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Chemistry of Essential Oils: The Incredible Wealth of Plants

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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 2023) | Viewed by 15453

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Prof. Dr. Xavier Fernandez

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CNRS, Institut de Chimie de Nice UMR 7272, Université Côte d'Azur, Nice, France
Interests: natural products chemistry; analytical sciences; flavor and fragrances chemistry; essential oils; cosmetics; archeochemistry

Special Issue Information

Dear Colleagues,

Known for millennia, essential oils are still the subject of numerous studies. These extracts obtained by hydrodistillation, steam distillation, dry distillation and expression from plants are very complex mixtures of metabolites. With the development of green chemistry and the resurgence of consumer interest in natural products, essential oils are of increasing interest to the scientific community.

The present Special Issue, “Chemistry of essential oils: the incredible wealth of plants”, aims to collect and publish recent advances in this interdisciplinary area. Reviews and research articles dealing with innovative extraction and analytical techniques, ecoextraction, original procedures, essential oils composition and biology are encouraged, as well as valorization in various areas such as perfume, aroma, cosmetics, human and animal drugs, and biocontrol. In terms of dissemination, this Special Issue is aiming to provide some guidelines for good practice and reporting in several areas: analytical chemistry, natural product chemistry, food processing, pharmaceutical chemistry, agricultural products, functional foods, nutraceuticals, cosmetics, bioeconomy, etc.

Prof. Dr. Xavier Fernandez
Guest Editor

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Keywords

Essential oils
Natural products
Biosynthesis
Extraction
Ecoextraction
Chemical analysis
Microwave
Biological activities
Secondary metabolites
Flavors and fragrances
Cosmetics
Neutraceutics
Biocontrol
Human and animal drugs
Hemi-synthesis
Valorization
Industrial by-products
Life cycle assessment

Published Papers (7 papers)

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Research

20 pages, 4404 KiB

Open AccessArticle

Herb and Flowers of Achillea millefolium subsp. millefolium L.: Structure and Histochemistry of Secretory Tissues and Phytochemistry of Essential Oils

by Agata Konarska, Elżbieta Weryszko-Chmielewska, Aneta Sulborska-Różycka, Anna Kiełtyka-Dadasiewicz, Marta Dmitruk and Małgorzata Gorzel

Molecules 2023, 28(23), 7791; https://doi.org/10.3390/molecules28237791 - 27 Nov 2023

Viewed by 1023

Abstract

Achillea millefolium L. herb and flowers have high biological activity; hence, they are used in medicine and cosmetics. The aim of this study was to perform morpho-anatomical analyses of the raw material, including secretory tissues, histochemical assays of the location of lipophilic compounds, and quantitative and qualitative analysis of essential oil (EO). Light and scanning electron microscopy techniques were used to analyse plant structures. The qualitative analyses of EO were carried out using gas chromatography-mass spectrometry (GC/MS). The results of this study showed the presence of exogenous secretory structures in the raw material, i.e., conical cells (papillae) on the adaxial surface of petal teeth and biseriate glandular trichomes on the surface flowers, bracts, stems, and leaves. Canal-shaped endogenous secretory tissue was observed in the stems and leaves. The histochemical assays revealed the presence of total, acidic, and neutral lipids as well as EO in the glandular trichome cells. Additionally, papillae located at the petal teeth contained neutral lipids. Sesquiterpenes were detected in the glandular trichomes and petal epidermis cells. The secretory canals in the stems were found to contain total and neutral lipids. The phytochemical assays demonstrated that the A. millefolium subsp. millefolium flowers contained over 2.5-fold higher amounts of EO (6.1 mL/kg) than the herb (2.4 mL/kg). The EO extracted from the flowers and herb had a similar dominant compounds: β-pinene, bornyl acetate, (E)-nerolidol, 1,8-cineole, borneol, sabinene, camphor, and α-pinene. Both EO samples had greater amounts of monoterpenes than sesquiterpenes. Higher amounts of oxygenated monoterpenes and oxygenated sesquiterpenoids were detected in the EO from the herb than from the flowers. Full article

