of leaves showed relatively low antifungal activities with inhibition zone diameters in the range of 6.5–22.2 mm. The rank order of antifungal activities among the four EO clusters was as follows: Cluster IV> Cluster III > Cluster I ≥ Cluster II. These results represent the first report about the correlation between chemical composition of C. lansium EOs and antifungal activity. Higher contents of β-phellandrene, β-sesquiphellandrene and β-bisabolene in EOs of pericarps were likely responsible for the high antifungal activity of Cluster IV EOs. Taken together, our results demonstrate the chemical diversity of Clausena lansium EOs and their potential as novel antifungal agents for candidiasis caused by Candida spp. Furthermore, the obtained results showing a wide spectrum of antifungal activities provide scientific evidence for the traditional use of these plants. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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15 pages, 5427 KiB

Open AccessArticle

Inhibition of Satellite RNA Associated Cucumber Mosaic Virus Infection by Essential Oil of Micromeria croatica (Pers.) Schott

by Elma Vuko, Gordana Rusak, Valerija Dunkić, Dario Kremer, Ivan Kosalec, Biljana Rađa and Nada Bezić

Molecules 2019, 24(7), 1342; https://doi.org/10.3390/molecules24071342 - 5 Apr 2019

Cited by 21 | Viewed by 3475

Abstract

The present results dealing with the antiphytoviral activity of essential oil indicate that these plant metabolites can trigger a response to viral infection. The essential oil from Micromeria croatica and the main oil components β-caryophyllene and caryophyllene oxide were tested for antiphytoviral activity [...] Read more.

The present results dealing with the antiphytoviral activity of essential oil indicate that these plant metabolites can trigger a response to viral infection. The essential oil from Micromeria croatica and the main oil components β-caryophyllene and caryophyllene oxide were tested for antiphytoviral activity on plants infected with satellite RNA associated cucumber mosaic virus. Simultaneous inoculation of virus with essential oil or with the dominant components of oil, and the treatment of plants prior to virus inoculation, resulted in a reduction of virus infection in the local and systemic host plants. Treatment with essential oil changed the level of alternative oxidase gene expression in infected Arabidopsis plants indicating a connection between the essential oil treatment, aox gene expression and the development of viral infection. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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8 pages, 227 KiB

Open AccessArticle

In Vitro Activity of Essential Oils against Saprolegnia parasitica

by Simona Nardoni, Basma Najar, Baldassare Fronte, Luisa Pistelli and Francesca Mancianti

Molecules 2019, 24(7), 1270; https://doi.org/10.3390/molecules24071270 - 1 Apr 2019

Cited by 26 | Viewed by 3875

Abstract

Saprolegnia spp. water molds severely impact fish health in aquaculture, fish farms and hobby fish tanks colonizing mature and immature stages of fishes, as well as eggs. Considering that there are no drugs licensed for treating and/or control the organism, efficient and environmental [...] Read more.

Saprolegnia spp. water molds severely impact fish health in aquaculture, fish farms and hobby fish tanks colonizing mature and immature stages of fishes, as well as eggs. Considering that there are no drugs licensed for treating and/or control the organism, efficient and environmental low-impact methods to control these oomycetes in aquaculture are needed. The aim of the present report was to evaluate the in vitro sensitivity of Saprolegnia parasitica to essential oils (EOs) from Citrus aurantium L., Citrus bergamia Risso et Poiteau, Citrus limon Burm. f., Citrus paradisi Macfad, Citrus sinensis Osbeck, Cinnamomum zeylanicum Blume, Cymbopogon flexuosum (Nees ex Steud.) Watson, Foeniculum vulgare Mill., Illicium verum Hook.f., Litsea cubeba (Lour.) Pers., Origanum majorana L., Origanum vulgare L., Pelargonium graveolens L’Hér., Syzygium aromaticum Merr. & L.M.Perry, and Thymus vulgaris L., by microdilution test. The most effective EOs assayed were T. vulgaris and O. vulgare, followed by C. flexuosum, L. cubeba and C. bergamia. These EOs could be of interest for controlling Saprolegnia infections. Nevertheless, further safety studies are necessary to evaluate if these products could be dispersed in tank waters, or if their use should be limited to aquaculture supplies. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

12 pages, 881 KiB

Open AccessArticle

Antimicrobial Activity and Chemical Composition of Essential Oil Extracted from Solidago canadensis L. Growing Wild in Slovakia

by Hazem S. Elshafie, Daniela Gruľová, Beáta Baranová, Lucia Caputo, Laura De Martino, Vincent Sedlák, Ippolito Camele and Vincenzo De Feo

Molecules 2019, 24(7), 1206; https://doi.org/10.3390/molecules24071206 - 27 Mar 2019

Cited by 68 | Viewed by 6160

Abstract

Plant essential oils (EOs) are one of the most relevant natural products due to their biological, medicinal, and nutritional properties. The promising biological effects of many plants EOs encourage researchers to study their biochemical properties to be used as possible natural alternatives for [...] Read more.

