ChemInform Abstract: Kulolide: A Cytotoxic Depsipeptide from a Cephalaspidean Mollusk, Philinopsis speciosa.

Reese, Michael T.; Gulavita, Nanda K.; Nakao, Yoichi; Hamann, Mark; Yoshida, Wesley Y.; Coval, Stephen J.; Scheuer, Paul J.

doi:10.1002/chin.199710166

Cited by 10 publications

(17 citation statements)

References 1 publication

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“…9 Consequently, both 2 and 3 were subjected to hydrogenation over palladium on carbon to form compound 4 prior to hydrolysis. The hydrolysis products were partitioned between 0.1 N HCl and EtOAc to afford the amino acids in the aqueous phase and the lipid chain in the organic phase.…”

Section: Discussionmentioning

confidence: 99%

Almiramides A−C: Discovery and Development of a New Class of Leishmaniasis Lead Compounds

Sanchez¹,

Lopéz²,

Vesely³

et al. 2010

J. Med. Chem.

102

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Leishmaniasis is a debilitating disease caused by protozoan parasites of the genus Leishmania, which affects an estimated 12 million people worldwide. The discovery of new lead compounds for leishmaniasis is therefore a pressing concern for global health programs. The organic extract of a Panamanian collection of the marine cyanobacterium Lyngbya majuscula showed strong in vitro activity in two complementary screens against the tropical parasite Leishmania donovani, the causative agent of visceral leishmaniasis. Chromatographic separation of this complex mixture led to the isolation of the highly N-methylated linear lipopeptides, almiramides A–C (1–3). Comparison with the biological activities of a number of related metabolites and semisynthetic derivatives revealed key features required for activity and afforded one new compound (11) with superior in vitro activity. Subsequent synthesis of a library of simplified analogues led to the discovery of several compounds with improved therapeutic indices to the natural products.

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Section: Discussionmentioning

confidence: 99%

Almiramides A−C: Discovery and Development of a New Class of Leishmaniasis Lead Compounds

Sanchez¹,

Lopéz²,

Vesely³

et al. 2010

J. Med. Chem.

102

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“…Both naopopeptin and antanapeptins B and C are cyclic depsipeptides [45,46] containing the Hmoya (3-hydroxy-2-methyl-7-octynoic acid) unit or its derivatives (Hmoea or Hmoaa). Since the isolation of kulolide, the first compound reported to contain the 2,2-dimethyl-3-hydroxy-7-octynoic acid (Dhoya) [47], a variety of structurally similar compounds have been isolated from diverse cyanobacteria [45,48,49] (Fig. 3b).…”

Section: Lc-ms and Molecular Networking Studiesmentioning

confidence: 99%

Bioprospecting Portuguese Atlantic coast cyanobacteria for bioactive secondary metabolites reveals untapped chemodiversity

et al. 2015

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Continental Portugal has an extensive Atlantic Ocean coastline; however little is known about the diversity of its marine cyanobacteria, with only a few reports published. Cyanobacteria are a prolific source of bioactive compounds with promising therapeutic applications. Previously, several cyanobacterial strains (Subsections I-IV) were isolated from the Portuguese Atlantic coast and characterized using a polyphasic approach. Preliminary screening indicated that these cyanobacteria lacked the genes for proteins involved in the production of conventional cyanotoxins. However, it was previously shown that extracts of marine Synechocystis and Synechococcus were toxic to invertebrates, with crude extracts causing stronger effects than partially purified ones. To further evaluate the potential of our temperate region Portuguese isolates to produce bioactive compounds, a PCR screening for the presence of genes encoding non-ribosomal peptide synthetases (NRPSs) and polyketide synthases (PKSs), targeting the adenylation (A) and ketosynthase (KS) domains respectively, was performed. DNA fragments were obtained for more than 80% of the strains tested, and the results revealed that PKS genes are more ubiquitous than NRPS genes. The sequences obtained were used in an in silico prediction of the PKS and NRPS systems. RT-PCR analyses revealed that these genes are transcribed under routine laboratory conditions in several selected strains. Furthermore, LC-MS analysis coupled with molecular networking, a mass spectrometric tool that clusters metabolites with similar MS/MS fragmentation patterns, was used to search for novel or otherwise interesting metabolites revealing an untapped chemodiversity.

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“…Many cyclic peptides having strong and diverse biological activities have been isolated from sponges (Fusetani and Matsunaga, 1993) and ascidians (Davidson, 1993) but rarely from shellfish (Reese et al, 1996). The structure of gamakamide-E resembles the keramamides, anabaenopeptins and oscillamides isolated from sponges and …”

Section: Stereochemistry Of Gamakamide-ementioning

confidence: 99%

Gamakamide-E, a Strongly Bitter Tasting Cyclic Peptide with a Hydantoin Structure from Cultured Oysters Crassostrea gigas

Lee¹,

Satake

Horigome³

et al. 2012

Fisheries and aquatic sciences

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A new cyclic peptide (six-membered amino acid, was isolated as a strongly bitter tasting compound from cultured oysters, Crassostrea gigas. The molecular formula of C 43 H 61 N 7 O 8 S was deduced from high resolution fast atom bom bardment mass spectrometry ( HR FAB-MS) ([M + H]+ m/z 836.4356 △= -2.4 mmu). Its unique structure including a hydantoin structure was firstly elucidated by nuclear magnetic resonance (NMR) analysis. Stereochemistries of constituent amino acids were determined by chiral high performanced liquid chromatography analysis of natural and synthesized peptides.

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ChemInform Abstract: Kulolide: A Cytotoxic Depsipeptide from a Cephalaspidean Mollusk, Philinopsis speciosa.

Cited by 10 publications

References 1 publication

Almiramides A−C: Discovery and Development of a New Class of Leishmaniasis Lead Compounds

Almiramides A−C: Discovery and Development of a New Class of Leishmaniasis Lead Compounds

Bioprospecting Portuguese Atlantic coast cyanobacteria for bioactive secondary metabolites reveals untapped chemodiversity

Gamakamide-E, a Strongly Bitter Tasting Cyclic Peptide with a Hydantoin Structure from Cultured Oysters Crassostrea gigas

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