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Oxylipins Arabidopsides C and D from Arabidopsis thaliana

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Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba 305-8572, Japan, Department of Biology, Miyagi University of Education, Sendai 980-0845, Japan, and Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., Tsukuba 305-8585, Japan
Cite this: J. Nat. Prod. 2005, 68, 4, 600–603
Publication Date (Web):March 26, 2005
https://doi.org/10.1021/np0495938
Copyright © 2005 American Chemical Society and American Society of Pharmacognosy
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Abstract

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Two new oxylipins, arabidopsides C (1) and D (2), were isolated from the aerial parts of Arabidopsis thaliana, and the structures of 1 and 2 were elucidated using spectroscopic data, primarily NMR and MS, and chemical means. Arabidopsides C (1) and D (2) are rare digalactosyl diacylglycerides containing 12-oxophytodienoic acid and/or dinor-oxophytodienoic acid. Arabidopside D (2) and arabidopsides A (3) and B (4), which were also isolated from this plant, exhibited inhibitory effects on the growth of the root of cress (Lepidium sativum) seedlings at 5 × 10-5 mol/L.

 University of Tsukuba.

 Miyagi University of Education.

§

 Yamanouchi Pharmaceutical Co., Ltd.

*

 To whom correspondence should be addressed. Tel & Fax:  +81-29-853-4603. E-mail:  [email protected]

