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Chemical Composition and Bioactivities of Essential Oils
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Chemical Composition and Bioactivities of Essential Oils

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (15 March 2023) | Viewed by 39062

Special Issue Editor

Dr. Manuela Labbozzetta

E-Mail Website
Guest Editor
Department of Biological, Chemical and Pharmaceutical Science and Technology (STEBICEF), University of Palermo, Palermo, Italy
Interests: pharmacology; chemotherapy; multidrug resistance; natural products; pharmacognosy and phytotherapy
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Identifying, testing and implementing the use of new medicinal plants in current therapeutic protocols is a very complex, time-consuming and costly process. In many situations, the focus is on the study of plant extracts as it is known that in some cases the activity of the phytocomplex is higher than that of pure phytochemicals due to the synergism of the molecular structures. Plant secondary metabolites, including essential oils (EOs), may in fact be one of the best sources for identifying promising new therapies. Essential oils are volatile, natural complex compounds characterized by a strong odor and in nature they play an important role in protecting plants from biotic and abiotic stresses. The biological properties of EOs are widely documented by the extensive literature demonstrating their antitumor, antibioceptive, antiviral, antiphlogistic and antimicrobial activity in vitro.  Furthermore, essential oils contain different chemical classes of compounds whose heterogeneity of active parts can help prevent the development of drug resistance. Therefore, due to their low toxicity, good pharmacokinetics and multitarget action, EOs represent important alternatives to synthetic chemicals as promising drugs for use in therapy.

The purpose of this Special Issue, entitled "Chemical Composition and Bioactivity of Essential Oils", is to provide an update on the phytochemical composition of plant extracts and analyze the bioactivity of essential oils and their constituents in different models of study, in vitro and in vivo.

Major topics of interest include, but are not limited to the following:

  • Extraction, isolation and characterization of bioactive compounds from plant extracts;
  • Evaluation of the antioxidant, antitumor and antimicrobial activity of essential oils and their constituents;
  • Evaluation of the activity of essential oils in multi-drug resistance models.

Dr. Manuela Labbozzetta
Guest Editor

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Keywords

  • bioactive natural compounds
  • essential oils
  • chemical characterization
  • the essential oil mechanism of action
  • the biological activities in vitro and in vivo
  • antitumor
  • antimicrobials
  • anti-infectious
  • antioxidant

Published Papers (16 papers)

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14 pages, 1271 KiB  
Article
Chemical Variability and Chemotype Concept of Essential Oils from Algerian Wild Plants
by Fatima Zahra Benomari, Mathieu Sarazin, Djamel Chaib, André Pichette, Hinane Boumghar, Yacine Boumghar and Nassim Djabou
Molecules 2023, 28(11), 4439; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28114439 - 30 May 2023
Cited by 5 | Viewed by 1334
Abstract
The chemical compositions of eleven wild species of aromatic and medicinal plants indigenous to Algeria, including Thymus, Mentha, Rosmarinus, Lavandula, and Eucalyptus, were analyzed. The identification of the chemical composition of each oil was conducted using GC-FID and GC-MS capillary gas chromatography. The [...] Read more.
The chemical compositions of eleven wild species of aromatic and medicinal plants indigenous to Algeria, including Thymus, Mentha, Rosmarinus, Lavandula, and Eucalyptus, were analyzed. The identification of the chemical composition of each oil was conducted using GC-FID and GC-MS capillary gas chromatography. The study investigated the chemical variability of the essential oils based on several parameters. These included the impact of the vegetative cycle on oil composition, variations among subspecies of the same species, variations among species within the same genus, the influence of environmental factors on composition variations within a species, chemo typing, and the genetic factors (such as hybridization) contributing to chemical variability. The concepts of chemotaxonomy, chemotype, and chemical markers were examined to understand their limitations and emphasize the importance of regulating the use of essential oils derived from wild plants. The study advocates for an approach that involves the domestication of wild plants and screening their chemical compositions according to more specific standards for each commercially available oil. Lastly, the nutritional implications and the variability of nutritional impact based on the chemical composition of the essential oils will be discussed. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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12 pages, 518 KiB  
Article
Chemical Composition, Enantiomeric Distribution and Biological Activity of Essential Oil from Morella pubescens (Humb. & Bonpl. ex Willd.) Wilbur
by Eduardo Valarezo, Carlos Correa-Jaramillo, Paola Astudillo-Dávila, Julio Garzón-Yaguache, Luis Cartuche, Miguel Angel Meneses and Vladimir Morocho
Molecules 2023, 28(7), 2910; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28072910 - 24 Mar 2023
Viewed by 1310
Abstract
The species Morella pubescens, commonly known as wax laurel, is a tree belonging to the Myricaceae family that can be found from Costa Rica to Bolivia. In this study, the chemical composition, enantiomeric distribution, and biological activity of essential oil isolated from [...] Read more.
