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Marine Drugs
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Natural Product from the Deep Sea
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Natural Product from the Deep Sea

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

Deadline for manuscript submissions: closed (30 October 2021) | Viewed by 21207

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

Special Issue Editor

Prof. Dr. Kazuo Umezawa

E-Mail Website
Guest Editor
Department of Molecular Target Medicine, Aichi Medical University, Nagakute, Japan
Interests: bioactive metabolite screening from micro-organisms and plants; cellular signal transduction; development of anti-inflammatory and anticancer agents
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Many scientists have tried to isolate novel and active compounds mainly from micro-organisms, including bacteria, Streptomyces, and fungi, plants, and ordinary marine organisms, since the middle of the 20th century. However, after the long history of screening, it is becoming more difficult to find novel compounds anywhere in the world.

Until now, more than 28,600 marine natural products have been reported. However, with the development on marine natural products research, the hit rate of new compounds is also decreasing. Scientists are turning their attention to the deep sea. By 2008, almost 400 compounds were isolated from deep-sea organisms. By 2013, a further 188 new deep-sea natural products were reported. About 75% of the deep-sea-origin compounds were reported to show biological activity (i.e., 141 of 188 compounds), with almost half (i.e., 81 of 188 compounds) exhibiting potent cytotoxicity in human cancer cell lines [Scropeta et al, 2014].

In addition to the micro-organisms, there are also sponges and corals in the deep sea. An investigation of the extracts of 65 twilight-zone (50–1000 m depth) sponges, gorgonians, hard corals, and sponge-associated bacteria resulted in an extremely high hit rate (42%) of active extracts, with a hit rate for sponge and gorgonian extracts of 72% [Schupp et al, 2009 and Wright et al 2012].

Therefore, deep-sea organisms are important sources of natural products, especially for screening of pharmacologically active compounds. In this Special Issue, I would like to bring together articles on the screening of both new chemicals and bioactive metabolites produced by deep-sea organisms. Articles concerning the timely synthesis and biotransformation of natural products from the deep sea are also welcome. This Special Issue “Natural Products from the Deep Sea” will be useful for the screening of pharmacologically active compounds from nature.

Prof. Dr. Kazuo Umezawa
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

  • natural products
  • deep-sea organisms
  • isolation
  • structure determination
  • synthesis
  • biotransformation
  • biological activities

Related Special Issues

Published Papers (8 papers)

