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The Chemistry of Essential Oils

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

Deadline for manuscript submissions: closed (30 September 2021) | Viewed by 61407

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Prof. Dr. Luca Valgimigli

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Department of Chemistry “G. Ciamician”, University of Bologna, 40126 Bologna, Italy
Interests: antioxidants; radical chemistry; essential oils; organic reaction mechanisms; phytocomponents
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Dear Colleagues,

Essential oils have been attracting continuous interest in the last two decades. In addition to their many biological properties, which have stimulated interest in them in the biomedical field, in recent years, their components, particularly terpenoids, have gained importance as building blocks for the synthesis of novel drugs and the use of camphor and limonene to obtain multipotent derivatives of cannabidiol, are just examples. Phenylpropanoid derivatives have also emerged as a promising family of bioactive molecules. Terpenes and terpenoids are also being investigated as renewable feedstocks in the chemical industry to replace fossil sources of olefins. At the same time, they serve as templates for bioinspired novel materials. Finally, better understanding of their redox chemistry has opened the way to the rational exploitation of their potential as antioxidants.

This special issue welcomes original research articles and reviews on the many aspects of the chemistry of essential oils and their components, including but not limited to their role in drug discovery, in the development of sustainable or bioinspired materials, their role as antioxidants, the aspects related to their analysis and characterization, and advancement in the methods for their extraction.

Prof. Dr. Luca Valgimigli
Guest Editor

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Keywords

Essential oils
Terpenoids
Phenylpropanoids
Bioinspired drugs
Sustainable materials
Antioxidants

Published Papers (12 papers)

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13 pages, 702 KiB

Open AccessFeature PaperArticle

Chemical Composition of Essential Oils from Leaves and Fruits of Juniperus foetidissima and Their Attractancy and Toxicity to Two Economically Important Tephritid Fruit Fly Species, Ceratitis capitata and Anastrepha suspensa

by Mehmet Kurtca, Ibrahim Tumen, Hasan Keskin, Nurhayat Tabanca, Xiangbing Yang, Betul Demirci and Paul E. Kendra

Molecules 2021, 26(24), 7504; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26247504 - 11 Dec 2021

Cited by 3 | Viewed by 2866

Abstract

The present study analyzed the chemical composition of Juniperus foetidissima Willd. essential oils (EOs) and evaluated their attractancy and toxicity to two agriculturally important tephritid fruit flies. The composition of hydrodistilled EOs obtained from leaves (JFLEO) and fruits (JFFEO) of J. foetidissima was analyzed by GC–FID and GC–MS. The main compounds were α-pinene (45%) and cedrol (18%) in the JFLEO and α-pinene (42%), α-thujone (12%), and β-thujone (25%) in the JFFEO. In behavioral bioassays of the male Mediterranean fruit fly, Ceratitis capitata (Wiedemann), both JFLEO and JFFEO showed strong attraction comparable to that observed with two positive controls, Melaleuca alternifolia and Tetradenia riparia EOs. In topical bioassays of the female Caribbean fruit fly, Anastrepha suspensa (Loew), the toxicity of JFFEO was two-fold higher than that of JFLEO, with the LD₅₀ values being 10.46 and 22.07 µg/µL, respectively. This could be due to differences in chemical components between JFLEO and JFFEO. The JFFEO was dominated by 48% monoterpene hydrocarbons (MH) and 46% oxygenated monoterpenes (OM), while JFLEO consisted of 57% MH, 18% OM, and 20% oxygenated sesquiterpenes (OS). This is the first study to evaluate the attractancy and toxicity of J. foetidissima EOs to tephritid fruit flies. Our results indicate that JFFEO has the potential for application to the management of pest tephritid species, and further investigation is warranted. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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9 pages, 567 KiB

Open AccessArticle

Chemical Analysis and In Vitro Bioactivity of Essential Oil of Laurelia sempervirens and Safrole Derivatives against Oomycete Fish Pathogens

by Alejandro Madrid, Ana Lizeth Morales, Valentina Saffirio, Mauricio A. Cuellar, Enrique Werner, Bastián Said, Patricio Godoy, Nelson Caro, Mirna Melo and Iván Montenegro

Molecules 2021, 26(21), 6551; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216551 - 29 Oct 2021

