Special Issue "Evaluation and formulation of Bioactive Terpenes"

A special issue of Biomolecules (ISSN 2218-273X).

Deadline for manuscript submissions: closed (31 March 2019).

Special Issue Editors

Dr. Valdir Florencio Da Veiga Junior
E-Mail Website
Guest Editor
Instituto Militar de Engenharia, Rio de Janeiro, Brazil
Tel. +55 21 9911 58799
Prof. Ádley Antonini Neves de Lima
E-Mail
Guest Editor
Universidade Federal do Rio Grande do Norte; Department of Pharmacy; Natal
Prof. Letícia Scherer Koester
E-Mail
Guest Editor
Universidade Federal do Rio Grande do Sul; Pharmaceutical Sciences Graduate Program; Porto Alegre

Special Issue Information

Dear Colleagues,

Terpenes are very bioactive natural products. Terpenes are commonly found in extracts from plants, animals, and microorganisms, mainly in essential oils and oleoresins. Several bioactive terpenes, such as taxol, cannabidiol, resinous diterpenoids, sesquiterpene lactones, limonene, pinenes, and betulinic acid, have been studied to clarify their mechanism of action. Besides, studies have been conducted to enable their production at large scale, the development of their formulations, and the generation of these bioproducts. This Special Issue of Biomolecules presents several papers and review articles focused on the biological assessment of terpenes, upscaling the isolation and concentration of bioactive terpenes and the formulation strategies, mainly using nanotechnological approaches

Dr. Valdir Florencio da Veiga Junior
Prof. Ádley Antonini Neves de Lima
Prof. Letícia Scherer Koester
Guest Editors

Manuscript Submission Information

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Keywords

  • Terpenes
  • Formulations
  • Nanotechnology
  • Emulsions

Published Papers (7 papers)