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  1. Manon Genva, Mats X. Andersson, Marie-Laure Fauconnier. Simple liquid chromatography-electrospray ionization ion trap mass spectrometry method for the quantification of galacto-oxylipin arabidopsides in plant samples. Scientific Reports 2020, 10 (1) https://doi.org/10.1038/s41598-020-68757-x
  2. Sunitha Shiva, Thilani Samarakoon, Kaleb A. Lowe, Charles Roach, Hieu Sy Vu, Madeline Colter, Hollie Porras, Caroline Hwang, Mary R. Roth, Pamela Tamura, Maoyin Li, Kathrin Schrick, Jyoti Shah, Xuemin Wang, Haiyan Wang, Ruth Welti. Leaf Lipid Alterations in Response to Heat Stress of Arabidopsis thaliana. Plants 2020, 9 (7) , 845. https://doi.org/10.3390/plants9070845
  3. Nita G. Chavez Soria, Mary A. Bisson, G. Ekin Atilla-Gokcumen, Diana S. Aga. High-resolution mass spectrometry-based metabolomics reveal the disruption of jasmonic pathway in Arabidopsis thaliana upon copper oxide nanoparticle exposure. Science of The Total Environment 2019, 693 , 133443. https://doi.org/10.1016/j.scitotenv.2019.07.249
  4. Li Guan, Niels Denkert, Ahmed Eisa, Martin Lehmann, Inga Sjuts, Arne Weiberg, Jürgen Soll, Michael Meinecke, Serena Schwenkert. JASSY, a chloroplast outer membrane protein required for jasmonate biosynthesis. Proceedings of the National Academy of Sciences 2019, 116 (21) , 10568-10575. https://doi.org/10.1073/pnas.1900482116
  5. Manon Genva, Firmin Obounou Akong, Mats X. Andersson, Magali Deleu, Laurence Lins, Marie-Laure Fauconnier. New insights into the biosynthesis of esterified oxylipins and their involvement in plant defense and developmental mechanisms. Phytochemistry Reviews 2019, 18 (1) , 343-358. https://doi.org/10.1007/s11101-018-9595-8
  6. Hideyuki Shigemori. Bioactive Compounds Involved in the Life Cycle of Higher Plants. 2019,,, 385-413. https://doi.org/10.1007/978-3-030-12858-6_2
  7. , , , , , . Progress in the Chemistry of Organic Natural Products 109. 2019,,https://doi.org/10.1007/978-3-030-12858-6
  8. Ivan R. Chechetkin, Alexander S. Blufard, Andrey Y. Yarin, Evgenia O. Fedina, Bulat I. Khairutdinov, Alexander N. Grechkin. Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves. Phytochemistry 2019, 157 , 92-102. https://doi.org/10.1016/j.phytochem.2018.10.030
  9. Rebecca L. Hansen, Hongqing Guo, Yanhai Yin, Young Jin Lee. FERONIA mutation induces high levels of chloroplast-localized Arabidopsides which are involved in root growth. The Plant Journal 2019, 97 (2) , 341-351. https://doi.org/10.1111/tpj.14123
  10. Jyoti Shah, Ratnesh Chaturvedi. Lipid Signals in Plant-Pathogen Interactions. 2018,,, 292-333. https://doi.org/10.1002/9781119312994.apr0370
  11. . Annual Plant Reviews online. 2018,,https://doi.org/
  12. Abraham J. Koo. Metabolism of the plant hormone jasmonate: a sentinel for tissue damage and master regulator of stress response. Phytochemistry Reviews 2018, 17 (1) , 51-80. https://doi.org/10.1007/s11101-017-9510-8
  13. Tai-Hua Hu, Shiu-Cheung Lung, Zi-Wei Ye, Mee-Len Chye. Depletion of Arabidopsis ACYL-COA-BINDING PROTEIN3 Affects Fatty Acid Composition in the Phloem. Frontiers in Plant Science 2018, 9 https://doi.org/10.3389/fpls.2018.00002
  14. M. Soledade C. Pedras, Q. Huy To. Defense and signalling metabolites of the crucifer Erucastrum canariense : Synchronized abiotic induction of phytoalexins and galacto-oxylipins. Phytochemistry 2017, 139 , 18-24. https://doi.org/10.1016/j.phytochem.2017.03.005
  15. Marta Bjornson, Gerd Ulrich Balcke, Yanmei Xiao, Amancio de Souza, Jin-Zheng Wang, Dina Zhabinskaya, Ilias Tagkopoulos, Alain Tissier, Katayoon Dehesh. Integrated omics analyses of retrograde signaling mutant delineate interrelated stress-response strata. The Plant Journal 2017, 91 (1) , 70-84. https://doi.org/10.1111/tpj.13547
