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9.6
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Marine Drugs
Special Issues
Bioactive Marine Heterocyclic Compounds
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Bioactive Marine Heterocyclic Compounds

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

Deadline for manuscript submissions: closed (30 June 2020) | Viewed by 28272

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. Yoshihide Usami

E-Mail Website
Guest Editor
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Osaka Medical and Pharmaceutical University, Osaka, Japan
Interests: marine natural product; total synthesis; structural determination; bioactive; small molecule; azole
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Studies on heterocyclic compounds are important in drug discovery, since they show a variety of significant biological activities. Nitrogen-containing heterocyclic natural products, which are mainly found in plants, are called alkaloids. While it is true that terrestrial natural products, including alkaloids, have not had a main role in drug development throughout human history, recent progress in marine natural products has had a great impact in this field, which is something that all chemists are aware of. Marine-derived heterocyclic natural products increasingly look as if they are going to take the place of terrestrial products as seeds for new drugs. It is because of this that this Special Issue of Marine Drugs, “Bioactive Marine Heterocyclic Compounds” was proposed.

This Special issue aims to collect excellent original research articles and reviews focused on the isolation of new heterocyclic marine natural products, total synthesis, synthetic modification, or finding important bioactivities of known heterocyclic marine natural products. I hope this Special issue will affect new drug developments or innovation in the near future.

Prof. Dr. Yoshihide Usami
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.

Keywords

  • Marine natural product
  • Bioactive
  • Heterocyclic
  • Synthesis
  • Drug discovery

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Published Papers (7 papers)