Plant essential oils (EOs) are one of the most relevant natural products due to their biological, medicinal, and nutritional properties. The promising biological effects of many plants EOs encourage researchers to study their biochemical properties to be used as possible natural alternatives for commercial pesticides and not only as herbal medicines. The current research has been conducted to study the microbicide effect of Solidago canadensis L. EO to control some common plant diseases caused by several postharvest phytopathogenic fungi (Monilinia fructicola, Botrytis cinerea, Aspergillus niger, and Penicillium expansum) in comparison with Azoxystrobin as a large spectrum fungicide. The antibacterial activity has been carried out against some phytopathogenic bacteria (Bacillus megaterium and Clavibacter michiganensis (G+ve) and Xanthomonas campestris, Pseudomonas fluorescens, and Pseudomonas syringae pv. phaseolicola (G−ve)) compared to the synthetic antibiotic Tetracycline. Minimum inhibitory concentration was carried out to determine the lowest effective EO dose using a 96-well microplate. The cell membrane permeability was also evaluated by measuring the electric conductivity (EC) to examine the possible mechanisms of action of S. canadensis EO. Chemical characterization of EO has been carried out using gas chromatography and mass spectrometry (GC-MS). Thirty-two identified components in S. canadensis EO presented 97.7% of total compounds in EO. The principal compounds were identified as germacrene D (34.9%), limonene (12.5%), α-pinene (11.6%), β-elemene (7.1%), and bornyl acetate (6.3%). In addition, S. canadensis EO demonstrated promising in vitro antimicrobial activities against the majority of tested phytopathogens at all tested concentrations. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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13 pages, 1198 KiB

Open AccessArticle

Evaluation of the Anti-Trypanosomal Activity of Vietnamese Essential Oils, with Emphasis on Curcuma longa L. and Its Components

by Thanh Binh Le, Claire Beaufay, Duc Trong Nghiem, Tuan Anh Pham, Marie-Paule Mingeot-Leclercq and Joëlle Quetin-Leclercq

Molecules 2019, 24(6), 1158; https://doi.org/10.3390/molecules24061158 - 23 Mar 2019

Cited by 24 | Viewed by 5153

Abstract

Human African trypanosomiasis (HAT), known as sleeping sickness and caused by Trypanosoma brucei, is threatening low-income populations in sub-Saharan African countries with 61 million people at risk of infection. In order to discover new natural products against HAT, thirty-seven Vietnamese essential oils [...] Read more.

Human African trypanosomiasis (HAT), known as sleeping sickness and caused by Trypanosoma brucei, is threatening low-income populations in sub-Saharan African countries with 61 million people at risk of infection. In order to discover new natural products against HAT, thirty-seven Vietnamese essential oils (EOs) were screened for their activity in vitro on Trypanosoma brucei brucei (Tbb) and cytotoxicity on mammalian cells (WI38, J774). Based on the selectivity indices (SIs), the more active and selective EOs were analyzed by gas chromatography. The anti-trypanosomal activity and cytotoxicity of some major compounds (isolated or commercial) were also determined. Our results showed for the first time the selective anti-trypanosomal effect of four EOs, extracted from three Zingiberaceae species (Curcuma longa, Curcuma zedoaria, and Zingiber officinale) and one Lauraceae species (Litsea cubeba) with IC₅₀ values of 3.17 ± 0.72, 2.51 ± 1.08, 3.10 ± 0.08, and 2.67 ± 1.12 nL/mL respectively and SI > 10. Identified compounds accounted for more than 85% for each of them. Among the five major components of Curcuma longa EO, curlone is the most promising anti-trypanosomal candidate with an IC₅₀ of 1.38 ± 0.45 µg/mL and SIs of 31.7 and 18.2 compared to WI38 and J774 respectively. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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15 pages, 3433 KiB

Open AccessArticle

Tea Seed Oil Prevents Obesity, Reduces Physical Fatigue, and Improves Exercise Performance in High-Fat-Diet-Induced Obese Ovariectomized Mice

by Yu-Tang Tung, Yi-Ju Hsu, Yi-Wen Chien, Chi-Chang Huang, Wen-Ching Huang and Wan-Chun Chiu

Molecules 2019, 24(5), 980; https://doi.org/10.3390/molecules24050980 - 11 Mar 2019

Cited by 22 | Viewed by 5430

Abstract

Menopause is associated with changes in body composition (a decline in lean body mass and an increase in total fat mass), leading to an increased risk of metabolic syndrome, nonalcoholic fatty liver disease, and heart disease. A healthy diet to control body weight [...] Read more.

