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Marine Drugs
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Deep-Sea Natural Products II
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Deep-Sea Natural Products II

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

Deadline for manuscript submissions: closed (31 January 2020) | Viewed by 35220

Special Issue Editor

Dr. Olivier P. Thomas

E-Mail Website
Guest Editor
School of Biological and Chemical Sciences, Ryan Institute, University of Galway, Arts and Science Building, University Road, H91 TK33 Galway, Ireland
Interests: marine natural products; invertebrates; marine biodiscovery; marine chemical ecology; biosynthesis; metabolomics
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Until now, marine biodiscovery has been principally restricted to easily accessible marine areas. First, the intertidal environments of the oceans have been investigated and, with the development of SCUBA diving in the 1950s, access to the subtidal region to 50 to 60 m depth has been greatly facilitated. Recent years have witnessed several technological advances in (a) SCUBA diving with gas mixes; (b) the development of deep-submergence vehicles (DSV); or, more and more frequently today, (c) underwater remote operated vehicles (ROV). Today, all these techniques allow for the unveiling of fantastic marine biodiversity that was only described through trawling.

Associated with this largely unknown biodiversity, an untapped reservoir of biomolecules has to be uncovered. In this Special Issue, we aim to gather the most recent and promising findings in the structure elucidation of new metabolites isolated from deep-sea organisms, either macro- or micro-. Known metabolites isolated from the deep-sea but with new bioactivities will also be welcome, as well as side studies related to deep-sea natural products like those using dereplication and metabolomics approaches, or those focusing on the description of particular metabolic pathways.

Prof. Olivier P. Thomas
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 products
  • bioactive compounds
  • structure elucidation
  • metabolites
  • deep-sea
  • extreme environments

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Related Special Issue

Published Papers (9 papers)