The species Morella pubescens, commonly known as wax laurel, is a tree belonging to the Myricaceae family that can be found from Costa Rica to Bolivia. In this study, the chemical composition, enantiomeric distribution, and biological activity of essential oil isolated from the leaves of this species was determined. Hydrodistillation was used to isolate the essential oil (EO). Gas chromatography coupled with mass spectrometry was used to determine the qualitative composition, gas chromatography equipped with a flame ionization detector was used to determine quantitative composition, and gas chromatography on an enantioselective column was used to determine enantiomeric distribution. The broth microdilution method was employed to assess the antibacterial capacity of the essential oil against seven opportunistic microorganisms, including three Gram-positive cocci bacteria, a Gram-positive bacilli bacterium and three Gram-negative bacilli bacteria. 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid radical cation and 2,2-diphenyl-1-picrylhydryl free radical were used as reagents to determine the antioxidant activity of essential oil. The spectrophotometric method was used to analyze the acetylcholinesterase inhibitory effect of the essential oil. The extraction method afforded a low yield of around 0.076 ± 0.008% (v/w). Fifty-eight chemical compounds, which represent 97.9% of the total composition, were identified in the essential oil. Sesquiterpene hydrocarbons were the most representative group with 24 compounds (67.8%). The principal constituents were (E)-caryophyllene (27.5 ± 1.3%), limonene (11.8 ± 0.6%), δ-selinene (9.1 ± 0.2%), β-selinene (8.0 ± 0.2%), selina-3,7(11)-diene (5.3 ± 0.2%) and germacrene B (5.0 ± 0.5%). Three pairs of enantiomers were identified in the essential oil of Morella pubescens. Essential oil presented strong activity against the bacterium Enterococcus faecium (ATCC 27270) with an MIC of 250 μg/mL. The antioxidant activity of essential oil was very strong in the ABTS method with an SC50 of 46.4 ± 1.0 µg/mL and was strong in the DPPH method with an SC50 of 237.1 ± 1.8 µg/mL. Additionally, the essential oil reported strong anticholinesterase activity with an IC50 of 133.5 ± 1.06 µg/mL. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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10 pages, 528 KiB  
Article
Lavandula angustifolia Essential Oils as Effective Enhancers of Fluconazole Antifungal Activity against Candida albicans
by Michalina Adaszyńska-Skwirzyńska, Małgorzata Dzięcioł and Danuta Szczerbińska
Molecules 2023, 28(3), 1176; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28031176 - 25 Jan 2023
Cited by 5 | Viewed by 2584
Abstract
The increasing prevalence of Candida albicans resistance to commercial antifungal agents in recent decades has prompted modern medicine and veterinary medicine to search for combined treatment options. The aim of the study was to determine the activity of essential oils from different cultivars [...] Read more.
The increasing prevalence of Candida albicans resistance to commercial antifungal agents in recent decades has prompted modern medicine and veterinary medicine to search for combined treatment options. The aim of the study was to determine the activity of essential oils from different cultivars and morphological parts of the medicinal lavender (Lavandula angustifolia) in combination with fluconazole against Candida albicans ATCC 10231 strain. The effect of the combination of lavender essential oil with fluconazole was tested using the checkerboard method, and the obtained results were interpreted on the basis of fractional inhibitory concentration indices (FICIs). A synergistic interaction was found for all combinations of fluconazole with essential oils isolated both from flowers and leafy stalks of two tested lavender cultivars: ‘Blue River’ and ‘Ellagance Purple’. The observed enhancement effect of fluconazole antifungal activity was significantly stronger in the case of essential oils obtained from flowers and leafy stalks of ‘Blue River’ cultivar. Analogous studies were performed for linalool, one of the main components of lavender essential oils, and a similar synergistic interaction with fluconazole was found. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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14 pages, 1357 KiB  
Article
Multivariate Analysis of Essential Oil Composition of Artemisia annua L. Collected from Different Locations in Korea
by Minji Hong, Minju Kim, Haejung Jang, Sela Bo, Ponnuvel Deepa, Kandhasamy Sowndhararajan and Songmun Kim
Molecules 2023, 28(3), 1131; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28031131 - 23 Jan 2023
Cited by 6 | Viewed by 1962
Abstract
Artemisia annua L. is distributed throughout the world and it is an important medicinal plant in Korea to treat various human diseases. Recently, A. annua has also been considered to be an effective ethnobotanical drug against COVID-19. A. annua contains an appreciable amount [...] Read more.
