Abstract
Through secondary or specialised metabolites plants adapt to their environment. A myriad of different compounds plays a significant role in the plant–environment interaction. These compounds help plants in attracting pollinators or deterring herbivores, in their protection from pathogen microorganisms, or in protection from various abiotic stresses. The vast diversity of these compounds is based not only on the ability to rapidly evolve biochemical pathways but also on differential expression of already existing genes in different tissues, and the substrate-binding plasticity of the existing enzymes. The general diversity of biochemical pathways and their evolution is discussed in this chapter.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Adam K-P, Zapp J (1998) Biosynthesis of the isoprene units of chamomile sesquiterpenes. Phytochemistry 48:953–959. https://doi.org/10.1016/S0031-9422(97)00992-8
Anchang KY, Novakovic M, Bukvicki D, Asakawa Y (2016) Bis-bibenzyls from the Cameroon liverwort marchantia debilis. Nat Prod Commun 11:1317–1318
Arimura G, Maffei M (2016) Biodiversity and chemotaxonomic significance of specialized metabolites. In: Plant specialized metabolism. CRC Press, Boca Raton, FL, pp 23–63
Asakawa Y (1982) Chemical constituents of the Hepaticae. In: Fortschritte der Chemie Organischer Naturstoffe/Progress in the chemistry of organic natural products. Springer, New York, pp 1–285
Asakawa Y, Matsuda R (1982) Riccardin C, a novel cyclic bibenzyl derivative from Reboulia hemisphaerica. Phytochemistry 21:2143–2144
Asakawa Y, Tokunaga N, Toyota M et al (1979) Chemosystematics of bryophytes. 1. The distribution of terpenoid of bryophytes. J Hattori Bot Lab
Asakawa Y, Tori M, Takikawa K et al (1987) Cyclic bis (bibenzyls) and related compounds from the liverworts Marchantia polymorpha and Marchantia palmata. Phytochemistry 26:1811–1816
Asakawa Y, Ludwiczuk A, Novakovic M et al (2021) Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 genera of the Marchantiophyta (liverworts): structures, synthesis, and bioactivity. J Nat Prod
Barthlott W, Neinhuis C (1997) Purity of the sacred lotus, or escape from contamination in biological surfaces. Planta 202:1–8
Bartram S, Jux A, Gleixner G, Boland W (2006) Dynamic pathway allocation in early terpenoid biosynthesis of stress-induced lima bean leaves. Phytochemistry 67:1661–1672. https://doi.org/10.1016/j.phytochem.2006.02.004
Bennett RN, Wallsgrove RM (1994) Secondary metabolites in plant defence mechanisms. New Phytol 127:617–633. https://doi.org/10.1111/j.1469-8137.1994.tb02968.x
Bick JA, Lange BM (2003) Metabolic cross talk between cytosolic and plastidial pathways of isoprenoid biosynthesis: unidirectional transport of intermediates across the chloroplast envelope membrane. Arch Biochem Biophys 415:146–154. https://doi.org/10.1016/S0003-9861(03)00233-9
Buchanan BB, Gruissem W, Jones RL (2009) Natural products (secondary metabolites). In: Biochemistry & molecular biology of plants. American Society of Plant Physiologists, Rockville, pp 1251–1268
Buchanan BB, Gruissem W, Jones RL (2015) Biochemistry and molecular biology of plants. Wiley, Boca Raton, FL
Bukvicki D, Gottardi D, Veljic M et al (2012) Identification of volatile components of liverwort (Porella cordaeana) extracts using GC/MS-SPME and their antimicrobial activity. Molecules 17:6982–6995. https://doi.org/10.3390/molecules17066982
Bukvicki DR, Tyagi AK, Gottardi DG et al (2013) Assessment of the chemical composition and in vitro antimicrobial potential of extracts of the liverwort Scapania aspera. Nat Prod Commun 8:1313–1316