Menopause is associated with changes in body composition (a decline in lean body mass and an increase in total fat mass), leading to an increased risk of metabolic syndrome, nonalcoholic fatty liver disease, and heart disease. A healthy diet to control body weight is an effective strategy for preventing and treating menopause-related metabolic syndromes. In the present study, we investigated the effect of long-term feeding of edible oils (soybean oil (SO), tea seed oil (TO), and lard oil (LO)) on female ovariectomized (OVX) mice. SO, TO, and LO comprise mainly polyunsaturated fatty acids (PUFA), monounsaturated fatty acids (MUFA), and saturated fatty acids (SFA), respectively. However, there have been quite limited studies to investigate the effects of different fatty acids (PUFA, MUFA, and SFA) on physiological adaption and metabolic homeostasis in a menopausal population. In this study, 7-week-old female Institute of Cancer Research (ICR) mice underwent either bilateral laparotomy (sham group, n = 8) or bilateral oophorectomy (OVX groups, n = 24). The OVX mice given a high-fat diet (HFD) were randomly divided into three groups: OVX+SO, OVX+TO, and OVX+LO. An HFD rich in SO, TO, or LO was given to the OVX mice for 12 weeks. Our findings revealed that the body weight and relative tissues of UFP (uterus fatty peripheral) and total fat (TF) were significantly decreased in the OVX+TO group compared with those in the OVX+SO and OVX+LO groups. However, no significant difference in body weight or in the relative tissues of UFP and TF was noted among the OVX+SO and OVX+LO groups. Furthermore, mice given an HFD rich in TO exhibited significantly decreased accumulation of liver lipid droplets and adipocyte sizes of UFP and brown adipose tissue (BAT) compared with those given an HFD rich in SO or LO. Moreover, replacing SO or LO with TO significantly increased oral glucose tolerance. Additionally, TO improved endurance performance and exhibited antifatigue activity by lowering ammonia, blood urea nitrogen, and creatine kinase levels. Thus, tea seed oil (TO) rich in MUFA could prevent obesity, reduce physical fatigue, and improve exercise performance compared with either SO (PUFA)- or LO(SFA)-rich diets in this HFD-induced obese OVX mice model. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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10 pages, 527 KiB

Open AccessArticle

Essential Oil Composition and Biological Activity of “Pompia”, a Sardinian Citrus Ecotype

by Guido Flamini, Laura Pistelli, Simona Nardoni, Valentina Virginia Ebani, Angela Zinnai, Francesca Mancianti, Roberta Ascrizzi and Luisa Pistelli

Molecules 2019, 24(5), 908; https://doi.org/10.3390/molecules24050908 - 5 Mar 2019

Cited by 20 | Viewed by 3809

Abstract

Pompia is a Sardinian citrus ecotype whose botanical classification is still being debated. In the present study, the composition of Pompia peel essential oil (EO) is reported for the first time, along with that of the leaf EO, as a phytochemical contribution to [...] Read more.

Pompia is a Sardinian citrus ecotype whose botanical classification is still being debated. In the present study, the composition of Pompia peel essential oil (EO) is reported for the first time, along with that of the leaf EO, as a phytochemical contribution to the classification of this ecotype. The peel EO was tested for its antioxidant ability (with both the 2,2-diphenyl-1-picarylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) assays). Moreover, its antimicrobial activities were tested for the first time on dermatophytes (Microsporum canis, Microsporum gypseum, and Trichophyton mentagrophytes), on potentially toxigenic fungi (Fusarium solani, Aspergillus flavus, and Aspergillus niger) as well on bacteria (Escherichia coli, Staphylococcus aureus, and Staphylococcus pseudointermedius). The dominant abundance of limonene in the peel EO seems to distinguish Pompia from the Citrus spp. to which it had previously been associated. It lacks γ-terpinene, relevant in Citrus medica EO. Its relative content of α- and β-pinene is lower than 0.5%, in contrast to Citrus limon peel EO. Pompia peel and leaf EOs did not show significant amounts of linalool and linalyl acetate, which are typically found in Citrus aurantium. Pompia peel EO antioxidant activity was weak, possibly because of its lack of γ-terpinene. Moreover, it did not exert any antimicrobial effects either towards the tested bacteria strains, or to dermatophytes and environmental fungi. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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26 pages, 4331 KiB

Open AccessFeature PaperArticle

Machine Learning Analyses on Data including Essential Oil Chemical Composition and In Vitro Experimental Antibiofilm Activities against Staphylococcus Species

by Alexandros Patsilinakos, Marco Artini, Rosanna Papa, Manuela Sabatino, Mijat Božović, Stefania Garzoli, Gianluca Vrenna, Raissa Buzzi, Stefano Manfredini, Laura Selan and Rino Ragno

Molecules 2019, 24(5), 890; https://doi.org/10.3390/molecules24050890 - 3 Mar 2019

Cited by 41 | Viewed by 6398

Abstract

Biofilm resistance to antimicrobials is a complex phenomenon, driven not only by genetic mutation induced resistance, but also by means of increased microbial cell density that supports horizontal gene transfer across cells. The prevention of biofilm formation and the treatment of existing biofilms [...] Read more.

