Melongenaterpenes A-L, Vetispirane-Type Sesquiterpenoids from the Roots of Solanum melongena

J Nat Prod. 2019 Dec 27;82(12):3242-3248. doi: 10.1021/acs.jnatprod.9b00206. Epub 2019 Nov 19.

Abstract

Melongenaterpenes A-L (1-12), 12 new sesquiterpenoids with rare spiro[4.5]decane skeletons, were isolated from the roots of Solanum melongena. Their 2D structures and relative configurations were determined based on NMR and HRESIMS data. The absolute configuration of melongenaterpene A (1) was defined by X-ray crystallographic analysis. The absolute configurations of the remaining compounds were determined by comparison of their NMR data with 1 and consideration of the biosynthetic pathway. This is the first report of the crystal structure of a vetispirane-type sesquiterpenoid. None of the compounds exhibited cytotoxic activity against the three human cancer cell lines HepG2, HeLa, and MCF-7.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Crystallography, X-Ray
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • MCF-7 Cells
  • Molecular Structure
  • Plant Roots / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Solanum melongena / chemistry*
  • Spectrum Analysis / methods

Substances

  • Antineoplastic Agents, Phytogenic
  • Sesquiterpenes