Abstract
Plant-derived secondary metabolites provide mankind with a number of economic products that range from pharmaceutical drugs, fragrances, insecticides to flavours and dyes. The incomprehensible amount of chemically and functionally diverse products of secondary metabolism are synthesized through a complex network of enzymatically catalyzed metabolic pathways. The pool of enzymes employed in this biocatalytic landscape includes an assortment of substrate-, stereo-, and regio-specific types. The enzyme-driven reactivity and regio- and stereo-chemistry during the multistep conversion of substrates into diverse products offers lucrative manipulative points of exploitation in metabolic engineering. Parallel to the rich pool and flexibility of enzymes are the numerous genes and other regulatory mechanisms of metabolism that equally offer limitless opportunities for further manipulation to produce novel compounds. These characteristic features of secondary metabolism forms the rationale for its exploitation in producing fine products for human benefit. However, for effective strategies in metabolic engineering, the basic understanding of pathways, gene regulations, and enzymes involved as well as factors affecting the metabolism is required.
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Abbreviations
- CHS:
-
Chalcone synthase
- DMAPP:
-
Dimethylallyl pyrophosphate
- DOXP:
-
1-deoxy-D-xylulose-5-phosphate
- EPSP:
-
Enolpyruvylshikimate-3-phosphate
- ETI:
-
Effector-triggered immunity
- FDA:
-
Food and Drug Administration
- FPP:
-
Farnesyl diphosphate
- GAP:
-
Glyceraldehyde 3-phosphate
- GGPP:
-
Geranylgeranyl diphosphate
- GPP:
-
Geranyl diphosphate
- HMG-CoA:
-
3-hydroxy- 3-methylglutaryl-CoA
- IPP:
-
Isopentenyl pyrophosphate
- MAMPS:
-
Microbe-associated molecular patterns
- MAP:
-
Mitogen-activated protein
- MEP:
-
Methyl-D-erythritol-4-phosphate
- MVA:
-
Mevalonate
- MVAPP:
-
Mevalonate 5-diphosphate
- NLR:
-
NOD-like receptor
- PAL:
-
phenylalanine ammonia lyase
- PAMP:
-
Pathogen-associated molecular patterns
- PEP:
-
Phosphoenolpyruvate
- PKS:
-
Polyketide synthases
- PRR:
-
Pattern recognition receptors
- PTI:
-
Pattern-triggered immunity
- RLK:
-
Receptor-like kinases
- RLP:
-
Receptor-like proteins
- TCA:
-
Tricarboxylic acid
- TF:
-
Transcription factors
- UV:
-
Ultra violet
References
Jones JD, Dangl JL (2006) The plant immune system. Nature 444:323–329
Nishimura MT, Dangl JL (2014) Paired plant immune receptors. Science 344:267
Williams SJ, Sohn KH, Wan L, Bernoux M, Sarris PF, Segonzac C et al (2014) Structural basis for assembly and function of a heterodimeric plant immune receptor. Science 344:299–303
Macho AP, Zipfel C (2014) Plant PRRs and the activation of innate immune signaling. Mol Cell 54:263–272
Dodds PN, Rathjen JP (2010) Plant immunity: towards an integrated view of plant–pathogen interactions. Nat Rev Genet 11:539–548
Wu S, Shan L, He P (2014) Microbial signature-triggered plant defense responses and early signaling mechanisms. Plant Sci 228:118–126
Schwessinger B, Ronald PC (2012) Plant innate immunity: perception of conserved microbial signatures. Plant Biol 63:451–482
Boller T, Felix G (2009) A renaissance of elicitors: perception of microbe-associated molecular patterns and danger signals by pattern-recognition receptors. Annu Rev Plant Biol 60:379–406
Ma Y, Zhao Y, Walker RK, Berkowitz GA (2013) Molecular steps in the immune signaling pathway evoked by plant elicitor peptides (Peps): CPKs, NO and ROS are downstream from the early Ca2+ signal. Plant Physiol 163:1459–1471
