Control of cytokinin and auxin homeostasis in cyanobacteria and algae

. 2017 Jan ; 119 (1) : 151-166. [epub] 20161005

Jazyk angličtina Země Velká Británie, Anglie Médium print-electronic

Typ dokumentu časopisecké články, práce podpořená grantem

Perzistentní odkaz   https://www.medvik.cz/link/pmid27707748

BACKGROUND AND AIMS: The metabolism of cytokinins (CKs) and auxins in vascular plants is relatively well understood, but data concerning their metabolic pathways in non-vascular plants are still rather rare. With the aim of filling this gap, 20 representatives of taxonomically major lineages of cyanobacteria and algae from Cyanophyceae, Xanthophyceae, Eustigmatophyceae, Porphyridiophyceae, Chlorophyceae, Ulvophyceae, Trebouxiophyceae, Zygnematophyceae and Klebsormidiophyceae were analysed for endogenous profiles of CKs and auxins and some of them were used for studies of the metabolic fate of exogenously applied radiolabelled CK, [3H]trans-zeatin (transZ) and auxin ([3H]indole-3-acetic acid (IAA)), and the dynamics of endogenous CK and auxin pools during algal growth and cell division. METHODS: Quantification of phytohormone levels was performed by high-performance or ultrahigh-performance liquid chromatography-electrospray tandem mass spectrometry (HPLC-MS/MS, UHPLC-MS/MS). The dynamics of exogenously applied [3H]transZ and [3H]IAA in cell cultures were monitored by HPLC with on-line radioactivity detection. KEY RESULTS: The comprehensive screen of selected cyanobacteria and algae for endogenous CKs revealed a predominance of bioactive and phosphate CK forms while O- and N-glucosides evidently did not contribute greatly to the total CK pool. The abundance of cis-zeatin-type CKs and occurrence of CK 2-methylthio derivatives pointed to the tRNA pathway as a substantial source of CKs. The importance of the tRNA biosynthetic pathway was proved by the detection of tRNA-bound CKs during the course of Scenedesmus obliquus growth. Among auxins, free IAA and its oxidation catabolite 2-oxindole-3-acetic acid represented the prevailing endogenous forms. After treatment with [3H]IAA, IAA-aspartate and indole-3-acetyl-1-glucosyl ester were detected as major auxin metabolites. Moreover, different dynamics of endogenous CKs and auxin profiles during S. obliquus culture clearly demonstrated diverse roles of both phytohormones in algal growth and cell division. CONCLUSIONS: Our data suggest the existence and functioning of a complex network of metabolic pathways and activity control of CKs and auxins in cyanobacteria and algae that apparently differ from those in vascular plants.

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Abdel-Raouf N, Al-Homaidan AA, Ibraheem IBM. 2012. Agricultural importance of algae. African Journal of Biotechnology 11: 11648–11658.

Abe H, Uchiyama M, Sato R. 1974. Isolation of phenylacetic acid and its p-hydroxy derivative as auxin-like substances from Undaria pinnatifida. Agricultural and Biological Chemistry 38: 897–898.

Anantharaman V, Aravind L. 2001. The CHASE domain: a predicted ligand-binding module in plant cytokinin receptors and other eukaryotic and bacterial receptors. Trends in Biochemical Sciences 26: 579–582. PubMed

Ashen JB, Cohen JD, Goff LJ. 1999. GC-SIM-MS detection and quantification of free indole-3-acetic acid in bacterial galls on the marine alga Prionitis lanceolata (Rhodophyta). Journal of Phycology 35: 493–500.

