Chemistry of Essential Oils and Food Flavours

A special issue of Foods (ISSN 2304-8158). This special issue belongs to the section "Food Physics and (Bio)Chemistry".

Deadline for manuscript submissions: closed (31 May 2021) | Viewed by 28909

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Special Issue Editors


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Guest Editor
1. Adjunct Professor, Southern Cross University Plant Science, Lismore, NSW, Australia
2. Editorial Board, Journal of Essential Oil Research
3. Chairman, Standards Australia, CH21 Essential Oil Committee
Interests: essential oils; plant chemistry; organic chemistry; structural elucidation; chemical ecology; bioactivity; essential oil authentication

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Guest Editor
1. Department of Chemical Engineering and Analytical Chemistry, Faculty of Chemistry, University of Barcelona, Martí i Franquès 1-11, E-08028 Barcelona, Spain
2. Research Institute in Food Nutrition and Food Safety, Universitat de Barcelona, Av. Prat de la Riba 171, Edifici Recerca (Gaudí), E-08921 Santa Coloma de Gramenet, Spain
Interests: food authentication; food characterization; food classification; food fraud identification; secondary metabolites; polyphenols; foodomics; bioactive compounds; liquid chromatography; mass spectrometry; high resolution mass spectrometry; ambient mass spectrometry; capillary electrophoresis; chemometrics
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Special Issue Information

Dear Colleagues,

Essential oils have important functions in nature. In addition, they are used commercially as in such areas as flavours, fragrances and health-care products. Their properties present a challenge with respect to investigating their chemical structure, function, bioactivity, analysis and commercialization as value-added products. Analytical techniques for the investigation of essential oil chemistry are forever changing. The sophistication, adulteration or imitation of natural products is becoming difficult to detect as the perpetrators also use modern techniques. Consequently, an understanding of the chemistry of essential oils that keeps abreast with the latest in instrumental and computational developments is paramount.

Thus, the objective of this Special Issue is to broadcast the latest advances in essential oil discoveries with respect oil chemistry, methodology, instrumentation, bioactivity, chemical ecology, biosynthesis and authentication especially in relation to foods.

Dr. Ian Southwell
Prof. Dr. Oscar Núñez
Guest Editors

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Keywords

  • Essential oils
  • Instrumentation
  • Structure elucidation
  • Bioactivity
  • Flavour
  • Authentication
  • Biosynthesis
  • Chemical Ecology

Published Papers (8 papers)

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Editorial

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3 pages, 204 KiB  
Editorial
Editorial for the Special Issue, “Chemistry of Essential Oils and Food Flavours”
by Ian Southwell and Oscar Núñez
Foods 2022, 11(15), 2182; https://doi.org/10.3390/foods11152182 - 22 Jul 2022
Viewed by 1222
Abstract
Essential oils have important functions in nature [...] Full article
(This article belongs to the Special Issue Chemistry of Essential Oils and Food Flavours)

