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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 June 2022) | Viewed by 21197

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Prof. Dr. Igor Jerković

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Department of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, HR-21000 Split, Croatia
Interests: volatile organic compounds (terpenes, norisoprenoids, aliphatic and aromatic compounds, others); glycosidically bound volatiles; chemical biomarkers; chemical biodiversity; gas chromatography and mass spectrometry; organic chemistry
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Dear Colleagues,

Following the success of the Special Issue “Progress in Volatile Organic Compound Research”, in which 15 research papers were published, we have decided it is both timely and pertinent to launch a second edition. Volatile organic compounds (VOCs) have been intensively investigated in recent years from different origins: plant/marine algae secondary metabolites, food/beverage aroma, fungal/bacterial volatiles, and others. Naturally occurring VOCs are a more or less complex mixture of monoterpenes, sesquiterpenes, norisoprenoids, aliphatic/aromatic compounds, sulfur or nitrogen containing compounds, and others. They are formed through different biochemical pathways and could be modified or created (artefacts) during drying or maturation, thermal treatment, and others. Different conventional or innovative methods of VOC isolation followed by analysis with chromatographic and spectroscopic techniques (most often mass spectrometry) provide different VOC chemical profiles. Chemical biomarkers of botanical origin or chemotaxonomic markers or essential oil chemotypes can be found. Among others, ecological interactions are mediated by VOCs (inter- and intraorganismic communication), and they can act as pheromones, attractants or alleochemicals. Many VOCs possess different biological activities, such as antioxidant, antimicrobial, antiviral, anticancer, and others.

Although the successful previous issue did a great job in covering many of these issues, there is still a great need to report VOCs from different sources and to discover and communicate their distribution, chemical profiles or individual compounds. This Special Issue “Progress in Volatile Organic Compound Research II” aims to attract up-to-date contributions on all aspects of VOC chemistry (from challenges in their isolation/extraction, analysis/structure determination to synthesis) and on unlocking their biological activities or other useful properties.

Prof. Dr. Igor Jerković
Guest Editor

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Keywords

Volatile organic compounds
Essential oils
Headspace compounds
Modern methods of volatiles isolation, analysis or synthesis
Chemical or chemotaxonomic biomarkers
Pheromones, attractants, alleochemicals
Biological activity
GC–MS

Related Special Issue

Progress in Volatile Organic Compounds Research in Molecules (15 articles)

Published Papers (10 papers)

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Research

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25 pages, 5572 KiB

Open AccessArticle

Elicitor-Induced VOC Emission by Grapevine Leaves: Characterisation in the Vineyard

by Christelle Lemaitre-Guillier, Agnès Chartier, Christelle Dufresne, Antonin Douillet, Stéphanie Cluzet, Josep Valls, Nicolas Aveline, Xavier Daire and Marielle Adrian

Molecules 2022, 27(18), 6028; https://doi.org/10.3390/molecules27186028 - 15 Sep 2022

Cited by 1 | Viewed by 1401

Abstract

The present study is aimed at determining whether leaf volatile organic compounds (VOCs) are good markers of the grapevine response to defence elicitors in the field. It was carried out in two distinct French vineyards (Burgundy and Bordeaux) over 3 years. The commercial elicitor Bastid^® (Syngenta, Saint-Sauveur, France) (COS-OGA) was first used to optimise the VOCs’ capture in the field; by bagging stems together with a stir bar sorptive extraction (SBSE) sensor. Three elicitors (Bastid^®, copper sulphate and methyl jasmonate) were assessed at three phenological stages of the grapevines by monitoring stilbene phytoalexins and VOCs. Stilbene production was low and variable between treatments and phenological stages. VOCs—particularly terpenes—were induced by all elicitors. However, the response profiles depended on the type of elicitor, the phenological stage and the vineyard, and no sole common VOC was found. The levels of VOC emissions discriminated between weak (Bastid^® and copper sulphate) and strong (methyl jasmonate) inducers. Ocimene isomers were constitutively present in the overall blends of the vineyards and increased by the elicitors’ treatments, whilst other VOCs were newly released throughout the growing seasons. Nonetheless, the plant development and climate factors undoubtedly influenced the release and profiles of the leaf VOCs. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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10 pages, 2082 KiB

