Alternatone A, an Unusual Perylenequinone-Related Compound from a Soft-Coral-Derived Strain of the Fungus Alternaria alternata

J Nat Prod. 2019 Nov 22;82(11):3201-3204. doi: 10.1021/acs.jnatprod.9b00905. Epub 2019 Oct 29.

Abstract

A novel perylenequinone-related compound, alternatone A (1), with an unprecedented tricyclo[6.3.1.02,7] dodecane skeleton, together with three known perylenequinones, altertoxin I (2), stemphyperylenol (3), and alterperylenol (4), was isolated from the soft-coral-derived fungus Alternaria alternata L3111'. Their structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic analysis, electronic circular dichroism calculations, and X-ray diffraction data. Compound 4 showed cytotoxicity against A-549, HCT-116, and HeLa cell lines with IC50 values of 2.6, 2.4, and 3.1 μM, respectively. A possible biosynthetic pathway of 1 was proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alternaria / chemistry*
  • Animals
  • Anthozoa / microbiology*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / pharmacology
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Perylene / analogs & derivatives*
  • Perylene / chemistry
  • Perylene / pharmacology
  • Quinones / chemistry*
  • Quinones / pharmacology*
  • X-Ray Diffraction

Substances

  • Anti-Bacterial Agents
  • Antibiotics, Antineoplastic
  • Quinones
  • perylenequinone
  • Perylene