Phallac acids A and B, new sesquiterpenes from the fruiting bodies of Phallus luteus

J Antibiot (Tokyo). 2020 Oct;73(10):729-732. doi: 10.1038/s41429-020-0328-z. Epub 2020 May 29.

Abstract

Phallus luteus (Phallaceae), previously known as Dictyophora indusiata, is an edible and medicinal mushroom. As part of a continuing project to discover structurally and/or biologically novel natural products from wild mushrooms, we aimed to perform a chemical investigation of the methanol extract of P. luteus combined with a liquid chromatography-mass spectrometry-guided analysis coupled to an in-house UV spectral library. Two new sesquiterpenes, phallac acids A (1) and B (2), were isolated and determined. The chemical structure of the new natural products was unambiguously determined using a combination of 1D and 2D NMR and high-resolution electrospray ionization mass spectrometry data. To our knowledge, this is the first study to report linear sesquiterpene carboxylic acids from P. luteus. The new compounds were evaluated for α-glucosidase inhibitory activities where phallac acid B (2) showed α-glucosidase inhibitory potential (IC50 value of 94.89 ± 5.57 μM) compared with the standard acarbose (IC50 value of 26.23 ± 1.31 μM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Basidiomycota / chemistry*
  • Fruiting Bodies, Fungal / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / isolation & purification*
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Glycoside Hydrolase Inhibitors
  • Sesquiterpenes

Supplementary concepts

  • Dictyophora indusiata