Polyoxygenated Cyclohexenoids with Promising α-Glycosidase Inhibitory Activity Produced by Phomopsis sp. YE3250, an Endophytic Fungus Derived from Paeonia delavayi

J Agric Food Chem. 2018 Feb 7;66(5):1140-1146. doi: 10.1021/acs.jafc.7b04998. Epub 2018 Jan 30.

Abstract

Seven new polyoxygenated cyclohexenoids, namely, phomopoxides A-G (1-7), were isolated from the fermentation broth extract of an endophytic fungal strain Phomopsis sp. YE3250 from the medicinal plant Paeonia delavayi Franch. The structures of these compounds were established by spectroscopic interpretation. The absolute configurations of compounds 1 and 4 were confirmed by X-ray crystallographic analysis and chemical derivative approach. All isolated compounds showed weak cytotoxic activities toward three human tumor cell lines (Hela, MCF-7, and NCI-H460) and weak antifungal activities against five pathogenic fungi (Candida albicans, Aspergillus niger, Pyricularia oryzae, Fusarium avenaceum, and Hormodendrum compactum). In addition, compounds 1-7 showed a promising α-glycosidase inhibitory activity with IC50 values of 1.47, 1.55, 1.83, 2.76, 2.88, 3.16, and 2.94 mM, respectively, as compared with a positive control of acarbose (IC50 = 1.22 mM).

Keywords: Paeonia delavayi; Phomopsis; polyoxygenated cyclohexenoids; α-glucosidase inhibitor.

MeSH terms

  • Antifungal Agents
  • Antineoplastic Agents
  • Ascomycota / metabolism*
  • Cell Line, Tumor
  • Cyclohexanes / chemistry
  • Cyclohexanes / pharmacology*
  • Endophytes / metabolism
  • Enzyme Inhibitors*
  • Glycoside Hydrolases / antagonists & inhibitors*
  • HeLa Cells
  • Humans
  • MCF-7 Cells
  • Oxygen / chemistry
  • Paeonia / microbiology*
  • Plants, Medicinal / microbiology

Substances

  • Antifungal Agents
  • Antineoplastic Agents
  • Cyclohexanes
  • Enzyme Inhibitors
  • Glycoside Hydrolases
  • Oxygen