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Marine Drugs
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Marine Benzophenones and Xanthones: Isolation and Synthesis
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Marine Benzophenones and Xanthones: Isolation and Synthesis

A special issue of Marine Drugs (ISSN 1660-3397). This special issue belongs to the section "Synthesis and Medicinal Chemistry of Marine Natural Products".

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 14632

Special Issue Editor

Prof. Dr. Carlos Manuel Afonso

E-Mail Website
Guest Editor
1. Laboratório de Química Orgânica e Farmacêutica, Dep. Ciências Químicas, Faculdade de Farmácia da Universidade do Porto, Rua Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal
2. CIIMAR: Centro Interdisciplinar de Investigação Marinha e Ambiental da Universidade do Porto, Rua dos Bragas, 289, 4050-123 Porto, Portugal
Interests: medicinal chemistry; organic synthesis; pharmaceutical analysis; ADMET prediction; natural products
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Marine natural products are an important resource of structurally diverse small molecules with huge therapeutic potential. Xanthones and benzophenones are classic examples of secondary metabolites commonly isolated from marine sources, and many of them have shown a broad range of relevant bioactivities. As this area is still underexplored, there is a need to identify more members of these families and thoroughly evaluate their bioactivity and mode of action. In fact, we need a deeper understanding of the structural features that promote a given activity at the expense of others. To reach the goal of establishing structure–activity relationships, it is also relevant to identify robust and versatile synthetic methods to obtain these important scaffolds.

This Special Issue aims to collect contributions on the isolation of xanthones and benzophenones derived from marine organisms and disclosure of their biological activities. In addition, this Special Issue also aims to gather recent updates on the synthesis of marine xanthones or benzophenones and/or their analogues that can favor the applications of these marine metabolites.

Prof. Dr. Carlos Manuel Afonso
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 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. 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 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.

Published Papers (5 papers)

