Unguisins A and B:  New Cyclic Peptides from the Marine-Derived Fungus <i>Emericella unguis</i>

Malmstrøm, Joan

doi:10.1021/np980539z

Cited by 50 publications

(51 citation statements)

References 11 publications

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“…The presence of GABA in (228-230) induces an enhanced conformational mobility relative to the cyclic peptides derived solely from R-amino acids. Such conformation-biological activity dependence strengthens the occurrence of GABA in 228-230 [114][115][116].…”

Section: Cyclic Peptides and Depsipeptidessupporting

confidence: 59%

“…Unguisins A-C (228-230) were reported as the first cyclic heptapeptides of the gamma aminobutyric acid (GABA) skeleton, isolated from the marine-derived fungus E. unguis, which was isolated from a Venezuelan cannonball jellyfish, Stomolopus meliagris [114,115]. 228 and 229 ( Figure 15) displayed moderate effects against Staphylococcus aureus, but no activity against Vibrio parahaemolyticus.…”

Section: Cyclic Peptides and Depsipeptidesmentioning

confidence: 99%

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Nidulantes of Aspergillus (Formerly Emericella): A Treasure Trove of Chemical Diversity and Biological Activities

et al. 2020

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The genus Emericella (Ascomycota) includes more than thirty species with worldwide distribution across many ecosystems. It is considered a rich source of diverse metabolites. The published classes of natural compounds that are discussed here are organized according to the following biosynthetic pathways: polyketides (azaphilones, cyclopentenone pigments, dicyanides, furan derivatives, phenolic ethers, and xanthones and anthraquinones); shikimate derivatives (bicoumarins); mevalonate derivatives (meroterpenes, sesquiterpenes, sesterterpenes and steroids) and amino acids derivatives (alkaloids (indole-derivatives, isoindolones, and piperazine) and peptides (depsipeptides)). These metabolites produce the wide array of biological effects associated with Emericella, including antioxidant, antiproliferative, antimalarial, antiviral, antibacterial, antioxidant, antihypertensive, anti-inflammatory, antifungal and kinase inhibitors. Careful and extensive study of the diversity and distribution of metabolites produced by the genus Emericella (either marine or terrestrial) revealed that, no matter the source of the fungus, the composition of the culture medium effectively controls the metabolites produced. The topic of this review is the diversity of metabolites that have been identified from Emericella, along with the contextual information on either their biological or geographic sources. This review presents 236 natural compounds, which were reported from marine and terrestrial Emericella. Amongst the reported compounds, only 70.2% were biologically assayed for their effects, including antimicrobial or cytotoxicity. This implies the need for substantial investigation of alternative activities. This review includes a full discussion of compound structures and disease management, based on materials published from 1982 through December 2019.

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Section: Cyclic Peptides and Depsipeptidessupporting

confidence: 59%

Section: Cyclic Peptides and Depsipeptidesmentioning

confidence: 99%

Nidulantes of Aspergillus (Formerly Emericella): A Treasure Trove of Chemical Diversity and Biological Activities

et al. 2020

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“…Unguisin A is a marinederived cyclic heptapeptide containing the rare structural feature of a GABA residue imbedded within the macrocycle. [23] We recently completed the first total synthesis of unguisin A with a macrocyclization approach (Scheme 1), [24] and so the new goal was to obtain analogues containing 1 or 2 (or the enantiomers of these fluorinated building blocks) in place of the GABA component. This ambition also raised an additional question: the building blocks 1 and 2 would give rise to differently shaped linear precursor peptides, and so it was of interest to determine whether these different shapes would manifest in different cyclization efficiencies.…”

mentioning

confidence: 99%

Stereoselective Fluorination Alters the Geometry of a Cyclic Peptide: Exploration of Backbone‐Fluorinated Analogues of Unguisin A

Thomas²,

Griffith

et al. 2014

Angew Chem Int Ed

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New methods for enhancing the efficiency of peptide cyclization, and for fine-tuning the conformations of cyclic peptides, are valuable from a drug development perspective. Herein stereoselective fluorination is investigated as a new strategy for achieving these goals. Four vicinal difluorinated analogues of the natural cyclic heptapeptide unguisin A have been efficiently synthesized. The analogues are found to adopt dramatically different secondary structures, controlled by the fluorine stereochemistry.

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“…[23] We recently completed the first total synthesis of unguisin A with a macrocyclization approach (Scheme 1), [24] and so the new goal was to obtain analogues containing 1 or 2 (or the enantiomers of these fluorinated building blocks) in place of the GABA component. Unguisin A is a marinederived cyclic heptapeptide containing the rare structural feature of a GABA residue imbedded within the macrocycle.…”

mentioning

confidence: 99%

Stereoselective Fluorination Alters the Geometry of a Cyclic Peptide: Exploration of Backbone‐Fluorinated Analogues of Unguisin A

Thomas²,

Griffith

et al. 2014

Angewandte Chemie

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Unguisins A and B: New Cyclic Peptides from the Marine-Derived Fungus Emericella unguis

Cited by 50 publications

References 11 publications

Nidulantes of Aspergillus (Formerly Emericella): A Treasure Trove of Chemical Diversity and Biological Activities

Nidulantes of Aspergillus (Formerly Emericella): A Treasure Trove of Chemical Diversity and Biological Activities

Stereoselective Fluorination Alters the Geometry of a Cyclic Peptide: Exploration of Backbone‐Fluorinated Analogues of Unguisin A

Stereoselective Fluorination Alters the Geometry of a Cyclic Peptide: Exploration of Backbone‐Fluorinated Analogues of Unguisin A

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