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Communication

Volatile Organic Compounds in Dactylorhiza Species

by
Marisabel Mecca
1,
Rocco Racioppi
1,
Vito Antonio Romano
1,
Licia Viggiani
1,
Richard Lorenz
2 and
Maurizio D’Auria
1,*
1
Dipartimento di Scienze, Università della Basilicata, V.le dell’Ateneo Lucano 10, 85100 Potenza, Italy
2
AHO Baden-Württemberg, 64686 Lautertal, Germany
*
Author to whom correspondence should be addressed.
Compounds 2022, 2(2), 121-130; https://doi.org/10.3390/compounds2020009
Submission received: 21 February 2022 / Revised: 16 March 2022 / Accepted: 29 March 2022 / Published: 12 April 2022
(This article belongs to the Special Issue Feature Papers in Compounds)
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Abstract

:
HS-SPME-GC–MS analysis of the scent of Dactylorhiza viridis revealed the presence of verbenone (28.86%), caryophyllene (25.67%), β-terpineol (9.48%), and δ-cadinene (6.94%). In the scent of Dactylorhiza romana β-ocimene (18.69%), pentadecane (18.40%), α-farnesene (14.65%), and isopropyl 14-methylpentadecanoate (14.32%) were found. Dactylorhiza incarnata contained tetradecane (11.07%), pentadecane (28.40%), hexadecane (19.53%), heptadecane (17.33%), and α-cubenene (11.48%). Analysis of Dactylorhiza saccifera showed the presence of caryophyllene (17.38%), pentadecane (6.43%), hexadecane (6.13%), and heptadecane (5.08%). Finally, the aroma components found in Dactylorhiza sambucina were caryophyllene (12.90%), β-sesquiphellandrene (32.16%), 4,5-di-epi-aristolochene (10.18%).

1. Introduction

The taxonomy of the genus Dactylorhiza Necker ex Nevski is one of the most studied in the Orchidaceae family [1,2,3,4,5,6,7,8], widespread in Eurasia, North Africa, Alaska [9,10], with a great variety of confused and difficult to classify forms in precise taxa. It includes a number of species that varies strongly between authors, from twelve [1] to seventy-five species [6], or to thirty-six species and forty-six subspecies [11]. Traditional classifications recognize four sections of the genus Dactylorhiza: Aristatae, Sambucinae, Iberanthus, and Dactylorhiza s.s. [6]. In the early 2000s, new genetic work led to the inclusion of Coeloglossum viride, the only species of the genus Coeloglossum Hartm. 1820, in the genus Dactylorhiza as Dactylorhiza viridis (L.) [12,13]. Several authors have used this new classification in recently published monographs [14,15,16], while others [17,18,19] have been reluctant to include Coeloglossum viride within Dactylorhiza, arguing that current evidence is insufficient.
In this work it was decided to consider Coeloglossum in Dactylorhiza recognizing D. viride, as reported in recent molecular biology [20,21,22,23,24,25] and molecular genetics studies [10,26,27,28,29,30]. The scents emitted by five species of Dactylorhiza present in Southern Italy, four present in Basilicata, Dactylorhiza viridis (L.) R. M. Bateman, Pridgeon, and M. W. Chase (Figure 1a), Dactylorhiza romana (Sebastiani) Soó (Figure 1b), Dactylorhiza sambucina (L.) Soó (Figure 2a), and one present in Campania, Dactylorhiza saccifera (Brongn.) Soó (Figure 2b), and Dactylorhiza incarnata (L.) Soó (Figure 2c) were analyzed.
D. viridis is an uncommon species in Basilicata; it always grows in small populations (from 1 to 10 plants) in open woods and pastures from 600 m a.s.l. at 2100 m a.s.l. It has a very variable morphology, due to its stature (plants more than 30 cm high in the open woods and meadows of the mid-hill, or a few centimeters low in altitude meadows), due to its color (from light green to reddish yellow), and the number of flowers. D. viridis is the only species of the group that has a rewarding strategy by rewarding pollinators with nectar, even if in minimal quantities [27], while, on the contrary, the other species of Dactylorhiza do not produce nectar by pursuing a strategy of food deception. Food-deceptive orchids are more common than sexually deceptive ones; their flowers provide signals of food gratification but do not provide re-compensation [31,32,33]. In Basilicata the populations of D. romana and D. sambucina are characterized by the simultaneous presence of flowers colored from yellow to red with more or less frequent various intermediate forms, while the populations of D. saccifera, and D. incarnata, have flowers with pinkish, white, or fleshy pinks often faded and attenuated in their features.
The color, smell, size, and shape of flowers are key signals that attract pollinators in search of rewards [34,35,36]. Floral color is often included in studies on the evolutionary models of pollination systems while floral scents, whose characterization requires sophisticated and complex tools, have been little studied, even if they are often considered the main attraction for pollinators [37,38,39,40]. Different types of floral scent variations can be distinguished. The floral odor can vary in composition (when the flowers emit different compounds or distinct ratios of the same compounds) and/or emission speed (that is, when the flowers emit the same bouquet but in different quantities). In many cases, it has been reported that the chemical profiles of floral scents vary both between individuals of the same population and between different populations, through an almost infinite number of combinations of volatile compounds [41,42,43,44,45,46,47].
Comparative analysis of the emission of scents revealed a greater variation of the compounds among the same individuals in the deceptive orchids compared to the gratifying orchids [48,49]. The flower bouquet varies significantly between food deceptive orchids, even within the same genus, and can affect pollinator species and their behaviors in multiple ways [31,41]. The analysis of floral odors in orchids has been mainly carried out to characterize olfactory signals presumably attractive to pollinators, but only in a few cases have these studies been coupled, with the analysis of the pollinator response, to the volatile compounds emitted using electrophysiological techniques [48,50,51] and behavioral tests [52,53,54,55]. Therefore, there is an increasing need for a better understanding of the evolution of floral scents in order to obtain a more complete view of the mechanisms and patterns of evolution of pollination systems.
Food-deceptive orchids are pollinated by generalist pollinators [56], mainly bumblebee queens and various other bees [57,58,59,60], just emerged from the soil, without experience which, after the first attempts at pollination, abandon the plant, moving away in search of other inflorescences [61]. It is thought that the wide variability of the morphology of flowers and scents in deceptive species for food favors cross-pollination by reducing the learning in the recognition of flowers by newly emerged, inexperienced pollinators, thus limiting self-pollination and geitonogamy and favoring outbreeding.
While D. romana, sambucina, and saccifera are widespread in the territory of Basilicata, also forming large populations, D. incarnata has been identified in a single station on the Maddalena Mountains (Padula. Salerno) on the border between Basilicata and Campania where it forms a large population mixed with D. saccifera and where it is possible to find many hybrid forms between the two species and also many plants of D. incarnata var. ochroleuca. This population of D. incarnata is the southernmost station reported in Italy.
The purpose of this work is to complete the collection of data on the various perfumes emitted by the species of orchids in Basilicata by using the same technique, solid phase microextraction performed on intact plats followed by gas chromatography–mass spectrometry. Until now, the volatile organic compounds constituents of the scent of the orchid species have been determined on several orchid species [62,63,64,65,66,67,68,69].

