Stylissamides E and F, Cyclic Heptapeptides from the Caribbean Sponge <i>Stylissa caribica</i>

Cychon, Christine; Köck, Matthias

doi:10.1021/np900664f

Cited by 25 publications

(14 citation statements)

References 28 publications

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“…In addition, the analysis of the pharmacological activity data revealed that heptacyclopeptide 7 displayed a higher bioactivity against pathogenic microbes and earthworms than its linear form 6 , which is due to the fact that cyclization of peptides reduces the degree of freedom for each constituent within the ring and thus substantially leads to reduced flexibility, increased potency and selectivity of cyclic peptide. In contrast to synthetic heptacyclopeptide 7 , neither natural stylissamide G [19] nor other heptacyclopeptides of the stylissamide class isolated from the marine sponge Stylissa caribica including stylissamides A-F, H and X [19,27,59,60] are reported to possess pharmacological activity against pathogenic microbes and earthworms. However, literature supports inhibitory activity towards protein translation and cell migration possessed by stylissamide A and X respectively [26,27].…”

Section: Discussionmentioning

confidence: 99%

First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge

et al. 2016

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A natural heptacyclopeptide, stylissamide G (7), previously isolated from the Bahamian marine sponge Stylissa caribica from the Caribbean Sea, was synthesized via coupling of the tetrapeptide l-phenylalanyl-l-prolyl-l-phenylalanyl-l-proline methyl ester with the tripeptide Boc-l-leucyl-l-isoleucyl-l-proline, followed by cyclization of the linear heptapeptide fragment. The structure of the synthesized cyclooligopeptide was confirmed using quantitative elemental analysis, FT-IR, 1H NMR, 13C NMR and mass spectrometry. Results of pharmacological activity studies indicated that the newly synthesized cycloheptapeptide displayed good anthelmintic potential against Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus eugeniea at 2 mg/mL and in addition, potent antifungal activity against pathogenic Candida albicans and dermatophytes Trichophyton mentagrophytes and Microsporum audouinii at a concentration of 6 μg/mL.

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Section: Discussionmentioning

confidence: 99%

First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge

et al. 2016

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“…Stylissamides A-D are cyclic heptapeptides that were isolated from Stylissa caribica and included three proline residues in stylissamides A, C, & D and four proline residues in stylissamide B [116]. In addition, stylissamides E [117], F [117], G [118], and H [118] were also isolated from S. caribica . Stylissamide E included two proline residues while stylissamide F was a polar peptide with three proline residues [117].…”

Section: Bioactive Peptides From Various Marine Sourcesmentioning

confidence: 99%

Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology

Gogineni

Hamann

2018

Biochimica et Biophysica Acta (BBA) - General Subjects

122

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The oceans are a uniquely rich source of bioactive metabolites, of which sponges have been shown to be among the most prolific producers of diverse bioactive secondary metabolites with valuable therapeutic potential. Much attention has been focused on marine bioactive peptides due to their novel chemistry and diverse biological properties. As summarized in this review, marine peptides are known to exhibit various biological activities such as antiviral, anti-proliferative, antioxidant, anti-coagulant, anti-hypertensive, anti-cancer, antidiabetic, antiobesity, and calcium-binding activities. This review focuses on the chemistry and biology of peptides isolated from sponges, bacteria, cyanobacteria, fungi, ascidians, and other marine sources. The role of marine invertebrate microbiomes in natural products biosynthesis is discussed in this review along with the biosynthesis of modified peptides from different marine sources. The status of peptides in various phases of clinical trials is presented, as well as the development of modified peptides including optimization of PK and bioavailability.

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“…Arguably the most significant challenge in CP design is our poor understanding of their sequence–structure relationships. The current majority of experimental structural information for small CPs (≤8 amino acids) comes from X‐ray crystal structures and NMR structures in organic solvent . However, X‐ray crystal structures lack dynamic information, providing only a single snapshot among a possible ensemble of structures available in solution.…”

Section: Experimental Design Of Cyclic Peptidesmentioning

confidence: 99%

Understanding and designing head‐to‐tail cyclic peptides

2018

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Cyclic peptides (CPs) are an exciting class of molecules with a variety of applications. However, design strategies for CP therapeutics, for example, are generally limited by a poor understanding of their sequence-structure relationships. This knowledge gap often leads to a trial-and-error approach for designing CPs for a specific purpose, which is both costly and time-consuming. Herein, we describe the current experimental and computational efforts in understanding and designing head-to-tail CPs along with their respective challenges. In addition, we provide several future directions in the field of computational CP design to improve its accuracy, efficiency and applicability. These advances, combined with experimental techniques, shall ultimately provide a better understanding of these interesting molecules and a reliable working platform to rationally design CPs with desired characteristics.

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Stylissamides E and F, Cyclic Heptapeptides from the Caribbean Sponge Stylissa caribica

Cited by 25 publications

References 28 publications

First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge

First Total Synthesis and Biological Screening of a Proline-Rich Cyclopeptide from a Caribbean Marine Sponge

Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology

Understanding and designing head‐to‐tail cyclic peptides

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