Isolation of (S)-(−)-2,3-Dihydro-2,6-dimethyl-4H-benzopyran-4-one from Roots of Leontopodium alpinum

• Published in: Journal of natural products (Washington, D.C.) Vol. 60; no. 2; pp. 148 - 149
• Main Authors: Comey, Neil, Hook, Ingrid, Sheridan, Helen, Walsh, John, James, Paraic
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 21.02.1997; Glendale, AZ American Society of Pharmacognosy
• Subjects: ACEITES ESENCIALES; AGROBACTERIUM RHIZOGENES; Biological and medical sciences; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; COMPOSE VOLATIL; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; COMPUESTO VOLATIL; ESPECTROMETRIA; ESSENTIAL OILS; ESTRUCTURA QUIMICA; General pharmacology; HUILE ESSENTIELLE; LEONTOPODIUM; Medical sciences; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; PLANTAS TRANSGENICAS; PLANTE TRANSGENIQUE; RACINE; RAICES; ROOTS; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; STRUCTURE CHIMIQUE; TRANSGENIC PLANTS; VOLATILE COMPOUNDS; Alps; Europe; Root; Pharmacognosy; Compositae; Oxygen heterocycle; Ketone; Medicinal plant; Dicotyledones; Angiospermae; Plant origin; Bicyclic compound; S configuration; Isolation; Spermatophyta; Aromatic compound; Structural analysis; Enantiomer(-)
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960228t

The isolation of (S)-(−)-2,3-dihydro-2,6-dimethyl-4H-benzopyran-4-one (1) from the essential oil produced by natural roots and also from genetically transformed (“hairy”) root cultures of Leontopodium alpinum is described. This is the first reported natural occurrence of 1. Structural assignments were made on the basis of spectroscopic data and by comparison with a synthetic sample.