Bukvicki D, Stojkovic D, Sokovic M et al (2015) Potential application of Micromeria dalmatica essential oil as a protective agent in a food system. LWT-Food Sci Technol 63:262–267
Bukvicki D, Ciric A, Sokovic M et al (2016) Micromeria thymifolia essential oil suppresses quorum-sensing signaling in Pseudomonas aeruginosa. Nat Prod Commun 11:1903–1906
Bukvicki D, Kovtonyuk NK, Legin AA et al (2021) Hunting for bis-bibenzyls in Primula veris subsp. macrocalyx (Bunge) Lüdi: organ-specific accumulation and cytotoxic activity. Phytochem Lett 44:90–97
Clough RC, Matthis AL, Barnum SR, Jaworski JG (1992) Purification and characterization of 3-ketoacyl-acyl carrier protein synthase III from spinach. A condensing enzyme utilizing acetyl-coenzyme A to initiate fatty acid synthesis. J Biol Chem 267:20992–20998
Davies J (2013) Specialized microbial metabolites: functions and origins. J Antibiot (Tokyo) 66:361–364. https://doi.org/10.1038/ja.2013.61
Degenhardt J, Köllner TG, Gershenzon J (2009) Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry 70:1621–1637. https://doi.org/10.1016/j.phytochem.2009.07.030
Dodd RS, Afzal-Rafii Z (2000) Habitat-related adaptive properties of plant cuticular lipids. Evolution 54:1438–1444
Dodd RS, Poveda MM (2003) Environmental gradients and population divergence contribute to variation in cuticular wax composition in Juniperus communis. Biochem Syst Ecol 31:1257–1270
Dodoš T, Rajčević N, Tešević V et al (2015) Composition of leaf n-alkanes in three Satureja montana L. subspecies from the Balkan Peninsula: ecological and taxonomic aspects. Chem Biodivers 12:157–169
Dodoš T, Rajčević N, Tešević V, Marin PD (2017) Chemodiversity of Epicuticular n-alkanes and morphological traits of natural populations of Satureja subspicata Bart. ex Vis. along Dinaric Alps - ecological and taxonomic aspects. Chem Biodivers 14:e1600201. https://doi.org/10.1002/cbdv.201600201
Dodoš T, Rajčević N, Janaćković P et al (2019a) Intra- and interpopulation variability of Balkan endemic - Satureja kitaibelii T based on n-alkane profile. Biochem Syst Ecol 85:68–71
Dodoš T, Rajčević N, Janaćković P et al (2019b) Essential oil profile in relation to geographic origin and plant organ of Satureja kitaibelii Wierzb. ex Heuff. Ind Crops Prod 139:111549. https://doi.org/10.1016/j.indcrop.2019.111549
Dodoš T, Janković S, Marin PD, Rajčević N (2021) Essential oil composition and micromorphological traits of Satureja montana L., S. subspicata Bartel ex Vis., and S. kitaibelii Wierzb. Ex Heuff. Plant organs. Plants 10:511. https://doi.org/10.3390/plants10030511
Fehling E, Mukherjee KD (1991) Acyl-CoA elongase from a higher plant (Lunaria annua): metabolic intermediates of very-long-chain acyl-CoA products and substrate specificity. Biochim Biophys Acta BBA 1082:239–246
Friederich S, Maier UH, Deus-Neumann B et al (1999a) Biosynthesis of cyclic bis (bibenzyls) in Marchantia polymorpha. Phytochemistry 50:589–598
Friederich S, Rueffer M, Asakawa Y, Zenk MH (1999b) Cytochromes P-450 catalyze the formation of marchantins A and C in Marchantia polymorpha. Phytochemistry 52:1195–1202
Grotewold E (2006) The science of flavonoids. Springer, New York
Gupta PD, Birdi TJ (2017) Development of botanicals to combat antibiotic resistance. J Ayurveda Integr Med 8:266–275. https://doi.org/10.1016/j.jaim.2017.05.004
Ivanov M, Božunović J, Gašić U et al (2022) Bioactivities of Salvia nemorosa L. inflorescences are influenced by the extraction solvents. Ind Crops Prod 175(114260). https://doi.org/10.1016/j.indcrop.2021.114260
