Flavonoid glucuronides and a chromone from the aquatic macrophyte Stratiotes aloides

J Nat Prod. 2009 May 22;72(5):835-40. doi: 10.1021/np800769g.

Abstract

The first phytochemical analysis of the aquatic macrophyte Stratiotes aloides afforded two new flavonoid glucuronides, luteolin 7-O-beta-D-glucopyranosiduronic acid-(1-->2)-beta-D-glucopyranoside (1) and chrysoeriol 7-O-beta-D-glucopyranosiduronic acid-(1-->2)-beta-D-glucopyranoside (2), as well as the new 2-(2-hydroxypentyl)-5-carboxy-7-methoxychromone (5) and chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside (3), which has been assigned via NMR data for the first time. Additionally, free amino acids such as tryptophan, arginine, leucine, isoleucine, phenylalanine, and tyrosine along with choline, cis-aconitic acid, the phenolic glycoside alpha-arbutine, the chlorophyll derivative phaeophorbide a, and the flavonoid glycoside luteolin 7-O-beta-(6-O-malonyl)glucopyranoside (4) were isolated. Despite the low quantities obtained in some cases (between 50-300 microg), the structures of all compounds were unambiguously elucidated by extensive NMR and MS experiments. With a delay of 2 days compound 1 (10 and 50 microM test concentration) strongly inhibited the growth of human SH-SY5Y neuroblastoma cells in a dose-dependent manner, whereas only a moderate growth inhibition of human Patu 8902 carcinoma cells could be observed. Compounds 1 and 2 showed no activities against the bacteria Escherichia coli BW25113, Pseudomonas pudida KT2440, and Enterobacter cloacae subsp. dissolvens.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Chromones / chemistry
  • Chromones / isolation & purification*
  • Chromones / pharmacology
  • Drug Screening Assays, Antitumor
  • Enterobacter cloacae / drug effects
  • Escherichia coli / drug effects
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Fresh Water
  • Germany
  • Glucosides
  • Glucuronides / chemistry
  • Glucuronides / isolation & purification*
  • Glucuronides / pharmacology
  • Humans
  • Hydrocharitaceae / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Pseudomonas putida / drug effects
  • Stereoisomerism
  • Triterpenes

Substances

  • 2-(2-hydroxypentyl)-5-carboxy-7-methoxychromone
  • Antineoplastic Agents, Phytogenic
  • Chromones
  • Flavonoids
  • Glucosides
  • Glucuronides
  • Triterpenes
  • cucurbitacin G 2-O-beta-D-glucopyranoside
  • luteolin 7-O-beta-D-glucopyranosiduronic acid-(1-2)-beta-D-glucopyranoside