Meng X, Zhang S (2013) MAPK cascades in plant disease resistance signaling. Annu Rev Phytopathol 51:245–266
Buscaill P, Rivas S (2014) Transcriptional control of plant defence responses. Curr Opin Plant Biol 20:35–46
Ncube B, Van Staden J (2015) Tilting plant metabolism for improved metabolite biosynthesis and enhanced human benefit. Molecules 20:12698–12731
Wink M (2003) Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 64:3–19
Benderoth M, Textor S, Windsor AJ, Mitchell-Olds T, Gershenzon J, Kroymann J (2006) Positive selection driving diversification in plant secondary metabolism. Proc Natl Acad Sci U S A 103:9118–9123
Mol J, Grotewold E, Koes R (1998) How genes paint flowers and seeds. Trends Plant Sci 3:212–217
van der Fits L, Memelink J (2000) ORCA3, a jasmonate-responsive transcriptional regulator of plant primary and secondary metabolism. Science 289:295–297
Aharoni A, Galili G (2011) Metabolic engineering of the plant primary–secondary metabolism interface. Curr Opin Biotechnol 22:239–244
Malitsky S, Blum E, Less H, Venger I, Elbaz M, Morin S et al (2008) The transcript and metabolite networks affected by the two clades of Arabidopsis glucosinolate biosynthesis regulators. Plant Physiol 184:2021–2049
Li B, Gaudinier A, Tang M, Taylor-Teeples M, Nham NT, Ghaffari C et al (2014) Promoter-based integration in plant defense regulation. Plant Physiol 166:1803–1820
Grubb CD, Abel S (2006) Glucosinolate metabolism and its control. Trends Plant Sci 11:89–100
Soltis NE, Kliebenstein DJ (2015) Natural variation of plant metabolism: genetic mechanisms, interpretive caveats, evolutionary and mechanistic insights. Plant Physiol doi:10.1104/pp.15.01108
Pichersky E, Gang DR (2000) Genetics and biochemistry of secondary metabolites in plants: an evolutionary perspective. Trends Plant Sci 5:439–445
Verpoorte R (2000) Metabolic engineering of plant secondary metabolism. In: Verpoorte R, Alfermann AW (eds) Metabolic engineering of plant secondary metabolism. Kluwer, London
Herrmann KM, Weaver LM (1999) The shikimate pathway. Annu Rev Plant Biol 50:473–503
Jensen RA (1986) The shikimate/arogenate pathway: link between carbohydrate metabolism and secondary metabolism. Physiol Plant 66:164–168
Bentley R, Haslam E (1990) The shikimate pathway-a metabolic tree with many branche. Crit Rev Biochem Mol Biol 25:307–384
Luckner M (2013) Secondary metabolism in microorganisms, plants and animals. Springer Science and Business Media, Berlin
Hawkes T, Lewis T, Coggins J, Mousdale D, Lowe D, Thorneley R (1990) Chorismate synthase. Pre-steady-state kinetics of phosphate release from 5-enolpyruvylshikimate 3-phosphate. Biochem J 265:899–902
White PJ, Millar G, Coggins JR (1998) The overexpression, purification and complete amino acid sequence of chorismate synthase from Escherichia coli K12 and its comparison with the enzyme from Neurospora crassa. Biochem J 251:313–322
Herrmann KM (1995) The shikimate pathway: early steps in the biosynthesis of aromatic compounds. Plant Cell 7:907–919
Haslam E (1993) Shikimic acid: metabolism and metabolites. Wiley, Chichester
Görlach J, Schmid J, Amrhein N (1994) Abundance of transcripts specific for genes encoding enzymes of the prechorismate pathway in different organs of tomato (Lycopersicon esculentum L.) plants. Planta 193:216–223