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Research

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10 pages, 2117 KiB  
Article
Thioester-Containing Benzoate Derivatives with α-Glucosidase Inhibitory Activity from the Deep-Sea-Derived Fungus Talaromyces indigoticus FS688
by Mingqiong Li, Saini Li, Jinhua Hu, Xiaoxia Gao, Yanlin Wang, Zhaoming Liu and Weimin Zhang
Mar. Drugs 2022, 20(1), 33; https://doi.org/10.3390/md20010033 - 29 Dec 2021
Cited by 9 | Viewed by 1715
Abstract
Eurothiocins C–H (1–6), six unusual thioester-containing benzoate derivatives, were isolated from the deep-sea-derived fungus Talaromyces indigoticus FS688 together with a known analogue eurothiocin A (7). Their structures were elucidated through spectroscopic analysis and the absolute configurations were [...] Read more.
Eurothiocins C–H (1–6), six unusual thioester-containing benzoate derivatives, were isolated from the deep-sea-derived fungus Talaromyces indigoticus FS688 together with a known analogue eurothiocin A (7). Their structures were elucidated through spectroscopic analysis and the absolute configurations were determined by X-ray diffraction and ECD calculations. In addition, compound 1 exhibited significant inhibitory activity against α-glucosidase with an IC50 value of 5.4 μM, while compounds 4 and 5 showed moderate effects with IC50 values of 33.6 and 72.1 μM, respectively. A preliminary structure–activity relationship is discussed and a docking analysis was performed. Full article
(This article belongs to the Special Issue Natural Product from the Deep Sea)
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11 pages, 2582 KiB  
Article
Novel Harziane Diterpenes from Deep-Sea Sediment Fungus Trichoderma sp. SCSIOW21 and Their Potential Anti-Inflammatory Effects
by Hongxu Li, Xinyi Liu, Xiaofan Li, Zhangli Hu and Liyan Wang
Mar. Drugs 2021, 19(12), 689; https://0-doi-org.brum.beds.ac.uk/10.3390/md19120689 - 01 Dec 2021
Cited by 13 | Viewed by 2610
Abstract
Five undescribed harziane-type diterpene derivatives, namely harzianol K (1), harzianol L (4), harzianol M (5), harzianol N (6), harzianol O (7), along with two known compounds, hazianol J (2) and harzianol [...] Read more.
Five undescribed harziane-type diterpene derivatives, namely harzianol K (1), harzianol L (4), harzianol M (5), harzianol N (6), harzianol O (7), along with two known compounds, hazianol J (2) and harzianol A (3) were isolated from the deep-sea sediment-derived fungus Trichoderma sp. SCSIOW21. The relative configurations were determined by meticulous spectroscopic methods including 1D, 2D NMR spectroscopy, and HR-ESI-MS. The absolute configurations were established by the ECD curve calculations and the X-ray crystallographic analysis. These compounds (1, and 4–7) contributed to increasing the diversity of the caged harziane type diterpenes with highly congested skeleton characteristics. Harzianol J (2) exhibited a weak anti-inflammatory effect with 81.8% NO inhibition at 100 µM. Full article
(This article belongs to the Special Issue Natural Product from the Deep Sea)
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13 pages, 2281 KiB  
Article
Characteristics of Two Crustins from Alvinocaris longirostris in Hydrothermal Vents
by Lu-Lu Guo, Shao-Lu Wang, Fang-Chao Zhu, Feng Xue and Li-Sheng He
Mar. Drugs 2021, 19(11), 600; https://0-doi-org.brum.beds.ac.uk/10.3390/md19110600 - 22 Oct 2021
Cited by 3 | Viewed by 1608
Abstract
Crustins are widely distributed among different crustacean groups. They are characterized by a whey acidic protein (WAP) domain, and most examined Crustins show activity against Gram-positive bacteria. This study reports two Crustins, Al-crus 3 and Al-crus 7, from hydrothermal vent shrimp, Alvinocaris longirostris [...] Read more.
Crustins are widely distributed among different crustacean groups. They are characterized by a whey acidic protein (WAP) domain, and most examined Crustins show activity against Gram-positive bacteria. This study reports two Crustins, Al-crus 3 and Al-crus 7, from hydrothermal vent shrimp, Alvinocaris longirostris. Al-crus 3 and Al-crus 7 belong to Crustin Type IIa, with a similarity of about 51% at amino acid level. Antibacterial assays showed that Al-crus 3 mainly displayed activity against Gram-positive bacteria with MIC50 values of 10–25 μM. However, Al-crus 7 not only displayed activity against Gram-positive bacteria but also against Gram-negative bacteria Imipenem-resistant Acinetobacter baumannii, in a sensitive manner. Notably, in the effective antibacterial spectrum, Methicillin-sensitive Staphylococcus aureus, Escherichia coli (ESBLs) and Imipenem-resistant A. baumannii were drug-resistant pathogens. Narrowing down the sequence to the WAP domain, Al-crusWAP 3 and Al-crusWAP 7 demonstrated antibacterial activities but were weak. Additionally, the effects on bacteria did not significantly change after they were maintained at room temperature for 48 h. This indicated that Al-crus 3 and Al-crus 7 were relatively stable and convenient for transportation. Altogether, this study reported two new Crustins with specific characteristics. In particular, Al-crus 7 inhibited Gram-negative imipenem-resistant A. baumannii. Full article
(This article belongs to the Special Issue Natural Product from the Deep Sea)
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19 pages, 2477 KiB  
Article
Biotechnological and Ecological Potential of Micromonospora provocatoris sp. nov., a Gifted Strain Isolated from the Challenger Deep of the Mariana Trench
by Wael M. Abdel-Mageed, Lamya H. Al-Wahaibi, Burhan Lehri, Muneera S. M. Al-Saleem, Michael Goodfellow, Ali B. Kusuma, Imen Nouioui, Hariadi Soleh, Wasu Pathom-Aree, Marcel Jaspars and Andrey V. Karlyshev
Mar. Drugs 2021, 19(5), 243; https://0-doi-org.brum.beds.ac.uk/10.3390/md19050243 - 25 Apr 2021
Cited by 9 | Viewed by 4166
Abstract
A Micromonospora strain, isolate MT25T, was recovered from a sediment collected from the Challenger Deep of the Mariana Trench using a selective isolation procedure. The isolate produced two major metabolites, n-acetylglutaminyl glutamine amide and desferrioxamine B, the chemical structures of [...] Read more.