Artemisia annua L. is distributed throughout the world and it is an important medicinal plant in Korea to treat various human diseases. Recently, A. annua has also been considered to be an effective ethnobotanical drug against COVID-19. A. annua contains an appreciable amount of essential oil with different biological properties. However, the composition of essential oils in aromatic plants can be varied depending on several factors, including geographic, genetic, ecological, etc. Hence, the present study aimed to investigate the chemical diversity of essential oils of Korean A. annua collected from different locations in Korea by multivariate analysis. For this purpose, the seeds of A. annua were collected from 112 different locations in Korea and were grown under the same environmental conditions. Except for nine individuals which decayed during the cultivation, essential oils were isolated from the aerial parts of 103 A. annua individuals (AEOs) using the steam distillation extraction method, and their chemical compositions were determined by GC-MS analysis. Furthermore, a multivariate analysis was performed to distinguish the difference between 103 individuals of A. annua based on their essential oil compositions. The yield of A. annua essential oils ranged from 0.04 to 1.09% (v/w). Based on the GC-MS data, A. annua individuals were grouped into six chemotypes such as artemisia ketone, camphor, β-cubebene, eucalyptol, α-pinene, and β-selinene. The multivariate analysis results revealed that Korean A. annua could be largely grouped into three clusters such as artemisia ketone, eucalyptol, and β-selinene. Among 35 components selected for principal component analysis (PCA), PC1, PC2, and PC3 accounted for 82.55%, 8.74%, and 3.62%, respectively. Although all individuals of A. annua were cultivated under the same environmental conditions, there is an intraspecific chemical diversity that exists within Korean native species. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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9 pages, 266 KiB  
Article
Chemical Composition and Antimicrobial Activity against Phytopathogenic Fungi of Essential Oils Obtained from Echinophora tenuifolia subsp. sibthorpiana Grown in Wild and Cultivated Conditions in Turkey
by Arif Sanli and Fatma Zehra Ok
Molecules 2023, 28(2), 585; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28020585 - 06 Jan 2023
Cited by 3 | Viewed by 1469
Abstract
The hydro-distilled essential oils obtained from aerial parts of the wild and cultivated Echinophora tenuifolia subsp. sibthorpiana have been analyzed by GC-MS and screened for antimicrobial activity. In total, 28 compounds representing more than 99% of the oils were identified. α-phellandrene (13.22% and [...] Read more.
The hydro-distilled essential oils obtained from aerial parts of the wild and cultivated Echinophora tenuifolia subsp. sibthorpiana have been analyzed by GC-MS and screened for antimicrobial activity. In total, 28 compounds representing more than 99% of the oils were identified. α-phellandrene (13.22% and 55.27%), δ-3-carene (49.29% and 4.03%), and methyl eugenol (22.59–25.69%) were found as the main components for the wild and cultivated oils, respectively. EOs of the wild and cultivated plants differed significantly in both the percentage of the main components and antifungal effect. α-phellandrene was more dominant in cultivated plants (55.27%) than in wild ones (13.22%), while δ-3-carene was more abundant in the wild plants (49.29%). In the antifungal assays, both oils displayed moderate to high activity against three phytopathogenic fungi; Fusarium oxysporum, Rhizoctonia solani, and Alternaria alternata. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
16 pages, 639 KiB  
Article
In Vitro and In Silico Pharmacological and Cosmeceutical Potential of Ten Essential Oils from Aromatic Medicinal Plants from the Mascarene Islands
by Bibi Sharmeen Jugreet, Namrita Lall, Isa Anina Lambrechts, Anna-Mari Reid, Jacqueline Maphutha, Marizé Nel, Abdallah H. Hassan, Asaad Khalid, Ashraf N. Abdalla, Bao Le Van and Mohamad Fawzi Mahomoodally
Molecules 2022, 27(24), 8705; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27248705 - 08 Dec 2022
Cited by 7 | Viewed by 1784
Abstract
In this study, 10 essential oils (EOs), from nine plants (Cinnamomum camphora, Curcuma longa, Citrus aurantium, Morinda citrifolia, Petroselinum crispum, Plectranthus amboinicus, Pittosporum senacia, Syzygium coriaceum, and Syzygium samarangense) were assessed for their [...] Read more.
