Published January 31, 2019
| Version v1
Journal article
Restricted
Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves
Description
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
Files
Linked records
Additional details
Identifiers
- LSID
- 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.