Aromatic Marine Natural Products: Chemistry and Bioactivity

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

Deadline for manuscript submissions: closed (30 June 2021) | Viewed by 17928

Special Issue Editors


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Guest Editor
Department of Organic Chemistry, Faculty of Marine and Environmental Sciences, University of Cadiz, Spain
Interests: marine natural products chemistry; isolation and structure elucidation; bioactivity; cytotoxic, antioxidant, anti-inflammatory compounds

E-Mail Website
Guest Editor
Department of Organic Chemistry, Faculty of Marine and Environmental Sciences, University of Cadiz, Cadiz, Spain
Interests: natural products; spectroscopic and spectrometric methods; bioactivity; synthetic methodology

Special Issue Information

Dear Colleagues,

Aromatic natural products encompass specialized metabolites of very different biosynthetic origins, including terpenoids, alkaloids, polyketides, and phenol-derived compounds, among others, which are produced by a great variety of organisms. In particular, marine organisms have been the source of aromatic metabolites with extraordinary chemical diversity, ranging from simple benzenoids to complex molecular structures exhibiting ring assemblages that may include halogens or other intriguing functional groups and be linked to moieties with multiple stereocenters. From a biological point of view, aromatic natural products may have a metabolic role and be involved in interactions among species, while in the biomedical field, aromatic derivatives have shown relevant significance in the development of new therapeutic agents. Further, advances in modern spectroscopic methods/tools, which allow the detection and characterization of small quantities of organic compounds (at nanomole-scale), open a new field to study the importance of aromatic natural products in the marine environment.

Thus, this Special Issue expects the submissions of recent studies, trends, and future perspectives in the research of aromatic natural products from marine sources. Contributions from different areas of multidisciplinary research are encouraged, covering the different classes of aromatic metabolites with particular focus on isolation, biological activities, and synthetic approaches. Comprehensive review papers will also be welcome.

Prof. Dr. Eva Zubía
Prof. Dr. María J. Ortega
Guest Editors

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Keywords

  • Benzenoids
  • Aromatic terpenoids
  • Aromatic polyketides
  • Aromatic alkaloids
  • Phenolic natural products
  • Isolation
  • Structure determination
  • Biological activity
  • Chemical modification
  • Synthetic methodology

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Published Papers (4 papers)

