Structure elucidation and antimalarial activity of apicidin F: an apicidin-like compound produced by Fusarium fujikuroi.

@article{vonBargen2013StructureEA,
  title={Structure elucidation and antimalarial activity of apicidin F: an apicidin-like compound produced by Fusarium fujikuroi.},
  author={Katharina Walburga von Bargen and Eva-Maria Niehaus and Klaus Bergander and Reto Brun and Bettina Tudzynski and Hans-Ulrich Humpf},
  journal={Journal of natural products},
  year={2013},
  volume={76 11},
  pages={
          2136-40
        }
}
Apicidins are cyclic tetrapeptides with histone deacetylase inhibitory activity. Since their discovery in 1996 a multitude of studies concerning the activity against protozoa and certain cancer cell lines of natural and synthetic apicidin analogues have been published. Until now, the only published natural sources of apicidin are the fungus Fusarium pallidoroseum, later known as F. semitectum and two unspecified Fusarium strains. The biosynthetic origin of apicidins could be associated with a… Expand
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Purification and Phytotoxicity of Apicidins Produced by the Fusarium semitectum KCTC16676
TLDR
To enhance apicidin production, after culturing isolate KCTC16676 on a wheat medium for 3 weeks at 25oC, the culture was extracted with chloroform and showed phytotoxicity on both seedlings and 2-week-old plants of diverse species, and weeds were more sensitive to apICidins than vegetables. Expand
Functional characterization and manipulation of the apicidin biosynthetic pathway in Fusarium semitectum
TLDR
The cluster gene APS2, a putative transcription factor, was shown to regulate expression of the genes in the cluster and overexpression ofAPS2 increased apicidin production. Expand
Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase.
TLDR
A novel fungal metabolite, apicidin, that exhibits potent, broad spectrum antiprotozoal activity in vitro against Apicomplexan parasites has been identified and is also orally and parenterally active in vivo against Plasmodium berghei malaria in mice. Expand
Structure and chemistry of apicidins, a class of novel cyclic tetrapeptides without a terminal alpha-keto epoxide as inhibitors of histone deacetylase with potent antiprotozoal activities.
TLDR
The isolation and structure elucidation of new apicidins from two Fusarium species, temperature-dependent NMR studies of apicIDin, NMR and molecular modeling based conformation of the 12-membered macrocyclic ring, and selected chemical modifications of Apicidin have been detailed in this paper. Expand
Structure, histone deacetylase, and antiprotozoal activities of apicidins B and C, congeners of apicidin with proline and valine substitutions.
TLDR
These are the new members of a unique family of cyclic tetrapeptides that do not require the electrophilic alpha-epoxyketone moiety of HC-toxin, trapoxin A, or chlamydocin for their potent activities against HDAC and the malarial parasite. Expand
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The structure of open-chain fusarin C was elucidated, and on the basis of these data, the rearrangement product of fusarins under different conditions was identified as epi-fusarinC, which was confirmed by detailed NMR measurements and density functional theory calculations. Expand
Apicidins: Novel cyclic tetrapeptides as coccidiostats and antimalarial agents from Fusarium pallidoroseum
Abstract Apicidin is a cyclic tetrapeptide [cyclo-(N-O-Methyl-L-Trp-L-Ile-D-Pip-L-2-amino-8-oxo-decanoyl)] isolated from Fusarium pallidoroseum by bioassay guided separation. It is a potent inhibitorExpand
Synthesis of apicidin-derived quinolone derivatives: parasite-selective histone deacetylase inhibitors and antiproliferative agents.
TLDR
The new quinolones exhibited good parasite selectivity and potency both at the level of their molecular target, histone deacetylase, and in their whole cell antiproliferative activity in vitro. Expand
A Hemorrhagic Factor (Apicidin) Produced by Toxic Fusarium Isolates from Soybean Seeds
ABSTRACT Fifty-two isolates of Fusarium species were obtained from soybean seeds from various parts of Korea and identified asFusarium oxysporum, F. moniliforme, F. semitectum, F. solani, F.Expand
Broad spectrum antiprotozoal agents that inhibit histone deacetylase: structure-activity relationships of apicidin. Part 1.
TLDR
The conversion of apicidin, a nanomolar inhibitor of HDACs, into a series of side-chain analogues that display picomolar enzyme affinity is described within this structure-activity study. Expand
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