Le Bail A, Billoud B, Kowalczyk N, et al. 2010. Auxin metabolism and function in the multicellular brown alga Ectocarpus siliculosus. American Society of Plant Biologists 153: 128–144. PubMed PMC

Benková E, Ivanchenko MG, Friml J, Shishkova S, Dubrovsky JG. 2009. A morphogenetic trigger: is there an emerging concept in plant developmental biology? Trends in Plant Science 14: 189–193. PubMed

Blilou I, Xu J, Wildwater M, Willemsen V, et al. 2005. The PIN auxin efflux facilitator network controls growth and patterning in Arabidopsis roots. Nature 433: 39–44. PubMed

Coenen C, Lomax TL. 1997. Auxin-cytokinin interactions in higher plants: old problems and new tools. Trends in Plant Science 2: 351–356. PubMed

Cooke TJ, Poli DB, Sztein AE, Cohen JD. 2002. Evolutionary patterns in auxin action. Plant Molecular Biology 49: 319–338. PubMed

Cheng Y, Dai X, Zhao Y. 2006. Auxin biosynthesis by the YUCCA flavin monooxygenases controls the formation of floral organs and vascular tissues in Arabidopsis. Genes & Development 20: 1790–1799. PubMed PMC

Cheng Y, Dai X, Zhao Y. 2007. Auxin synthesized by the YUCCA flavin monooxygenases is essential for embryogenesis and leaf formation in Arabidopsis. The Plant Cell 19: 2430–2439. PubMed PMC

Czerpak R, Bajguz A, Bialecka B, Wierzcholowska LE, Wolanska MM. 1994. Effect of auxin precursors and chemical analogs on the growth and chemical composition in Chlorella pyrenoidosa Chick. Acta Societatis Botanicorum Poloniae 6: 279–286.

Djilianov DL, Dobrev PI, Moyankova DP, et al. 2013. Dynamics of endogenous phytohormones during desiccation and recovery of the resurrection plant species Haberlea rhodopensis. Journal of Plant Growth Regulation 32: 564–574.

Dobrev PI, Kamínek M. 2002. Fast and efficient separation of cytokinins from auxin and abscisic acid and their purification using mixed-mode solid-phase extraction. Journal of Chromatography A 950: 21–29. PubMed

Dobrev PI, Havlíček L, Vágner M, Malbeck J, Kamínek M. 2005. Purification and determination of plant hormones auxin and abscisic acid using solid phase extraction and two-dimensional high performance liquid chromatography. Journal of Chromatography A 1075: 159–166. PubMed

Frébort I, Kowalska M, Hluska T, Frébortová J, Galuszka P. 2011. Evolution of cytokinin biosynthesis and degradation. Journal of Experimental Botany 62: 2431–2452. PubMed

Frébortová J, Greplová M, Seidl MF, Heyl A, Frébort I. 2015. Biochemical characterization of puative adenylate dimethylallyltransferase and cytokinin dehydrogenase from Nostoc sp. PCC 7120. PLoS One 10: e0138468. PubMed PMC

Friml J, Vieten A, Sauer M, et al. 2003. Efflux-dependent auxin gradients establish the apical-basal axis of Arabidopsis. Nature 426: 147–153. PubMed

Gajdošová S, Spíchal L, Kamínek M, et al. 2011. Distribution, biological activities, metabolism, and the conceivable function of cis-zeatin-type cytokinins in plants. Journal of Experimental Botany 62: 2827–2840. PubMed

Gaudinová A, Dobrev PI, Šolcová B, et al. 2005. The involvement of cytokinin oxidase/dehydrogenase and zeatin reductase in regulation of cytokinin levels in pea (Pisum sativum L.) leaves. Journal of Plant Growth Regulation 24: 188–200.

Hashtroudi MS, Ghassempour A, Riahi H, Shariatmadari Z, Khanjir M. 2013. Endogenous auxins in plant growth-promoting Cyanobacteria – Anabaena vaginicola and Nostoc calcicola. Journal of Applied Phycology 25: 379–386.

Hussain A, Krischke M, Roitsch T, Hasnain S. 2010. Rapid determination of cytokinins and auxin in cyanobacteria. Current Microbiology 61: 361–369. PubMed

Hwang I, Sakakibara H. 2006. Cytokinin biosynthesis and perception. Physiologia Plantarum 126: 528–538.

