Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives.

  title={Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives.},
  author={Yasuha Kusakabe and Shoma Mizutani and Shogo Kamo and Tatsuki Yoshimoto and Shusuke Tomoshige and Tsuneomi Kawasaki and Ryoko Takasawa and Kazunori Tsubaki and Kouji Kuramochi},
  journal={Bioorganic \& medicinal chemistry letters},
  volume={29 11},
Discovery of New Schiff Bases Tethered Pyrazole Moiety: Design, Synthesis, Biological Evaluation, and Molecular Docking Study as Dual Targeting DHFR/DNA Gyrase Inhibitors with Immunomodulatory Activity
Immunomodulatory activities showed that the promising Schiff bases increase the immunomodulator effect of defense cell and the Schiff base 8a is the highest one by (Intra. killing activity = 136.5 ± 0.3%) having a pyrazole moiety as well as amide function (O=C-NH2) and piperidinyl core.
Antimalarials and Phytotoxins from Botryosphaeria dothidea Identified from a Seed of Diseased Torreya taxifolia
An EtOAc extract of the broth of the endophyte Botryosphaeria dothidea isolated from a seed collected from a Torreya taxifolia plant with disease symptoms, showed in vitro antimalarial and phytotoxic activities.
Biological Evaluation and Molecular Docking with In Silico Physicochemical, Pharmacokinetic and Toxicity Prediction of Pyrazolo[1,5-a]pyrimidines
The molecular docking study demonstrated that the pyrazolo[1,5-a]pyrimidines are potent inhibitors of 14-alpha demethylase, transpeptidase and alkaline phosphatase enzymes and could be valuable in the discovery of a new series of drugs.
Heterologous Production of Unnatural Flavipucine Family Products Provides Insights into Flavipucines Biosynthesis.
Heterologous expression of the flavipucine biosynthetic gene cluster in Aspergillus nidulans led to the production of flavipucine (1) and dihydroisoflavipucine (3), as well as six unusual flavipucine
An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies
An overview of the biological roles and synthetic strategies of saturated cyclic ethers is provided, covering some of the most studied and newly discovered related natural products in recent years, and several promising and newly developed synthetic methods are reported.
Diversity and characteristics of culturable endophytic bacteria from Passiflora edulis seeds
Results suggest that the bacteria remain static in the seeds due to the presence of piceatannol and are transmitted to the seedlings during the germination process, enabling colonies to be established from the seedling derived from the seeds on the agar medium.


(+)‐Flavipucine, the Missing Member of the Pyridione Epoxide Family of Fungal Antibiotics
From the culture extracts of the endophytic fungus, Phoma sp., isolated from the plant Salsola oppositifolia, five secondary metabolites were isolated and characterized. On biomalt agar medium, the
Synthesis and biological activity of flavipucine analogues.
A series of analogues of flavipucine prepared possessing side chain as well as nuclear variants were found to exhibit enhanced activity against several bacteria and fungi as compared with the natural product itself.
Metabolism and pharmacokinetics of the camptothecin analogue CPT-11 in the mouse.
In vitro incubation of CPT-11 in mouse serum or tissue homogenate enhanced the growth-inhibitory activity much more than that expected from the concentration of C PT-11, and it is suggested that the maintenance of plasma SN-38 concentration might be necessary for it to exhibit antitumor activity in vivo.
Flavipucine and Brunnescin, Two Antibiotics from Cultures of the Mycophilic Fungus Cladobotryum rubrobrunnescens
The metabolite isolated from submerged cultures of Cladobotryum rubrobrunnescens, a mycophilic fungus growing on a Inocybe species, is a new tetrasubstituted furan derivative which exhibits antibacterial, antifungal and cytotoxic effects.
A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and (±)-Isoflavipucine.
The construction of the core tricyclic ring system of rubrobramide was achieved by a cascade reaction in a single step from an α,β-epoxy-γ-lactam and the absolute configuration of naturally occurring (+)-rubrobramid was determined by vibrational circular dichroism.
Rubrobramide, a cytotoxic and phytotoxic metabolite from Cladobotyrum rubrobrunnescens.
Cladobotrin (1) and rubrobramide (2), possessing a unique oxidized tricyclic system, is a new compound structurally related to flavipucine (3), which also is produced by the fungus.
Talaramide A, an unusual alkaloid from the mangrove endophytic fungus Talaromyces sp. (HZ-YX1) as an inhibitor of mycobacterial PknG
An unusual alkaloid, talaramide A (1), was obtained from the mangrove endophytic fungus Talaromyces sp. (HZ-YX1). The structure of 1 was established by analysis of NMR spectroscopic data, X-ray
In vitro evaluation of the determinants of bactericidal activity of ampicillin dosing regimens against Escherichia coli
An in vitro flow model was used to examine the influence of peak concentration (Cmax), the area under the antibiotic concentration-time curve (AUC), the magnitude of AUC above the MIC, and the
The structure of isoflavipucine
The structure of isoflavipucine 2a, a remarkable rearrangement product of the antibiotic flavipucine 1, is proposed on the basis of spectral data and chemical and mechanistic considerations.
The X-ray crystal structure of (±)-flavipucine
Synthetic (±)-flavipucine (C12H15O4N) is monoclinic, space groupP21/c, with a = 11.506(5), b = 8.765(5), c = 11.981(7) A, β = 91.09(2)°, Z = 4. X-ray analysis confirms its structure as 1,