(This article belongs to the Special Issue Chemistry of Essential Oils: The Incredible Wealth of Plants)

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13 pages, 2024 KiB

Open AccessArticle

Chemical Investigations in Kelussia odoratissima Mozaff. Leaves Based on Comprehensive Analytical Methods: LC-MS, SPME, and GC-MS Analyses

by Mehdi Rahimmalek, Antoni Szumny, Shima Gharibi, Natalia Pachura, Mehran Miroliaei and Jacek Łyczko

Molecules 2023, 28(16), 6140; https://doi.org/10.3390/molecules28166140 - 19 Aug 2023

Cited by 2 | Viewed by 946

Abstract

Kelussia odoratissima Mozaff. is a species of Apiaceae endemic to the Zagros Mountains in Iran. In the present investigation, for the first time, the polyphenolic compounds and flavonoids of its leaves were determined by liquid chromatography-mass spectrometry (LC-MS). As a result, p-coumaric acid, ferulic acid, caffeic acid, chlorogenic acid, acetyl phloroglucinol, vanillic acid, m-coumaric acid, and 4-methylsiringol were determined as the main phenolic compounds, while 3-hydroxyflavone, flavone, quercetin, rutin, neohesperidin, polydatin, and diosmin were the main flavonoid components, of which chlorogenic acid (303.08 µL/gDW), neohesperidin (38.37 µL/gDw), and diosmin (28.62 µL/gDW) were the most abundant. Solid-phase microextraction (SPME) was also used to determine the chemical compounds. Based on SPME, (Z)-undec-6-en-2-one (17.48%) and (Z)-butylidenephthalide (4.348%) were the major components. Based on GC-MS analyses, (Z)-ligustilide was the main compound; however, some new compounds were also determined, including 3-ethylisobenzofuran-1 (3H)-one, (E)-ligugustilide, and E-n-butylidene phthalide. Also, for the first time, we have identified EOs ethyl and isobutyl phthalides on the basis of the obtained EI-MS spectra. Finally, the fragmentation of phthalides is also discussed in this research. Full article

(This article belongs to the Special Issue Chemistry of Essential Oils: The Incredible Wealth of Plants)

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12 pages, 1134 KiB

Open AccessArticle

Matricaria chamomilla Essential Oils: Repellency and Toxicity against Imported Fire Ants (Hymenoptera: Formicidae)

by Farhan Mahmood Shah, Dileep Kumar Guddeti, Pradeep Paudel, Jian Chen, Xing-Cong Li, Ikhlas A. Khan and Abbas Ali

Molecules 2023, 28(14), 5584; https://doi.org/10.3390/molecules28145584 - 22 Jul 2023

Cited by 2 | Viewed by 1262

Abstract

Matricaria chamomilla flower essential oils (EOs) blue Egyptian (EO-1), chamomile German CO2 (EO-2), and chamomile German (EO-3) and the pure compound α-bisabolol were evaluated against red imported fire ants (RIFA), Solenopsis invicta Buren, black imported fire ants, S. richteri Forel (BIFA), and hybrid imported fire ants (HIFA) for their repellency and toxicity. A series of serial dilutions were tested starting from 125 µg/g until the failure of the treatment. Based on the amount of sand removed, EO-1 showed significant repellency at dosages of 7.8, 7.8, and 31.25 µg/g against RIFA, BIFA, and HIFA, respectively. EO-3 was repellent at 3.9, 7.8, and 31.25 µg/g against BIFA, RIFA, and HIFA, whereas α-bisabolol was active at 7.8, 7.8, and 31.25 µg/g against BIFA, HIFA, and RIFA, respectively. DEET (N, N-diethyl-meta-toluamide) was active at 31.25 µg/g. Toxicity of EOs and α-bisabolol was mild to moderate. For EO-1, LC₅₀ values were 93.6 and 188.11 µg/g against RIFA and BIFA; 98.11 and 138.4 µg/g for EO-2; and 142.92 and 202.49 µg/g for EO-3, respectively. The LC₅₀ of α-bisabolol was 159.23 µg/g against RIFA. In conclusion, M. chamomilla EOs and α-bisabolol offer great potential to be developed as imported fire ant repellents. Full article

