Abstract
The diversity of secondary compounds in the plant kingdom is huge. About 200,000 compounds are known, which are grouped into amines, non-protein amino acids, peptides, alkaloids, glucosinolates, cyanogenic glucosides, organic acids, terpenoids, quinones, polyacetylenes, and phenolics. The group of phenolic compounds consists of polyphenols, oligophenols and monophenols or simple phenolic compounds such as benzoic and cinnamic acids and their hydroxylated derivatives. Among the thousands of compounds present in ecological interactions, simple phenolic acids are the most abundant in soils, and many are described as allelochemicals. Given the physiological and biochemical importance of these compounds, we review their biosynthesis and metabolic actions in plants.
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References
Abrahim D, Takahashi L, Kelmer-Bracht AM, Ishii-Iwamoto EL (2003) Effects of phenolic acids and monoterpenes on the mitochondrial respiration of soybean hypocotyl axes. Allelopath J 11:21–30
Ahmed MA, El-Mawla A, Beerhues L (2002) Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum. Planta 214:727–733. https://doi.org/10.1007/s004250100657
Alber A, Ehlting J (2012) Cytochrome P450s in lignin biosynthesis. In: Jouanin L, Lapierre C (eds) Lignins: biosynthesis, biodegradation and bioengineering. Elsevier, London, pp 113–143
Alsaadawi IS, Al-Hadithy SM, Arif MB (1986) Effects of three phenolic acids on chlorophyll content and ions uptake in cowpea seedlings. J Chem Ecol 12:221–227. https://doi.org/10.1007/BF01045605
Anjum SA, Ehsanullah XL et al (2013) Exogenous benzoic acid (BZA) treatment can induce drought tolerance in soybean plants by improving gas-exchange and chlorophyll contents. Aust J Crop Sci 7:555–560
Antoniw JF, White RF (1980) The effects of aspirin and polyacrylic acid on soluble leaf proteins and resistance to virus infection in five cultivars of tobacco. J Phytopathol 98:331–341. https://doi.org/10.1111/j.1439-0434.1980.tb03748.x
Araniti F, Costas-Gil A, Cabeiras-Freijanes L et al (2018) Rosmarinic acid induces programmed cell death in Arabidopsis seedlings through reactive oxygen species and mitochondrial dysfunction. PLoS ONE 13:1–26. https://doi.org/10.1371/journal.pone.0208802
Asada K (2006) Production and scavenging of reactive oxygen species in chloroplasts and their functions. Plant Physiol 141:391–396. https://doi.org/10.1104/pp.106.082040
Bahrami SN, Zakizadeh H, Hamidoghli Y, Ghasemnezhad M (2013) Salicylic acid retards petal senescence in cut lisianthus (Eustoma grandiflorum 'Miarichi Grand White') flowers. Hortic Environ Biotechnol 54:519–523. https://doi.org/10.1007/s13580-013-1058-y
Baker JE, Lieberman M, Anderson JD (1978) Inhibition of ethylene production in fruit slices by a rhizobitoxine analog and free radical scavengers. Plant Physiol 61:886–888. https://doi.org/10.1104/pp.61.6.886
Bandurski RS, Cohen JD, Slovin J, Reinecke DM (1995) Auxin biosynthesis and metabolism. In: Davies PJ (ed) Plant hormones—physiology, biochemistry and molecular biology. Springer, New York, pp 39–65
Barkosky RR, Einhellig FA (2003) Allelopathic interference of plant-water relationships by p-hydroxybenzoic acid. Bot Bull Acad Sin 44:53–58
Barkosky RR, Einhellig FA, Butler JL (2000) Caffeic acid-induced changes in plant-water relationships and photosynthesis in leafy spurge Euphorbia esula. J Chem Ecol 26:2095–2109. https://doi.org/10.1023/A:1005564315131
Barros J, Escamilla-Trevino L, Song L et al (2019) 4-Coumarate 3-hydroxylase in the lignin biosynthesis pathway is a cytosolic ascorbate peroxidase. Nat Commun 10:1–11. https://doi.org/10.1038/s41467-019-10082-7
Barros J, Serrani-Yarce JC, Chen F et al (2016) Role of bifunctional ammonia-lyase in grass cell wall biosynthesis. Nat Plants 2:1–9. https://doi.org/10.1038/NPLANTS.2016.50
Bartsch M, Bednarek P, Vivancos PD et al (2010) Accumulation of isochorismate-derived 2,3-dihydroxybenzoic 3-O-β-D-xyloside in Arabidopsis resistance to pathogens and ageing of leaves. J Biol Chem 285:25654–25665. https://doi.org/10.1074/jbc.M109.092569
Baziramakenga R, Leroux GD, Simard RR (1995) Effects of benzoic and cinnamic acids on membrane permeability of soybean roots. J Chem Ecol 21:1271–1285. https://doi.org/10.1007/BF02027561
Bellés JM, Garro R, Fayos J et al (1999) Gentisic acid as a pathogen-inducible signal, additional to salicylic acid for activation of plant defenses in tomato. Mol Plant Microbe Interact 12:227–235. https://doi.org/10.1094/MPMI.1999.12.3.227
Bevilaqua JM, Finger-Teixeira A, Marchiosi R et al (2019) Exogenous application of rosmarinic acid improves saccharification without affecting growth and lignification of maize. Plant Physiol Biochem 142:275–282. https://doi.org/10.1016/j.plaphy.2019.07.015
Bhattacharya S, Kumar P (2012) An in silico approach to structural elucidation of 3-deoxy-d-arabino-heptulosonate 7-phosphate synthase from Arabidopsis thaliana: hints for herbicide design. Phytochemistry 73:7–14. https://doi.org/10.1016/j.phytochem.2011.09.005
Bischoff M, Schaller A, Bieri F et al (2001) Molecular characterization of tomato 3-dehydroquinate dehydratase-shikimate: NADP oxidoreductase. Plant Physiol 125:1891–1900. https://doi.org/10.1104/pp.125.4.1891
Blum U (2004) Fate of phenolic allelochemicals in soils—the role of soil and rhizosphere microorganisms. In: Macías FA, Galindo JCG, Molinillo JMG, Cutler HG (eds) Allelopathy: Chemistry and mode of action of allelochemicals. CRC Press, Boca Raton
Boerjan W, Ralph J, Baucher M (2003) Lignin biosynthesis. Annu Rev Plant Biol 54:519–546. https://doi.org/10.1146/annurev.arplant.54.031902.134938
Bolouri-Moghaddam MR, Le Roy K, Xiang L et al (2010) Sugar signaling and antioxidant network connections in plant cells. FEBS J 277:2022–2037. https://doi.org/10.1111/j.1742-4658.2010.07633.x
Bubna GA, Lima RB, Zanardo DYL et al (2011) Exogenous caffeic acid inhibits the growth and enhances the lignification of the roots of soybean (Glycine max). J Plant Physiol 168:1627–1633. https://doi.org/10.1016/j.jplph.2011.03.005
Budi Muljono RA, Scheffer JJC, Verpoorte R (2002) Isochorismate is an intermediate in 2,3-dihydroxybenzoic acid biosynthesis in Catharanthus roseus cell cultures. Plant Physiol Biochem 40:231–234. https://doi.org/10.1016/S0981-9428(02)01369-4
