Resorcinosides A and B, Glycosylated Alkylresorcinols from a Marine-Derived Strain of the Fungus Penicillium janthinellum

J Nat Prod. 2019 Nov 22;82(11):3186-3190. doi: 10.1021/acs.jnatprod.9b00776. Epub 2019 Oct 31.

Abstract

Two new glycosylated alkylresorcinols, resorcinosides A (1) and B (2), were isolated from a strain of the fungus Penicillium janthinellum derived from a marine sediment sample collected from Cu Lao Cham Island, Vietnam. The structures of 1 and 2 were established by interpretation of 1D and 2D NMR and high-resolution ESIMS data, and their absolute configurations were confirmed by the coupling constant of the anomeric proton, acid hydrolysis, subsequent HPLC analysis, Mosher's method, and quantum-mechanics-based computational analysis of NMR chemical shifts. The structure elucidation indicated that 1 and 2 are new alkylresorcinols with d-glucose, and 2 has an α-pyrone moiety attached to the aromatic ring. Compound 1 exhibited cytotoxic activity against the NUGC-3 cancer cell line with a GI50 value of 9.3 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / pharmacology
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Penicillium / chemistry*
  • Resorcinols / chemistry*
  • Resorcinols / pharmacology*
  • Seawater / microbiology
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Antibiotics, Antineoplastic
  • Resorcinols