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Research

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18 pages, 1234 KiB  
Article
Ecological and Pharmacological Activities of Polybrominated Diphenyl Ethers (PBDEs) from the Indonesian Marine Sponge Lamellodysidea herbacea
by Muhammad R. Faisal, Matthias Y. Kellermann, Sven Rohde, Masteria Y. Putra, Tutik Murniasih, Chandra Risdian, Kathrin I. Mohr, Joachim Wink, Dimas F. Praditya, Eike Steinmann, Matthias Köck and Peter J. Schupp
Mar. Drugs 2021, 19(11), 611; https://doi.org/10.3390/md19110611 - 27 Oct 2021
Cited by 9 | Viewed by 2873
Abstract
Two known Polybrominated Diphenyl Ethers (PBDEs), 3,4,5-tribromo-2-(2′,4′-dibromophenoxy)phenol (1d) and 3,4,5,6-tetrabromo-2-(2′,4′-dibromophenoxy)phenol (2b), were isolated from the Indonesian marine sponge Lamellodysidea herbacea. The structure was confirmed using 13C chemical shift average deviation and was compared to the predicted structures [...] Read more.
Two known Polybrominated Diphenyl Ethers (PBDEs), 3,4,5-tribromo-2-(2′,4′-dibromophenoxy)phenol (1d) and 3,4,5,6-tetrabromo-2-(2′,4′-dibromophenoxy)phenol (2b), were isolated from the Indonesian marine sponge Lamellodysidea herbacea. The structure was confirmed using 13C chemical shift average deviation and was compared to the predicted structures and recorded chemical shifts in previous studies. We found a wide range of bioactivities from the organic crude extract, such as (1) a strong deterrence against the generalist pufferfish Canthigaster solandri, (2) potent inhibition against environmental and human pathogenic bacterial and fungal strains, and (3) the inhibition of the Hepatitis C Virus (HCV). The addition of a bromine atom into the A-ring of compound 2b resulted in higher fish feeding deterrence compared to compound 1d. On the contrary, compound 2b showed only more potent inhibition against the Gram-negative bacteria Rhodotorula glutinis (MIC 2.1 μg/mL), while compound 1d showed more powerful inhibition against the other human pathogenic bacteria and fungi. The first report of a chemical defense by compounds 1d and 2b against fish feeding and environmental relevant bacteria, especially pathogenic bacteria, might be one reason for the widespread occurrence of the shallow water sponge Lamellodysidea herbacea in Indonesia and the Indo-Pacific. Full article
(This article belongs to the Special Issue Aromatic Marine Natural Products: Chemistry and Bioactivity)
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10 pages, 598 KiB  
Article
Polyhydroxy p-Terphenyls from a Mangrove Endophytic Fungus Aspergillus candidus LDJ-5
by Guoliang Zhou, Xiaomin Zhang, Mudassir Shah, Qian Che, Guojian Zhang, Qianqun Gu, Tianjiao Zhu and Dehai Li
Mar. Drugs 2021, 19(2), 82; https://doi.org/10.3390/md19020082 - 2 Feb 2021
Cited by 11 | Viewed by 3220
Abstract
Six undescribed polyhydroxy p-terphenyls, namely asperterphenyllins A–F, were isolated from an endophytic fungus Aspergillus candidus LDJ-5. Their structures were determined by NMR and MS data. Differing from the previously reported p-terphenyls, asperterphenyllin A represents the first p-terphenyl dimer connected by [...] Read more.
Six undescribed polyhydroxy p-terphenyls, namely asperterphenyllins A–F, were isolated from an endophytic fungus Aspergillus candidus LDJ-5. Their structures were determined by NMR and MS data. Differing from the previously reported p-terphenyls, asperterphenyllin A represents the first p-terphenyl dimer connected by a C-C bond. Asperterphenyllin A displayed anti-influenza virus A (H1N1) activity and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC50 values of 53 μM and 21 μM, respectively. The anti-influenza virus A (H1N1) activity and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity of p-terphenyls are reported for the first time. Asperterphenyllin G exhibited cytotoxicity against nine cell lines with IC50 values ranging from 0.4 to 1.7 μM. Asperterphenyllin C showed antimicrobial activity against Proteus species with a MIC value of 19 μg/mL. Full article
(This article belongs to the Special Issue Aromatic Marine Natural Products: Chemistry and Bioactivity)
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10 pages, 962 KiB  
Article
Aromatic Polyketides from a Symbiotic Strain Aspergillus fumigatus D and Characterization of Their Biosynthetic Gene D8.t287
by Yi Hua, Rui Pan, Xuelian Bai, Bin Wei, Jianwei Chen, Hong Wang and Huawei Zhang
Mar. Drugs 2020, 18(6), 324; https://doi.org/10.3390/md18060324 - 20 Jun 2020
Cited by 13 | Viewed by 4522
Abstract
The chemical investigation of one symbiotic strain, Aspergillus fumigatus D, from the coastal plant Edgeworthia chrysantha Lindl led to the isolation of eight compounds (18), which were respectively identified as rubrofusarin B (1), alternariol 9-O-methyl [...] Read more.
The chemical investigation of one symbiotic strain, Aspergillus fumigatus D, from the coastal plant Edgeworthia chrysantha Lindl led to the isolation of eight compounds (18), which were respectively identified as rubrofusarin B (1), alternariol 9-O-methyl ether (2), fonsecinone D (3), asperpyrone A (4), asperpyrone D (5), fonsecinone B (6), fonsecinone A (7), and aurasperone A (8) by a combination of spectroscopic methods (1D NMR and ESI-MS) as well as by comparison with the literature data. An antimicrobial assay showed that these aromatic polyketides exhibited no remarkable inhibitory effect on Escherichia coli, Staphyloccocus aureus and Candida albicans. The genomic feature of strain D was analyzed, as well as its biosynthetic gene clusters, using antibiotics and Secondary Metabolite Analysis Shell 5.1.2 (antiSMASH). Plausible biosynthetic pathways for dimeric naphtho-γ-pyrones 38 were first proposed in this work. A non-reducing polyketide synthase (PKS) gene D8.t287 responsible for the biosynthesis of these aromatic polyketides 18 was identified and characterized by target gene knockout experiment and UPLC-MS analysis. Full article
(This article belongs to the Special Issue Aromatic Marine Natural Products: Chemistry and Bioactivity)
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Review

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25 pages, 5391 KiB  
Review
Naturally Occurring Oxazole-Containing Peptides
by Jessica T. Mhlongo, Edikarlos Brasil, Beatriz G. de la Torre and Fernando Albericio
Mar. Drugs 2020, 18(4), 203; https://doi.org/10.3390/md18040203 - 10 Apr 2020
Cited by 41 | Viewed by 6350
Abstract
Oxazole-containing peptides are mostly of marine origin and they form an intriguing family with a broad range of biological activities. Here we classify these peptides on the basis of their chemical structure and discuss a number of representatives of each class that reflect [...] Read more.
Oxazole-containing peptides are mostly of marine origin and they form an intriguing family with a broad range of biological activities. Here we classify these peptides on the basis of their chemical structure and discuss a number of representatives of each class that reflect the extraordinary potential of this family as a source of new drugs. Full article
(This article belongs to the Special Issue Aromatic Marine Natural Products: Chemistry and Bioactivity)
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