Research

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15 pages, 1315 KiB  
Article
Headspace/GC–MS Analysis and Investigation of Antibacterial, Antioxidant and Cytotoxic Activity of Essential Oils and Hydrolates from Rosmarinus officinalis L. and Lavandula angustifolia Miller
by Stefania Garzoli, Valentina Laghezza Masci, Sara Franceschi, Antonio Tiezzi, Pierluigi Giacomello and Elisa Ovidi
Foods 2021, 10(8), 1768; https://doi.org/10.3390/foods10081768 - 30 Jul 2021
Cited by 31 | Viewed by 4024
Abstract
In this work, essential oils (EOs) and hydrolates (Hys) of Rosmarinus officinalis L. and Lavandula angustifolia Mill., grown in Tuscany (Italy), were studied to describe their chemical composition and biological activities. The aromatic profile of the EOs liquid phase was carried out by [...] Read more.
In this work, essential oils (EOs) and hydrolates (Hys) of Rosmarinus officinalis L. and Lavandula angustifolia Mill., grown in Tuscany (Italy), were studied to describe their chemical composition and biological activities. The aromatic profile of the EOs liquid phase was carried out by gas chromatography–mass spectrometry (GC–MS), while the volatile composition of vapor phase EOs and Hys was performed by headspace (HS)/GC–MS. The obtained results show that monoterpene hydrocarbons (71.5% and 89.5%) were the main compounds, followed by oxygenated monoterpenes (26.0% and 10.5%) in the liquid and vapor phase of R. officinalis EO, respectively. The oxygenated monoterpenes were the main components of L. angustifolia EO, reaching 86.9% in the liquid phase and 53.7% in the vapor phase. Regarding Hys, they consisted only of oxygenated monoterpenes, and 1,8-cineole (56.2%) and linalool (42.9%), were the main components of R. officinalis and L. officinalis Hys, respectively. Their cytotoxicity was investigated on an SHSY5Y neuroblastoma cell line by thiazolyl blue tetrazolium bromide (MTT) test, showing a notable effect of the EOs with a time-independent manner of activity and half maximal effective concentration (EC50) values quite similar for the two plant species (from 0.05% to 0.06% v/v for the three time points evaluated). A measurable activity of Hys was also obtained although with higher EC50 values. The antibacterial activity against Escherichia coli ATCC® 25922, Pseudomonas fluorescens ATCC® 13525, Acinetobacter bohemicus DSM 102855 as Gram-negative bacteria and Kocuria marina DSM 16420, Bacillus cereus ATCC® 10876 as Gram-positive bacteria, was evaluated by the agar disk-diffusion method and the VPT (vapor phase test) to determinate the MIC (minimal inhibitory concentration) and the MBC (minimal bactericidal concentration) values. Both EOs possessed a high activity against all the bacterial strains with MIC values ranging from 0.19% to 3.13% v/v. Unlike EOs, Hys did not show an inhibition of the bacterial growth at the tested concentrations. Furthermore, antioxidant power was measured by 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt-based (ABTS•+) and the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays, showing a remarkable ability to reduce radicals by both EOs; Hys were slightly less active. The findings highlighted that R. officinalis and L. angustifolia EOs and Hys have a chemical composition rich in bioactive molecules, which can exert different biological activities. Full article
(This article belongs to the Special Issue Chemistry of Essential Oils and Food Flavours)
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16 pages, 2756 KiB  
Article
Dietary Intake of Coumarins and Furocoumarins through Citrus Beverages: A Detailed Estimation by a HPLC-MS/MS Method Combined with the Linear Retention Index System
by Adriana Arigò, Francesca Rigano, Marina Russo, Emanuela Trovato, Paola Dugo and Luigi Mondello
Foods 2021, 10(7), 1533; https://doi.org/10.3390/foods10071533 - 02 Jul 2021
Cited by 14 | Viewed by 3540
Abstract
Official regulations concerning the maximum number of substances in food are introduced as a consequence of possible adverse effects, after oral administration. In this regard, analytical methods are necessary in order to determine specific targets. Among oxygen heterocyclic compounds (OHCs, that are furocoumarins, [...] Read more.
Official regulations concerning the maximum number of substances in food are introduced as a consequence of possible adverse effects, after oral administration. In this regard, analytical methods are necessary in order to determine specific targets. Among oxygen heterocyclic compounds (OHCs, that are furocoumarins, coumarins and polymethoxyflavones), only coumarin is subject to restriction by the Regulation (EC) No 1334/2008 of the European Parliament. Furocoumarins are known for their phototoxicity and other side effects due to their dietary intake; however, an official limit about the maximum content of these compounds in food is still missing. The lack of information about the real amount of these compounds in food is responsible for the conflicting opinions about the introduction of an official limit. The HPLC-MS/MS method here proposed, in combination with the linear retention index system, represents an innovative analytical strategy for the characterization of OHCs in citrus beverages. Several types of drinks were analysed in order to quantify 35 OHCs in total. This method is suitable for the quality control of OHCs in food and the obtained results may be considered as informative data useful for the regulatory authorities in the emission of new opinions and for a potential new regulation in this field. Full article
(This article belongs to the Special Issue Chemistry of Essential Oils and Food Flavours)
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15 pages, 1192 KiB  
Article
Yeast Particle Encapsulation of Scaffolded Terpene Compounds for Controlled Terpene Release