Cited by 1 | Viewed by 1678

Abstract

In this study, the essential oil (EO) from Laurelia sempervirens was analyzed by GC/MS and safrole (1) was identified as the major metabolite 1, was subjected to direct reactions on the oxygenated groups in the aromatic ring and in the side chain, and eight compounds (4 to 12) were obtained by the process. EO and compounds 4–12 were subjected to biological assays on 24 strains of the genus Saprolegnia, specifically of the species 12 S. parasitica and 12 S. australis. EO showed a significant effect against Saprolegnia strains. Compound 6 presents the highest activity against two resistant strains, with minimum inhibitory concentration (MIC) and minimum oomyceticidal concentration (MOC) values of 25 to 100 and 75 to 125 µg/mL, respectively. The results show that compound 6 exhibited superior activities compared to the commercial controls bronopol and azoxystrobin used to combat these pathogens. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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12 pages, 2635 KiB

Open AccessArticle

Machine Learning Data Augmentation as a Tool to Enhance Quantitative Composition–Activity Relationships of Complex Mixtures. A New Application to Dissect the Role of Main Chemical Components in Bioactive Essential Oils

by Alessio Ragno, Anna Baldisserotto, Lorenzo Antonini, Manuela Sabatino, Filippo Sapienza, Erika Baldini, Raissa Buzzi, Silvia Vertuani and Stefano Manfredini

Molecules 2021, 26(20), 6279; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26206279 - 17 Oct 2021

Cited by 3 | Viewed by 1945

Abstract

Scientific investigation on essential oils composition and the related biological profile are continuously growing. Nevertheless, only a few studies have been performed on the relationships between chemical composition and biological data. Herein, the investigation of 61 assayed essential oils is reported focusing on their inhibition activity against Microsporum spp. including development of machine learning models with the aim of highlining the possible chemical components mainly related to the inhibitory potency. The application of machine learning and deep learning techniques for predictive and descriptive purposes have been applied successfully to many fields. Quantitative composition–activity relationships machine learning-based models were developed for the 61 essential oils tested as Microsporum spp. growth modulators. The models were built with in-house python scripts implementing data augmentation with the purpose of having a smoother flow between essential oils’ chemical compositions and biological data. High statistical coefficient values (Accuracy, Matthews correlation coefficient and F₁ score) were obtained and model inspection permitted to detect possible specific roles related to some components of essential oils’ constituents. Robust machine learning models are far more useful tools to reveal data augmentation in comparison with raw data derived models. To the best of the authors knowledge this is the first report using data augmentation to highlight the role of complex mixture components, in particular a first application of these data will be for the development of ingredients in the dermo-cosmetic field investigating microbial species considering the urge for the use of natural preserving and acting antimicrobial agents. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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14 pages, 1309 KiB

Open AccessFeature PaperArticle

Adulteration of Essential Oils: A Multitask Issue for Quality Control. Three Case Studies: Lavandula angustifolia Mill., Citrus limon (L.) Osbeck and Melaleuca alternifolia (Maiden & Betche) Cheel

by Francesca Capetti, Arianna Marengo, Cecilia Cagliero, Erica Liberto, Carlo Bicchi, Patrizia Rubiolo and Barbara Sgorbini

Molecules 2021, 26(18), 5610; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26185610 - 16 Sep 2021

Cited by 20 | Viewed by 3899

Abstract

The quality control of essential oils (EO) principally aims at revealing the presence of adulterations and at quantifying compounds that are limited by law by evaluating EO chemical compositions, usually in terms of the normalised relative abundance of selected markers, for comparison to reference values reported in pharmacopoeias and/or international norms. Common adulterations of EO consist of the addition of cheaper EO or synthetic materials. This adulteration can be detected by calculating the percent normalised areas of selected markers or the enantiomeric composition of chiral components. The dilution of the EO with vegetable oils is another type of adulteration. This adulteration is quite devious, as it modifies neither the qualitative composition of the resulting EO nor the marker’s normalised percentage abundance, which is no longer diagnostic, and an absolute quantitative analysis is required. This study aims at verifying the application of the two above approaches (i.e., normalised relative abundance and absolute quantitation) to detect EO adulterations, with examples involving selected commercial EO (lavender, bergamot and tea tree) adulterated with synthetic components, EO of different origin and lower economical values and heavy vegetable oils. The results show that absolute quantitation is necessary to highlight adulteration with heavy vegetable oils, providing that a reference quantitative profile is available. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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23 pages, 2455 KiB