Castañeda-Ovando A, Pacheco-Hernández MDL, Páez-Hernández ME et al (2009) Chemical studies of anthocyanins: a review. Food Chem 113:859–871. https://doi.org/10.1016/j.foodchem.2008.09.001
Catinot J, Buchala A, Abou-Mansour E, Métraux JP (2008) Salicylic acid production in response to biotic and abiotic stress depends on isochorismate in Nicotiana benthamiana. FEBS Lett 582:473–478. https://doi.org/10.1016/j.febslet.2007.12.039
Cesarino I, Simões MS, dos Santos BM et al (2016) Building the wall: recent advances in understanding lignin metabolism in grasses. Acta Physiol Plant 38:269. https://doi.org/10.1007/s11738-016-2293-5
Chandran D, Rickert J, Huang Y et al (2014) Atypical E2F transcriptional repressor DEL1 acts at the intersection of plant growth and immunity by controlling the hormone salicylic acid. Cell Host Microbe 15:506–513. https://doi.org/10.1016/j.chom.2014.03.007
Chandrasekara A (2019) Phenolic acids. Encycl Food Chem. https://doi.org/10.1016/B978-0-08-100596-5.22395-0
Chee MJY, Lycett GW, Khoo TJ, Chin CF (2017) Bioengineering of the plant culture of Capsicum frutescens with vanillin synthase gene for the production of vanillin. Mol Biotechnol 59:1–8. https://doi.org/10.1007/s12033-016-9986-2
Chen Z, Zheng Z, Huang J et al (2009) Biosynthesis of salicylic acid in plants. Plant Signal Behav 4:493–496. https://doi.org/10.4161/psb.4.6.8392
Chi WC, Chen YA, Hsiung YC et al (2013) Autotoxicity mechanism of Oryza sativa: Transcriptome response in rice roots exposed to ferulic acid. BMC Genomics 14:351. https://doi.org/10.1186/1471-2164-14-351
Chipley JR (2005) Sodium benzoate and benzoic acid. In: Davidson PM, Sofos JN, Branen AL (eds) Antimicrobials in food, 3rd edn. Taylor & Francis, Boca Raton, pp 11–48
Chong J, Pierrel MA, Atanassova R et al (2001) Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors. Plant Physiol 125:318–328. https://doi.org/10.1104/pp.125.1.318
Coggins JR, Abell C, Evans LB et al (2003) Experiences with the shikimate-pathway enzymes as targets for rational drug design. Biochem Soc Trans 31:548–552. https://doi.org/10.1042/bst0310548
Coracini JD, de Azevedo WF (2014) Shikimate kinase, a protein target for drug design. Curr Med Chem 21:592–604. https://doi.org/10.2174/09298673113206660299
Couée I, Sulmon C, Gouesbet G, El Amrani A (2006) Involvement of soluble sugars in reactive oxygen species balance and responses to oxidative stress in plants. J Exp Bot 57:449–459. https://doi.org/10.1093/jxb/erj027
Dai AH, Nie YX, Yu B et al (2012) Cinnamic acid pretreatment enhances heat tolerance of cucumber leaves through modulating antioxidant enzyme activity. Environ Exp Bot 79:1–10. https://doi.org/10.1016/j.envexpbot.2012.01.003
Dalton BR (1999) The occurrence and behavior of plant phenolic acids in soil environmental and their potential involvement in allelochemical interference interaction: methodological limitations in establishing conclusive proof of allelopathy. In: Inderjit M, Dakshini KMM, Foy CL (eds) Principles and practices in plant ecology: allelochemical interactions. CRC Press, Boca Raton, pp 54–57
De Boer JG, Dicke M (2004) Prey searching behavior of the predatory mite Phytoseiulus persimilis: the role of methyl salicylate. J Chem Ecol 30(11):255–271. https://doi.org/10.1023/b:joec.0000017976.60630.8c
de Klerk GJ, Guan H, Huisman P, Marinova S (2011) Effects of phenolic compounds on adventitious root formation and oxidative decarboxylation of applied indoleacetic acid in Malus ‘Jork 9’. Plant Growth Regul 63:175–185. https://doi.org/10.1007/s10725-010-9555-9
de Marcos LC, van Roermund CWT, Postis VLG et al (2013) Intrinsic acyl-CoA thioesterase activity of a peroxisomal ATP binding cassette transporter is required for transport and metabolism of fatty acids. Proc Natl Acad Sci 110:1279–1284. https://doi.org/10.1073/pnas.1218034110
de Oliveira DM, Finger-Teixeira A, Rodrigues Mota T et al (2015) Ferulic acid: a key component in grass lignocellulose recalcitrance to hydrolysis. Plant Biotechnol J 13:1224–1232. https://doi.org/10.1111/pbi.12292
de Oliveira DM, Finger Teixeira A, de Freitas DL et al (2017) Phenolic compounds in plants: Implications for bioenergy. In: Buckeridge S, de Souza AP (eds) Advances of basic science for second generation bioethanol from sugarcane. Springer, Berlin, pp 39–52
de Paiva LB, Goldbeck R, dos Santos WD, Squina FM (2013) Ferulic acid and derivatives: molecules with potential application in the pharmaceutical field. Braz J Pharm Sci 49:395–411. https://doi.org/10.1590/S1984-82502013000300002
DeClue MS, Baldridge KK, Künzler DE et al (2005) Isochorismate pyruvate lyase: a pericyclic reaction mechanism? J Am Chem Soc 127:15002–15003. https://doi.org/10.1021/ja055871t
Dedonder A, Van Sumere CF (1971) The effect of phenolics and related compounds on the growth and the respiration of Chlorella vulgaris. Z Pflanzenphysiol 65:70–80
Delaney TP, Uknes S, Vernooij B et al (1994) A central role of salicylic acid in plant disease resistance. Science 266(5188):1247–1250. https://doi.org/10.1126/science.266.5188.1247
Demos EK, Woolwine M, Wilson RH, McMillan C (1975) The effects of ten phenolic compounds on hypocotyl growth and mitochondrial metabolism of mung bean. Am J Bot 62:97–102. https://doi.org/10.2307/2442083
Dempsey DA, Vlot AC, Wildermuth MC, Klessig DF (2011) Salicylic acid biosynthesis and metabolism. Arabidopsis Book 9:e0156. https://doi.org/10.1199/tab.0156
Devi RS, Prasad MNV (1996) Ferulic acid mediated changes in oxidative enzymes of maize seedlings: implications in growth. Biol Plant 38:387–395. https://doi.org/10.1007/BF02896668
Dieryckx C, Gaudin V, Dupuy JW et al (2015) Beyond plant defense: insights on the potential of salicylic and methylsalicylic acid to contain growth of the phytopathogen Botrytis cinerea. Front Plant Sci 6:959. https://doi.org/10.3389/fpls.2015.00859
Ding J, Sun Y, Xiao CL et al (2007a) Physiological basis of different allelopathic reactions of cucumber and figleaf gourd plants to cinnamic acid. J Exp Bot 58:3765–3773. https://doi.org/10.1093/jxb/erm227
Ding L, Hofius D, Hajirezaei MR et al (2007b) Functional analysis of the essential bifunctional tobacco enzyme 3-dehydroquinate dehydratase/shikimate dehydrogenase in transgenic tobacco plants. J Exp Bot 58:2053–2067. https://doi.org/10.1093/jxb/erm059