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Research

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17 pages, 5500 KiB  
Article
Natural Benzo/Acetophenones as Leads for New Synthetic Acetophenone Hybrids Containing a 1,2,3-Triazole Ring as Potential Antifouling Agents
by Ana Rita Neves, Daniela Pereira, Catarina Gonçalves, Joana Cardoso, Eugénia Pinto, Vitor Vasconcelos, Madalena Pinto, Emília Sousa, Joana R. Almeida, Honorina Cidade and Marta Correia-da-Silva
Mar. Drugs 2021, 19(12), 682; https://doi.org/10.3390/md19120682 - 29 Nov 2021
Cited by 8 | Viewed by 3034
Abstract
Marine biofouling is a natural process that represents major economic, environmental, and health concerns. Some booster biocides have been used in biofouling control, however, they were found to accumulate in environmental compartments, showing negative effects on marine organisms. Therefore, it is urgent to [...] Read more.
Marine biofouling is a natural process that represents major economic, environmental, and health concerns. Some booster biocides have been used in biofouling control, however, they were found to accumulate in environmental compartments, showing negative effects on marine organisms. Therefore, it is urgent to develop new eco-friendly alternatives. Phenyl ketones, such as benzophenones and acetophenones, have been described as modulators of several biological activities, including antifouling activity (AF). In this work, acetophenones were combined with other chemical substrates through a 1,2,3-triazole ring, a strategy commonly used in Medicinal Chemistry. In our approach, a library of 14 new acetophenone–triazole hybrids was obtained through the copper(I)-catalyzed alkyne-azide cycloaddition “click” reaction. All of the synthesized compounds were evaluated against the settlement of a representative macrofouling species, Mytilus galloprovincialis, as well as on biofilm-forming marine microorganisms, including bacteria and fungi. The growth of the microalgae Navicula sp. was also evaluated after exposure to the most promising compounds. While compounds 6a, 7a, and 9a caused significant inhibition of the settlement of mussel larvae, compounds 3b, 4b, and 7b were able to inhibit Roseobacter litoralis bacterial biofilm growth. Interestingly, acetophenone 7a displayed activity against both mussel larvae and the microalgae Navicula sp., suggesting a complementary action of this compound against macro- and microfouling species. The most potent compounds (6a, 7a, and 9a) also showed to be less toxic to the non-target species Artemia salina than the biocide Econea®. Regarding both AF potency and ecotoxicity activity evaluation, acetophenones 7a and 9a were put forward in this work as promising eco-friendly AF agents. Full article
(This article belongs to the Special Issue Marine Benzophenones and Xanthones: Isolation and Synthesis)
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16 pages, 2316 KiB  
Article
From Natural Xanthones to Synthetic C-1 Aminated 3,4-Dioxygenated Xanthones as Optimized Antifouling Agents
by Diana I. S. P. Resende, Joana R. Almeida, Sandra Pereira, Alexandre Campos, Agostinho Lemos, Jeffrey E. Plowman, Ancy Thomas, Stefan Clerens, Vitor Vasconcelos, Madalena Pinto, Marta Correia-da-Silva and Emília Sousa
Mar. Drugs 2021, 19(11), 638; https://doi.org/10.3390/md19110638 - 13 Nov 2021
Cited by 6 | Viewed by 2290
Abstract
Biofouling, which occurs when certain marine species attach and accumulate in artificial submerged structures, represents a serious economic and environmental issue worldwide. The discovery of new non-toxic and eco-friendly antifouling systems to control or prevent biofouling is, therefore, a practical and urgent need. [...] Read more.
Biofouling, which occurs when certain marine species attach and accumulate in artificial submerged structures, represents a serious economic and environmental issue worldwide. The discovery of new non-toxic and eco-friendly antifouling systems to control or prevent biofouling is, therefore, a practical and urgent need. In this work, the antifouling activity of a series of 24 xanthones, with chemical similarities to natural products, was exploited. Nine (1, 2, 4, 6, 8, 16, 19, 21, and 23) of the tested xanthones presented highly significant anti-settlement responses at 50 μM against the settlement of mussel Mytilus galloprovincialis larvae and low toxicity to this macrofouling species. Xanthones 21 and 23 emerged as the most effective larval settlement inhibitors (EC50 = 7.28 and 3.57 µM, respectively). Additionally, xanthone 23 exhibited a therapeutic ratio (LC50/EC50) > 15, as required by the US Navy program attesting its suitability as natural antifouling agents. From the nine tested xanthones, none of the compounds were found to significantly inhibit the growth of the marine biofilm-forming bacterial strains tested. Xanthones 4, 6, 8, 16, 19, 21, and 23 were found to be non-toxic to the marine non-target species Artemia salina (<10% mortality at 50 μM). Insights on the antifouling mode of action of the hit xanthones 21 and 23 suggest that these two compounds affected similar molecular targets and cellular processes in mussel larvae, including that related to mussel adhesion capacity. This work exposes for the first time the relevance of C-1 aminated xanthones with a 3,4-dioxygenated pattern of substitution as new non-toxic products to prevent marine biofouling. Full article
(This article belongs to the Special Issue Marine Benzophenones and Xanthones: Isolation and Synthesis)
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17 pages, 5869 KiB  
Article
Metabolites from Marine-Derived Fungi as Potential Antimicrobial Adjuvants
by Fernando Durães, Nikoletta Szemerédi, Decha Kumla, Madalena Pinto, Anake Kijjoa, Gabriella Spengler and Emília Sousa
Mar. Drugs 2021, 19(9), 475; https://doi.org/10.3390/md19090475 - 25 Aug 2021
Cited by 16 | Viewed by 3674
Abstract
Marine-derived fungi constitute an interesting source of bioactive compounds, several of which exhibit antibacterial activity. These acquire special importance, considering that antimicrobial resistance is becoming more widespread. The overexpression of efflux pumps, capable of expelling antimicrobials out of bacterial cells, is one of [...] Read more.
Marine-derived fungi constitute an interesting source of bioactive compounds, several of which exhibit antibacterial activity. These acquire special importance, considering that antimicrobial resistance is becoming more widespread. The overexpression of efflux pumps, capable of expelling antimicrobials out of bacterial cells, is one of the most worrisome mechanisms. There has been an ongoing effort to find not only new antimicrobials, but also compounds that can block resistance mechanisms which can be used in combination with approved antimicrobial drugs. In this work, a library of nineteen marine natural products, isolated from marine-derived fungi of the genera Neosartorya and Aspergillus, was evaluated for their potential as bacterial efflux pump inhibitors as well as the antimicrobial-related mechanisms, such as inhibition of biofilm formation and quorum-sensing. Docking studies were performed to predict their efflux pump action. These compounds were also tested for their cytotoxicity in mouse fibroblast cell line NIH/3T3. The results obtained suggest that the marine-derived fungal metabolites are a promising source of compounds with potential to revert antimicrobial resistance and serve as an inspiration for the synthesis of new antimicrobial drugs. Full article
(This article belongs to the Special Issue Marine Benzophenones and Xanthones: Isolation and Synthesis)
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Review

