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Special Issue "Terpenoids from Marine Organisms"

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (20 March 2019).

Special Issue Editors

Guest Editor
Ass. Prof. Efstathia Ioannou

Department of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, GR 15771, Athens, Greece
Website | E-Mail
Phone: +302107274913
Interests: marine natural products; microbial biotranformations; marine microorganisms
Guest Editor
Prof. Vassilios Roussis

Department of Pharmacognosy and Chemistry of Natural Products, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, GR 15771, Athens, Greece
E-Mail
Phone: +30210 7274 592
Fax: +30 210 7274 592
Interests: marine natural products; chemotaxonomy; chemical ecology

Special Issue Information

Dear Colleagues,

Marine natural products have enjoyed a renaissance in the past few years, displaying molecules that have been approved as drugs in the United States and the European Union, as well as a diverse array of compounds that are currently into clinical trials.

Terpenes, one of the most diverse classes of natural products produced by a variety of organisms, are vital for the life of most organisms, exerting metabolic control and mediating intra- and inter-species interactions. More than 40,000 individual terpenoids are known to exist in nature with new compounds being discovered every year.

Marine organisms produce a wide array of fascinating terpenoid structures distinguished by characteristic structural features. The biological and ecochemical functions of terpenes include chemical communication, pollination, chemical protection, growth regulation, among others, but even though numerous studies have been reported on this subject, the full spectrum of their ecological roles has not yet been fully clarified.

Potential challenges and future directions involved in the advancement of these promising natural compounds will be covered in the special issue, including isolation-structure elucidation of new molecules, metabolomic studies, evaluation of bioactivities, mechanisms of action, recent developments in their biosynthesis, total synthesis, semisynthesis and biotransformatiom, as well as pharmaceutical applications.

Assist. Prof. Efstathia Ioannou
Prof. Vassilios Roussis
Guest Editor

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 papers will be 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. Marine Drugs 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 2000 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

  • Terpenes

  • Bioactivity

  • Biosynthesis

  • Metabolomic studies

  • Synthesis

  • Biotransformations

  • Pharmaceutical applications

  • Ecological roles

Published Papers (9 papers)