Hwang I, Sheen J, Müller B. 2012. Cytokinin signaling networks. Annual Review of Plant Biology 63: 353–380. PubMed

Jusoh M, Loh SH, Chuah TS, Aziz A, Cha TS. 2015. Indole-3-acetic acid (IAA) induced changes in iol content, fatty acid profiles and expression of four fatty acid biosynthetic genes in Chlorella vulgaris at early stationary growth phase. Phytochemistry 111: 65–71. PubMed

Kai K, Horita J, Wakasa K, Miyagawa H. 2007a. Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana. Phytochemistry 68: 1651–1663. PubMed

Kai K, Nakamura S, Wakasa K, Miyagawa H. 2007b. Facile preparation of deuterium-labeled standards of indole-3-acetic acid (IAA) and its metabolites to quantitatively analyze the disposition of exogenous IAA in Arabidopsis thaliana. Bioscience Biotechnology and Biochemistry 71: 1946–1954. PubMed

Kakimoto T. 2003. Biosynthesis of cytokinins. Journal of Plant Research 116: 233–239. PubMed

Kamínek M, Březinová A, Gaudinová A, Motyka V, Vaňková R, Zažímalová E. 2000. Purine cytokinins: a proposal of abbreviations. Plant Growth Regulation 32: 253–256.

Kenrick P, Crane PR. 1997. The origin and early evolution of plants on land. Nature 389: 33–39.

Kieber JJ, Schaller GE. 2014. Cytokinins. The Arabidopsis Book 11:e0168. doi:10.1199/tab.0168. PubMed PMC

Kiseleva AA, Tarachvskaya ER, Shishova MF. 2012. Biosynthesis of phytohormones in algae. Russian Journal of Plant Physiology 59: 595–610.

Korasick DA, Enders TA, Strader LC. 2013. Auxin biosynthesis and storage forms. Journal of Experimental Botany 64: 2541–2555. PubMed PMC

Lewis LA, McCourt RM. 2004. Green algae and the origin of land plants. American Journal of Botany 91: 1535–1556. PubMed

Ljung K. 2013. Auxin metabolism and homeostasis during plant development. Development 140: 943–950. PubMed

Ljung K, Hull AK, Kowalczyk M, et al. 2002. Biosynthesis, conjugation, catabolism and homeostasis of indole-3-acetic acid in Arabidopsis thaliana. Plant Molecular Biology 49: 249–272. PubMed

Löbler M, Klämbt D. 1985. Auxin-binding protein from coleoptile membranes of corn (Zea mays L.). I. Purification by immunological methods and characterization. Journal of Biological Chemistry 260: 9848–9853. PubMed

Lu Y, Xu J. 2015. Phytohormones in microalgae: a new opportunity for microalgal biotechnology? Trends in Plant Science 20: 273–282. PubMed

Lu Y, Tarkowská D, Turečková V, et al. 2014. Antagonistic roles of abscisic acid and cytokinin during response to nitrogen depletion in oleaginous microalga Nannochloropsis oceanica expand the evolutionary breadth of phytohormone function. The Plant Journal 80: 52–68. PubMed

Ludwig-Müller J. 2011. Auxin conjugates: their role for plant development and in the evolution of land plants. Journal of Experimental Botany 62: 1757–1773. PubMed

Maass H, Klämbt D. 1981. On the biogenesis of cytokinins in roots of Phaseolus vulgaris. Planta 151: 353–358. PubMed

Mähönen AP, Tusscher K, Siligato R, et al. 2014. PLETHORA gradient formation mechanism separates auxin responses. Nature 515: 125–129. PubMed PMC

Maor R. 2010. Compositions and methods for increasing oil content in algae. European Patent Application WO2010IL00247 20100324.

