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Pharmaceuticals
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Terpenes – Pharmaceutics and Biotechnology
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Terpenes – Pharmaceutics and Biotechnology

A special issue of Pharmaceuticals (ISSN 1424-8247). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (1 November 2021) | Viewed by 25189

Special Issue Editors

Dr. João C Fernandes

E-Mail Website
Guest Editor
CBQF—Centro de Biotecnologia e Química Fina – Laboratório Associado, Universidade Católica Portuguesa, Escola Superior de Biotecnologia, Porto, Portugal
Interests: natural products; cancer; inflammation; endoplasmic reticulum; proteostasis
Prof. Dr. David M. Pereira

E-Mail Website
Guest Editor
Laboratory of Pharmacognosy, Faculty of Pharmacy, University of Porto, Porto, Portugal
Interests: natural products chemistry; bioactive small molecules; anti-inflammatory drugs; pro-apoptotic drugs; endoplasmic reticulum stress; proteasome inhibitors
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In the ever-evolving field of pharmaceuticals, terpenes and its derivatives have been playing a remarkable role as effective therapeutic solutions, which include the antimalaric artemisinin, the anticancer drug paclitaxel, or the vaccine adjuvant squalene. This special issue will focus in the therapeutic application of terpenes and derivatives, and on their production using different biotechnological approaches.

The growing knowledge on the biological potential of terpenes and derivatives, driving new therapeutic strategies, is the focus of this Special Issue. The focus will be on research articles and reviews on sustainable approaches to produce terpenes, development and characterization of innovative formulations, on the stability and safety of terpene solutions, pharmacokinetic and pharmacodynamic profiles, and pharmacological investigation. Other technological or pharmaceutical aspects will also be welcome.

Dr. João Carlos Salvador Fernandes
Dr. David M. Pereira
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Pharmaceuticals is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Biotechnology
  • Terpenes
  • Pharmaceutics
  • Biosynthesis
  • Synthetic biology

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Published Papers (5 papers)

