Iizukines C-E from a saline soil fungus Aspergillus iizukae

Bioorg Chem. 2019 Oct:91:103167. doi: 10.1016/j.bioorg.2019.103167. Epub 2019 Jul 31.

Abstract

Three new alkaloids, iizukines C-E (1-3), including two aspochalasins (1 and 2), and one brasiliamide derivative (3), along with two known aspochalasins, rosellichalasin (4) and cytochalasin Z17 (5), were isolated from the culture of Aspergillus iizukae. Compound 1 was the first aspochalasin uniquely featuring a 1,2,4-triazole functionality, and 3 showed a pair of NMR signals in CDCl3 with a ratio of about 2:1 due to the existence of conformational isomers. Their structures were determined by extensive spectroscopic analyses and single-crystal X-ray diffractions. In particular, the 1,2,4-triazole moiety in 1 was assigned on the basis of extremely valuable 1H-15N HMBC spectrum. Compound 1 exhibited cytotoxic effect towards HL-60 and A549 cell lines with IC50 values of 3.8 and 7.2 μM, respectively.

Keywords: Aspergillus iizukae; Aspochalasin; Brasiliamide; Cytotoxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Aspergillus / chemistry*
  • Cell Proliferation*
  • Cytochalasins / chemistry*
  • Humans
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Neoplasms / pathology
  • Soil / chemistry*
  • Tumor Cells, Cultured

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Cytochalasins
  • Soil