Organic Chemistry By Dr. I. L. Finar. Vol. 2: Stereochemistry and the Chemistry of Natural Products. Pp. xi + 733. (London and New York: Longmans, Green and Co., Ltd., 1956.) 40s. net.

Advanced Organic Chemistry

Marine natural products.

The prevalence of antimicrobial resistance reduces the effectiveness of antimicrobial drugs in preventing and treating infectious diseases caused by pathogenic organisms, such as bacteria, fungi, and viruses. Because of the burgeoning growth of microbes with antimicrobial-resistant traits, there is a dire need to identify and develop novel and effective antimicrobial agents to treat infections from antimicrobial-resistant strains. The marine environment is rich in ecological biodiversity and can be regarded as an untapped resource for prospecting novel bioactive compounds. Therefore, exploring the marine environment for antimicrobial agents plays a significant role in drug development and biomedical research. Several earlier scientific investigations have proven that bacterial diversity in the marine environment represents an emerging source of structurally unique and novel antimicrobial agents. There are several reports on marine bacterial secondary metabolites, and many are pharmacologically significant and have enormous promise for developing effective antimicrobial drugs to combat microbial infections in drug-resistant pathogens. In this review, we attempt to summarize published articles from the last twenty-five years (1996-2020) on antimicrobial secondary metabolites from marine bacteria evolved in marine environments, such as marine sediment, water, fauna, and flora.

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Marine Bacterial Secondary Metabolites: A Treasure House for Structurally Unique and Effective Antimicrobial Compounds.

Bacterial and viral infections pose a direct threat to human health due to the increase of drug-resistant and novel pathogenic strains. Natural products represent a prolific source of bioactive metabolites, which have been exploited for their therapeutic effects. In particular, cyanobacteria were identified as important producers of secondary metabolites possessing antibacterial and antiviral activities, among others. A meta-analysis indicated that some natural product classes target bacteria or viruses exclusively. This result also applied for some cyanobacterial species that were identified to produce only antibacterial or antiviral compounds. Furthermore, cyanobacteria represent a promising host for bio-production due to their ability to perform photosynthesis and their low-cost production requirements. This review highlights antibacterial and antiviral compounds isol isolated from cyanobacteria and the biotechnological application of these organisms .

Antibacterial and antiviral metabolites from cyanobacteria: Their application and their impact on human health

Three related new alkylphenols, termed anaephenes A–C (1–3), containing different side chains, were isolated from an undescribed filamentous cyanobacterium (VPG 16-59) collected in Guam. Our 16S rDNA sequencing efforts indicated that VPG 16-59 is a member of the marine genus Hormoscilla (Oscillatoriales). The structures of anaephenes A–C (1–3) were elucidated by spectroscopic methods, and compounds assayed for growth inhibitory activity against prokaryotic and eukaryotic cell lines. Anaephene B (2), possessing a terminal alkyne, displayed moderate activity against Bacillus cereus and Staphylococcus aureus with MIC values of 6.1 μg/mL. While 1 and 3 showed no pronounced activity in these assays, their structural features highlight the unusual biosynthetic capacity of this cyanobacterium and warrant further study.

Isolation and Characterization of Anaephenes A–C, Alkylphenols from a Filamentous Cyanobacterium (Hormoscilla sp., Oscillatoriales)

Biosynthetic mechanisms of natural products primarily depend on systems of protein catalysts. However, within the field of biosynthesis, there are cases in which the inherent chemical reactivity of metabolic intermediates and substrates evades the involvement of enzymes. These reactions are difficult to characterize based on their reactivity and occlusion within the milieu of the cellular environment. As we continue to build a strong foundation for how microbes and higher organisms produce natural products, therein lies a need for understanding how protein independent or nonenzymatic biosynthetic steps can occur. We have classified such reactions into four categories: intramolecular, multicomponent, tailoring, and light-induced reactions. Intramolecular reactions is one of the most well studied in the context of biomimetic synthesis, consisting of cyclizations and cycloadditions due to the innate reactivity of the intermediates. There are two subclasses that make up multicomponent reactions, one being homologous multicomponent reactions which results in dimeric and pseudodimeric natural products, and the other being heterologous multicomponent reactions, where two or more precursors from independent biosynthetic pathways undergo a variety of reactions to produce the mature natural product. The third type of reaction discussed are tailoring reactions, where postmodifications occur on the natural products after the biosynthetic machinery is completed. The last category consists of light-induced reactions involving ecologically relevant UV light rather than high intensity UV irradiation that is traditionally used in synthetic chemistry. This review will cover recent nonenzymatic biosynthetic mechanisms and include sources for those reviewed previously.

Nonenzymatic Reactions in Natural Product Formation.

Our ongoing efforts to explore the chemical space associated with marine cyanobacteria from coral reefs of Guam have yielded two new members of the anaenamide family of natural products, anaenamides C (3) and D (4). These compounds were isolated from a novel Hormoscilla sp. (VPG16-58). Our phylogenetic profiling (16S rDNA) of this cyanobacterium indicated that VPG16-58 is taxonomically distinct from the previously reported producer of the anaephenes, VPG16-59 (Hormoscilla sp.), and other previously documented species of the genus Hormoscilla. The planar structures of 3 and 4 were determined via spectroscopic methods, and absolute configurations of the α-hydroxy acids were assigned by enantioselective HPLC analysis. To address the requirement for sufficient material for testing, we first adapted our published linear synthetic approach for 1 and 2 to generate anaenoic acid (7), which served as a point for diversification, providing the primary amides 3 and 4 from synthetic intermediates 5 and 6, respectively. The compounds were then tested for effects on HCT116 colon cancer cell viability and in an ARE-luciferase reporter gene assay for Nrf2 modulation using HEK293 human embryonic kidney cells. Our findings indicate that, in contrast to cytotoxic methyl esters 1 and 2, the primary amides 3 and 4 activate the Nrf2 pathway at noncytotoxic concentrations. Overall, our data suggest that the anaenamide scaffold is tunable to produce differential biological outcomes.

Discovery, Synthesis, and Biological Evaluation of Anaenamides C and D from a New Marine Cyanobacterium, Hormoscilla sp.

Discovery, Total Synthesis, and SAR of Anaenamides A and B: Anticancer Cyanobacterial Depsipeptides with a Chlorinated Pharmacophore.

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Isolation and Characterization of Anaephenes A–C, Alkylphenols from a Filamentous Cyanobacterium (Hormoscilla sp., Oscillatoriales)

Nonenzymatic Reactions in Natural Product Formation.

Discovery, Synthesis, and Biological Evaluation of Anaenamides C and D from a New Marine Cyanobacterium, Hormoscilla sp.

Discovery, Total Synthesis, and SAR of Anaenamides A and B: Anticancer Cyanobacterial Depsipeptides with a Chlorinated Pharmacophore.