  16. Jennifer Popko. Lipid Composition of Arabidopsis thaliana Leaves. 2017,,, 1-11. https://doi.org/10.1007/978-94-007-7864-1_120-1
  17. . Encyclopedia of Lipidomics. 2017,,https://doi.org/10.1007/978-94-007-7864-1
  18. Anders K. Nilsson, Per Fahlberg, Oskar N. Johansson, Mats Hamberg, Mats X. Andersson, Mats Ellerström. The activity of HYDROPEROXIDE LYASE 1 regulates accumulation of galactolipids containing 12-oxo-phytodienoic acid in Arabidopsis. Journal of Experimental Botany 2016, 67 (17) , 5133-5144. https://doi.org/10.1093/jxb/erw278
  19. Thierry Heitz, Ekaterina Smirnova, Emilie Widemann, Yann Aubert, Franck Pinot, Rozenn Ménard. The Rise and Fall of Jasmonate Biological Activities. 2016,,, 405-426. https://doi.org/10.1007/978-3-319-25979-6_16
  20. , . Lipids in Plant and Algae Development. 2016,,https://doi.org/10.1007/978-3-319-25979-6
  21. Fakiha Afzal, Mehreen Naz, Gohar Ayub, Maria Majeed, Shizza Fatima, Rubia Zain, Sundus Hafeez, Momina Masud, Alvina Gul. Technological Platforms to Study Plant Lipidomics. 2016,,, 477-492. https://doi.org/10.1007/978-3-319-31703-8_20
  22. , , . Plant Omics: Trends and Applications. 2016,,https://doi.org/10.1007/978-3-319-31703-8
  23. Guillermo H. Jimenez-Aleman, Sandra S. Scholz, Monika Heyer, Michael Reichelt, Axel Mithöfer, Wilhelm Boland. Synthesis, metabolism and systemic transport of a fluorinated mimic of the endogenous jasmonate precursor OPC-8:0. Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids 2015, 1851 (12) , 1545-1553. https://doi.org/10.1016/j.bbalip.2015.09.002
  24. Hieu Sy Vu, Rebecca Roston, Sunitha Shiva, Manhoi Hur, Eve Syrkin Wurtele, Xuemin Wang, Jyoti Shah, Ruth Welti. Modifications of membrane lipids in response to wounding of Arabidopsis thaliana leaves. Plant Signaling & Behavior 2015, 10 (9) , e1056422. https://doi.org/10.1080/15592324.2015.1056422
  25. Anna Manara, Giovanni DalCorso, Flavia Guzzo, Antonella Furini. Loss of the Atypical Kinases ABC1K7 and ABC1K8 Changes the Lipid Composition of the Chloroplast Membrane. Plant and Cell Physiology 2015, 56 (6) , 1193-1204. https://doi.org/10.1093/pcp/pcv046
  26. G. Griffiths. Biosynthesis and analysis of plant oxylipins. Free Radical Research 2015, 49 (5) , 565-582. https://doi.org/10.3109/10715762.2014.1000318
  27. Susan E. Hartley, Rene Eschen, Julia M. Horwood, Alan C. Gange, Elizabeth M. Hill. Infection by a foliar endophyte elicits novel arabidopside-based plant defence reactions in its host, Cirsium arvense. New Phytologist 2015, 205 (2) , 816-827. https://doi.org/10.1111/nph.13067
  28. Wen-Hui Ma, Lu-Ping Qin. Chemical Constituents of Arabidopsis thaliana. Chemistry of Natural Compounds 2014, 50 (4) , 776-777. https://doi.org/10.1007/s10600-014-1083-9
  29. Yozo Okazaki, Kazuki Saito. Roles of lipids as signaling molecules and mitigators during stress response in plants. The Plant Journal 2014, 79 (4) , 584-596. https://doi.org/10.1111/tpj.12556
  30. Guitele Goldhaber-Pasillas, Natali Mustafa, Robert Verpoorte. Jasmonic Acid Effect on the Fatty Acid and Terpenoid Indole Alkaloid Accumulation in Cell Suspension Cultures of Catharanthus roseus. Molecules 2014, 19 (7) , 10242-10260. https://doi.org/10.3390/molecules190710242
  31. Anders K. Nilsson, Oskar N. Johansson, Per Fahlberg, Feray Steinhart, Mikael B. Gustavsson, Mats Ellerström, Mats X. Andersson. Formation of oxidized phosphatidylinositol and 12-oxo-phytodienoic acid containing acylated phosphatidylglycerol during the hypersensitive response in Arabidopsis. Phytochemistry 2014, 101 , 65-75. https://doi.org/10.1016/j.phytochem.2014.01.020
  32. Jiangyin Bao, Xiaoli Gao, A. Daniel Jones. Unusual negative charge-directed fragmentation: collision-induced dissociation of cyclopentenone oxylipins in negative ion mode. Rapid Communications in Mass Spectrometry 2014, 28 (5) , 457-464. https://doi.org/10.1002/rcm.6803