2. Materials and Methods

2.1. Plant Material

The sample of D. viridis was collected at Moliterno (Pz), 1100 m a.s.l., on 23 May 2018. The sample of D. romana was collected at Rifreddo (Pz), 1120 m a.s.l., on 10 April 2017. The sample of D. sambucina (yellow color) was collected at Moliterno (Pz), 1200 m a.s.l., on 21 May 2018. The sample of D. saccifera was collected at Abriola (Pz), 1200 m a.s.l., on 30 June 2017. The sample of D. incarnata was collected at Mandranello, Padula (Sa), 1200 m a.s.l., on 3 June 2018. The plants were collected by Vito Antonio Romano.
The plants were harvested about two weeks before flowering by taking all the clod of earth, taking care not to damage the root system, planted in special pots in the gardens of the University of Basilicata (Potenza 650 m a.s.l.), in waiting for their full bloom. Two days before the tests the plants were transferred to an air-conditioned room at 22 °C. The plants were tested whole without being damaged under a cylindrical glass bell (12 cm × 45 cm) in which only the inflorescence and the SPME probe were inserted.
To avoid contamination, the interior of the bell was isolated from the external environment with appropriate closing and sealing systems during the 24 h of the test (from 8 in the morning to 8 the following day).
In order to be sure that the internal environment of the bell was isolated from the external environment, various blank tests were carried out.
The plants were successively used for further studies on pollination, fertility, and germination of the plants. After these studies the plants were not in condition to be collected in an herbarium. However, these species can be recognized without ambiguities on the basis of their properties, well documented by the Figure 1 and Figure 2. In view of the fact that the investigated taxa are rare wild plants, in order to preserve the species, we have chosen to use a single plant for our analysis.

2.2. Analysis of Volatile Organic Compounds

The SPME analysis of five different samples of Dactylorhiza has been performed. This way, the identified plants were collected and inserted in glass jars for 24 h where the fiber (DVB/CAR/PDMS) and SPME syringe were also placed. After this time the fiber was desorbed in a gas chromatographic apparatus equipped with a quadrupole mass spectrometer detector. A 50/30-μm DVB/CAR/PDMS module with 1 cm fiber (57328-U, Supelco, Milan, Italy) was employed to determine VOCs. SPME fiber was maintained in the bell jar for 24 h. The analytes were desorbed in the splitless injector at 250 °C for 2 min. Analyses were accomplished with an HP 6890 Plus gas chromatograph equipped with a Phenomenex Zebron ZB-5 MS capillary column (30-m × 0.25-mm i.d. × 0.25 μm FT) (Agilent, Milan, Italy). An HP 5973 mass selective detector (Agilent, Milan, Italy) in the range 0–800 m/z (Agilent) was utilized with helium at 0.8 mL/min as the carrier gas. The EI source was used at 70 eV. The analyses were performed by using a splitless injector. The splitless injector was maintained at 250 °C and the detector at 230 °C. The oven was held at 40 °C for 2 min, then gradually warmed, 8 °C/min, up to 250 °C and held for 10 min. Tentative identification of aroma components was based on mass spectra and Wiley 11 and NIST 14 library comparison. Single VOC peak was considered as identified when its experimental spectrum matched with a score over 90% that present in the library. All the analyses were performed in triplicate.

