Published July 4, 2019 | Version v1

Should I stay or should I go: are chlorogenic acids mobilized towards lignin biosynthesis?

  • 1. Department of Plant Biology, Institute of Biology, State University of Campinas, Campinas, SP, Brazil

Description

Silva, Nathalia Volpi e, Mazzafera, Paulo, Cesarino, Igor (2019): Should I stay or should I go: are chlorogenic acids mobilized towards lignin biosynthesis? Phytochemistry 166: 1-7, DOI: 10.1016/j.phytochem.2019.112063, URL: http://dx.doi.org/10.1016/j.phytochem.2019.112063

Files

Restricted

The record is publicly accessible, but files are restricted. Log in to check if you have access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:3579CB4DF157FF8BFFF4FF9C4C58FFA0

References

  • Aerts, R.J., Baumann, T.W., 1994. Distribution and utilization of chlorogenic acid in Coffea seedlings. J. Exp. Bot. 45, 497-503. https://doi.org/10.1093/jxb/45.4.497.
  • Barros, J., Escamilla-Trevino, L., Song, L., Rao, X., Serrani-Yarce, J.C., Palacios, M.D., Engle, N., Choudhury, F.K., Tschaplinski, T.J., Venables, B.J., Mittler, R., Dixon, R.A., 2019. 4-Coumarate 3-hydroxylase in the lignin biosynthesis pathway is a cytosolic ascorbate peroxidase. Nat. Commun. 10 1994. https://doi.org/10.1038/s41467-019- 10082-7.
  • Barros, J., Serk, H., Granlund, I., Pesquet, E., 2015. The cell biology of lignification in higher plants. Ann. Bot. 115, 1053-1074. https://doi.org/10.1093/aob/mcv046.
  • Cesarino, I., 2019. Structural features and regulation of lignin deposited upon biotic and abiotic stresses. Curr. Opin. Biotechnol., Food Biotechnology • Plant Biotechnology 56, 209-214. https://doi.org/10.1016/j.copbio.2018.12.012.
  • Cle, C., Hill, L.M., Niggeweg, R., Martin, C.R., Guisez, Y., Prinsen, E., Jansen, M.A.K., 2008. Modulation of chlorogenic acid biosynthesis in Solanum lycopersicum: Consequences for phenolic accumulation and UV-tolerance. Phytochemistry 69, 2149-2156. https://doi.org/10.1016/j.phytochem.2008.04.024.
  • Clifford, M.N., 2000. Chlorogenic acids and other cinnamates - nature, occurrence, dietary burden, absorption and metabolism. J. Sci. Food Agric. 80, 1033-1043. https://doi.org/10.1002/(SICI)1097-0010(20000515)80:7<1033::AID-JSFA595>3.
  • Clifford, M.N., Jaganath, I.B., Ludwig, I.A., Crozier, A., 2017. Chlorogenic acids and the acyl-quinic acids: Discovery, biosynthesis, bioavailability and bioactivity. Nat. Prod. Rep. 34, 1391-1421. https://doi.org/10.1039/C7NP00030H.
  • Diaz, J., Barcelo, A.R., Caceres, F.M.D., 1997. Changes in shikimate dehydrogenase and the end products of the shikimate pathway, chlorogenic acid and lignins, during the early development of seedlings of Capsicum annuum. New Phytol. 136, 183-188. https://doi.org/10.1046/j.1469-8137.1997.00743.x.
  • Escamilla-Trevino, L.L., Shen, H., Hernandez, T., Yin, Y., Xu, Y., Dixon, R.A., 2014. Early lignin pathway enzymes and routes to chlorogenic acid in switchgrass (Panicum virgatum L.). Plant Mol. Biol. 84, 565-576. https://doi.org/10.1007/s11103-013- 0152-y.
  • Garrett, R., Rezende, C.M., Ifa, D.R., 2016. Revealing the spatial distribution of chlorogenic acids and sucrose across coffee bean endosperm by desorption electrospray ionization-mass spectrometry imaging. LWT - Food Sci. Technol. (Lebensmittel- Wissenschaft -Technol.) 65, 711-717. https://doi.org/10.1016/j.lwt.2015.08.062.
  • Ha, C.M., Escamilla-Trevino, L., Yarce, J.C.S., Kim, H., Ralph, J., Chen, F., Dixon, R.A., 2016. An essential role of caffeoyl shikimate esterase in monolignol biosynthesis in Medicago truncatula. Plant J. 86, 363-375. https://doi.org/10.1111/tpj.13177.
  • Hoffmann, L., Besseau, S., Geoffroy, P., Ritzenthaler, C., Meyer, D., Lapierre, C., Pollet, B., Legrand, M., 2004. Silencing of hydroxycinnamoyl-coenzyme a shikimate/quinate hydroxycinnamoyltransferase affects phenylpropanoid biosynthesis. Plant Cell 16, 1446-1465. https://doi.org/10.1105/tpc.020297.