Djordjevic M, Rolfe B (1988) Recognition process in the Rhizobium trifolii-white clover symbiosis. In: Bothe H, Brujin F, Newton F (eds) Nitrogen fixation: hundred years after. Springer, Stuttgart, pp 431–436
Doornbos RF, Geraats BPJ, Kuramae EE et al (2011) Effects of jasmonic acid, ethylene, and salicylic acid signaling on the rhizosphere bacterial community of Arabidopsis thaliana. Mol Plant Microbe Interact 24:395–407. https://doi.org/10.1094/MPMI-05-10-0115
dos Santos W, Ferrarese MLL, Ferrarese-Filho O (2008a) Ferulic acid: an allelochemical troublemaker. Funct Plant Sci Biotechnol 2:47–55
dos Santos WD, Ferrarese MDLL, Finger A et al (2004) Lignification and related enzymes in Glycine max root growth-inhibition by ferulic acid. J Chem Ecol 30:1203–1212. https://doi.org/10.1023/B:JOEC.0000030272.83794.f0
dos Santos WD, Ferrarese MLL, Nakamura CV et al (2008b) Soybean (Glycine max) root lignification induced by ferulic acid. The possible mode of action. J Chem Ecol 34:1230–1241. https://doi.org/10.1007/s10886-008-9522-3
dos Santos WD, Marchiosi R, Vilar FCM et al (2014) Polyvalent lignin: recent approaches in determination and applications. In: Lu F (ed) Lignin: structural analysis, applications in biomaterials and ecological significance. Nova Science, New York, pp 1–25
Duke SO (1985) Effects of herbicides on nonphotosynthetic biosynthetic processes. In: Duke SO (ed) Weed physiology, 1st edn. CRC Press, Boca Raton, pp 91–113
Durrant WE, Dong X (2004) Systemic acquired resistance. Annu Rev Phytopathol 42:185–209. https://doi.org/10.1146/annurev.phyto.42.040803.140421
Effmert U, Saschenbrecker S, Ross J et al (2005) Floral benzenoid carboxyl methyltransferases: from in vitro to in planta function. Phytochemistry 66:1211–1230. https://doi.org/10.1016/j.phytochem.2005.03.031
Einhellig FA (2004) Mode of allelochemical action of phenolic compounds. In: Macías FA, Galindo JCG, Molinillo JMG, Cutler HG (eds) Allelopathy—chemistry and mode of action allelochemicals. CRC Press, New York, pp 217–233
El-Basyouni SZ, Chen D, Ibrahim RK et al (1964) The biosynthesis of hydroxybenzoic acids in higher plants. Phytochemistry 3:485–492. https://doi.org/10.1016/S0031-9422(00)88025-5
El-Tayeb MA (2005) Response of barley grains to the interactive effect of salinity and salicylic acid. Plant Growth Regul 45:215–224. https://doi.org/10.1007/s10725-005-4928-1
Esmaeili M, Heidarzade A, Pirdashti H (2012) Inhibitory activity of pure allelochemicals on Barnyardgrass (Echinochloa crus-galli L.) seed and seedling parameters. Int J Agric Crop Sci 4(6):274–279
Faraji M, Fonseca LL, Escamilla-Treviño L et al (2018) Mathematical models of lignin biosynthesis. Biotechnol Biofuels 11:1–17. https://doi.org/10.1186/s13068-018-1028-9
Fariduddin Q, Hayat S, Ahmad A (2003) Salicylic acid influences net photosynthetic rate, carboxylation efficiency, nitrate reductase activity, and seed yield in Brassica juncea. Photosynthetica 41:281–284. https://doi.org/10.1023/B:PHOT.0000011962.05991.6c
Ferrarese MLL, Rodrigues JD, Ferrarese-Filho O (2000) Phenylalanine ammonia-lyase activity in soybean roots extract measured by reverse-phase high performance liquid chromatography. Plant Biol 2:152–153. https://doi.org/10.1055/s-2000-9162
Forouhar F, Yang Y, Kumar D et al (2005) Structural and biochemical studies identify tobacco SABP2 as a methyl salicylate esterase and implicate it in plant innate immunity. Proc Natl Acad Sci 102:1773–1778. https://doi.org/10.1073/pnas.0409227102
Funk C, Brodelius P (1990a) Phenylpropanoid metabolism in suspension cultures of Vanilla planifolia Andr. II Effects of precursor feeding and metabolic inhibitors. Plant Physiol 94:95–101. https://doi.org/10.1016/0031-9422(90)80030-K
Funk C, Brodelius PE (1990b) Phenylpropanoid metabolism in suspension cultures of Vanilla planifolia andr.: III. Conversion of 4-methoxycinnamic acids into 4-hydroxybenzoic acids. Plant Physiol 94:102–108. https://doi.org/10.1104/pp.94.1.102
Gaffney T, Friedrich L, Vernooij B et al (1993) Requirement of salicylic acid for the induction of systemic acquired resistance. Science 261(5122):754–756. https://doi.org/10.1126/science.261.5122.754
Gallage NJ, Hansen EH, Kannangara R et al (2014) Vanillin formation from ferulic acid in Vanilla planifolia is catalysed by a single enzyme. Nat Commun 5:4037. https://doi.org/10.1038/ncomms5037
Gallage NJ, Jørgensen K, Janfelt C et al (2018) The intracellular localization of the vanillin biosynthetic machinery in pods of Vanilla planifolia. Plant Cell Physiol 59:304–318. https://doi.org/10.1093/pcp/pcx185
Gallage NJ, Møller BL (2015) Vanillin-bioconversion and bioengineering of the most popular plant flavor and its de novo biosynthesis in the vanilla orchid. Mol Plant 8:40–57. https://doi.org/10.1016/j.molp.2014.11.008
Gasson MJ, Kitamura Y, McLauchlan WR et al (1998) Metabolism of ferulic acid to vanillin. J Biol Chem 273:4163–4170. https://doi.org/10.1074/jbc.273.7.4163
Gebhardt K (1982) Activation of indole-3 acetic acid oxidase from horseradish and Prunus by phenols and H2O2. Plant Growth Regul 1:73–84. https://doi.org/10.1007/BF00024500
Ghareib HRA, Abdelhamed MS, Ibrahim OH (2010) Antioxidative effects of the acetone fraction and vanillic acid from Chenopodium murale on tomato plants. Weed Biol Manag 10:64–72. https://doi.org/10.1111/j.1445-6664.2010.00368.x
Ghosh S, Chisti Y, Banerjee UC (2012) Production of shikimic acid. Biotechnol Adv 30:1425–1431. https://doi.org/10.1016/j.biotechadv.2012.03.001
Gosch C, Halbwirth H, Stich K (2010) Phloridzin: biosynthesis, distribution and physiological relevance in plants. Phytochemistry 71:838–843. https://doi.org/10.1016/j.phytochem.2010.03.003
Grabber JH, Schatz PF, Kim H et al (2010) Identifying new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability. BMC Plant Biol 10:114. https://doi.org/10.1186/1471-2229-10-114
Greeland DJ (1971) Interactions between humic and fulvic acids and clays. Soil Sci 111:34–41
Guo J, Carrington Y, Alber A, Ehlting J (2014) Molecular characterization of quinate and shikimate metabolism in Populus trichocarpa. J Biol Chem 289:23846–23858. https://doi.org/10.1074/jbc.M114.558536
