Phylogenetic fragrance patterns in Nicotiana sections Alatae and Suaveolentes

Phytochemistry

Volumn 67, Issue 17, 2006, Pages 1931-1942

  Raguso, Robert A ^a   Schlumpberger, Boris O ^a,b   Kaczorowski, Rainee L ^c   Holtsford, Timothy P ^c  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

^b UNIVERSITY OF MUNICH   (Germany)

^c UNIVERSITY OF MISSOURI   (United States)

Author keywords

GC MS; Hawkmoths; Headspace; Hummingbirds; Nicotiana sp.; Pollination; Solanaceae

Indexed keywords

CINEOLE; CYCLOHEXANOL DERIVATIVE; PERFUME; TERPENE;

ARTICLE; CHEMISTRY; CLASSIFICATION; FLOWER; GENETICS; MASS FRAGMENTOGRAPHY; METHODOLOGY; ODOR; PHYLOGENY; POLLEN; SPECIES DIFFERENCE; TOBACCO; VOLATILIZATION;

CYCLOHEXANOLS; FLOWERS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MONOTERPENES; ODORS; PERFUME; PHYLOGENY; POLLEN; SPECIES SPECIFICITY; TERPENES; TOBACCO; VOLATILIZATION;

MAGNOLIOPHYTA; NICOTIANA; NICOTIANA AFRICANA; NICOTIANA ALATA; NICOTIANA BONARIENSIS; NICOTIANA CAVICOLA; NICOTIANA INGULBA; NICOTIANA LANGSDORFFII; NICOTIANA LONGIFLORA; NICOTIANA PLUMBAGINIFOLIA; NICOTIANA SP.; NICOTIANA SUAVEOLENS; NICOTIANA TABACUM; SOLANACEAE; SPHINGIDAE; TROCHILIDAE;

EID: 33748660264     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2006.05.038     Document Type: Article

References (55)

