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Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application

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

Deadline for manuscript submissions: closed (30 May 2022) | Viewed by 42614

Special Issue Editors

Dr. Asta Judžentienė

E-Mail Website
Guest Editor
Center for Physical Sciences and Technology (CPST),Organic Chemistry Department, Saulėtekio av. 3, LT-10257 Vilnius, Lithuania
Interests: plant biodiversity; secondary metabolites; essential oils; terpenes; chemical variability of natural compounds; chromatography (TLC, GC, HPLC), Mass Spectrometry (MS); phytochemistry; bioactivity; statistical data analysis
Dr. Kristina Ložienė

E-Mail Website
Guest Editor
Nature Research Centre, Institute of Botany, Laboratory of Economic Botany, Akademijos Str. 2, LT-08412 Vilnius, Lithuania
Interests: Medicinal and Aromatic Plants; Phytochemistry; Secondary Plant Metabolites; Essential Oils; Tannins; GC Chromatography; Mass Spectrometry; Plant Population Biology; Plant Resources; Economic Botany

Special Issue Information

Dear Colleagues,

In line with the progress of chemistry, not only have the structures and biosynthetic pathways of many natural compounds been discovered, but synthetic analogues have also been created. Although these nature-identical chemical compounds are less expensive, they do not always replicate all the characteristics and biological activities of natural compounds. Furthermore, synthetic analogues are more likely to trigger allergic reactions and reduce resistance to microorganisms. Secondary plant metabolites are eco-friendly compounds with a wide range of biological activities and a variety of applications in pharmaceuticals, cosmetics, food, agriculture and other fields. Essential oils and other kinds of herbal extracts are mixtures of various constituents with different properties and different mechanisms of bio-action, which may work in synergy. Therefore, the search for methods of isolating secondary metabolites from plants, to investigate their biological activity and potential applications, is highly relevant.

The aim of this Special Issue is to provide a forum for leading scientists and academics all over the world to share their latest research achievements and to discuss new ideas and developments in the area of bioactive phytochemistry.

In this Special Issue, original and review articles, as well as short communications, on this topic are welcome.

We look forward to reviewing your contributions.

Dr. Asta Judžentienė
Dr. Kristina Ložienė
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Medicinal and aromatical plant resources
  • Plant extracts
  • Essential oils
  • Secondary metabolites
  • Chromatography
  • Mass spectrometry
  • Bioactivity
  • Synergism
  • Application

Published Papers (16 papers)