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Research

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14 pages, 4316 KiB  
Article
The Chemical Space of Terpenes: Insights from Data Science and AI
by Morteza Hosseini and David M. Pereira
Pharmaceuticals 2023, 16(2), 202; https://doi.org/10.3390/ph16020202 - 29 Jan 2023
Cited by 5 | Viewed by 3291
Abstract
Terpenes are a widespread class of natural products with significant chemical and biological diversity, and many of these molecules have already made their way into medicines. In this work, we employ a data science-based approach to identify, compile, and characterize the diversity of [...] Read more.
Terpenes are a widespread class of natural products with significant chemical and biological diversity, and many of these molecules have already made their way into medicines. In this work, we employ a data science-based approach to identify, compile, and characterize the diversity of terpenes currently known in a systematic way, in a total of 59,833 molecules. We also employed several methods for the purpose of classifying terpene subclasses using their physicochemical descriptors. Light gradient boosting machine, k-nearest neighbours, random forests, Gaussian naïve Bayes and Multilayer perceptron were tested, with the best-performing algorithms yielding accuracy, F1 score, precision and other metrics all over 0.9, thus showing the capabilities of these approaches for the classification of terpene subclasses. These results can be important for the field of phytochemistry and pharmacognosy, as they allow the prediction of the subclass of novel terpene molecules, even when biosynthetic studies are not available. Full article
(This article belongs to the Special Issue Terpenes – Pharmaceutics and Biotechnology)
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22 pages, 1344 KiB  
Article
Phytosterols and Novel Triterpenes Recovered from Industrial Fermentation Coproducts Exert In Vitro Anti-Inflammatory Activity in Macrophages
by Francisca S. Teixeira, Susana S. M. P. Vidigal, Lígia L. Pimentel, Paula T. Costa, Diana Tavares-Valente, João Azevedo-Silva, Manuela E. Pintado, João C. Fernandes and Luís M. Rodríguez-Alcalá
Pharmaceuticals 2021, 14(6), 583; https://doi.org/10.3390/ph14060583 - 18 Jun 2021
Cited by 12 | Viewed by 3328
Abstract
The unstoppable growth of human population that occurs in parallel with all manufacturing activities leads to a relentless increase in the demand for resources, cultivation land, and energy. In response, currently, there is significant interest in developing strategies to optimize any available resources [...] Read more.
The unstoppable growth of human population that occurs in parallel with all manufacturing activities leads to a relentless increase in the demand for resources, cultivation land, and energy. In response, currently, there is significant interest in developing strategies to optimize any available resources and their biowaste. While solutions initially focused on recovering biomolecules with applications in food, energy, or materials, the feasibility of synthetic biology in this field has been demonstrated in recent years. For instance, it is possible to genetically modify Saccharomyces cerevisiae to produce terpenes for commercial applications (i.e., against malaria or as biodiesel). But the production process, similar to any industrial activity, generates biowastes containing promising biomolecules (from fermentation) that if recovered may have applications in different areas. To test this hypothesis, in the present study, the lipid composition of by-products from the industrial production of β-farnesene by genetically modified Saccharomyces cerevisiae are studied to identify potentially bioactive compounds, their recovery, and finally, their stability and in vitro bioactivity. The assayed biowaste showed the presence of triterpenes, phytosterols, and 1-octacosanol which were recovered through molecular distillation into a single fraction. During the assayed stability test, compositional modifications were observed, mainly for the phytosterols and 1-octacosanol, probably due to oxidative reactions. However, such changes did not affect the in vitro bioactivity in macrophages, where it was found that the obtained fraction decreased the production of TNF-α and IL-6 in lipopolysaccharide (LPS)-induced inflammation. Full article
(This article belongs to the Special Issue Terpenes – Pharmaceutics and Biotechnology)
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12 pages, 1424 KiB  
Article
Methyl Jasmonate and Methyl-β-Cyclodextrin Individually Boost Triterpenoid Biosynthesis in Chlamydomonas Reinhardtii UVM4
by Audrey S. Commault, Unnikrishnan Kuzhiumparambil, Andrei Herdean, Michele Fabris, Ana Cristina Jaramillo-Madrid, Raffaela M. Abbriano, Peter J. Ralph and Mathieu Pernice
Pharmaceuticals 2021, 14(2), 125; https://doi.org/10.3390/ph14020125 - 5 Feb 2021
Cited by 6 | Viewed by 2961
Abstract
The commercialisation of valuable plant triterpenoids faces major challenges, including low abundance in natural hosts and costly downstream purification procedures. Endeavours to produce these compounds at industrial scale using microbial systems are gaining attention. Here, we report on a strategy to enrich the [...] Read more.
The commercialisation of valuable plant triterpenoids faces major challenges, including low abundance in natural hosts and costly downstream purification procedures. Endeavours to produce these compounds at industrial scale using microbial systems are gaining attention. Here, we report on a strategy to enrich the biomass of the biotechnologically-relevant Chlamydomonas reinhardtii strain UVM4 with valuable triterpenes, such as squalene and (S)-2,3-epoxysqualene. C. reinhardtii UVM4 was subjected to the elicitor compounds methyl jasmonate (MeJA) and methyl-β-cyclodextrine (MβCD) to increase triterpene yields. MeJA treatment triggered oxidative stress, arrested growth, and altered the photosynthetic activity of the cells, while increasing squalene, (S)-2,3-epoxysqualene, and cycloartenol contents. Applying MβCD to cultures of C. reinhardtii lead to the sequestration of the two main sterols (ergosterol and 7-dehydroporiferasterol) into the growth medium and the intracellular accumulation of the intermediate cycloartenol, without compromising cell growth. When MβCD was applied in combination with MeJA, it counteracted the negative effects of MeJA on cell growth and physiology, but no synergistic effect on triterpene yield was observed. Together, our findings provide strategies for the triterpene enrichment of microalgal biomass and medium. Full article
(This article belongs to the Special Issue Terpenes – Pharmaceutics and Biotechnology)
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19 pages, 1720 KiB  
Article
Overexpression of Key Sterol Pathway Enzymes in Two Model Marine Diatoms Alters Sterol Profiles in Phaeodactylum tricornutum
by Ana Cristina Jaramillo-Madrid, Raffaela Abbriano, Justin Ashworth, Michele Fabris, Mathieu Pernice and Peter J. Ralph
Pharmaceuticals 2020, 13(12), 481; https://doi.org/10.3390/ph13120481 - 21 Dec 2020
Cited by 14 | Viewed by 3785
Abstract
Sterols are a class of triterpenoid molecules with diverse functional roles in eukaryotic cells, including intracellular signaling and regulation of cell membrane fluidity. Diatoms are a dominant eukaryotic phytoplankton group that produce a wide diversity of sterol compounds. The enzymes 3-hydroxy-3-methyl glutaryl CoA [...] Read more.
Sterols are a class of triterpenoid molecules with diverse functional roles in eukaryotic cells, including intracellular signaling and regulation of cell membrane fluidity. Diatoms are a dominant eukaryotic phytoplankton group that produce a wide diversity of sterol compounds. The enzymes 3-hydroxy-3-methyl glutaryl CoA reductase (HMGR) and squalene epoxidase (SQE) have been reported to be rate-limiting steps in sterol biosynthesis in other model eukaryotes; however, the extent to which these enzymes regulate triterpenoid production in diatoms is not known. To probe the role of these two metabolic nodes in the regulation of sterol metabolic flux in diatoms, we independently over-expressed two versions of the native HMGR and a conventional, heterologous SQE gene in the diatoms Thalassiosira pseudonana and Phaeodactylum tricornutum. Overexpression of these key enzymes resulted in significant differential accumulation of downstream sterol pathway intermediates in P. tricornutum. HMGR-mVenus overexpression resulted in the accumulation of squalene, cycloartenol, and obtusifoliol, while cycloartenol and obtusifoliol accumulated in response to heterologous NoSQE-mVenus overexpression. In addition, accumulation of the end-point sterol 24-methylenecholesta-5,24(24’)-dien-3β-ol was observed in all P. tricornutum overexpression lines, and campesterol increased three-fold in P. tricornutum lines expressing NoSQE-mVenus. Minor differences in end-point sterol composition were also found in T. pseudonana, but no accumulation of sterol pathway intermediates was observed. Despite the successful manipulation of pathway intermediates and individual sterols in P. tricornutum, total sterol levels did not change significantly in transformed lines, suggesting the existence of tight pathway regulation to maintain total sterol content. Full article
(This article belongs to the Special Issue Terpenes – Pharmaceutics and Biotechnology)
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Review