Open AccessArticle

Simultaneous Hydrodistillation-Steam Distillation of Rosmarinus officinalis, Lavandula angustifolia and Citrus aurantium from Morocco, Major Terpenes: Impact on Biological Activities

by Sara El Kharraf, Maria Leonor Faleiro, Farah Abdellah, Soukaïna El-Guendouz, El Mestafa El Hadrami and Maria Graça Miguel

Molecules 2021, 26(18), 5452; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26185452 - 07 Sep 2021

Cited by 15 | Viewed by 2973

Abstract

Interest in the use of essential oils (EOs) in the biomedical and food industries have seen growing over the last decades due to their richness in bioactive compounds. The challenges in developing an EO extraction process that assure an efficient levels of monoterpenes with impact on biological activities have driven the present study, in which the EO extraction process of rosemary, lavender and citrus was performed by simultaneous hydrodistillation–steam distillation, and the influence of EO composition on biological activities, namely antioxidant, anti-inflammatory, antidiabetic, anti-acetylcholinesterase, anti-tyrosinase, antibacterial, and antibiofilm activity, were evaluated. The EO yields of combinations were generally higher than the individual plants (R. officinalis (Ro), L. angustifolia (La), and C. aurantium (Ca)) extracted by the conventional hydrodistillation. The EOs obtained by this process generally had a better capacity for scavenging the free radicals, inhibiting α-glucosidase, and acetylcholinesterase activities than the individual EOs. The combination of EOs did not improve the ability for scavenging peroxide hydrogen or the capacity for inhibiting lipoxygenase activity. The antioxidant activity or the enzyme inhibition activity could not only be attributed to their major compounds because they presented lower activities than the EOs. The chemical composition of the combination Ro:La:Ca, at the ratio 1/6:1/6:2/3, was enriched in 1,8-cineole, linalool, and linalyl acetate and resulted in lower MIC values for all tested strains in comparison with the ratio 1/6:2/3:1/6 that was deprived on those components. The biofilm formation of Gram positive and Gram negative bacteria was impaired by the combination Ro:La:Ca at a sub-inhibitory concentration. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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12 pages, 915 KiB

Open AccessArticle

Absolute Antioxidant Activity of Five Phenol-Rich Essential Oils

by Yafang Guo, Romeo Pizzol, Simone Gabbanini, Andrea Baschieri, Riccardo Amorati and Luca Valgimigli

Molecules 2021, 26(17), 5237; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175237 - 29 Aug 2021

Cited by 11 | Viewed by 2489

Abstract

Essential oils (EOs) have promising antioxidant activities which are gaining interest as natural alternatives to synthetic antioxidants in the food and cosmetic industries. However, quantitative data on chain-breaking activity and on the kinetics of peroxyl radical trapping are missing. Five phenol-rich EOs were analyzed by GC-MS and studied by oxygen-uptake kinetics in inhibited controlled autoxidations of reference substrates (cumene and squalene). Terpene-rich Thymus vulgaris (thymol 4%; carvacrol 33.9%), Origanum vulgare, (thymol 0.4%; carvacrol 66.2%) and Satureja hortensis, (thymol 1.7%; carvacrol 46.6%), had apparent k_inh (30 °C, PhCl) of (1.5 ± 0.3) × 10⁴, (1.3 ± 0.1) × 10⁴ and (1.1 ± 0.3) × 10⁴ M⁻¹s⁻¹, respectively, while phenylpropanoid-rich Eugenia caryophyllus (eugenol 80.8%) and Cinnamomum zeylanicum, (eugenol 81.4%) showed apparent k_inh (30 °C, PhCl) of (5.0 ± 0.1) × 10³ and (4.9 ± 0.3) × 10³ M⁻¹s⁻¹, respectively. All EOs already granted good antioxidant protection of cumene at a concentration of 1 ppm (1 mg/L), the duration being proportional to their phenolic content, which dictated their antioxidant behavior. They also afforded excellent protection of squalene after adjusting their concentration (100 mg/L) to account for the much higher oxidizability of this substrate. All investigated EOs had k_inh comparable to synthetic butylated hydroxytoluene (BHT) were are eligible to replace it in the protection of food or cosmetic products. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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13 pages, 1448 KiB

Open AccessArticle

Effect of the Distillation Time on the Chemical Composition, Antioxidant Potential and Antimicrobial Activity of Essential Oils from Different Cannabis sativa L. Cultivars

by Sara Palmieri, Francesca Maggio, Marika Pellegrini, Antonella Ricci, Annalisa Serio, Antonello Paparella and Claudio Lo Sterzo

