Bioactive Products from Marine Cyanobacteria and Their Potential Therapeutic Applications 2022

A special issue of Marine Drugs (ISSN 1660-3397). This special issue belongs to the section "Marine Pharmacology".

Deadline for manuscript submissions: closed (27 September 2022) | Viewed by 9146

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Department of Chemistry, The University of Waikato, Te Whare Wānanga o Waikato, Gate 1 Knighton Road, Private Bag 3105, Hamilton 3240, New Zealand
Interests: natural products chemistry; application of spectral methods to structural determination; biologically active compounds and structure-activity relationships; chemical ecology
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Special Issue Information

Dear Colleagues,

Cyanobacteria (blue-green algae) are an ancient and successful group of organisms, found in a wide range of marine and freshwater habitats and in conditions as extreme as the cold of Antarctica to the heat of volcanic regions. They have proven to be an excellent source of secondary metabolites, many of which possess biological activity. The most common class of compounds found in cyanobacteria are oligopeptides (predominantly cyclic peptides), of which many contain unique or unusual amino acids. These are synthesised by non-ribosomal peptide synthetases. Some of the other compound classes that have been isolated from cyanobacteria include terpenes and alkaloids.

Many of the natural products produced by cyanobacteria may be ecologically significant and some of the toxic metabolites are a human health concern, especially when present in recreational water bodies or fisheries. Cyanobacteria often have the means to produce many more metabolites than are actually expressed, so an understanding of biosynthesis and genetics in these organisms is vitally important.

There is considerable overlap between metabolites produced by terrestrial and marine cyanobacteria, however, this Special Issue will only include studies concerning freshwater cyanobacteria if there is obvious relevance to marine species. We look forward to receiving your contributions.

Dr. Michele R. Prinsep
Guest Editor

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Keywords

  • cyanobacteria
  • blue-green algae
  • oligopeptide
  • noribosomal peptide sythetase
  • biological activity
  • toxicity

Published Papers (3 papers)

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Research

12 pages, 2222 KiB  
Article
Isolation and Biological Activity of Iezoside and Iezoside B, SERCA Inhibitors from Floridian Marine Cyanobacteria
by Sofia Kokkaliari, Danmeng Luo, Valerie J. Paul and Hendrik Luesch
Mar. Drugs 2023, 21(7), 378; https://doi.org/10.3390/md21070378 - 27 Jun 2023
Viewed by 1376
Abstract
Marine cyanobacteria are a rich source of bioactive natural products. Here, we report the isolation and structure elucidation of the previously reported iezoside (1) and its C-31 O-demethyl analogue, iezoside B (2), from a cyanobacterial assemblage collected at Loggerhead [...] Read more.
Marine cyanobacteria are a rich source of bioactive natural products. Here, we report the isolation and structure elucidation of the previously reported iezoside (1) and its C-31 O-demethyl analogue, iezoside B (2), from a cyanobacterial assemblage collected at Loggerhead Key in the Dry Tortugas, Florida. The two compounds have a unique skeleton comprised of a peptide, a polyketide and a modified sugar unit. The compounds were tested for cytotoxicity and effects on intracellular calcium. Both compounds exhibited cytotoxic activity with an IC50 of 1.5 and 3.0 μΜ, respectively, against A549 lung carcinoma epithelial cells and 1.0 and 2.4 μΜ against HeLa cervical cancer cells, respectively. In the same cell lines, compounds 1 and 2 show an increase in cytosolic calcium with approximate EC50 values of 0.3 and 0.6 μΜ in A549 cells and 0.1 and 0.5 μΜ, respectively, in HeLa cells, near the IC50 for cell viability, suggesting that the increase in cytosolic calcium is functionally related to the cytotoxicity of the compounds and consistent with their activity as SERCA (sarcoplasmic/endoplasmic reticulum Ca2+-ATPase) inhibitors. The structure–activity relationship provides evidence that structural changes in the sugar unit may be tolerated, and the activity is tunable. This finding has implications for future analogue synthesis and target interaction studies. Full article
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13 pages, 562 KiB  
Article
New Nostocyclophanes from Nostoc linckia
by Jingqiu Dai, Casey S. Philbin, Clay Wakano, Wesley Y. Yoshida and Philip G. Williams
Mar. Drugs 2023, 21(2), 101; https://doi.org/10.3390/md21020101 - 31 Jan 2023
Cited by 4 | Viewed by 3891
Abstract
Six new nostocyclophanes and four known compounds have been isolated from Nostoc linckia (Nostocaceae) cyanobacterial strain UTEX B1932. The new compounds, nostocyclophanes E–J (16), were characterized by NMR and MS techniques. The known compounds were nostocyclophanes B–D, previously isolated [...] Read more.
Six new nostocyclophanes and four known compounds have been isolated from Nostoc linckia (Nostocaceae) cyanobacterial strain UTEX B1932. The new compounds, nostocyclophanes E–J (16), were characterized by NMR and MS techniques. The known compounds were nostocyclophanes B–D, previously isolated from this strain, and dedichloronostocyclophane D. Structural modifications on the new [7.7]paracyclophane analogs 15, isolated from the 80% methanol fraction, range from simple changes such as the lack of methylation or halogenation to more unusual modifications such as those seen in nostocyclophane H (4), in which the exocyclic alkyl chains are of different length; this is the first time this modification has been observed in this family of natural products. In addition, nostocyclophane J (6) is a linear analog in which C-20 is chlorinated in preparation for the presumed enzymatic Friedel–Craft cyclization needed to form the final ring structure, analogous to the biosynthesis of the related cylindrocyclophanes. Nostocyclophane D, dedichloronostocyclophane D, and nostocyclophanes E-J demonstrated moderate to weak growth inhibition against MDA-MB-231 breast cancer cells. Full article
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13 pages, 2272 KiB  
Article
Identification of Anhydrodebromoaplysiatoxin as a Dichotomic Autophagy Inhibitor
by Limin Feng, Chung-Kuang Lu, Jiajun Wu, Leo Lai Chan and Jianbo Yue
Mar. Drugs 2023, 21(1), 46; https://doi.org/10.3390/md21010046 - 10 Jan 2023
Cited by 2 | Viewed by 1592
Abstract
Dysfunctional autophagy is associated with various human diseases, e.g., cancer. The discovery of small molecules modulating autophagy with therapeutic potential could be significant. To this end, we screened the ability of a series of metabolites isolated from marine microorganisms to modulate autophagy. Anhydrodebromoaplysiatoxin [...] Read more.
Dysfunctional autophagy is associated with various human diseases, e.g., cancer. The discovery of small molecules modulating autophagy with therapeutic potential could be significant. To this end, we screened the ability of a series of metabolites isolated from marine microorganisms to modulate autophagy. Anhydrodebromoaplysiatoxin (ADAT), a metabolite yielded by the marine red algae Gracilaria coronopifolia, inhibited autophagosome-lysosome fusion in mammalian cells, thereby inducing the accumulation of autophagosomes. Treatment of cells with ADAT alkalinized lysosomal pH. Interestingly, ADAT also activated the mTOR/p70S6K/FoxO3a signaling pathway, likely leading to the inhibition of autophagy induction. ADAT had little effect on apoptosis. Our results suggest that ADAT is a dichotomic autophagy inhibitor that inhibits both late-stage (autophagosome-lysosome fusion) and early-stage (autophagy induction) autophagy. Full article
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