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19 pages, 2032 KiB  
Article
In Vitro Antioxidant and Prooxidant Activities of Red Raspberry (Rubus idaeus L.) Stem Extracts
by Rasa Garjonyte, Jurga Budiene, Linas Labanauskas and Asta Judzentiene
Molecules 2022, 27(13), 4073; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27134073 - 24 Jun 2022
Cited by 4 | Viewed by 2199
Abstract
Leaves and stems of red raspberry (Rubus idaeus) are used in Lithuanian folk medicine. Healing properties of raspberry are related to the content of bioactive compounds, mainly polyphenols. Extracts of raspberry leaves contained higher total phenolic content (TPC) (1290 mg/L, expressed [...] Read more.
Leaves and stems of red raspberry (Rubus idaeus) are used in Lithuanian folk medicine. Healing properties of raspberry are related to the content of bioactive compounds, mainly polyphenols. Extracts of raspberry leaves contained higher total phenolic content (TPC) (1290 mg/L, expressed in gallic acid equivalent) compared to that in extracts of stems or peeled bark (up to 420 mg/L and 598 mg/L, respectively). To find out whether the collection time of herbal material was critical for the properties of the extracts, the stems were collected at different times of the year. TPC in the extracts depended more on extraction conditions rather than on the sampling time. Antioxidant activity of raspberry stem and bark extracts tested by spectrophotometric (DPPH● scavenging) and electrochemical (cyclic and differential pulse voltammetry) assays correlated with TPC. DPPH radical scavenging activity values for stem, leaf, and bark extracts were as follows: ≤1.18 ± 0.07, 1.63 ± 0.10, and ≤1.90 ± 0.04 (mmol/L, TROLOX equivalent), respectively. Assessed electrochemically, hydrogen peroxide-scavenging activity of extracts was independent on TPC. The latter activity was related to the presence of some protein in the extract as revealed by gel electrophoresis. Prooxidant activity of raspberry stem extracts was dependent on solution pH and temperature. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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14 pages, 4790 KiB  
Article
Ultrastructural Damages to H1N1 Influenza Virus Caused by Vapor Essential Oils
by Valentina Noemi Madia, Walter Toscanelli, Daniela De Vita, Marta De Angelis, Antonella Messore, Davide Ialongo, Luigi Scipione, Valeria Tudino, Felicia Diodata D’Auria, Roberto Di Santo, Stefania Garzoli, Annarita Stringaro, Marisa Colone, Magda Marchetti, Fabiana Superti, Lucia Nencioni and Roberta Costi
Molecules 2022, 27(12), 3718; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27123718 - 09 Jun 2022
Cited by 7 | Viewed by 2335
Abstract
Influenza viruses are transmitted from human to human via airborne droplets and can be transferred through contaminated environmental surfaces. Some works have demonstrated the efficacy of essential oils (EOs) as antimicrobial and antiviral agents, but most of them examined the liquid phases, which [...] Read more.
Influenza viruses are transmitted from human to human via airborne droplets and can be transferred through contaminated environmental surfaces. Some works have demonstrated the efficacy of essential oils (EOs) as antimicrobial and antiviral agents, but most of them examined the liquid phases, which are generally toxic for oral applications. In our study, we describe the antiviral activity of Citrus bergamia, Melaleuca alternifolia, Illicium verum and Eucalyptus globulus vapor EOs against influenza virus type A. In the vapor phase, C. bergamia and M. alternifolia strongly reduced viral cytopathic effect without exerting any cytotoxicity. The E. globulus vapor EO reduced viral infection by 78% with no cytotoxicity, while I. verum was not effective. Furthermore, we characterized the EOs and their vapor phase by the head-space gas chromatography–mass spectrometry technique, observing that the major component found in each liquid EO is the same one of the corresponding vapor phases, with the exception of M. alternifolia. To deepen the mechanism of action, the morphological integrity of virus particles was checked by negative staining transmission electron microscopy, showing that they interfere with the lipid bilayer of the viral envelope, leading to the decomposition of membranes. We speculated that the most abundant components of the vapor EOs might directly interfere with influenza virus envelope structures or mask viral structures important for early steps of viral infection. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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16 pages, 860 KiB  
Article
Phytochemical Variability of Essential Oils of Two Balkan Endemic Species: Satureja pilosa Velen. and S. kitaibelii Wierzb. ex Heuff. (Lamiaceae)
by Valtcho D. Zheljazkov, Ivanka B. Semerdjieva, Charles L. Cantrell, Tess Astatkie and Milica Aćimović
Molecules 2022, 27(10), 3153; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27103153 - 14 May 2022
Cited by 4 | Viewed by 1547
Abstract
Satureja pilosa and S. kitaibelii (Lamiaceae) are Balkan endemic plant species, and the composition of their essential oil (EO) is highly variable. The aim of the present study was to establish: (1) the EO variability in two populations of S. pilosa (the intrapopulation), [...] Read more.