3. Results and Discussion

The scent of Dactylorhiza orchids has been the object of some studies in the past. Analysis of D. sambucina showed the presence of limonene, β-myrcene, α-pinene, α-bergamotene, β-bisabolene, caryophyllene, and β-selinene [70]. Dichloromethane extracts of flowers of D. incarnata showed the presence of 4-hydroxybenzaldehyde (16.88%), 4-hydrozybenzyl alcohol (30.60%), and methyl 4-hydroxyphenylacetate (34.37%) [71]. Pentane, diethyl ether extraction of flowers of D. incarnata showed the presence of nonanal, 9-(Z)-heptacosene, 9-(Z)-nonacosene, tricosane, pentacosane, and heptacosane [72] The analysis of the scent of D. romana (red flower), obtained by head space analysis of the scent absorbed on Porapak Q, showed the presence of several components, including nonanal (9.19%), sabinene (10.89%), (E)-ocimene (15.63%), and linalool (7.99%) [31]. Such different results, obtained by using different analytical techniques, allowed us to analyze the scent of these species by using SPME (solid phase microextraction) technique. The results are reported in Table 1.
The never studied before D. viridis contains, as its main components, verbenone (28.86%) and caryophyllene (25.67%), while other compounds present in relevant amounts are β-terpineol (9.48%) and δ-cadinene (6.94%) (Table 1 and Figure 3).
In the scent of D. romana several compounds were found: β-ocimene (18.69%, found also in [31]), pentadecane (18.40%), α-farnesene (14.65%), and isopropyl 14-methylpentadecanoate (14.32%) (Table 1). Previous works published on the aroma of D. incarnata found phenolic compounds, in one case, while long chain alkanes and alkenes, were found in another case [71,72]. SPME analysis of the scent detected the presence of a mixture of hydrocarbons, but with lower molecular weight than those found in [72]. Tetradecane (11.07%), pentadecane (28.40%), hexadecane (19.53%), and heptadecane (17.33%) were the main components, together with α-cubenene (11.48%) (Table 1).
D. saccifera contained, as a main component, caryophyllene (17.38%), while other significant compounds were hydrocarbons, pentadecane (6.43%), hexadecane (6.13%), and heptadecane (5.08%) (Table 1). Finally, the aroma components found in D. sambucina were caryophyllene (12.90%, found also in [70]), β-sesquiphellandrene (32.16%, Figure 4), 4,5-di-epi-aristolochene (10.18%, Figure 4) (Table 1).

4. Conclusions

The results described above can give us some useful information. First, the results of our analysis, performed by using SPME technique, are not in agreement with previous described scent composition [31,70,71,72]. This difference may depend on several factors: first of all, the different location of the plants under study. The different environmental conditions could induce plants to adopt different strategies for pollination. Second, the different analysis methodology could play a significant role. Furthermore, we can observe that every species adopts a different strategy. D. viridis has a scent where terpenes are the main components. This statement is applicable also to D. romana; however, it is noteworthy that the terpenes involved in the scent are different from those observed in the other species. The scent of D. incarnata only included hydrocarbons as components; hydrocarbons are present in the scent of D. saccifera but, in this case, caryophyllene is also present in relevant amount. Finally, terpenes were detected in the scent of D. sambucina, as in D. viridis and in D. romana, but the compounds involved in the scent, with the exception of caryophyllene, are different from those observed in the other species.

