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Featured Reviews on Bioactive Flavour and Fragrance Compounds

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Flavours and Fragrances".

Deadline for manuscript submissions: closed (15 October 2021) | Viewed by 62434

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Dr. Domenico Montesano

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Department of Pharmacy, University Federico II of Naples, Via D. Montesano 49, 80131 Naples, Italy
Interests: food safety and food quality; metabolomics; food chemistry; chromatography; mass-spectrometry; nutraceuticals; novel foods; methods of extraction
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Riccardo Petrelli

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Chemistry Interdisciplinary Project (CHIP), School of Pharmacy, University of Camerino, Via Madonna delle Carceri, 62032 Camerino, Italy
Interests: medicinal chemistry; small-molecules; essential oils; naturally-occurring compounds; NAD-dependent enzymes; plant secondary metabolites; bioactive-active fractionation; phytochemicals; ethnopharmacology; biological activity of natural compounds
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The plant secondary metabolism relies on thousands of volatile organic compounds (VOCs) which play important roles in plant physiology and defense systems. They are synthesized in the cell plastid and cytosol by specific enzymes and chemically characterized as terpenoids and aromatic and aliphatic compounds. VOCs are obtainable under a liquid, hydrophobic form named ‘essential oil’, through the classical techniques of steam- and hydrodistillation and cold pressing, although unconventional extraction techniques have also recently been used. In addition to affecting the sensory qualities of foods, cosmetics, and perfumes, VOCs are currently considered important mediators of biological activities. The fragrance industry produces hundred thousand tons of essential oils every year, which are designed for perfume manufacturing. However, they have shown an interesting potential of use in other sectors such as food, agriculture, and pharmaceutics. Nevertheless, only a little part of them is devoted to replacing the use of currently marketed pesticides and to supporting agriculture in facing environmental challenges.

As a result of the worldwide population’s growth (which is expected to rise from 7.5 to 10 billion by 2050), FAO recently released a document where they forewarn that a significant increase in agriculture production would be recommended to meet the future demand for food. The yield of grain crops has already reached a “plateau”, and the indiscriminate use of synthetic pesticides has caused serious problems with environmental pollution and food safety. In addition, global warming will be responsible for progressive exposure of soils to degradation and loss of fertility and will play an important role in the spreading of plant pathogens responsible for frequent epidemics. In this scenario, VOCs represent a natural, eco-sustainable, and ecofriendly strategy to enhance future smart agriculture while preserving the environment, natural resources, and human health. However, the high costs associated with scalability, formulation, and marketing may represent their limit, which may affect the initial investments. On the other hand, restrictive legislation on the use of chemical pesticides and the current increasing attention of the food and agrochemical industries on sustainable and ecofriendly solutions could attract significant investments, thus making VOCs more appealing.

On this basis, this Special Issue is designed to gather review papers dealing with the potential of VOCs in agriculture, food, and pharmaceutical applications through the study of their extraction and characterization, evaluation of their biological properties, and development of targeted delivery systems (e.g., micro and nanoemulsions).

Dr. Domenico Montesano
Dr. Riccardo Petrelli
Guest Editors

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Keywords

Essential oils
Agriculture
Food
Formulations
Crop protection
Insecticides
Extraction techniques
Chemical characterization
Biological activity

Related Special Issues

Featured Papers on Bioactive Flavour and Fragrance Compounds 2022 in Molecules (13 articles)
Featured Papers on Bioactive Flavour and Fragrance Compounds 2023 in Molecules (1 article)

Published Papers (10 papers)

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Review

42 pages, 942 KiB

Open AccessReview

Toxics or Lures? Biological and Behavioral Effects of Plant Essential Oils on Tephritidae Fruit Flies

by Valeria Zeni, Giovanni Benelli, Orlando Campolo, Giulia Giunti, Vincenzo Palmeri, Filippo Maggi, Roberto Rizzo, Gabriella Lo Verde, Andrea Lucchi and Angelo Canale

Molecules 2021, 26(19), 5898; https://doi.org/10.3390/molecules26195898 - 29 Sep 2021

Cited by 16 | Viewed by 3368

Abstract

The family Tephritidae (Diptera) includes species that are highly invasive and harmful to crops. Due to globalization, international trade, and human displacement, their spread is continuously increasing. Unfortunately, the control of tephritid flies is still closely linked to the use of synthetic insecticides, which are responsible for detrimental effects on the environment and human health. Recently, research is looking for alternative and more eco-friendly tools to be adopted in Integrated Pest Management (IPM) programs. In this regard, essential oils (EOs) and their main compounds represent a promising alternative to chemical insecticides. EOs are made up of phytoconstituents formed from the secondary metabolism of many plants and can act as attractants or toxics, depending on the dose. Because of this unique characteristic, EOs and their main constituents are promising tools that can be used both in Sterile Insect Technique (SIT) programs and in the “lure and kill” technique, exploiting the attractiveness of the product in the former case and its toxicity in the latter. In this article, current knowledge on the biological and behavioral effects of EOs and their main constituents on tephritid fruit flies is reviewed, mainly focusing on species belonging to the Anastrepha, Bactrocera, Ceratitis, and Zeugodacus genera. The mechanisms of action of EOs, their real-world applications, and challenges related to their use in IPM are critically discussed. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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29 pages, 1653 KiB

