Solomonamides A and B, New Anti-inflammatory Peptides from <i>Theonella swinhoei</i>

Festa, Carmen; Marino, Simona De; Sepe, Valentina; D’Auria, Maria Valeria; Bifulco, Giuseppe; Debitus, Cécile; Bucci, Mariarosaria; Vellecco, Valentina; Zampella, Angela

doi:10.1021/ol200221n

Cited by 67 publications

(69 citation statements)

References 10 publications

(10 reference statements)

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“…A Solomon Lithistid sponge T. swinhoei was the source of 2 new cyclopeptides Perthamides C and D with potent anti-inflammatory (93,94) (Festa et al, 2009). Cyclic peptides, Solomonamides A and B (95,96) , were separated out from the marine sponge T. swinhoei ; however, only compound (86) showed anti-inflammatory activity (Festa et al, 2011). The marine sponge S. massa produced a cyclic peptide Stylissatin A (97) that inhibited nitric oxide production in LPS-stimulated murine macrophage RAW264.7 cells with an IC 50 value of 87 μM (Kita et al, 2013).…”

Section: Anti-inflammatory Nrps (Figure 9)mentioning

confidence: 99%

The Pharmacological Potential of Non-ribosomal Peptides from Marine Sponge and Tunicates

2016

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Marine biodiversity is recognized by a wide and unique array of fascinating structures. The complex associations of marine microorganisms, especially with sponges, bryozoans, and tunicates, make it extremely difficult to define the biosynthetic source of marine natural products or to deduce their ecological significance. Marine sponges and tunicates are important source of novel compounds for drug discovery and development. Majority of these compounds are nitrogen containing and belong to non-ribosomal peptide (NRPs) or mixed polyketide–NRP natural products. Several of these peptides are currently under trial for developing new drugs against various disease areas, including inflammatory, cancer, neurodegenerative disorders, and infectious disease. This review features pharmacologically active NRPs from marine sponge and tunicates based on their biological activities.

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Section: Anti-inflammatory Nrps (Figure 9)mentioning

confidence: 99%

The Pharmacological Potential of Non-ribosomal Peptides from Marine Sponge and Tunicates

2016

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“…Solomonamides A and B ( 55 – 56 ) are 4-residue cyclic peptides with a unique 4-amino-6-(2’-amino-4’-hydroxyphenyl)-3,5-dihydroxy-2-methyl-6-oxohexanoic acid residue isolated from the same specimen of Theonella swinhoei that contained perthamides C and D ( 47 – 48 ) (Figure 10 and Figure 12) [48]. 55 displayed a dose-dependent anti-inflammatory response causing nearly a 60% reduction of edema in mice at a dose of 100 μg/kg (ip.).…”

Section: Cyclic Peptidesmentioning

confidence: 99%

Natural Products from the Lithistida: A Review of the Literature since 2000

2011

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Lithistid sponges are known to produce a diverse array of compounds ranging from polyketides, cyclic and linear peptides, alkaloids, pigments, lipids, and sterols. A majority of these structurally complex compounds have very potent and interesting biological activities. It has been a decade since a thorough review has been published that summarizes the literature on the natural products reported from this amazing sponge order. This review provides an update on the current taxonomic classification of the Lithistida, describes structures and biological activities of 131 new natural products, and discusses highlights from the total syntheses of 16 compounds from marine sponges of the Order Lithistida providing a compilation of the literature since the last review published in 2002.

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“…antitubercular activity [7], cytotoxic activity [8], anti-inflammatory activity [9,10], HIV-inhibitory activity [11,12], chymotrypsin-inhibitory activity [13], antimicrobial activity [14] etc. Moreover, peptides (linear and cyclic) are among some of the secondary metabolites isolated from the sponge-associated bacteria (e.g., theopalauamide [15], nazumamide A [16], cycloligopeptides [17], etc.)…”

Section: Introductionmentioning

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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Solomonamides A and B, New Anti-inflammatory Peptides from Theonella swinhoei

Cited by 67 publications

References 10 publications

The Pharmacological Potential of Non-ribosomal Peptides from Marine Sponge and Tunicates

The Pharmacological Potential of Non-ribosomal Peptides from Marine Sponge and Tunicates

Natural Products from the Lithistida: A Review of the Literature since 2000

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

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