Open AccessArticle

Chemical Approach to the Optimization of Conditions Using HS-SPME/GC–MS for Characterization of Volatile Compounds in Eugenia brasiliensis Fruit

by Ana Luiza Coeli Cruz Ramos, Laiza Andrade Nogueira, Mauro Ramalho Silva, Ana Carolina do Carmo Mazzinghy, Ana Paula Xavier Mariano, Tássia Nunes de Albuquerque Rodrigues, Ana Cardoso Clemente Filha Ferreira de Paula, Angelita Cristine de Melo, Rodinei Augusti, Raquel Linhares Bello de Araújo, Inayara Cristina Alves Lacerda and Júlio Onésio Ferreira Melo

Molecules 2022, 27(15), 4955; https://doi.org/10.3390/molecules27154955 - 04 Aug 2022

Cited by 1 | Viewed by 1470

Abstract

Grumixama (Eugenia brasiliensis Lam.) is a native fruit of the Brazilian Atlantic Forest, belonging to the Myrtaceae family, which designatesthe most significant number of species with food potential. It stands out due to its phytochemical characteristics because of the presence of polyphenols and volatile organic compounds. Volatile compounds are substances released by foods that give off an aroma and influence flavor. Solid-phase microextraction is a technique that allows for low-cost, fast, and solvent-free extraction, has an affinity for numerous analytes, and is easily coupled to gas chromatography. The objectives of this work were to evaluate the efficiency of different fibers of SPME (solid-phase microextraction) in the extraction of volatile organic compounds from grumixama pulp; optimize a method for extraction time, temperature, and sample weight; and to determine the characteristic volatile profile of this fruit. For the extraction of volatile compounds, three fibers of different polarities were used: polar polyacrylate (PA) fibers, divinylbenzene/carboxyne/polydimethylsiloxane (DVB/CAR/PDMS) semipolar fibers, and polydimethylsiloxane/divinylbenzene (PDMS/DVB). Fourteen volatile organic compounds (VOCs) were identified by DVB/CAR/PDMS, six by PA, and seven by PDMS/DVB through solid-phase microextraction in the headspace mode (SPME-HS). Considering the total number of compounds identified, regardless of the fiber used, and the optimization of the method, Eugenia brasiliensis presented sesquiterpene fractions (85.7%, 83.3%, and 85.7% of total VOCs) higher than the monoterpene fractions (14.3%, 16.7%, and 14.3%) for DVB/CAR/PDMS, PA, and PDMS/DVB, respectively in its composition. In addition, it was possible to verify that the fiber DVB/CAR/PDMS presented a better efficiency due to the larger chromatographic area observed when the grumixama pulp was subjected to conditions of 75 °C, 2.0 g, and an adsorption time of 20 min. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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11 pages, 1780 KiB

Open AccessArticle

Fumigant Activity of Bacterial Volatile Organic Compounds against the Nematodes Caenorhabditis elegans and Meloidogyne incognita

by Ali Diyapoglu, Tao-Ho Chang, Pi-Fang Linda Chang, Jyh-Herng Yen, Hsin-I Chiang and Menghsiao Meng

Molecules 2022, 27(15), 4714; https://doi.org/10.3390/molecules27154714 - 23 Jul 2022

Cited by 3 | Viewed by 1768

Abstract

Plant-parasitic nematodes infect a diversity of crops, resulting in severe economic losses in agriculture. Microbial volatile organic compounds (VOCs) are potential agents to control plant-parasitic nematodes and other pests. In this study, VOCs emitted by a dozen bacterial strains were analyzed using solid-phase microextraction followed by gas chromatography–mass spectrometry. Fumigant toxicity of selected VOCs, including dimethyl disulfide (DMDS), 2-butanone, 2-pentanone, 2-nonanone, 2-undecanone, anisole, 2,5-dimethylfuran, glyoxylic acid, and S-methyl thioacetate (MTA) was then tested against Caenorhabditis elegans. DMDS and MTA exhibited much stronger fumigant toxicity than the others. Probit analysis suggested that the values of LC₅₀ were 8.57 and 1.43 μg/cm³ air for DMDS and MTA, respectively. MTA also showed stronger fumigant toxicity than DMDS against the root-knot nematode Meloidogyne incognita, suggesting the application potential of MTA. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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13 pages, 2009 KiB