  33. Ivan R. Chechetkin, Alexander S. Blufard, Bulat I. Khairutdinov, Fakhima K. Mukhitova, Svetlana S. Gorina, Andrey Y. Yarin, Larisa L. Antsygina, Alexander N. Grechkin. Isolation and structure elucidation of linolipins C and D, complex oxylipins from flax leaves. Phytochemistry 2013, 96 , 110-116. https://doi.org/10.1016/j.phytochem.2013.08.010
  34. Yuki Nakamura. Galactolipid biosynthesis in flowers. Botanical Studies 2013, 54 (1) https://doi.org/10.1186/1999-3110-54-29
  35. Anders K. Nilsson, Per Fahlberg, Mats Ellerström, Mats X. Andersson. Oxo-phytodienoic acid (OPDA) is formed on fatty acids esterified to galactolipids after tissue disruption in Arabidopsis thaliana. FEBS Letters 2012, 586 (16) , 2483-2487. https://doi.org/10.1016/j.febslet.2012.06.010
  36. Marie Zábranská, Vladimír Vrkoslav, Jana Sobotníková, Josef Cvačka. Analysis of plant galactolipids by reversed-phase high-performance liquid chromatography/mass spectrometry with accurate mass measurement. Chemistry and Physics of Lipids 2012, 165 (5) , 601-607. https://doi.org/10.1016/j.chemphyslip.2012.03.002
  37. Thilani Samarakoon, Sunitha Shiva, Kaleb Lowe, Pamela Tamura, Mary R. Roth, Ruth Welti. Arabidopsis thaliana Membrane Lipid Molecular Species and Their Mass Spectral Analysis. 2012,,, 179-268. https://doi.org/10.1007/978-1-61779-995-2_13
  38. . High-Throughput Phenotyping in Plants. 2012,,https://doi.org/10.1007/978-1-61779-995-2
  39. Hideyuki Shigemori, Haruyuki Nakajyo, Yosuke Hisamatsu, Nobuharu Goto, Kosumi Yamada, Koji Hasegawa. Structure-Activity Relationships on Senescence-Promoting Effect of Arabidopsides from Arabidopsis thaliana. HETEROCYCLES 2011, 83 (1) , 57. https://doi.org/10.3987/COM-10-12092
  40. Alina Mosblech, Ivo Feussner, Ingo Heilmann. Oxylipin Signaling and Plant Growth. 2010,,, 277-291. https://doi.org/10.1007/978-3-642-03873-0_18
  41. . Lipid Signaling in Plants. 2010,,https://doi.org/10.1007/978-3-642-03873-0
  42. Michael A. Birkett. The Chemistry of Plant Signalling. 2010,,, 21-41. https://doi.org/10.1007/978-3-642-12162-3_2
  43. , . Plant Communication from an Ecological Perspective. 2010,,https://doi.org/10.1007/978-3-642-12162-3
  44. Yuki Nakamura, Mie Shimojima, Hiroyuki Ohta, Koichi Shimojima. Chapter 13 Biosynthesis and Function of Monogalactosyldiacylglycerol (MGDG), the Signature Lipid of Chloroplasts. 2010,,, 185-202. https://doi.org/10.1007/978-90-481-8531-3_13
  45. , , , , , , , . The Chloroplast. 2010,,https://doi.org/10.1007/978-90-481-8531-3
  46. Isomaro Yamaguchi, Jerry D. Cohen, Angela H. Culler, Marcel Quint, Janet P. Slovin, Masatoshi Nakajima, Shinjiro Yamaguchi, Hitoshi Sakakibara, Takeshi Kuroha, Nobuhiro Hirai, Takao Yokota, Hiroyuki Ohta, Yuichi Kobayashi, Hitoshi Mori, Yoji Sakagami. Plant Hormones. 2010,,, 9-125. https://doi.org/10.1016/B978-008045382-8.00092-7
  47. . Comprehensive Natural Products II. 2010,,https://doi.org/
  48. Hideyuki Shigemori. Bioactive Substances Involved in Life Cycle of Higher Plants. Journal of Synthetic Organic Chemistry, Japan 2010, 68 (5) , 551-562. https://doi.org/10.5059/yukigoseikyokaishi.68.551
  49. Cornelia Göbel, Ivo Feussner. Methods for the analysis of oxylipins in plants. Phytochemistry 2009, 70 (13-14) , 1485-1503. https://doi.org/10.1016/j.phytochem.2009.07.040
  50. Christine Böttcher, Stephan Pollmann. Plant oxylipins: Plant responses to 12-oxo-phytodienoic acid are governed by its specific structural and functional properties. FEBS Journal 2009, 276 (17) , 4693-4704. https://doi.org/10.1111/j.1742-4658.2009.07195.x