In this study, 10 essential oils (EOs), from nine plants (Cinnamomum camphora, Curcuma longa, Citrus aurantium, Morinda citrifolia, Petroselinum crispum, Plectranthus amboinicus, Pittosporum senacia, Syzygium coriaceum, and Syzygium samarangense) were assessed for their antimicrobial, antiaging and antiproliferative properties. While only S. coriaceum, P. amboinicus (MIC: 0.50 mg/mL) and M. citrifolia (MIC: 2 mg/mL) EOs showed activity against Cutibacterium acnes, all EOs except S. samarangense EO demonstrated activity against Mycobacterium smegmatis (MIC: 0.125–0.50 mg/mL). The EOs were either fungistatic or fungicidal against one or both tested Candida species with minimum inhibitory/fungicidal concentrations of 0.016–32 mg/mL. The EOs also inhibited one or both key enzymes involved in skin aging, elastase and collagenase (IC50: 89.22–459.2 µg/mL; 0.17–0.18 mg/mL, respectively). Turmerone, previously identified in the C. longa EO, showed the highest binding affinity with the enzymes (binding energy: −5.11 and −6.64 kcal/mol). Only C. aurantium leaf, C. longa, P. amboinicus, P. senacia, S. coriaceum, and S. samarangense EOs were cytotoxic to the human malignant melanoma cells, UCT-MEL1 (IC50: 88.91–277.25 µg/mL). All the EOs, except M. citrifolia EO, were also cytotoxic to the human keratinocytes non-tumorigenic cells, HaCat (IC50: 33.73–250.90 µg/mL). Altogether, some interesting therapeutic properties of the EOs of pharmacological/cosmeceutical interests were observed, which warrants further investigations. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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15 pages, 2143 KiB  
Article
Essential Oil Chemotypes and Genetic Variability of Cinnamomum verum Leaf Samples Commercialized and Cultivated in the Amazon
by Júlia Karla A. M. Xavier, Talissa Gabriele C. Baia, Oscar Victor C. Alegria, Pablo Luis B. Figueiredo, Adriana R. Carneiro, Edith Cibelle de O. Moreira, José Guilherme S. Maia, William N. Setzer and Joyce Kelly R. da Silva
Molecules 2022, 27(21), 7337; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27217337 - 28 Oct 2022
Cited by 4 | Viewed by 1735
Abstract
Cinnamomum verum (Lauraceae), also known as “true cinnamon” or “Ceylon cinnamon” has been widely used in traditional folk medicine and cuisine for a long time. The systematics of C. verum presents some difficulties due to genetic variation and morphological similarity between other Cinnamomum [...] Read more.
Cinnamomum verum (Lauraceae), also known as “true cinnamon” or “Ceylon cinnamon” has been widely used in traditional folk medicine and cuisine for a long time. The systematics of C. verum presents some difficulties due to genetic variation and morphological similarity between other Cinnamomum species. The present work aimed to find chemical and molecular markers of C. verum samples from the Amazon region of Brazil. The leaf EOs and the genetic material (DNA) were extracted from samples cultivated and commercial samples. The chemical composition of the essential oils from samples of C. verum cultivated (Cve1-Cve5) and commercial (Cve6-c-Cv9-c) was grouped by multivariate statistical analysis of Principal Component Analysis (PCA). The major compounds were rich in benzenoids and phenylpropanoids, such as eugenol (0.7–91.0%), benzyl benzoate (0.28–76.51%), (E)-cinnamyl acetate (0.36–32.1%), and (E)-cinnamaldehyde (1.0–19.73%). DNA barcodes were developed for phylogenetic analysis using the chloroplastic regions of the matK and rbcL genes, and psbA-trnH intergenic spacer. The psbA-trnH sequences provided greater diversity of nucleotides, and matK confirmed the identity of C. verum. The combination of DNA barcode and volatile profile was found to be an important tool for the discrimination of C. verum varieties and to examine the authenticity of industrial sources. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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14 pages, 1197 KiB  
Article
Variations in the Chemical Composition of Essential Oils in Native Populations of Korean Thyme, Thymus quinquecostatus Celak.
by Minju Kim, Kandhasamy Sowndhararajan, Ponnuvel Deepa and Songmun Kim
Molecules 2022, 27(21), 7203; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27217203 - 24 Oct 2022
Cited by 3 | Viewed by 1273
Abstract
The genus Thymus (Lamiaceae) contains numerous medicinally important species. Among them, Thymus quinquecostatus Celak. has been extensively utilized as a traditional medicine and a food flavoring agent in the Korean peninsula, owing to its unique aroma. In particular, T. quinquecostatus has been used [...] Read more.
