Sch 217048:  A Novel Cyclodepsipeptide with Neurokinin Antagonist Activity

Hegde, V. R.; Puar, Mohindar S.; Chan, T. M.; Dai, Peng; Das, Pradip R.; Patel, Mahesh

doi:10.1021/jo981467j

Cited by 14 publications

(14 citation statements)

References 7 publications

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“…5), were isolated and identified based on comparison of their retention times and HRESIMS and MS/MS fragmentation patterns to standards in our in-house database (El-Elimat et al 2013). The NMR data for the compounds were also consistent with those reported in the literature (Hegde et al 1998(Hegde et al , 2001El-Elimat et al 2017). Additionally, the same compounds were identified in cultures of G618, G833, and G834, all grown on PDA, and analyzed by in situ sampling analysis using a droplet-LMJ-SSP coupled to an UPLC-high-resolution mass spectrometry (HRMS) (Sica et al 2015) (Fig.…”

Section: Mb 817996supporting

confidence: 72%

“…Additionally, 2 was recently isolated from an unidentified coprophilous fungus belonging to the Pleosporaceae, along with other closely related cyclodepsipeptides (Isaka et al 2014). Both compounds have been described to have selective inhibition against human NK2 receptors (Hegde et al 1998(Hegde et al , 2001, and 2 exhibited antimalarial activity against Plasmodium falciparum K1 (Isaka et al 2014). Compounds 1 and 2 were also tested for antimicrobial and cytotoxicity in this study, but no significant inhibitions were observed.…”

Section: Discussionmentioning

confidence: 86%

“…Based on our previous studies, this niche has proven to be diverse in both mycological (Raja et al 2013a(Raja et al , b, 2015Crous et al 2015) and chemical discoveries (El-Elimat et al 2014a, b, 2017Paguigan et al 2016). Chemical exploration of the newly described species, L. carolinensis and L. cigarospora, resulted in the identification of two known cyclodepsipeptides, Sch 378161 (1) and Sch 217048 (2), and the isolation of both of them were first reported from an unidentified fungal fermentation broth (Hegde et al 1998(Hegde et al , 2001Chu et al 2000). Additionally, 2 was recently isolated from an unidentified coprophilous fungus belonging to the Pleosporaceae, along with other closely related cyclodepsipeptides (Isaka et al 2014).…”

Section: Discussionmentioning

confidence: 99%

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Additions to Lindgomyces (Lindgomycetaceae, Pleosporales, Dothideomycetes), including two new species occurring on submerged wood from North Carolina, USA, with notes on secondary metabolite profiles

Raja

Paguigan

Fournier³

et al. 2017

Mycol Progress

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Two new species of freshwater ascomycetes belonging to the genus Lindgomyces (Pleosporales, Dothideomycetes) are described and illustrated from submerged wood in North Carolina, USA. Lindgomyces carolinensis is characterized by immersed to erumpent ascomata, fissitunicate broadly cylindrical to clavate asci, and fusiform ascospores with acute ends surrounded by a large, fusiform gelatinous sheath. Lindgomyces cigarospora morphologically differs from L. carolinensis in that its ascospores are fusiform to cylindrical with rounded ends, without a large fusiform gelatinous sheath. These two new species nest in the family Lindgomycetaceae based on analyses of combined SSU and LSU rDNA sequence data. Phylogenetic analyses using ITS sequence data support the establishment of the new taxa as separate species within Lindgomyces. In addition to the new species, we report new ITS sequence data for L. cinctosporus and L. griseosporus from France, and L. ingoldianus from North Carolina, USA. We report a video exhibiting fissitunicate ascus dehiscence in L. carolinensis showing ascospore discharge and unraveling of the gelatinous sheath in real time. Chemical analysis of the organic extracts of L. carolinensis and L. cigarospora resulted in two known cyclodepsipeptides, Sch 378161 and Sch 217048. The in situ spatial mapping of these secondary metabolites on fungal cultures indicates the presence of both compounds on the surface of mycelia, as well as being exuded into the surrounding agar.