  51. Ivan R. Chechetkin, Fakhima K. Mukhitova, Alexander S. Blufard, Andrey Y. Yarin, Larisa L. Antsygina, Alexander N. Grechkin. Unprecedented pathogen-inducible complex oxylipins from flax - linolipins A and B. FEBS Journal 2009, 276 (16) , 4463-4472. https://doi.org/10.1111/j.1742-4658.2009.07153.x
  52. Alina Mosblech, Ivo Feussner, Ingo Heilmann. Oxylipins: Structurally diverse metabolites from fatty acid oxidation. Plant Physiology and Biochemistry 2009, 47 (6) , 511-517. https://doi.org/10.1016/j.plaphy.2008.12.011
  53. Gaetan Glauser, Elia Grata, Serge Rudaz, Jean-Luc Wolfender. High-resolution profiling of oxylipin-containing galactolipids in Arabidopsis extracts by ultra-performance liquid chromatography/time-of-flight mass spectrometry. Rapid Communications in Mass Spectrometry 2008, 22 (20) , 3154-3160. https://doi.org/10.1002/rcm.3716
  54. Otto Miersch, Jana Neumerkel, Martin Dippe, Irene Stenzel, Claus Wasternack. Hydroxylated jasmonates are commonly occurring metabolites of jasmonic acid and contribute to a partial switch-off in jasmonate signaling. New Phytologist 2007, Article ASAP.
  55. Christine Böttcher, Elmar W. Weiler. cyclo-Oxylipin-galactolipids in plants: occurrence and dynamics. Planta 2007, 226 (3) , 629-637. https://doi.org/10.1007/s00425-007-0511-5
  56. Wenyu Yang, Shivakumar P. Devaiah, Xiangqing Pan, Giorgis Isaac, Ruth Welti, Xuemin Wang. AtPLAI Is an Acyl Hydrolase Involved in Basal Jasmonic Acid Production and Arabidopsis Resistance to Botrytis cinerea. Journal of Biological Chemistry 2007, 282 (25) , 18116-18128. https://doi.org/10.1074/jbc.M700405200
  57. Steven Wynn Esch, Pamela Tamura, Alexis A. Sparks, Mary R. Roth, Shivakumar P. Devaiah, Ernst Heinz, Xuemin Wang, Todd D. Williams, Ruth Welti. Rapid characterization of the fatty acyl composition of complex lipids by collision-induced dissociation time-of-flight mass spectrometry. Journal of Lipid Research 2007, 48 (1) , 235-241. https://doi.org/10.1194/jlr.D600034-JLR200
  58. Mats X. Andersson, Mats Hamberg, Olga Kourtchenko, Åsa Brunnström, Kerry L. McPhail, William H. Gerwick, Cornelia Göbel, Ivo Feussner, Mats Ellerström. Oxylipin Profiling of the Hypersensitive Response in Arabidopsis thaliana. Journal of Biological Chemistry 2006, 281 (42) , 31528-31537. https://doi.org/10.1074/jbc.M604820200
  59. Mats X. Andersson, Mats Hamberg, Olga Kourtchenko, Åsa Brunnstro¨m, Kerry L. McPhail, William H. Gerwick, Cornelia Go¨bel, Ivo Feussner, Mats Ellerstro¨m. Oxylipin Profiling of the Hypersensitive Response in Arabidopsis thaliana. Journal of Biological Chemistry 2006, 281 (42) , 31528-31537. https://doi.org/10.1016/S0021-9258(19)84066-8
  60. Dominique Lafont, Frédéric Carrière, Francine Ferrato, Paul Boullanger. Syntheses of an α-d-Gal-(1→6)-β-d-Gal diglyceride, as lipase substrate. Carbohydrate Research 2006, 341 (6) , 695-704. https://doi.org/10.1016/j.carres.2006.01.021
  61. Hideyuki Shigemori, Haruyuki Nakajyo, Yosuke Hisamatsu, Mitsuhiro Sekiguchi, Nobuharu Goto, Koji Hasegawa. Arabidopside F, a New Oxylipin from Arabidopsis thaliana. HETEROCYCLES 2006, 69 (1) , 295. https://doi.org/10.3987/COM-06-S(O)33
  62. Andreas Schaller, Annick Stintzi. Jasmonate Biosynthesis and Signaling for Induced Plant Defense against Herbivory. ,,, 349-366. https://doi.org/10.1007/978-1-4020-8182-8_17
  63. . Induced Plant Resistance to Herbivory. 2008,,https://doi.org/10.1007/978-1-4020-8182-8
  64. M. X. Andersson, P. Dörmann. Chloroplast Membrane Lipid Biosynthesis and Transport. ,,, 125-158. https://doi.org/10.1007/978-3-540-68696-5_4
  65. , . The Chloroplast. 2009,,https://doi.org/10.1007/978-3-540-68696-5
  66. F. Bouvier, A. S. Mialoundama, B. Camara. A Sentinel Role for Plastids. ,,, 267-292. https://doi.org/10.1007/978-3-540-68696-5_9
  67. , . The Chloroplast. 2009,,https://doi.org/10.1007/978-3-540-68696-5

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