A Micromonospora strain, isolate MT25T, was recovered from a sediment collected from the Challenger Deep of the Mariana Trench using a selective isolation procedure. The isolate produced two major metabolites, n-acetylglutaminyl glutamine amide and desferrioxamine B, the chemical structures of which were determined using 1D and 2D-NMR, including 1H-15N HSQC and 1H-15N HMBC 2D-NMR, as well as high resolution MS. A whole genome sequence of the strain showed the presence of ten natural product-biosynthetic gene clusters, including one responsible for the biosynthesis of desferrioxamine B. Whilst 16S rRNA gene sequence analyses showed that the isolate was most closely related to the type strain of Micromonospora chalcea, a whole genome sequence analysis revealed it to be most closely related to Micromonospora tulbaghiae 45142T. The two strains were distinguished using a combination of genomic and phenotypic features. Based on these data, it is proposed that strain MT25T (NCIMB 15245T, TISTR 2834T) be classified as Micromonospora provocatoris sp. nov. Analysis of the genome sequence of strain MT25T (genome size 6.1 Mbp) revealed genes predicted to responsible for its adaptation to extreme environmental conditions that prevail in deep-sea sediments. Full article
(This article belongs to the Special Issue Natural Product from the Deep Sea)
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10 pages, 1833 KiB  
Article
New from Old: Thorectandrin Alkaloids in a Southern Australian Marine Sponge, Thorectandra choanoides (CMB-01889)
by Shamsunnahar Khushi, Angela A. Salim, Ahmed H. Elbanna, Laizuman Nahar and Robert J. Capon
Mar. Drugs 2021, 19(2), 97; https://0-doi-org.brum.beds.ac.uk/10.3390/md19020097 - 09 Feb 2021
Cited by 6 | Viewed by 2192
Abstract
Thorectandra choanoides (CMB-01889) was prioritized as a source of promising new chemistry from a library of 960 southern Australian marine sponge extracts, using a global natural products social (GNPS) molecular networking approach. The sponge was collected at a depth of 45 m. Chemical [...] Read more.
Thorectandra choanoides (CMB-01889) was prioritized as a source of promising new chemistry from a library of 960 southern Australian marine sponge extracts, using a global natural products social (GNPS) molecular networking approach. The sponge was collected at a depth of 45 m. Chemical fractionation followed by detailed spectroscopic analysis led to the discovery of a new tryptophan-derived alkaloid, thorectandrin A (1), with the GNPS cluster revealing a halo of related alkaloids 1a–1n. In considering biosynthetic origins, we propose that Thorectandrachoanoides (CMB-01889) produces four well-known alkaloids, 6-bromo-1′,8-dihydroaplysinopsin (2), 6-bromoaplysinopsin (3), aplysinopsin (4), and 1′,8-dihydroaplysinopsin (10), all of which are susceptible to processing by a putative indoleamine 2,3-dioxygenase-like (IDO) enzyme to 1a–1n. Where the 1′,8-dihydroalkaloids 2 and 10 are fully transformed to stable ring-opened thorectandrins 1 and 1a–1b, and 1h–1j, respectively, the conjugated precursors 3 and 4 are transformed to highly reactive Michael acceptors that during extraction and handling undergo complete transformation to artifacts 1c–1g, and 1k–1n, respectively. Knowledge of the susceptibility of aplysinopsins as substrates for IDOs, and the relative reactivity of Michael acceptor transformation products, informs our understanding of the pharmaceutical potential of this vintage marine pharmacophore. For example, the cancer tissue specificity of IDOs could be exploited for an immunotherapeutic response, with aplysinopsins transforming in situ to Michael acceptor thorectandrins, which covalently bind and inhibit the enzyme. Full article
(This article belongs to the Special Issue Natural Product from the Deep Sea)
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12 pages, 1767 KiB  
Article
Novel Macrolactams from a Deep-Sea-Derived Streptomyces Species
by Pei Wang, Dongyang Wang, Rongxin Zhang, Yi Wang, Fandong Kong, Peng Fu and Weiming Zhu
Mar. Drugs 2021, 19(1), 13; https://0-doi-org.brum.beds.ac.uk/10.3390/md19010013 - 29 Dec 2020
Cited by 14 | Viewed by 3116
Abstract
Four polyene macrolactams including the previously reported niizalactam C (4), and three new ones, streptolactams A–C (1–3) with a 26-membered monocyclic, [4,6,20]-fused tricyclic and 11,23-oxygen bridged [14,16]-bicyclic skeletons, respectively, were isolated from the fermentation broth of the [...] Read more.
Four polyene macrolactams including the previously reported niizalactam C (4), and three new ones, streptolactams A–C (1–3) with a 26-membered monocyclic, [4,6,20]-fused tricyclic and 11,23-oxygen bridged [14,16]-bicyclic skeletons, respectively, were isolated from the fermentation broth of the deep-sea sediment-derived Streptomyces sp. OUCMDZ-3159. Their structures were determined based on spectroscopic analysis, X-ray diffraction analysis, and chemical methods. The abiotic formation of compounds 2 and 4 from compound 1 were confirmed by a series of chemical reactions under heat and light conditions. Compounds 1 and 3 showed a selective antifungal activity against Candida albicans ATCC 10231. Full article
(This article belongs to the Special Issue Natural Product from the Deep Sea)
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10 pages, 1369 KiB  
Article
Isolation and Characterization of New Anti-Inflammatory and Antioxidant Components from Deep Marine-Derived Fungus Myrothecium sp. Bzo-l062
by Xiaojie Lu, Junjie He, Yanhua Wu, Na Du, Xiaofan Li, Jianhua Ju, Zhangli Hu, Kazuo Umezawa and Liyan Wang
Mar. Drugs 2020, 18(12), 597; https://0-doi-org.brum.beds.ac.uk/10.3390/md18120597 - 26 Nov 2020
Cited by 11 | Viewed by 2401
Abstract
In the present study, four new compounds including a pair of 2-benzoyl tetrahydrofuran enantiomers, namely, (−)-1S-myrothecol (1a) and (+)-1R-myrothecol (1b), a methoxy-myrothecol racemate (2), and an azaphilone derivative, myrothin (3), were [...] Read more.
In the present study, four new compounds including a pair of 2-benzoyl tetrahydrofuran enantiomers, namely, (−)-1S-myrothecol (1a) and (+)-1R-myrothecol (1b), a methoxy-myrothecol racemate (2), and an azaphilone derivative, myrothin (3), were isolated along with four known compounds (4–7) from cultures of the deep-sea fungus Myrothecium sp. BZO-L062. Enantiomeric compounds 1a and 1b were separated through normal-phase chiral high-performance liquid chromatography. The absolute configurations of 1a, 1b, and 3 were assigned by ECD spectra. Among them, the new compound 1a and its enantiomer 1b exhibited anti-inflammatory activity, inhibited nitric oxide formation in lipopolysaccharide-treated RAW264.7 cells, and exhibited antioxidant activity in the 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) and oxygen radical absorbance capacity assays. Full article
(This article belongs to the Special Issue Natural Product from the Deep Sea)
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Review