Jones J, Henstrand J, Handa A, Herrmann K, Weller S (1995) Impaired wound induction of DAHP synthase and altered stem development in transgenic potato plants expressing a DAHP synthase antisense construct. Plant Physiol 108:1413–1421
Chappell J (1995) The biochemistry and molecular biology of isoprenoid metabolism. Plant Physiol 107:1–6
Hunter WN (2007) The non-mevalonate pathway of isoprenoid precursor biosynthesis. J Biol Chem 282:21573–21577
Sacchettini JC, Poulter CD (1997) Creating isoprenoid diversity. Science 277:1788–1789
Ibrahim RK, Anzellotti D (2003) The enzymatic basis of flavonoid biodiversity. Recent Adv Phytochem 37:1–36
Goldstein JL, Brown MS (1990) Regulation of the mevalonate pathway. Nature 343:425–430
Hemmerlin A, Harwood JL, Bach TJ (2012) A raison d’être for two distinct pathways in the early steps of plant isoprenoid biosynthesis? Prog Lipid Res 51:95–148
Eisenreich W, Bacher A, Arigoni D, Rohdich F (2004) Biosynthesis of isoprenoids via the non-mevalonate pathway. Cell Mol Life Sci 61:1401–1426
Rohmer M (1999) The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Nat Prod Rep 16:565–574
Gruchattka E, Hädicke O, Klamt S, Schütz V, Kayser O (2013) In silico profiling of Escherichia coli and Saccharomyces cerevisiae as terpenoid factories. Microb Cell Fact 12:1–18
Bouvier F, Rahier A, Camara B (2005) Biogenesis, molecular regulation and function of plant isoprenoids. Prog Lipid Res 44:357–429
Kuzuyama T, Seto H (2003) Diversity of the biosynthesis of the isoprene units. Nat Prod Rep 20:171–183
Kellogg BA, Poulter CD (1997) Chain elongation in the isoprenoid biosynthetic pathway. Curr Opin Chem Biol 1:570–578
Mihaliak CA, Karp F, Croteau R (1993) 10 Cytochrome P-450 Terpene Hydroxylases. Methods Plant Biochem 9:261
McGarvey DJ, Croteau R (1995) Terpenoid metabolism. Plant Cell 7:1015–1026
Liao P, Hemmerlin A, Bach TJ, Chye M-L (2016) The potential of the mevalonate pathway for enhanced isoprenoid production. Biotechnol Adv. doi:10.1016/j.biotechadv.2016.03.005
Austin MB, Noel JP (2003) The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep 20:79–110
Abe I, Morita H (2010) Structure and function of the chalcone synthase superfamily of plant type III polyketide synthases. Nat Prod Rep 27:809–838
Borejsza-Wysocki W, Hrazdina G (1996) Aromatic polyketide synthases (purification, characterization, and antibody development to benzalacetone synthase from raspberry fruits). Plant Physiol 110:791–799
Sasaki Y, Konishi T, Nagano Y et al (1995) Compartmentalization of two forms of acetyl-CoA carboxylase and plant tolerance towards herbicides. In: Kader JC, Mazliak P (eds) Plant lipid metabolism. Kluwer, Dordrecht
Ferrer J-L, Austin M, Stewart C, Noel J (2008) Structure and function of enzymes involved in the biosynthesis of phenylpropanoids. Plant Physiol Biochem 46:356–370
Lussier F-X, Colatriano D, Wiltshire Z, Page JE, Martin VJ (2012) Engineering microbes for plant polyketide biosynthesis. Comput Struct Biotechnol J 3:1–11
López‐Meyer M, Nessler CL (1997) Tryptophan decarboxylase is encoded by two autonomously regulated genes in Camptotheca acuminata which are differentially expressed during development and stress. Plant J 11:1167–1175
Cauli O, Morelli M (2005) Caffeine and the dopaminergic system. Behav Pharmacol 16:63–77
Dixon RA, Paiva NL (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7:1085–1097
Harborne JB, Williams CA (2000) Advances in flavonoid research since 1992. Phytochemistry 55:481–504
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
Gurib-Fakim A (2006) Medicinal plants: traditions of yesterday and drugs of tomorrow. Mol Aspects Med 27:1–93