The genus Thymus (Lamiaceae) contains numerous medicinally important species. Among them, Thymus quinquecostatus Celak. has been extensively utilized as a traditional medicine and a food flavoring agent in the Korean peninsula, owing to its unique aroma. In particular, T. quinquecostatus has been used for the treatment of gastroenteritis, inflammation, stomach problems, liver disease, arthritis, arteriosclerosis, and menstrual problems. This study aimed to investigate the chemical diversity of essential oils among 103 Korean native populations of T. quinquecostatus. For this purpose, seedlings of T. quinquecostatus populations were purchased from different regions in the Korean Peninsula, and seedlings were grown in the experimental field under the same environmental conditions. The chemical compositions of steam-distilled essential oils were determined using GC-MS. In total, 212 components were identified from 103 populations of T. quinquecostatus. Furthermore, principal component analysis (PCA) was performed in order to understand variations in the essential oil compositions among 103 Korean native populations of T. quinquecostatus. According to the essential oil compositions, 30 components were selected for PCA. Based on the most abundant essential oil components, four chemotypes were identified in T. quinquecostatus populations. PCA and cluster analyses revealed that 103 individuals of T. quinquecostatus could be classified into four clusters, such as thymol, geraniol, geranyl acetate, and linalool. Furthermore, dendrogram construction demonstrated that geraniol and geranyl acetate, as well as linalool and thymol groups, were closely related. This study suggested the significant chemical polymorphism of essential oils in local populations of T. quinquecostatus in Korea. It could be concluded that the intraspecific variations in the essential oil compositions may be associated with genetic diversity among the individuals. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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11 pages, 2418 KiB  
Article
Chemical Diversity of Essential Oils from Korean Native Populations of Agastache rugosa (Korean Mint)
by Minji Hong, Ponnuvel Deepa, Ki-Yeon Lee, Kyunghee Kim, Kandhasamy Sowndhararajan and Songmun Kim
Molecules 2022, 27(19), 6341; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27196341 - 26 Sep 2022
Cited by 3 | Viewed by 1523
Abstract
Agastache rugosa (baechohyang) is one of the most important aromatic plants native to the Republic of Korea. A. rugosa fragrance has been used to prepare incense since the Goryeo Dynasty in Korea. The present study aimed to explore the variation in the composition [...] Read more.
Agastache rugosa (baechohyang) is one of the most important aromatic plants native to the Republic of Korea. A. rugosa fragrance has been used to prepare incense since the Goryeo Dynasty in Korea. The present study aimed to explore the variation in the composition of essential oils from A. rugosa among native populations in Korea. The seeds of A. rugosa were collected from 90 different sites in Korea and seedlings were raised in the nursery. Essential oils were extracted from these populations by the steam distillation extraction method and their chemical compositions were analyzed by GC-MS. The yield of essential oils of A. rugosa ranged between 0.11% and 0.86%. A total of 204 components were identified from 90 populations of A. rugosa. Out of 204 components, 32 components were common in more than 40 individuals of A. rugosa and these 32 components were selected for principal component analysis (PCA). On the basis of the essential oil compositions, six chemotypes—estragole, pulegone, methyl eugenol, menthone, isopulegone, and nepetalactone—were distinguished according to their major components. As a result of the cluster analysis, 90 individuals of A. rugosa could be classified into three groups: estragole, methyl eugenol, and pulegone. A. rugosa exhibited significant chemical diversity among the individuals. The distribution of chemotypes is associated with the collection of seeds, suggesting that genetic diversity may influence the variations in the chemical compositions and concentrations within the species. This chemical diversity serves as the background to select cultivars for the cultivation and industrial applications of A. rugosa cultivars with high essential oil yield and concentration of its chemical components. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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17 pages, 874 KiB  
Article
Neutrophil Immunomodulatory Activity of (−)-Borneol, a Major Component of Essential Oils Extracted from Grindelia squarrosa
by Igor A. Schepetkin, Gulmira Özek, Temel Özek, Liliya N. Kirpotina, Andrei I. Khlebnikov and Mark T. Quinn
Molecules 2022, 27(15), 4897; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27154897 - 31 Jul 2022
Cited by 5 | Viewed by 1935
Abstract
Grindelia squarrosa (Pursh) Dunal is used in traditional medicine for treating various diseases; however, little is known about the immunomodulatory activity of essential oils from this plant. Thus, we isolated essential oils from the flowers (GEOFl) and leaves (GEOLv) [...] Read more.
Grindelia squarrosa (Pursh) Dunal is used in traditional medicine for treating various diseases; however, little is known about the immunomodulatory activity of essential oils from this plant. Thus, we isolated essential oils from the flowers (GEOFl) and leaves (GEOLv) of G. squarrosa and evaluated the chemical composition and innate immunomodulatory activity of these essential oils. Compositional analysis of these essential oils revealed that the main components were α-pinene (24.7 and 23.2% in GEOFl and GEOLv, respectively), limonene (10.0 and 14.7%), borneol (23.4 and 16.6%), p-cymen-8-ol (6.1 and 5.8%), β-pinene (4.0 and 3.8%), bornyl acetate (3.0 and 5.1%), trans-pinocarveol (4.2 and 3.7%), spathulenol (3.0 and 2.0%), myrtenol (2.5 and 1.7%), and terpinolene (1.7 and 2.0%). Enantiomer analysis showed that α-pinene, β-pinene, and borneol were present primarily as (−)-enantiomers (100% enantiomeric excess (ee) for (−)-α-pinene and (−)-borneol in both GEOFl and GEOLv; 82 and 78% ee for (−)-β-pinene in GEOFl and GEOLv), while limonene was present primarily as the (+)-enantiomer (94 and 96 ee in GEOFl and GEOLv). Grindelia essential oils activated human neutrophils, resulting in increased [Ca2+]i (EC50 = 22.3 µg/mL for GEOFl and 19.4 µg/mL for GEOLv). In addition, one of the major enantiomeric components, (−)-borneol, activated human neutrophil [Ca2+]i (EC50 = 28.7 ± 2.6), whereas (+)-borneol was inactive. Since these treatments activated neutrophils, we also evaluated if they were able to down-regulate neutrophil responses to subsequent agonist activation and found that treatment with Grindelia essential oils inhibited activation of these cells by the N-formyl peptide receptor 1 (FPR1) agonist fMLF and the FPR2 agonist WKYMVM. Likewise, (−)-borneol inhibited FPR-agonist-induced Ca2+ influx in neutrophils. Grindelia leaf and flower essential oils, as well as (−)-borneol, also inhibited fMLF-induced chemotaxis of human neutrophils (IC50 = 4.1 ± 0.8 µg/mL, 5.0 ± 1.6 µg/mL, and 5.8 ± 1.4 µM, respectively). Thus, we identified (−)-borneol as a novel modulator of human neutrophil function. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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14 pages, 716 KiB  
Article
Preliminary Study on Phytochemical Constituents and Biological Activities of Essential Oil from Myriactis nepalensis Less.