Biofilm resistance to antimicrobials is a complex phenomenon, driven not only by genetic mutation induced resistance, but also by means of increased microbial cell density that supports horizontal gene transfer across cells. The prevention of biofilm formation and the treatment of existing biofilms is currently a difficult challenge; therefore, the discovery of new multi-targeted or combinatorial therapies is growing. The development of anti-biofilm agents is considered of major interest and represents a key strategy as non-biocidal molecules are highly valuable to avoid the rapid appearance of escape mutants. Among bacteria, staphylococci are predominant causes of biofilm-associated infections. Staphylococci, especially Staphylococcus aureus (S. aureus) is an extraordinarily versatile pathogen that can survive in hostile environmental conditions, colonize mucous membranes and skin, and can cause severe, non-purulent, toxin-mediated diseases or invasive pyogenic infections in humans. Staphylococcus epidermidis (S. epidermidis) has also emerged as an important opportunistic pathogen in infections associated with medical devices (such as urinary and intravascular catheters, orthopaedic implants, etc.), causing approximately from 30% to 43% of joint prosthesis infections. The scientific community is continuously looking for new agents endowed of anti-biofilm capabilities to fight S. aureus and S epidermidis infections. Interestingly, several reports indicated in vitro efficacy of non-biocidal essential oils (EOs) as promising treatment to reduce bacterial biofilm production and prevent the inducing of drug resistance. In this report were analyzed 89 EOs with the objective of investigating their ability to modulate bacterial biofilm production of different S. aureus and S. epidermidis strains. Results showed the assayed EOs to modulated the biofilm production with unpredictable results for each strain. In particular, many EOs acted mainly as biofilm inhibitors in the case of S. epidermidis strains, while for S. aureus strains, EOs induced either no effect or stimulate biofilm production. In order to elucidate the obtained experimental results, machine learning (ML) algorithms were applied to the EOs’ chemical compositions and the determined associated anti-biofilm potencies. Statistically robust ML models were developed, and their analysis in term of feature importance and partial dependence plots led to indicating those chemical components mainly responsible for biofilm production, inhibition or stimulation for each studied strain, respectively. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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12 pages, 1192 KiB

Open AccessArticle

Volatiles Profiling, Allelopathic Activity, and Antioxidant Potentiality of Xanthium Strumarium Leaves Essential Oil from Egypt: Evidence from Chemometrics Analysis

by Ahmed Abd El-Gawad, Abdelsamed Elshamy, Abd El-Nasser El Gendy, Ahmed Gaara and Abdulaziz Assaeed

Molecules 2019, 24(3), 584; https://doi.org/10.3390/molecules24030584 - 7 Feb 2019

Cited by 61 | Viewed by 6427

Abstract

The essential oil (EO) of Xanthium strumarium L. leaves (family: Asteraceae) was extracted by hydrodistillation, and then analyzed by gas chromatography-mass spectrometry (GC-MS). Forty-three essential compounds were identified. The sesquiterpenoids represented the major constituents (72.4%), including oxygenated (61.78%) and non-oxygenated (10.62%) sesquiterpenes, followed [...] Read more.

The essential oil (EO) of Xanthium strumarium L. leaves (family: Asteraceae) was extracted by hydrodistillation, and then analyzed by gas chromatography-mass spectrometry (GC-MS). Forty-three essential compounds were identified. The sesquiterpenoids represented the major constituents (72.4%), including oxygenated (61.78%) and non-oxygenated (10.62%) sesquiterpenes, followed by monoterpenes (25.19%). The diterpenoids and oxygenated hydrocarbons were determined as minor compounds. The main constituents of the EO were 1,5-dimethyltetralin (14.27%), eudesmol (10.60%), l-borneol (6.59%), ledene alcohol (6.46%), (-)-caryophyllene oxide (5.36%), isolongifolene, 7,8-dehydro-8a-hydroxy (5.06%), L-bornyl acetate (3.77%), and aristolene epoxide (3.58%). A comparative analysis was stated here between the EO of Egyptian X. strumarium and those previously reported from Pakistan, Iran, and Brazil based on chemometic tools such as principal components analysis (PCA) and agglomerative hierarchical clustering (AHC). The EO of X. strumarium showed weak 1, 1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging activity with IC₅₀ 321.93 µL/L⁻¹, which was comparable to ascorbic acid as a reference. However, the EO exhibited significant allelopathic potential regarding the germination and growth of the noxious weed Bidens pilosa in a concentration-dependent manner. Therefore, further study is recommended to characterize the EO from X. strumarium as an eco-friendly green bioherbicide against weeds, as well as determine their mode of actions. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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12 pages, 2055 KiB

Open AccessArticle

Extraction of ‘Gannanzao’ Orange Peel Essential Oil by Response Surface Methodology and its Effect on Cancer Cell Proliferation and Migration

by Ke Liu, Weihui Deng, Wei Hu, Shan Cao, Balian Zhong and Jiong Chun

Molecules 2019, 24(3), 499; https://doi.org/10.3390/molecules24030499 - 30 Jan 2019

Cited by 28 | Viewed by 4850

Abstract

The essential oil of ‘Gannanzao’ orange peel was extracted by hydrodistillation, and the extraction conditions were optimized by Box–Behnken response surface methodology. The components of essential oil were analyzed by GC-MS. Thirty-nine different components were detected, accounting for 99.59% of the total oil. [...] Read more.