by Ernesto R. Soto, Florentina Rus, Hanchen Li, Carli Garceau, Jeffrey Chicca, Mostafa Elfawal, David Gazzola, Martin K. Nielsen, Joseph F. Urban, Jr., Raffi V. Aroian and Gary R. Ostroff
Foods 2021, 10(6), 1207; https://doi.org/10.3390/foods10061207 - 27 May 2021
Cited by 6 | Viewed by 3167
Abstract
Terpenes are naturally occurring compounds produced by plants that are of great commercial interest in the food, agricultural, cosmetic, and pharmaceutical industries due to their broad spectra of antibacterial, antifungal, anthelmintic, membrane permeation enhancement, and antioxidant biological activities. Applications of terpenes are often [...] Read more.
Terpenes are naturally occurring compounds produced by plants that are of great commercial interest in the food, agricultural, cosmetic, and pharmaceutical industries due to their broad spectra of antibacterial, antifungal, anthelmintic, membrane permeation enhancement, and antioxidant biological activities. Applications of terpenes are often limited by their volatility and the need for surfactants or alcohols to produce stable, soluble (non-precipitated) products. Yeast particles (YPs) are hollow, porous microspheres that have been used for the encapsulation of terpenes (YP terpenes) by passive diffusion of terpenes through the porous YP cell walls. We here report the development of a second generation YP encapsulated terpene technology that incorporates the stimuli-responsive control of terpene release using biodegradable pro-terpene compounds (YP pro-terpenes). YP terpenes and YP pro-terpenes were both produced, in which high levels of carvacrol, eugenol, thymol and geraniol were encapsulated. The YP pro-terpenes show higher encapsulation stability than YP terpenes due to pro-terpenes being non-volatile solids at room temperature and stable in suspensions at neutral pH. YP pro-terpenes and YP terpenes were evaluated for biological activity in antibacterial, antifungal and anthelmintic assays. The YP pro-terpenes retained the full biological activity of the parent terpene compound. Full article
(This article belongs to the Special Issue Chemistry of Essential Oils and Food Flavours)
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16 pages, 1636 KiB  
Article
Biological Properties of a Citral-Enriched Fraction of Citrus limon Essential Oil
by Marzia Pucci, Stefania Raimondo, Chiara Zichittella, Vincenza Tinnirello, Valeria Corleone, Gioacchino Aiello, Marta Moschetti, Alice Conigliaro, Simona Fontana and Riccardo Alessandro
Foods 2020, 9(9), 1290; https://doi.org/10.3390/foods9091290 - 14 Sep 2020
Cited by 18 | Viewed by 3036
Abstract
Lemon essential oil (LEO) is a well-known flavoring agent with versatile biological activities. In the present study, we have isolated and characterized four citral-enriched fractions of winter LEO. We reported that in murine and human macrophages the pre-treatment with a mix of these [...] Read more.
Lemon essential oil (LEO) is a well-known flavoring agent with versatile biological activities. In the present study, we have isolated and characterized four citral-enriched fractions of winter LEO. We reported that in murine and human macrophages the pre-treatment with a mix of these fractions (Cfr-LEO) reduces the expression of the pro-inflammatory cytokines TNF-α, IL-1β, and IL-6 induced by LPS. In addition, Cfr-LEO counteracts LPS-induced oxidative stress, as shown by the increase in the GSH/GSSG ratio in comparison to cells treated with LPS alone. Overall, the results reported here encourage the application of EO fractions, enriched in citral, in the nutraceutical industry, not only for its organoleptic properties but also for its protective action against inflammation and oxidative stress. Full article
(This article belongs to the Special Issue Chemistry of Essential Oils and Food Flavours)
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10 pages, 10934 KiB  
Article
An Absorption and Plasma Kinetics Study of Monoterpenes Present in Mastiha Oil in Humans
by Efstathia Papada, Aristea Gioxari, Charalampia Amerikanou, Nikolaos Galanis and Andriana C. Kaliora
Foods 2020, 9(8), 1019; https://doi.org/10.3390/foods9081019 - 30 Jul 2020
Cited by 11 | Viewed by 2398
Abstract
Monoterpenes are bioactive compounds, however studies on their metabolic fate in humans are scarce. The present work aimed to identify and quantify the bioactive monoterpenes myrcene, α- and β-pinene of the Mediterranean product Mastiha Oil, in human plasma after acute consumption of a [...] Read more.
Monoterpenes are bioactive compounds, however studies on their metabolic fate in humans are scarce. The present work aimed to identify and quantify the bioactive monoterpenes myrcene, α- and β-pinene of the Mediterranean product Mastiha Oil, in human plasma after acute consumption of a single dose. This was an open-label, single-arm acute study. After overnight fasting, healthy males were administered with Mastiha Oil. Blood samples were collected on different time-points before and after consumption. A novel GC-MS-MS application was performed to detect and quantify terpenes in MO and in plasma. Serum lipid resistance to oxidation was also determined. Alpha-Pinene, β-pinene and myrcene were identified and quantified in plasma. Alpha-pinene concentration significantly increased after 0.5 h of Mastiha Oil consumption, remaining significantly increased at 1 h, 2 h, 4 h, 6 h and 24 h. Beta-pinene and myrcene followed similar patterns. The increase in serum lipid resistance to oxidation was significant at 1 h, reached its peak at 2 h and remained significant until 4 h. Conclusively, α-pinene, β-pinene and myrcene that are present in Mastiha Oil are absorbed by humans. (ClinicalTrials.gov Identifier: NCT04290312). Full article
(This article belongs to the Special Issue Chemistry of Essential Oils and Food Flavours)
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Review