Molecules 2021, 26(16), 4770; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26164770 - 06 Aug 2021

Cited by 20 | Viewed by 3346

Abstract

Within the unavoidable variability of various origins in the characteristics of essential oils, the aim of this study was to evaluate the effect of the distillation time on the chemical composition and biological activity of Cannabis sativa essential oils (EOs). The dry inflorescences came from Carmagnola, Kompolti, Futura 75, Gran Sasso Kush and Carmagnola Lemon varieties from Abruzzo region (Central Italy), the last two being new cultivar here described for the first time. EOs were collected at 2 h and 4 h of distillation; GC/MS technique was applied to characterize their volatile fraction. The EOs were evaluated for total polyphenol content (TPC), antioxidant capacity (AOC) and antimicrobial activity against food-borne pathogens and spoilage bacteria. The time of distillation particularly influenced EOs chemical composition, extracting more or less terpenic components, but generally enriching with minor sesquiterpenes and cannabidiol. A logical response in ratio of time was observed for antioxidant potential, being the essential oils at 4 h of distillation more active than those distilled for 2 h, and particularly Futura 75. Conversely, except for Futura 75, the effect of time on the antimicrobial activity was variable and requires further investigations; nevertheless, the inhibitory activity of all EOs against Pseudomonas fluorescens P34 was an interesting result. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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14 pages, 1580 KiB

Open AccessFeature PaperArticle

Oregano and Thyme Essential Oils Encapsulated in Chitosan Nanoparticles as Effective Antimicrobial Agents against Foodborne Pathogens

by Giuseppe Granata, Stefano Stracquadanio, Marco Leonardi, Edoardo Napoli, Graziella Malandrino, Viviana Cafiso, Stefania Stefani and Corrada Geraci

Molecules 2021, 26(13), 4055; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26134055 - 02 Jul 2021

Cited by 46 | Viewed by 3796

Abstract

The use of natural compounds with biocidal activity to fight the growth of bacteria responsible for foodborne illness is one of the main research challenges in the food sector. This study reports the preparation and physicochemical characterization of chitosan nanoparticles loaded with Thymus capitatus (Th-CNPs) and Origanum vulgare (Or-CNPs) essential oils. The nanosystems were obtained by ionotropic gelation technique with high encapsulation efficiency (80–83%) and loading capacity (26–27%). Nanoparticles showed a spherical shape, bimodal particle size distribution, and good stability (zeta potential values > 40 mV). The treatment of the nanosuspensions at different temperatures (4 and 40 °C) and storage times (7, 15, 21, and 30 days) did not affect their physicochemical parameters and highlights their reservoir ability for essential oils also under stressful conditions. Both Or-CNPs and Th-CNPs exhibited an enhanced bactericidal activity against foodborne pathogens (S. aureus, E. coli, L. monocytogenes) than pure essential oils. These ecofriendly nanosystems could represent a valid alternative to synthetic preservatives and be of interest for health and food safety. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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12 pages, 1025 KiB

Open AccessArticle

Variability of the Chemical Composition of the Essential Oil from the Amazonian Ishpingo Species (Ocotea quixos)

by Eduardo Valarezo, Antoine Vullien and Dayra Conde-Rojas

Molecules 2021, 26(13), 3961; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26133961 - 28 Jun 2021

Cited by 8 | Viewed by 2317

Abstract

Ocotea quixos (Lam.) Kosterm. is an aromatic tree native to Ecuador, whose leaves are used to prepare aromatic beverages to which different health benefits are attributed. In this study, Ocotea quixos leaves were collected in the Amazon region in different environmental conditions and subjected to hydrodistillation to isolate the essential oil. The collection variables used were type of soil, amount of shade, and height; in addition, the presence of twig and leaf age and moisture were used as variables. Chemical composition was analyzed by means of gas chromatography equipped with a flame ionization detector and gas chromatography coupled to mass spectrometry. A wide variety of chemical compositions were detected in the samples. In total, forty-seven compounds were identified, which represented between 97.17% and 99.89% of the total composition. The constituents were mainly grouped into aliphatic sesquiterpene hydrocarbons (33.03–55.89%), other compounds (8.94–47.83%), and oxygenated monoterpenes (1.97–39.66%). The main constituents were found to be (E)-cinnamyl acetate (5.96–41.65%), (E)-methyl cinnamate (0.38–37.91%), and trans-caryophyllene (8.77–37.02%). The statistical analysis suggested the existence of two essential oil chemotypes and a direct correlation between environmental conditions and chemical composition of the essential oils. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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12 pages, 2305 KiB

