Penigrisacids A-D, Four New Sesquiterpenes from the Deep-Sea-Derived Penicillium griseofulvum

Mar Drugs. 2019 Aug 29;17(9):507. doi: 10.3390/md17090507.

Abstract

Four new (penigrisacids A-D, 1-4) and one known (5) carotane sesquiterpenoids were isolated from the deep-sea-derived fungus Penicillium griseofulvum, along with four known compounds (6-9). The planar structures and relative configurations of the new compounds were determined by extensive analysis of the NMR and HRESIMS data. The absolute configurations were established by comparison of the experimental and calculated ECD (electronic circular dichroism) spectra or OR (optical rotation) value. Compound 9 exhibited potent anti-food allergic activity with IC50 value of 28.7 μM, while 4 showed weak cytotoxicity against ECA-109 tumor cells (IC50 = 28.7 μM).

Keywords: Penicillium griseofulvum; anti-food allergy; carotanes; deep-sea-derived fungus; sesquiterpenes.

MeSH terms

  • Aquatic Organisms / chemistry*
  • Cell Line, Tumor
  • Circular Dichroism
  • HeLa Cells
  • Humans
  • Magnetic Resonance Spectroscopy / methods
  • Oceans and Seas
  • Penicillium / chemistry*
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology

Substances

  • Sesquiterpenes