Author Contributions

Conceptualization, M.D. and V.A.R.; methodology, R.R.; investigation, R.R., L.V. and M.M.; data curation, R.L.; writing—original draft preparation, V.A.R. and M.D.; writing—review and editing, M.D., V.A.R. and R.L. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Klinge, J. Dactylorchids, orchids subgeneris, monographiae prodromus. Acta Horti Petropol. 1898, 17, 145–201. [Google Scholar]
  2. Vermeulen, P. Studies on Dactylorchids; Schotanus & Jens: Utrecht, The Netherlands, 1947. [Google Scholar]
  3. Soó, R. Synopsis generis Dactylorhiza (Dactylorchis). Ann. Univ. Sci. Bp. Biol. 1960, 3, 335–357. [Google Scholar]
  4. Senghas, K. Taxonomische Übersicht der Gattung Dactylorhiza Necker ex Nevski. Jahresber. Naturwiss. Ver. Wupp. 1968, 21–22, 32–67. [Google Scholar]
  5. Nelson, E. Monographie und Ikonographie der Orchidaceen-Gattung Dactylorhiza; Speich: Zürich, Switzerland, 1976. [Google Scholar]
  6. Averyanov, L.V. A review of the genus Dactylorhiza. In Orchid Biology. Reviews and Perspectives; Arditti, J., Ed.; Timber Press: Portland, OR, USA, 1990; pp. 159–206. [Google Scholar]
  7. Pedersen, H.Æ. Species concept and guidelines for infraspecific taxonomic ranking in Dactylorhiza (Orchidaceae). Nord. J. Bot. 1998, 18, 289–311. [Google Scholar] [CrossRef]
  8. Hedrén, M. Systematics of the Dactylorhiza euxina/incarnata/maculata polyploid complex (Orchidaceae) in Turkey: Evidence from allozyme data. Plant Syst. Evol. 2001, 229, 23–44. [Google Scholar] [CrossRef]
  9. Delforge, P. Guide des Orchidees d’Europe, d’Afrique du Nord et du Proche-Orient, 2nd ed.; Delachaux et Niestle: Lausanne, Switzerland, 2001. [Google Scholar]
  10. Efimov, P.G.; Philippov, E.G.; Krivenko, D.A. Allopolyploid speciation in Siberian Dactylorhiza (Orchidaceae, Orchidoideae). Phytotaxa 2016, 258, 101–120. [Google Scholar] [CrossRef]
  11. Eccarius, W. Die Orchideengattung Dactylorhiza; Eisenach: Bürgel, Germany, 2016. [Google Scholar]
  12. Bateman, R.M.; Pridgeon, A.M.; Chase, M.W. Phylogenetics of subtribe Orchidinae (Orchidoideae, Orchidaceae) based on nuclear ITS sequences. 2. Infrageneric relationships and taxonomic revision to achieve monophyly of Orchis sensu stricto. Lindleyana 1997, 12, 113–141. [Google Scholar]
  13. Cribb, P.J.; Chase, M.W. Proposal to conserve the name Dactylorhiza Necker ex Nevski over Coeloglossum Hartm. (Orchidaceae). Taxon 2001, 50, 581–582. [Google Scholar] [CrossRef]
  14. Dusak, F.; Pernot, P. Les Orchidées Sauvages d’Île-de-France; Biotope: Mèze, Germany, 2002. [Google Scholar]
  15. Jacquet, P.; Scappaticci, G. Une Répartition des Orchidées Sauvages de France, 3rd ed.; Société Francaise d’Orchidophilie: Paris, France, 2003. [Google Scholar]
  16. Foley, M.; Clarke, S. Orchids of the British Isles; Griffin Press: Cheltenham, UK, 2005. [Google Scholar]
  17. Rossi, W.; Eldredge Maury, A. Iconography of Italian Orchids; Istituto Nazionale per la Fauna Selvatica ‘Alessandro Ghigi’: Bologna, Italy, 2002. [Google Scholar]
  18. Delforge, P. Guide des Orchidées d’Europe, d’Afrique du Nordiska et du Proche-Orient, 3rd ed.; Delachaux et Niestlé: Lausanne, Switzerland, 2005. [Google Scholar]
  19. Baumann, H.; Blatt, H.; Dierssen, K.; Dietrich, H.; Dostmann, H.; Eccarius, W.; Kretzschmar, H.; Kühn, H.-D.; Möller, O.; Paulus, H.F.; et al. Die Orchideen Deutschlands; Arbeitskreise Heimische Orchideen: Uhlstädt-Kirchhasel, Germany, 2005. [Google Scholar]
  20. Bateman, R.M.; Hollingsworth, P.M.; Preston, J.; Yi-Bo, L.; Pridgeon, A.M.; Chase, M.W. Molecular phylogenetics and evolution of Orchidinae and selected Habenariinae (Orchidaceae). Bot. J. Linn. Soc. 2003, 142, 1–40. [Google Scholar] [CrossRef] [Green Version]
  21. Shipunov, A.B.; Fay, M.F.; Pillon, Y.; Bateman, R.M.; Chase, M.W. Dactylorhiza (Orchidaceae) in European Russia: Combined molecular and morphological analysis. Am. J. Bot. 2004, 91, 1419–1426. [Google Scholar] [CrossRef]
