Survey of volatile oxylipins and their biosynthetic precursors in bryophytes

Phytochemistry

Volumn 71, Issue 5-6, 2010, Pages 574-580

  Croisier, Emmanuel ^b   Rempt, Martin ^a   Pohnert, Georg ^a,b  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b EPFL   (Switzerland)

Author keywords

Dicranum scoparium; Fatty acids; GC MS; Hydroperoxide lyases; Lipoxygenases; Liverworts; Mosses; Oxylipins; Volatiles

Indexed keywords

ESSENTIAL OIL; OXYLIPIN; UNSATURATED FATTY ACID; VEGETABLE PROTEIN; VOLATILE ORGANIC COMPOUND;

ARTICLE; BIOSYNTHESIS; METABOLISM; MOSS; PLANT DISEASE;

BRYOPHYTA; FATTY ACIDS, UNSATURATED; OILS, VOLATILE; OXYLIPINS; PLANT DISEASES; PLANT PROTEINS; VOLATILE ORGANIC COMPOUNDS;

ANTHOCEROTOPHYTA; BRYOPHYTA; BRYOPHYTES; DICRANUM SCOPARIUM; MARCHANTIOPHYTA;

EID: 77949587665     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.12.004     Document Type: Article

References (26)

1. Andreou A., Brodhun F., and Feussner I. Biosynthesis of oxylipins in non-mammals. Prog. Lipid Res. 48 (2009) 148-170
2. Anterola A., Göbel C., Hornung E., Sellhorn G., Feussner I., and Grimes H. Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways. Phytochemistry 70 (2009) 40-52
3. Barofsky A., and Pohnert G. Biosynthesis of polyunsaturated short chain aldehydes in the diatom Thalassiosira rotula. Org. Lett. 9 (2007) 1017-1020
4. Brodhun, F., Schneider, S., Göbel, C., Hornung, E., Feussner, I., 2009. PpoC from Aspergillus nidulans is a fusion protein with one active heme. Biochemical J. doi: 10.1042/BJ20091096.
5. Delker C., Stenzel I., Hause B., Miersch O., Feussner I., and Wasternack C. Jasmonate biosynthesis in Arabidopsis thaliana - enzymes, products, regulation. Plant Biol. 8 (2006) 297-306
6. Dembitsky V.M. Lipids of bryophytes. Prog. Lipid Res. 32 (1993) 281-356
7. Feussner I., and Wasternack C. The lipoxygenase pathway. Ann. Rev. Plant Biol. 53 (2002) 275-297
8. Gardner H.W., Grove M.J., and Salch Y.P. Enzymic pathway to ethyl vinyl ketone and 2-pentenal in soybean preparations. J. Agric. Food Chem. 44 (1996) 882-886
9. Gerwick W.H. Structure and biosynthesis of marine algal oxylipins. Biochim. Biophys. Acta-Lipids Lipid Metab. 1211 (1994) 243-255
10. Ichikawa T., Namikawa M., Yamada K., Sakai K., and Kondo K. Novel cyclopentenonyl fatty acids from mosses, Dicranum scoporium and Dicranum japonicum. Tetrahedron Lett. 24 (1983) 3337-3340
11. Maier I., Pohnert G., Pantke-Böcker S., and Boland W. Solid-phase microextraction and determination of the absolute configuration of the Laminaria digitata (Laminariales, phaeophyceae) spermatozoid-releasing pheromone. Naturwissenschaften 83 (1996) 378-379
12. Matsui K. Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism. Curr. Opin. Plant Biol. 9 (2006) 274-280
13. Noordermeer M.A., Veldink G.A., and Vliegenthart J.F. Fatty acid hydroperoxide lyase: a plant cytochrome P450 enzyme involved in wound healing and pest resistance. ChemBioChem 2 (2001) 494-504
14. Pohnert G. Wound-activated chemical defense in unicellular planktonic algae. Angew. Chem. Int. Ed. 39 (2000) 4352-4354
15. Pohnert G., and Boland W. The oxylipin chemistry of attraction and defense in brown algae and diatoms. Nat. Prod. Rep. 19 (2002) 108-122
