Two-dimensional comprehensive gas chromatography (GC×GC) coupled with mass detection was used as a tool for biosynthetic studies of bumblebee pheromones. Prior to biosynthetic experiments, the chromatographic behaviour of isotopically modified esters in the GC×GC system as well as their behaviour in mass detection was studied. The male marking pheromones of Bombus lucorum, Bombus lapidarius and Bombus terrestris were investigated. Main pheromonal components are ethyl tetradec-9-enoate (53 %) and ethyl dodecanoate (6 %) in B. lucorum, hexadec-9-en-1-ol (52 %) and hexadecan-1-ol (31 %) in B. lapidarius, and 2,3-dihydrofarnesol (58 %) and ethyl dodecanoate (15 %) in B. terrestris. The research strategy was based on 1) in vivo incubation of isotopically (2 H, 13 C) modified fatty acids (FAs) and analysis of their metabolites and 2) feeding experiments with 2 H- and 13 C-labelled FAs mixed with food. It was observed that labelled FAs were modified into the most abundant aliphatic compounds present in labial gland secretions. In feeding experiments, the labelled FAs were transformed into pheromone components. Transport of the FA precursors from the fat body through haemolymph was confirmed. The results show that FAs, stored in the form of triacylglycerols in the fat body, are likely to participate in the biosynthesis of some aliphatic pheromone components.

Agricultural Research Zahradní 1 66441 Troubsko

Faculty of Science Charles University Albertov 8 128 40 Prague 2

Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic Flemingovo nám 2 166 10 Prague 6

LECO Corp Applicat Lab Prague Sokolovská 219 190 00 Prague 9

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B. Kullenberg, G. Bergström, B. Bringer, B. Carlberg, B. Cederberg, Zoon 1973, Suppl. 1, 23-29.

H. E. H. Paterson, Evolution and the Recognition Concept of Species, Collected Writings, Johns Hopkins University Press, Baltimore, 1993.

A. Coppée, M. Terzo, I. Valterová, P. Rasmont, Chem. Biodiversity 2008, 5, 2654-2661.

P. Žáček, B. Kalinová, J. Šobotník, O. Hovorka, V. Ptáček, A. Coppée, F. Verheggen, I. Valterová, J. Chem. Ecol. 2009, 35, 698-705.

F. W. L. Sladen, Nature 1912, 88, 586-587.

K. Urbanová, I. Valterová, O. Hovorka, J. Kindl, Eur. J. Entomol. 2001, 98, 111-115.

D. H. Calam, Nature 1969, 221, 856-857.

J. Šobotník, B. Kalinová, L. Cahlíková, F. Weyda, V. Ptáček, I. Valterová, J. Insect Physiol. 2008, 54, 204-214.

B. S. Lanne, G. Bergström, A.-B. Wassgren, B. Törnbäck, Comp. Biochem. Physiol. B 1987, 88, 631-636.

A. Luxová, I. Valterová, K. Stránský, O. Hovorka, A. Svatoš, Chemoecology 2003, 13, 81-87.

P. Matoušková, A. Luxová, J. Matoušková, P. Jiroš, A. Svatoš, I. Valterová, I. Pichová, ChemBioChem 2008, 9, 2534-2541.

A. Buček, H. Vogel, P. Matoušková, D. Prchalová, P. Žáček, V. Vrkoslav, P. Šebesta, A. Svatoš, U. Jahn, I. Valterová, I. Pichová, Insect Biochem. Mol. Biol. 2013, 43, 724-731.

J. Brabcová, D. Prchalová, Z. Demianová, A. Bučánková, H. Vogel, I. Valterová, I. Pichová, M. Zarevúcká, Plos One 2013, 8, e80066.

A. Luxová, PhD thesis, Institute of Chemical Technology, Prague (Czech Republic), 2004.

P. Žáček, D. Prchalová-Horňáková, R. Tykva, J. Kindl, H. Vogel, A. Svatoš, I. Pichová, I. Valterová, ChemBioChem 2013, 14, 361-371.

L. B. Bjostad, W. A. Wolf, W. L. Roelofs in Pheromone Biochemistry (Eds.: G. D. Prestwich, G. J. Blomquist), Academic Press, Orlando, 1987, pp. 77-120.