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29 pages, 1399 KiB  
Review
Fermentation Strategies for Production of Pharmaceutical Terpenoids in Engineered Yeast
by Erdem Carsanba, Manuela Pintado and Carla Oliveira
Pharmaceuticals 2021, 14(4), 295; https://doi.org/10.3390/ph14040295 - 26 Mar 2021
Cited by 41 | Viewed by 11301
Abstract
Terpenoids, also known as isoprenoids, are a broad and diverse class of plant natural products with significant industrial and pharmaceutical importance. Many of these natural products have antitumor, anti-inflammatory, antibacterial, antiviral, and antimalarial effects, support transdermal absorption, prevent and treat cardiovascular diseases, and [...] Read more.
Terpenoids, also known as isoprenoids, are a broad and diverse class of plant natural products with significant industrial and pharmaceutical importance. Many of these natural products have antitumor, anti-inflammatory, antibacterial, antiviral, and antimalarial effects, support transdermal absorption, prevent and treat cardiovascular diseases, and have hypoglycemic activities. Production of these compounds are generally carried out through extraction from their natural sources or chemical synthesis. However, these processes are generally unsustainable, produce low yield, and result in wasting of substantial resources, most of them limited. Microbial production of terpenoids provides a sustainable and environment-friendly alternative. In recent years, the yeast Saccharomyces cerevisiae has become a suitable cell factory for industrial terpenoid biosynthesis due to developments in omics studies (genomics, transcriptomics, metabolomics, proteomics), and mathematical modeling. Besides that, fermentation development has a significant importance on achieving high titer, yield, and productivity (TYP) of these compounds. Up to now, there have been many studies and reviews reporting metabolic strategies for terpene biosynthesis. However, fermentation strategies have not been yet comprehensively discussed in the literature. This review summarizes recent studies of recombinant production of pharmaceutically important terpenoids by engineered yeast, S. cerevisiae, with special focus on fermentation strategies to increase TYP in order to meet industrial demands to feed the pharmaceutical market. Factors affecting recombinant terpenoids production are reviewed (strain design and fermentation parameters) and types of fermentation process (batch, fed-batch, and continuous) are discussed. Full article
(This article belongs to the Special Issue Terpenes – Pharmaceutics and Biotechnology)
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