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User:Daniel Mietchen/Talks/MPI-ICE 2012/Workshop/Cyclo-Oxylipin-galactolipids

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Cyclo-Oxylipin-galactolipids are galactolipids containing cyclic oxylipins. They are also often referred as arabidopsides. Mainly they consist out of one or more of the oxylipins 12-oxophytodienoic acid (OPDA) and/or its C16 analog dinor-oxophytodienoic acid (dnOPDA) esterified to monogalactosyl diacylglycerol (MGDG) or digalactosyl diacylglycerol (DGDG). They were found to make up for a major portion of the total OPDA/dnOPDA content. Until now different structures with OPDA/dnOPDA bound to the SN1 and/or SN2 position, as well as to the 6’position of the galactose were found. [1][2][3][4][5][6][7]


Types

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MGDG-O[5], arabidopside A[3], arabidopside B[3], arabidopside C[4], arabidopside D[4], arabidopside E[1], arabidopside F[7], arabidopside G[6]

Similar substances with a substitution of the galactosyl glycerol by a phosphoglycerol are also found[2].

Appearance

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Up to now they were only found in the aerial part of plants from the genus Arabidopsis. They seem to be mainly, if not totally located to the thylakoid membranes of the chloroplasts.[8]

Function

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It is still not clear what their main function is. Nevertheless a few processes were found were they seem to be involved. Since OPDA/dnOPDA can be metabolized to jasmonic acid (JA). OPDA/dnOPDA containing galactolipids are assumed to contribute in JA formation. Additionally they were found to accumulate after different stresses like wounding[2][5] and perception of the bacterial avirulence proteins[1]. Additionally they were found to have growth inhibiting effects on Botrytis cinerea[6] and OPDA can be released out of them by treatment with insect and fungal lipases[5][9]. This indicates a role in plant defense against bacterial and fungal pathogens and herbivores. Other properties are senescence-promoting effects[10], growth inhibition of cress roots[4] and they seem to be associated to the photosystems[8].

References

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  1. ^ a b c Andersson, M. X.; Hamberg, M.; Kourtchenko, O.; Brunnström, A.; McPhail, K. L.; Gerwick, W. H.; Göbel, C.; Feussner, I.; Ellerström, M. (2006). "Oxylipin Profiling of the Hypersensitive Response in Arabidopsis thaliana: FORMATION OF a NOVEL OXO-PHYTODIENOIC ACID-CONTAINING GALACTOLIPID, ARABIDOPSIDE E". Journal of Biological Chemistry. 281 (42): 31528–31537. doi:10.1074/jbc.M604820200. PMID 16923817.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  2. ^ a b c Buseman, C. M.; Tamura, P.; Sparks, A. A.; Baughman, E. J.; Maatta, S.; Zhao, J.; Roth, M. R.; Esch, S. W.; Shah, J.; Williams, T. D.; Welti, R. (2006). "Wounding Stimulates the Accumulation of Glycerolipids Containing Oxophytodienoic Acid and Dinor-Oxophytodienoic Acid in Arabidopsis Leaves". Plant Physiology. 142 (1): 28–39. doi:10.1104/pp.106.082115. PMC 1557605. PMID 16844834.
  3. ^ a b c Hisamatsu, Y.; Goto, N.; Hasegawa, K.; Shigemori, H. (2003). "Arabidopsides a and B, two new oxylipins from Arabidopsis thaliana". Tetrahedron Letters. 44 (29): 5553. doi:10.1016/S0040-4039(03)01148-1.
  4. ^ a b c d Hisamatsu, Y.; Goto, N.; Sekiguchi, M.; Hasegawa, K.; Shigemori, H. (2005). "Oxylipins Arabidopsides C and D fromArabidopsisthaliana". Journal of Natural Products. 68 (4): 600–603. doi:10.1021/np0495938. PMID 15844959.
  5. ^ a b c d Stelmach, B. A.; Müller, A.; Hennig, P.; Gebhardt, S.; Schubert-Zsilavecz, M.; Weiler, E. W. (2001). "A Novel Class of Oxylipins, sn1-O-(12-Oxophytodienoyl)-sn2-O-(hexadecatrienoyl)-monogalactosyl Diglyceride, from Arabidopsis thaliana". Journal of Biological Chemistry. 276 (16): 12832–12838. doi:10.1074/jbc.M010743200. PMID 11278736.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  6. ^ a b c Kourtchenko, O.; Andersson, M. X.; Hamberg, M.; Brunnström, A.; Göbel, C.; McPhail, K. L.; Gerwick, W. H.; Feussner, I.; Ellerström, M. (2007). "Oxo-Phytodienoic Acid-Containing Galactolipids in Arabidopsis: Jasmonate Signaling Dependence". Plant Physiology. 145 (4): 1658–1669. doi:10.1104/pp.107.104752. PMC 2151682. PMID 17951463.
  7. ^ a b Shigemori, H.; Nakajyo, H.; Hisamatsu, Y.; Sekiguchi, M.; Goto, N.; Hasegawa, K. (2006). "Arabidopside F, a New Oxylipin from Arabidopsis thaliana". Heterocycles. 69: 295. doi:10.3987/COM-06-S(O)33.
  8. ^ a b Böttcher, C.; Weiler, E. W. (2007). "Cyclo-Oxylipin-galactolipids in plants: Occurrence and dynamics". Planta. 226 (3): 629–637. doi:10.1007/s00425-007-0511-5. PMID 17404756.
  9. ^ Schafer, M.; Fischer, C.; Meldau, S.; Seebald, E.; Oelmuller, R.; Baldwin, I. T. (2011). "Lipase Activity in Insect Oral Secretions Mediates Defense Responses in Arabidopsis". Plant Physiology. 156 (3): 1520–1534. doi:10.1104/pp.111.173567. PMC 3135923. PMID 21546453.
  10. ^ Hisamatsu, Y.; Goto, N.; Hasegawa, K.; Shigemori, H. (2006). "Senescence-promoting effect of arabidopside A". Zeitschrift fur Naturforschung. C, Journal of biosciences. 61 (5–6): 363–366. PMID 16869494.
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