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Research

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Open AccessArticle
Anverenes B–E, New Polyhalogenated Monoterpenes from the Antarctic Red Alga Plocamium cartilagineum
Mar. Drugs 2019, 17(4), 230; https://doi.org/10.3390/md17040230
Received: 21 March 2019 / Revised: 10 April 2019 / Accepted: 11 April 2019 / Published: 17 April 2019
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Abstract
The subtidal red alga Plocamium cartilagineum was collected from the Western Antarctic Peninsula during the 2011 and 2017 austral summers. Bulk collections from specific sites corresponded to chemogroups identified by Young et al. in 2013. One of the chemogroups yielded several known acyclic [...] Read more.
The subtidal red alga Plocamium cartilagineum was collected from the Western Antarctic Peninsula during the 2011 and 2017 austral summers. Bulk collections from specific sites corresponded to chemogroups identified by Young et al. in 2013. One of the chemogroups yielded several known acyclic halogenated monoterpenes (25) as well as undescribed compounds of the same class, anverenes B–D (68). Examination of another chemogroup yielded an undescribed cyclic halogenated monoterpene anverene E (9) as its major secondary metabolite. Elucidation of structures was achieved through one-dimensional (1D) and 2D nuclear magnetic resonance (NMR) spectroscopy and negative chemical ionization mass spectrometry. Compounds 19 show moderate cytotoxicity against cervical cancer (HeLa) cells. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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Open AccessArticle
New Furanocembranoids from Briareum violaceum
Mar. Drugs 2019, 17(4), 214; https://doi.org/10.3390/md17040214
Received: 17 February 2019 / Revised: 16 March 2019 / Accepted: 3 April 2019 / Published: 5 April 2019
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Abstract
Three new furanocembranoids—briaviodiol F (1) and briaviotriols A (2) and B (3)—along with a known analogue, briaviodiol A (4), were obtained from a cultured-type octocoral Briareum violaceum. The structures of cembranoids 13 [...] Read more.
Three new furanocembranoids—briaviodiol F (1) and briaviotriols A (2) and B (3)—along with a known analogue, briaviodiol A (4), were obtained from a cultured-type octocoral Briareum violaceum. The structures of cembranoids 13 were elucidated by using spectroscopic methods. In vitro study demonstrated that compounds 2 and 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW 264.7, a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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Open AccessArticle
UPLC–MS/MS Identification of Sterol Sulfates in Marine Diatoms
Mar. Drugs 2019, 17(1), 10; https://doi.org/10.3390/md17010010
Received: 2 December 2018 / Revised: 18 December 2018 / Accepted: 20 December 2018 / Published: 24 December 2018
Cited by 1 | PDF Full-text (1352 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Diatoms are unicellular eukaryotic organisms that play a key ecological and biogeochemical role in oceans as major primary producers. Recently, these microalgae have also attracted interest as a promising source of functional products with widespread relevance. Progress in the knowledge of cell and [...] Read more.
Diatoms are unicellular eukaryotic organisms that play a key ecological and biogeochemical role in oceans as major primary producers. Recently, these microalgae have also attracted interest as a promising source of functional products with widespread relevance. Progress in the knowledge of cell and molecular biology of diatoms is envisaged as a key step to understanding regulation of their life cycle in marine environments as well as facilitating their full and profitable exploitation by biotechnological platforms. Recently, we identified sterol sulfates (StS) as regulatory molecules of cell death in the diatom Skeletonema marinoi. As these compounds may have a general role in diatom physiology and chemical signals in aquatic systems, we investigated a suitable tool for their analysis in laboratory and field samples. Herein, we describe a sensitive, fast, and efficient ultra performance liquid chromatography–mass spectrometry (UPLC–MS) method for qualitative and quantitative analysis of StS from crude extract of diatoms and other microalgae. The method was applied to 13 different strains of our collection of marine protists. This first study suggested a species-specific distribution of StS and identified the sulfated derivatives of 24-methylene cholesterol and 24-methyl cholesterol as the most common members in diatoms. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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Open AccessArticle
Eutypellenoids A–C, New Pimarane Diterpenes from the Arctic Fungus Eutypella sp. D-1
Mar. Drugs 2018, 16(8), 284; https://doi.org/10.3390/md16080284
Received: 29 July 2018 / Revised: 12 August 2018 / Accepted: 14 August 2018 / Published: 16 August 2018
Cited by 3 | PDF Full-text (4225 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Three new pimarane diterpenes, eutypellenoids A–C (13), together with a known compound, eutypenoid C (4), were isolated from the culture extract of Eutypella sp. D-1 derived from the Arctic region. Compounds 13 possessed an uncommon [...] Read more.
Three new pimarane diterpenes, eutypellenoids A–C (13), together with a known compound, eutypenoid C (4), were isolated from the culture extract of Eutypella sp. D-1 derived from the Arctic region. Compounds 13 possessed an uncommon tetrahydrofuran-fused pimarane diterpene skeleton. The structures of all compounds were determined by detailed spectroscopic analysis, electronic circular dichroism (ECD) analysis, as well as a comparison with the literature data. Antibacterial, antifungal, and cytotoxic activities of these compounds were evaluated. Compound 2 displayed antibacterial activity against Staphylococcus aureus and Escherichia coli with MIC values of 8 and 8 μg/mL, respectively. Additionally, compound 2 showed antifungal activity against Candida parapsilosis, Candida albicans, Candida glabrata, and Candida tropicalis with MIC values of 8, 8, 16, and 32 μg/mL, respectively. Furthermore, compound 2 exhibited moderate cytotoxic activity against HCT-116 cell line with IC50 value of 3.7 μM. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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Open AccessArticle
New Cembranoids and a Biscembranoid Peroxide from the Soft Coral Sarcophyton cherbonnieri
Mar. Drugs 2018, 16(8), 276; https://doi.org/10.3390/md16080276
Received: 27 June 2018 / Revised: 24 July 2018 / Accepted: 31 July 2018 / Published: 6 August 2018
Cited by 5 | PDF Full-text (3348 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Six new cembranoids, cherbonolides A−E (15) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by [...] Read more.
Six new cembranoids, cherbonolides A−E (15) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by detailed spectroscopic analysis and chemical methods. Compound 6 was discovered to be the first example of a molecular skeleton formed from two cembranoids connected by a peroxide group. Compounds 17 were shown to have the ability of inhibiting the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophils. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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Open AccessCommunication
Asperversins A and B, Two Novel Meroterpenoids with an Unusual 5/6/6/6 Ring from the Marine-Derived Fungus Aspergillus versicolor
Mar. Drugs 2018, 16(6), 177; https://doi.org/10.3390/md16060177
Received: 17 April 2018 / Revised: 14 May 2018 / Accepted: 14 May 2018 / Published: 23 May 2018
Cited by 5 | PDF Full-text (2858 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Asperversins A (1) and B (2), two novel meroterpenoids featuring an uncommon 5/6/6/6 ring system, along with five new analogues (37) and a known compound asperdemin (8), were obtained from the marine-derived fungus [...] Read more.
Asperversins A (1) and B (2), two novel meroterpenoids featuring an uncommon 5/6/6/6 ring system, along with five new analogues (37) and a known compound asperdemin (8), were obtained from the marine-derived fungus Aspergillus versicolor. Their structures and absolute configurations were confirmed by extensive spectroscopic analyses, single-crystal X-ray diffraction studies, and electronic circular dichroism (ECD) calculation. All new compounds were tested for their acetylcholinesterase enzyme (AChE) inhibitory activities and cytotoxic activities, of which compound 7 displayed moderate inhibitory activity against the AChE with an IC50 value of 13.6 μM. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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Open AccessArticle
Anticancer Activity of Euplotin C, Isolated from the Marine Ciliate Euplotes crassus, Against Human Melanoma Cells
Mar. Drugs 2018, 16(5), 166; https://doi.org/10.3390/md16050166
Received: 24 April 2018 / Revised: 8 May 2018 / Accepted: 14 May 2018 / Published: 16 May 2018
Cited by 2 | PDF Full-text (12771 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Cutaneous melanoma is the most serious type of skin cancer, so new cytotoxic weapons against novel targets in melanoma are of great interest. Euplotin C (EC), a cytotoxic secondary metabolite of the marine ciliate Euplotes crassus, was evaluated in the present study [...] Read more.
Cutaneous melanoma is the most serious type of skin cancer, so new cytotoxic weapons against novel targets in melanoma are of great interest. Euplotin C (EC), a cytotoxic secondary metabolite of the marine ciliate Euplotes crassus, was evaluated in the present study on human cutaneous melanoma cells to explore its anti-melanoma activity and to gain more insight into its mechanism of action. EC exerted a marked cytotoxic effect against three different human melanoma cell lines (A375, 501Mel and MeWo) with a potency about 30-fold higher than that observed in non-cancer cells (HDFa cells). A pro-apoptotic activity and a decrease in melanoma cell migration by EC were also observed. At the molecular level, the inhibition of the Erk and Akt pathways, which control many aspects of melanoma aggressiveness, was shown. EC cytotoxicity was antagonized by dantrolene, a ryanodine receptor (RyR) antagonist, in a concentration-dependent manner. A role of RyR as a direct target of EC was also suggested by molecular modelling studies. In conclusion, our data provide the first evidence of the anti-melanoma activity of EC, suggesting it may be a promising new scaffold for the development of selective activators of RyR to be used for the treatment of melanoma and other cancer types. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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Review