Open AccessArticle

Seasonal Variability of a Caryophyllane Chemotype Essential Oil of Eugenia patrisii Vahl Occurring in the Brazilian Amazon

by Ellen de Nazaré S. da Cruz, Luana de Sousa Peixoto, Jamile S. da Costa, Rosa Helena V. Mourão, Walnice Maria O. do Nascimento, José Guilherme S. Maia, William N. Setzer, Joyce Kelly da Silva and Pablo Luis B. Figueiredo

Molecules 2022, 27(8), 2417; https://doi.org/10.3390/molecules27082417 - 08 Apr 2022

Cited by 15 | Viewed by 1647

Abstract

Eugenia patrisii Vahl is a native and non-endemic myrtaceous species of the Brazilian Amazon. Due to few botanical and phytochemical reports of this species, the objective of the present work was to evaluate the seasonal variability of their leaf essential oils, performed by GC and GC-MS and chemometric analysis. The results indicated that the variation in oil yields (0.7 ± 0.1%) could be correlated with climatic conditions and rainy (R) and dry seasons (D). (E)-caryophyllene (R = 17.1% ± 16.0, D = 20.2% ± 17.7) and caryophyllene oxide (R = 30.1% ± 18.4, D = 14.1% ± 19.3) are the major constituents and did not display significant differences between the two seasons. However, statistically, a potential correlation between the main constituents of E. patrisii essential oil and the climatic parameters is possible. It was observed that the higher temperature and insolation rates and the lower humidity rate, which are characteristics of the dry season, lead to an increase in the (E)-caryophyllene contents, while lower temperature and insolation and higher humidity, which occur in the rainy season, lead to an increase in the caryophyllene oxide content. The knowledge of variations in the E. patrisii essential oil composition could help choose the best plant chemical profile for medicinal purposes. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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19 pages, 2001 KiB

Open AccessArticle

Chemical Composition and Variability of the Volatile Components of Myrciaria Species Growing in the Amazon Region

by Jamile Silva da Costa, Waldemir Magno S. Andrade, Raphael O. de Figueiredo, Paulo Vinicius L. Santos, Jofre Jacob da Silva Freitas, William N. Setzer, Joyce Kelly R. da Silva, José Guilherme S. Maia and Pablo Luis B. Figueiredo

Molecules 2022, 27(7), 2234; https://doi.org/10.3390/molecules27072234 - 30 Mar 2022

Cited by 6 | Viewed by 2436

Abstract

Myrciaria (Myrtaceae) species have been well investigated due to their chemical and biological relevance. The present work aimed to carry out the chemotaxonomic study of essential oils of the species M. dubia, M. floribunda, and M. tenella, sampled in the Brazilian Amazon and compare them with the volatile compositions from other Myrciaria species reported to Brazil and Colombia. The leaves of six Myrciaria specimens were collected (PA, Brazil) during the dry season, and their chemical compositions were analyzed by gas chromatography-mass spectrometer (GC-MS) and gas chromatography-flame ionization detector (GC-FID). The main compounds identified in the essential oils were monoterpenes with pinane and menthane skeletons, followed by sesquiterpenes with caryophyllane and cadinane skeletons. Among the sampled Myrciaria specimens, five chemical profiles were reported for the first time: profile I (M. dubia, α-pinene, 54.0–67.2%); profile II (M. floribunda, terpinolene 23.1%, α-phellandrene 17.7%, and γ-terpinene 8.7%); profile III (M. floribunda, γ-cadinene 17.5%, and an unidentified oxygenated sesquiterpene 15.0%); profile IV (M. tenella, E-caryophyllene 43.2%, and α-humulene 5.3%); and profile V (M. tenella, E-caryophyllene 19.1%, and caryophyllene oxide 41.1%). The Myrciaria chemical profiles showed significant variability in extraction methods, collection sites, plant parts, and genetic aspects. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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11 pages, 1171 KiB