Open AccessArticle

Molecules Present in Plant Essential Oils for Prevention and Treatment of Colorectal Cancer (CRC)

by Giovannamaria Petrocelli, Fulvia Farabegoli, Maria Chiara Valerii, Catia Giovannini, Alberto Sardo and Enzo Spisni

Molecules 2021, 26(4), 885; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26040885 - 08 Feb 2021

Cited by 21 | Viewed by 3799

Abstract

Essential oils (EOs) are a complex mixture of hydrophobic and volatile compounds synthesized from aromatic plants, commonly present in the human diet. In recent years, many in vitro studies have suggested possible anticancer properties of single EO compounds, on colorectal cancer (CRC) cells. However, the majority of these studies did not compare the effects of these compounds on normal and cancer colon cells. By using NCM-460, a normal human mucosal epithelial cell line, Caco-2, a human colon epithelial adenocarcinoma cell line, and SW-620, colon cancer cells derived from lymph node metastatic site, we identified cinnamaldehyde, derived from cinnamon EO and eugenol, derived from bud clove EO, as compounds with a specific anticancer action selectively targeting the transformed colonic cells. Both cinnamaldehyde (75 µM) and eugenol (800 µM), after 72 h of treatment, were capable to induce apoptosis, necrosis and a cell cycle slowdown in Caco-2 and in SW-620, but not in NCM-460 cells. If associated with a targeted delivery to the colon, these two compounds could prove effective in the prevention or treatment of CRC. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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Review

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33 pages, 41004 KiB

Open AccessReview

In Vitro Studies on Therapeutic Effects of Cannabidiol in Neural Cells: Neurons, Glia, and Neural Stem Cells

by Jungnam Kim, Hyunwoo Choi, Eunhye K. Kang, Gil Yong Ji, Youjeong Kim and Insung S. Choi

Molecules 2021, 26(19), 6077; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26196077 - 08 Oct 2021

Cited by 11 | Viewed by 5272

Abstract

(‒)-Cannabidiol (CBD) is one of the major phytocannabinoids extracted from the Cannabis genus. Its non-psychoactiveness and therapeutic potential, partly along with some anecdotal—if not scientific or clinical—evidence on the prevention and treatment of neurological diseases, have led researchers to investigate the biochemical actions of CBD on neural cells. This review summarizes the previously reported mechanistic studies of the CBD actions on primary neural cells at the in vitro cell-culture level. The neural cells are classified into neurons, microglia, astrocytes, oligodendrocytes, and neural stem cells, and the CBD effects on each cell type are described. After brief introduction on CBD and in vitro studies of CBD actions on neural cells, the neuroprotective capability of CBD on primary neurons with the suggested operating actions is discussed, followed by the reported CBD actions on glia and the CBD-induced regeneration from neural stem cells. A summary section gives a general overview of the biochemical actions of CBD on neural cells, with a future perspective. This review will provide a basic and fundamental, but crucial, insight on the mechanistic understanding of CBD actions on neural cells in the brain, at the molecular level, and the therapeutic potential of CBD in the prevention and treatment of neurological diseases, although to date, there seem to have been relatively limited research activities and reports on the cell culture-level, in vitro studies of CBD effects on primary neural cells. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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16 pages, 4616 KiB

Open AccessReview

The Cannabis Terpenes

by Sarana Rose Sommano, Chuda Chittasupho, Warintorn Ruksiriwanich and Pensak Jantrawut

Molecules 2020, 25(24), 5792; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25245792 - 08 Dec 2020

Cited by 82 | Viewed by 25580

Abstract

Terpenes are the primary constituents of essential oils and are responsible for the aroma characteristics of cannabis. Together with the cannabinoids, terpenes illustrate synergic and/or entourage effect and their interactions have only been speculated in for the last few decades. Hundreds of terpenes are identified that allude to cannabis sensory attributes, contributing largely to the consumer’s experiences and market price. They also enhance many therapeutic benefits, especially as aromatherapy. To shed light on the importance of terpenes in the cannabis industry, the purpose of this review is to morphologically describe sources of cannabis terpenes and to explain the biosynthesis and diversity of terpene profiles in different cannabis chemovars. Full article

(This article belongs to the Special Issue The Chemistry of Essential Oils)

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