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20 pages, 1881 KiB  
Review
Marine-Derived Xanthone from 2010 to 2021: Isolation, Bioactivities and Total Synthesis
by Ana C. S. Veríssimo, Diana C. G. A. Pinto and Artur M. S. Silva
Mar. Drugs 2022, 20(6), 347; https://doi.org/10.3390/md20060347 - 25 May 2022
Cited by 7 | Viewed by 1855
Abstract
Marine life has proved to be an invaluable source of new compounds with significant bioactivities, such as xanthones. This review summarizes the advances made in the study of marine-derived xanthones from 2010 to 2021, from isolation towards synthesis, highlighting their biological activities. Most [...] Read more.
Marine life has proved to be an invaluable source of new compounds with significant bioactivities, such as xanthones. This review summarizes the advances made in the study of marine-derived xanthones from 2010 to 2021, from isolation towards synthesis, highlighting their biological activities. Most of these compounds were isolated from marine-derived fungi, found in marine sediments, and associated with other aquatic organisms (sponge and jellyfish). Once isolated, xanthones have been assessed for different bioactivities, such as antibacterial, antifungal, and cytotoxic properties. In the latter case, promising results have been demonstrated. Considering the significant bioactivities showed by xanthones, efforts have been made to synthesize these compounds, like yicathins B and C and the secalonic acid D, through total synthesis. Full article
(This article belongs to the Special Issue Marine Benzophenones and Xanthones: Isolation and Synthesis)
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36 pages, 5377 KiB  
Review
Bioactive Marine Xanthones: A Review
by José X. Soares, Daniela R. P. Loureiro, Ana Laura Dias, Salete Reis, Madalena M. M. Pinto and Carlos M. M. Afonso
Mar. Drugs 2022, 20(1), 58; https://doi.org/10.3390/md20010058 - 08 Jan 2022
Cited by 22 | Viewed by 2983
Abstract
The marine environment is an important source of specialized metabolites with valuable biological activities. Xanthones are a relevant chemical class of specialized metabolites found in this environment due to their structural variety and their biological activities. In this work, a comprehensive literature review [...] Read more.
The marine environment is an important source of specialized metabolites with valuable biological activities. Xanthones are a relevant chemical class of specialized metabolites found in this environment due to their structural variety and their biological activities. In this work, a comprehensive literature review of marine xanthones reported up to now was performed. A large number of bioactive xanthone derivatives (169) were identified, and their structures, biological activities, and natural sources were described. To characterize the chemical space occupied by marine-derived xanthones, molecular descriptors were calculated. For the analysis of the molecular descriptors, the xanthone derivatives were grouped into five structural categories (simple, prenylated, O-heterocyclic, complex, and hydroxanthones) and six biological activities (antitumor, antibacterial, antidiabetic, antifungal, antiviral, and miscellaneous). Moreover, the natural product-likeness and the drug-likeness of marine xanthones were also assessed. Marine xanthone derivatives are rewarding bioactive compounds and constitute a promising starting point for the design of other novel bioactive molecules. Full article
(This article belongs to the Special Issue Marine Benzophenones and Xanthones: Isolation and Synthesis)
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