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Marine Drugs
Special Issues
Bioactive Halogenated Metabolites of Marine Origin
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Bioactive Halogenated Metabolites of Marine Origin

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

Deadline for manuscript submissions: closed (30 June 2014) | Viewed by 85737

Special Issue Editor

Prof. Dr. Vassilios Roussis

E-Mail Website
Guest Editor
Department of Pharmacy, National and Kapodistrian University of Athens, 157 72 Athens, Greece
Interests: biomedical applications; electrospinning; nanofibers; hybrid materials; marine biopolymers
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Halogenated secondary metabolites, while rare in terrestrial plants, are common in marine organisms due to the abundance of chloride and bromide ions in seawater. Marine biota produce a variety of halogen containing organic compounds that have 1-30 carbon atoms. Organisms that have the ability to form halogenated compounds have been found among various species of algae, bacteria, sponges, mollusks, coelenterates and several marine worms.

Interestingly, bromine is the most commonly found halogen in marine natural products, even though its concentration in seawater is lower than that of chlorine. Of all marine organisms, algae possess the highest abundance of unique biosynthetic pathways for organohalogen production.

Seaweeds probably produce halogenated organics as part of a defense system against microorganism infections, herbivore grazing, space competitors, detrimental fouling by different kinds of epiphytes, or excess of self-generated hypochlorite and hydrogen peroxide. The chemotaxonomic value of these compounds has been seriously considered in the past but the geographic and seasonal variation in the chemical composition of algal species has reduced their importance.

A significant number of algal halogenated metabolites have exhibited an impressive array of biological properties ranging from antimicrobial to insecticidal activities.

Prof. Dr. Vassilios Roussis
Guest Editor

Submission

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. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as 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 refereed through a 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 1800 CHF (Swiss Francs).



Keywords

  • biosynthesis
  • structure elucidation
  • bioactivity
  • chemotaxonomy
  • chemical ecology
  • pharmacological activity

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Published Papers (6 papers)