Open AccessReview

Characterization of the Aroma Profile and Main Key Odorants of Espresso Coffee

by Simone Angeloni, Ahmed M. Mustafa, Doaa Abouelenein, Laura Alessandroni, Laura Acquaticci, Franks Kamgang Nzekoue, Riccardo Petrelli, Gianni Sagratini, Sauro Vittori, Elisabetta Torregiani and Giovanni Caprioli

Molecules 2021, 26(13), 3856; https://doi.org/10.3390/molecules26133856 - 24 Jun 2021

Cited by 38 | Viewed by 7089

Abstract

Espresso coffee (EC) is a common coffee preparation technique that nowadays is broadly widespread all over the globe. Its popularity is in part attributed to the intense aroma and pleasant flavor. Many researchers have studied and reviewed the aroma of the coffee, but there is a lack of specific review focused on EC aroma profile even if it is intensively investigated. Thus, the objective of the current review was to summarize the aroma profile of EC and how different preparation variables can affect EC flavor. Moreover, a collection of diverse analytical procedures for volatile analysis was also reported. The findings of this survey showed that the volatile fraction of EC is extremely complex, but just some compounds are responsible for the characteristic aroma of the coffee, such as some aldehyde, ketones, furanones, furans, sulfur compounds, pyrazines, etc. In addition, during preparation, some variables, e.g., temperature and pressure of water, granulometry of the coffee particle, and brew ratio, can also modify the aroma profile of this beverage, and therefore its quality. A better understanding of the aroma fraction of EC and how the preparation variables should be adjusted according to desired EC would assist coffee workers in obtaining a higher quality product. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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51 pages, 2150 KiB

Open AccessReview

Back to the Roots—An Overview of the Chemical Composition and Bioactivity of Selected Root-Essential Oils

by Karin Lunz and Iris Stappen

Molecules 2021, 26(11), 3155; https://doi.org/10.3390/molecules26113155 - 25 May 2021

Cited by 25 | Viewed by 6128

Abstract

Since ancient times, plant roots have been widely used in traditional medicine for treating various ailments and diseases due to their beneficial effects. A large number of studies have demonstrated that—besides their aromatic properties—their biological activity can often be attributed to volatile constituents. This review provides a comprehensive overview of investigations into the chemical composition of essential oils and volatile components obtained from selected aromatic roots, including Angelica archangelica, Armoracia rusticana, Carlina sp., Chrysopogon zizanioides, Coleus forskohlii, Inula helenium, Sassafras albidum, Saussurea costus, and Valeriana officinalis. Additionally, their most important associated biological impacts are reported, such as anticarcinogenic, antimicrobial, antioxidant, pesticidal, and other miscellaneous properties. Various literature and electronic databases—including PubMed, ScienceDirect, Springer, Scopus, Google Scholar, and Wiley—were screened and data was obtained accordingly. The results indicate the promising properties of root-essential oils and their potential as a source for natural biologically active products for flavor, pharmaceutical, agricultural, and fragrance industries. However, more research is required to further establish the mechanism of action mediating these bioactivities as well as essential oil standardization because the chemical composition often strongly varies depending on external factors. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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21 pages, 3391 KiB

Open AccessReview

Fleeting Beauty—The World of Plant Fragrances and Their Application

by Angelika Kliszcz, Andrzej Danel, Joanna Puła, Beata Barabasz-Krasny and Katarzyna Możdżeń

Molecules 2021, 26(9), 2473; https://doi.org/10.3390/molecules26092473 - 23 Apr 2021

Cited by 9 | Viewed by 4439

Abstract

This article is devoted to some aspects of the fragrant substances of plant origin applied in the food industry and perfumery as well. Since antiquity many extractive techniques have been developed to obtain essential oils. Some of them are still applied, but new ones, like microwave or ultrasound-assisted extractions, are more and more popular and they save time and cost. Independently of the procedure, the resulting essential oils are the source of many so-called isolates. These can be applied as food additives, medicines, or can be used as starting materials for organic synthesis. Some substances exist in very small amounts in plant material so the extraction is not economically profitable but, after their chemical structures were established and synthetic procedures were developed, in some cases they are prepared on an industrial scale. The substances described below are only a small fraction of the 2000–3000 fragrant molecules used to make our life more enjoyable, either in food or perfumes. Additionally, a few examples of allelopathic fragrant compounds, present in their natural state, will be denoted and some of their biocidal features will be mentioned as an arising “green” knowledge in agriculture. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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43 pages, 9507 KiB