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15 pages, 1956 KiB  
Review
Cellular Signal Transductions and Their Inhibitors Derived from Deep-Sea Organisms
by Liyan Wang and Kazuo Umezawa
Mar. Drugs 2021, 19(4), 205; https://0-doi-org.brum.beds.ac.uk/10.3390/md19040205 - 05 Apr 2021
Cited by 3 | Viewed by 2330
Abstract
Not only physiological phenomena but also pathological phenomena can now be explained by the change of signal transduction in the cells of specific tissues. Commonly used cellular signal transductions are limited. They consist of the protein–tyrosine kinase dependent or independent Ras-ERK pathway, and [...] Read more.
Not only physiological phenomena but also pathological phenomena can now be explained by the change of signal transduction in the cells of specific tissues. Commonly used cellular signal transductions are limited. They consist of the protein–tyrosine kinase dependent or independent Ras-ERK pathway, and the PI3K-Akt, JAK-STAT, SMAD, and NF-κB-activation pathways. In addition, biodegradation systems, such as the ubiquitin–proteasome pathway and autophagy, are also important for physiological and pathological conditions. If we can control signaling for each by a low-molecular-weight agent, it would be possible to treat diseases in new ways. At present, such cell signaling inhibitors are mainly looked for in plants, soil microorganisms, and the chemical library. The screening of bioactive metabolites from deep-sea organisms should be valuable because of the high incidence of finding novel compounds. Although it is still an emerging field, there are many successful examples, with new cell signaling inhibitors. In this review, we would like to explain the current view of the cell signaling systems important in diseases, and show the inhibitors found from deep-sea organisms, with their structures and biological activities. These inhibitors are possible candidates for anti-inflammatory agents, modulators of metabolic syndromes, antimicrobial agents, and anticancer agents. Full article
(This article belongs to the Special Issue Natural Product from the Deep Sea)
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