Martin RC, Mok MC, Shaw G, Mok DWS. 1989. An enzyme mediating the conversion of zeatin to dihydrozeatin in Phaseolus embryos. Plant Physiology 90: 1630–1635. PubMed PMC

Mazhar S, Cohen JD, Hasnain S. 2013. Auxin producing non-heterocystous cyanobacteria and their impact on the growth and endogenous auxin homeostasis of wheat. Journal of Basic Microbiology 53: 996–1003. PubMed

Mazur H, Konop A, Synak R. 2001. Indole-3-acetic acid in the culture medium of two axenic green microalgae. Journal of Applied Phycology 13: 35–42.

Miller CO, Skoog F, von Saltza MH, Strong FM. 1956. Isolation, structure and synthesis of kinetin, a substance promoting cell division. Journal of American Chemical Society 78: 1375–1380.

Morrison EN, Knowles S, Hayward A, Thorn RG, Saville BJ, Emery RJN. 2015. Detection of phytohormones in temperate forest fungi predicts consistent abscisic acid production and a common pathway for cytokinin biosynthesis. Mycologia 107: 245–257. PubMed

Motyka V, Vaňková R, Čapková V, Petrášek J, Kamínek M, Schmülling T. 2003. Cytokinin-induced upregulation of cytokinin oxidase activity in tobacco includes changes in enzyme glycosylation and secretion. Physiologia Plantarum 117: 11–21.

Normanly J. 2010. Approaching cellular and molecular resolution of auxin biosynthesis and metabolism. Cold Spring Harbor Perspectives in Biology 2: a001594. PubMed PMC

Normanly J, Cohen JD, Fink GR. 1993. Arabidopsis thaliana auxotrophs reveal a tryptophan-independent biosynthetic pathway for indole-3-acetic acid. Proceedings of the National Academy of Sciences of the USA 21: 10355–10359. PubMed PMC

Novák O, Tarkowski P, Tarkowská D, Doležal K, Lenobel R, Strnad M. 2003. Quantitative analysis of cytokinins in plants by liquid chromatography–single-quadrupole mass spectrometry. Analytica Chimica Acta 480: 207–218.

Novák O, Hauserová E, Amakorová P, Doležal K, Strnad M. 2008. Cytokinin profiling in plant tissues using ultra-performance liquid chromatography-electrospray tandem mass spectrometry. Phytochemistry 69: 2214–2224. PubMed

Nowak J, Sonaike B, Lawson GW. 1988. Auxin induced stress tolerance in algae. Environmental Pollution 51: 213–218. PubMed

Ouyang J, Shao X, Li J. 2000. Indole-3-glycerol phosphate, a branchpoint of indole-3-acetic acid biosynthesis from the tryptophan biosynthetic pathway in Arabidopsis thaliana. The Plant Journal 24: 327–334. PubMed

Ördög V, Stirk WA, van Staden J, Novák O, Strnad M. 2004. Endogenous cytokinins in three genera of microalgae from the Chlorophyta. Journal of Phycology 40: 88–95.

Östin A, Kowalyczk M, Bhalerao RP, Sandberg G. 1998. Metabolism of indole-3-acetic acid in Arabidopsis. Plant Physiology 118: 285–296. PubMed PMC

Park W, Yoo G, Moon M, Kim C, Choi YE, Yang JW. 2013. Phytohormone supplementation significantly increases growth of Chlamydomonas reinhardtii cultivated for biodiesel production. Applied Biochemistry and Biotechnology 171: 1128–1142. PubMed

Pernisová M, Kuderová A, Hejátko J. 2011. Cytokinin and auxin interactions in plant development: metabolism, signalling, transport and gene expression. Current Protein and Peptide Science 12: 137–147. PubMed

Pils B, Heyl A. 2009. Unraveling the evolution of cytokinin signaling. Plant Physiology 151: 782–791. PubMed PMC

Piotrowska-Niczyporuk A, Bajguz A. 2014. The effect of natural and synthetic auxins on the growth, metabolite content and antioxidant response of green alga Chlorella vulgaris (Trebouxiophyceae). Plant Growth Regulation 73: 57–66.

