Koshikamide A<sub>2</sub>, a Cytotoxic Linear Undecapeptide Isolated from a Marine Sponge of<i>Theonella</i>sp.

Araki, Tsuyoshi; Matsunaga, Shigeki; Fusetani, Nobuhiro

doi:10.1271/bbb.69.1318

Cited by 20 publications

(12 citation statements)

References 14 publications

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“…Mutremd-amide A ( 1 ) contains a rare 2-amino-3-(2-hydroxyphenyl)-propanoic acid and the new N δ -carbamoyl-β-sulfated asparagine residue. Compounds 2 – 7 add to the rare class of highly N -methylated peptides named koshikamides (two linear, koshikamide A1 23 and A2, 24 and one cyclic, koshikamide B), with koshikamides F and G being the first natural peptides to possess a 2-(3-amino-5-oxopyrrolidin-2-ylidene)-propanoic acid moiety. Thus far, it is only in deeper Theonella collections (averaging 100 m) such as those studied here that we have detected the presence of mutremdamide A together with koshikamides and/or theonellamides.…”

Section: Resultsmentioning

confidence: 99%

Mutremdamide A and Koshikamides C−H, Peptide Inhibitors of HIV-1 Entry from Different Theonella Species

et al. 2010

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A new sulfated cyclic depsipeptide, termed mutremdamide A, and six new highly N-methylated peptides, termed koshikamides C–H, were isolated from different deep-water specimens of Theonella swinhoei and Theonella cupola. Their structures were determined using extensive 2D NMR, ESI, or CDESI and QTOF-MS/MS experiments and absolute configurations established by quantum mechanical calculations, advanced Marfey's method, and chiral HPLC. Mutremdamide A displays a rare 2-amino-3-(2-hydroxyphenyl)propanoic acid and a new Nδ-carbamoyl-β-sulfated asparagine. Koshikamides C–E are linear undecapeptides, and koshikamides F–H are 17-residue depsipeptides containing a 10-residue macrolactone. Koshikamides F and G differ from B and H in part by the presence of the conjugated unit 2-(3-amino-5-oxopyrrolidin-2-ylidene)propanoic acid. Cyclic koshikamides F and H inhibited HIV-1 entry at low micromolar concentrations while their linear counterparts were inactive. The Theonella collections studied here are distinguished by co-occurrence of mutremdamide A, koshikamides, and theonellamides, the combination of which appears to define a new Theonella chemotype that can be found in deeper waters.

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Section: Resultsmentioning

confidence: 99%

Mutremdamide A and Koshikamides C−H, Peptide Inhibitors of HIV-1 Entry from Different Theonella Species

et al. 2010

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“…Its structure was elucidated to be a linear undecapeptide by spectroscopic and chemical methods, together with enzymatic conversion to known koshikamide A1 (1). The new peptide moderately inhibited the growth of P388 murine leukemia cells 71 .…”

Section: Anti-hiv Peptidesmentioning

confidence: 92%

Untitled

2012

IJPSR

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Marine sponges, the sessile invertebrates of the Phylum porifera are invaluable tool in current research. They remain as a goldmine to chemist and pharmacologist due to its defensive weapons, the secondary metabolites. Endogenous peptides from marine sponges and associated microorganisms are promising lead compound for drug development. Some of the compounds are under clinical trials. These peptides can act against variety of diseases in humans including bacterial, fungal, protozoan, HIV, inflammatory and even tumor. This review focuses on sponge symbiotic association with other organisms, significance of peptides as secondary metabolites and its pharmacological effects by highlighting its role as antbacterial, anti-fungal, anti-HIV and anti-tumor agents. Sponge-microbial associations are found to be very specific in the production of particular bioactive compounds.

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“…collected off Shimo-koshiki-jima Island, Kagoshima, Japan (Figure 14) [52]. The structure of 58 was determined to be a close structural homolog of the previously described Koshikamide A 1 with an additional arginine residue added to the C -terminus.…”

Section: Linear Peptidesmentioning

confidence: 98%

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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Koshikamide A₂, a Cytotoxic Linear Undecapeptide Isolated from a Marine Sponge ofTheonellasp.

Cited by 20 publications

References 14 publications

Mutremdamide A and Koshikamides C−H, Peptide Inhibitors of HIV-1 Entry from Different Theonella Species

Mutremdamide A and Koshikamides C−H, Peptide Inhibitors of HIV-1 Entry from Different Theonella Species

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

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Koshikamide A2, a Cytotoxic Linear Undecapeptide Isolated from a Marine Sponge ofTheonellasp.

Cited by 20 publications

References 14 publications

Mutremdamide A and Koshikamides C−H, Peptide Inhibitors of HIV-1 Entry from Different Theonella Species

Mutremdamide A and Koshikamides C−H, Peptide Inhibitors of HIV-1 Entry from Different Theonella Species

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

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Koshikamide A₂, a Cytotoxic Linear Undecapeptide Isolated from a Marine Sponge ofTheonellasp.