16. Qiu Y.L., Li L.B., Wang B., Chen Z.D., Knoop V., Groth-Malonek M., Dombrovska O., Lee J., Kent L., Rest J., Estabrook G.F., Hendry T.A., Taylor D.W., Testa C.M., Ambros M., Crandall-Stotler B., Duff R.J., Stech M., Frey W., Quandt D., and Davis C.C. The deepest divergences in land plants inferred from phylogenomic evidence. Proc. Natl. Acad. Sci. USA 103 (2006) 15511-15516
17. Quatrano R.S., McDaniel S.F., Khandelwal A., Perroud P.F., and Cove D.J. Physcomitrella patens: mosses enter the genomic age. Curr. Opin. Plant Biol. 10 (2007) 182-189
18. Rensing S.A., Lang D., Zimmer A.D., Terry A., Salamov A., Shapiro H., Nishiyama T., Perroud P.F., Lindquist E.A., Kamisugi Y., Tanahashi T., Sakakibara K., Fujita T., Oishi K., Shin-I T., Kuroki Y., Toyoda A., Suzuki Y., Hashimoto S., Yamaguchi K., Sugano S., Kohara Y., Fujiyama A., Anterola A., Aoki S., Ashton N., Barbazuk W.B., Barker E., Bennetzen J.L., Blankenship R., Cho S.H., Dutcher S.K., Estelle M., Fawcett J.A., Gundlach H., Hanada K., Heyl A., Hicks K.A., Hughes J., Lohr M., Mayer K., Melkozernov A., Murata T., Nelson D.R., Pils B., Prigge M., Reiss B., Renner T., Rombauts S., Rushton P.J., Sanderfoot A., Schween G., Shiu S.H., Stueber K., Theodoulou F.L., Tu H., Van de Peer Y., Verrier P.J., Waters E., Wood A., Yang L.X., Cove D., Cuming A.C., Hasebe M., Lucas S., Mishler B.D., Reski R., Grigoriev I.V., Quatrano R.S., and Boore J.L. The Physcomitrella genome reveals evolutionary insights into the conquest of land by plants. Science 319 (2008) 64-69
19. Senger T., Wichard T., Kunze S., Göbel C., Lerchl J., Pohnert G., and Feussner I. A multifunctional lipoxygenase with fatty acid hydroperoxide cleaving activity from the moss Physcomitrella patens. J. Biol. Chem. 280 (2005) 7588-7596
20. Stumpe M., Bode J., Göbel C., Wichard T., Schaaf A., Frank W., Frank M., Reski R., Pohnert G., and Feussner N. Biosynthesis of C9-aldehydes in the moss Physcomitrella patens. Biochim. Biophys. Acta - Mol. Cell Biol. Lipids 1761 (2006) 301-312
21. Toyota M., and Akakawa Y. Volatile constituent of the liverwort Chiloscyphus pallidus. Flavour Frag. J. 9 (1994) 237-240
22. Toyota M., Saito T., Matsunami J., and Asakawa Y. A comparative study on three chemo-types of the liverwort Conocephalum conicum using volatile constituents. Phytochemistry 44 (1997) 1265-1270
23. Wasternack C. Jasmonates: an update on biosynthesis, signal transduction and action in plant stress response, growth and development. Ann. Bot. 100 (2007) 681-697
24. Wichard T., Göbel C., Feussner I., and Pohnert G. Unprecedented lipoxygenase/hydroperoxide lyase pathways in the moss Physcomitrella patens. Angew. Chem. Int. Ed. 44 (2005) 158-161
25. Wichard T., Gerecht A., Boersma M., Poulet S.A., Wiltshire K., and Pohnert G. Lipid and fatty acid composition of diatoms revisited: rapid wound-activated change of food quality parameters influences herbivorous copepod reproductive success. ChemBioChem 8 (2007) 1146-1153
26. Wurzenberger M., and Grosch W. Origin of the oxygen in the products of the enzymatic cleavage reaction of linoleic-acid to 1-octen-3-ol and 10-oxo-trans-8-decenoic acid in mushrooms (Psalliota bispora). Biochim. Biophys. Acta 794 (1984) 18-24