Published January 31, 2019 | Version v1
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Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves

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Chechetkin, Ivan R., Blufard, Alexander S., Yarin, Andrey Y., Fedina, Evgenia O., Khairutdinov, Bulat I., Grechkin, Alexander N. (2019): Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves. Phytochemistry 157: 92-102, DOI: 10.1016/j.phytochem.2018.10.030, URL: http://dx.doi.org/10.1016/j.phytochem.2018.10.030

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urn:lsid:plazi.org:pub:FFE9FF961207FFB3D92CFF99FA339E6A

References

  • Andersson, M.X., Hamberg, M., Kourtchenko, O., Brunnstrom, A., McPhail, K.L., Gerwick, W.H., Gobel, C., Feussner, I., Ellerstrom, M., 2006. Oxylipin profiling of the hypersensitive response in Arabidopsis thaliana. Formation of a novel oxo-phytodienoic acid-containing galactolipid, arabidopside E. J. Biol. Chem. 281, 31528-31537.
  • 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 Physiol. 142, 28-39.
  • Caldelari, D., Farmer, E.E., 1998. A rapid assay for the coupled cell free generation of oxylipins. Phytochemistry 47, 599-604.
  • Chechetkin, I.R., Blufard, A., Hamberg, M., Grechkin, A.N., 2008. A lipoxygenase-divinyl ether synthase pathway in flax (Linum usitatissimum L.) leaves. Phytochemistry 69, 2008-2015.
  • Chechetkin, I.R., Blufard, A.S., Khairutdinov, B.I., Mukhitova, F.K., Gorina, S.S., Yarin, A.Y., Antsygina, L.L., Grechkin, A.N., 2013. Isolation and structure elucidation of linolipins C and D, complex oxylipins from flax leaves. Phytochemistry 96, 110-116.
  • Chechetkin, I.R., Mukhitova, F.K., Blufard, A.S., Yarin, A.Y., Antsygina, L.L., Grechkin, A.N., 2009. Unprecedented pathogen-inducible complex oxylipins from flax: linolipins A and B. FEBS J. 276, 4463-4472.
  • Fammartino, A., Cardinale, F., Gobel, C., Mene-Saffrane, L., Fournier, J., Feussner, I., Esquerre-Tugaye, M.-T., 2007. Characterization of a divinyl ether biosynthetic pathway specifically associated with pathogenesis in tobacco. Plant Physiol. 143, 378-388.
  • Fauconnier, M.L., Williams, T.D., Marlier, M., Welti, R., 2003. Potato tuber phospholipids contain colneleic acid in the 2-position. FEBS Lett. 538, 155-158.
  • Galliard, T., Phillips, D.R., 1972. The enzymatic conversion of linoleic acid into 9-(nona- 1',3'-dienoxy)-non-8-enoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers. Biochem. J. 129, 743-753.
  • Gogolev, Y.V., Gorina, S.S., Gogoleva, N.E., Toporkova, Y.Y., Chechetkin, I.R., Grechkin, A.N., 2012. Green leaf divinyl ether synthase: gene detection, molecular cloning and identification of a unique CYP74B subfamily member. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1821, 287-294.
  • Gorina, S.S., Toporkova, Y.Y., Mukhtarova, L.S., Chechetkin, I.R., Khairutdinov, B.I., Gogolev, Y.V., Grechkin, A.N., 2014. Detection and molecular cloning of CYP74Q1 gene: identification of Ranunculus acris leaf divinyl ether synthase. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1841, 1227-1233.
  • Grechkin, A.N., 2002. Hydroperoxide lyase and divinyl ether synthase. Prostag. Other Lipid Mediat. 68-69, 457-470.
  • Grechkin, A.N., Fazliev, F.N., Mukhtarova, L.S., 1995. The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins. FEBS Lett. 371, 159-162.
  • Grechkin, A.N., Ilyasov, A.V., Hamberg, M., 1997. On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs. Eur. J. Biochem. 245, 137-142.
  • Gullner, G., Kunstler, A., Kiraly, L., Pogany, M., Tobias, I., 2010. Up-regulated expression of lipoxygenase and divinyl ether synthase genes in pepper leaves inoculated with Tobamoviruses. Physiol. Mol. Plant Pathol. 74, 387-393.
  • Hamberg, M., 1998. A pathway for biosynthesis of divinyl ether fatty acids in green leaves. Lipids 33, 1061-1071.
  • Hamberg, M., 2002. Biosynthesis of new divinyl ether oxylipins in Ranunculus plants. Lipids 37, 427-433.
  • Hamberg, M., 2004. Isolation and structures of two divinyl ether fatty acids from Clematis vitalba. Lipids 39, 565-569.
  • Hamberg, M., Liepinsh, E., Otting, G., Griffiths, W., 1998. Isolation and structure of a new galactolipid from oat seeds. Lipids 33, 355-363.
  • Hartley, S.E., Eschen, R., Horwood, J.M., Gange, A.C., Hill, E.M., 2015. Infection by a foliar endophyte elicits novel arabidopside-based plant defence reactions in its host, Cirsium arvense. New Phytol. 205, 816-827.
  • Hisamatsu, Y., Goto, N., Hasegawa, K., Shigemori, H., 2003. Arabidopsides A and B, two new oxylipins from Arabidopsis thaliana. Tetrahedron Lett. 44, 5553-5556.