Satureja pilosa and S. kitaibelii (Lamiaceae) are Balkan endemic plant species, and the composition of their essential oil (EO) is highly variable. The aim of the present study was to establish: (1) the EO variability in two populations of S. pilosa (the intrapopulation), and (2) the EO variation in S. kitaibelii between nine populations (interpopulation) from Bulgaria and two from Serbia. The EOs of two Satureja species were obtained from aboveground plant parts by hydrodistillation and were analyzed by GC/MS/FID. Overall, the EO yield on the intrapopulation level of S. pilosa varied from 0.54% to 2.15%, while the EO of S. kitaibelii varied from 0.04% to 0.43% (interpopulation). The EO of S. pilosa was found to contain thymol and carvacrol as the main constituents, with other major constituents being p-cymene and γ-terpinene. S. pilosa samples in both studied populations formed six chemical groups. The major constituents (p-cymene, terpinen-4-ol, bornyl acetate, γ-muurolene, endo-borneol, cis-β-ocimene, trans-β-ocimene, carvacrol, α-pinene, thymoquinone, geranial, geranyl acetate, spathulenol, and caryophyllene oxide) of S. kitaibelii EO were considered for grouping the populations into ten chemotypes. The present study is the first report on the interpopulation diversity of S. kitaibelii EOs in Bulgaria. It demonstrated variability of the EOs between and within the populations of S. kitaibelii from Bulgaria. This study identified promising genetic material that could be further propagated and developed into cultivars for commercial production of S. kitaibelii and S. pilosa, thereby reducing the impact of collection on wild populations. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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19 pages, 722 KiB  
Article
Antioxidant and Toxic Activity of Helichrysum arenarium (L.) Moench and Helichrysum italicum (Roth) G. Don Essential Oils and Extracts
by Asta Judzentiene, Jurga Budiene, Irena Nedveckyte and Rasa Garjonyte
Molecules 2022, 27(4), 1311; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27041311 - 15 Feb 2022
Cited by 14 | Viewed by 3786
Abstract
Helichrysum arenarium (L.) Moench (sandy everlasting) is the only species from genus Helichrysum Mill that grows spontaneously in Lithuania. The chemical composition of the essential oils (EOs) from inflorescences and leaves of H. arenarium wild plants was analysed by GC-MS. Palmitic (≤23.8%), myristic [...] Read more.
Helichrysum arenarium (L.) Moench (sandy everlasting) is the only species from genus Helichrysum Mill that grows spontaneously in Lithuania. The chemical composition of the essential oils (EOs) from inflorescences and leaves of H. arenarium wild plants was analysed by GC-MS. Palmitic (≤23.8%), myristic (≤14.9%) and lauric (6.1%) acids, n-nonanal (10.4%), and trans-β-caryophyllene (≤6.5%) were the major constituents in the EOs. For comparison, the main components in EO from flowers (commercial herb material) of H.italicum were γ-curcumene (21.5%), β-selinene (13.6%), α-selinene (8.1%), β-eudesmol (8.3%), and α-pinene (6.5%). Composition of H. arenarium methanolic extracts was investigated by HPLC-DAD-TOF. The main compounds were the following: luteolin-7-O-glucoside, naringenin and its glucoside, apigenin, chlorogenic acid, arenol, and arzanol. Antioxidant activity of EOs and extracts was tested by DPPH● and ABTS●+ assays. Sandy everlasting extracts exhibited significantly higher radical scavenging activities (for leaves 11.18 to 19.13 and for inflorescences 1.96 to 6.13 mmol/L TROLOX equivalent) compared to those of all tested EOs (0.25 to 0.46 mmol/L TROLOX equivalent). Antioxidant activity, assayed electrochemically by cyclic and square wave voltammetry correlated with total polyphenolic content in extracts and radical scavenging properties of EOs and extracts. The toxic activity of EOs of both Helichrysum species was evaluated using a brine shrimp (Artemia salina) bioassay. H. italicum inflorescence EO was found to be toxic (LC50 = 15.99 µg/mL) as well as that of H. arenarium (LC50 ≤ 23.42 µg/mL) oils. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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15 pages, 624 KiB  
Article
Geraniol and Carvacrol in Essential Oil Bearing Thymus pulegioides: Distribution in Natural Habitats and Phytotoxic Effect
by Kristina Ložienė and Vaida Vaičiulytė
Molecules 2022, 27(3), 986; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030986 - 01 Feb 2022
Cited by 2 | Viewed by 1744
Abstract
Phenolic and non-phenolic chemotypes of Thymus pulegioides L. are common in Europe. Essential oils of these chemotypes, as various compositions of allelochemicals, can have different phytotoxic effects on neighboring plants in natural habitats. The aim of this study was to establish the distribution [...] Read more.
Phenolic and non-phenolic chemotypes of Thymus pulegioides L. are common in Europe. Essential oils of these chemotypes, as various compositions of allelochemicals, can have different phytotoxic effects on neighboring plants in natural habitats. The aim of this study was to establish the distribution of carvacrol and geraniol in T. pulegioides, growing wild in Lithuania, and compare phytotoxity of essential oils of carvacrol and geraniol chemotypes on selected plant species. In investigating 131 T. pulegioides habitats, essential oils were isolated by hydrodistillation and analyzed by GC-FID and GC-MS. Phytotoxity of essential oils extracted from carvacrol and geraniol chemotypes transmitted through water and air to selected plants was determined under laboratory conditions. Pharmacologically valuable Hypericum perforatum L. and the important forage grass Phleum pratense L. were respectively selected for experimentation from among 35 medicinal plants and 10 feed Poaceae species, growing in T. pulegioides habitats. Field results showed that carvacrol is common throughout Lithuania’s territory, whereas the geraniol is predominantly located under the continental climatic conditions of the eastern region of the country. In the laboratory experiment, it was established that there was stronger inhibition of P. pratense seed germination by the essential oil of the geraniol chemotype than the carvacrol chemotype. None of the H. perforatum seeds germinated after exposure to the essential oil of the geraniol chemotype. In general, this study builds on previous studies by providing further evidence that different T. pulegioides chemotypes have contrasting phytotoxic effects on neighboring plants within their natural habitats. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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17 pages, 2528 KiB  
Article
Quinolizidine-Based Variations and Antifungal Activity of Eight Lupinus Species Grown under Greenhouse Conditions
by Willy Cely-Veloza, Diego Quiroga and Ericsson Coy-Barrera