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Research

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479 KiB  
Article
Antitumor and Antimicrobial Potential of Bromoditerpenes Isolated from the Red Alga, Sphaerococcus coronopifolius
by Daniel Rodrigues, Celso Alves, André Horta, Susete Pinteus, Joana Silva, Gérald Culioli, Olivier P. Thomas and Rui Pedrosa
Mar. Drugs 2015, 13(2), 713-726; https://doi.org/10.3390/md13020713 - 26 Jan 2015
Cited by 78 | Viewed by 10746
Abstract
Cancer and infectious diseases continue to be a major public health problem, and new drugs are necessary. As marine organisms are well known to provide a wide range of original compounds, the aim of this study was to investigate the bioactivity of the [...] Read more.
Cancer and infectious diseases continue to be a major public health problem, and new drugs are necessary. As marine organisms are well known to provide a wide range of original compounds, the aim of this study was to investigate the bioactivity of the main constituents of the cosmopolitan red alga, Sphaerococcus coronopifolius. The structure of several bromoditerpenes was determined by extensive spectroscopic analysis and comparison with literature data. Five molecules were isolated and characterized which include a new brominated diterpene belonging to the rare dactylomelane family and named sphaerodactylomelol (1), along with four already known sphaerane bromoditerpenes (2–5). Antitumor activity was assessed by cytotoxicity and anti-proliferative assays on an in vitro model of human hepatocellular carcinoma (HepG-2 cells). Antimicrobial activity was evaluated against four pathogenic microorganisms: Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Candida albicans. Compound 4 exhibited the highest antimicrobial activity against S. aureus (IC50 6.35 µM) and compound 5 the highest anti-proliferative activity on HepG-2 cells (IC50 42.9 µM). The new diterpene, sphaerodactylomelol (1), induced inhibition of cell proliferation (IC50 280 µM) and cytotoxicity (IC50 720 µM) on HepG-2 cells and showed antimicrobial activity against S. aureus (IC50 96.3 µM). Full article
(This article belongs to the Special Issue Bioactive Halogenated Metabolites of Marine Origin)
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1984 KiB  
Article
The Skeletal Amino Acid Composition of the Marine Demosponge Aplysina cavernicola
by Susanne Ueberlein, Susanne Machill, Hendrik Niemann, Peter Proksch and Eike Brunner
Mar. Drugs 2014, 12(8), 4417-4438; https://doi.org/10.3390/md12084417 - 8 Aug 2014
Cited by 11 | Viewed by 7595
Abstract
It has been discovered during the past few years that demosponges of the order Verongida such as Aplysina cavernicola exhibit chitin-based skeletons. Verongida sponges are well known to produce bioactive brominated tyrosine derivatives. We could recently demonstrate that brominated compounds do not exclusively [...] Read more.
It has been discovered during the past few years that demosponges of the order Verongida such as Aplysina cavernicola exhibit chitin-based skeletons. Verongida sponges are well known to produce bioactive brominated tyrosine derivatives. We could recently demonstrate that brominated compounds do not exclusively occur in the cellular matrix but also in the skeletons of the marine sponges Aplysina cavernicola and Ianthella basta. Our measurements imply that these yet unknown compounds are strongly, possibly covalently bound to the sponge skeletons. In the present work, we determined the skeletal amino acid composition of the demosponge A. cavernicola especially with respect to the presence of halogenated amino acids. The investigations of the skeletons before and after MeOH extraction confirmed that only a small amount of the brominated skeleton-bound compounds dissolves in MeOH. The main part of the brominated compounds is strongly attached to the skeletons but can be extracted for example by using Ba(OH)2. Various halogenated tyrosine derivatives were identified by GC-MS and LC-MS in these Ba(OH)2 extracts of the skeletons. Full article
(This article belongs to the Special Issue Bioactive Halogenated Metabolites of Marine Origin)
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178 KiB  
Article
Antibacterial Activities of a New Brominated Diterpene from Borneon Laurencia spp.
by Charles Santhanaraju Vairappan, Takahiro Ishii, Tan Kai Lee, Minoru Suzuki and Zhan Zhaoqi
Mar. Drugs 2010, 8(6), 1743-1749; https://doi.org/10.3390/md8061743 - 26 May 2010
Cited by 37 | Viewed by 9599
Abstract
In our continuous interest to study the diversity of halogenated metabolites of Malaysian species of the red algal genus Laurencia, we examined the chemical composition of five populations of unrecorded Laurencia sp. A new brominated diterpene, 10-acetoxyangasiol (1), and four [...] Read more.
In our continuous interest to study the diversity of halogenated metabolites of Malaysian species of the red algal genus Laurencia, we examined the chemical composition of five populations of unrecorded Laurencia sp. A new brominated diterpene, 10-acetoxyangasiol (1), and four other known metabolites, aplysidiol (2), cupalaurenol (3), 1-methyl-2,3,5-tribromoindole (4), and chamigrane epoxide (5), were isolated and identified. Isolated metabolites exhibited potent antibacterial activities against clinical bacteria, Staphylococcus aureus, Staphylococcus sp., Streptococcus pyogenes, Salmonella sp. and Vibrio cholerae. Full article
(This article belongs to the Special Issue Bioactive Halogenated Metabolites of Marine Origin)
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Review