by Jikai Fu, Yang Gao and Xiang Xing
Molecules 2022, 27(14), 4631; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27144631 - 20 Jul 2022
Cited by 6 | Viewed by 2017
Abstract
In response to the need for novel therapeutic strategies to combat the development of microbial resistance, plant essential oils may represent a promising alternative source. This study set out to characterize the chemical composition and assess the antibacterial potential of Myriactis nepalensis Less. [...] Read more.
In response to the need for novel therapeutic strategies to combat the development of microbial resistance, plant essential oils may represent a promising alternative source. This study set out to characterize the chemical composition and assess the antibacterial potential of Myriactis nepalensis Less. essential oil (MNEO). Essential oil isolated from M. nepalensis by hydrodistillation was analyzed using a GC–MS technique. The antibacterial properties of MNEO alone and combined with antibiotics (chloramphenicol and streptomycin) were tested via the disc diffusion, microbroth dilution, and checkerboard methods. MNEO was represented by oxygenated sesquiterpenes (60.3%) and sesquiterpene hydrocarbons (28.6%), with caryophyllene oxide, spathulenol, humulene epoxide II, β-elemene, neointermedeol, and β-caryophyllene as the main compounds. MNEO exhibited a strong antibacterial effect against Gram-positive bacteria, with MIC and MBC values of 0.039 mg/mL and 0.039–0.156 mg/mL, respectively, and synergistic effects were observed in both combinations with chloramphenicol and streptomycin. Furthermore, the antibiofilm and cytotoxic activities of MNEO were also evaluated. The crystal violet assay was used for quantification of Staphylococcus aureus biofilm formation, and an MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay was conducted to determine cell viability. The results revealed MNEO could dose-dependently inhibit Staphylococcus aureus biofilm formation and possessed potential cytotoxic on both normal and cancer cells (IC50 values from 13.13 ± 1.90 to 35.22 ± 8.36 μg/mL). Overall, the results indicate that MNEO may have promising applications in the field of bacterial infections. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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12 pages, 1542 KiB  
Article
Antitumor Effect of Glandora rosmarinifolia (Boraginaceae) Essential Oil through Inhibition of the Activity of the Topo II Enzyme in Acute Myeloid Leukemia
by Manuela Labbozzetta, Paola Poma, Chiara Occhipinti, Maurizio Sajeva and Monica Notarbartolo
Molecules 2022, 27(13), 4203; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27134203 - 29 Jun 2022
Cited by 1 | Viewed by 1650
Abstract
It was previously shown that the antitumor and cytotoxic activity of the essential oil (EO) extracted from the aerial parts of Glandora rosmarinifolia appears to involve a pro-oxidant mechanism in hepatocellular carcinoma (HCC) and in triple-negative breast cancer (TNBC) cell lines. Its most [...] Read more.