  22. Devos, N.; Raspé, O.; Oh, S.H.; Tyteca, D.; Jacquemart, A.L. The evolution of Dactylorhiza (Orchidaceae) allotetraploid complex: Insights from nrDNA sequences and cpDNA PCR-RFLP data. Mol. Phylogenet. Evol. 2006, 38, 767–778. [Google Scholar] [CrossRef]
  23. Pillon, Y.; Fay, M.F.; Hedrén, M.; Bateman, R.M.; Devey, D.S.; Shipunov, A.B.; Van Ver Bank, M.; Chase, M.W. Evolution and temporal diversification of western European polyploid species complexes in Dactylorhiza (Orchidaceae). Taxon 2007, 56, 1185–1208. [Google Scholar] [CrossRef] [Green Version]
  24. Inda, L.A.; Pimentel, M.; Chase, M.W. Chalcone synthase variation and phylogenetic relationships in Dactylorhiza (Orchidaceae). Bot. J. Linn. Soc. 2010, 163, 155–165. [Google Scholar] [CrossRef] [Green Version]
  25. Balao, F.; Trucchi, E.; Wolfe, T.M.; Hao, B.-H.; Lorenzo, M.T.; Baar, J.; Sedman, L.; Kosiol, C.; Amman, F.; Chase, M.W.; et al. Adaptive sequence evolution is driven by biotic stress in a pair of orchid species (Dactylorhiza) with distinct ecological optima. Mol. Ecol. 2017, 26, 3649–3662. [Google Scholar] [CrossRef] [Green Version]
  26. Givnish, T.J.; Spalink, D.; Ames, M.; Lyon, S.P.; Hunter, S.J.; Zuluaga, A.; Iles, W.J.D.; Clements, M.A.; Arroyo, M.T.K.; Leebens-Mack, J.; et al. Orchid phylogenomics and multiple drivers of their extraordinary diversification. Proc. R. Soc. B Biol. Sci. 2015, 282, 20151553. [Google Scholar] [CrossRef]
  27. Bateman, R.M.; Rudall, P.J. Clarified relationship between Dactylorhiza viridis and Dactylorhiza iberica renders obsolete the former genus Coeloglossum (Orchidaceae: Orchidinae). Kew Bull. 2018, 73, 4. [Google Scholar] [CrossRef] [Green Version]
  28. Bateman, R.M.; Murphy, A.R.; Hollingsworth, P.M.; Hart, M.L.; Denholm, I.; Rudall, P.J. Molecular and morphological phylogenetics of the digitate-tubered clade within subtribe Orchidinae ss (Orchidaceae: Orchideae). Kew Bull. 2018, 73, 54. [Google Scholar] [CrossRef] [Green Version]
  29. Kaki, A.; Vafaee, Y.; Khadivi, A. Genetic variation of Anacamptis coriophora, Dactylorhiza umbrosa, Himantoglossum affine, Orchis mascula, and Ophrys schulzei in the western parts of Iran. Ind. Crops Prod. 2020, 156, 112854. [Google Scholar] [CrossRef]
  30. Brandrud, M.K.; Baar, J.; Lorenzo, M.T.; Bateman, R.M.; Chase, M.W.; Hedrén, M.; Paun, O. Phylogenomic relationships of diploids and the origins of allotetraploids in Dactylorhiza (Orchidaceae): RADseq data track reticulate evolution. Syst. Biol. 2019, 69, 91–109. [Google Scholar] [CrossRef]
  31. Salzmann, C.C.; Schiestl, F.P. Odour and colour polymorphism in the food deceptive orchid Dactylorhiza romana. Plant Syst. Evol. 2007, 267, 37–45. [Google Scholar] [CrossRef]
  32. Jersáková, J.; Johnson, S.D.; Jürgens, A. Deceptive behaviour in plants. II. Food deception by plants: From generalized systems to specialized floral mimicry. In Plant–Environment Interactions; Baluska, F., Ed.; Springer: Berlin/Heidelberg, Germany, 2009; pp. 223–246. [Google Scholar]
  33. Walsh, R.P.; Michaels, H.J. When it pays to cheat: Examining how generalized food deception increases male and female fitness in a terrestrial orchid. PLoS ONE 2017, 12, e0171286. [Google Scholar] [CrossRef] [Green Version]
  34. Chittka, L.; Raine, N.E. Recognition of flowers by pollinators. Curr. Opin. Plant Biol. 2006, 9, 428–435. [Google Scholar] [CrossRef]
  35. Sun, M.; Schlüter, P.M.; Gross, K.; Schiestl, F.P. Floral isolation is the major reproductive barrier between a pair of rewarding orchid sister species. J. Evol. Biol. 2015, 28, 117–129. [Google Scholar] [CrossRef]
  36. Valenta, K.; Nevo, O.; Martel, C.; Chapman, C.A. Plant attractants: Integrating insights from seed dispersal and pollination ecology. Evol. Ecol. 2017, 31, 249–267. [Google Scholar] [CrossRef]
  37. Dicke, M. Chemical ecology: From genes to communities. In Chemical Ecology: From Genes to Ecosystem; Dicke, M., Taken, W., Eds.; Springer: Dordrecht, The Netherlands, 2006; pp. 175–189. [Google Scholar]