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Research

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Open AccessArticle
Inclusion Complexes of β and HPβ-Cyclodextrin with α, β Amyrin and In Vitro Anti-Inflammatory Activity
Biomolecules 2019, 9(6), 241; https://doi.org/10.3390/biom9060241 - 21 Jun 2019
Abstract
α, β amyrin (ABAM) is a natural mixture of pentacyclic triterpenes that has a wide range of biological activities. ABAM is isolated from the species of the Burseraceae family, in which the species Protium is commonly found in the Amazon region of Brazil. [...] Read more.
α, β amyrin (ABAM) is a natural mixture of pentacyclic triterpenes that has a wide range of biological activities. ABAM is isolated from the species of the Burseraceae family, in which the species Protium is commonly found in the Amazon region of Brazil. The aim of this work was to develop inclusion complexes (ICs) of ABAM and β-cyclodextrin (βCD) and hydroxypropyl-β-cyclodextrin (HPβCD) by physical mixing (PM) and kneading (KN) methods. Interactions between ABAM and the CD’s as well as the formation of ICs were confirmed by physicochemical characterization in the solid state by Fourier transform infrared (FTIR), scanning electron microscopy (SEM), X-ray diffraction (XRD), thermogravimetry (TG) and differential scanning calorimetry (DSC). Physicochemical characterization indicated the formation of ICs with both βCD and HPβCD. Such ICs were able to induce changes in the physicochemical properties of ABAM. In addition, the formation of ICs with cyclodextrins showed to be an effective and promising alternative to enhance the anti-inflammatory activity and safety of ABAM. Full article
(This article belongs to the Special Issue Evaluation and formulation of Bioactive Terpenes)
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Open AccessArticle
Influence of Monoterpenes in Biological Activities of Nectandra megapotamica (Spreng.) Mez Essential Oils
Biomolecules 2019, 9(3), 112; https://doi.org/10.3390/biom9030112 - 21 Mar 2019
Abstract
Investigating the influence of seasonal variations on biological activities is important for pharmacological studies and metabolic engineering. Therefore, this study was conducted to determine the variation of the chemical composition of essential oils obtained from Nectandra megapotamica leaves, collected at different stages of [...] Read more.
Investigating the influence of seasonal variations on biological activities is important for pharmacological studies and metabolic engineering. Therefore, this study was conducted to determine the variation of the chemical composition of essential oils obtained from Nectandra megapotamica leaves, collected at different stages of plant development, as well as its influence on the biological activities. A total of 38 compounds were identified that accounted for 97–99.2% of the chemical composition of the oils. Major differences were observed in the monoterpenic fraction, representing 5.1% of the compounds identified in the productive rest phase to 37.1% in the blooming phase. Bicyclogermacrene and germacrene D were the predominant compounds identified in the oil of all collections. Furthermore, limonene, β-pinene, and spathulenol were identified predominantly in the samples of blooming and fruiting phases. The oils exhibited significant antichemotactic activity and different effects in scavenging the radical 2,2-diphenyl-1-picrylhydrazyl. Variations were also observed in the antifungal activity, with the minimum inhibitory concentrations ranging from 125 to 500 μg/mL. These results demonstrate the influence of monoterpenes, primarily limonene, α-pinene, and β-pinene, on the bioactivities of the oil. Studies investigating the variations in the chemical composition of essential oil may offer a strategy to produce a compound or a group of compounds of interest to industries with a specific pharmacological focus. Full article
(This article belongs to the Special Issue Evaluation and formulation of Bioactive Terpenes)
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Open AccessArticle
Triterpene Derivatives as Relevant Scaffold for New Antibiofilm Drugs
Biomolecules 2019, 9(2), 58; https://doi.org/10.3390/biom9020058 - 11 Feb 2019
Cited by 1
Abstract
New medicines for the treatment of bacterial biofilm formation are required. For this reason, this study shows the in vitro activity of betulinic acid (BA), ursolic acid (UA) and their twenty derivatives against planktonic and biofilm cells (gram-positive bacterial pathogens: Enterococcus faecalis, [...] Read more.
New medicines for the treatment of bacterial biofilm formation are required. For this reason, this study shows the in vitro activity of betulinic acid (BA), ursolic acid (UA) and their twenty derivatives against planktonic and biofilm cells (gram-positive bacterial pathogens: Enterococcus faecalis, Staphylococcus aureus and Staphylococcus epidermidis). We evaluated the antibiofilm activity (through the crystal violet method), as well as the antibacterial activity via absorbance (OD600) at concentrations of 5, 25 and 100 µM. Likewise, the cytotoxicity of all compounds was evaluated on a kidney African green monkey (VERO) cell line at the same concentration, by MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) methodology. We verified for the first time whether different groups at carbon 3 (C-3) of triterpenes may interfere in the antibiofilm activity with minimal or no antibacterial effect. After the screening of 22 compounds at three distinct concentrations, we found antibiofilm activity for eight distinct derivatives without antibiotic effect. In particular, the derivative 2f, with an isopentanoyl ester at position C-3, was an antibiofilm activity against S. aureus without any effect upon mammalian cells. Full article
(This article belongs to the Special Issue Evaluation and formulation of Bioactive Terpenes)
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Open AccessArticle
Anti-Tumor Activity of Cembranoid-Type Diterpenes Isolated from Nicotiana tabacum L.
Biomolecules 2019, 9(2), 45; https://doi.org/10.3390/biom9020045 - 28 Jan 2019
Abstract
Recently, the incidence of hepatocellular carcinoma has increased worldwide. Cembranoid-type diterpenes (CBDs) from tobacco exhibit good antimicrobial, antitumor, and neuroprotective activities. Therefore, in this study, we isolated CBDs from Nicotiana tabacum L. and evaluated their antitumor activity against hepatoma cell lines. Particularly, the [...] Read more.
Recently, the incidence of hepatocellular carcinoma has increased worldwide. Cembranoid-type diterpenes (CBDs) from tobacco exhibit good antimicrobial, antitumor, and neuroprotective activities. Therefore, in this study, we isolated CBDs from Nicotiana tabacum L. and evaluated their antitumor activity against hepatoma cell lines. Particularly, the anti-tumor activity of α-2,7,11-cyprotermine-4,6-diol (α-CBD) was investigated against HepG2, SMMC-7721, and HL-7702 cells. The MTT assay revealed that α-CBD reduced the formation of cell clones and inhibited the proliferation of hepatocellular carcinoma cells. Morphological observations showed that α-CBD altered cell morphology and membrane permeability before inducing apoptosis. To further explore the antitumor mechanism of α-CBD, flow cytometry and transcriptome analysis were performed using HepG2 cells. The results showed that the number of HepG2 cells increased from 10.4% to 29.8%, indicating that α-CBD inhibits the proliferation of hepatocellular carcinoma cells in the S phase. The gene expression analysis of HepG2 cells treated with α-CBD showed 3068 genes with altered expression, among which 1289 were upregulated and 1779 were downregulated. Apoptosis induced by these differentially expressed genes might be mediated by the p53-PUMA, PI3K-Akt, and IL-1-NF-κB-IAP pathways. Comprehensively, our study shows that α-CBD isolated from N. tabacum L. can be potentially used as a natural antitumor agent. Full article
(This article belongs to the Special Issue Evaluation and formulation of Bioactive Terpenes)
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Open AccessArticle
Enzymatic Synthesis and Characterization of a Novel α-1→6-Glucosyl Rebaudioside C Derivative Sweetener
Biomolecules 2019, 9(1), 27; https://doi.org/10.3390/biom9010027 - 14 Jan 2019
Cited by 2
Abstract
Zero-calorie high-intensity sweeteners from natural sources perform very well in the market place. This has encouraged food scientists to continue the effort to search for novel natural ingredients to satisfy consumer demand. Rebaudioside C (reb C) is the third most prevalent steviol glycoside [...] Read more.
Zero-calorie high-intensity sweeteners from natural sources perform very well in the market place. This has encouraged food scientists to continue the effort to search for novel natural ingredients to satisfy consumer demand. Rebaudioside C (reb C) is the third most prevalent steviol glycoside in the leaves of the Stevia rebaudiana Bertoni plant, but has limited applications in food and beverage products due to its low sweetness and high lingering bitterness compared to other major steviol glycosides, such as rebaudioside A (reb A). Here we present a new enzyme modification strategy to improve the taste profile of reb C by using Cargill’s propriety enzyme and sucrose as a glucose donor. A novel α-1→6-glucosyl reb C derivative was produced and its structure was elucidated by mass spectrometry and NMR spectroscopy. Sensory analysis demonstrated that this new reb C derivative has improved sweetness, reduced bitterness, and enhanced solubility in water. Full article
(This article belongs to the Special Issue Evaluation and formulation of Bioactive Terpenes)
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Review