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Research

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8 pages, 971 KiB  
Article
Agesasines A and B, Bromopyrrole Alkaloids from Marine Sponges Agelas spp
by Sanghoon Lee, Naonobu Tanaka, Sakura Takahashi, Daisuke Tsuji, Sang-Yong Kim, Mareshige Kojoma, Kohji Itoh, Jun’ichi Kobayashi and Yoshiki Kashiwada
Mar. Drugs 2020, 18(9), 455; https://doi.org/10.3390/md18090455 - 30 Aug 2020
Cited by 10 | Viewed by 2956
Abstract
Exploration for specialized metabolites of Okinawan marine sponges Agelas spp. resulted in the isolation of five new bromopyrrole alkaloids, agesasines A (1) and B (2), 9-hydroxydihydrodispacamide (3), 9-hydroxydihydrooroidin (4), and 9E-keramadine (5 [...] Read more.
Exploration for specialized metabolites of Okinawan marine sponges Agelas spp. resulted in the isolation of five new bromopyrrole alkaloids, agesasines A (1) and B (2), 9-hydroxydihydrodispacamide (3), 9-hydroxydihydrooroidin (4), and 9E-keramadine (5). Their structures were elucidated on the basis of spectroscopic analyses. Agesasines A (1) and B (2) were assigned as rare bromopyrrole alkaloids lacking an aminoimidazole moiety, while 3–5 were elucidated to be linear bromopyrrole alkaloids with either aminoimidazolone, aminoimidazole, or N-methylated aminoimidazole moieties. Full article
(This article belongs to the Special Issue Bioactive Marine Heterocyclic Compounds)
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17 pages, 1775 KiB  
Article
Synthesis and Antimicrobial Evaluation of Side-Chain Derivatives based on Eurotiumide A
by Atsushi Nakayama, Hideo Sato, Tenta Nakamura, Mai Hamada, Shuji Nagano, Shuhei Kameyama, Yui Furue, Naoki Hayashi, Go Kamoshida, Sangita Karanjit, Masataka Oda and Kosuke Namba
Mar. Drugs 2020, 18(2), 92; https://doi.org/10.3390/md18020092 - 30 Jan 2020
Cited by 3 | Viewed by 2978
Abstract
Side-chain derivatives of eurotiumide A, a dihydroisochroman-type natural product, have been synthesized and their antimicrobial activities described. Sixteen derivatives were synthesized from a key intermediate of the total synthesis of eurotiumide A, and their antimicrobial activities against two Gram-positive bacteria, methicillin-susceptible and methicillin-resistant [...] Read more.
Side-chain derivatives of eurotiumide A, a dihydroisochroman-type natural product, have been synthesized and their antimicrobial activities described. Sixteen derivatives were synthesized from a key intermediate of the total synthesis of eurotiumide A, and their antimicrobial activities against two Gram-positive bacteria, methicillin-susceptible and methicillin-resistant Staphylococcus aureus (MSSA and MRSA), and a Gram-negative bacterium, Porphyromonas gingivalis, were evaluated. The results showed that derivatives having an iodine atom on their aromatic ring instead of the prenyl moiety displayed better antimicrobial activity than eurotiumide A against MSSA and P. gingivalis. Moreover, we discovered that a derivative with an isopentyl side chain, which is a hydrogenated product of eurotiumide A, is the strongest antimicrobial agent against all three strains, including MRSA. Full article
(This article belongs to the Special Issue Bioactive Marine Heterocyclic Compounds)
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14 pages, 4009 KiB  
Article
Impact of the Cultivation Technique on the Production of Secondary Metabolites by Chrysosporium lobatum TM-237-S5, Isolated from the Sponge Acanthella cavernosa
by Géraldine Le Goff, Philippe Lopes, Guillaume Arcile, Pinelopi Vlachou, Elsa Van Elslande, Pascal Retailleau, Jean-François Gallard, Michal Weis, Yehuda Benayahu, Nikolas Fokialakis and Jamal Ouazzani
Mar. Drugs 2019, 17(12), 678; https://doi.org/10.3390/md17120678 - 30 Nov 2019
Cited by 10 | Viewed by 3283
Abstract
The fungi Chrysosporium lobatum TM-237-S5 was isolated from the sponge Acanthella cavernosa, collected from the mesophotic coral ecosystem of the Red Sea. The strain was cultivated on a potato dextrose agar (PDA) medium, coupling solid-state fermentation and solid-state extraction (SSF/SSE) with a [...] Read more.
The fungi Chrysosporium lobatum TM-237-S5 was isolated from the sponge Acanthella cavernosa, collected from the mesophotic coral ecosystem of the Red Sea. The strain was cultivated on a potato dextrose agar (PDA) medium, coupling solid-state fermentation and solid-state extraction (SSF/SSE) with a neutral macroreticular polymeric adsorbent XAD Amberlite resin (AMBERLITE XAD1600N). The SSF/SSE lead to high chemodiversity and productivity compared to classical submerged cultivation. Ten phenalenone related compounds were isolated and fully characterized by one-dimensional and two-dimensional NMR and HRMS. Among them, four were found to be new compounds corresponding to isoconiolactone, (-)-peniciphenalenin F, (+)-8-hydroxyscleroderodin, and (+)-8-hydroxysclerodin. It is concluded that SSF/SSE is a powerful strategy, opening a new era for the exploitation of microbial secondary metabolites. Full article
(This article belongs to the Special Issue Bioactive Marine Heterocyclic Compounds)
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11 pages, 1509 KiB  
Communication
Genome Sequencing of Streptomyces olivaceus SCSIO T05 and Activated Production of Lobophorin CR4 via Metabolic Engineering and Genome Mining
by Chunyan Zhang, Wenjuan Ding, Xiangjing Qin and Jianhua Ju
Mar. Drugs 2019, 17(10), 593; https://doi.org/10.3390/md17100593 - 20 Oct 2019
Cited by 19 | Viewed by 4340
Abstract
Marine-sourced actinomycete genus Streptomyces continues to be an important source of new natural products. Here we report the complete genome sequence of deep-sea-derived Streptomyces olivaceus SCSIO T05, harboring 37 putative biosynthetic gene clusters (BGCs). A cryptic BGC for type I polyketides was activated [...] Read more.
Marine-sourced actinomycete genus Streptomyces continues to be an important source of new natural products. Here we report the complete genome sequence of deep-sea-derived Streptomyces olivaceus SCSIO T05, harboring 37 putative biosynthetic gene clusters (BGCs). A cryptic BGC for type I polyketides was activated by metabolic engineering methods, enabling the discovery of a known compound, lobophorin CR4 (1). Genome mining yielded a putative lobophorin BGC (lbp) that missed the functional FAD-dependent oxidoreductase to generate the d-kijanose, leading to the production of lobophorin CR4 without the attachment of d-kijanose to C17-OH. Using the gene-disruption method, we confirmed that the lbp BGC accounts for lobophorin biosynthesis. We conclude that metabolic engineering and genome mining provide an effective approach to activate cryptic BGCs. Full article
(This article belongs to the Special Issue Bioactive Marine Heterocyclic Compounds)
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13 pages, 1735 KiB  
Article
Polyketides from the Mangrove-Derived Endophytic Fungus Cladosporium cladosporioides
by Fan-Zhong Zhang, Xiao-Ming Li, Xin Li, Sui-Qun Yang, Ling-Hong Meng and Bin-Gui Wang
Mar. Drugs 2019, 17(5), 296; https://doi.org/10.3390/md17050296 - 17 May 2019
Cited by 27 | Viewed by 4047
Abstract
Five new polyketides, namely, 5R-hydroxyrecifeiolide (1), 5S-hydroxyrecifeiolide (2), ent-cladospolide F (3), cladospolide G (4), and cladospolide H (5), along with two known compounds (6 and 7), [...] Read more.
Five new polyketides, namely, 5R-hydroxyrecifeiolide (1), 5S-hydroxyrecifeiolide (2), ent-cladospolide F (3), cladospolide G (4), and cladospolide H (5), along with two known compounds (6 and 7), were isolated from the endophytic fungal strain Cladosporium cladosporioides MA-299 that was obtained from the leaves of the mangrove plant Bruguiera gymnorrhiza. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, ECDs and optical rotations, and modified Mosher’s method. The structures of 3 and 6 were confirmed by single-crystal X-ray diffraction analysis and this is the first time for reporting the crystal structures of these two compounds. All of the isolated compounds were examined for antimicrobial activities against human and aquatic bacteria and plant pathogenic fungi as well as enzymatic inhibitory activities against acetylcholinesterase. Compounds 1–4, 6, and 7 exhibited antimicrobial activity against some of the tested strains with MIC values ranging from 1.0 to 64 μg/mL, while 3 exhibited enzymatic inhibitory activity against acetylcholinesterase with the IC50 value of 40.26 μM. Full article
(This article belongs to the Special Issue Bioactive Marine Heterocyclic Compounds)
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10 pages, 2251 KiB  
Article
Altercrasins A–E, Decalin Derivatives, from a Sea-Urchin-Derived Alternaria sp.: Isolation and Structural Analysis Including Stereochemistry
by Takeshi Yamada, Asumi Tanaka, Tatsuo Nehira, Takumi Nishii and Takashi Kikuchi
Mar. Drugs 2019, 17(4), 218; https://doi.org/10.3390/md17040218 - 11 Apr 2019
Cited by 14 | Viewed by 3759
Abstract
In order to find out the seeds of antitumor agents, we focused on potential bioactive materials from marine-derived microorganisms. Marine products include a number of compounds with unique structures, some of which may exhibit unusual bioactivities. As a part of this study, we [...] Read more.
In order to find out the seeds of antitumor agents, we focused on potential bioactive materials from marine-derived microorganisms. Marine products include a number of compounds with unique structures, some of which may exhibit unusual bioactivities. As a part of this study, we studied metabolites of a strain of Alternaria sp. OUPS-117D-1 originally derived from the sea urchin Anthocidaris crassispina, and isolated five new decalin derivatives, altercrasins A–E (1–5). The absolute stereostructure of altercrasins A (1) had been decided by chemical transformation and the modified Mosher’s method. In this study, four decalin derivatives, altercrasins B–E (2–5) were purified by silica gel chromatography, and reversed phase high-performance liquid chromatography (RP HPLC), and their structures were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic analyses. The absolute configuration of them were deduced by the comparison with 1 in the NMR chemical shifts, NOESY correlations, and electronic circular dichroism (ECD) spectral analyses. As a result, we found out that compound pairs of 1/2 and 4/5 were respective stereoisomers. In addition, their cytotoxic activities using murine P388 leukemia, human HL-60 leukemia, and murine L1210 leukemia cell lines showed that 4 and 5 exhibit potent cytotoxicity, in especially, the activity of 4 was equal to that of 5-fluorouracil. Full article
(This article belongs to the Special Issue Bioactive Marine Heterocyclic Compounds)
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Review