  38. Raguso, R.A. Wake up and smell the roses: The ecology and evolution of floral scent. Ann. Rev. Ecol. Evol. Syst. 2008, 39, 549–569. [Google Scholar] [CrossRef]
  39. Raguso, R.A. Start making scents: The challenge of integrating chemistry into pollination ecology. Entomol. Exp. Appl. 2008, 128, 196–207. [Google Scholar] [CrossRef]
  40. Whitehead, M.R.; Peakall, R. Integrating floral scent, pollination ecology and population genetics. Funct. Ecol. 2009, 23, 863–874. [Google Scholar] [CrossRef]
  41. Raguso, R.A.; Levin, R.A.; Fooze, S.E.; Holmberg, M.W.; McDade, L.A. Fragrance chemistry, nocturnal rhythms and pollination “syndromes” in Nicotiana. Phytochemistry 2003, 63, 265–284. [Google Scholar] [CrossRef]
  42. Hoballah, M.E.; Stuurman, J.; Turlings, T.C.J.; Guerin, P.M.; Connétable, S.; Kuhlemeier, C. The composition and timing of flower odour emission by wild Petunia axillaris coincide with the antennal perception and nocturnal activity of the pollinator Manduca sexta. Planta 2005, 222, 141–150. [Google Scholar] [CrossRef] [Green Version]
  43. Knudsen, J.T.; Eriksson, R.; Gershenzon, J.; Stahl, B. Diversity and distribution of floral scent. Bot. Rev. 2006, 72, 1–120. [Google Scholar] [CrossRef]
  44. Theis, N.; Lerdau, M.; Raguso, R.A. The challenge of attracting pollinators while evading floral herbivores: Patterns of fragrance emission in Cirsium arvense and Cirsium repandum (Asteraceae). Int. J. Plant. Sci. 2007, 168, 587–601. [Google Scholar] [CrossRef] [Green Version]
  45. Dötterl, S.; Jareiß, K.; Salma Jhumur, U.; Jürgens, A. Temporal variation of flower scent in Silene otitis (Caryophyllaceae): A species with a mixed pollination system. Bot. J. Linn. Soc. 2012, 169, 447–460. [Google Scholar] [CrossRef]
  46. Parachnowitsch, A.L.; Raguso, R.A.; Kessler, A. Phenotypic selection to increase floral scent emission, but not flower size or colour in bee-pollinated Penstemon digitalis. New Phytol. 2012, 195, 667–675. [Google Scholar] [CrossRef] [PubMed]
  47. Delle Vedove, R.; Schatz, B.; Dufay, M. Understanding intraspecific variation of floral scent in light of evolutionary ecology. Ann. Bot. 2017, 120, 1–20. [Google Scholar] [CrossRef] [Green Version]
  48. Salzmann, C.C.; Cozzolino, S.; Schiestl, F.P. Floral scent in food deceptive orchids: Species specificity and sources of variability. Plant Biol. 2007, 9, 720–729. [Google Scholar] [CrossRef]
  49. Salzmann, C.C.; Nardella, A.M.; Cozzolino, S.; Schiestl, F.P. Variability in floral scent in rewarding and deceptive orchids: The signature of pollinator-imposed selection? Ann. Bot. 2007, 100, 757–765. [Google Scholar] [CrossRef] [Green Version]
  50. Galizia, C.G.; Kunze, J.; Gumbert, A.; Borg-Karlson, A.K.; Sachse, S.; Markl, C.; Menzel, R. Relationship of visual and olfactory signal parameters in a food-deceptive flower mimicry system. Behav. Ecol. 2005, 16, 159–168. [Google Scholar] [CrossRef]
  51. Stökl, J.; Twele, R.; Erdmann, D.; Francke, W.; Ayasse, M. Comparison of the flower scent of the sexually deceptive orchid Ophrys iricolor and the female sex pheromone of its pollinator Andrena morio. Chemoecology 2007, 17, 231–233. [Google Scholar] [CrossRef]
  52. Dodson, C.H.; Dressler, R.L.; Hills, H.G.; Adams, R.M.; Williams, N.H. Biologically active compounds in orchid fragrances. Science 1969, 164, 1243–1249. [Google Scholar] [CrossRef]
  53. Ayasse, M.; Schiestl, F.P.; Paulus, H.F.; Ibarra, F.; Francke, W. Pollinator attraction in a sexually deceptive orchid by means of unconventional chemicals. Proc. R. Soc. B 2003, 270, 517–522. [Google Scholar] [CrossRef] [Green Version]
  54. Jersáková, J.; Jurgens, A.; Smilauer, P.; Johnson, S.D. The evolution of floral mimicry: Identifying traits that visually attract pollinators. Funct. Ecol. 2012, 26, 1381–1389. [Google Scholar] [CrossRef]