Open AccessArticle

Volatile Organic Compounds from Bacillus aryabhattai MCCC 1K02966 with Multiple Modes against Meloidogyne incognita

by Wen Chen, Jinping Wang, Dian Huang, Wanli Cheng, Zongze Shao, Minmin Cai, Longyu Zheng, Ziniu Yu and Jibin Zhang

Molecules 2022, 27(1), 103; https://doi.org/10.3390/molecules27010103 - 24 Dec 2021

Cited by 15 | Viewed by 2620

Abstract

Plant-parasitic nematodes cause severe losses to crop production and economies all over the world. Bacillus aryabhattai MCCC 1K02966, a deep-sea bacterium, was obtained from the Southwest Indian Ocean and showed nematicidal and fumigant activities against Meloidogyne incognita in vitro. The nematicidal volatile organic compounds (VOCs) from the fermentation broth of B. aryabhattai MCCC 1K02966 were investigated further using solid-phase microextraction gas chromatography-mass spectrometry. Four VOCs, namely, pentane, 1-butanol, methyl thioacetate, and dimethyl disulfide, were identified in the fermentation broth. Among these VOCs, methyl thioacetate exhibited multiple nematicidal activities, including contact nematicidal, fumigant, and repellent activities against M. incognita. Methyl thioacetate showed a significant contact nematicidal activity with 87.90% mortality at 0.01 mg/mL by 72 h, fumigant activity in mortality 91.10% at 1 mg/mL by 48 h, and repellent activity at 0.01–10 mg/mL. In addition, methyl thioacetate exhibited 80–100% egg-hatching inhibition on the 7th day over the range of 0.5 mg/mL to 5 mg/mL. These results showed that methyl thioacetate from MCCC 1K02966 control M. incognita with multiple nematicidal modes and can be used as a potential biological control agent. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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12 pages, 1080 KiB

Open AccessArticle

Assessment of the In Vivo and In Vitro Release of Chemical Compounds from Vespa velutina

by M. Shantal Rodríguez-Flores, Soraia I. Falcão, Olga Escuredo, Luis Queijo, M. Carmen Seijo and Miguel Vilas-Boas

Molecules 2021, 26(22), 6769; https://doi.org/10.3390/molecules26226769 - 09 Nov 2021

Cited by 1 | Viewed by 1901

Abstract

Vespa velutina has been rapidly expanding throughout Galicia since 2012. It is causing human health risks and well-known losses in the beekeeping sector. Control methods are scarce, unspecific, and ineffective. Semiochemicals are insect-derived chemicals that play a role in communication and they could be used an integrated pest management tool alternative to conventional pesticides. A previous determination of the organic chemical profile should be the first step in the study of these semiochemicals. HS-SPME in living individuals and the sting apparatus extraction followed by GC-MS spectrometry were combined to extract a possible profile of these compounds in 43 hornets from Galicia. The identified compounds were hydrocarbons, ketones, terpenes, and fatty acid, and fatty acid esters. Nonanal aldehyde appeared in important concentrations in living individuals. While pentadecane, 8-hexyl- and ethyl oleate were mainly extracted from the venom apparatus. Ketones 2-nonanone, 2-undecanone and 7-nonen-2-one, 4,8-dimethyl- were identified by both procedures, as was 1,7-Nonadiene, 4,8-dimethyl-. Some compounds were detected for the first time in V. velutina such as naphthalene, 1,6-dimethyl-4-(1-methylethyl). The chemical profile by caste was also characterized. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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17 pages, 798 KiB

Open AccessArticle

Volatilome and Essential Oil of Ulomoides dermestoides: A Broad-Spectrum Medical Insect

by Paulina J. Cázares-Samaniego, Claudia G. Castillo, Miguel A. Ramos-López and Marco M. González-Chávez

Molecules 2021, 26(20), 6311; https://doi.org/10.3390/molecules26206311 - 19 Oct 2021