Halestrap AP (2009) What is the mitochondrial permeability transition pore? J Mol Cell Cardiol 46:821–831. https://doi.org/10.1016/j.yjmcc.2009.02.021
Hamada K, Tsutsumi Y, Nishida T (2003) Treatment of poplar callus with ferulic and sinapic acids II: effects on related monolignol biosynthetic enzyme activities. J Wood Sci 49:366–370. https://doi.org/10.1007/s10086-002-0475-9
Hammerbacher A, Coutinho TA, Gershenzon J (2019) Roles of plant volatiles in defense against microbial pathogens and microbial exploitation of volatiles. Plant Cell Environ. https://doi.org/10.1111/pce.13602
Hatayama T, Takeno K (2003) The metabolic pathway of salicylic acid rather than of chlorogenic acid is involved in the stress-induced flowering of Pharbitis nil. J Plant Physiol 160:461–467. https://doi.org/10.1078/0176-1617-01041
Hättenschwiler S, Vitousek PM (2000) The role of polyphenols in terrestrial ecosystem nutrient cycling. Tree 15:238–243. https://doi.org/10.1016/S0169-5347(00)01861-9
Havkin-Frenkel D, Podstolski A (2007) Vanillin production. USA patent, US2007/0231864 A1
Havkin-Frenkel D, Podstolski D, Dixon RA (2003) Vanillin biosynthetic pathway enzyme from Vanilla planifolia. USA patent, US2003/0070188 A1
Havkin-Frenkel D, Zylstra G, Frenkel C, Belanger F (2006) Production of vanillin in microbial cells. US patent, US20060172402 A1
Hayat Q, Hayat S, Irfan M, Ahmad A (2010) Effect of exogenous salicylic acid under changing environment: a review. Environ Exp Bot 68:14–25. https://doi.org/10.1016/j.envexpbot.2009.08.005
Herrmann KM (1995) The shikimate pathway: early steps in the biosynthesis of aromatic compounds. Plant Cell 7:907–919. https://doi.org/10.2307/3870046
Herrmann KM, Weaver LM (1999) The shikimate pathway. Annu Rev Plant Physiol Plant Mol Biol 50:473–503. https://doi.org/10.1146/annurev.arplant.50.1.473
Holopainen JK, Blande JD (2012) Molecular plant volatile communication. Adv Exp Med Biol 739:17–31. https://doi.org/10.1007/978-1-4614-1704-0_2
Hua J, Meyerowitz EM (1998) Ethylene responses are negatively regulated by a receptor gene family in Arabidopsis thaliana. Cell 94:261–271. https://doi.org/10.1016/S0092-8674(00)81425-7
Huang X, Bie Z (2010) Cinnamic acid-inhibited ribulose-1,5-bisphosphate carboxylase activity is mediated through decreased spermine and changes in the ratio of polyamines in cowpea. J Plant Physiol 167:47–53. https://doi.org/10.1016/j.jplph.2009.07.002
Huang X, Zhu G, Liu Q et al (2018) Modulation of plant salicylic acid-associated immune responses via glycosylation of dihydroxybenzoic acids. Plant Physiol 176:3103–3119. https://doi.org/10.1104/pp.17.01530
Huang YF, Chen CT, Kao CH (1993) Salicylic acid inhibits the biosynthesis of ethylene in detached rice leaves. Plant Growth Regul 12:79–82. https://doi.org/10.1007/BF00144586
Hunt L, Holdsworth MJ, Gray JE (2007) Nicotinamidase activity is important for germination. Plant J 51:341–351. https://doi.org/10.1111/j.1365-313X.2007.03151.x
Hussain MI, González L, Reigosa MJ (2010) Phytotoxic effects of allelochemicals and herbicides on photosynthesis, growth and carbon isotope discrimination in Lactuca sativa. Allelopath J 26:157–174
Hussain MI, Reigosa MJ (2011) Allelochemical stress inhibits growth, leaf water relations, PSII photochemistry, non-photochemical fluorescence quenching, and heat energy dissipation in three C3 perennial species. J Exp Bot 62(13):4533–4545. https://doi.org/10.1093/jxb/err161
Hussain MS, Fareed S, Ansari S et al (2012) Current approaches toward production of secondary plant metabolites. J Pharm Bioallied Sci 4:10–20. https://doi.org/10.4103/0975-7406.92725
Igiehon NO, Babalola OO (2018) Below-ground-above-ground plant-microbial interactions: focusing on soybean, rhizobacteria and mycorrhizal fungi. Open Microbiol J 12:261–279. https://doi.org/10.2174/1874285801812010261
Inderjit M, Bhowmik PC (2004) Sorption of benzoic acid onto soil colloids and its implications for allelopathy studies. Biol Fertil Soils 40:345–348. https://doi.org/10.1007/s00374-004-0785-8
Ishihara T, Sekine KT, Hase S et al (2008) Overexpression of the Arabidopsis thaliana EDS5 gene enhances resistance to viruses. Plant Biol 10:451–461. https://doi.org/10.1111/j.1438-8677.2008.00050.x
Ishii-Iwamoto EL, Abrahim D, Sert MA et al (2006) Mitochondria as a site of allelochemical action. In: Reigosa MJ, Pedrol N, González L (eds) Allelopathy: a physiological process with ecological implications. Springer, Dordrecht, pp 267–284
James DG, Price TS (2004) Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops. J Chem Ecol 30:1613–1628
Jarvis AP, Schaaf O, Oldham NJ (2000) 3-Hydroxy-3-phenylpropanoic acid is an intermediate in the biosynthesis of benzoic acid and salicylic acid but benzaldehyde is not. Planta 212:119–126. https://doi.org/10.1007/s004250000377
Jazayeri O, Aghajanzadeh TA, Gildeh BS (2007) Study of growth factors, α-amylase and peroxidase activity in various cultivars of rice (Oryza sativa L.) under vanillic acid stress. Pakistan J Biol Sci 10:1673–1678
Ji Y, Liu J, Xing D (2016) Low concentrations of salicylic acid delay methyl jasmonate-induced leaf senescence by up-regulating nitric oxide synthase activity. J Exp Bot 67:5233–5245. https://doi.org/10.1093/jxb/erw280
Kennedy DO, Wightman EEL (2011) Herbal extracts and phytochemicals: plant secondary metabolites and the enhancement of human brain function. Adv Nutr 2:32–50. https://doi.org/10.3945/an.110.000117.32
Khalil S, Pawelek PD (2011) Enzymatic adenylation of 2,3-dihydroxybenzoate is enhanced by a protein-protein interaction between Escherichia coli 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase (EntA) and 2,3-dihydroxybenzoate-AMP ligase (EntE). Biochemistry 50:533–545. https://doi.org/10.1021/bi101558v
Khan W, Prithiviraj B, Smith DL (2003) Photosynthetic responses of corn and soybean to foliar application of salicylates. J Plant Physiol 160:485–492. https://doi.org/10.1078/0176-1617-00865
Kitzing K, Auweter S, Amrhein N, Macheroux P (2004) Mechanism of chorismate synthase: role of the two invariant histidine residues in the active site. J Biol Chem 279:9451–9461. https://doi.org/10.1074/jbc.M312471200
Kluge RA, Picoli AA, del Aguila JS (2010) Respiratory rate and ethylene production of whole and minimally processed beet roots submitted to ethylene and bioregulators treatments. Hortic Bras 28:54–57
