Triterpenoids and an alkamide from Ganoderma tsugae

Fitoterapia. 2016 Jan:108:73-80. doi: 10.1016/j.fitote.2015.11.003. Epub 2015 Nov 18.

Abstract

Ganoderma tsugae is a medicinal mushroom. In a continual study on the bioactive constituents of this fungus, a new lanostanoid, 3β-acetoxy-16α-hydroxy-24ξ-methyl-5α-lanosta-8,25-dien-21-oic acid, named tsugaric acid F (1) and a novel palmitamide, N-(3'α,4'β-dihydroxy-2'β-(hydroxymethyl)-1'β-(cyclobutyl)palmitamide (2) were isolated and characterized from the fruit bodies of G. tsugae, and three novel seco-lanostanoids, 3,4-seco-8α,9α-epoxy-5α-lanosta-21-oic acid 3,4 lactone (5), 3,4-seco-5β-lanosta-7,9(11),4(29)-trien-3,21-dioic acid-3-methyl ester (6), 3,4-seco-5β-lanosta-7,9(11),4(29)-trien-3,21-dioic acid (7), and a known compound, 3-oxo-5α-lanosta-8-en-21-oic acid (4) were prepared from 3. The structures of new compounds, 1, 2, 5-7 were determined by spectroscopic methods. Compounds 1 and 4 showed inhibitory effects on xanthine oxidase (XO) with an IC50 values of 313.3 ± 80.0 and 43.9 ± 29.9 μM, respectively when 7 exhibited potent inhibitory effect on superoxide anion generation in rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB) with an IC50 values of 1.3 ± 0.2 μM. Compounds 4-7 showed weak cytotoxic activities against PC3 cells. These results indicated that 4 and 7 may be used as cancer chemopreventive agents.

Keywords: Anti-inflammatory; Antioxidant; Cytotoxicity; Ganoderma tsugae; Lanostanoid; Seco-lanostanoid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / chemistry
  • Amides / chemistry*
  • Amides / isolation & purification
  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Cell Line, Tumor
  • Ganoderma / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Mice
  • Molecular Structure
  • Neutrophils / drug effects
  • RAW 264.7 Cells
  • Rats
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Xanthine Oxidase / antagonists & inhibitors

Substances

  • Amides
  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Triterpenes
  • Xanthine Oxidase