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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes T&#252;6028
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Two new aromatic polyketides from a sponge-derived Fusarium.

Mada Triandala Sibero1,2, Tao Zhou3, Keisuke Fukaya3

  • 1Department of Marine Science, Faculty of Fisheries and Marine Science, Diponegoro University, Tembalang Campus, St. Prof. Soedarto SH, Semarang, 50275 Central Java, Indonesia.

Beilstein Journal of Organic Chemistry
|January 11, 2020
PubMed
Summary

Marine fungi yielded two new karimunones (A and B) and five known compounds. Karimunone B demonstrated antibacterial activity against multidrug-resistant Salmonella Typhi.

Keywords:
Fusariumaromatic polyketidemarine fungussecondary metabolitesponge

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Area of Science:

  • Marine Natural Products Chemistry
  • Mycology
  • Chemical Biology

Background:

  • Marine fungi are a prolific source of novel bioactive compounds.
  • The screening of marine-derived microorganisms is crucial for discovering new therapeutic agents.
  • Sponge-associated fungi represent an underexplored niche for natural product discovery.

Purpose of the Study:

  • To isolate and characterize new aromatic polyketides from a sponge-associated fungus.
  • To evaluate the bioactivity of the isolated compounds, particularly against multidrug-resistant bacteria.

Main Methods:

  • Isolation and purification of compounds using chromatographic techniques.
  • Structure elucidation of new compounds employing Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS).
  • Computational analysis, including Density Functional Theory (DFT) based chemical shift calculations, aided NMR assignment.

Main Results:

  • Two new aromatic polyketides, karimunones A (1) and B (2), were identified.
  • Five known compounds (3-7) were also isolated from the Fusarium sp. KJMT.FP.4.3.
  • Karimunone B (2) exhibited antibacterial activity against multidrug-resistant Salmonella enterica serovar Typhi with a Minimum Inhibitory Concentration (MIC) of 125 µg/mL.

Conclusions:

  • The study successfully identified novel aromatic polyketides from a marine-derived fungus.
  • Karimunone B shows potential as an antibacterial agent against a significant human pathogen.
  • Further investigation into karimunone B's mechanism of action and structure-activity relationship is warranted.