1. Adams R.P. Statistical character weighting and similarity stability. Brittonia 27 (1975) 305-316
2. Adams R.P. Systematics of multi-seeded eastern hemisphere Juniperus based on leaf essential oils and RAPD DNA fingerprinting. Biochemical Systematics and Ecology 27 (1999) 709-725
3. Adams R.P., von Rudloff E., and Hogge L. Chemosystematic studies of the western North American junipers based on their volatile oils. Biochemical Systematics and Ecology 11 (1983) 189-193
4. Alston R.E., and Turner B.L. Biochemical Systematics (1963), Prentice-Hall, Inc., Englewood Cliffs, NJ
5. Azuma H., Toyota M., Asakawa Y., Yamaoka R., Garcia-Franco J.G., Dieringer G., Thien L.B., and Kawano S. Chemical divergence in floral scents of Magnolia and allied genera (Magnoliaceae). Plant Species Biology 12 (1997) 69-83
6. Baldwin I.T., Preston C., Euler M., and Gorham D. Patterns and consequences of benzyl acetone floral emissions from Nicotiana attenuata plants. Journal of Chemical Ecology 23 (1997) 2327-2343
7. Barkman T.J., Beaman J.H., and Gage D.A. Floral fragrance variation in Cypripedium: implications for evolutionary and ecological studies. Phytochemistry 44 (1997) 875-882
8. Buckler IV E.S., Ippolito A., and Holtsford T.P. The evolution of ribosomal DNA: divergent paralogues and phylogenetic implications. Genetics 145 (1997) 821-832
9. Chase M.W., Knapp S., Cox A.V., Clarkson J.J., Butsko Y., Joseph J., Savolainen V., and Parokonny A.S. Molecular systematics, GISH and the origin of hybrid taxa in Nicotiana (Solanaceae). Annals of Botany 92 (2003) 107-127
10. Colby S.M., Alonso W.R., Katahira E.J., McGarvey D.J., and Croteau R. 4S-Limonene synthase from the oil glands of spearmint (Mentha spicata). The Journal of Biological Chemistry 268 (1993) 23016-23024
11. Croft K.P.C., Jüttner F., and Slusarenko A.J. Volatile products of the lipoxygenase pathway evolved from Phaseolus vulgaris (L.) leaves inoculated with Pseudomonas syringae pv phaseolicola. Plant Physiology 101 (1993) 13-24
12. Dicke M. Local and systemic production of volatile herbivore-induced terpenoids: their role in plant-carnivore mutualism. Journal of Plant Physiology 143 (1994) 465-472
13. Dobson H.E.M., Arroyo J., Bergström G., and Groth I. Interspecific variation in floral fragrances within the genus Narcissus (Amaryllidaceae). Biochemical Systematics and Ecology 25 (1997) 685-706
14. Gäbler A., Boland W., Priess U., and Simon H. Stereochemical studies on homoterpene biosynthesis in higher plants: mechanistic, phylogenetic and ecological aspects. Helvetica Chimica Acta 74 (1991) 1773-1789
15. Gerlach G., and Schill R. Fragrance analysis, an aid to taxonomic relationships of the genus Coryanthes (Orchidaceae). Plant Systematics and Evolution 168 (1989) 159-165
16. Givnish T.J., and Sytsma K.J. Homoplasy in molecular vs. morphological data: the likelihood of correct phylogenetic inference. In: Givnish T.J., and Sytsma K.J. (Eds). Molecular Evolution and Adaptive Radiation (1997), Cambridge University Press, Cambridge, UK 55-102
17. Goodspeed T.H. The genus Nicotiana. Origins, relationships and evolution of its species in the light of their distribution, morphology and cytogenetics (1954), Chronica Botanica Co., Waltham, MA
18. Harbourne J.B. Introduction to Ecological Biochemistry (1977), Academic Press, Ltd., London
19. Hargreaves A.L., Johnson S.D., and Nol E. Do floral syndromes predict specialization in plant pollination systems? An experimental test in an "ornithophilous" African Protea. Oecologia 140 (2004) 295-301
20. Ippolito A., Fernandes G.W., and Holtsford T.P. Pollinator preferences for Nicotiana alata, N. forgetiana and their F1 hybrids. Evolution 58 (2004) 2634-2644
21. Johnson S.D. Bird pollination in South African species of Satyrium (Orchidaceae). Plant Systematics and Evolution 203 (1996) 91-98
22. Jürgens A., Webber A.C., and Gottsberger G. Floral scent compounds of Amazonian Annonaceae species pollinated by small beetles and thrips. Phytochemistry 55 (2000) 551-558
23. Jürgens A., Witt T., and Gottsberger G. Flower scent composition in Dianthus and Saponaria species (Caryophyllaceae) and its relevance for pollination biology and taxonomy. Biochemical Systematics and Ecology 31 (2003) 345-357
24. Kaczorowski R.L., Gardener M.C., and Holtsford T.P. Nectar traits in Nicotiana section Alatae (Solanaceae) in relation to floral traits, pollinators and mating system. American Journal of Botany 92 (2005) 1270-1283
25. Kaiser R. Trapping, investigation and reconstitution of flower scents. In: Müller P.M., and Lamparsky D. (Eds). Perfumes: Art, Science and Technology (1991), Elsevier Applied Science Ltd., London 213-250
26. Kaiser R. The Scent of Orchids: Olfactory and Chemical Investigations (1993), Elsevier, Amsterdam
27. Kite G.C., and Hetterschieid W.L.A. Inflorescence odours of Amorphophallus and Pseudodracontium (Araceae). Phytochemistry 46 (1997) 71-75
28. Knudsen J.T., and Mori S.A. Floral scents and pollination in Neotropical Lecythidaceae. Biotropica 28 (1996) 42-60