Kobayashi K (2015) Plant methyl salicylate induces defense responses in the rhizobacterium Bacillus subtilis. Environ Microbiol 17:1365–1376. https://doi.org/10.1111/1462-2920.12613
Kundu A (2017) Vanillin biosynthetic pathways in plants. Planta 245:1069–1078. https://doi.org/10.1007/s00425-017-2684-x
Kutchan TM, Gershenzon J, Moller BL, Gang DR (2015) Natural products. In: Buchanan BB, Gruissem W, Jones RL (eds) Biochemistry & molecular biology of plants. Wiley, New York, pp 1132–1205
Lam PY, Liu H, Lo C (2015) Completion of tricin biosynthesis pathway in rice: cytochrome P450 75B4 is a unique chrysoeriol 5′-hydroxylase. Plant Physiol 168:1527–1536. https://doi.org/10.1104/pp.15.00566
Lan W, Lu F, Regner M et al (2015) Tricin, a flavonoid monomer in monocot lignification. Plant Physiol 167:1284–1295. https://doi.org/10.1104/pp.114.253757
Lebeis SL, Paredes SH, Lundberg DS et al (2015) Salicylic acid modulates colonization of the root microbiome by specific bacterial taxa. Science 349(6250):860–864. https://doi.org/10.5061/dryad.238b2
Lee RB (1977) Effects of organic acids on the loss of ions from barley roots. J Exp Bot 28:578–587. https://doi.org/10.1093/jxb/28.3.578
León J, Shulaev V, Yalpani N et al (1995) Benzoic acid 2-hydroxylase, a soluble oxygenase from tobacco, catalyzes salicylic acid biosynthesis. Proc Natl Acad Sci 92:10413–10417. https://doi.org/10.1073/pnas.92.22.10413
Leslie CA, Romani RJ (1988) Inhibition of ethylene biosynthesis by salicylic acid. Plant Physiol 88:833–837. https://doi.org/10.1104/pp.88.3.833
Li HH, Inoue M, Nishimura H et al (1993) Interactions of trans-cinnamic acid, its related phenolic allelochemicals, and abscisic acid in seedling growth and seed germination of lettuce. J Chem Ecol 19:1775–1787. https://doi.org/10.1007/BF00982307
Li ZH, Wang Q, Ruan X et al (2010) Phenolics and plant allelopathy. Molecules 15:8933–8952. https://doi.org/10.3390/molecules15128933
Lima RB, Salvador VH, dos Santos WD et al (2013) Enhanced lignin monomer production caused by cinnamic acid and its hydroxylated derivatives inhibits soybean root growth. PLoS ONE 8:1–8. https://doi.org/10.1371/journal.pone.0080542
Lopez-Vergara HI, Jackson KM, Meshesha LZ, Metrik J (2019) Dysregulation as a correlate of cannabis use and problem use. Addict Behav 95:138–144. https://doi.org/10.1016/j.addbeh.2019.03.010
Lu XF, Zhang H, Lyu SS et al (2018) Effects of exogenous phenolic acids on photosystem functions and photosynthetic electron transport rate in strawberry leaves. Photosynthetica 56:616–622. https://doi.org/10.1007/s11099-017-0702-7
Lugtenberg B, Kamilova F (2009) Plant-growth-promoting rhizobacteria. Annu Rev Microbiol 63:541–556. https://doi.org/10.1016/B978-0-12-374984-0.01169-4
Macheroux P, Schmid J, Amrhein N, Schaller A (1999) A unique reaction in a common pathway: mechanism and function of chorismate synthase in the shikimate pathway. Planta 207:325–334. https://doi.org/10.1007/s004250050489
Macías FA, Mejías FJR, Molinillo JMG (2019) Recent advances in allelopathy for weed control: from knowledge to applications. Pest Manag Sci 75:2413–2436
Maeda H, Dudareva N (2012) The shikimate pathway and aromatic amino acid biosynthesis in plants. Annu Rev Plant Biol 63:73–105. https://doi.org/10.1146/annurev-arplant-042811-105439
Makovec P, Sindelár L (1984) The effect of phenolic compounds on the activity of respiratory chain enzymes and on respiration and phosphorylation activities of potato tuber mitochondria. Biol Plant 26:415–422. https://doi.org/10.1007/BF02909590
Mallinger RE, Hogg DB, Gratton C (2011) Methyl salicylate attracts natural enemies and reduces populations of soybean aphids (Hemiptera: Aphididae) in soybean agroecosystems. J Econ Entomol 104:115–124. https://doi.org/10.1603/EC10253
Mandal S, Mandal M, Das A et al (2009) Stimulation of indoleacetic acid production in a Rhizobium isolate of Vigna mungo by root nodule phenolic acids. Arch Microbiol 191:389–393. https://doi.org/10.1007/s00203-008-0455-6
Mandal SM, Chakraborty D, Dey S (2010) Phenolic acids act as signaling molecules in plant-microbe symbioses. Plant Signal Behav 5:359–368. https://doi.org/10.4161/psb.5.4.10871
Martí S, Andrés J, Moliner V et al (2009) Mechanism and plasticity of isochorismate pyruvate lyase: a computational study. J Am Chem Soc 131:16156–16161. https://doi.org/10.1021/ja905271g
Martínez C, Pons E, Prats G, León J (2004) Salicylic acid regulates flowering time and links defense responses and reproductive development. Plant J 37:209–217. https://doi.org/10.1046/j.1365-313X.2003.01954.x
Martini X, Pelz-Stelinski KS, Stelinski LL (2014) Plant pathogen-induced volatiles attract parasitoids to increase parasitism of an insect vector. Front Ecol Evol 2:1–8. https://doi.org/10.3389/fevo.2014.00008
Mittelstädt G, Negron L, Schofield LR et al (2013) Biochemical and structural characterisation of dehydroquinate synthase from the New Zealand kiwifruit Actinidia chinensis. Arch Biochem Biophys 537:185–191. https://doi.org/10.1016/j.abb.2013.07.022
Moreland DE, Novitzky WP (1987) Effects of phenolic acids, coumarins, and flavonoids on isolated chloroplasts and mitochondria. In: Waller GR (ed) Allelochemicals: role in agriculture and forestry. American Chemical Society, Washington, DC, pp 247–261
Mittova V, Tal M, Volokita M, Guy M (2003) Up-regulation of the leaf mitochondrial and peroxisomal antioxidative systems in response to salt-induced oxidative stress in the wild salt-tolerant tomato species Lycopersicon pennellii. Plant Cell Environ 26:845–856. https://doi.org/10.1046/j.1365-3040.2003.01016.x
Moreno PRH, Van Der HR, Verpoorte R (1996) Elicitor-mediated induction of isochorismate synthase and accumulation of 2,3-dihydroxybenzoic acid Catharanthus roseus cell suspension and shoot cultures. Plant Cell Rep 15:516–521
Muir RM, Ibáñez AM, Uratsu SL et al (2011) Mechanism of gallic acid biosynthesis in bacteria (Escherichia coli) and walnut (Juglans regia). Plant Mol Biol 75:555–565. https://doi.org/10.1007/s11103-011-9739-3
Mustafa NR, Kim HK, Choi YH et al (2009) Biosynthesis of salicylic acid in fungus elicited Catharanthus roseus cells. Phytochemistry 70:532–539. https://doi.org/10.1016/j.phytochem.2009.01.009