Molecules 2022, 27(1), 305; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27010305 - 04 Jan 2022
Cited by 10 | Viewed by 2235
Abstract
Fusarium oxysporum is an aggressive phytopathogen that affects various plant species, resulting in extensive local and global economic losses. Therefore, the search for competent alternatives is a constant pursuit. Quinolizidine alkaloids (QA) are naturally occurring compounds with diverse biological activities. The structural diversity [...] Read more.
Fusarium oxysporum is an aggressive phytopathogen that affects various plant species, resulting in extensive local and global economic losses. Therefore, the search for competent alternatives is a constant pursuit. Quinolizidine alkaloids (QA) are naturally occurring compounds with diverse biological activities. The structural diversity of quinolizidines is mainly contributed by species of the family Fabaceae, particularly the genus Lupinus. This quinolizidine-based chemo diversity can be explored to find antifungals and even mixtures to address concomitant effects on F. oxysporum. Thus, the antifungal activity of quinolizidine-rich extracts (QREs) from the leaves of eight greenhouse-propagated Lupinus species was evaluated to outline promising QA mixtures against F. oxysporum. Thirteen main compounds were identified and quantified using an external standard. Quantitative analysis revealed different contents per quinolizidine depending on the Lupinus plant, ranging from 0.003 to 32.8 mg/g fresh leaves. Bioautography showed that all extracts were active at the maximum concentration (5 µg/µL). They also exhibited >50% mycelium growth inhibition. All QREs were fungistatic except for the fungicidal QRE of L. polyphyllus Lindl. Angustifoline, matrine, 13α-hydroxylupanine, and 17-oxolupanine were ranked to act jointly against the phytopathogen. Our findings constitute reference information to better understand the antifungal activity of naturally afforded QA mixtures from these globally important plants. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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11 pages, 1119 KiB  
Article
Phytochemical Profile, Antimicrobial, Cytotoxic, and Antioxidant Activities of Fresh and Air-Dried Satureja nabateorum Essential Oils
by Nawaf Al-Maharik and Nidal Jaradat
Molecules 2022, 27(1), 125; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27010125 - 26 Dec 2021
Cited by 3 | Viewed by 2450
Abstract
Satureja nabateorum (Danin and Hedge) Bräuchler is a perennial herb in the Lamiaceae family that was discovered and classified in 1998. This green herb is restricted to the mountains overlooking the Dead Sea, specifically in Jordan’s southwest, the Edom mountains, and the Tubas [...] Read more.
Satureja nabateorum (Danin and Hedge) Bräuchler is a perennial herb in the Lamiaceae family that was discovered and classified in 1998. This green herb is restricted to the mountains overlooking the Dead Sea, specifically in Jordan’s southwest, the Edom mountains, and the Tubas mountains in Palestine. Gas chromatography-mass spectrometry (GC-MS) analysis of essential oil (EO) of air-dried and fresh S. nabateorum resulted in the identification of 30 and 42 phytochemicals accounting for 99.56 and 98.64% of the EO, respectively. Thymol (46.07 ± 1.1 and 40.64 ± 1.21%) was the major compound, followed by its biosynthetic precursors γ-terpinene (21.15 ± 1.05% and 20.65 ± 1.12%), and p-cymene (15.02 ± 1.02% and 11.51 ± 0.97%), respectively. Microdilution assay was used to evaluate the antimicrobial property of EOs against Staphylococcus aureus (ATCC 25923), clinical isolate Methicillin-Resistant Staphylococcus aureus (MRSA), Enterococcus faecium (ATCC 700221) Klebsiella pneumoniae (ATCC 13883), Proteus vulgaris (ATCC 700221), Escherichia coli (ATCC 25922) and Pseudomonas aeruginosa (ATCC 27853) and Candida albicans (ATCC-90028). With a MIC of 0.135 μg/mL, the EOs has the most potent antibacterial action against K. pneumonia. Both EOs display good antifungal efficacy against C. albicans, with a MIC value of 0.75 μg/mL, which was better than that of Fluconazole’s (positive control, MIC = 1.56 μg/mL). The antioxidant capacity of EOs extracted from air-dried and fresh S. nabateorum was determined using the DPPH assay, with IC50 values of 4.78 ± 0.41 and 5.37 ± 0.40 μg/mL, respectively. The tested EOs showed significant cytotoxicity against Hela, HepG2, and COLO-205 cells, with IC50 values ranging from 82 ± 0.98 to 256 ± 1.95 μg/mL. The current work shows there is a possibility to use the S. nabateorum EOs for various applications. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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12 pages, 2008 KiB  
Article
Thymus algeriensis and Artemisia herba-alba Essential Oils: Chemical Analysis, Antioxidant Potential and In Vivo Anti-Inflammatory, Analgesic Activities, and Acute Toxicity
by Khadija El Ouahdani, Imane Es-safi, Hamza Mechchate, Mohammed Al-zahrani, Ashraf Ahmed Qurtam, Mohammed Aleissa, Amina Bari and Dalila Bousta
Molecules 2021, 26(22), 6780; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26226780 - 10 Nov 2021
Cited by 21 | Viewed by 2608
Abstract
The study of bioactive molecules of natural origin is a focus of current research. Thymus algeriensis and Artemisia herba-alba are two medicinal plants widely used by the Moroccan population in the traditional treatment of several pathologies linked to inflammation. This study aimed to [...] Read more.
