Daturametelins H, I, and J: three new withanolide glycosides from Datura metel L

Chem Biodivers. 2006 Feb;3(2):180-6. doi: 10.1002/cbdv.200690021.

Abstract

Three new withanolide glycosides named daturametelins H-J (1-3), together with two known ones, daturataturin A (4) and 7,27-dihydroxy-1-oxowitha-2,5,24-trienolide (5), were isolated from the MeOH extract of the aerial parts of Datura metel L. (Solanaceae). Their structures were determined mainly by spectroscopic techniques including 2D-NMR (HMBC, HMQC, (1)H,(1)H-COSY, NOESY) and MS experiments. Compounds 1-5 were tested for their antiproliferative activity towards the human colorectal carcinoma (HCT-116) cell line. The nonglycosidic compound 5 exhibited the highest activity of the tested withanolides, with an IC(50) value of 3.2+/-0.2 microM (Table 3).

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Survival / drug effects
  • Datura*
  • Drug Screening Assays, Antitumor / methods
  • Ergosterol / chemistry
  • Ergosterol / isolation & purification*
  • Ergosterol / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • HCT116 Cells
  • Humans
  • Plant Components, Aerial
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*
  • Plant Extracts / pharmacology
  • Withania*

Substances

  • Antineoplastic Agents, Phytogenic
  • Glycosides
  • Plant Extracts
  • Ergosterol