  • Hoffmann, L., Maury, S., Martz, F., Geoffroy, P., Legrand, M., 2003. Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism. J. Biol. Chem. 278, 95-103. https://doi. org/10.1074/jbc.M209362200.
  • Islam, S., 2006. Sweetpotato (Ipomoea batatas L.) leaf: Its potential effect on human health and nutrition. J. Food Sci. 71, R13-R121. https://doi.org/10.1111/j.1365-2621. 2006.tb08912.x.
  • Joet, T., Laffargue, A., Salmona, J., Doulbeau, S., Descroix, F., Bertrand, B., Kochko, A. de, Dussert, S., 2009. Metabolic pathways in tropical dicotyledonous albuminous seeds: Coffea arabica as a case study. New Phytol. 182, 146-162. https://doi.org/10.1111/j. 1469-8137.2008.02742.x.
  • Kundu, A., Vadassery, J., 2019. Chlorogenic acid-mediated chemical defence of plants against insect herbivores. Plant Biol. 21, 185-189. https://doi.org/10.1111/plb. 12947.
  • Lallemand, L.A., Zubieta, C., Lee, S.G., Wang, Y., Acajjaoui, S., Timmins, J., McSweeney, S., Jez, J.M., McCarthy, J.G., McCarthy, A.A., 2012. A structural basis for the biosynthesis of the major chlorogenic acids found in coffee. Plant Physiol. 160, 249-260. https://doi.org/10.1104/pp.112.202051.
  • Legrand, G., Delporte, M., Khelifi, C., Harant, A., Vuylsteker, C., Morchen, M., Hance, P., Hilbert, J.-L., Gagneul, D., 2016. Identification and characterization of five BAHD acyltransferases involved in hydroxycinnamoyl ester metabolism in chicory. Front. Plant Sci. 7. https://doi.org/10.3389/fpls.2016.00741.
  • Liu, Q., Yao, L., Xu, Y., Cheng, H., Wang, W., Liu, Z., Liu, J., Cui, X., Zhou, Y., Ning, W., 2019. In vitro evaluation of hydroxycinnamoyl CoA:quinate hydroxycinnamoyl transferase expression and regulation in Taraxacum antungense in relation to 5-caffeoylquinic acid production. Phytochemistry 162, 148-156. https://doi.org/10. 1016/j.phytochem.2019.02.014.
  • Mahon, E.L., Mansfield, S.D., 2019. Tailor-made trees: Engineering lignin for ease of processing and tomorrow's bioeconomy. Curr. Opin. Biotechnol., Food Biotechnology • Plant Biotechnology 56, 147-155. https://doi.org/10.1016/j.copbio.2018.10.014.
  • Martinez, G., Regente, M., Jacobi, S., Del Rio, M., Pinedo, M., de la Canal, L., 2017. Chlorogenic acid is a fungicide active against phytopathogenic fungi. Pestic. Biochem. Physiol. 140, 30-35. https://doi.org/10.1016/j.pestbp.2017.05.012.
  • Moglia, A., Lanteri, S., Comino, C., Hill, L., Knevitt, D., Cagliero, C., Rubiolo, P., Bornemann, S., Martin, C., 2014. Dual catalytic activity of Hydroxycinnamoyl-Coenzyme A Quinate Transferase from tomato allows it to moonlight in the synthesis of both mono- and dicaffeoylquinic acids. Plant Physiol. 166, 1777-1787. https:// doi.org/10.1104/pp.114.251371.
  • Nakajima, Y., Shimazawa, M., Mishima, S., Hara, H., 2007. Water extract of propolis and its main constituents, caffeoylquinic acid derivatives, exert neuroprotective effects via antioxidant actions. Life Sci. 80, 370-377. https://doi.org/10.1016/j.lfs.2006.09. 017.
  • Nelson, R.S., Stewart, C.N., Gou, J., Holladay, S., Gallego-Giraldo, L., Flanagan, A., Mann, D.G.J., Hisano, H., Wuddineh, W.A., Poovaiah, C.R., Srivastava, A., Biswal, A.K., Shen, H., Escamilla-Trevino, L.L., Yang, J., Hardin, C.F., Nandakumar, R., Fu, C., Zhang, J., Xiao, X., Percifield, R., Chen, F., Bennetzen, J.L., Udvardi, M., Mazarei, M., Dixon, R.A., Wang, Z.-Y., Tang, Y., Mohnen, D., Davison, B.H., 2017. Development and use of a switchgrass (Panicum virgatum L.) transformation pipeline by the BioEnergy Science Center to evaluate plants for reduced cell wall recalcitrance. Biotechnol. Biofuels 10, 309. https://doi.org/10.1186/s13068-017-0991-x.
  • Niggeweg, R., Michael, A.J., Martin, C., 2004. Engineering plants with increased levels of the antioxidant chlorogenic acid. Nat. Biotechnol. 22, 746. https://doi.org/10.1038/ nbt966.