The essential oil of ‘Gannanzao’ orange peel was extracted by hydrodistillation, and the extraction conditions were optimized by Box–Behnken response surface methodology. The components of essential oil were analyzed by GC-MS. Thirty-nine different components were detected, accounting for 99.59% of the total oil. Limonene (88.07%) was the prominent component. The optimal extraction conditions were as follows: liquid material ratio of 8.4:1 (mL/g), sodium chloride concentration of 5.3%, and distillation time of 3.5 h. The Cell Counting Kit-8 assay showed that ‘Gannanzao’ orange peel essential oil had good dose-dependent inhibition effect on the proliferation of HepG2 hepatoma cells and HCT116 colorectal cancer cells. When the concentration of the essential oil was 0.6 μL/mL or higher, the viability rate of both cancer cells became lower than 13.0%. The transwell assay indicated the essential oil can inhibit migration of both cancer cells at the concentration of 0.3 μL/mL. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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9 pages, 248 KiB

Open AccessArticle

Phytotoxic Effect of Invasive Heracleum mantegazzianum Essential Oil on Dicot and Monocot Species

by Martina Matoušková, Jana Jurová, Daniela Gruľová, Anna Wajs-Bonikowska, Marek Renčo, Vincent Sedlák, Janka Poráčová, Zuzana Gogaľová and Danuta Kalemba

Molecules 2019, 24(3), 425; https://doi.org/10.3390/molecules24030425 - 24 Jan 2019

Cited by 16 | Viewed by 4195

Abstract

Spreading of the plant species in new areas is supported by the hypothesis in which chemicals produced by alien species are allopathic to native plants. A novel weapon hypothesis was tested by using essential oil of dangerous alien species Heracleum mantegazzianum in laboratory [...] Read more.

Spreading of the plant species in new areas is supported by the hypothesis in which chemicals produced by alien species are allopathic to native plants. A novel weapon hypothesis was tested by using essential oil of dangerous alien species Heracleum mantegazzianum in laboratory conditions. Aboveground plant material was collected in south-east part of Slovakia, dried and hydrodistilled for essential oil isolation. Dominant compounds as octyl acetate (62.6%), hexyl 2-metylbutyrate (10.7%), hexyl isobutyrate (7.5%) and hexyl butyrate (6.5%) were identified by GC-MS. Potential phytotoxic activity was tested on three dicot plant species garden cress (Lepidium sativum L.), radish (Raphanus sativus L.) and lettuce (Lactuca sativa L.) and on one monocot plant species wheat Triticum aestivum L. Germination of the seeds of model plant species after influencing by different doses of essential oil of H. mantegazzianum as well as the roots length was evaluated. Lepidium sativum L. and Raphanus sativus L. were generally not sensitive to applied doses of essential oil although a little stimulation effect at some concentrations prevailed over inhibition effect. Similarly, in monocot species Triticum aestivum L., stimulation was visible in both root length and root number at two or one highest doses, respectively. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

8 pages, 209 KiB

Open AccessCommunication

Chemical Composition and Antimicrobial Activity of Essential Oil from Phytolacca dodecandra Collected in Ethiopia

by Wondwosen Abebe Matebie, Wanchang Zhang and Guangbo Xie

Molecules 2019, 24(2), 342; https://doi.org/10.3390/molecules24020342 - 18 Jan 2019

Cited by 21 | Viewed by 4631

Abstract

The essential oil from Phytolacca dodecandra, a traditional herb of Ethiopia, has been studied, including the chemical composition and antimicrobial activity. The difference between four P. dodecandra samples (P-1–P-4), which differed in gender or location, has also been analyzed. The essential oils [...] Read more.