(This article belongs to the Special Issue Chemistry of Essential Oils: The Incredible Wealth of Plants)

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17 pages, 798 KiB

Open AccessArticle

Commiphora wildii Merxm. Essential Oil: Natural Heptane Source and Co-Product Valorization

by Djallel Mansouri, Anne Landreau, Thomas Michel, Clément De Saint Jores, Bienvenue Razafimandimby, Marie Kempf, Stéphane Azoulay, Nicolas Papaiconomou and Xavier Fernandez

Molecules 2023, 28(2), 891; https://doi.org/10.3390/molecules28020891 - 16 Jan 2023

Viewed by 1941

Abstract

As an alternative to fossil volatile hydrocarbon solvents used nowadays in perfumery, investigation on essential oil of Commiphora wildii Merxm. oleo gum resin as a source of heptane is reported here. Heptane, representing up to 30 wt-% of this oleo gum resin, was successfully isolated from the C. wildii essential oil, using an innovative double distillation process. Isolated heptane was then used as a solvent in order to extract some noble plants of perfumery. It was found that extracts obtained with this solvent were more promising in terms of sensory analysis than those obtained from fossil-based heptane. In addition, in order to valorize the essential oil depleted from heptane, chemical composition of this oil was found to obtain, and potential biological activity properties were studied. A total of 172 different compounds were identified by GC-MS in the remaining oil. In vitro tests—including hyaluronidase, tyrosinase, antioxidant, elastase and lipoxygenase, as well as inhibitory tests against two yeasts and 21 bacterial strains commonly found on the skin—were carried out. Overall, bioassays results suggest this heptane-depleted essential oil is a promising active ingredient for cosmetic applications. Full article

(This article belongs to the Special Issue Chemistry of Essential Oils: The Incredible Wealth of Plants)

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14 pages, 4160 KiB

Open AccessArticle

Essential Oils from Bolivia. XV. Herzogole, an Original Monoterpene Benzodioxole from an Essential Oil from Pentacalia herzogii (Cabrera) Cuatrec

by Alexis St-Gelais, Eliana M. Maldonado, Gloria Saavedra, Samuel Siles-Alvarado, Jérôme Alsarraf, Guy Collin and André Pichette

Molecules 2021, 26(19), 5766; https://doi.org/10.3390/molecules26195766 - 23 Sep 2021

Cited by 2 | Viewed by 1926

Abstract

Over 15 years, with the support of a Canadian funding agency, the Universidad Mayor de San Simón, in Bolivia, undertook a large survey of aromatic plants of the South American country. More than a hundred species were studied under various aspects, including the production and characterization of essential oils. As part of this survey, the chemical composition of an essential oil sample obtained from Pentacalia herzogii (Asteraceae) growing wild in the High Valley region of the department of Cochabamba was determined by a combination of GC and GC-MS measurements. α-Pinene was the main constituent of this essential oil (34%), accompanied by limonene (22%) and germacrene D (7.5%) as well as an important fraction of methoxylated monoterpenoids. They were mainly isomers of thymol methyl ether, accounting for 13% of the chromatogram. A new quantitatively important compound (9%) was identified through NMR and chemical synthesis as 4-isopropyl-6-methylbenzo[d][1,3]dioxole, and designated herzogole, alongside the minor related compound 1-isopropyl-2,3-dimethoxy-5-methylbenzene. The monoterpene benzodioxole featured a distinctive green-phenolic aroma which could raise interest for fragrance use. Since these compounds were not known naturally, a biosynthetic mechanism of their formation was proposed and put in perspective to illustrate the metabolic originality of P. herzogii. Full article

(This article belongs to the Special Issue Chemistry of Essential Oils: The Incredible Wealth of Plants)

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10 pages, 255 KiB

Open AccessArticle

The Chemical Profiling of Essential Oils from Different Tissues of Cinnamomum camphora L. and Their Antimicrobial Activities

by Darbin Kumar Poudel, Anil Rokaya, Pawan Kumar Ojha, Sujan Timsina, Rakesh Satyal, Noura S. Dosoky, Prabodh Satyal and William N. Setzer

