Neopetrosiamides, Peptides from the Marine Sponge <i>Neopetrosia </i>sp. That Inhibit Amoeboid Invasion by Human Tumor Cells

Williams, David E.; Austin, Pamela; Dı́az-Marrero, Ana R.; Soest, R.W.M. van; Matainaho, Teatulohi; Roskelley, Calvin D.; Roberge, Michel; Andersen, Raymond J.

doi:10.1021/ol051524c

Cited by 54 publications

(46 citation statements)

References 21 publications

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“…2,3-OBenzylidene-5-O-(4-acetoxybenzoyl)-β-D-ribofuranosyl Chloride (7). To a stirred solution of 2,3-O-benzylidene-D-ribose 5 29 (200 mg, 0.840 mmol) in pyridine (3 mL) were added p-acetoxybenzoyl chloride (200 mg, 1.02 mmol, 1.2 equiv) and DMAP (5 mg).…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue

et al. 2015

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Neopetrosides A (1) and B (2), new naturally occurring ribosides of nicotinic acid with extremely rare α-N-glycoside linkages and residues of p-hydroxybenzoic and pyrrole-2-carboxylic acids attached to C-5', were isolated from a marine Neopetrosia sp. sponge. Structures 1 and 2 were determined by NMR and MS methods and confirmed by the synthesis of 1 and its β-riboside analogue (3). Neopetroside A (1) upregulates mitochondrial functions in cardiomyocytes.

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Section: Journal Of Natural Productsmentioning

confidence: 99%

Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue

et al. 2015

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“…Although its molecular formula was not directly determined from the high-resolution MS analysis, the MALDITOF-MS data, in conjunction with the 1 H and 13 C NMR data, established the molecular formula to be C 62 H 89 N 11 O 13 S 2 [4]. The spectroscopic data of this compound were highly reminiscent of the data of 1 , and the loss of signals for a carbonyl and a methylene were the most noticeable differences in both the 1 H and 13 C NMR data.…”

Section: Resultsmentioning

confidence: 99%

“…[4], asteropsin A from Asteropus sp. [15], and the recently reported gombamide A from Clathria gombawuiensis [9] are the only examples in the literature, which confirms the scarcity of these peptides.…”

Section: Resultsmentioning

confidence: 99%

“…Although peptides account for a relatively minor proportion of sponge-derived metabolites, several of these peptides possess highly unique chemical structures and potent bioactivities [1]. Among the recently reported peptides, noticeable examples include the kapakahines [2,3] from Cribrochalina olemeda , the neopetrosiamides [4] from Neopetrosia sp., the koshikamides and mutremdamide A [5,6] from Theonella spp., the yaku’amides [7] from Ceratropsion sp., and the solomonamides [8] from Theonella swinhoei . These compounds possess unusual amino acid residues, uncommon linkages and/or significant bioactivities.…”

Section: Introductionmentioning

confidence: 99%

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New Cyclic Cystine Bridged Peptides from the Sponge Suberites waedoensis

et al. 2014

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Two new peptides, chujamides A (1) and B (2), were isolated from the marine sponge Suberites waedoensis, which was collected from Korean waters. Based upon the results of the combined spectroscopic analyses, the structures of these compounds were determined to be proline-riched and cyclic cystine bridged dodeca- and undecapeptides. The absolute configurations of all amino acid residues were determined to be l by advanced Marfey’s analysis. The new compounds exhibited weak cytotoxicities against A549 and K562 cell-lines, and compound 2 also demonstrated moderate inhibitory activity against Na+/K+-ATPase.

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“…18, No. 2, 2007 In our current search for new biologically active marine natural products, 4,5 we decided to investigate the MeOH crude extract of the sponge Axinella cf. corrugata, which displayed cytotoxic activity against breast MCF-7 and colon B16 cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

A SARS-coronovirus 3CL protease inhibitor isolated from the marine sponge Axinella cf. corrugata: structure elucidation and synthesis

Lira¹,

Seleghim²,

Williams³

et al. 2007

J. Braz. Chem. Soc.

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Dois derivados cumarínicos, o ester metílico do ácido 4-esculetinocarboxílico (1) e o éster etílico do ácido 4-esculetinocarboxílico (2), foram isolados da esponja marinha Axinella cf. corrugata. A determinação estrutural dos compostos isolados foi realizada pela análise de seus dados espectroscópicos e pela síntese do composto 2. Estes são os primeiros derivados cumarínicos isolados de uma esponja marinha. O éster etílico 2 apresentou atividade in vitro contra a SARS 3Cl-protease e de inibição de células Vero infectadas com o SARS coronavírus, em concentrações que não provocaram citotoxicidade.Two coumarin derivatives, esculetin-4-carboxylic acid methyl ester (1) and esculetin-4-carboxylic acid ethyl ester (2), have been isolated from the marine sponge Axinella cf. corrugata. Structure determination included analysis of spectroscopic data and total synthesis of compound 2. These are the first coumarin derivatives isolated from a marine sponge. The ethyl ester 2 was found to be an in vitro inhibitor of SARS 3CL-protease and an effective inhibitor of SARS-CoV replication in Vero cells at non-cytotoxic concentrations.Keywords: esculetin, marine sponge, Axinella cf. corrugata, SARS, anti-viral IntroductionIn 2002 and 2003, several cases of a life-threatening respiratory disease that was ultimately named "severe acute respiratory syndrome" (SARS) were reported from Guangdong Province in mainland China, Hong Kong, Canada, and Vietnam.1 The etiological agent responsible for SARS was quickly found to be a novel coronavirus (SARS-CoV). Among the viral gene products are several large polyproteins that must be proteolytically processed to generate the individual proteins required for viral replication to occur. Two viral proteases, PL2 pro and 3CL pro , are involved in degrading the large polyproteins. 2The viral protease 3CL pro is considered the most important of the two because it is responsible for the release of the key replicative proteins of the vírus, including the viral RNA polymerase and helicase proteins. The central role of 3CL pro in SARS-CoV replication has made it a high profile target for developing antiviral drugs to treat SARS.2 Recently, a novel fluorescence resonance energy transfer (FRET)-based assay to screen for 3CL pro inhibitors has been developed in one of our laboratories.3 As part of a screening of crude marine sponge extracts and pure compounds isolated from the marine sponges using this assay, we have found that the new natural product esculetin-4-carboxylic acid ethyl ester (2) isolated from Axinella cf. corrugata collected in Brazil is a an effective inhibitor of 3CL pro in vitro. 441 Lira et al. Vol. 18, No. 2, 2007 In our current search for new biologically active marine natural products, 4,5 we decided to investigate the MeOH crude extract of the sponge Axinella cf. corrugata, which displayed cytotoxic activity against breast MCF-7 and colon B16 cancer cell lines. Although the cytotoxic activity was lost during the crude extract fractionation, photodiode array detection-HPLC analysi...

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Neopetrosiamides, Peptides from the Marine Sponge Neopetrosia sp. That Inhibit Amoeboid Invasion by Human Tumor Cells

Cited by 54 publications

References 21 publications

Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue

Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue

New Cyclic Cystine Bridged Peptides from the Sponge Suberites waedoensis

A SARS-coronovirus 3CL protease inhibitor isolated from the marine sponge Axinella cf. corrugata: structure elucidation and synthesis

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