Open AccessReview

Monoterpenes and Sesquiterpenes of Essential Oils from Psidium Species and Their Biological Properties

by Renan Campos e Silva, Jamile S. da Costa, Raphael O. de Figueiredo, William N. Setzer, Joyce Kelly R. da Silva, José Guilherme S. Maia and Pablo Luis B. Figueiredo

Molecules 2021, 26(4), 965; https://doi.org/10.3390/molecules26040965 - 12 Feb 2021

Cited by 31 | Viewed by 4255

Abstract

Psidium (Myrtaceae) comprises approximately 266 species, distributed in tropical and subtropical regions of the world. Psidium taxa have great ecological, economic, and medicinal relevance due to their essential oils’ chemical diversity and biological potential. This review reports 18 Psidium species growing around the world and the chemical and biological properties of their essential oils. Chemically, 110 oil records are reported with significant variability of volatile constituents, according to their seasonality and collection sites. Monoterpenes and sesquiterpenes with acyclic (C₁₀ and C₁₅), p-menthane, pinane, bisabolane, germacrane, caryophyllane, cadinane, and aromadendrane skeleton-types, were the primary constituents. The essential oils showed various biological activities, including antioxidant, antifungal, antibacterial, phytotoxic, larvicidal, anti-inflammatory, and cytotoxic properties. This review contributes to the Psidium species rational and economic exploration as natural sources to produce new drugs. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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31 pages, 1996 KiB

Open AccessEditor’s ChoiceReview

Current Advances in the Bacterial Toolbox for the Biotechnological Production of Monoterpene-Based Aroma Compounds

by Pedro Soares-Castro, Filipa Soares and Pedro M. Santos

Molecules 2021, 26(1), 91; https://doi.org/10.3390/molecules26010091 - 28 Dec 2020

Cited by 23 | Viewed by 4507

Abstract

Monoterpenes are plant secondary metabolites, widely used in industrial processes as precursors of important aroma compounds, such as vanillin and (−)-menthol. However, the physicochemical properties of monoterpenes make difficult their conventional conversion into value-added aromas. Biocatalysis, either by using whole cells or enzymes, may overcome such drawbacks in terms of purity of the final product, ecological and economic constraints of the current catalysis processes or extraction from plant material. In particular, the ability of oxidative enzymes (e.g., oxygenases) to modify the monoterpene backbone, with high regio- and stereo-selectivity, is attractive for the production of “natural” aromas for the flavor and fragrances industries. We review the research efforts carried out in the molecular analysis of bacterial monoterpene catabolic pathways and biochemical characterization of the respective key oxidative enzymes, with particular focus on the most relevant precursors, β-pinene, limonene and β-myrcene. The presented overview of the current state of art demonstrates that the specialized enzymatic repertoires of monoterpene-catabolizing bacteria are expanding the toolbox towards the tailored and sustainable biotechnological production of values-added aroma compounds (e.g., isonovalal, α-terpineol, and carvone isomers) whose implementation must be supported by the current advances in systems biology and metabolic engineering approaches. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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27 pages, 860 KiB

Open AccessReview

An Overview on Truffle Aroma and Main Volatile Compounds

by Ahmed M. Mustafa, Simone Angeloni, Franks Kamgang Nzekoue, Doaa Abouelenein, Gianni Sagratini, Giovanni Caprioli and Elisabetta Torregiani

Molecules 2020, 25(24), 5948; https://doi.org/10.3390/molecules25245948 - 15 Dec 2020

Cited by 39 | Viewed by 5802

Abstract

Truffles are underground edible fungi that grow symbiotically with plant roots. They have been globally considered as one of the most expensive foods because of their rarity, unique aroma, and high nutritional value as antioxidant, anti-inflammatory, antiviral, hepatoprotective, anti-mutagenic, antituberculoid immunomodulatory, antitumor, antimicrobial, and aphrodisiac. The unique flavor and fragrance of truffles is one of the main reasons to get worldwide attraction as a food product. So, the aim of this review was to summarize the relevant literature with particular attention to the active aroma components as well as the various sample preparation and analytical techniques used to identify them. The major analytical methods used for the determination of volatile organic compounds (VOC) in truffles are gas chromatography (GC), proton-transfer-reaction mass spectrometry (PTR-MS), and electronic nose sensing (EN). In addition, factors influencing truffle aroma are also highlighted. For this reason, this review can be considered a good reference for research concerning aroma profiles of different species of truffles to deepen the knowledge about a complex odor of various truffles. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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33 pages, 2010 KiB