It was previously shown that the antitumor and cytotoxic activity of the essential oil (EO) extracted from the aerial parts of Glandora rosmarinifolia appears to involve a pro-oxidant mechanism in hepatocellular carcinoma (HCC) and in triple-negative breast cancer (TNBC) cell lines. Its most abundant compound is a hydroxy-methyl-naphthoquinone isomer. Important pharmacological activities, such as antitumor, antibacterial, antifungal, antiviral and antiparasitic activities, are attributed to naphthoquinones, probably due to their pro-oxidant or electrophilic potential; for some naphthoquinones, a mechanism of action of topoisomerase inhibition has been reported, in which they appear to act both as catalytic inhibitors and as topoisomerase II poisons. Our aim was to evaluate the cytotoxic activity of the essential oil on an acute myeloid leukemia cell line HL-60 and on its multidrug-resistant (MDR) variant HL-60R and verify its ability to interfere with topoisomerase II activity. MTS assay showed that G. rosmarinifolia EO induced a decrease in tumor cell viability equivalent in the two cell lines; this antitumor effect could depend on the pro-oxidant activity of EO in both cell lines. Furthermore, G. rosmarinifolia EO reduced the activity of Topo II in the nuclear extracts of HL-60 and HL-60R cells, as inferred from the inability to convert the kinetoplast DNA into the decatenated form and then not inducing linear kDNA. Confirming this result, flow cytometric analysis proved that EO induced a G0-G1 phase arrest, with cell reduction in the S-phase. In addition, the combination of EO with etoposide showed a good potentiation effect in terms of cytotoxicity in both cell lines. Our results highlight the antitumor activity of EO in the HL-60 cell line and its MDR variant with a peculiar mechanism as a Topo II modulator. Unlike etoposide, EO does not cause stabilization of a covalent Topo II-DNA intermediate but acts as a catalytic inhibitor. These data make G. rosmarinifolia EO a potential anticancer drug candidate due to its cytotoxic action, which is not affected by multidrug resistance. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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11 pages, 2095 KiB  
Article
Effect of the Instant Controlled Pressure Drop Technology in Cardamom (Elettaria cardamomum) Essential Oil Extraction and Antioxidant Activity
by Giselle Dení Teresa-Martínez, Anaberta Cardador-Martínez, Carmen Téllez-Pérez, Karim Allaf, Cristian Jiménez-Martínez and Maritza Alonzo-Macías
Molecules 2022, 27(11), 3433; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27113433 - 26 May 2022
Cited by 5 | Viewed by 3352
Abstract
Green cardamom (Elettaria cardamomum) is an outspread spice native to Asia, which is well appreciated for its sensory characteristics, delicate aroma, and unique taste. Currently, the main cardamom extracts are essential oils (EOs), and regarding current market tendencies, this market is [...] Read more.
Green cardamom (Elettaria cardamomum) is an outspread spice native to Asia, which is well appreciated for its sensory characteristics, delicate aroma, and unique taste. Currently, the main cardamom extracts are essential oils (EOs), and regarding current market tendencies, this market is in high growth. For this reason, technologies such as the instant controlled pressure drop (DIC) have been applied to reach higher yields and better quality of EO. Then, this study explores the impact of DIC as a pretreatment before hydrodistillation (HD) on the EO yield and their antioxidant activity. Obtained results showed that the coupling of DIC-HD increased the yield of essential oil and also had a positive impact on their antioxidant capacity. The EO yield of DIC-HD (140 °C and 30 s) was 4.43% vs. 2.52% for control; the AOX of DIC-HD (165 °C and 30 s) was 86% inhibition vs. 57.02% for control, and the TEAC of DIC-HD (140 °C and 30 s) was 1.44 uMTE/g EO vs. 13.66 uMTE/g EO. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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11 pages, 1567 KiB  
Article
Phytochemical Constituents and Ameliorative Effect of the Essential Oil from Annona muricata L. Leaves in a Murine Model of Breast Cancer
by Juan Pedro Rojas-Armas, Jorge Luis Arroyo-Acevedo, Miriam Palomino-Pacheco, José Manuel Ortiz-Sánchez, James Calva, Hugo Jesus Justil-Guerrero, Americo Castro-Luna, Norma Ramos-Cevallos, Edwin César Cieza-Macedo and Oscar Herrera-Calderon
Molecules 2022, 27(6), 1818; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27061818 - 10 Mar 2022
Cited by 4 | Viewed by 2772
Abstract
Annona muricata leaves are traditionally used as an anticancer plant in the world. The aim of this study was to evaluate the ameliorative effect of the essential oil from Annona muricata leaves (EOAm) in an experimental model of breast cancer and to determine [...] Read more.