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Open AccessReview
Essential Oils and Isolated Terpenes in Nanosystems Designed for Topical Administration: A Review
Biomolecules 2019, 9(4), 138; https://doi.org/10.3390/biom9040138 - 05 Apr 2019
Cited by 2
Abstract
Essential oils are natural products with a complex composition. Terpenes are the most common class of chemical compounds present in essential oils. Terpenes and the essential oils containing them are widely used and investigated by their pharmacological properties and permeation-enhancing ability. However, many [...] Read more.
Essential oils are natural products with a complex composition. Terpenes are the most common class of chemical compounds present in essential oils. Terpenes and the essential oils containing them are widely used and investigated by their pharmacological properties and permeation-enhancing ability. However, many terpenes and essential oils are sensitive to environmental conditions, undergoing volatilization and chemical degradation. In order to overcome the chemical instability of some isolated terpenes and essential oils, the encapsulation of these compounds in nanostructured systems (polymeric, lipidic, or molecular complexes) has been employed. In addition, nanoencapsulation can be of interest for pharmaceutical applications due to its capacity to improve the bioavailability and allow the controlled release of drugs. Topical drug administration is a convenient and non-invasive administration route for both local and systemic drug delivery. The present review focuses on describing the current status of research concerning nanostructured delivery systems containing isolated terpenes and/or essential oils designed for topical administration and on discussing the use of terpenes and essential oils either for their biological activities or as permeation enhancers in pharmaceutic formulations. Full article
(This article belongs to the Special Issue Evaluation and formulation of Bioactive Terpenes)
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Open AccessReview
A Review on Bioactivities of Tobacco Cembranoid Diterpenes
Biomolecules 2019, 9(1), 30; https://doi.org/10.3390/biom9010030 - 16 Jan 2019
Cited by 2
Abstract
Cembranoids are carbocyclic diterpenes comprising four isoprene units and are natural products with a parent skeleton consisting of a 14-membered ring. They have gained wide interest in recent years and are a major hotspot in the research of natural product chemistry. Since 1962, [...] Read more.
Cembranoids are carbocyclic diterpenes comprising four isoprene units and are natural products with a parent skeleton consisting of a 14-membered ring. They have gained wide interest in recent years and are a major hotspot in the research of natural product chemistry. Since 1962, various tobacco cembranoid diterpenes have been identified. This review systematically discusses and summarises the excellent antimicrobial, insecticidal, cytotoxic and neuroprotective activities of tobacco cembranoid diterpenes. These compounds show potential to be developed as botanical fungicides, cytotoxic drugs and drugs for the treatment of human immunodeficiency virus, Alzheimer’s disease, Parkinson’s disease, and other neurodegenerative diseases. However, there are relatively few studies on the structure–activity relationship (SAR) of tobacco cembranoid diterpenes. Therefore, future studies should focus on their structural modification, SAR and biogenic relationships. Full article
(This article belongs to the Special Issue Evaluation and formulation of Bioactive Terpenes)
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