The study of bioactive molecules of natural origin is a focus of current research. Thymus algeriensis and Artemisia herba-alba are two medicinal plants widely used by the Moroccan population in the traditional treatment of several pathologies linked to inflammation. This study aimed to evaluate the single and combined antioxidant, anti-inflammatory and analgesic effects of the essential oils extracted from these two medicinal plants, and also their potential toxicity. Essential oils were extracted using hydro-distillation in a Clevenger-type apparatus. The antioxidant activity was evaluated by two methods: the scavenging of the free radical DPPH, and the reduction in iron. Anti-inflammatory activity was evaluated by evaluating the edema development induced by carrageenan injecting, while the analgesic power was evaluated according to the number of abdominal contortions induced by the intraperitoneal injection of acetic acid (0.7%). The acute oral toxicity was performed to assess the potential toxicity of the studied EOs, followed by an analysis of the blood biochemical parameters. The results of the two antioxidant tests indicated that our extract mixture exhibits good iron reduction capacity and very interesting DPPH free radical scavenging power, with an IC50 of around 4.38 ± 0.98 μg/mL higher than that of the benchmark antioxidant, BHT. The anti-inflammatory test demonstrated that the mixture administered orally at a dose of 150 mg/kg has a better activity, exceeding that of 1% Diclofenac, with a percentage of maximum inhibition of the edema of 89.99 ± 4.08. The number of cramps in the mice treated with the mixture at a dose of 150 mg/kg is significantly lower (29.80 ± 1.92) than those of the group treated with Tramadol (42.00 ± 2.70), respectively. The toxicity results show no signs of toxicity with an LD50 greater than 150 mg/Kg. These interesting results show that the two plants’ EOs had an important anti-inflammatory, analgesic, and antioxidant activity, and also a powerful synergistic effect, which encourages further in-depth investigations on their pharmacological proprieties. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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15 pages, 22954 KiB  
Article
Combination of Analytical and Statistical Methods in Order to Optimize Antibacterial Activity of Clary Sage Supercritical Fluid Extracts
by Csongor Bakó, Viktória Lilla Balázs, Gyöngyi Takács, József Péter Pallos, Szilárd Pál, Béla Kocsis, Dóra Rippelné Pethő and Györgyi Horváth
Molecules 2021, 26(21), 6449; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216449 - 26 Oct 2021
Cited by 4 | Viewed by 1899
Abstract
The extraction of clary sage (Salvia sclarea L.) using supercritical carbon dioxide (SC-CO2) was systematically studied by using thin layer chromatography-direct bioautography (TLC-DB) and response surface methodology (RSM). The three parameters temperature, pressure, and cosolvent ratio were optimized for the [...] Read more.
The extraction of clary sage (Salvia sclarea L.) using supercritical carbon dioxide (SC-CO2) was systematically studied by using thin layer chromatography-direct bioautography (TLC-DB) and response surface methodology (RSM). The three parameters temperature, pressure, and cosolvent ratio were optimized for the maximum antibacterial activity of clary sage extracts against Pseudomonas aeruginosa (P. aeruginosa) and methicillin-resistant Staphylococcus aureus (MRSA). The highest inhibition zone was 7.51 mm for P. aeruginosa and 7.57 mm for MRSA. According to RSM analysis, the predicted optimum extraction parameters are 18.6 MPa pressure, 40 °C temperature, and 2% ethanol (EtOH) ratio. The combination of this analytical and statistical method allows saving time, money, and instrument runtime in the optimization of essential oil composition, which is tailored to a specific task and could be useful on any kind of herbs in a wide range of use from perfume manufacturing to the food industry. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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13 pages, 880 KiB  
Article
Nematicidal Activity of Essential Oil from Lavandin (Lavandula × intermedia Emeric ex Loisel.) as Related to Chemical Profile
by Trifone D’Addabbo, Sebastiano Laquale, Maria Pia Argentieri, Maria Grazia Bellardi and Pinarosa Avato
Molecules 2021, 26(21), 6448; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216448 - 26 Oct 2021
Cited by 7 | Viewed by 1897
Abstract
Essential oils (EOs) from lavandin are known for a large spectrum of biological properties but poorly and contrastingly documented for their activity against phytoparasitic nematodes. This study investigated the toxicity of EOs from three different lavandin cultivars, Abrialis, Rinaldi Cerioni, and Sumiens, either [...] Read more.
Essential oils (EOs) from lavandin are known for a large spectrum of biological properties but poorly and contrastingly documented for their activity against phytoparasitic nematodes. This study investigated the toxicity of EOs from three different lavandin cultivars, Abrialis, Rinaldi Cerioni, and Sumiens, either to juveniles (J2) and eggs of the root-knot nematode Meloidogyne incognita and to infective stages of the lesion nematode Pratylenchus vulnus. The suppressive activity of treatments with EOs from the three lavandin cultivars in soil infested by M. incognita was also investigated in a greenhouse experiment on potted tomato. The compositional profiles of tested EOs were also analyzed by GC-FID and GC-MS. Linalool was the major component of all the three EOs, as accounting for about 66%, 48%, and 40% of total EO from cv Rinaldi Cerioni, Sumiens, and Abrialis, respectively. Linalool acetate was the second most abundant compound in the EOs from cv Abrialis (18.3%) and Sumiens (14.9%), while significant amounts of camphor (11.5%) and 1,8-cineole (12.1%) were detected in cv Rinaldi Cerioni and Sumiens EOs, respectively. The mortality of M. incognita J2 peaked 82.0%, 95.8%, and 89.8% after a 24 h treatment with 100 mg·mL−1 solutions of cv Abrialis, Rinaldi Cerioni, and Sumiens EOs, respectively. Infective specimens of P. vulnus were largely more sensitive than M. incognita J2, as there were peak mortality rates of 65.5%, 67.7%, and 75.7% after 4 h of exposure to Abrialis, Rinaldi Cerioni, and Sumiens EO, respectively. All three lavandin EOs significantly affected also M. incognita egg hatchability, which reduced to 43.6% after a 48 h egg mass exposure to a 100 µg·mL−1 solution of cv Rinaldi Cerioni EO. Soil treatments with the three lavandin EOs strongly reduced, according to a dose–effect relationship, density of M. incognita eggs, and J2 both on tomato roots and in soil, as well as significantly reduced gall formation on tomato roots. Finally, almost all soil treatments with the lavandin EOs also resulted in a positive impact on tomato plant growth. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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17 pages, 720 KiB  
