Dioxomorpholines and Derivatives from a Marine-Facultative Aspergillus Species

J Nat Prod. 2017 Aug 25;80(8):2311-2318. doi: 10.1021/acs.jnatprod.7b00331. Epub 2017 Aug 10.

Abstract

Two new dioxomorpholines, 1 and 2, three new derivatives, 3-5, and the known compound PF1233 B (6) were isolated from a marine-facultative Aspergillus sp. MEXU 27854. Their structures were established by 1D and 2D NMR and HRESIMS data analysis. The absolute configuration of 1 and 2 was elucidated by comparison of experimental and DFT-calculated vibrational circular dichroism spectra. Compounds 3, 5, and 6 were noncytotoxic to a panel of human cancer cell lines with different functional status for the tumor-suppressor protein p53, but were inhibitors of P-glycoprotein-reversing multidrug resistance in a doxorubicin-resistant cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B / agonists*
  • ATP Binding Cassette Transporter, Subfamily B / chemistry*
  • ATP Binding Cassette Transporter, Subfamily B / metabolism
  • Aspergillus / chemistry*
  • Cell Line, Tumor
  • Circular Dichroism
  • Drug Resistance, Multiple
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • ATP Binding Cassette Transporter, Subfamily B