Ivković I, Bukvički D, Novaković M et al (2021a) Antibacterial properties of thalloid liverworts Marchantia polymorpha L., Conocephalum conicum (L.) Dum. and Pellia endiviifolia (Dicks.) Dumort. J Serbian Chem Soc 2021:1249–1258
Ivković I, Bukvički D, Novaković M et al (2021b) Assessment of the biological effects of Pellia endiviifolia and its constituents in vitro. Nat prod Commun 16:1934578X211056422. https://doi.org/10.1177/1934578X211056422
Ivković I, Novaković M, Veljić M et al (2021c) Bis-Bibenzyls from the liverwort Pellia endiviifolia and their biological activity. Plants 10. https://doi.org/10.3390/plants10061063
Jenks MA, Tuttle HA, Eigenbrode SD, Feldmann KA (1995) Leaf epicuticular waxes of the eceriferum mutants in Arabidopsis. Plant Physiol 108:369–377
Jocković J, Rajčević N, Terzić S et al (2020) Pericarp features of wild perennial Helianthus L. species as a potential source for improvement of technical and technological properties of cultivated sunflower. Ind Crops Prod 144(112030). https://doi.org/10.1016/j.indcrop.2019.112030
Kabera JN, Semana E, Mussa AR, He X (2014) Plant secondary metabolites: biosynthesis, classification, function and pharmacological properties. J Pharmacy Pharmacol 2:377–339
Kampranis SC, Ioannidis D, Purvis A et al (2007) Rational conversion of substrate and product specificity in a salvia monoterpene synthase: structural insights into the evolution of terpene synthase function. Plant Cell 19:1994–2005. https://doi.org/10.1105/tpc.106.047779
Katoh S, Hyatt D, Croteau R (2004) Altering product outcome in Abies grandis (−)-limonene synthase and (−)-limonene/(−)-α-pinene synthase by domain swapping and directed mutagenesis. Arch Biochem Biophys 425:65–76. https://doi.org/10.1016/j.abb.2004.02.015
Knight TG, Wallwork MA, Sedgley M (2004) Leaf epicuticular wax and cuticle ultrastructure of four Eucalyptus species and their hybrids. Int J Plant Sci 165:27–36
Kosenkova YS, Polovinka MP, Komarova NI et al (2009) Seasonal dynamics of Riccardin C accumulation in Primula macrocalyx Bge. Chem Sustain Dev 17:507–511
Kunst L, Samuels AL (2003) Biosynthesis and secretion of plant cuticular wax. Prog Lipid Res 42:51–80. https://doi.org/10.1016/S0163-7827(02)00045-0
Kunst L, Samuels L (2009) Plant cuticles shine: advances in wax biosynthesis and export. Curr Opin Plant Biol 12:721–727. https://doi.org/10.1016/j.pbi.2009.09.009
Li Y, Kong D, Fu Y et al (2020) The effect of developmental and environmental factors on secondary metabolites in medicinal plants. Plant Physiol Biochem 148:80–89. https://doi.org/10.1016/j.plaphy.2020.01.006
Ludwiczuk A, Skalicka-Woźniak K, Georgiev MI (2017) Terpenoids. In: Pharmacognosy. Elsevier, New York, pp 233–266
Martin DM (2004) Functional characterization of nine Norway spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily. Plant Physiol 135:1908–1927. https://doi.org/10.1104/pp.104.042028
Muzac I, Wang J, Anzellotti D et al (2000) Functional expression of an Arabidopsis cDNA clone encoding a flavonol 3′-O-methyltransferase and characterization of the gene product. Arch Biochem Biophys 375:385–388
Neinhuis C, Koch K, Barthlott W (2001) Movement and regeneration of epicuticular waxes through plant cuticles. Planta 213:427–434. https://doi.org/10.1007/s004250100530
Novaković J, Rajčević N, Garcia-Jacas N et al (2019) Capitula essential oil composition of seven Centaurea species (sect. Acrocentron, Asteraceae) – taxonomic implication and ecological significance. Biochem Syst Ecol 83:83–90. https://doi.org/10.1016/j.bse.2019.01.010