Article
Biological Activity of Essential Oils of Four Juniper Species and Their Potential as Biopesticides
by Ivanka Semerdjieva, Valtcho D. Zheljazkov, Tzenka Radoukova, Ivayla Dincheva, Neshka Piperkova, Vasilina Maneva, Tess Astatkie and Miroslava Kačániová
Molecules 2021, 26(21), 6358; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26216358 - 21 Oct 2021
Cited by 17 | Viewed by 2893
Abstract
The objective of this study was to assess the biological activity of essential oils (EOs) of four Juniperus species obtained via two different distillation methods and their potential as biopesticides. The studied factors were juniper species (Juniperus communis L., J. oxycedrus L., [...] Read more.
The objective of this study was to assess the biological activity of essential oils (EOs) of four Juniperus species obtained via two different distillation methods and their potential as biopesticides. The studied factors were juniper species (Juniperus communis L., J. oxycedrus L., J. pygmaea C. Koch., and J. sibirica Burgsd), plant sex (male (M) and female (F)), and distillation method (hydrodistillation via a standard Clevenger apparatus (ClevA) and semi-commercial (SCom) steam distillation). The hypothesis was that the EO will have differential antioxidant, antimicrobial, and insecticidal activities as a function of plant species, plant sex, and distillation method. The two distillation methods resulted in similar EO composition within a given species. However, there were differences in the EO content (yield) due to the sex of the plant, and also differences in the proportions of some EO components. The concentration of α-pinene, β-caryophyllene, δ-cadinene and δ-cadinol was dissimilar between the EO of M and F plants within all four species. Additionally, M and F plants of J. pygmaea, and J. sibirica had significantly different concentrations of sabinene within the respective species. The EOs obtained via ClevA extraction showed higher antioxidant capacity within a species compared with those from SCom extraction. All of the tested EOs had significant repellent and insecticidal activity against the two aphid species Rhopalosiphum padi (bird cherry-oat aphid) and Sitobion avenae (English grain aphid) at concentrations of the EO in the solution of 1%, 2.5%, and 5%. The tested EOs demonstrated moderate activity against selected pathogens Fusarium spp., Botrytis cinerea, Colletotrichum spp., Rhizoctonia solani and Cylindrocarpon pauciseptatum. The results demonstrate that the standard ClevA would provide comparable EO content and composition in comparison with SCom steam distillation; however, even slight differences in the EO composition may translate into differential bioactivity. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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12 pages, 654 KiB  
Article
Cinnamomum cassia and Syzygium aromaticum Essential Oils Reduce the Colonization of Salmonella Typhimurium in an In Vivo Infection Model Using Caenorhabditis elegans
by Marie Lang, Aude Montjarret, Emmanuel Duteil and Gilles Bedoux
Molecules 2021, 26(18), 5598; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26185598 - 15 Sep 2021
Cited by 6 | Viewed by 1869
Abstract
The regulation of intestinal colonization in livestock by means of non-bactericidal additives is an important management lever for zoonotic bacteria such as Salmonella spp. Caenorhabditis elegans is proposed here as a model for the evaluation of five essential oils (EOs) as anti-colonization products [...] Read more.
The regulation of intestinal colonization in livestock by means of non-bactericidal additives is an important management lever for zoonotic bacteria such as Salmonella spp. Caenorhabditis elegans is proposed here as a model for the evaluation of five essential oils (EOs) as anti-colonization products against Salmonella Typhimurium. An evaluation of the toxicity of EOs for C. elegans showed LD50 values ranging from 74.5 ± 9.6 µg/mL for Cinnamomum cassia (CEO) to 271.6 ± 14.9 µg/mL for Syzygium aromaticum (SyEO). Both EOs significantly inhibited bacterial colonization in the digestive tract of C. elegans with reductions of 0.88 and 0.70 log CFU/nematode at nontoxic concentrations of 50 µg/mL and 150 µg/mL, respectively. With the minimal bactericidal concentrations of CEO and SyEO against S. Typhimurium being 312.5 µg/mL and 625 µg/mL, respectively, an antibacterial effect can be excluded to explain the inhibition of the bacterial load. The anti-colonizing activity of these two EOs could, however, be related to an inhibition of the swimming motility, which was significantly reduced by 23.47% for CEO at 50 µg/mL and 19.56% for SyEO at 150 µg/mL. This study shows the potential of C. elegans as a predictive in vivo model of anti-colonizing activities that is suitable for the evaluation of essential oils. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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17 pages, 1370 KiB  
Article
Essential Oils Extracted from Organic Propolis Residues: An Exploratory Analysis of Their Antibacterial and Antioxidant Properties and Volatile Profile
by Natália Y. Ikeda, Carmen M. S. Ambrosio, Alberto Claudio Miano, Pedro L. Rosalen, Eduardo M. Gloria and Severino M. Alencar
Molecules 2021, 26(15), 4694; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26154694 - 03 Aug 2021
Cited by 11 | Viewed by 2333
Abstract
The industrial processing of crude propolis generates residues. Essential oils (EOs) from propolis residues could be a potential source of natural bioactive compounds to replace antibiotics and synthetic antioxidants in pig production. In this study, we determined the antibacterial/antioxidant activity of EOs from [...] Read more.