Chotani G, Dodge T, Hsu A, Kumar M, LaDuca R, Trimbur D et al (2000) The commercial production of chemicals using pathway engineering. Biochim Biophys Acta (BBA) 1543:434–455
Croteau R, Kutchan TM, Lewis NG (2000) Natural products (secondary metabolites). Biochem Mol Biol Plant 24:1250–1319
Burda S, Oleszek W (2001) Antioxidant and antiradical activities of flavonoids. J Agric Food Chem 49:2774–2779
Fredholm BB, Bättig K, Holmén J, Nehlig A, Zvartau EE (1999) Actions of caffeine in the brain with special reference to factors that contribute to its widespread use. Pharmacol Rev 51:83–133
Houghton PJ, Ren Y, Howes M-J (2006) Acetylcholinesterase inhibitors from plants and fungi. Nat Prod Rep 23:181–199
Facchini PJ (1999) Plant secondary metabolism: out of the evolutionary abyss. Trends Plant Sci 4:382–384
Facchini PJ, De Luca V (1995) Phloem-specific expression of tyrosine/dopa decarboxylase genes and the biosynthesis of isoquinoline alkaloids in Opium poppy. Plant Cell 7:1811–1821
Unver N (2007) New skeletons and new concepts in Amaryllidaceae alkaloids. Phytochem Rev 6:125–135
Pandey S, Kekre N, Naderi J, McNulty J (2005) Induction of apoptotic cell death specifically in rat and human cancer cells by pancratistatin. Artif Cells Blood Substit Immobil Biotechnol 33:279–295
McLachlan A, Kekre N, McNulty J, Pandey S (2005) Pancratistatin: a natural anti-cancer compound that targets mitochondria specifically in cancer cells to induce apoptosis. Apoptosis 10:619–630
McNulty J, Thorat A, Vurgun N, Nair JJ, Makaji E, Crankshaw DJ et al (2010) Human cytochrome P450 liability studies of trans-dihydronarciclasine: a readily available, potent, and selective cancer cell growth inhibitor. J Nat Prod 74:106–108
Kato M, Kanehara T, Shimizu H, Suzuki T, Gillies FM, Crozier A et al (1996) Caffeine biosynthesis in young leaves of Camellia sinensis: in vitro studies on N‐methyltransferase activity involved in the conversion of xanthosine to caffeine. Physiol Plant 98:629–636
Porkka-Heiskanen T, Strecker RE, Thakkar M, Bjørkum AA, Greene RW, McCarley RW (1997) Adenosine: a mediator of the sleep-inducing effects of prolonged wakefulness. Science 276:1265–1268
Crozier A, Jaganath IB, Clifford MN (2006) Phenols, polyphenols and tannins: an overview. In: Crozier A, Clifford MN, Ashihara H (eds) Plant secondary metabolites-occurrence, structure and role in the diet. Blackwell, Oxford
Espín JC, García-Conesa MT, Tomás-Barberán FA (2007) Nutraceuticals: facts and fiction. Phytochemistry 68:2986–3008
Waterman PG, Mole S (1994) Analysis of phenolic plant metabolites. Blackwell Scientific, London
Williams CA, Harborne JB, Geiger H, Hoult JRS (1999) The flavonoids of Tanacetum parthenium and T. vulgare and their anti-inflammatory properties. Phytochemistry 51:417–423
Wallace G, Fry SC (1994) Phenolic components of the plant cell wall. Int Rev Cytol 151:229–268
Schofield P, Mbugua D, Pell A (2001) Analysis of condensed tannins: a review. Anim Feed Sci Technol 91:21–40
Zulak KG, Bohlmann J (2010) Terpenoid biosynthesis and specialized vascular cells of conifer defense. J Integr Plant Biol 52:86–97
Celenza JL, Quiel JA, Smolen GA, Merrikh H, Silvestro AR, Normanly J et al (2005) The Arabidopsis ATR1 Myb transcription factor controls indolic glucosinolate homeostasis. Plant Physiol 137:253–262
Pierpoint W (1994) Salicylic acid and its derivatives in plants: medicines, metabolites and messenger molecules. Adv Bot Res 53:412
