Isolation and structures of pipecolidepsins A and B, cytotoxic cyclic depsipeptides from the Madagascan sponge Homophymia lamellosa.

@article{Coello2014IsolationAS,
  title={Isolation and structures of pipecolidepsins A and B, cytotoxic cyclic depsipeptides from the Madagascan sponge Homophymia lamellosa.},
  author={L. Coello and F. Reyes and María Jesús Martín and C. Cuevas and R. Fernández},
  journal={Journal of natural products},
  year={2014},
  volume={77 2},
  pages={
          298-303
        }
}
Two new cyclic depsipeptides, pipecolidepsins A and B (1 and 2), have been isolated from the sponge Homophymia lamellosa collected off the coast of Madagascar. Their structures were determined by a combination of NMR experiments and by LC-MS analysis of the amino acid fragments obtained by hydrolysis and derivatization using Marfey's reagent. In addition to several common amino acids, these peptides contain unusual residues, including 2-amino-3-hydroxy-4,5-dimethylhexanoic acid, 3… Expand
Daedophamide, a Cytotoxic Cyclodepsipeptide from a Daedalopelta sp. Sponge Collected in Indonesia.
TLDR
Compound 1 displayed strong cytotoxic activity against a panel of four human tumor cell lines with GI50 values in the submicromolar range and was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. Expand
Xylapeptide A, an Antibacterial Cyclopentapeptide with an Uncommon L-Pipecolinic Acid Moiety from the Associated Fungus Xylaria sp. (GDG-102)
Two new cyclopentapeptides, xylapeptide A (1) with an uncommon L-pipecolinic acid moiety, and xylapeptide B (2) having a common L-proline residue were identified from an associated fungus Xylaria sp.Expand
A pipecolic acid-rich branched cyclic depsipeptide ulleungamide C from a Streptomyces species induces G0/G1 cell cycle arrest in promyelocytic leukemia cells.
TLDR
Ulleungamide C (1), a previously unknown pipecolic acid-rich branched cyclic depsipeptide, from a soil actinobacterium Streptomyces sp. Expand
Reniochalistatins A-E, cyclic peptides from the marine sponge Reniochalina stalagmitis.
TLDR
The cyclic octapeptide reniochalistatin E showed biological activity in various cytotoxicity assays employing different tumor cell lines (RPMI-8226, MGC-803, HL-60, HepG2, and HeLa). Expand
Stellatolide H, a cytotoxic peptide lactone from a deep-sea sponge Discodermia sp.
Abstract Stellatolide H (1) was isolated from a deep-sea sponge Discodermia sp. as the cytotoxic constituent. The planar structure of 1 was elucidated on the basis of the NMR spectroscopic and massExpand
Total synthesis of callipeltin B and M, peptidyl marine natural products.
Total synthesis of callipeltins B and M, peptidyl cytotoxic agents isolated from marine sponges, by the combination of Fmoc solid-phase peptide synthesis and cyclization and global deprotection inExpand
Combining JBCA and Marfey's methodology to determine the absolute configuration of threonines: the case of gunungamide A, a new cyclic depsipeptide containing chloropyrrole from the sponge Discodermia sp.
A combination of configurational analysis based on coupling constants (JBCA) and Marfey's aminoacid derivatization allowed us to distinguish between the different possible diastereoisomers ofExpand
New cytotoxic callipeltins from the Solomon Island marine sponge Asteropus sp.
Abstract Four new callipeltin A derivatives (N–Q) have been isolated from the Solomon Island marine sponge Asteropus sp. Their structures were established by spectroscopic techniques followed by acidExpand
Synthesis of fully protected (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxy heptanoic acid
Abstract (2 R ,3 R ,4 S )-4-Amino-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE), a common constituent of biologically active marine peptides, callipeltin A ( 1 ) and neamphamide A, was synthesizedExpand
Synthetic studies directed towards hunanamycin, teixobactin and telomycin antibiotic natural products and their analogues
The emergence of bacteria resistant to all clinically approved antibiotics has led to a worldwide search for new drugs. Without new antibiotics many aspects of modern medicine would become nearlyExpand
...
1
2
3
...