The industrial processing of crude propolis generates residues. Essential oils (EOs) from propolis residues could be a potential source of natural bioactive compounds to replace antibiotics and synthetic antioxidants in pig production. In this study, we determined the antibacterial/antioxidant activity of EOs from crude organic propolis (EOP) and from propolis residues, moist residue (EOMR), and dried residue (EODR), and further elucidated their chemical composition. The EOs were extracted by hydrodistillation, and their volatile profile was tentatively identified by GC-MS. All EOs had an antibacterial effect on Escherichia coli and Lactobacillus plantarum as they caused disturbances on the growth kinetics of both bacteria. However, EODR had more selective antibacterial activity, as it caused a higher reduction in the maximal culture density (D) of E. coli (86.7%) than L. plantarum (46.9%). EODR exhibited mild antioxidant activity, whereas EOMR showed the highest antioxidant activity (ABTS = 0.90 μmol TE/mg, FRAP = 463.97 μmol Fe2+/mg) and phenolic content (58.41 mg GAE/g). Each EO had a different chemical composition, but α-pinene and β-pinene were the major compounds detected in the samples. Interestingly, specific minor compounds were detected in a higher relative amount in EOMR and EODR as compared to EOP. Therefore, these minor compounds are most likely responsible for the biological properties of EODR and EOMR. Collectively, our findings suggest that the EOs from propolis residues could be resourcefully used as natural antibacterial/antioxidant additives in pig production. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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11 pages, 311 KiB  
Article
Chemical Constituents of the Essential Oil from Ecuadorian Endemic Species Croton ferrugineus and Its Antimicrobial, Antioxidant and α-Glucosidase Inhibitory Activity
by Eduardo Valarezo, Génesis Gaona-Granda, Vladimir Morocho, Luis Cartuche, James Calva and Miguel Angel Meneses
Molecules 2021, 26(15), 4608; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26154608 - 29 Jul 2021
Cited by 11 | Viewed by 2223
Abstract
Croton ferrugineus Kunth is an endemic species of Ecuador used in traditional medicine both for wound healing and as an antiseptic. In this study, fresh Croton ferrugineus leaves were collected and subjected to hydrodistillation for extraction of the essential oil. The chemical composition [...] Read more.
Croton ferrugineus Kunth is an endemic species of Ecuador used in traditional medicine both for wound healing and as an antiseptic. In this study, fresh Croton ferrugineus leaves were collected and subjected to hydrodistillation for extraction of the essential oil. The chemical composition of the essential oil was determined by gas chromatography equipped with a flame ionization detector and gas chromatography coupled to a mass spectrometer using a non-polar and a polar chromatographic column. The antibacterial activity was assayed against three Gram-positive bacteria, one Gram-negative bacterium and one dermatophyte fungus. The radical scavenging properties of the essential oil was evaluated by means of DPPH and ABTS assays. The chemical analysis allowed us to identify thirty-five compounds representing more than 99.95% of the total composition. Aliphatic sesquiterpene hydrocarbon trans-caryophyllene was the main constituent with 20.47 ± 1.25%. Other main compounds were myrcene (11.47 ± 1.56%), β-phellandrene (10.55 ± 0.02%), germacrene D (7.60 ± 0.60%), and α-humulene (5.49 ± 0.38%). The essential oil from Croton ferrugineus presented moderate activity against Candida albicans (ATCC 10231) with an MIC of 1000 μg/mL, a scavenging capacity SC50 of 901 ± 20 µg/mL with the ABTS method, and very strong antiglucosidase activity with an IC50 of 146 ± 20 µg/mL. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
25 pages, 12497 KiB  
Article
Essential Oil Composition and Bioactivity of Two Juniper Species from Bulgaria and Slovakia
by Valtcho D. Zheljazkov, Charles L. Cantrell, Ivanka Semerdjieva, Tzenka Radoukova, Albena Stoyanova, Vasilina Maneva, Miroslava Kačániová, Tess Astatkie, Daniela Borisova, Ivayla Dincheva and Ivan Salamon
Molecules 2021, 26(12), 3659; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26123659 - 15 Jun 2021
Cited by 17 | Viewed by 3015
Abstract
Juniperus excelsa M. Bieb and J. sabina L. contain essential oil (EO), while J. sabina also contains podophyllotoxin, which is used as a precursor for anti-cancer drugs. Two studies were conducted. The first assessed the variability in the EO profile and podophyllotoxin concentration [...] Read more.
Juniperus excelsa M. Bieb and J. sabina L. contain essential oil (EO), while J. sabina also contains podophyllotoxin, which is used as a precursor for anti-cancer drugs. Two studies were conducted. The first assessed the variability in the EO profile and podophyllotoxin concentration of the two junipers, depending on the location and tree gender. The main EO constituents of J. excelsa were α-cedrol, α-limonene and α-pinene, while the constituents in J. sabina were sabinene, terpinen-4-ol, myrtenyl acetate and α-cadinol. The podophyllotoxin yield of 18 J. sabina accessions was 0.07–0.32% (w/w), but this was not found in any of the J. excelsa accessions. The second study assessed the effect of hydrodistillation (Clevenger apparatus) and steam distillation (in a semi-commercial apparatus) on the EO profile and bioactivity. The extraction type did not significantly alter the EO composition. The EO profiles of the two junipers and their accessions were different and may be of interest to the industry utilizing juniper leaf EO. Breeding and selection programs could be developed with the two junipers (protected species) in order to identify chemotypes with (1) a high EO content and desirable composition, and (2) a high concentration of podophyllotoxin in J. sabina. Such chemotypes could be established as agricultural crops for the commercial production of podophyllotoxin and EO. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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Review

