Carteritins A and B, cyclic heptapeptides from the marine sponge Stylissa carteri

Afifi, Ahmed H.; El‐Desoky, Ahmed H.; Kato, Hikaru; Mangindaan, Remy E.P.; Voogd, Nicole J. de; Ammar, Nagwa M.; Hifnawy, Mohamed S.; Tsukamoto, Sachiko

doi:10.1016/j.tetlet.2016.02.031

Cited by 29 publications

(22 citation statements)

References 9 publications

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“…405 As always, a large number of peptidic and peptide-hybrid natural products have been reported from sponges in 2016. Metagenomic analysis has shown that kasumigamide 833, a known freshwater cyanobacterial product, is produced by an Entotheonella symbiont in a Discodermia sponge, 406,407 while other peptides were sourced from the Theonella (834-836), 408 Stylissa (837-841), 409,410 Cribrochalina (842), 411 Callyspongia (843), 412 Asteropus (845-849) 413,414 and Petrosia (850-852) 415 genera. A Japanese (Nakagi, Shizuoka Prefecture) specimen of Discodermia kiiensis was the source of sulfolipodiscamides A-C 853-855, unprecedented N-sulfouridyl containing-compounds and essentially the sulfonated analogues of the known lipodiscamides A-C, 416 isolated again concurrently from the same sponge.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2018

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Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

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Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2018

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“…Marfey’s method was also successfully used for evaluation of the stereochemistry of the amino acids of the cyclic peptides stylisins 1 ( 148 ) and 2 ( 149 ), stylissatins B–D ( 152 – 154 ), and carteritins A ( 150 ) and B ( 151 ), isolated from marine sponge S tylissa sp. [ 137 , 138 , 139 ], as well as of callyaerin G ( 155 ), isolated from the marine sponge Callyspongia aerizusa [ 140 ].…”

Section: Peptides From Marine Spongesmentioning

confidence: 99%

Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities

et al. 2018

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Over the last decades, many naturally occurring peptides have attracted the attention of medicinal chemists due to their promising applicability as pharmaceuticals or as models for drugs used in therapeutics. Marine peptides are chiral molecules comprising different amino acid residues. Therefore, it is essential to establish the configuration of the stereogenic carbon of their amino acid constituents for a total characterization and further synthesis to obtain higher amount of the bioactive marine peptides or as a basis for structural modifications for more potent derivatives. Moreover, it is also a crucial issue taking into account the mechanisms of molecular recognition and the influence of molecular three-dimensionality in this process. In this review, a literature survey covering the report on the determination of absolute configuration of the amino acid residues of diverse marine peptides by chromatographic methodologies is presented. A brief summary of their biological activities was also included emphasizing to the most promising marine peptides. A case study describing an experience of our group was also included.

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“…[31], Indo-Pacific sponges Phakellia costata and Stylotella aurantium [32], Indonesian sponge Stylissa sp. [33], Red sea sponge Stylissa carteri [34], Western Pacific Ocean sponge Hymeniacidon sp. [35], Puerto Rican sponge Prosuberites laughlini [36], Micronesian sponge Cribrochalina olemda [37], Indonesian sponge Sidonops microspinosa [38], Palau sponge Axinella sp.…”

Section: Introductionmentioning

confidence: 99%

Natural Proline-Rich Cyclopolypeptides from Marine Organisms: Chemistry, Synthetic Methodologies and Biological Status

et al. 2016

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Peptides have gained increased interest as therapeutics during recent years. More than 60 peptide drugs have reached the market for the benefit of patients and several hundreds of novel therapeutic peptides are in preclinical and clinical development. The key contributor to this success is the potent and specific, yet safe, mode of action of peptides. Among the wide range of biologically-active peptides, naturally-occurring marine-derived cyclopolypeptides exhibit a broad range of unusual and potent pharmacological activities. Because of their size and complexity, proline-rich cyclic peptides (PRCPs) occupy a crucial chemical space in drug discovery that may provide useful scaffolds for modulating more challenging biological targets, such as protein-protein interactions and allosteric binding sites. Diverse pharmacological activities of natural cyclic peptides from marine sponges, tunicates and cyanobacteria have encouraged efforts to develop cyclic peptides with well-known synthetic methods, including solid-phase and solution-phase techniques of peptide synthesis. The present review highlights the natural resources, unique structural features and the most relevant biological properties of proline-rich peptides of marine-origin, focusing on the potential therapeutic role that the PRCPs may play as a promising source of new peptide-based novel drugs.

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Carteritins A and B, cyclic heptapeptides from the marine sponge Stylissa carteri

Cited by 29 publications

References 9 publications

Marine natural products

Marine natural products

Marine Natural Peptides: Determination of Absolute Configuration Using Liquid Chromatography Methods and Evaluation of Bioactivities

Natural Proline-Rich Cyclopolypeptides from Marine Organisms: Chemistry, Synthetic Methodologies and Biological Status

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