Open AccessReview

Encapsulation of Flavours and Fragrances into Polymeric Capsules and Cyclodextrins Inclusion Complexes: An Update

by Diego Romano Perinelli, Giovanni Filippo Palmieri, Marco Cespi and Giulia Bonacucina

Molecules 2020, 25(24), 5878; https://doi.org/10.3390/molecules25245878 - 11 Dec 2020

Cited by 57 | Viewed by 10758

Abstract

Flavours and fragrances are volatile compounds of large interest for different applications. Due to their high tendency of evaporation and, in most cases, poor chemical stability, these compounds need to be encapsulated for handling and industrial processing. Encapsulation, indeed, resulted in being effective at overcoming the main concerns related to volatile compound manipulation, and several industrial products contain flavours and fragrances in an encapsulated form for the final usage of customers. Although several organic or inorganic materials have been investigated for the production of coated micro- or nanosystems intended for the encapsulation of fragrances and flavours, polymeric coating, leading to the formation of micro- or nanocapsules with a core-shell architecture, as well as a molecular inclusion complexation with cyclodextrins, are still the most used. The present review aims to summarise the recent literature about the encapsulation of fragrances and flavours into polymeric micro- or nanocapsules or inclusion complexes with cyclodextrins, with a focus on methods for micro/nanoencapsulation and applications in the different technological fields, including the textile, cosmetic, food and paper industries. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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25 pages, 6440 KiB

Open AccessEditor’s ChoiceReview

Ionone Is More than a Violet’s Fragrance: A Review

by Lujain Aloum, Eman Alefishat, Abdu Adem and Georg Petroianu

Molecules 2020, 25(24), 5822; https://doi.org/10.3390/molecules25245822 - 10 Dec 2020

Cited by 43 | Viewed by 6558

Abstract

The term ionone is derived from “iona” (Greek for violet) which refers to the violet scent and “ketone” due to its structure. Ionones can either be chemically synthesized or endogenously produced via asymmetric cleavage of β-carotene by β-carotene oxygenase 2 (BCO2). We recently proposed a possible metabolic pathway for the conversion of α-and β-pinene into α-and β-ionone. The differences between BCO1 and BCO2 suggest a unique physiological role of BCO2; implying that β-ionone (one of BCO2 products) is involved in a prospective biological function. This review focuses on the effects of ionones and the postulated mechanisms or signaling cascades involved mediating these effects. β-Ionone, whether of an endogenous or exogenous origin possesses a range of pharmacological effects including anticancer, chemopreventive, cancer promoting, melanogenesis, anti-inflammatory and antimicrobial actions. β-Ionone mediates these effects via activation of olfactory receptor (OR51E2) and regulation of the activity or expression of cell cycle regulatory proteins, pro-apoptotic and anti-apoptotic proteins, HMG-CoA reductase and pro-inflammatory mediators. α-Ionone and β-ionone derivatives exhibit anti-inflammatory, antimicrobial and anticancer effects, however the corresponding structure activity relationships are still inconclusive. Overall, data demonstrates that ionone is a promising scaffold for cancer, inflammation and infectious disease research and thus is more than simply a violet’s fragrance. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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28 pages, 1867 KiB

Open AccessFeature PaperReview

The Impact of Electronic Nicotine Delivery System (ENDS) Flavors on Nicotinic Acetylcholine Receptors and Nicotine Addiction-Related Behaviors

by Skylar Y. Cooper and Brandon J. Henderson

Molecules 2020, 25(18), 4223; https://doi.org/10.3390/molecules25184223 - 15 Sep 2020

Cited by 14 | Viewed by 7807

Abstract

Over the past two decades, combustible cigarette smoking has slowly declined by nearly 11% in America; however, the use of electronic cigarettes has increased tremendously, including among adolescents. While nicotine is the main addictive component of tobacco products and a primary concern in electronic cigarettes, this is not the only constituent of concern. There is a growing market of flavored products and a growing use of zero-nicotine e-liquids among electronic cigarette users. Accordingly, there are few studies that examine the impact of flavors on health and behavior. Menthol has been studied most extensively due to its lone exception in combustible cigarettes. Thus, there is a broad understanding of the neurobiological effects that menthol plus nicotine has on the brain including enhancing nicotine reward, altering nicotinic acetylcholine receptor number and function, and altering midbrain neuron excitability. Although flavors other than menthol were banned from combustible cigarettes, over 15,000 flavorants are available for use in electronic cigarettes. This review seeks to summarize the current knowledge on nicotine addiction and the various brain regions and nicotinic acetylcholine receptor subtypes involved, as well as describe the most recent findings regarding menthol and green apple flavorants, and their roles in nicotine addiction and vaping-related behaviors. Full article

(This article belongs to the Special Issue Featured Reviews on Bioactive Flavour and Fragrance Compounds)

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