Chemical constituents from Hericium erinaceus and their ability to stimulate NGF-mediated neurite outgrowth on PC12 cells

Bioorg Med Chem Lett. 2015 Nov 15;25(22):5078-82. doi: 10.1016/j.bmcl.2015.10.016. Epub 2015 Oct 16.

Abstract

One new meroterpenoid, named hericenone K (11), along with 10 known compounds (1-10), ergosterol peroxide (1), cerevisterol (2), 3β,5α,9α-trihydroxy-ergosta-7,22-dien-6-one (3), inoterpene A (4), astradoric acid C (5), betulin (6), oleanolic acid (7), ursolic acid (8), hemisceramide (9), and 3,4-dihydro-5-methoxy-2-methyl-2-(4'-methyl-2'-oxo-3'-pentenyl)-9(7H)-oxo-2H-furo[3,4-h]benzopyran (10), was isolated from the fruiting bodies of the mushroom Hericium erinaceus. Their structures were characterized on the basis of spectroscopic methods, as well as through comparison with previously reported data. Compounds 3-6, 8, and 9 were isolated from Hericium species for the first time. Compounds 10 and 11 was suggested to be racemic by the CD spectrum data and specific rotations, which ware resolved by chiral HPLC into respective enantiomers. Compounds 1-3, (±)-10, (-)-10 and (+)-10 in the presence of NGF (20 ng/mL) exerted a significant increase in neurite-bearing cells.

Keywords: Hericium erinaceus; Meroterpenoid; NGF-mediated PC12 cells; Natural products; Neurite outgrowth-promoting activity; Neuroactives; Prenylated benzopyran; TDDFT.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / chemistry*
  • Animals
  • Ceramides / isolation & purification
  • Ceramides / pharmacology
  • Ergosterol / analogs & derivatives*
  • Ergosterol / isolation & purification
  • Ergosterol / pharmacology
  • Fruiting Bodies, Fungal / chemistry
  • Monoterpenes / isolation & purification
  • Monoterpenes / pharmacology
  • Nerve Growth Factors / pharmacology*
  • Neurites / drug effects*
  • Neurites / physiology
  • PC12 Cells
  • Phytosterols / isolation & purification
  • Phytosterols / pharmacology*
  • Rats
  • Stereoisomerism
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology

Substances

  • Ceramides
  • Monoterpenes
  • Nerve Growth Factors
  • Phytosterols
  • Triterpenes
  • hemisceramide
  • cerevisterol
  • ergosterol-5,8-peroxide
  • Ergosterol