The essential oil from Phytolacca dodecandra, a traditional herb of Ethiopia, has been studied, including the chemical composition and antimicrobial activity. The difference between four P. dodecandra samples (P-1–P-4), which differed in gender or location, has also been analyzed. The essential oils were obtained by steam distillation, while the aromas were extracted by head space solid-phase microextraction (HS-SPME) and both were analyzed by gas chromatography- mass spectrometry (GC-MS). The oils’ antimicrobial activities were evaluated by the microdilution method against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Candida albicans. Ninety one components, representing 88.37 to 94.01% of the aromas, were identified. The compositions of the aromas of four samples are mainly dominated by aldehydes and ketones: 2-nonanone (1.80–30.80%), benzaldehyde (4.99–25.99%), and sulcatone (2.34–5.87%). Sixty components representing 64.61 to 69.64% of the oils were identified, and phytone (3.04–21.23%), phytol (4.11–26.29%) and palmitic acid (1.49–23.87%) are the major compounds. No obvious antimicrobial activity was observed for all the four essential oils. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

14 pages, 4635 KiB

Open AccessArticle

Comparison of the Fungistatic Activity of Selected Essential Oils Relative to Fusarium graminearum Isolates

by Teresa Krzyśko-Łupicka, Weronika Walkowiak and Marietta Białoń

Molecules 2019, 24(2), 311; https://doi.org/10.3390/molecules24020311 - 16 Jan 2019

Cited by 26 | Viewed by 3704

Abstract

The aim of the study was to determine the chemical composition of lemon, rosewood, geranium and rosemary oils, and compare their effect on the sensitivity of Fusarium graminearum ZALF 24 and Fusarium graminearum ZALF 339 isolated from infected cereals. The tested oils were [...] Read more.

The aim of the study was to determine the chemical composition of lemon, rosewood, geranium and rosemary oils, and compare their effect on the sensitivity of Fusarium graminearum ZALF 24 and Fusarium graminearum ZALF 339 isolated from infected cereals. The tested oils were added to Potato Dextrose Agar (PDA) medium at concentrations of 0.125%, 0.25%, 0.5%, 1.0% and 2.0%. The activity of the oils on inhibition of the linear growth of mycelium was evaluated by measuring the growth of fungal colonies (growth index), while the fungistatic activity was evaluated on the basis of the percentage growth inhibition of a fungal colony and calculated according to Abbott’s formula. The sensitivity of the test strains was variable and depended on the type and concentration of the tested oils. Geranium and rosewood oils in all of the concentrations completely inhibited the growth of the used isolates. In contrast, lemon oil relative to F. graminearum ZALF 339 showed the highest activity at a concentration of 1.0% and rosemary oil, 0.5%. The highest activity against F. graminearum ZALF 24 was shown by the oils of rosemary and lemon at concentrations from 1.0% to 2.0%. The susceptibility of Fusarium graminearum isolates was differentiated and depended on the type and concentration of tested oils. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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15 pages, 1139 KiB

Open AccessArticle

Biological Activities and Chemical Composition of Santolina africana Jord. et Fourr. Aerial Part Essential Oil from Algeria: Occurrence of Polyacetylene Derivatives

by Charaf Eddine Watheq Malti, Clémentine Baccati, Magali Mariani, Faiçal Hassani, Brahim Babali, Fewzia Atik-Bekkara, Mathieu Paoli, Jacques Maury, Félix Tomi and Chahrazed Bekhechi

Molecules 2019, 24(1), 204; https://doi.org/10.3390/molecules24010204 - 8 Jan 2019

Cited by 10 | Viewed by 5339

Abstract

The chemical composition of 18 oil samples of Santolina africana isolated from aerial parts at full flowering, collected in three locations in eastern Algeria was determined by GC(RI), GC/MS and ¹³C-NMR analysis. The major components were: germacrene D, myrcene, spathulenol, α-bisabolol, β-pinene, [...] Read more.

The chemical composition of 18 oil samples of Santolina africana isolated from aerial parts at full flowering, collected in three locations in eastern Algeria was determined by GC(RI), GC/MS and ¹³C-NMR analysis. The major components were: germacrene D, myrcene, spathulenol, α-bisabolol, β-pinene, 1,8-cineole, cis-chrysanthenol, capillene, santolina alcohol, camphor, terpinen-4-ol and lyratol. The chemical composition appeared homogeneous and characterized by the occurrence of four derivatives which exhibited a conjugated alkene dialkyne moiety. They were identified for the first time in an essential oil from S. africana. The collective oil sample exhibited moderate antimicrobial and antioxidant activities whereas the anti-inflammatory activity presented a real potential. IC₅₀ value of Santolina africana essential oil (0.065 ± 0.004 mg/mL) is 5-fold higher than IC₅₀ value of NDGA used as positive control. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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16 pages, 3542 KiB

Open AccessArticle

Sub-Inhibitory Doses of Individual Constituents of Essential Oils Can Select for Staphylococcus aureus Resistant Mutants

by Daniel Berdejo, Beatriz Chueca, Elisa Pagán, Adriana Renzoni, William L. Kelley, Rafael Pagán and Diego Garcia-Gonzalo

Molecules 2019, 24(1), 170; https://doi.org/10.3390/molecules24010170 - 4 Jan 2019

Cited by 18 | Viewed by 4095

Abstract

Increased bacterial resistance to food preservation technologies represents a risk for food safety and shelf-life. The use of natural antimicrobials, such as essential oils (EOs) and their individual constituents (ICs), has been proposed to avoid the generation of antimicrobial resistance. However, prolonged application [...] Read more.

