Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, Isolated from Silybum marianum (milk thistle)

J Nat Prod. 2003 Sep;66(9):1171-4. doi: 10.1021/np030163b.

Abstract

Two pairs of diastereoisomeric flavonolignans, silybin A, silybin B, isosilybin A, and isosilybin B, were successfully separated from Silybum marianum by sequential silica gel column chromatography, preparative reversed-phase HPLC, and recrystallization. Complete stereochemical assignments at C-2, C-3, C-7', and C-8' of these flavonolignans have been achieved. On the basis of X-ray crystallographic analysis and optical rotation data, coupled with comprehensive (1)H and (13)C NMR spectral data interpretation including COSY, HMQC, and HMBC, the stereochemistry of these diastereoisomers was determined unambiguously as silybin A (4), 2R, 3R, 7'R, 8'R; silybin B (5), 2R, 3R, 7'S, 8'S; isosilybin A (6), 2R, 3R, 7'R, 8'R; and isosilybin B (7), 2R, 3R, 7'S, 8'S.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Drugs, Chinese Herbal / chemistry*
  • Milk Thistle / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Seeds / chemistry
  • Silybin
  • Silymarin / analogs & derivatives*
  • Silymarin / chemistry*
  • Stereoisomerism
  • X-Ray Diffraction

Substances

  • Drugs, Chinese Herbal
  • Silymarin
  • Silybin
  • isosilybin