Molecules 2021, 26(17), 5132; https://doi.org/10.3390/molecules26175132 - 24 Aug 2021

Cited by 29 | Viewed by 4118

Abstract

Cinnamomum camphora L. is grown as an ornamental plant, used as raw material for furniture, as a source of camphor, and its essential oil can be used as an important source for perfume as well as alternative medicine. A comparative investigation of essential oil compositions and antimicrobial activities of different tissues of C. camphora was carried out. The essential oils were extracted by hydrodistillation with a Clevenger apparatus and their compositions were evaluated through gas chromatography-mass spectrometry (GC-MS), enantiomeric composition by chiral GC-MS, and antimicrobial properties were assayed by measuring minimum inhibitory concentrations (MICs). Different plant tissues had different extraction yields, with the leaf having the highest yield. GC-MS analysis revealed the presence of 18, 75, 87, 67, 67, and 74 compounds in leaf, branch, wood, root, leaf/branch, and leaf/branch/wood, respectively. The significance of combining tissues is to enable extraction of commercial quality essential oils without the need to separate them. The oxygenated monoterpene camphor was the major component in all tissues of C. camphora except for safrole in the root. With chiral GC-MS, the enantiomeric distributions of 12, 12, 13, 14, and 14 chiral compounds in branch, wood, root, leaf/branch, and leaf/branch/wood, respectively, were determined. The variation in composition and enantiomeric distribution in the different tissues of C. camphora may be attributed to the different defense requirements of these tissues. The wood essential oil showed effective antibacterial activity against Serratia marcescens with an MIC of 39.1 μg/mL. Similarly, the mixture of leaf/branch/wood essential oils displayed good antifungal activity against Aspergillus niger and Aspergillus fumigatus while the leaf essential oil was notably active against Trichophyton rubrum. C. camphora essential oils showed variable antimicrobial activities against dermal and pulmonary-borne microbes. Full article

(This article belongs to the Special Issue Chemistry of Essential Oils: The Incredible Wealth of Plants)

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10 pages, 295 KiB

Open AccessArticle

The Biological Activity of Monarda didyma L. Essential Oil and Its Effect as a Diet Supplement in Mice and Broiler Chicken

by Héloïse Côté, André Pichette, Alexis St-Gelais and Jean Legault

Molecules 2021, 26(11), 3368; https://doi.org/10.3390/molecules26113368 - 02 Jun 2021

Cited by 8 | Viewed by 2523

Abstract

The use of growth-promoting antibiotics in livestock faces increasing scrutiny and opposition due to concerns about the increased occurrence of antibiotic-resistant bacteria. Alternative solutions are being sought, and plants of Lamiaceae may provide an alternative to synthetic antibiotics in animal nutrition. In this study, we extracted essential oil from Monarda didyma, a member of the Lamiaceae family. We examined the chemical composition of the essential oil and then evaluated the antibacterial, antioxidant, and anti-inflammatory activities of M. didyma essential oil and its main compounds in vitro. We then evaluated the effectiveness of M. didyma essential oil in regard to growth performance, feed efficiency, and mortality in both mice and broilers. Carvacrol (49.03%) was the dominant compound in the essential oil extracts. M. didyma essential oil demonstrated antibacterial properties against Escherichia coli (MIC = 87 µg·mL⁻¹), Staphylococcus aureus (MIC = 47 µg·mL⁻¹), and Clostridium perfringens (MIC = 35 µg·mL⁻¹). Supplementing the diet of mice with essential oil at a concentration of 0.1% significantly increased body weight (+5.4%) and feed efficiency (+18.85%). In broilers, M. didyma essential oil significantly improved body weight gain (2.64%). Our results suggest that adding M. didyma essential oil to the diet of broilers offers a potential substitute for antibiotic growth promoters. Full article

(This article belongs to the Special Issue Chemistry of Essential Oils: The Incredible Wealth of Plants)

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