Extensive 1D, 2D NMR Spectra of Some [7.0]Metacyclophanes and X-ray Analysis of (±)-Myricanol

From the hexane extract of the bark of Myrica cerifera, the pentacyclic triterpenes taraxerol and myricadiol were isolated. The EtOH extract afforded the [7.0]metacyclophanes, (±)-myricanol (4), and myricanone (7). Accurate 1H- and 13C-NMR spectral assignments have been made for (±)-myricanol (4), 5...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1996-08, Vol.59 (8), p.759-764
Main Authors: Joshi, Balawant S, Pelletier, S. William, Newton, M. Gary, Lee, Doowon, McGaughey, Georgia B, Puar, Mohindar S
Format: Article
Language:English
Subjects:
ANALYTICAL METHODS
BARK
Biological and medical sciences
CHEMICAL COMPOSITION
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
CORTEZA
DRUG PLANTS
ECORCE
ESPECTROMETRIA
ESPECTROSCOPIA RMN
General pharmacology
Medical sciences
MYRICA
MYRICA CERIFERA
myricadiol
NMR SPECTROSCOPY
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
PLANTAS MEDICINALES
PLANTE MEDICINALE
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
SPECTROSCOPIE RMN
taraxerol
TECHNIQUE ANALYTIQUE
TECNICAS ANALITICAS
TRITERPENOIDE
TRITERPENOIDOS
TRITERPENOIDS
X RAY DIFFRACTION
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Summary:From the hexane extract of the bark of Myrica cerifera, the pentacyclic triterpenes taraxerol and myricadiol were isolated. The EtOH extract afforded the [7.0]metacyclophanes, (±)-myricanol (4), and myricanone (7). Accurate 1H- and 13C-NMR spectral assignments have been made for (±)-myricanol (4), 5,11,17-tri-O-acetyl-(±)-myricanol (5), 11-O-methyl-(±)-myricanol (6), and myricanone (7) by a study of the 1H−H-COSY, 1H−13C-COSY (HETCOR), selective INEPT, and 1D NOE experiments. The structure of (±)-myricanol was established by a single crystal X-ray analysis. Molecular mechanics MM-3(94) calculations have been made for (R,Sa)- and (S,Sa)-myricanol, and the bond lengths, bond angles, and the torsion angles have been calculated for the energy-minimized conformation.
ISSN:0163-3864
1520-6025
DOI:10.1021/np960230k