Mustafa NR, Verpoorte R (2005) Chorismate derived C6C1 compounds in plants. Planta 222:1–5. https://doi.org/10.1007/s00425-005-1554-0
Naczk M, Shahidi F (2006) Phenolics in cereals, fruits and vegetables: occurrence, extraction and analysis. J Pharm Biomed Anal 41:1523–1542. https://doi.org/10.1016/j.jpba.2006.04.002
Nair RB, Bastress KL, Ruegger MO et al (2004) The Arabidopsis thaliana reduced epidermal fluorescence1 gene encodes an aldehyde dehydrogenase involved in ferulic acid and sinapic acid biosynthesis. Plant Cell 16:544–554. https://doi.org/10.1105/tpc.017509
Nawrath C (2002) EDS5, an essential component of salicylic acid-dependent signaling for disease resistance in Arabidopsis, is a member of the MATE transporter family. Plant Cell 14:275–286. https://doi.org/10.1105/tpc.010376
Niggeweg R, Michael AJ, Martin C (2004) Engineering plants with increased levels of the antioxidant chlorogenic acid. Nat Biotechnol 22:746–754. https://doi.org/10.1038/nbt966
Norman C, Howell KA, Millar AH et al (2004) Salicylic acid is an uncoupler and inhibitor of mitochondrial electron transport. Plant Physiol 134:492–501. https://doi.org/10.1104/pp.103.031039
Ogo Y, Ozawa K, Ishimaru T et al (2013) Transgenic rice seed synthesizing diverse flavonoids at high levels: a new platform for flavonoid production with associated health benefits. Plant Biotechnol J 11:734–746. https://doi.org/10.1111/pbi.12064
Oliveira DM, Mota TR, Oliva B et al (2019) Feruloyl esterases: biocatalysts to overcome biomass recalcitrance and for the production of bioactive compounds. Bioresour Technol 278:408–423. https://doi.org/10.1016/j.biortech.2019.01.064
Pak FE, Gropper S, Dai WD et al (2004) Characterization of a multifunctional methyltransferase from the orchid Vanilla planifolia. Plant Cell Rep 22:959–966. https://doi.org/10.1007/s00299-004-0795-x
Park SW, Kaimoyo E, Kumar D et al (2007) Methyl salicylate is a critical mobile signal for plant systemic acquired resistance. Science 318:113–116. https://doi.org/10.1126/science.1147113
Parsons HL, Yip JYH, Vanlerberghe GC (1999) Increased respiratory restriction during phosphate-limited growth in transgenic tobacco cells lacking alternative oxidase. Plant Physiol 121:1309–1320. https://doi.org/10.1104/pp.121.4.1309
Peñuelas J, Ribas-Carbo M, Giles L (1996) Effects of allelochemicals on plant respiration and oxygen isotope fractionation by the alternative oxidase. J Chem Ecol 22:801–805
Petrik DL, Karlen SD, Cass CL et al (2014) p-Coumaroyl-CoA: monolignol transferase (PMT) acts specifically in the lignin biosynthetic pathway in Brachypodium distachyon. Plant J 77:713–726. https://doi.org/10.1111/tpj.12420
Pierpoint WS (1997) The natural history of salicylic acid plant product and mammalian medicine. Interdiscip Sci Rev 22:45–52. https://doi.org/10.1179/030801897789765129
Pieterse CMJ, Zamioudis C, Berendsen RL et al (2014) Induced systemic resistance by beneficial microbes. Annu Rev Phytopathol 52:347–375. https://doi.org/10.1146/annurev-phyto-082712-102340
Podstolski A, Havkin-Frenkel D, Malinowski J et al (2002) Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. Phytochemistry 61:611–620. https://doi.org/10.1016/S0031-9422(02)00285-6
Polidoros AN, Mylona PV, Pasentsis K et al (2005) The maize alternative oxidase 1a (Aox1a) gene is regulated by signals related to oxidative stress. Redox Rep 10:71–78. https://doi.org/10.1179/135100005x21688
Popov VN, Simonian RA, Skulachev VP, Starkov AA (1997) Inhibition of the alternative oxidase stimulates H2O2 production in plant mitochondria. FEBS Lett 415:87–90. https://doi.org/10.1016/S0014-5793(97)01099-5
Poulev A, Heckman JR, Raskin I, Belanger FC (2019) Tricin levels and expression of flavonoid biosynthetic genes in developing grains of purple and brown pericarp rice. PeerJ 7:e6477. https://doi.org/10.7717/peerj.6477
Premoli M, Aria F, Bonini SA et al (2019) Cannabidiol: recent advances and new insights for neuropsychiatric disorders treatment. Life Sci 224:120–127. https://doi.org/10.1016/J.LFS.2019.03.053
Purohit S, Laloraya MM, Bharti S (1991) Effect of phenolic compounds on abscisic acid-induced stomatal movement: structure—activity relationship. Physiol Plant 81:79–82. https://doi.org/10.1111/j.1399-3054.1991.tb01716.x
Qualley AV, Widhalm JR, Adebesin F et al (2012) Completion of the core-oxidative pathway of benzoic acid biosynthesis in plants. Proc Natl Acad Sci 109:16383–16388. https://doi.org/10.1073/pnas.1211001109
Rajput P, Rao PB (2013) Weed management through bio-herbicidal activity of rice straw for mitigating herbicide dependency. Am J Agric Environ Sci 13:1533–1540. https://doi.org/10.5829/idosi.aejaes.2013.13.11.1812
Raskin I, Ehmann A, Melander WR, Meeuse BJD (1987) Salicylic acid: a natural inducer of heat production in Arum lilies. Science 237:1601–1602. https://doi.org/10.1126/science.237.4822.1601
Raskin I, Turner IM, Melander WR (1989) Regulation of heat production in the inflorescences of an Arum lily by endogenous salicylic acid. Proc Natl Acad Sci 86:2214–2218. https://doi.org/10.1073/pnas.86.7.2214
Rasmann S, Turlings TCJ (2016) Root signals that mediate mutualistic interactions in the rhizosphere. Curr Opin Plant Biol 32:62–68. https://doi.org/10.1016/j.pbi.2016.06.017
Saha B, Borovskii G, Panda SK (2016) Alternative oxidase and plant stress tolerance. Plant Signal Behav 11:e1256530. https://doi.org/10.1080/15592324.2016.1256530
Salvador VH, Lima RB, dos Santos WD et al (2013) Cinnamic acid increases lignin production and inhibits soybean root growth. PLoS ONE 8:1–10. https://doi.org/10.1371/journal.pone.0069105
Schmidt CL, Danneel H-J, Schultz G, Buchanan BB (1990) Shikimate kinase from spinach chloroplasts. Plant Physiol 93:758–766
Schönbrunn E, Eschenburg S, Shuttleworth WA et al (2001) Interaction of the herbicide glyphosate with its target enzyme 5-enolpyruvylshikimate 3-phosphate synthase in atomic detail. Proc Natl Acad Sci 98:1376–1380. https://doi.org/10.1073/pnas.98.4.1376
Seneviratne G, Jayasinghearachchi HS (2003) Phenolic acids: possible agents of modifying N2-fixing symbiosis through rhizobial alteration? Plant Soil 252:385–395. https://doi.org/10.1023/A:1024725511783
Sert MA, Ferrarese MLL, Bernadelli YR et al (1997) Effects of ferulic acid on L-malate oxidation in isolated soybean mitochondria. Biol Plant 40:345–350