Grotewold E (2008) Transcription factors for predictive plant metabolic engineering: are we there yet? Curr Opin Biotechnol 19:138–144
Dixon RA (2005) Engineering of plant natural product pathways. Curr Opin Plant Biol 8:329–336
Mol J, Jenkins G, Schäfer E, Weiss D, Walbot V (1996) Signal perception, transduction, and gene expression involved in anthocyanin biosynthesis. Crit Rev Plant Sci 15:525–557
Grotewold E, Sainz MB, Tagliani L, Hernandez JM, Bowen B, Chandler VL (2000) Identification of the residues in the Myb domain of maize C1 that specify the interaction with the bHLH cofactor R. Proc Natl Acad Sci U S A 97:13579–13584
Henkes S, Sonnewald U, Badur R, Flachmann R, Stitt M (2001) A small decrease of plastid transketolase activity in antisense tobacco transformants has dramatic effects on photosynthesis and phenylpropanoid metabolism. Plant Cell 13:535–551
Tamagnone L, Merida A, Parr A, Mackay S, Culianez-Macia FA, Roberts K et al (1998) The AmMYB308 and AmMYB330 transcription factors from Antirrhinum regulate phenylpropanoid and lignin biosynthesis in transgenic tobacco. Plant Cell 10:135–154
Shufflebottom D, Edwards K, Schuch W, Bevan M (1993) Transcription of two members of a gene family encoding phenylalanine ammonia‐lyase leads to remarkably different cell specificities and induction patterns. Plant J 3:835–845
Weisshaar B, Jenkins GI (1998) Phenylpropanoid biosynthesis and its regulation. Curr Opin Plant Biol 1:251–257
Gantet P, Memelink J (2002) Transcription factors: tools to engineer the production of pharmacologically active plant metabolites. Trends Pharmacol Sci 23:563–569
Schmid J, Amrhein N (1995) Molecular organization of the shikimate pathway in higher plants. Phytochemistry 39:737–749
Poulsen C, Verpoorte R (1991) Roles of chorismate mutase, isochorismate synthase and anthranilate synthase in plants. Phytochemistry 30:377–386
Ziegler J, Facchini PJ (2008) Alkaloid biosynthesis: metabolism and trafficking. Annu Rev Plant Biol 59:735–769
De Luca V, St Pierre B (2000) The cell and developmental biology of alkaloid biosynthesis. Trends Plant Sci 5:168–173
Bailey JE, Sburlati A, Hatzimanikatis V, Lee K, Renner WA, Tsai PS (1996) Inverse metabolic engineering: a strategy for directed genetic engineering of useful phenotypes. Biotechnol Bioeng 52:109–121
Bailey JE (1991) Toward a science of metabolic engineering. Science 252:1668–1675
Sauer U (2006) Metabolic networks in motion: 13C‐based flux analysis. Mol Syst Biol 2:1–10
Ncube B, Finnie J, Van Staden J (2012) Quality from the field: The impact of environmental factors as quality determinants in medicinal plants. S Afr J Bot 82:11–20
Ncube B, Finnie JF, Van Staden J (2014) Carbon–nitrogen ratio and in vitro assimilate partitioning patterns in Cyrtanthus guthrieae L. Plant Physiol Biochem 74:246–254
Sato F, Hashimoto T, Hachiya A, Tamura K-i, Choi K-B, Morishige T et al (2001) Metabolic engineering of plant alkaloid biosynthesis. Proc Natl Acad Sci U S A 98:367–372
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The National Research Foundation of South Africa is gratefully acknowledged for financial support.
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Ncube, B., Ndhlala, A.R., Van Staden, J. (2017). Secondary Metabolism and the Rationale for Systems Manipulation. In: Jha, S. (eds) Transgenesis and Secondary Metabolism. Reference Series in Phytochemistry. Springer, Cham. https://doi.org/10.1007/978-3-319-28669-3_23
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