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

• Published in: Journal of natural products (Washington, D.C.) Vol. 59; no. 8; pp. 759 - 764
• Main Authors: Joshi, Balawant S, Pelletier, S. William, Newton, M. Gary, Lee, Doowon, McGaughey, Georgia B, Puar, Mohindar S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.08.1996; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: ANALYTICAL METHODS; BARK; Biological and medical sciences; CHEMICAL COMPOSITION; Chemistry, Medicinal; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; CORTEZA; DRUG PLANTS; ECORCE; ESPECTROMETRIA; ESPECTROSCOPIA RMN; General pharmacology; Life Sciences & Biomedicine; Medical sciences; MYRICA; MYRICA CERIFERA; myricadiol; NMR SPECTROSCOPY; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; PLANTAS MEDICINALES; PLANTE MEDICINALE; Science & Technology; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; SPECTROSCOPIE RMN; taraxerol; TECHNIQUE ANALYTIQUE; TECNICAS ANALITICAS; TRITERPENOIDE; TRITERPENOIDOS; TRITERPENOIDS; X RAY DIFFRACTION; United States; North America; America; MYRICA-RUBRA; SEPARATION; Pharmacognosy; Bark; Theoretical study; Tricyclic compound; Macrocycle; Medicinal plant; Ketophenols; Folk medicine; Dicotyledones; Angiospermae; Force field method; Phenols; Racemate; Isolation; Spermatophyta; Cyclophane; Secondary alcohol; Acylate; Diastereomer; Structural analysis; Myricaceae
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960230k

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.