Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica

J Nat Prod. 2001 Dec;64(12):1527-32. doi: 10.1021/np010370g.

Abstract

Six new ellagitannins, phyllanemblinins A-F (1-6), were isolated from Phyllanthus emblica, along with 30 known tannins and related compounds. Their structures were determined by spectral and chemical methods. Phyllanemblinins A (1) and B (2) were confirmed to be ellagitannins having a tetrahydroxybenzofuran dicarboxyl group and a hexahydroxydiphenoyl group, respectively, by chemical synthesis from furosin (8). Phyllanemblinin C (3) has a new acyl group at the glucose 2,4-positions and is structurally related to chebulagic acid. Phyllanemblinins D (4), E (5), and F (6) were found to be positional isomers of neochebuloyl 1(beta)-O-galloylglucose.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Chemical Phenomena
  • Chemistry, Physical
  • Chromatography, Thin Layer
  • Circular Dichroism
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal
  • Euphorbiaceae / chemistry*
  • Fruit / chemistry
  • HL-60 Cells / drug effects
  • HeLa Cells / drug effects
  • Humans
  • Hydrolyzable Tannins*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Stereoisomerism
  • Tannins / chemistry
  • Tannins / isolation & purification*
  • Tannins / pharmacology
  • Tumor Cells, Cultured / drug effects

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Hydrolyzable Tannins
  • Tannins
  • ellagitannin