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Open AccessReview
Triterpenoids in Echinoderms: Fundamental Differences in Diversity and Biosynthetic Pathways
Mar. Drugs 2019, 17(6), 352; https://doi.org/10.3390/md17060352
Received: 18 April 2019 / Revised: 30 May 2019 / Accepted: 4 June 2019 / Published: 13 June 2019
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Abstract
Echinoderms form a remarkable phylum of marine invertebrates that present specific chemical signatures unique in the animal kingdom. It is particularly the case for essential triterpenoids that evolved separately in each of the five echinoderm classes. Indeed, while most animals have Δ5 [...] Read more.
Echinoderms form a remarkable phylum of marine invertebrates that present specific chemical signatures unique in the animal kingdom. It is particularly the case for essential triterpenoids that evolved separately in each of the five echinoderm classes. Indeed, while most animals have Δ5-sterols, sea cucumbers (Holothuroidea) and sea stars (Asteroidea) also possess Δ7 and Δ9(11)-sterols, a characteristic not shared with brittle stars (Ophiuroidea), sea urchins (Echinoidea), and crinoids (Crinoidea). These particular Δ7 and Δ9(11) sterols emerged as a self-protection against membranolytic saponins that only sea cucumbers and sea stars produce as a defense mechanism. The diversity of saponins is large; several hundred molecules have been described in the two classes of these saponins (i.e., triterpenoid or steroid saponins). This review aims to highlight the diversity of triterpenoids in echinoderms by focusing on sterols and triterpenoid glycosides, but more importantly to provide an updated view of the biosynthesis of these molecules in echinoderms. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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Open AccessReview
Terpenoids from Marine Soft Coral of the Genus Lemnalia: Chemistry and Biological Activities
Mar. Drugs 2018, 16(9), 320; https://doi.org/10.3390/md16090320
Received: 2 August 2018 / Revised: 2 September 2018 / Accepted: 4 September 2018 / Published: 9 September 2018
Cited by 5 | PDF Full-text (3421 KB) | HTML Full-text | XML Full-text
Abstract
Lemnalia is one of the most widely-distributed marine soft coral in tropical oceans and is known to produce novel terpenoids with a broad spectrum of biological activities. This review provides the first comprehensive overview of terpenoids produced by soft coral Lemnalia since their [...] Read more.
Lemnalia is one of the most widely-distributed marine soft coral in tropical oceans and is known to produce novel terpenoids with a broad spectrum of biological activities. This review provides the first comprehensive overview of terpenoids produced by soft coral Lemnalia since their first discovery in 1974. Full article
(This article belongs to the Special Issue Terpenoids from Marine Organisms)
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