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19 pages, 2242 KiB  
Review
Synergistic Field Crop Pest Management Properties of Plant-Derived Essential Oils in Combination with Synthetic Pesticides and Bioactive Molecules: A Review
by Mackingsley Kushan Dassanayake, Chien Hwa Chong, Teng-Jin Khoo, Adam Figiel, Antoni Szumny and Chee Ming Choo
Foods 2021, 10(9), 2016; https://doi.org/10.3390/foods10092016 - 27 Aug 2021
Cited by 24 | Viewed by 4645
Abstract
The management of insect pests and fungal diseases that cause damage to crops has become challenging due to the rise of pesticide and fungicide resistance. The recent developments in studies related to plant-derived essential oil products has led to the discovery of a [...] Read more.
The management of insect pests and fungal diseases that cause damage to crops has become challenging due to the rise of pesticide and fungicide resistance. The recent developments in studies related to plant-derived essential oil products has led to the discovery of a range of phytochemicals with the potential to combat pesticide and fungicide resistance. This review paper summarizes and interprets the findings of experimental work based on plant-based essential oils in combination with existing pesticidal and fungicidal agents and novel bioactive natural and synthetic molecules against the insect pests and fungi responsible for the damage of crops. The insect mortality rate and fractional inhibitory concentration were used to evaluate the insecticidal and fungicidal activities of essential oil synergists against crop-associated pests. A number of studies have revealed that plant-derived essential oils are capable of enhancing the insect mortality rate and reducing the minimum inhibitory concentration of commercially available pesticides, fungicides and other bioactive molecules. Considering these facts, plant-derived essential oils represent a valuable and novel source of bioactive compounds with potent synergism to modulate crop-associated insect pests and phytopathogenic fungi. Full article
(This article belongs to the Special Issue Chemistry of Essential Oils and Food Flavours)
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13 pages, 1498 KiB  
Review
Backhousia citriodora F. Muell. (Lemon Myrtle), an Unrivalled Source of Citral
by Ian Southwell
Foods 2021, 10(7), 1596; https://doi.org/10.3390/foods10071596 - 09 Jul 2021
Cited by 20 | Viewed by 5336
Abstract
Lemon oils are amongst the highest volume and most frequently traded of the flavor and fragrance essential oils. Citronellal and citral are considered the key components responsible for the lemon note with citral (neral + geranial) preferred. Of the myriad of sources of [...] Read more.
Lemon oils are amongst the highest volume and most frequently traded of the flavor and fragrance essential oils. Citronellal and citral are considered the key components responsible for the lemon note with citral (neral + geranial) preferred. Of the myriad of sources of citral, the Australian myrtaceous tree, Lemon Myrtle, Backhousia citriodora F. Muell. (Myrtaceae), is considered superior. This review examines the history, the natural occurrence, the cultivation, the taxonomy, the chemistry, the biological activity, the toxicology, the standardisation and the commercialisation of Backhousia citriodora especially in relation to its essential oil. Full article
(This article belongs to the Special Issue Chemistry of Essential Oils and Food Flavours)
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