29. Knudsen J.T., and Ståhl B. Floral odours in the Theophrastaceae. Biochemical Systematics and Ecology 22 (1994) 259-268
30. Knudsen J.T., and Tollsten L. Trends in floral scent chemistry in pollination syndromes: floral scent composition in moth-pollinated taxa. Botanical Journal of the Linnean Society 113 (1993) 263-284
31. Knudsen J.T., Tollsten L., Groth I., Bergström G., and Raguso R.A. Trends in floral scent chemistry in pollination syndromes: floral scent composition in hummingbird-pollinated taxa. Botanical Journal of the Linnean Society 146 (2004) 191-199
32. Levin R.A., Raguso R.A., and McDade L.A. Fragrance chemistry and pollinator affinities in Nyctaginaceae. Phytochemistry 58 (2001) 429-440
33. Levin R.A., McDade L.A., and Raguso R.A. The systematic utility of floral and vegetative fragrance in two genera of Nyctaginaceae. Systematic Biology 52 (2003) 334-351
34. Mabry T.J. The order Centrospermae. Annals of the Missouri Botanical Garden 64 (1977) 210-220
35. Mabry T.J., Taylor A., and Turner B.L. The betacyanins and their distribution. Phytochemistry 2 (1962) 61-64
36. Merxmüller H., and Buttler K.P. Nicotiana in der Afrikanischen namib ein pflanzengeographisches und phylogenitisches Rätsel. Mitteilungen der Botanischen Staatssammlung München 12 (1975) 91-104
37. Negre F., Kish C.M., Boatright J., Underwood B., Shibuya K., Wagner C., Clark D.G., and Dudareva N. Regulation of methylbenzoate emission after pollination in snapdragon and petunia flowers. The Plant Cell 15 (2003) 2992-3006
38. Nogueira P.C.d.L., Bittrich V., Shepherd G.J., Lopes A.V., and Marsaioli A.J. The ecological and taxonomic importance of flower volatiles of Clusia species (Guttiferae). Phytochemistry 56 (2001) 443-452
39. Plowman, T. 1974. The South American species of Brunfelsia (Solanaceae). PhD dissertation, Harvard University, Cambridge, MA.
40. Rohloff J. Monoterpene composition of essential oil from peppermint (Mentha × piperita L.) with regard to leaf position using solid-phase microextraction and gas chromatography/mass spectrometry analysis. Journal of Agricultural and Food Chemistry 47 (1999) 3782-3786
41. Raguso R.A., and Pellmyr O. Dynamic headspace analysis of floral volatiles: a comparison of methods. Oikos 81 (1998) 238-254
42. Raguso R.A., Levin R.A., Foose S.E., Holmberg M.W., and McDade L.A. Fragrance chemistry, nocturnal rhythms and pollination "syndromes" in Nicotiana. Phytochemistry 63 (2003) 265-284
43. Rodman J.E. Divergence, convergence and parallelism in phytochemical characters: the glucosinolate-myrosinase system. In: Young D.A., and Seigler D.S. (Eds). Phytochemistry and Angiosperm Phylogeny (1979), Praeger Scientific, Inc., New York 43-79
44. Schulz S., Francke W., Edgar J., and Schneider D. Volatile components from androconial organs of Danaine and Ithomiine butterflies. Zeitschrift für Naturforsch 45c (1988) 99-104
45. Seigler D.S. Terpenes and plant phylogeny. In: Young D.A., and Seigler D.S. (Eds). Phytochemistry and Angiosperm Phylogeny (1979), Praeger Scientific, Inc., New York 117-148
46. SPSS Inc., 1999. SPSS for Windows, version 10.0.5. SPSS Inc., Chicago.
47. Stehmann J.R., Semir J., and Ippolito A. Nicotiana mutabilis (Solanaceae), a new species from southern Brazil. Kew Bulletin 57 (2002) 639-646
48. Svensson G.P., Hickman M.O., Bartram S., Boland W., Pellmyr O., and Raguso R.A. Chemistry and geographic variation of floral scent in Yucca filamentosa (Agavaceae). American Journal of Botany 92 (2005) 1624-1631
49. Tabacchi, R., Garnero, J., Quellet, C. Tsoupras, G., 1986. Study of the essential oil of Buddleja salvifolia (River Plant). In: Lawrence, B.M., Mookherjee, B.D., Willis, B.J. (Eds.), Flavors and Fragrances, a World Perspective. Proceedings of the 10th International Congress of Essential Oils, Fragrances and Flavors. Washington, DC.
50. Tadmor-Melamed H., Markman S., Arieli A., Distl M., Wink M., and Izhaki I. Limited ability of Palestine Sunbirds Nectarinia osea to cope with pyridine alkaloids in nectar of Tree Tobacco, Nicotiana glauca. Functional Ecology 18 (2004) 844-850
51. Weiss M.R. Floral color change: a widespread functional convergence. American Journal of Botany 82 (1995) 167-185
52. Williams N.H., and Whitten W.M. Molecular phylogeny and floral fragrances of male euglossine bee-pollinated orchids: a study of Stanhopea (Orchidaceae). Plant Species Biology 14 (1999) 129-136
53. Wise M.L., Savage T.J., Katahira E., and Croteau R. Monoterpene synthases from common sage (Salvia officinalis). The Journal of Biological Chemistry 273 (1998) 14891-14899
54. Zhang Z.H., and Pawliszyn J. Headspace solid-phase microextraction. Analytical Chemistry 65 (1993) 1843-1852
55. Zuker A.T., Tzfira T., Ben-Meir H., Ovadis M., Shklarman E., Itzhaki H., Forkmann G., Martens S., Neta-Sharir J., Weiss D., and Vainstein A. Modification of flower color and fragrance by antisense suppression of the flavanone 3-hydroxylase gene. Molecular Breeding 9 (2002) 33-41