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43 pages, 6690 KiB  
Review
Natural Bioactive Thiazole-Based Peptides from Marine Resources: Structural and Pharmacological Aspects
by Rajiv Dahiya, Sunita Dahiya, Neeraj Kumar Fuloria, Suresh Kumar, Rita Mourya, Suresh V. Chennupati, Satish Jankie, Hemendra Gautam, Sunil Singh, Sanjay Kumar Karan, Sandeep Maharaj, Shivkanya Fuloria, Jyoti Shrivastava, Alka Agarwal, Shamjeet Singh, Awadh Kishor, Gunjan Jadon and Ajay Sharma
Mar. Drugs 2020, 18(6), 329; https://doi.org/10.3390/md18060329 - 24 Jun 2020
Cited by 39 | Viewed by 5973
Abstract
Peptides are distinctive biomacromolecules that demonstrate potential cytotoxicity and diversified bioactivities against a variety of microorganisms including bacteria, mycobacteria, and fungi via their unique mechanisms of action. Among broad-ranging pharmacologically active peptides, natural marine-originated thiazole-based oligopeptides possess peculiar structural features along with a [...] Read more.
Peptides are distinctive biomacromolecules that demonstrate potential cytotoxicity and diversified bioactivities against a variety of microorganisms including bacteria, mycobacteria, and fungi via their unique mechanisms of action. Among broad-ranging pharmacologically active peptides, natural marine-originated thiazole-based oligopeptides possess peculiar structural features along with a wide spectrum of exceptional and potent bioproperties. Because of their complex nature and size divergence, thiazole-based peptides (TBPs) bestow a pivotal chemical platform in drug discovery processes to generate competent scaffolds for regulating allosteric binding sites and peptide–peptide interactions. The present study dissertates on the natural reservoirs and exclusive structural components of marine-originated TBPs, with a special focus on their most pertinent pharmacological profiles, which may impart vital resources for the development of novel peptide-based therapeutic agents. Full article
(This article belongs to the Special Issue Bioactive Marine Heterocyclic Compounds)
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