Annona muricata leaves are traditionally used as an anticancer plant in the world. The aim of this study was to evaluate the ameliorative effect of the essential oil from Annona muricata leaves (EOAm) in an experimental model of breast cancer and to determine the volatile constituents with gas chromatography-mass spectrometry (GC-MS). Thirty female rats were assigned to five groups: the control group; the DMBA (7,12-dimethylbenz[α]anthracene) group; and three groups received daily EOAm doses of 50, 100, and 200 mg/kg/day, plus DMBA, respectively. After 13 weeks of treatment, tumors were analyzed pathologically and biochemical markers in serum were noted. As a result, in GC-MS analysis, 40 compounds were identified and 4 of them were abundant: Z-caryophyllene (40.22%), followed by α-selinene (9.94%), β-pinene (8.92%), and β-elemene (7.48%). Furthermore, EOAm in a dose-dependent form produced a reduction in tumor frequency and the accumulated tumor volume was reduced by 50% and 71% with doses of 100 and 200 mg/kg, respectively. Serum levels of reduced glutathione (GSH) increased and malondialdehyde (MDA) decreased significantly compared to the DMBA group. Serum levels of vascular endothelial growth factor (VEGF) decreased significantly from 70.75 ± 7.15 pg/mL in the DMBA group to 46.50 ± 9.00 and 34.13 ± 11.50 pg/mL in groups treated with doses of 100 and 200 mg/kg, respectively. This study concludes that the EOAm leaves showed an ameliorative effect in a murine model of breast cancer. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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Review

Jump to: Research

23 pages, 587 KiB  
Review
The Effects of Essential Oils on the Nervous System: A Scoping Review
by Apsorn Sattayakhom, Sineewanlaya Wichit and Phanit Koomhin
Molecules 2023, 28(9), 3771; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28093771 - 27 Apr 2023
Cited by 11 | Viewed by 7971
Abstract
Essential oils are a mixture of natural aromatic volatile oils extracted from plants. The use of essential oils is ancient, and has prevailed in different cultures around the world, such as those of the Egyptians, Greeks, Persians, and Chinese. Today, essential oils are [...] Read more.
Essential oils are a mixture of natural aromatic volatile oils extracted from plants. The use of essential oils is ancient, and has prevailed in different cultures around the world, such as those of the Egyptians, Greeks, Persians, and Chinese. Today, essential oils are used in traditional and complimentary medicines, aromatherapy, massage therapies, cosmetics, perfumes and food industries. The screening effect of essential oils has been studied worldwide. They demonstrate a range of biological activities, such as antiparasitic, antifungal, antibacterial, antiviral, antioxidant, anti-inflammatory, anticancer, antiaging, and neuroprotective properties. In this scoping review, we provide a 10-year updated comprehensive assessment of volatile oils and their effects on the nervous system. MEDLINE, Scopus, and Google Scholar were systematically and strategically searched for original studies investigating these effects from 2012 to 2022. Approximately seventy studies were selected as included studies. Among these studies, several outcomes were reported, including antistress, antianxiety, analgesic, cognitive, and autonomic effects. Some essential oils showed developmental benefits, with the potential to induce neurite outgrowth. The neurotransmitter receptor level can also be modified by essential oil application. Physiological and pathophysiological outcome measures were reported. For physiological outcomes, arousal, cognitive performance, circadian eating behavior, emotional modulation, consumer acceptance, preferences, and willingness to buy were investigated. For pathophysiological conditions, pain, depression, anxiety, stress, sleep disorder, mental fatigue, agitated behavior, and quality of life were measured. In conclusion, essential oils showed promising effects on the nervous system, which can be further applied to their use in functional foods, drinks, and alternative therapy. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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13 pages, 900 KiB  
Review
Immune Defences: A View from the Side of the Essential Oils
by Vivian Tullio, Janira Roana, Lorenza Cavallo and Narcisa Mandras
Molecules 2023, 28(1), 435; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28010435 - 03 Jan 2023
Cited by 5 | Viewed by 2887
Abstract
The use of essential oils is increasingly being investigated among new therapeutic approaches based on medicinal plants and their extracts. With the wide use of synthetic and semi-synthetic antimicrobial drugs, the spread of drug-resistant clinical isolates has increased, and research is directed towards [...] Read more.
The use of essential oils is increasingly being investigated among new therapeutic approaches based on medicinal plants and their extracts. With the wide use of synthetic and semi-synthetic antimicrobial drugs, the spread of drug-resistant clinical isolates has increased, and research is directed towards natural products, such as essential oils, as useful antimicrobial resources. In the context of a prospective infection, we compared the impact of essential oils and common antimicrobial agents on the microbicidal activity of human phagocytes. Here, we present the results of our decades-long investigation into the effectiveness of thyme red oil (26.52% thymol chemotype), tea tree oil (TTO), and Mentha of Pancalieri [(Mentha x piperita (Huds) var. officinalis (Sole), form rubescens (Camus) (Lamiaceae)] essential oils on human polymorphonuclear leukocytes (PMNs) capacity to kill clinical strains of Candida albicans and C. krusei when compared to three antifungal drugs used to treat candidiasis (fluconazole, anidulafungin, and caspofungin) These essential oils demonstrate antifungal drug-like and/or superior efficacy in enhancing intracellular killing by PMNs, even at subinhibitory concentrations. Our results are compared with data in the literature on essential oils and immune system interactions. This comparison would aid in identifying therapeutic solutions to the increasingly prevalent antibiotic resistance as well as filling in any remaining knowledge gaps on the bioactivity of essential oils. Full article
(This article belongs to the Special Issue Chemical Composition and Bioactivities of Essential Oils)
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