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Terpenes: Flavours, Fragrances and Pharmaceuticals
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Terpenes: Flavours, Fragrances and Pharmaceuticals

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

Deadline for manuscript submissions: closed (31 December 2022) | Viewed by 14833

Special Issue Editor

Dr. Hee-Sung Chae

E-Mail Website
Guest Editor
National Center for Natural Products Research, University of Mississippi, Oxford, MS 38677, USA
Interests: natural product; skin sensitizer; anti-inflammatory; metabolic syndrome; whole-transcriptome analysis

Special Issue Information

Dear Colleagues,

Terpenes, their derivatives and general isoprenoids, as natural secondary metabolites, play stable and growing roles in Flavours, Fragrances and Pharmaceuticals, and branch out into an increasing number of other fields. Their importance is based, i.a., on the fact that they are mostly bound to renewable sources, which makes them valuable within a circular economy. Terpenes and steroids are also a cause of stereochemistry, regioselectivity, chirality, and many other features and disciplines within science, development, and the industry on a scope which is indispensable.

This Special Issue aims to underline the current developments in all fields that are connected to terpene research and utilization.

Dr. Hee-Sung Chae
Guest Editor

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Keywords

  • isolation and analysis of terpenes
  • essential oil
  • anti-inflammatory terpenes
  • antioxidants
  • mode of action
  • skin sensitizer
  • dietary supplements

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Published Papers (4 papers)

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Research

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11 pages, 1066 KiB  
Article
Chemical Composition, Antimicrobial and Antioxidant Bioautography Activity of Essential Oil from Leaves of Amazon Plant Clinopodium brownei (Sw.)
by Paco Noriega, Lissette Calderón, Andrea Ojeda and Erika Paredes
Molecules 2023, 28(4), 1741; https://doi.org/10.3390/molecules28041741 - 11 Feb 2023
Cited by 5 | Viewed by 2316
Abstract
The Amazonian region of Ecuador has an extremely rich vegetal biodiversity, and its inhabitants have proven to have a millennial ancestral knowledge of the therapeutic and medicinal use of these resources. This work aimed to evaluate the chemical composition and biological activity of [...] Read more.
The Amazonian region of Ecuador has an extremely rich vegetal biodiversity, and its inhabitants have proven to have a millennial ancestral knowledge of the therapeutic and medicinal use of these resources. This work aimed to evaluate the chemical composition and biological activity of the essential oil obtained from the medicinal plant Clinopodium brownei (Sw.) Kuntze, which is widely spread in tropical and subtropical America. This species is traditionally used for treating respiratory and digestive diseases and is also known for its analgesic properties. Most of the molecules detected on a non-polar column were ethyl cinnamate 21.4%, pulegone 20.76%, methyl cinnamate 16.68%, caryophyllene 8.17%, β-selinene 7.92% and menthone 7.51%, while those detected on a polar column were: pulegone 29.90%, ethyl cinnamate 18.75%, methyl cinnamate 13.82%, caryophyllene 10.0% and menthone 8.04%. The antioxidant activity by the assays, DPPH (2.2-diphenyl-1-picrylhydrazyl) and ABTS (2.2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid)), shows the following values of 50% inhibition of oxidation, IC50 DPPH 1.77 mg/mL, IC50 ABTS 0.06 mg/mL, which, compared to the essential oil of Thymus vulgaris (natural positive control), turn out to be less active. Bioautography indicates that the molecules responsible for the antioxidant activity are derived from cinnamic acid: ethyl cinnamate and methyl cinnamate, and caryophyllene. The antimicrobial activity on the nine microorganisms evaluated shows bacterial growth inhibitory concentrations ranging from 13.6 mg/mL for Staphylococcus epidermidis ATCC 14990 to 3.1 mg/mL for Candida albicans ATCC 10231; the results are lower than those of the positive control. Bioautography assigns antimicrobial activity to caryophyllene. The results indicate a very interesting activity of the essential oil and several of its molecules, validating the traditional use and the importance of this medicinal plant from Ecuador. Full article
(This article belongs to the Special Issue Terpenes: Flavours, Fragrances and Pharmaceuticals)
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13 pages, 4656 KiB  
Article
Yeast Particles Hyper-Loaded with Terpenes for Biocide Applications
by Ernesto R. Soto, Florentina Rus and Gary R. Ostroff
Molecules 2022, 27(11), 3580; https://doi.org/10.3390/molecules27113580 - 2 Jun 2022
Cited by 5 | Viewed by 2512
Abstract
Yeast particles (YPs) are 3–5 µm hollow and porous microspheres, a byproduct of some food grade yeast (Saccharomyces cerevisiae) extract manufacturing processes. Terpenes can be efficiently encapsulated inside YPs by passive diffusion through the porous cell walls. As previously published, this [...] Read more.
Yeast particles (YPs) are 3–5 µm hollow and porous microspheres, a byproduct of some food grade yeast (Saccharomyces cerevisiae) extract manufacturing processes. Terpenes can be efficiently encapsulated inside YPs by passive diffusion through the porous cell walls. As previously published, this YP terpene encapsulation approach has been successfully implemented (1) to develop and commercialize fungicide and nematicide products for agricultural applications, (2) to co-load high potency agrochemical actives dissolved in terpenes or suitable solvents, and (3) to identify YP terpenes with broad-acting anthelmintic activity for potential pharmaceutical applications. These first-generation YP terpene materials were developed with a <2:1 terpene: YP weight ratio. Here we report methods to increase the terpene loading capacity in YPs up to 5:1 terpene: YP weight ratio. Hyper-loaded YP terpenes extend the kinetics of payload release up to three-fold compared to the commercialized YP terpene formulations. Hyper-loaded YP-terpene compositions were further optimized to achieve high terpene storage encapsulation stability from −20 °C to 54 °C. The development of hyper-loaded YP terpenes has a wide range of potential agricultural and pharmaceutical applications with terpenes and other compatible active substances that could benefit from a delivery system with a high payload loading capacity combined with increased payload stability and sustained release properties. Full article
(This article belongs to the Special Issue Terpenes: Flavours, Fragrances and Pharmaceuticals)
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13 pages, 1008 KiB  
Article
Chemical Constituents, Antioxidant, Anti-Tyrosinase, Cytotoxicity, and Anti-Melanogenesis Activities of Etlingera elatior (Jack) Leaf Essential Oils
by Sarita Sangthong, Itthayakorn Promputtha, Punyawatt Pintathong and Phanuphong Chaiwut
Molecules 2022, 27(11), 3469; https://doi.org/10.3390/molecules27113469 - 27 May 2022
Cited by 7 | Viewed by 2904
Abstract
Essential oils of plants have been used widely in cosmetic preparations. Being both perfuming and active ingredients, the functions of essential oils mean they are high-value ingredients. In this study, the leaf of Etlingera elatior (Jack) or Torch ginger was used. The essential [...] Read more.
Essential oils of plants have been used widely in cosmetic preparations. Being both perfuming and active ingredients, the functions of essential oils mean they are high-value ingredients. In this study, the leaf of Etlingera elatior (Jack) or Torch ginger was used. The essential oils (EO) were prepared by conventional hydrodistillation (HD) and microwave-assisted hydrodistillation (MAHD). The volatile compounds of EOs were analyzed by gas chromatography spectroscopy (GC-MS). The antioxidant activities by means of DPPH radical scavenging and ferric-reducing antioxidant power (FRAP) were determined. The inhibition of tyrosinase activity was investigated. The cytotoxicity was performed against human fibroblast cell lines (NIH/3T3) and melanoma cell lines (A375 and B16F10). The decreasing melanin content was measured in melanoma cell lines. The resulting essential oils were detected for 41 compounds from HD extraction dominants by terpenes, namely sesquiterpenes (48.499%) and monoterpenes (19.419%), while 26 compounds were detected from MAHD with the fatty alcohols as the major group. The higher antioxidant activities were found in HD EO (IC50 of 16.25 ± 0.09 mg/mL from DPPH assay and 0.91 ± 0.01 mg TEAC/g extract from FRAP assay). The survival of normal fibroblast cell lines remained at 90% at 500 µg/mL HD EO, where the EO possessed the half-maximal toxicity dose (TD50) of 214.85 ± 4.647 and 241.128 ± 2.134 μg/mL on B16F10 and A375 cell lines, respectively. This could suggest that the EO is highly selective against the melanoma cell lines. The melanin content was decreased at the half-maximum efficacy (IC50) at 252.12 ± 3.02 and 253.56 ± 3.65 in the A375 and B1610 cell lines, respectively, which were approximately 2.8-fold lower than kojic acid, the standard compound. The results of this study evidence the use of Etlingera elatior (Jack) leaf as a source of essential oil as an active agent in cosmetics. Full article
(This article belongs to the Special Issue Terpenes: Flavours, Fragrances and Pharmaceuticals)
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Review