  55. Peter, C.I.; Johnson, S.D. A pollinator shift explains floral divergence in an orchid species complex in South Africa. Ann. Bot. 2014, 113, 277–288. [Google Scholar] [CrossRef]
  56. Dafni, A. Mimicry and deception in pollination. Ann. Rev. Ecol. Syst. 1984, 15, 259–278. [Google Scholar] [CrossRef]
  57. Nilsson, L.A. Anthecology of Orchis morio (Orchidaceae) at its outpost in the north. Nova Acta Regiae Soc. Sci. Ups. 1984, 5, 166–179. [Google Scholar]
  58. Van Der Cingel, N.A. An Atlas of Orchid Pollination: European Orchids; CRC Press: Boca Raton, FL, USA, 2001. [Google Scholar]
  59. Cozzolino, S.; Schiestl, F.; Müller, A.; De Castro, O.; Nardella, A.M.; Widmer, A. Evidence for pollinator sharing in Mediterranean nectar mimic orchids: Absence of premating barriers? Proc. R. Soc. B 2005, 272, 1271–1278. [Google Scholar] [CrossRef] [Green Version]
  60. Schiestl, F.P. On the success of a swindle: Pollination by deception in orchids. Naturwissenschaften 2005, 92, 255–264. [Google Scholar] [CrossRef] [Green Version]
  61. Peter, C. Pollination, Floral Deception and Evolutionary Processes in Eulophia (Orchidaceae) and Its Allies. Ph.D. Thesis, University of KwaZulu-Natal, Durban, South Africa, 2009. [Google Scholar]
  62. D’Auria, M.; Lorenz, R.; Racioppi, R.; Romano, V.A. Fragrance components of Platanthera bifolia subsp. osca. Nat. Prod. Res. 2017, 31, 1612–1619. [Google Scholar] [CrossRef]
  63. D’Auria, M.; Lorenz, R.; Mecca, M.; Racioppi, R.; Romano, V.A.; Viggiani, L. Fragrance components of Platanthera bifolia subsp. osca and Platanthera chlorantha collected in several sites in Italy. Nat. Prod. Res. 2020, 34, 2857–3861. [Google Scholar] [CrossRef]
  64. D’Auria, M.; Fascetti, S.; Racioppi, R.; Romano, V.A.; Rosati, L. Orchids from Basilicata: The Scent. In Orchids Phytochemistry, Biology and Horticulture; Merillon, J.-M., Kodja, H., Eds.; Springer: Berlin/Heidelberg, Germany, 2022; pp. 627–648. [Google Scholar]
  65. D’Auria, M.; Lorenz, R.; Mecca, M.; Racioppi, R.; Romano, V.A. Aroma components of Cephalanthera orchids. Nat. Prod. Res. 2021, 35, 174–177. [Google Scholar] [CrossRef]
  66. Mecca, M.; Racioppi, R.; Romano, V.A.; Viggiani, L.; Lorenz, R.; D’Auria, M. Volatile organic compounds from Orchis species found in Basilicata (Southern Italy). Compounds 2021, 1, 83–93. [Google Scholar] [CrossRef]
  67. D’Auria, M.; Lorenz, R.; Mecca, M.; Racioppi, R.; Romano, V.A. The composition of the aroma of Serapias orchids in Basilicata (Southern Italy). Nat. Prod. Res. 2021, 35, 4068–4072. [Google Scholar] [CrossRef]
  68. Mecca, M.; Racioppi, R.; Romano, V.A.; Viggiani, L.; Lorenz, R.; D’Auria, M. The scent of Himantoglossum species found in Basilicata (Southern Italy). Compounds 2021, 1, 164–173. [Google Scholar] [CrossRef]
  69. Romano, V.A.; Rosati, L.; Fascetti, S.; Cittadini, A.M.R.; Racioppi, R.; Lorenz, R.; D’Auria, M. Spatial and temporal Variability of the floral scent emitted by Barlia robertiana (Loisel.) Greuter, a Mediterranean food-deceptive orchid. Compounds 2022, 2, 37–53. [Google Scholar] [CrossRef]
  70. Nilsson, L.A. The pollination ecology of Dactylorhiza sambucina (Orchidaceae). Bot. Not. 1980, 133, 367–385. [Google Scholar]
  71. Naczk, A.M.; Kowalkowska, A.K.; Wisniewska, N.; Halinski, D.P.; Kapusta, M.; Czerwicka, M. Floral anatomy, ultrastructure and chemical analysis in Dactylorhiza incarnata/maculate complex (Orchidaceae). Bot. J. Linn. Soc. 2018, 187, 512–536. [Google Scholar] [CrossRef]
  72. Wróblewska, A.; Szczepaniak, L.; Bajguz, A.; Jedrzejczyk, I.; Talalaj, I.; Ostrowiecka, B.; Brzosko, E.; Jermakowicz, E.; Mirski, P. Deceptice strategy in Dactylorhiza orchids: Multidirectional evolution of floral chemistry. Ann. Bot. 2019, 123, 1005–1016. [Google Scholar] [CrossRef]
Compounds 02 00009 g001 550
Figure 1. (a): Dactylorhiza viridis, Moliterno (Pz), 23 May 2018; (b): Dactylorhiza romana, Rifreddo (Pz), 10 April 2017. Photos of V. A. Romano.