Sharma P, Jha AB, Dubey RS, Pessarakli M (2012) Reactive oxygen species, oxidative damage, and antioxidative defense mechanism in plants under stressful conditions. J Bot 2012:1–26. https://doi.org/10.1155/2012/217037
Sharma A, Sidhu GPS, Araniti F, Bali AS, Shahzad B, Tripathi DK, Brestic M, Skalicky M, Landi M (2020) The role of salicylic acid in plants exposed to heavy metals. Molecules 25:540–561. https://doi.org/10.3390/molecules25030540
Shin SY, Kim IS, Kim YS et al (2013) Ectopic expression of Brassica rapa L. MDHAR increased tolerance to freezing stress by enhancing antioxidant systems of host plants. S Afr J Bot 88:388–400. https://doi.org/10.1016/j.sajb.2013.08.015
Shitan N (2016) Secondary metabolites in plants: transport and self-tolerance mechanisms. Biosci Biotechnol Biochem 80:1283–1293. https://doi.org/10.1080/09168451.2016.1151344
Singh HP, Kaur S, Batish DR, Kohli RK (2009) Caffeic acid inhibits in vitro rooting in mung bean [Vigna radiata (L.) Wilczek] hypocotyls by inducing oxidative stress. Plant Growth Regul 57:21–30. https://doi.org/10.1007/s10725-008-9314-3
Singh PK, Singh R, Singh S (2013) Cinnamic acid induced changes in reactive oxygen species scavenging enzymes and protein profile in maize (Zea mays L.) plants grown under salt stress. Physiol Mol Biol Plants 19:53–59. https://doi.org/10.1007/s12298-012-0126-6
Singh SA, Christendat D (2006) Structure of Arabidopsis dehydroquinate dehydratase-shikimate dehydrogenase and implications for metabolic channeling in the shikimate pathway. Biochemistry 45:7787–7796. https://doi.org/10.1021/bi060366
Singh SA, Christendat D (2007) The DHQ-dehydroshikimate-SDH-shikimate-NADP(H) complex: insights into metabolite transfer in the shikimate pathway. Cryst Growth Des 7:2153–2160. https://doi.org/10.1021/cg7007107
Smith LM (2019) Salicylic acid, senescence, and heterosis. Plant Physiol 180:3–4. https://doi.org/10.1104/pp.19.00260
Snoeren TAL, Mumm R, Poelman EH et al (2010) The herbivore-induced plant volatile methyl salicylate negatively affects attraction of the parasitoid Diadegma semiclausum. J Chem Ecol 36:479–489. https://doi.org/10.1007/s10886-010-9787-1
Stallings WC, Abdel-Meguid SS, Lim LW et al (1991) Structure and topological symmetry of the glyphosate target 5-enolpyruvylshikimate-3-phosphate synthase: a distinctive protein fold. Proc Natl Acad Sci 88:5046–5050. https://doi.org/10.1073/pnas.88.11.5046
Staswick PE, Su W, Howell SH (1992) Methyl jasmonate inhibition of root growth and induction of a leaf protein are decreased in an Arabidopsis thaliana mutant. Proc Natl Acad Sci 89:6837–6840. https://doi.org/10.1073/pnas.89.15.6837
Stepanycheva EA, Petrova MO, Chermenskaya TD, Shamshev IV (2016) Effect of methyl salicylate on behavioral responses of insects in a forest park. Entomol Rev 96:284–287. https://doi.org/10.1134/S0013873816030052
Stevens J, Senaratna T, Sivasithamparam K (2006) Salicylic acid induces salinity tolerance in tomato (Lycopersicon esculentum cv. Roma): associated changes in gas exchange, water relations and membrane stabilisation. Plant Growth Regul 49:77–83. https://doi.org/10.1007/s10725-006-0019-1
Sun WJ, Nie YX, Gao Y et al (2012) Exogenous cinnamic acid regulates antioxidant enzyme activity and reduces lipid peroxidation in drought-stressed cucumber leaves. Acta Physiol Plant 34:641–655. https://doi.org/10.1007/s11738-011-0865-y
Takeoka TN (1968) Formation of protocatechuic acid from 5-dehydroshikimic acid in the extract of mung bean seedling. Bot Mag Tokyo 81:103–104
Tharayil N, Bhowmik PC, Xing B (2006) Preferential sorption of phenolic phytotoxins to soil: implications for altering the availability of allelochemicals. J Agric Food Chem 54:3033–3040. https://doi.org/10.1021/jf053167q
Tobimatsu Y, Elumalai S, Grabber JH et al (2012) Hydroxycinnamate conjugates as potential monolignol replacements: in vitro lignification and cell wall studies with rosmarinic acid. Chemsuschem 5:676–686. https://doi.org/10.1002/cssc.201100573
Tohge T, Watanabe M, Hoefgen R, Fernie AR (2013) Shikimate and phenylalanine biosynthesis in the green lineage. Front Plant Sci 4:1–13. https://doi.org/10.3389/fpls.2013.00062
Trezzi MM, Vidal RA, Junior AAB et al (2016) Allelopathy: driving mechanisms governing its activity in agriculture. J Plant Interact 11:53–60. https://doi.org/10.1080/17429145.2016.1159342
Tsao R, Deng Z (2004) Separation procedures for naturally occurring antioxidant phytochemicals. J Chromatogr B 812:85–99. https://doi.org/10.1016/j.jchromb.2004.09.028
Tzin V, Galili G (2010a) New insights into the shikimate and aromatic amino acids biosynthesis pathways in plants. Mol Plant 3:956–972. https://doi.org/10.1093/mp/ssq048
Tzin V, Galili G (2010) The biosynthetic pathways for shikimate and aromatic amino acids in Arabidopsis thaliana. In: Torii K (ed) The Arabidopsis book. American Society of Plant Biologists, Rockville, p 8
Umezawa T (2018) Lignin modification in planta for valorization. Phytochem Rev 17:1305–1327. https://doi.org/10.1007/s11101-017-9545-x
van Overbeek J, Blondeau R, Horne V (1951) Trans-cinnamic acid as an anti-auxin. Am J Bot 38:589–595. https://doi.org/10.2307/2437768
Vanholme R, Cesarino I, Rataj K et al (2013) 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, Demedts B, Morrel K et al (2010) Lignin biosynthesis and structure. Plant Physiol 153:895–905. https://doi.org/10.1104/pp.110.155119
Veach AM, Morris R, Yip DZ et al (2019) Rhizosphere microbiomes diverge among Populus trichocarpa plant-host genotypes and chemotypes, but it depends on soil origin. Microbiome 7:1–15. https://doi.org/10.1186/s40168-019-0668-8
Venturi V, Keel C (2016) Signaling in the rhizosphere. Trends Plant Sci 21:187–198. https://doi.org/10.1016/j.tplants.2016.01.005
Verberne MC, Verpoorte R, Bol JF et al (2000) Overproduction of salicylic acid in plants by bacterial transgenes enhances pathogen resistance. Nat Biotechnol 18:779–783. https://doi.org/10.1038/77347
Vernooij B, Friedrichya L, Reist R et al (1994) Salicylic acid is not the translocated signal responsible for inducing systemic acquired resistance but is required in signal transduction. Plant Cell 6:959–965. https://doi.org/10.1105/tpc.6.7.959