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Research

14 pages, 3993 KiB  
Article
Mineral-Enriched Deep-Sea Water Modulates Lactate Metabolism via PGC-1α-Mediated Metabolic Reprogramming
by Byung Geun Ha, Sung Suk Jung, You Kyung Jang, Byong Yeob Jeon and Yun Hee Shon
Mar. Drugs 2019, 17(11), 611; https://doi.org/10.3390/md17110611 - 27 Oct 2019
Cited by 5 | Viewed by 3635
Abstract
Metabolic disorders such as diabetes and obesity are serious global health issues. These diseases are accelerated by mineral deficiencies, emphasizing the importance of addressing these deficiencies in disease management plans. Lactate metabolism is fundamentally linked to glucose metabolism, and several clinical studies have [...] Read more.
Metabolic disorders such as diabetes and obesity are serious global health issues. These diseases are accelerated by mineral deficiencies, emphasizing the importance of addressing these deficiencies in disease management plans. Lactate metabolism is fundamentally linked to glucose metabolism, and several clinical studies have reported that blood lactate levels are higher in obese and diabetic patients than in healthy subjects. Balanced deep-sea water contains various minerals and exhibits antiobesity and antidiabetic activities in mice; however, the impact of balanced deep-sea water on lactate metabolism is unclear. Thus, we evaluated the effects of balanced deep-sea water on lactate metabolism in C2C12 myotubes, and found that balanced deep-sea water mediated lactate metabolism by regulating the gene expression levels of lactate dehydrogenases A and B, a monocarboxylate transporter, and a mitochondrial pyruvate carrier. The activities of peroxisome proliferator-activated receptor gamma coactivator-1α (PGC-1α) and signaling molecules involved in PGC-1α activation were also upregulated by treatment with balanced deep-sea water. These results suggest that balanced deep-sea water, which can mediate lactate metabolism, may be used to prevent or treat obesity and diabetes mellitus. Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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12 pages, 2055 KiB  
Article
Antimicrobial Sesquiterpenoid Derivatives and Monoterpenoids from the Deep-Sea Sediment-Derived Fungus Aspergillus versicolor SD-330
by Xiao-Dong Li, Xiao-Ming Li, Xiu-Li Yin, Xin Li and Bin-Gui Wang
Mar. Drugs 2019, 17(10), 563; https://doi.org/10.3390/md17100563 - 29 Sep 2019
Cited by 30 | Viewed by 3598
Abstract
Two new antimicrobial bisabolane-type sesquiterpenoid derivatives, ent-aspergoterpenin C (compound 1) and 7-O-methylhydroxysydonic acid (2), and two new butyrolactone-type monoterpenoids, pestalotiolactones C (3) and D (4), along with a known monoterpenoid pestalotiolactone A ( [...] Read more.
Two new antimicrobial bisabolane-type sesquiterpenoid derivatives, ent-aspergoterpenin C (compound 1) and 7-O-methylhydroxysydonic acid (2), and two new butyrolactone-type monoterpenoids, pestalotiolactones C (3) and D (4), along with a known monoterpenoid pestalotiolactone A (5) and four known bisabolane sesquiterpenoids (6−9), were isolated and identified from the deep-sea sediment-derived fungus Aspergillus versicolor SD-330. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the absolute configurations of the new compounds 1−4 were determined by the combination of NOESY and TDDFT-ECD calculations and X-ray crystallographic analysis. Additionally, we first determined and reported the absolute configuration of the known monoterpenoid pestalotiolactone A (5) through the X-ray crystallographic experiment. All of these isolated compounds were evaluated for antimicrobial activities against human and aquatic pathogenic bacteria. Compounds 1, 2, 6 and 9 exhibited selective inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli, Edwardsiella tarda, Vibrio anguillarum and V. harveyi, with MIC values ranging from 1.0 to 8.0 μg/mL. Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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11 pages, 2617 KiB  
Article
Characterization of the Noncanonical Regulatory and Transporter Genes in Atratumycin Biosynthesis and Production in a Heterologous Host
by Zhijie Yang, Xin Wei, Jianqiao He, Changli Sun, Jianhua Ju and Junying Ma
Mar. Drugs 2019, 17(10), 560; https://doi.org/10.3390/md17100560 - 29 Sep 2019
Cited by 18 | Viewed by 3888
Abstract
Atratumycin is a cyclodepsipeptide with activity against Mycobacteria tuberculosis isolated from deep-sea derived Streptomyces atratus SCSIO ZH16NS-80S. Analysis of the atratumycin biosynthetic gene cluster (atr) revealed that its biosynthesis is regulated by multiple factors, including two LuxR regulatory genes (atr1 [...] Read more.