Increased bacterial resistance to food preservation technologies represents a risk for food safety and shelf-life. The use of natural antimicrobials, such as essential oils (EOs) and their individual constituents (ICs), has been proposed to avoid the generation of antimicrobial resistance. However, prolonged application of ICs might conceivably lead to the emergence of resistant strains. Hence, this study was aimed toward applying sub-inhibitory doses of the ICs carvacrol, citral, and (+)-limonene oxide to Staphylococcus aureus USA300, in order to evaluate the emergence of resistant strains and to identify the genetic modifications responsible for their increased resistance. Three stable-resistant strains, CAR (from cultures with carvacrol), CIT (from cultures with citral), and OXLIM (from cultures with (+)-limonene oxide) were isolated, showing an increased resistance against the ICs and a higher tolerance to lethal treatments by ICs or heat. Whole-genome sequencing revealed in CAR a large deletion in a region that contained genes encoding transcriptional regulators and metabolic enzymes. CIT showed a single missense mutation in aroC (N187K), which encodes for chorismate synthase; and in OXLIM a missense mutation was detected in rpoB (A862V), which encodes for RNA polymerase subunit beta. This study provides a first detailed insight into the mechanisms of action and S. aureus resistance arising from exposure to carvacrol, citral, and (+)-limonene oxide. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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16 pages, 2063 KiB

Open AccessArticle

Wound Healing Effect of Essential Oil Extracted from Eugenia dysenterica DC (Myrtaceae) Leaves

by Sandra Márcia Mazutti da Silva, Claudio Rodrigues Rezende Costa, Guilherme Martins Gelfuso, Eliete Neves Silva Guerra, Yanna Karla De Medeiros Nóbrega, Sueli Maria Gomes, Aline Pic-Taylor, Yris Maria Fonseca-Bazzo, Damaris Silveira and Pérola de Oliveira Magalhães

Molecules 2019, 24(1), 2; https://doi.org/10.3390/molecules24010002 - 20 Dec 2018

Cited by 48 | Viewed by 9797

Abstract

The use of natural oils in topical pharmaceutical preparations has usually presented safe agents for the improvement of human health. Based on research into the immense potential of wound management and healing, we aimed to validate the use of topical natural products by [...] Read more.

The use of natural oils in topical pharmaceutical preparations has usually presented safe agents for the improvement of human health. Based on research into the immense potential of wound management and healing, we aimed to validate the use of topical natural products by studying the ability of the essential oil of Eugenia dysenterica DC leaves (oEd) to stimulate in vitro skin cell migration. Skin cytotoxicity was evaluated using a fibroblast cell line (L929) by MTT assay. The oil chemical profile was investigated by GC-MS. Moreover, the inhibition of lipopolysaccharide (LPS) induced nitric oxide (NO) production in the macrophage cell line (RAW 264.7) tested. The Chick Chorioallantoic Membrane (CAM) assay was used to evaluate the angiogenic activity and irritating potential of the oil. The oEd induces skin cell migration in a scratch assay at a concentration of 542.2 µg/mL. α-humulene and β-caryophyllene, the major compounds of this oil, as determined by GC-MS, may partly explain the migration effect. The inhibition of nitric oxide by oEd and α-humulene suggested an anti-inflammatory effect. The CAM assay showed that treatment with oEd ≤ 292 µg/mL did not cause skin injury, and that it can promote angiogenesis in vivo. Hence, these results indicate the feasibility of the essential oil of Eugenia dysenterica DC leaves to developed dermatological products capable of helping the body to repair damaged tissue. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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12 pages, 901 KiB

Open AccessArticle

Antitumor Effect of the Essential Oil from the Leaves of Croton matourensis Aubl. (Euphorbiaceae)

by Emilly J. S. P. de Lima, Rafaela G. Alves, Gigliola M. A. D´Elia, Talita A. da Anunciação, Valdenizia R. Silva, Luciano de S. Santos, Milena B. P. Soares, Nállarett M. D. Cardozo, Emmanoel V. Costa, Felipe M. A. da Silva, Hector H. F. Koolen and Daniel P. Bezerra

Molecules 2018, 23(11), 2974; https://doi.org/10.3390/molecules23112974 - 14 Nov 2018

Cited by 32 | Viewed by 3957

Abstract

Croton matourensis Aubl. (synonym Croton lanjouwensis Jabl.), popularly known as “orelha de burro”, “maravuvuia”, and/or “sangrad’água”, is a medicinal plant used in Brazilian folk medicine as a depurative and in the treatment of infections, fractures, and colds. In this work, we investigated the [...] Read more.