Wan YY, Chen SY, Huang YW et al (2014) Caffeic acid pretreatment enhances dehydration tolerance in cucumber seedlings by increasing antioxidant enzyme activity and proline and soluble sugar contents. Sci Hortic 173:54–64. https://doi.org/10.1016/j.scienta.2014.04.033
Wang SP, Lin SC, Li S et al (2016) Potent antiarthritic properties of phloretin in murine collagen-induced arthritis. Evid Based Complem Altern Med 2016:1–9. https://doi.org/10.1155/2016/9831263
Wang XQ, Du GD, Lu XF et al (2019) Characteristics of mitochondrial membrane functions and antioxidant enzyme activities in strawberry roots under exogenous phenolic acid stress. Sci Hortic 248:89–97. https://doi.org/10.1016/j.scienta.2018.12.051
War AR, Paulraj MG, Ahmad T et al (2012) Mechanisms of plant defense against insect herbivores. Plant Signal Behav 7:1306–1320. https://doi.org/10.4161/psb.21663
White RF (1979) Acetylsalicylic acid (aspirin) induces resistance to tobacco mosaic virus in tobacco. Virology 99:410–412. https://doi.org/10.1016/0042-6822(79)90019-9
Whitehead DC (1964) Identification of p-hydroxybenzoic, vanillic, p-coumaric and ferulic acids in soils. Nature 202:417–418
Widhalm JR, Dudareva N (2015) A familiar ring to it: biosynthesis of plant benzoic acids. Mol Plant 8:83–97. https://doi.org/10.1016/j.molp.2014.12.001
Wildermuth MC (2006) Variations on a theme: synthesis and modification of plant benzoic acids. Curr Opin Plant Biol 9:288–296. https://doi.org/10.1016/j.pbi.2006.03.006
Wildermuth MC, Dewdney J, Wu G, Ausubel FM (2001) Isochorismate synthase is required to synthesize salicylic acid for plant defense. Nature 414:562–565. https://doi.org/10.1038/35107108
Wilson PJ, Van Staden SJ (1990) Rhizocaline, rooting co-factors, and the concept of promoters and inhibitors of adventitious rooting—a review. Ann Bot 66:479–490. https://doi.org/10.1093/oxfordjournals.aob.a088051
Wink M (2018) Plant secondary metabolites modulate insect behavior-steps toward addiction? Front Physiol 9:1–9. https://doi.org/10.3389/fphys.2018.00364
Wink M (2015) Modes of action of herbal medicines and plant secondary metabolites. Medicines 2:251–286. https://doi.org/10.3390/medicines2030251
Wink M (2010) Biochemistry, physiology and ecological functions of secondary metabolites. In: Wink M (ed) Biochemistry of plant secondary metabolism, 2nd edn. Blackwell, Hoboken
Withers S, Lu F, Kim H et al (2012) Identification of grass-specific enzyme that acylates monolignols with p-coumarate. J Biol Chem 287:8347–8355. https://doi.org/10.1074/jbc.m111.284497
Yamauchi K, Fukushima K (2004) The regulation from guaiacyl to syringyl lignin in the differentiating xylem of Robinia pseudoacacia. C R Biol 327:791–797. https://doi.org/10.1016/j.crvi.2004.07.012
Yang CM, Chang IF, Lin SJ, Chou CH (2004) Effects of three allelopathic phenolics on chlorophyll accumulation of rice (Oryza sativa) seedlings: II. Stimulation of consumption-orientation. Bot Bull Acad Sin 45:119–125
Yang CM, Lee CN, Chou CH (2002) Effects of three allelopathic phenolics on chlorophyll accumulation of rice (Oryza sativa) seedlings: I. Inhibition of supply-orientation. Bot Bull Acad Sin 43:299–304
Yang H, Barros-rios J, Kourteva G et al (2017) A re-evaluation of the final step of vanillin biosynthesis in the orchid Vanilla planifolia. Phytochemistry 139:33–46. https://doi.org/10.1016/j.phytochem.2017.04.003
Ye SF, Yu JQ, Peng YH et al (2004) Incidence of Fusarium wilt in Cucumis sativus L. is promoted by cinnamic acid, an autotoxin in root exudates. Plant Soil 263:143–150. https://doi.org/10.1023/B:PLSO.0000047721.78555.dc
Yu JQ, Ye SF, Zhang MF, Hu WH (2003) Effects of root exudates and aqueous root extracts of cucumber (Cucumis sativus) and allelochemicals, on photosynthesis and antioxidant enzymes in cucumber. Biochem Syst Ecol 31:129–139. https://doi.org/10.1016/S0305-1978(02)00150-3
Zabalza A, Orcaray L, Fernández-Escalada M et al (2017) The pattern of shikimate pathway and phenylpropanoids after inhibition by glyphosate or quinate feeding in pea roots. Pestic Biochem Physiol 141:96–102. https://doi.org/10.1016/j.pestbp.2016.12.005
Zenk MH (1965) Biosynthese von vanillin in Vanilla planifolia. Andr Z Pflanzenphysiol 53:404
Zhang K, Halitschke R, Yin C et al (2013) Salicylic acid 3-hydroxylase regulates Arabidopsis leaf longevity by mediating salicylic acid catabolism. Proc Natl Acad Sci 110:14807–14812. https://doi.org/10.1073/pnas.1302702110
Zhang Y, Zhao L, Zhao J et al (2017) S5H/DMR6 encodes a salicylic acid 5-hydroxylase that fine-tunes salicylic acid homeostasis. Plant Physiol 175:1082–1093. https://doi.org/10.1104/pp.17.00695
Zheng X, Van Huystee RB (1992) Anionic peroxidase catalysed ascorbic acid and IAA oxidation in the presence of hydrogen peroxide: a defense system against peroxidative stress in peanut plant. Phytochemistry 31:1895–1898. https://doi.org/10.1016/0031-9422(92)80329-D
Zhou XM, MacKenzie AF, Madramootoo CA, Smith DL (1999) Effects of stem-injected plant growth regulators, with or without sucrose, on grain production, biomass and photosynthetic activity of field-grown corn plants. J Agron Crop Sci 183:103–110. https://doi.org/10.1046/j.1439-037X.1999.00331.x
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Rogério Marchiosi, Wanderley Dantas dos Santos and Osvaldo Ferrarese-Filho conceived and revised the manuscript. Aline Finger-Teixeira and Rogério Marchiosi wrote the section of biosynthesis of benzoic acids. Dyoni Mathias de Oliveira wrote the section of the phenylpropanoid pathway and made Fig. 4. Thatiane Rodrigues Mota wrote the section about cellular respiration and photosynthesis. Rogério Marchiosi wrote the section of shikimate pathway and made all other figures. Rogério Barbosa de Lima and Anderson Ricardo Soares wrote the section about lignin metabolism. Rodrigo Polimeni Constantin and Marcela de Paiva Foletto-Felipe prepared the table. Rogério Marchiosi and Josielle Abrahão wrote the section about metabolic actions of simple phenolic acids on plants.
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Marchiosi, R., dos Santos, W.D., Constantin, R.P. et al. Biosynthesis and metabolic actions of simple phenolic acids in plants. Phytochem Rev 19, 865–906 (2020). https://doi.org/10.1007/s11101-020-09689-2
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DOI: https://doi.org/10.1007/s11101-020-09689-2