Lanostane triterpenoids from Ganoderma luteomarginatum and their cytotoxicity against four human cancer cell lines

Phytochemistry. 2018 Dec:156:89-95. doi: 10.1016/j.phytochem.2018.09.003. Epub 2018 Sep 18.

Abstract

Lanostane triterpenoids are major metabolites of macrofungi from the genus Ganoderma and possess enormous substitution diversity and remarkable biological activities, especially anticancer, antioxidant, and anti-inflammatory effects. The present phytochemical investigation resulted in the isolation of nine undescribed lanostane triterpenoids and five known analogues from the fruiting bodies of Ganoderma luteomarginatum, which was first phytochemically studied by our group. Chemical structures were elucidated based on spectroscopic evidence. (5α,23E)-27-nor-lanosta-8,23-dien-3,7,25-trione and (5α,23E)-27-nor-3β-hydroxylanosta-8,23-dien-7,25-dione are undescribed triterpenoids with an unusual 27-nor-lanostane carbon skeleton. All isolates were assayed for their cytotoxic activities using four human cancer cell lines (HGC-27, HeLa, A549, and SMMC-7721) and one human normal cell line (LO2), and the structure-cytotoxicity relationships were preliminarily explored. (5α,24E)-3β-acetoxyl-26-hydroxylanosta-8,24-dien-7-one exhibited the highest cytotoxicity against HeLa and A549 cell lines, with IC50 values of 1.29 and 1.50 μM, respectively.

Keywords: 27-nor-Lanostane carbon skeleton; Cytotoxicity; Ganoderma luteomarginatum; Ganodermataceae; Lanostane triterpenoids.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fruiting Bodies, Fungal / chemistry*
  • Ganoderma / chemistry*
  • Humans
  • Molecular Conformation
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Triterpenes