T. Ando, T. Hase, R. Arima, M. Uchiyama, Agric. Biol. Chem. 1988, 52, 473-478.

E. Plettner, K. N. Slessor, M. L. Winston, Insect Biochem. Mol. Biol. 1998, 28, 31-42.

E. Plettner, K. N. Slessor, M. L. Winston, J. E. Oliver, Science 1996, 271, 1851-1853.

T. Ando, R. Arima, A. Mori, M. Uchiyama, Agric. Biol. Chem. 1986, 50, 1093-1095.

C. Meinert, U. J. Meierhenrich, Angew. Chem. Int. Ed. 2012, 51, 10460-10470;

Angew. Chem. 2012, 124, 10610-10621.

L. S. Bartell, H. K. Higginbotham, J. Chem. Phys. 1965, 42, 851.

W. A. VanHook, Isotope Separation by Gas Chromatography, American Chemical Society, Knoxville, 1969, chap. 7, p. 99.

J. Bermejo, C. G. Blanco, M. D. Guillen, J. Chromatogr. 1986, 351, 425-432.

M. Matucha, W. Jockisch, P. Verner, G. Anders, J. Chromatogr. 1991, 588, 251-258.

H. G. Schmarr, P. Slabizki, S. Muntnich, C. Metzger, E. Gracia-Moreno, J. Chromatogr. A 2012, 1270, 310-317.

S. de Koning, ChemPlusChem 2014, 79, 776-780.

C. J. Venkatramani, J. Z. Xu, J. B. Phillips, Anal. Chem. 1996, 68, 1486-1492.

J. Dallüge, J. Beens, U. A. T. Brinkman, J. Chromatogr. A 2003, 1000, 69-108.

L. M. Blumberg, J. Chromatogr. A 2003, 985, 29-38.

L. M. Blumberg, F. David, M. S. Klee, P. Sandra, J. Chromatogr. A 2008, 1188, 2-16.

M. Matucha, Chromatographia 1989, 27, 552-558.

M. Matucha, E. Smolková, J. Chromatogr. 1976, 127, 163-201.

F. W. McLafferty, F. Tureček, Interpretation of Mass Spectra, 4th ed., Mill Valley, California, 1994, chap. 8-9.

K. Frišonsová, Diploma thesis, Charles University, Prague (Czech Republic), 2009.

P. Jiroš, J. Cvačka, R. Hanus, J. Kindl, E. Kofroňová, I. Valterová, Lipids 2011, 46, 863-871.

P. H. Buist, B. Behrouzian, J. Am. Chem. Soc. 1996, 118, 6295-6296.

E. D. Morgan, Biosynthesis in Insects: Advanced Edition, Royal Soc. Chemistry, Thomsa Graham House, Science Park, Cambridge, 2010, pp. 1-362.

L. B. Bjostad, W. L. Roelofs, Science 1983, 220, 1387-1389.

R. A. Jurenka, K. F. Haynes, R. O. Adlof, M. Bengtsson, W. L. Roelofs, Insect Biochem. Mol. Biol. 1994, 24, 373-381.

M. Schrader, H. D. Fahimi, Histochem. Cell Biol. 2008, 129, 421-440.

H. Osmundsen, C. E. Neat, K. R. Norum, Febs Lett. 1979, 99, 292-296.

H. Osmundsen, C. E. Neat, B. Borrebaek, Int. J. Biochem. 1980, 12, 625-630.

R. Fischer, H. Komnick, Insect Biochem. Mol. Biol. 1992, 22, 793-801.

G. Rosell, S. Hospital, F. Camps, A. Guerrero, Insect Biochem. Mol. Biol. 1992, 22, 679-685.

S. B. Votruba, S. M. Zeddun, D. A. Schoeller, Int. J. Obesity 2001, 25, 1240-1245.

A. Raman, S. Blanc, A. Adams, D. A. Schoeller, J. Lipid Res. 2004, 45, 2339-2344.

L.-K. Law, N. L.-S. Tang, J. Hui, C.-S. Ho, J. Ruiter, T.-F. Fok, R. J. A. Wanders, C. W.-K. Lam, Clin. Chim. Acta 2007, 382, 25-30.

L. Zhang, T. A. Veres-Schalnat, A. Somogyi, J. E. Pemberton, R. M. Maier, Appl. Environ. Microbiol. 2012, 78, 8611-8622.

V. Ptáček, Proc. Apimondia ICPBR, Soesterberg, The Netherlands, 1999, p. 55-57.

V. Ptáček, E. Pernová, R. Borovec, Pszczelnicze Zesz. Nauk. 2000, 44, 305-309.

K. Stránsky, T. Jursík, Fett/Lipid 1996, 98, 65-71.

D. A. Carlson, C. S. Roan, R. A. Yost, J. Hector, Anal. Chem. 1989, 61, 1564-1571.

Expansion of the fatty acyl reductase gene family shaped pheromone communication in Hymenoptera