Floral Fragrances. P. Hugueney, ENSL
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1 Floral Fragrances P. Hugueney, ENSL
2 What is flower scent?
3 Flower scent analysis :"dynamic headspace chromatography" filter container trap pump flower attached to plant 1 : sampling
4 Flower scent analysis using "headspace chromatography" trap Gas Chromatography Mass Spectroscopy 2 :analysis
5 More than 100 different volatile compounds are detected in the scent of a single rose flower CH 3 COOCH 3 CH 3 COOCH 3 H 3 CO OCH 3 OCH 3 H 3 CO OCH 3 COOCH 3 COOCH 3 COOCH 3 COOCH 3 COOCH 3 CH 3 OCH 3 H 3 CO OCH 3
6 The reason why flowers are scented...
7 Olfactory organ of insects : the antenna Antenna : contains olfactory neurons V electroantennography : detection of neuron membrane depolarization
8 V GC-EAD Gas Chromatography with ElecroAntennographic Detection
9 Sex pheromone mimicry in the orchid Ophrys sphegodes Schiestl et al. (2000), J. Comp. Physiol. A 186 :
10 Flower scent analysis by " nose detection"
11 A "pleasant" scent is relative.
12 Understanding scent compounds biosynthesis CH 3 COOCH 3 CH 3 COOCH 3 H 3 CO OCH 3 OCH 3 H 3 CO OCH 3 COOCH 3 COOCH 3 COOCH 3 COOCH 3 COOCH 3 CH 3 OCH 3 H 3 CO OCH 3
13 Understanding scent compounds biosynthesis = Organizing scent compounds into metabolic pathways Major classes of flower scent compounds : - Terpenes - Aromatic compounds - Fatty acid derivatives
14 Terpenes (25000 natural compounds) geraniol carotenoids Isopentenyl pyrophosphate linalool sterols OPP limonene chlorophyll H Primary metabolism (-) menthol H H β-pinene
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16 Most advanced models : - Peppermint (Mentha x piperata) : Rodney Croteau Photo : J.C. Caissard - Clarkia breweri : Eran Pichersky (about 10 scent genes cloned...) Photo : J. D'Auria
17 A more recent but very promising model : the rose Rosa x damascena essential oil : tons oil / year : /kg : 4 tons petals (800h) for 1kg oil Rosa x centifolia ( Rose de Mai ) - grown in the south of France (Grasses) : 350 tons of flowers - used in some perfumes
18 What is a rose? - Rosa x hybrida : initial crosses involving less than 10 wild rose species - more than 2 centuries of breeding and selection - about registered varieties - most economically important ornamental plant
19 Rosa gallica Rosa phoenicia Rosa moschata Rosa chinensis cv. Old Blush R. moschata R. damascena R. bifera R. chinensis R. gigantea Noisette Roses R. odorata Bourbon Roses R. gallica R. odorata Yellow Tea Roses Pink Tea Roses R. bifera R. gallica Bourbon Roses Chinese Hybrids Portland Roses Tea Scented Roses Hybrid Perpetual Roses Hybrid Tea Roses Modern Roses Modern roses genealogy
20 Interest of crossing "European" and "Chinese" Roses "European" Roses : ex : Rosa gallica, Rosa x damascena - temperate climate - yearly flowering in May "Chinese" Roses : ex : Rosa chinensis - subtropical climate - recurrent flowering
21 Modern hybrid roses : - temperate climate - recurrent flowering - selection of aesthetic traits wild rose modern rose
22 Rose scent Terpenes Phenylethanol Aromatic compounds Fatty acid derivatives Rose ketones etc... Secretory epidermis
23 pa nerol phenylethanol Citronellol Geraniol GC analysis of R. x damascena scent min
24 2 main types of scent in "wild" roses "European" Type : ex : Rosa x damascena - phenylethanol - monoterpenes Geraniol Citronellol 2-phenylethanol nerol
25 2 main types of scent in "wild" roses "Chinese" Type : ex : Rosa chinensis, Rosa gigantea - monoterpenes - fatty acid derivatives - phenolic compounds OCH3 cis-3-hexenol CH3O trimethoxybenzene OCH3 geraniol
26 modern roses scent... "Combined" Type : 2-phenylethanol Geraniol CH 3 Citronellol H 3 CO OCH 3 3,5-dimethoxytoluene nerol
27 modern roses scent... "Scentless" Type : pa Royal Red 2-ph nyl thanol min
28 Why are many modern roses scentless? This trait was lost in recent breeding processes, with selection programs based on shape, colour, disease resistance, longevity...
29 Characterization of genes and enzymes involved in scent production in roses - 2 years ago : 20 rose sequences in gene databases - Genomic approach : random sequencing of genes expressed in rose petals Channelière et al., 2002 Guterman et al., 2002
30 Functional classification of the rose petal ESTs Primary metabolism (6.6%) No blast hit (26.6%) RNA binding (0.9%) Secondary metabolism (2.6%) Protein synthesis (5.1%) Protein and lipid turnover (2.4%) Cell wall (1.9%) Secreted proteins (2.8%) Membrane associated (10.9%) Hormone regulated (1.9%) Unknown function (9.2%) Other (8.6%) Defense / stress related (15.1%) Signal transduction (4.0%) Transcription (1.2%)
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37 Detection thresholds (ppb) (human) ß-ionone ß-damascenone (1 µl / 100 m 3 ) ß-ionone ß-damascenone Linalool 6 Citronellol 40 Geraniol 75 Linalool Citronellol Geraniol
38 Alister Stella Gray (Noisette)
39 Rose ketones biosynthesis Carotenoids carotenoiddioxygenase oxidative clivage O O Rose ketones : - ß-ionone - ß-damascenone
40 Carotenoid cleavage in mammals β- carotene symetric cleavage asymetric cleavage β- apocarotenal retinal retinoic acid β- ionone
41 Plant Reproduction and Development (C.Dumas), CNRS,INRA,ENSL,UCBL The "Rose" lab G. Scalliet P. Hugueney M. Cock M. Bendahmane The "Rose" lab in St Etienne S. Baudino F. Jullien J.L. Magnard V. Bergougnoux S. Channelière P. Vergne C. Dolle J. Szecsi
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