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214 KiB  
Review
Halogenated Compounds from Marine Algae
by Maria Teresa Cabrita, Carlos Vale and Amélia Pilar Rauter
Mar. Drugs 2010, 8(8), 2301-2317; https://doi.org/10.3390/md8082301 - 9 Aug 2010
Cited by 228 | Viewed by 20518
Abstract
Marine algae produce a cocktail of halogenated metabolites with potential commercial value. Structures exhibited by these compounds go from acyclic entities with a linear chain to complex polycyclic molecules. Their medical and pharmaceutical application has been investigated for a few decades, however other [...] Read more.
Marine algae produce a cocktail of halogenated metabolites with potential commercial value. Structures exhibited by these compounds go from acyclic entities with a linear chain to complex polycyclic molecules. Their medical and pharmaceutical application has been investigated for a few decades, however other properties, such as antifouling, are not to be discarded. Many compounds were discovered in the last years, although the need for new drugs keeps this field open as many algal species are poorly screened. The ecological role of marine algal halogenated metabolites has somehow been overlooked. This new research field will provide valuable and novel insight into the marine ecosystem dynamics as well as a new approach to comprehending biodiversity. Furthermore, understanding interactions between halogenated compound production by algae and the environment, including anthropogenic or global climate changes, is a challenging target for the coming years. Research of halogenated metabolites has been more focused on macroalgae than on phytoplankton. However, phytoplankton could be a very promising material since it is the base of the marine food chain with quick adaptation to environmental changes, which undoubtedly has consequences on secondary metabolism. This paper reviews recent progress on this field and presents trends on the role of marine algae as producers of halogenated compounds. Full article
(This article belongs to the Special Issue Bioactive Halogenated Metabolites of Marine Origin)
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349 KiB  
Review
Halogenated Indole Alkaloids from Marine Invertebrates
by Patrícia Mendonça Pauletti, Lucas Silva Cintra, Caio Guedes Braguine, Ademar Alves da Silva Filho, Márcio Luís Andrade e Silva, Wilson Roberto Cunha and Ana Helena Januário
Mar. Drugs 2010, 8(5), 1526-1549; https://doi.org/10.3390/md8051526 - 28 Apr 2010
Cited by 83 | Viewed by 13301
Abstract
This review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates. Meridianins and related compounds (variolins, psammopemmins, and aplicyanins), as well as aplysinopsins and leptoclinidamines, are focused on. A compilation of the 13C-NMR spectral data [...] Read more.
This review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates. Meridianins and related compounds (variolins, psammopemmins, and aplicyanins), as well as aplysinopsins and leptoclinidamines, are focused on. A compilation of the 13C-NMR spectral data of these selected natural indole alkaloids is also provided. Full article
(This article belongs to the Special Issue Bioactive Halogenated Metabolites of Marine Origin)
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655 KiB  
Review
The Halogenated Metabolism of Brown Algae (Phaeophyta), Its Biological Importance and Its Environmental Significance
by Stéphane La Barre, Philippe Potin, Catherine Leblanc and Ludovic Delage
Mar. Drugs 2010, 8(4), 988-1010; https://doi.org/10.3390/md8040988 - 30 Mar 2010
Cited by 154 | Viewed by 22317
Abstract
Brown algae represent a major component of littoral and sublittoral zones in temperate and subtropical ecosystems. An essential adaptive feature of this independent eukaryotic lineage is the ability to couple oxidative reactions resulting from exposure to sunlight and air with the halogenations of [...] Read more.
Brown algae represent a major component of littoral and sublittoral zones in temperate and subtropical ecosystems. An essential adaptive feature of this independent eukaryotic lineage is the ability to couple oxidative reactions resulting from exposure to sunlight and air with the halogenations of various substrates, thereby addressing various biotic and abiotic stresses i.e., defense against predators, tissue repair, holdfast adhesion, and protection against reactive species generated by oxidative processes. Whereas marine organisms mainly make use of bromine to increase the biological activity of secondary metabolites, some orders of brown algae such as Laminariales have also developed a striking capability to accumulate and to use iodine in physiological adaptations to stress. We review selected aspects of the halogenated metabolism of macrophytic brown algae in the light of the most recent results, which point toward novel functions for iodide accumulation in kelps and the importance of bromination in cell wall modifications and adhesion properties of brown algal propagules. The importance of halogen speciation processes ranges from microbiology to biogeochemistry, through enzymology, cellular biology and ecotoxicology. Full article
(This article belongs to the Special Issue Bioactive Halogenated Metabolites of Marine Origin)
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