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Section: Mb 817996supporting

confidence: 72%

Section: Discussionmentioning

confidence: 86%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Additions to Lindgomyces (Lindgomycetaceae, Pleosporales, Dothideomycetes), including two new species occurring on submerged wood from North Carolina, USA, with notes on secondary metabolite profiles

Raja

Paguigan

Fournier³

et al. 2017

Mycol Progress

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“…SCH217048 (Fig. 42) was isolated from an unidentified fungal culture at Schering-Plough [124]. The culture sample was collected from a Sri Lankan forest.…”

Section: Li-f Antibioticsmentioning

confidence: 99%

Recent Developments in Depsipeptide Research

Ballard¹,

Yu²,

Wang³

2002

CMC

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This review focuses on the major developments in depsipeptide research since 1995. Depsipeptides are bio-oligomers composed of hydroxy and amino acids linked by amide and ester bonds. Many depsipeptides show very promising biological activities, including anticancer, antibacterial, antiviral, antifungal, anti-inflammatory, and anti-clotting or anti-antherogenic properties. In this report depsipeptides exhibiting these properties are discussed. Their isolation, structural determination, and notable structural features are discussed, but their biological properties and therapeutic potentials are emphasized. Depsipeptides have shown the greatest therapeutic potential as anticancer agents. Four depsipeptides have entered clinical trials for cancer treatment. Among the antiviral compounds discovered, the callipeltins and the quinoxapeptins are particularly promising due to their inhibitory activities against HIV. These compounds have the potential to be developed as anti-AIDS drugs or to serve as lead compounds for the discovery of structurally related anti-AIDS compounds. Antifungal compounds, such as the jaspamides, may lead to therapies against many of the opportunistic infections that accompany AIDS. Anti-inflammatory compounds such as SCH217048 act as neurokinin antagonists and may lead to anti-inflammatory treatments. Some depsipeptides such as micropeptins and A90720A have been found to be effective plasmin inhibitors, which have implications as treatments for cardiovascular diseases. Compounds such as SCH58149 help control the levels of HDL and LDL.

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“…22 Other bioactive fungal cyclodepsipeptides such as the ionophore beauvericin 23,24 and the neurokinin antagonist Sch 217048 25 have also been reported. A noteworthy structural feature of the petrosifungins is the array of the three neighboring cyclic amino acids proline and twice pipecolinic acid, which in this sequence has never been observed before in a natural cyclopeptide.…”

Section: Resultsmentioning

confidence: 99%

Petrosifungins A and B, Novel Cyclodepsipeptides from a Sponge-Derived Strain of Penicillium brevicompactum

et al. 2004

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A strain of Penicillium brevicompactum derived from a specimen of the Mediterranean sponge Petrosia ficiformis was investigated for its secondary metabolites. Using fast centrifugal partitioning chromatography (FCPC) two previously unknown cyclodepsipeptides, petrosifungins A (1) and B (2), were isolated, both containing two neighboring units of the nonproteinogenic amino acid l-pipecolinic acid. The absolute configurations of all amino acids were established to be l using GITC derivatization and Marfey's method. Furthermore, the known metabolite brevianamide A (3) was isolated. The likewise known compounds mycophenolic acid (4) and asperphenamate (5) were identified from their spectroscopic properties directly in the extract using HPLC-UV, -MS, and -NMR coupling.

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Sch 217048: A Novel Cyclodepsipeptide with Neurokinin Antagonist Activity

Cited by 14 publications

References 7 publications

Additions to Lindgomyces (Lindgomycetaceae, Pleosporales, Dothideomycetes), including two new species occurring on submerged wood from North Carolina, USA, with notes on secondary metabolite profiles

Additions to Lindgomyces (Lindgomycetaceae, Pleosporales, Dothideomycetes), including two new species occurring on submerged wood from North Carolina, USA, with notes on secondary metabolite profiles

Recent Developments in Depsipeptide Research

Petrosifungins A and B, Novel Cyclodepsipeptides from a Sponge-Derived Strain of Penicillium brevicompactum

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