Marine Pyrrole Alkaloids

Seipp, Kevin; Geske, Leander; Opatz, Till

doi:10.3390/md19090514

Cited by 57 publications

(49 citation statements)

References 377 publications

(875 reference statements)

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“…The structure of pyrroles, with a high electron density in their heteroaromatic ring, is of special interest when developing new bioactive drugs [ 96 ]. The alkaloids of this subgroup attract a great interest for their anticancer, antimicrobial, antiviral, antimalarial, antitubercular, anti-inflammatory, and enzyme inhibiting properties [ 97 ].…”

Section: New Alkaloids Found In Mushroom Since 2002mentioning

confidence: 99%

Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

Zorrilla

Evidente

2022

Biomolecules

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Alkaloids are a wide family of basic N-containing natural products, whose research has revealed bioactive compounds of pharmacological interest. Studies on these compounds have focused more attention on those produced by plants, although other types of organisms have also been proven to synthesize bioactive alkaloids, such as animals, marine organisms, bacteria, and fungi. This review covers the findings of the last 20 years (2002–2022) related to the isolation, structures, and biological activities of the alkaloids produced by mushrooms, a fungal subgroup, and their potential to develop drugs and agrochemicals. In some cases, the synthesis of the reviewed compounds and structure−activity relationship studies have been described.

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Section: New Alkaloids Found In Mushroom Since 2002mentioning

confidence: 99%

Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

Zorrilla

Evidente

2022

Biomolecules

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“…Pyrroles are prevalently isolated from marine organisms, reflected by a recent review focusing on pyrroles from marine sources covering the decade from 2010 to 2020 [26]. While most marine pyrroles originate from sponges, several actinomycetes were also found to be hosts to novel pyrroles (Figure 4).…”

Section: Pyrrolesmentioning

confidence: 99%

Novel Alkaloids from Marine Actinobacteria: Discovery and Characterization

et al. 2021

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The marine environment is an excellent resource for natural products with therapeutic potential. Its microbial inhabitants, often associated with other marine organisms, are specialized in the synthesis of bioactive secondary metabolites. Similar to their terrestrial counterparts, marine Actinobacteria are a prevalent source of these natural products. Here, we discuss 77 newly discovered alkaloids produced by such marine Actinobacteria between 2017 and mid-2021, as well as the strategies employed in their elucidation. While 12 different classes of alkaloids were unraveled, indoles, diketopiperazines, glutarimides, indolizidines, and pyrroles were most dominant. Discoveries were mainly based on experimental approaches where microbial extracts were analyzed in relation to novel compounds. Although such experimental procedures have proven useful in the past, the methodologies need adaptations to limit the chance of compound rediscovery. On the other hand, genome mining provides a different angle for natural product discovery. While the technology is still relatively young compared to experimental screening, significant improvement has been made in recent years. Together with synthetic biology tools, both genome mining and extract screening provide excellent opportunities for continued drug discovery from marine Actinobacteria.

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“…[15][16][17] Heterocyclic compounds containing the 3,4-dihydropyrrolo [1,2-a]pyrazin-1(2H)-one moiety occur in a number of natural products of marine origin. 18 This intriguing chemical architecture of annellated pyrroles was investigated by several teams involved in the total synthesis of natural products, [19][20][21] but its potential as an innovative scaffold in medicinal chemistry is still overlooked even though the role of natural products as an inspiration for chemical templates in drug discovery programs is quite established. Structural features of natural products such as the presence of elements of asymmetry might be advantageous in exploring demanding biological targets.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of 3,4‐dihydropyrrolo[1,2‐a]pyrazin‐1(2H)‐one derivatives as PIM kinase inhibitors inspired from marine alkaloids

et al. 2022

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We previously demonstrated that natural product‐inspired 3,4‐dihydropyrrolo[1,2‐a]pyrazin‐1(2H)‐ones derivatives delivered potent and selective PIM kinases inhibitors however with non‐optimal ADME/PK properties and modest oral bioavailability. Herein, we describe a structure‐based scaffold decoration and a stereoselective approach to this chemical class. The synthesis, structure–activity relationship studies, chiral analysis, and pharmacokinetic data of compounds from this inhibitor class are presented herein. Compound 20c demonstrated excellent potency on PIM1 and PIM2 with exquisite kinases selectivity and PK properties that efficiently and dose‐dependently promoted c‐Myc degradation and appear to be promising lead compounds for further development.

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Marine Pyrrole Alkaloids

Cited by 57 publications

References 377 publications

Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

Novel Alkaloids from Marine Actinobacteria: Discovery and Characterization

Stereoselective synthesis of 3,4‐dihydropyrrolo[1,2‐a]pyrazin‐1(2H)‐one derivatives as PIM kinase inhibitors inspired from marine alkaloids

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