Figure 1. (a): Dactylorhiza viridis, Moliterno (Pz), 23 May 2018; (b): Dactylorhiza romana, Rifreddo (Pz), 10 April 2017. Photos of V. A. Romano.
Compounds 02 00009 g001
Compounds 02 00009 g002 550
Figure 2. (a): Dactylorhiza sambucina, Moliterno (Pz), 21 May 2018; (b): Dactylorhiza saccifera Abriola (Pz), 30 June 2017; (c): Dactylorhiza incarnata, Mandranello, Padula (Sa), 6 June 2018. Photos of V. A. Romano.
Figure 2. (a): Dactylorhiza sambucina, Moliterno (Pz), 21 May 2018; (b): Dactylorhiza saccifera Abriola (Pz), 30 June 2017; (c): Dactylorhiza incarnata, Mandranello, Padula (Sa), 6 June 2018. Photos of V. A. Romano.
Compounds 02 00009 g002
Compounds 02 00009 g003 550
Figure 3. Main components of the scent of D. viridis.
Figure 3. Main components of the scent of D. viridis.
Compounds 02 00009 g003
Compounds 02 00009 g004 550
Figure 4. Main components of the scent of D. sambucina.
Figure 4. Main components of the scent of D. sambucina.
Compounds 02 00009 g004
Table
Table 1. SPME-GC–MS analysis of Dactylorhiza species.
Table 1. SPME-GC–MS analysis of Dactylorhiza species.
Compoundr.t. (a) (min.)KI (b)D. viridisD. romanaD. incarnataD. sacciferaD. sambucina
Area % ± 0.03
Mesityl oxide4.94782 2.03
α-Pinene7.78933 0.200.30
Sabinene8.779722.27 2.44
β-Pinene8.86979 0.79
β-Myrcene9.129892.42
2,2,4,6,6-pentamethyl-3-heptene9.291018 0.60
Limonene9.791028 1.88
Eucalyptol10.0010322.65
β-Ocimene10.331044 18.69
β-Terpineol10.7410859.48
Linalool11.221100 0.85
Lilac aldehyde A12.091145 0.20
Lilac aldehyde B12.251154 0.90
Dodecane13.081200 0.45
α-Terpineol13.1612092.07
Lilac alcohol A13.521221 2.08
Verbenone13.55122328.86
Lilac alcohol B13.841235 4.00
Citral14.5512654.21
Tridecane14.881300 2.880.85
2,4,4,6,6,8,8-Heptamethyl-2-nonene16.021343 1.48
α-Cubebene16.421360 11.48 0.34
Tetradecane16.641400 11.073.902.13
β-Elemene16.691403
Caryophyllene17.22142025.67 17.3812.90
Methyl 2-phenylcyclopropanecarboxylate17.311435 0.90
cis-α-Bergamotene17.381440 7.61
β-Farnesene 17.481458 0.68
Geranylacetone17.611468 6.62
Humulene17.761473 0.42
4,5-Di-epi-aristolochene18.231485 10.18
Pentadecane18.2515002.0918.4028.406.43
β-Selinene18.401511 1.28
α-Farnesene18.451518 14.65 3.30
β-Bisabolene18.501523 2.64
δ-Cadinene18.7815306.94
7-Hexadecenal18.641555 1.00
β-Sesquiphellandrene18.761557 32.16
Elemicin19.071566 3.30
Hexadecane19.711600 19.536.131.06
Methyl dihydrojasmonate20.3216502.55 1.23
Cyclotetradecane20.471673 1.58
Heptadecane21.141700 17.335.080.64
3,5-Di-t-butyl-4-hydroxybenzaldehyde22.131772 4.38
Octadecane22.481800 8.243.400.25
Phytone23.141848 0.58
Nonadecane23.701900 2.93
Isopropyl 14-methylpentadecanoate25.351915 14.32 1.94
7,9-Di-t-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione24.111929 1.88
Eicosane24.932000 1.83
13-epi-Manoyl oxide25.492015 3.42
Docosane27.222200 1.93
Tricosane28.312300 2.28
Bis(1-phenylethyl)phenol30.982426 2.08
(a) R.T. retention time; (b) KI Kovats index.
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Mecca, M.; Racioppi, R.; Romano, V.A.; Viggiani, L.; Lorenz, R.; D’Auria, M. Volatile Organic Compounds in Dactylorhiza Species. Compounds 2022, 2, 121-130. https://doi.org/10.3390/compounds2020009

AMA Style

Mecca M, Racioppi R, Romano VA, Viggiani L, Lorenz R, D’Auria M. Volatile Organic Compounds in Dactylorhiza Species. Compounds. 2022; 2(2):121-130. https://doi.org/10.3390/compounds2020009

Chicago/Turabian Style

Mecca, Marisabel, Rocco Racioppi, Vito Antonio Romano, Licia Viggiani, Richard Lorenz, and Maurizio D’Auria. 2022. "Volatile Organic Compounds in Dactylorhiza Species" Compounds 2, no. 2: 121-130. https://doi.org/10.3390/compounds2020009

APA Style

Mecca, M., Racioppi, R., Romano, V. A., Viggiani, L., Lorenz, R., & D’Auria, M. (2022). Volatile Organic Compounds in Dactylorhiza Species. Compounds, 2(2), 121-130. https://doi.org/10.3390/compounds2020009

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