  • Payyavula, R.S., Shakya, R., Sengoda, V.G., Munyaneza, J.E., Swamy, P., Navarre, D.A., 2015. Synthesis and regulation of chlorogenic acid in potato: Rerouting phenylpropanoid flux in HQT-silenced lines. Plant Biotechnol. J. 13, 551-564. https://doi.org/ 10.1111/pbi.12280.
  • Pereira, L., Domingues-Junior, A.P., Jansen, S., Choat, B., Mazzafera, P., 2018. Is embolism resistance in plant xylem associated with quantity and characteristics of lignin? Trees (Berl.) 32, 349-358. https://doi.org/10.1007/s00468-017-1574-y.
  • Ralph, J., Lapierre, C., Boerjan, W., 2019. Lignin structure and its engineering. Curr. Opin. Biotechnol., Food Biotechnology • Plant Biotechnology 56, 240-249. https:// doi.org/10.1016/j.copbio.2019.02.019.
  • Renault, H., Werck-Reichhart, D., Weng, J.-K., 2019. Harnessing lignin evolution for biotechnological applications. Curr. Opin. Biotechnol., Food Biotechnology • Plant Biotechnology 56, 105-111. https://doi.org/10.1016/j.copbio.2018.10.011.
  • Saleme, M. de L.S., Cesarino, I., Vargas, L., Kim, H., Vanholme, R., Goeminne, G., Acker, R.V., Fonseca, F.C. de A., Pallidis, A., Voorend, W., Junior, J.N., Padmakshan, D., Doorsselaere, J.V., Ralph, J., Boerjan, W., 2017. Silencing CAFFEOYL SHIKIMATE ESTERASE affects lignification and improves saccharification in poplar. Plant Physiol. 175, 1040-1057. https://doi.org/10.1104/pp.17.00920.
  • Shadle, G., Chen, F., Srinivasa Reddy, M.S., Jackson, L., Nakashima, J., Dixon, R.A., 2007. Down-regulation of hydroxycinnamoyl CoA:shikimate hydroxycinnamoyl transferase in transgenic alfalfa affects lignification, development and forage quality. Phytochemistry 68, 1521-1529. https://doi.org/10.1016/j.phytochem.2007.03.022.
  • Shen, H., Fu, C., Xiao, X., Ray, T., Tang, Y., Wang, Z., Chen, F., 2009. Developmental control of lignification in stems of lowland switchgrass variety Alamo and the effects on saccharification efficiency. BioEnergy Res. 2, 233-245. https://doi.org/10.1007/ s12155-009-9058-6.
  • Sonnante, G., D'Amore, R., Blanco, E., Pierri, C.L., Palma, M.D., Luo, J., Tucci, M., Martin, C., 2010. Novel hydroxycinnamoyl-coenzyme A quinate transferase genes from artichoke are involved in the synthesis of chlorogenic acid. Plant Physiol. 153, 1224-1238. https://doi.org/10.1104/pp.109.150144.
  • Valinas, M.A., Lanteri, M.L., ten Have, A., Andreu, A.B., 2015. Chlorogenic Acid Biosynthesis appears linked with suberin production in potato tuber (Solanum tuberosum). J. Agric. Food Chem. 63, 4902-4913. https://doi.org/10.1021/jf505777p.
  • Vanholme, B., Cesarino, I., Goeminne, G., Kim, H., Marroni, F., Van Acker, R., Vanholme, R., Morreel, K., Ivens, B., Pinosio, S., Morgante, M., Ralph, J., Bastien, C., Boerjan, W., 2013a. Breeding with rare defective alleles (BRDA): A natural Populus nigra HCT mutant with modified lignin as a case study. New Phytol. 198, 765-776. https://doi. org/10.1111/nph.12179.
  • Vanholme, R., Cesarino, I., Rataj, K., Xiao, Y., Sundin, L., Goeminne, G., Kim, H., Cross, J., Morreel, K., Araujo, P., Welsh, L., Haustraete, J., McClellan, C., Vanholme, B., Ralph, J., Simpson, G.G., Halpin, C., Boerjan, W., 2013b. Caffeoyl Shikimate Esterase (CSE) is an enzyme in the lignin biosynthetic pathway in Arabidopsis. Science 341, 1103-1106. https://doi.org/10.1126/science.1241602.
  • Vanholme, R., De Meester, B., Ralph, J., Boerjan, W., 2019. Lignin biosynthesis and its integration into metabolism. Curr. Opin. Biotechnol., Food Biotechnology • Plant Biotechnology 56, 230-239. https://doi.org/10.1016/j.copbio.2019.02.018.
  • Vanholme, R., Storme, V., Vanholme, B., Sundin, L., Christensen, J.H., Goeminne, G., Halpin, C., Rohde, A., Morreel, K., Boerjan, W., 2012. A systems biology view of responses to lignin biosynthesis perturbations in Arabidopsis. Plant Cell 24, 3506-3529. https://doi.org/10.1105/tpc.112.102574.