Atratumycin is a cyclodepsipeptide with activity against Mycobacteria tuberculosis isolated from deep-sea derived Streptomyces atratus SCSIO ZH16NS-80S. Analysis of the atratumycin biosynthetic gene cluster (atr) revealed that its biosynthesis is regulated by multiple factors, including two LuxR regulatory genes (atr1 and atr2), two ABC transporter genes (atr29 and atr30) and one Streptomyces antibiotic regulatory gene (atr32). In this work, three regulatory and two transporter genes were unambiguously determined to provide positive, negative and self-protective roles during biosynthesis of atratumycin through bioinformatic analyses, gene inactivations and trans-complementation studies. Notably, an unusual Streptomyces antibiotic regulatory protein Atr32 was characterized as a negative regulator; the function of Atr32 is distinct from previous studies. Five over-expression mutant strains were constructed by rational application of the regulatory and transporter genes; the resulting strains produced significantly improved titers of atratumycin that were ca. 1.7–2.3 fold greater than wild-type (WT) producer. Furthermore, the atratumycin gene cluster was successfully expressed in Streptomyces coelicolor M1154, thus paving the way for the transfer and recombination of large DNA fragments. Overall, this finding sets the stage for understanding the unique biosynthesis of pharmaceutically important atratumycin and lays the foundation for generating anti-tuberculosis lead compounds possessing novel structures. Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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11 pages, 922 KiB  
Article
Two New Cytotoxic Compounds from a Deep-Sea Penicillum citreonigrum XT20-134
by Xi-Xiang Tang, Shun-Zhi Liu, Xia Yan, Bo-Wen Tang, Mei-Juan Fang, Xiu-Min Wang, Zhen Wu and Ying-Kun Qiu
Mar. Drugs 2019, 17(9), 509; https://doi.org/10.3390/md17090509 - 29 Aug 2019
Cited by 22 | Viewed by 3599
Abstract
Penicillum citreonigrum XT20-134 (MCCC 3A00956) is a fungus with cytotoxic activity, derived from deep-sea sediment. Five new compounds, adeninylpyrenocine (1), 2-hydroxyl-3-pyrenocine-thio propanoic acid (2), ozazino-cyclo-(2,3-dihydroxyl-trp-tyr) (3), 5,5-dichloro-1-(3,5-dimethoxyphenyl)-1,4-dihydroxypentan-2-one (4), and 2,3,4-trihydroxybutyl cinnamate (5 [...] Read more.
Penicillum citreonigrum XT20-134 (MCCC 3A00956) is a fungus with cytotoxic activity, derived from deep-sea sediment. Five new compounds, adeninylpyrenocine (1), 2-hydroxyl-3-pyrenocine-thio propanoic acid (2), ozazino-cyclo-(2,3-dihydroxyl-trp-tyr) (3), 5,5-dichloro-1-(3,5-dimethoxyphenyl)-1,4-dihydroxypentan-2-one (4), and 2,3,4-trihydroxybutyl cinnamate (5), together with 19 known compounds (6–24), were isolated from an ethyl acetate (EtOAc) extract of its fermentation. The structures of the new compounds were comprehensively characterized by high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). All isolates were evaluated for their cytotoxic activities. The heteroatom-containing new compounds 2 and 4 showed potent cytotoxicity to the human hepatoma tumor cell Bel7402 with IC50 values of 7.63 ± 1.46, 13.14 ± 1.41 μM and the human fibrosarcoma tumor cell HT1080 with IC50 values of 10.22 ± 1.32, 16.53 ± 1.67 μM, respectively. Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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8 pages, 2867 KiB  
Article
Penigrisacids A–D, Four New Sesquiterpenes from the Deep-Sea-Derived Penicillium griseofulvum
by Cui-Ping Xing, Chun-Lan Xie, Jin-Mei Xia, Qing-Mei Liu, Wei-Xiang Lin, De-Zan Ye, Guang-Ming Liu and Xian-Wen Yang
Mar. Drugs 2019, 17(9), 507; https://doi.org/10.3390/md17090507 - 29 Aug 2019
Cited by 23 | Viewed by 3271
Abstract
Four new (penigrisacids A–D, 1–4) and one known (5) carotane sesquiterpenoids were isolated from the deep-sea-derived fungus Penicillium griseofulvum, along with four known compounds (6–9). The planar structures and relative configurations of the [...] Read more.
Four new (penigrisacids A–D, 1–4) and one known (5) carotane sesquiterpenoids were isolated from the deep-sea-derived fungus Penicillium griseofulvum, along with four known compounds (6–9). The planar structures and relative configurations of the new compounds were determined by extensive analysis of the NMR and HRESIMS data. The absolute configurations were established by comparison of the experimental and calculated ECD (electronic circular dichroism) spectra or OR (optical rotation) value. Compound 9 exhibited potent anti-food allergic activity with IC50 value of 28.7 μM, while 4 showed weak cytotoxicity against ECA-109 tumor cells (IC50 = 28.7 μM). Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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10 pages, 964 KiB  
Article
Phenazine Derivatives with Anti-Inflammatory Activity from the Deep-Sea Sediment-Derived Yeast-Like Fungus Cystobasidium laryngis IV17-028
by Hwa-Sun Lee, Jong Soon Kang, Byeoung-Kyu Choi, Hyi-Seung Lee, Yeon-Ju Lee, Jihoon Lee and Hee Jae Shin
Mar. Drugs 2019, 17(8), 482; https://doi.org/10.3390/md17080482 - 19 Aug 2019
Cited by 14 | Viewed by 4005
Abstract
Three new phenazine derivatives (1–3), along with known compounds (4–7) of saphenic acid derivatives, were isolated from a deep-sea sediment-derived yeast-like fungus Cystobasidium larynigs collected from the Indian Ocean. The structures of the new compounds [...] Read more.
Three new phenazine derivatives (1–3), along with known compounds (4–7) of saphenic acid derivatives, were isolated from a deep-sea sediment-derived yeast-like fungus Cystobasidium larynigs collected from the Indian Ocean. The structures of the new compounds (1–3) were determined by analysis of spectroscopic data, semi-synthesis and comparison of optical rotation values. All the isolated compounds (1–7), except for 2, showed nitric oxide (NO) production inhibitory effect against lipopolysaccharide (LPS)-induced murine macrophage RAW 264.7 cells without cytotoxicity at concentrations up to 30 μg/mL. This is the first report on the yeast-like fungus Cystobasidium laryngis producing phenazines and anti-inflammatory activity of 1–7 including saphenic acid (4). Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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11 pages, 1650 KiB  