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19 pages, 1427 KiB  
Review
Toxicity of Selected Monoterpenes and Essential Oils Rich in These Compounds
by Karolina A. Wojtunik-Kulesza
Molecules 2022, 27(5), 1716; https://doi.org/10.3390/molecules27051716 - 6 Mar 2022
Cited by 55 | Viewed by 6389
Abstract
Monoterpenes make up the largest group of plant secondary metabolites. They can be found in numerous plants, among others, the Lamiaceae family. The compounds demonstrate antioxidative, antibacterial, sedative and anti-inflammatory activity, hence, they are often employed in medicine and pharmaceuticals. Additionally, their fragrant [...] Read more.
Monoterpenes make up the largest group of plant secondary metabolites. They can be found in numerous plants, among others, the Lamiaceae family. The compounds demonstrate antioxidative, antibacterial, sedative and anti-inflammatory activity, hence, they are often employed in medicine and pharmaceuticals. Additionally, their fragrant character is often made use of, notably in the food and cosmetic industries. Nevertheless, long-lasting studies have revealed their toxic properties. This fact has led to a detailed analysis of the compounds towards their side effects on the human organism. Although most are safe for human food and medical applications, there are monoterpene compounds that, in certain amounts or under particular circumstances (e.g., pregnancy), can cause serious disorders. The presented review characterises in vitro and in vivo, the toxic character of selected monoterpenes (α-terpinene, camphor, citral, limonene, pulegone, thujone), as well as that of their original plant sources and their essential oils. The selected monoterpenes reveal various toxic properties among which are embryotoxic, neurotoxic, allergenic and genotoxic. It is also known that the essential oils of popular plants can also reveal toxic characteristics that many people are unaware of. Full article
(This article belongs to the Special Issue Terpenes: Flavours, Fragrances and Pharmaceuticals)
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