Novakovic M, Bukvicki D, Andjelkovic B et al (2019) Cytotoxic activity of Riccardin and Perrottetin derivatives from the liverwort Lunularia cruciata. J Nat Prod 82:694–701. https://doi.org/10.1021/acs.jnatprod.8b00390
Novaković M, Ludwiczuk A, Bukvicki D, Asakawa Y (2021) Phytochemicals from bryophytes: structures and biological activity. J Serbian Chem Soc 86:1139–1175
Ohlrogge JB, Jaworski JG, Post-Beittenmiller D (1993) De novo fatty acid biosynthesis. CRC Press, Boca Raton, FL, pp 3–32
Osei-Safo D, Dziwornu GA, Salgado A et al (2017) Bi- and bisbibenzyls from the roots of Dichapetalum heudelotii and their antiproliferative activities. Fitoterapia 122:95–100. https://doi.org/10.1016/j.fitote.2017.09.001
Phillips MA, Croteau RB (1999) Resin-based defenses in conifers. Trends Plant Sci 4:184–190
Pichersky E, Gang DR (2000) Genetics and biochemistry of secondary metabolites in plants: an evolutionary perspective. Trends Plant Sci 5:439–445. https://doi.org/10.1016/S1360-1385(00)01741-6
Pichersky E, Lewinsohn E (2011) Convergent evolution in plant specialized metabolism. Annu Rev Plant Biol 62:549–566. https://doi.org/10.1146/annurev-arplant-042110-103814
Post-Beittenmiller D (1996) Biochemistry and molecular biology of wax production in plants. Annu Rev Plant Biol 47:405–430
Rajčević N, Janaćković P, Dodoš T et al (2014a) Leaf n-alkanes as characters differentiating coastal and continental Juniperus deltoides populations from the Balkan Peninsula. Chem Biodivers 11:1042–1052
Rajčević N, Janaćković P, Dodoš T et al (2014b) Biogeographic variation of foliar n-alkanes of Juniperus communis var. saxatilis Pallas from the Balkans. Chem Biodivers 11:1923–1938
Rajčević N, Janaćković P, Dodoš T et al (2015) Essential-oil variability of Juniperus deltoides RP Adams along the East Adriatic Coast–how many chemotypes are there? Chem Biodivers 12:82–95
Rajčević NF, Labus MG, Dodoš TZ et al (2018) Juniperus phoenicea var. turbinata (Guss.) Parl. Leaf essential oil variability in the Balkans. Chem Biodivers 15(e1800208):e1800208. https://doi.org/10.1002/cbdv.201800208
Rajčević N, Nikolić B, Marin PD (2019) Different responses to environmental factors in terpene composition of Pinus heldreichii and P. peuce: ecological and chemotaxonomic considerations. Arch Biol Sci 71:629–637. https://doi.org/10.2298/ABS190705045R
Rajčević N, Dodoš T, Novaković J et al (2020a) Epicuticular wax variability of Juniperus deltoides R.P. Adams from the central Balkan – Ecology and chemophenetics. Biochem Syst Ecol 89:104008. https://doi.org/10.1016/j.bse.2020.104008
Rajčević N, Dodoš T, Novaković J et al (2020b) Differentiation of North-Western Balkan Juniperus communis L. (Cupressaceae) populations – ecological and chemophenetic implications. J Essent Oil Res 32:562–570. https://doi.org/10.1080/10412905.2020.1805038
Rashotte AM, Jenks MA, Feldmann KA (2001) Cuticular waxes on eceriferum mutants of Arabidopsis thaliana. Phytochemistry 57:115–123
Roach CR, Hall DE, Zerbe P, Bohlmann J (2014) Plasticity and evolution of (+)-3-Carene synthase and (-)-Sabinene synthase functions of a Sitka spruce monoterpene synthase gene family associated with weevil resistance. J Biol Chem 289:23859–23869. https://doi.org/10.1074/jbc.M114.571703
Samuels L, Kunst L, Jetter R (2008) Sealing plant surfaces: Cuticular wax formation by epidermal cells. Annu Rev Plant Biol 59:683–707. https://doi.org/10.1146/annurev.arplant.59.103006.093219
Shimakata T, Stumpf PK (1982) Isolation and function of spinach leaf β-ketoacyl-[acyl-carrier-protein] synthases. Proc Natl Acad Sci 79:5808–5812