Article
New Glutamine-Containing Azaphilone Alkaloids from Deep-Sea-Derived Fungus Chaetomium globosum HDN151398
by Chunxiao Sun, Xueping Ge, Shah Mudassir, Luning Zhou, Guihong Yu, Qian Che, Guojian Zhang, Jixing Peng, Qianqun Gu, Tianjiao Zhu and Dehai Li
Mar. Drugs 2019, 17(5), 253; https://doi.org/10.3390/md17050253 - 28 Apr 2019
Cited by 29 | Viewed by 4154
Abstract
Three new azaphilone alkaloids containing glutamine residues, namely N-glutarylchaetoviridins A–C (1–3), together with two related compounds (4 and 5) were isolated from the extract of Chaetomium globosum HDN151398, a fungus isolated from a deep-sea sediment sample [...] Read more.
Three new azaphilone alkaloids containing glutamine residues, namely N-glutarylchaetoviridins A–C (1–3), together with two related compounds (4 and 5) were isolated from the extract of Chaetomium globosum HDN151398, a fungus isolated from a deep-sea sediment sample collected in South China Sea. Their structures were elucidated on the basis of extensive 1D and 2D NMR as well as HRESIMS spectroscopic data and chemical analysis. N-glutarylchaetoviridins A–C (1–3) represent the first class of chaetoviridins characterized by embedded glutamate residues. Amino acids incubation experiments produced five azaphilone laden different amino acids residues (6–10) which indicated that this method can enhanced the structural diversity of this strain by culturing with amino acids. Cytotoxicity of the isolated compounds were evaluated against a panel of human cancer cell lines. Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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9 pages, 826 KiB  
Article
Identification of the Anti-Infective Aborycin Biosynthetic Gene Cluster from Deep-Sea-Derived Streptomyces sp. SCSIO ZS0098 Enables Production in a Heterologous Host
by Mingwei Shao, Juying Ma, Qinglian Li and Jianhua Ju
Mar. Drugs 2019, 17(2), 127; https://doi.org/10.3390/md17020127 - 21 Feb 2019
Cited by 26 | Viewed by 4595
Abstract
Aborycin is a ribosomally synthesized member of the type I lasso peptide natural products. In the present study, aborycin was isolated and identified from the deep-sea-derived microbe Streptomyces sp. SCSIO ZS0098. The aborycin biosynthetic gene cluster (abo) was identified on the [...] Read more.
Aborycin is a ribosomally synthesized member of the type I lasso peptide natural products. In the present study, aborycin was isolated and identified from the deep-sea-derived microbe Streptomyces sp. SCSIO ZS0098. The aborycin biosynthetic gene cluster (abo) was identified on the basis of genome sequence analyses and then heterologously expressed in Streptomyces coelicolor M1152 to effectively produce aborycin. Aborycin generated in this fashion exhibited moderate antibacterial activity against 13 Staphylococcus aureus strains from various sources with minimum inhibitory concentrations MICs = 8.0~128 µg/mL, against Enterococcus faecalis ATCC 29212 with an MIC = 8.0 µg/mL, and against Bacillus thuringiensis with MIC = 2.0 µg/mL. Additionally, aborycin displayed potent antibacterial activity (MIC = 0.5 µg/mL) against the poultry pathogen Enterococcus gallinarum 5F52C. The reported abo cluster clearly has the potential to provide a means of expanding the repertoire of anti-infective type I lasso peptides. Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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13 pages, 3168 KiB  
Article
Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus Cladosporium sphaerospermum EIODSF 008
by Xiao Liang, Zhong-Hui Huang, Xuan Ma and Shu-Hua Qi
Mar. Drugs 2018, 16(11), 448; https://doi.org/10.3390/md16110448 - 15 Nov 2018
Cited by 20 | Viewed by 3759
Abstract
Seven new unstable tetramic acid derivatives, cladosporiumins I-O (1–7), together with the known analogue cladodionen (8) were isolated from the extract of the deep-sea-derived fungus Cladosporium sphaerospermum EIODSF 008. Their structures were elucidated by spectroscopic analysis, quantum [...] Read more.
Seven new unstable tetramic acid derivatives, cladosporiumins I-O (1–7), together with the known analogue cladodionen (8) were isolated from the extract of the deep-sea-derived fungus Cladosporium sphaerospermum EIODSF 008. Their structures were elucidated by spectroscopic analysis, quantum chemical calculations and ECD spectra. Compound 4 was a Mg complex of tetramic acid derivative. In acidic solvent, 4 could change to 1 and 6, and 7 could change to 5. In addition, 1, 5 and 8 existed as two exchangeable isomers, respectively. The structures of cladosporiumins E-H were reassigned as their Na complexes. The antibacterial and cytotoxic activities of 1–8 were also evaluated. However, because of their instability, all of the isolated compounds did not show significant antibacterial activity as the preliminary EtOAc extracts of the fungal strain. Full article
(This article belongs to the Special Issue Deep-Sea Natural Products II)
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