Přibyl P, Cepák V, Kaštánek P, Zachleder V. 2015. Elevated production of carotenoids by a new isolate of Scenedesmus sp. Algal Research 11: 22–27.

Prinsen E, Kamínek M, van Onckelen HA. 1997. Cytokinin biosynthesis: a black box? Plant Growth Regulation 23: 3–15.

Rocha OP, Felício R, Rodrigues AHB, et al. 2011. Chemical profile and biological potential of non-polar fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta). Molecules 16: 7105–7114. PubMed PMC

Riisberg I, Orr RJS, Kluge R, et al. 2009. Seven gene phylogeny of heterokonts. Protist 160: 191–204. PubMed

Ruhfel BR, Gitzendanner MA, Soltis PS, Soltis DE, Burleigh JG. 2014. From algae to angiosperms – inferring the phylogeny of green plants (Viridiplantae) from 360 plastid genomes. BMC Evolutionary Biology 14: 23. PubMed PMC

Sakakibara H. 2006. Cytokinins: activity, biosynthesis, and translocation. Annual Review of Plant Biology 57: 431–449. PubMed

Santner A, Calderon-Villalobos LIA, Estelle M. 2009. Plant hormones are versatile chemical regulators of plant growth. Nature Chemical Biology 5: 301–307. PubMed

Schmülling T, Werner T, Riefler M, Krupková E, Bartriba y Manns I. 2003. Structure and function of cytokinin oxidase/dehydrogenase genes of maize, rice, Arabidopsis and other species. Journal of Plant Research 116: 241–252. PubMed

Schneider EA, Kazakoff CW, Wightman F. 1985. Gas chromatography–mass spectrometry evidence for several endogenous auxins in pea seedling organs. Planta 165: 232–241. PubMed

Selivankina SY, Zubkova NK, Kupriyanova EV, et al. 2006. Cyanobacteria respond to cytokinin. Russian Journal of Plant Physiology 53: 751–755.

Sergeeva E, Liaimer A, Bergman B. 2002. Evidence for production of the phytohormone indole-3-acetic acid by cyanobacteria. Planta 215: 229–238. PubMed

Shimizu-Mitao Y, Kakimoto T. 2014. Auxin sensitivities of all Arabidopsis Aux/IAAs for degradation in the presence of every TIR1/AFB. Plant Cell Physiology 55: 1450–1459. PubMed

Spíchal L. 2012. Cytokinins – recent news and views of evolutionally old molecules. Functional Plant Biology 39: 267–284. PubMed

Stirk WA, Ördög V, van Staden J. 1999. Identification of the cytokinin isopentenyladenine in a strain of Arthronema africanum (Cyanobacteria). Journal of Phycology 35: 89–92.

Stirk WA, Ördög V, van Staden J, Jäger K. 2002. Cytokinin- and auxin-like activity in Cyanophyta and microalgae. Journal of Applied Phycology 14: 215–221.

Stirk WA, Novák O, Strnad M, van Staden J. 2003. Cytokinins in macroalgae. Plant Growth Regulation 41: 13–24.

Stirk WA, van Staden J, Novák O, et al. 2011. Changes in endogenous cytokinin concentrations in Chlorella (Chlorophyceae) in relation to light and the cell cycle. Journal of Phycology 47: 291–301. PubMed

Stirk WA, Václavíková K, Novák O, et al. 2012. Involvement of cis-zeatin, dihydrozeatin, and aromatic cytokinins in germination and seedling establishment of maize, oats and lucerne. Journal of Plant Growth Regulation 31: 392–405.

Stirk WA, Ördög V, Novák O, Rolčík J, Strnad M, Van Staden J. 2013. Auxin and cytokinin relationships in 24 microalgal strains. Journal of Phycology 49: 459–467. PubMed

Stirk WA, Tarkowska D, Turecova V, Strnad M, van Staden J. 2014. Abscisic acid, gibberellins and brassinosteroids in Kelpak (R), a commercial seaweed extract made from Ecklonia maxima. Journal of Applied Phycology 26: 561–567.