  • Hisamatsu, Y., Goto, N., Sekiguchi, M., Hasegawa, K., Shigemori, H., 2005. Oxylipins arabidopsides C and D from Arabidopsis thaliana. J. Nat. Prod. 68, 600-603.
  • Hughes, R.K., De Domenico, S., Santino, A., 2009. Plant cytochrome CYP74 family: biochemical features, endocellular localisation, activation mechanism in plant defence and improvements for industrial applications. Chembiochem 10, 1122-1133.
  • Jiang, Z.D., Gerwick, W.H., 1990. Galactolipids from the temperate red marine alga Gracilariopsis lemaneiformis. Phytochemistry 29, 1433-1440.
  • Jiang, Z.D., Gerwick, W.H., 1991. An aldehyde-containing galactolipid from the red alga Gracilariopsis lemaneiformis. Lipids 11, 960-963.
  • Jiang, Z.D., Gerwick, W.H., 1997. Novel oxylipins from the temperate red alga Polyneura latissima: evidence for an arachidonate 9(S)-lipoxygenase. Lipids 32, 231-235.
  • Kourtchenko, O., Andersson, M.X., Hamberg, M., Brunnstrom, A., Gobel, C., McPhail, K.L., Gerwick, W.H., Feussner, I., Ellerstrom, M., 2007. Oxo-phytodienoic acid-containing galactolipids in Arabidopsis: jasmonate signaling dependence. Plant Physiol. 145, 1658-1669.
  • Moreau, R.A., Doehlert, D.C., Welti, R., Isaac, G., Roth, M., Tamura, P., Nunez, A., 2008. The identification of mono-, di-, tri-, and tetragalactosyl-diacylglycerols and their natural estolides in oat kernels. Lipids 43, 533-548.
  • Mosblech, A., Feussner, I., Heilmann, I., 2010. Oxylipin signaling and plant growth. In: Munnik, T. (Ed.), Plant Lipid Signaling, Plant Cell Monographs. Springer Academic Publishers, Berlin/Heidelberg, pp. 277-291.
  • Nakajyo, H., Hisamatsu, Y., Sekiguchi, M., Goto, N., Hasegawa, K., Shigemori, H., 2006. Arabidopside F, a new oxylipin from Arabidopsis thaliana. Heterocycles 69, 295-301.
  • Nakashima, A., Iijima, Y., Aoki, K., Shibata, D., Sugimoto, K., Takabayashi, J., Matsui, K., 2011. Monogalactosyl diacylglycerol is a substrate for lipoxygenase: its implications for oxylipin formation directly from lipids. J. Plant Interact. 6, 93-97.
  • Nakashima, A., von Reuss, S.H., Tasaka, H., Nomura, M., Mochizuki, S., Iijima, Y., Aoki, K., Shibata, D., Boland, W., Takabayashi, J., Matsui, K., 2013. Traumatin- and dinortraumatin-containing galactolipids in Arabidopsis. J. Biol. Chem. 288, 26078-26088.
  • Nilsson, A.K., Fahlberg, P., Ellerstrom, M., Andersson, M.X., 2012. Oxo-phytodienoic acid (OPDA) is formed on fatty acids esterified to galactolipids after tissue disruption in Arabidopsis thaliana. FEBS Lett. 586, 2483-2487.
  • Nilsson, A.K., Fahlberg, P., Johansson, O.N., Hamberg, M., Andersson, M.X., Ellerstrom, M., 2016. The activity of hydroperoxide lyase 1 regulates accumulation of galactolipids containing 12-oxo-phytodienoic acid in Arabidopsis. J. Exp. Bot. 67, 5133-5144.
  • Nilsson, A.K., Johansson, O.N., Fahlberg, P., Kommuri, M., Topel, M., Bodin, L.J., Sikora, P., Modarres, M., Ekengren, S., Nguyen, C.T., Farmer, E.E., Olsson, O., Ellerstrom, M., Andersson, M.X., 2015. Acylated monogalactosyl diacylglycerol: prevalence in the plant kingdom and identification of an enzyme catalyzing galactolipid head group acylation in Arabidopsis thaliana. Plant J. 84, 1152-1166.
  • Ogorodnikova, A.V., Latypova, L.R., Mukhitova, F.K., Mukhtarova, L.S., Grechkin, A.N., 2008. Detection of divinyl ether synthase in Lily-of-the-Valley (Convallaria majalis) roots. Phytochemistry 69, 2793-2798.
  • Ogorodnikova, A.V., Mukhitova, F.K., Grechkin, A.N., 2013. Screening of divinyl ether synthase activity in nonphotosynthetic tissue of Asparagales. Docl. Biochem. Biophys. 449, 116-118.
  • Ogorodnikova, A.V., Mukhitova, F.K., Grechkin, A.N., 2015. Oxylipins in the spikemoss Selaginella martensii: detection of divinyl ethers, 12-oxophytodienoic acid and related cyclopentenones. Phytochemistry 118, 42-50.
  • Ohashi, T., Ito, Y., Okada, M., Sakagami, Y., 2005. Isolation and stomatal opening activity of two oxylipins from Ipomoea tricolor. Bioorg. Med. Chem. Lett 15, 263-265.
  • Pedras, M.S.C., To, Q.H., 2017. Defence and signaling metabolites of the crucifer Erucastrum canariense: synchronized abiotic induction of phytoalexins and galactooxylipins. Phytochemistry 139, 18-24.
  • Proteau, P.J., Gerwick, W.H., 1993. Divinyl ethers and hydroxy fatty acids from three species of Laminaria (brown algae). Lipids 28, 783-787.
  • Savchenko, T.V., Zastrijnaja, O.M., Klimov, V.V., 2014. Oxylipins and plant abiotic stress resistance. Biochemistry (Moscow) 79, 362-375.
  • Stelmach, B.A., Muller, 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. J. Biol. Chem. 276, 12832-12838.