References

SHOWING 1-10 OF 24 REFERENCES
The first total synthesis of the cyclodepsipeptide pipecolidepsin A.
TLDR
The first total synthesis of a D-allo-AHDMHA-containing peptide, pipecolidepsin A, is described, allowing chemical structure validation of the natural product and providing a robust synthetic strategy to access other members of the relevant head-to-side-chain family in a straightforward manner. Expand
Papuamides A-D, HIV-inhibitory and cytotoxic depsipeptides from the sponges Theonella mirabilis and Theonella swinhoei, collected in Papua New Guinea
TLDR
Papuamides A−D (1−4) are also the first marine-derived peptides reported to contain 3-hydroxyleucine and homoproline residues, and contain a previously undescribed 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid moiety N-linked to a terminal glycine residue. Expand
Neamphamide A, a new HIV-inhibitory depsipeptide from the Papua New Guinea marine sponge Neamphius huxleyi.
TLDR
A new HIV-inhibitory cyclic depsipeptide isolated from a Papua New Guinea collection of the marine sponge Neamphius huxleyi exhibited potent cytoprotective activity against HIV-1 infection with an EC50 of approximately 28 nM. Expand
Theopapuamide, a cyclic depsipeptide from a Papua New Guinea lithistid sponge Theonella swinhoei.
TLDR
Theopapuamide (1), a new cytotoxic peptide, has been isolated from the lithistid sponge Theonella swinhoei from Papua New Guinea and contains several unusual amino acid residues, of which the occurrence of beta-methoxyasparagine and 4-amino-5-methyl-2,3,5-trihydroxyhexanoic acid (Amtha) is unprecedented in natural peptides. Expand
Callipeltin A, an Anti-HIV Cyclic Depsipeptide from the New Caledonian Lithistida Sponge Callipelta sp.
Callipeltin A (1) is a cyclic depsidecapeptide from a shallow water sponge of the genus Callipelta (order Lithistida), collected in the waters off New Caledonia. The structure of callipeltin A (1),Expand
Homophymine A, an anti-HIV cyclodepsipeptide from the sponge Homophymia sp.
TLDR
A new anti-HIV cyclodepsipeptide was isolated from a New Caledonian collection of the marine sponge Homophymia sp. Expand
Celebesides A-C and theopapuamides B-D, depsipeptides from an Indonesian sponge that inhibit HIV-1 entry.
TLDR
Six new depsipeptides belonging to two different structural classes, termed celebesides A-C and theopapuamides B-D, have been isolated from the marine sponge Siliquariaspongia mirabilis using extensive 2D NMR and ESI-MS/MS techniques. Expand
Mirabamides A-D, depsipeptides from the sponge Siliquariaspongia mirabilis that inhibit HIV-1 fusion.
TLDR
Four new cyclic depsipeptides termed mirabamides A-D (1-4) have been isolated from the marine sponge Siliquariaspongia mirabilis and shown to potently inhibit HIV-1 fusion and demonstrate that these peptides can act at the early stages of HIV- 1 entry. Expand
Neamphamide B, new cyclic depsipeptide, as an anti-dormant mycobacterial substance from a Japanese marine sponge of Neamphius sp.
TLDR
A new cyclic depsipeptide isolated from a marine sponge of Neamphius sp. Expand
Callipeltins B and C; Bioactive Peptides from a. Marine Lithistida Sponge Callipelta sp.
Abstract Following the characterization of callipeltin A (1), two new cytotoxic peptides, callipeltin B (2) and C (3), were isolated from the New Caledonian sponge Callipelta sp.. Callipeltin B (2)Expand
...
1
2
3
...