Dioxomorpholines and Derivatives from a Marine-Facultative Aspergillus Species.

J Nat Prod

Departamento de Química, Centro de Investigación y de Estudios, Avanzados del Instituto Politécnico Nacional , Apartado 14-740, Ciudad de México 07000, México.

Published: August 2017


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Article 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.

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http://dx.doi.org/10.1021/acs.jnatprod.7b00331DOI Listing

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Dioxomorpholines and Derivatives from a Marine-Facultative Aspergillus Species.

J Nat Prod

August 2017

Departamento de Química, Centro de Investigación y de Estudios, Avanzados del Instituto Politécnico Nacional , Apartado 14-740, Ciudad de México 07000, México.

Article Synopsis
  • Two new compounds, dioxomorpholines 1 and 2, along with three derivatives (3-5) and the known compound PF1233 B (6), were extracted from a marine Aspergillus species.
  • The structural identification of these compounds was achieved using advanced NMR and HRESIMS techniques, with the absolute configuration of 1 and 2 determined through vibrational circular dichroism spectra analysis.
  • While compounds 3, 5, and 6 showed no toxicity to various human cancer cell lines, they were effective in inhibiting P-glycoprotein, which helps counteract multidrug resistance, particularly in doxorubicin-resistant cells.
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