Jump to: Research

19 pages, 18782 KiB  
Review
Antidiabetic Potential of Volatile Cinnamon Oil: A Review and Exploration of Mechanisms Using In Silico Molecular Docking Simulations
by Nicole Stevens and Kathryn Allred
Molecules 2022, 27(3), 853; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030853 - 27 Jan 2022
Cited by 19 | Viewed by 5340
Abstract
Cinnamon has been used as a flavoring and medicinal agent for centuries. Much research has focused on cinnamon bark powder, which contains antioxidants, flavonoids, carotenoids, vitamins, minerals, fiber, and small amounts of essential oil. However, isolated and concentrated cinnamon essential oil may also [...] Read more.
Cinnamon has been used as a flavoring and medicinal agent for centuries. Much research has focused on cinnamon bark powder, which contains antioxidants, flavonoids, carotenoids, vitamins, minerals, fiber, and small amounts of essential oil. However, isolated and concentrated cinnamon essential oil may also have important medicinal qualities, particularly in antidiabetic therapy. Some of the most common essential oil constituents identified in the literature include cinnamaldehyde, eugenol, and beta-caryophyllene. Due to their high concentration in cinnamon essential oil, these constituents are hypothesized to have the most significant physiological activity. Here, we present a brief review of literature on cinnamon oil and its constituents as they relate to glucose metabolism and diabetic pathogenesis. We also present molecular docking simulations of these cinnamon essential oil constituents (cinnamaldehyde, eugenol, beta-caryophyllene) that suggest interaction with several key enzymes in glucometabolic pathways. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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