Smetanska I (2008) Production of secondary metabolites using plant cell cultures. In: Stahl U, Donalies UEB, Nevoigt E (eds) Food biotechnology. Springer, Berlin, pp 187–228
Stojković D, Drakulić D, Gašić U et al (2020a) Ononis spinosa L. an edible and medicinal plant: UHPLC-LTQ Orbitrap/MS chemical profiling and biological activities of the herbal extract. Food Funct 11:7138–7151. https://doi.org/10.1039/D0FO01595D
Stojković D, Gašić U, Drakulić D et al (2020b) Chemical profiling, antimicrobial, anti-enzymatic, and cytotoxic properties of Phlomis fruticosa L. J Pharm Biomed Anal 113884. https://doi.org/10.1016/j.jpba.2020.113884
Stojković D, Drakulić D, Schwirtlich M et al (2021) Extract of Herba Anthrisci cerefolii: chemical profiling and insights into its anti-glioblastoma and antimicrobial mechanism of actions. Pharmaceuticals 14:1–15
Stojković D, Drakulić D, Dias MI et al (2022) Phlomis fruticosa l. exerts in vitro antineurodegenerative and antioxidant activities and induces prooxidant effect in glioblastoma cell line. EXCLI J 21:387–399. https://doi.org/10.17179/EXCLI2021-4487
Takahashi H, Asakawa Y (2017) Transcriptome analysis of marchantin biosynthesis from the liverwort Marchantia polymorpha. Nat Prod Commun 12:1934578X1701200831
Tissier A, Ziegler J, Vogt T (2014) Specialized plant metabolites: diversity and biosynthesis. In: Krauss G-J, Nies DH (eds) Ecological biochemistry. Wiley-VCH, Weinheim, pp 14–37
Tyagi AK, Bukvicki D, Gottardi D et al (2013) Antimicrobial potential and chemical characterization of Serbian liverwort (Porella arboris-vitae): SEM and TEM observations. Evid Based Complement Alternat Med 2013. https://doi.org/10.1155/2013/382927
Velickovic I, Zizak Z, Rajcevic N et al (2020) Examination of the polyphenol content and bioactivities of Prunus spinosa L. fruit extracts. Arch Biol Sci 72:105–115. https://doi.org/10.2298/ABS191217004V
Verpoorte R (2000) Secondary metabolism. In: Metabolic engineering of plant secondary metabolism. Springer, New York, pp 1–29
Vioque J, Kolattukudy PE (1997) Resolution and purification of an aldehyde-generating and an alcohol-generating fatty acyl-CoA reductase from pea leaves (Pisum sativum L.). Arch Biochem Biophys 340:64–72. https://doi.org/10.1006/abbi.1997.9932
von Wettstein-Knowles PM (1982) Elongase and epicuticular wax biosynthesis. Physiol Veg 20:797–809
Wang J, Pichersky E (1999) Identification of specific residues involved in substrate discrimination in two plant O-methyltransferases. Arch Biochem Biophys 368:172–180
Wink M (2010) Introduction: biochemistry, physiology and ecological functions of secondary metabolites. In: Wink M (ed) Biochemistry of plant secondary metabolism. Wiley-Blackwell, Oxford, UK, pp 1–19
Xue D, Zhang X, Lu X et al (2017) Molecular and evolutionary mechanisms of Cuticular wax for plant drought tolerance. Front Plant Sci 8:621. https://doi.org/10.3389/fpls.2017.00621
Yazaki K (2006) ABC transporters involved in the transport of plant secondary metabolites. FEBS Lett 580:1183–1191. https://doi.org/10.1016/j.febslet.2005.12.009
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2023 The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
Rajčević, N., Bukvički, D., Stojković, D., Soković, M. (2023). Biochemistry of Secondary Metabolism in Plants. In: Carocho, M., Heleno, S.A., Barros, L. (eds) Natural Secondary Metabolites. Springer, Cham. https://doi.org/10.1007/978-3-031-18587-8_2
Download citation
DOI: https://doi.org/10.1007/978-3-031-18587-8_2
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-031-18586-1
Online ISBN: 978-3-031-18587-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)