Croton matourensis Aubl. (synonym Croton lanjouwensis Jabl.), popularly known as “orelha de burro”, “maravuvuia”, and/or “sangrad’água”, is a medicinal plant used in Brazilian folk medicine as a depurative and in the treatment of infections, fractures, and colds. In this work, we investigated the chemical composition and in vitro cytotoxic and in vivo antitumor effects of the essential oil (EO) from the leaves of C. matourensis collected from the Amazon rainforest. The EO was obtained by hydrodistillation using a Clevenger-type apparatus and characterized qualitatively and quantitatively by gas chromatography coupled to mass spectrometry (GC–MS) and gas chromatography with flame ionization detection (GC–FID), respectively. In vitro cytotoxicity of the EO was assessed in cancer cell lines (MCF-7, HCT116, HepG2, and HL-60) and the non-cancer cell line (MRC-5) using the Alamar blue assay. Furthermore, annexin V-FITC/PI staining and the cell cycle distribution were evaluated with EO-treated HepG2 cells by flow cytometry. In vivo efficacy of the EO (40 and 80 mg/kg/day) was demonstrated in C.B-17 severe combined immunodeficient (SCID) mice with HepG2 cell xenografts. The EO included β-caryophyllene, thunbergol, cembrene, p-cymene, and β-elemene as major constituents. The EO exhibited promising cytotoxicity and was able to cause phosphatidylserine externalization and DNA fragmentation without loss of the cell membrane integrity in HepG2 cells. In vivo tumor mass inhibition rates of the EO were 34.6% to 55.9%. Altogether, these data indicate the anticancer potential effect of C. matourensis. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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Review

Jump to: Editorial, Research

21 pages, 384 KiB

Open AccessReview

Essential Oils as Antimicrobial Agents—Myth or Real Alternative?

by Katarzyna Wińska, Wanda Mączka, Jacek Łyczko, Małgorzata Grabarczyk, Anna Czubaszek and Antoni Szumny

Molecules 2019, 24(11), 2130; https://doi.org/10.3390/molecules24112130 - 5 Jun 2019

Cited by 362 | Viewed by 40622

Abstract

Herbs and the essential oils derived from them have been used from the beginning of human history for different purposes. Their beneficial properties have been applied to mask unpleasant odors, attract the attention of other people, add flavor and aroma properties to prepared [...] Read more.

Herbs and the essential oils derived from them have been used from the beginning of human history for different purposes. Their beneficial properties have been applied to mask unpleasant odors, attract the attention of other people, add flavor and aroma properties to prepared dishes, perfumes, and cosmetics, etc. Herbs and essential oils (EOs) have also been used in medicine because of their biological properties, such as larvicidal action, analgesic and anti-inflammatory properties, antioxidant, fungicide, and antitumor activities, and many more. Many EOs exhibit antimicrobial properties, which is extremely important in fields of science and industry, such as medicine, agriculture, or cosmetology. Among the 250 EOs which are commercially available, about a dozen possess high antimicrobial potential. According to available papers and patents, EOs seem to be a potential alternative to synthetic compounds, especially because of the resistance that has been increasingly developed by pathogenic microorganisms. In this review we summarize the latest research studies about the most-active EOs that are known and used because of their antimicrobial properties. Finally, it is noteworthy that the antimicrobial activities of EOs are not preeminent for all strains. Further investigations should, thus, focus on targeting EOs and microorganisms. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

29 pages, 948 KiB

Open AccessReview

Antispasmodic Effect of Essential Oils and Their Constituents: A Review

by Simona Codruta Heghes, Oliviu Vostinaru, Lucia Maria Rus, Cristina Mogosan, Cristina Adela Iuga and Lorena Filip

Molecules 2019, 24(9), 1675; https://doi.org/10.3390/molecules24091675 - 29 Apr 2019

Cited by 63 | Viewed by 12501

Abstract

The antispasmodic effect of drugs is used for the symptomatic treatment of cramping and discomfort affecting smooth muscles from the gastrointestinal, billiary or genitourinary tract in a variety of clinical situations.The existing synthetic antispasmodic drugs may cause a series of unpleasant side effects, [...] Read more.

The antispasmodic effect of drugs is used for the symptomatic treatment of cramping and discomfort affecting smooth muscles from the gastrointestinal, billiary or genitourinary tract in a variety of clinical situations.The existing synthetic antispasmodic drugs may cause a series of unpleasant side effects, and therefore the discovery of new molecules of natural origin is an important goal for the pharmaceutical industry. This review describes a series of recent studies investigating the antispasmodic effect of essential oils from 39 plant species belonging to 12 families. The pharmacological models used in the studies together with the mechanistic discussions and the chemical composition of the essential oils are also detailed. The data clearly demonstrate the antispasmodic effect of the essential oils from the aromatic plant species studied. Further research is needed in order to ascertain the therapeutic importance of these findings. Full article

(This article belongs to the Special Issue Biological Activities of Essential Oils)

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