Sugawara S, Mashiguchi K, Tanaka K, et al. 2015. Distinct characteristics of indole-3-acetic acid and phenylacetic acid, two common auxins in plants. Plant Cell Physiology 56: 151–166.. PubMed PMC

Svačinová J, Novák O, Plačková L, et al. 2012. A new approach for cytokinin isolation from Arabidopsis tissues using miniaturized purification: pipette tip solid-phase extraction. Plant Methods 8: 17. PubMed PMC

Swaminathan S, Bock RM. 1977. Isolation and identification of cytokinins from Euglena gracilis transfer ribonucleic acid. Biochemistry 16: 1355–1360. PubMed

Šimura J, Novák O, Strnad M, Nedbal L. 2014. Cytokinin profiling in Cyanobacteria and microalgae species using UHPLC-MS/MS. In: Abstracts of the International Symposium 2014: Auxins and Cytokinins in Plant Development … and Interactions with Other Phytohormones, Prague, Czech Republic. Abstract P1–15.

Takei K, Yamaya T, Sakakibara H. 2004. Arabidopsis CYP735A1 and CYP735A2 encode cytokinin hydroxylases that catalyze the biosynthesis of trans-zeatin. Journal of Biological Chemistry 279: 41866–41872. PubMed

Tarakhovskaya ER, Maslov YI, Shishova MF. 2007. Phytohormones in algae. Russian Journal of Plant Physiology 54: 186–194.

Tarkowski P, Václavíková K, Novák O, et al. 2010. Analysis of 2-methylthio-derivatives of isoprenoid cytokinins by liquid chromatography-tandem mass spectrometry. Analytica Chimica Acta 680: 86–91. PubMed

Tivendale ND, Ross JJ, Cohen JD. 2014. The shifting paradigms of auxin biosynthesis. Trends in Plant Science 19: 44–51. PubMed

Yevdakova NA, Motyka V, Malbeck J, et al. 2008. Evidence for importance of tRNA-dependent cytokinin biosynthetic pathway in the moss Physcomitrella patens. Journal of Plant Growth Regulation 27: 271–281.

Yokoya NS, Stirk WA, van Staden J, et al. 2010. Endogenous cytokinins, auxins and abscisic acid in red algae from Brazil. Journal of Phycology 46: 1198–1205.

Yokoya NS, Yoneshigue-Valentin Y. 2011. Micropropagation as a tool for sustainable utilization and conservation of populations of Rhodophyta. Revista Brasileira De Farmacognosia – Brazilian Journal of Pharmacognosy 21: 334–339.

Yue J, Xiangyang H, Huang J. 2014. Origin of plant auxin biosynthesis. Trends in Plant Science 19: 764–770. PubMed

Varalakshmi P, Malliga P. 2012. Evidence for production of indole-3-acetic acid from a fresh water cyanobacteria (Oscillatoria annae) on the growth of H. annus. International Journal of Scientific and Research Publications 3: 1–15.

Wang B, Chu J, Yu T, et al. 2015. Tryptophan-independent auxin biosynthesis contributes to early embryogenesis in Arabidopsis. Proceedings of the National Academy of Sciences of the USA 112: 4821–4826. PubMed PMC

Wightman F, Lighty DL. 1982. Identification of phenylacetic acid as natural auxin in the shoots of higher plants. Physiologia Plantarum 55: 17–24.

Woodward AW, Bartel B. 2005. Auxin: regulation, action, and interaction. Annals of Botany 95: 707–735. PubMed PMC

Záveská Drábková L, Dobrev PI, Motyka V. 2015. Phytohormone profiling across the bryophytes. PLoS One 10: e0125411. PubMed PMC

Žižková E, Dobrev PI, Muhovski Y, et al. 2015. Tomato (Solanum lycopersicum L.) SlIPT3 and SlIPT4 isopentenyltransferases mediate salt stress response in tomato. BMC Plant Biology 15: 85. PubMed PMC

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