Floral fragrance chemistry in the early flowering shrub Daphne mezereum

• Published in: Phytochemistry (Oxford) Vol. 41; no. 6; pp. 1477 - 1483
• Main Authors: Borg-Karlson, Anna-Karin, Unelius, C.Rikard, Valterová, Irena, Anders Nilsson, L.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.04.1996; Elsevier
• Subjects: (s)-(+)-linalool; andrena; Andrenidae; Biological and medical sciences; Chemical constitution; chirality; colletes; Colletidae; Daphne mezereum; Ecological chemistry; Ekologisk kemi; enantiomer; floral fragrance; Fundamental and applied biological sciences. Psychology; linalool oxides; ocimene; orchidaceae; Plant physiology and development; pollination; thymelaeaceae; linalool oxides; chirality; Thymelaeaceae; pollination; Colletes; Daphne mezereum; enantiomer; floral fragrance; ocimene; Andrena; ( S)-(+)-linalool; Terpenoid; Flower; Insect pollination; Molecular structure; Dicotyledones; Chirality; Enantiomer; Perfume; Angiospermae; Spermatophyta; Chemical composition; (S)-(+)-linalool; ORCHIDACEAE
• ISSN: 0031-9422; 1873-3700; 1873-3700
• DOI: 10.1016/0031-9422(95)00801-2

The floral fragrance of the shrub Daphne mezereum in central Sweden was collected by means of the head-space technique and investigated by GC-MS and multi-dimensional GC. ( S)-(+)-Linalool was the main constituent (95%) of the flower fragrance and its enantiomeric purity exceeded 99% in the samples. The (2 S, 5 S)- and (2 R, 5 S)-furanoid and the (3 R, 6 S)- and (3 S, 6 S)-pyranoid linalool oxide isomers constituted 2–5% of the fragrance. The elution order of these compounds on a permethylated β-cyclodextrin column is reported. A fragrance sample of D. mezereum as well as ( S)-(+)-linalool attracted males of the vernal solitary bee species Colletes cunicularius and Andrena cinerea. A racemic mixture of the two enantiomeric pairs of known furanoid linalool oxides was only weakly attractive to the bees. The role of the fragrance in the pollination specialization of the plant is discussed.