Cited by 8 | Viewed by 1991

Abstract

Ulomoides dermestoides are used as a broad-spectrum medical insect in the alternative treatment of various diseases. Preliminary volatilome studies carried out to date have shown, as the main components, methyl-1,4-benzoquinone, ethyl-1,4-benzoquinone, 1-tridecene, 1-pentadecene, and limonene. This work focused on the production of metabolites and their metabolic variations in U. dermestoides under stress conditions to provide additional valuable information to help better understand the broad-spectrum medical uses. To this end, VOCs were characterized by HS-SPME with PEG and CAR/PDMS fibers, and the first reported insect essential oils were obtained. In HS-SMPE, we found 17 terpenes, six quinones, five alkenes, and four aromatic compounds; in the essential oils, 53 terpenes, 54 carboxylic acids and derivatives, three alkynes, 12 alkenes (1-Pentadecene, EOT1: 77.6% and EOT2: 57.9%), 28 alkanes, nine alkyl disulfides, three aromatic compounds, 19 alcohols, three quinones, and 12 aldehydes were identified. Between both study approaches, a total of 171 secondary metabolites were identified with no previous report for U. dermestoides. A considerable number of the identified metabolites showed previous studies of the activity of pharmacological interest. Therefore, considering the wide variety of activities reported for these metabolites, this work allows a broader vision of the therapeutic potential of U. dermestoides in traditional medicine. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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12 pages, 2194 KiB

Open AccessArticle

Identification and Evaluation of Aromatic Volatile Compounds in 26 Cultivars and 8 Hybrids of Freesia hybrida

by Shidan Weng, Xueqing Fu, Yu Gao, Tianlei Liu, Yi Sun and Dongqin Tang

Molecules 2021, 26(15), 4482; https://doi.org/10.3390/molecules26154482 - 25 Jul 2021

Cited by 5 | Viewed by 2312

Abstract

Freesia hybrida is a group of cultivars in the genus Freesia with a strong floral scent composed of diverse volatile organic compounds (VOCs). In this study, the VOCs of 34 F. hybrida were extracted and analyzed by headspace solid phase microextraction and gas chromatography mass spectrometry (HS-SPME-GC-MS). A total of 164 VOCs whose relative contents were higher than 0.05% were detected. The numbers of VOCs in all germplasms differed between 11 to 38, and the relative contents ranged from 32.39% to 94.28%, in which most germplasms were higher than 80%. Terpenoids, especially monoterpenes, were the crucial type of VOCs in most germplasms, of which linalool and D-limonene were the most frequently occurring. Principal component analysis (PCA) clearly separated samples based on whether linalool was the main component, and hierarchical clustering analysis (HCA) clustered samples into 4 groups according to the preponderant compounds linalool and (E)-β-ocimene. Comparison of parental species and hybrids showed heterosis in three hybrids, and the inherited and novel substances suggested that monoterpene played an important role in F. hybrida floral scent. This study established a foundation for the evaluation of Freesia genetic resources, breeding for the floral aroma and promoting commercial application. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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Review

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12 pages, 331 KiB

Open AccessReview

Application Potential of Bacterial Volatile Organic Compounds in the Control of Root-Knot Nematodes

by Ali Diyapoglu, Muhammet Oner and Menghsiao Meng

Molecules 2022, 27(14), 4355; https://doi.org/10.3390/molecules27144355 - 07 Jul 2022

Cited by 10 | Viewed by 2312

Abstract

Plant-parasitic nematodes (PPNs) constitute the most damaging group of plant pathogens. Plant infections by root-knot nematodes (RKNs) alone could cause approximately 5% of global crop loss. Conventionally, chemical-based methods are used to control PPNs at the expense of the environment and human health. Accordingly, the development of eco-friendly and safer methods has been urged to supplement or replace chemical-based methods for the control of RKNs. Using microorganisms or their metabolites as biological control agents (BCAs) is a promising approach to controlling RKNs. Among the metabolites, volatile organic compounds (VOCs) have gained increasing attention because of their potential in the control of not only RKNs but also other plant pathogens, such as insects, fungi, and bacteria. This review discusses the biology of RKNs as well as the status of various control strategies. The discovery of VOCs emitted by bacteria from various environmental sources and their application potential as BCAs in controlling RKNs are specifically addressed. Full article

(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)

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