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Production of Plant Bioactive Triterpenoid and Steroidal Saponins

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Bioactive Molecules in Plant Defense

Abstract

Saponins are triterpenoid or steroid glycosides that play various biological activities in different plant species. The broad-spread existence of saponin in several plant species, and the potential for saponin pharmaceutical applications have resulted in the extraction and identification of many saponin compounds in various plant species. Although an extensive efforts have been invested in the extraction, isolation and chemical structure identification of saponin compounds, which are important to extend our knowledge of saponin structures, recent progress has been given to the biosynthesis and distribution of saponin compounds and their biological activity in various plants. In this chapter, we summarized and discussed the recent progress on saponin biosynthesis pathway and genes involved in the up and downstream pathway of saponins.

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References

  • Abdelrahman M, Hirata S, Ito S-I, Yamauchi N, Shigyo M (2014) Compartmentation and localization of bioactive metabolites in different organs of Allium roylei. Biosci Biotechnol Biochem 78:1112–1122

    Article  PubMed  CAS  Google Scholar 

  • Abdelrahman M, El-Sayed M, Jogaiah S, Burritt DJ, Tran LP (2017a) The “STAY-GREEN” trait and phytohormone signaling networks in plants under heat stress. Plant Cell Rep 36:1009–1025

    Article  PubMed  CAS  Google Scholar 

  • Abdelrahman M, Burritt DJ, Tran LP (2017b) The use of metabolomic quantitative trait locus mapping and osmotic adjustment traits for the improvement of crop yields under environmental stresses. Semin Cell Dev Biol 83:86–94

    Article  PubMed  CAS  Google Scholar 

  • Abdelrahman M, El-Sayed M, Sato S, Hirakawa H, Ito S-I, Tanaka K, Mine Y, Sugiyama N, Suzuki Y, Yamauchi N, Shigyo M (2017c) RNA-sequencing-based transcriptome and biochemical analyses of steroidal saponin pathway in a complete set of Allium fistulosum-A. cepa monosomic addition lines. PLoS One 12:e0181784

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Abdelrahman M, Mahmoud HYAH, El-Sayed M, Tanaka S, Tran LS (2017d) Isolation and characterization of Cepa2, a natural alliospiroside A, from shallot (Allium cepa L. Aggregatum group) with anticancer activity. Plant Physiol Biochem 116:167–173

    Article  PubMed  CAS  Google Scholar 

  • Abdelrahman M, El-Sayed MA, Hashem A, Abd_Allah EF, Alqarawi AA, Burritt DJ, Tran LP (2018) Metabolomics and transcriptomics in legumes under phosphate deficiency in relation to nitrogen fixation by root nodules. Front Plant Sci 9:922

    Article  PubMed  PubMed Central  Google Scholar 

  • Abdelrahman M, Hirata S, Sawada Y, Hirai MY, Sato S, Hirakawa H, Mine Y, Tanaka K, Shigyo M (2019) Widely targeted metabolome and transcriptome landscapes of Allium fistulosum–A. cepa chromosome addition lines revealed a flavonoid hot spot on chromosome 5A. Sci Rep 9:3541

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Abe I, Rohmer M, Prestwich GC (1993) Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes. Chem Rev 93:2189–2206

    Article  CAS  Google Scholar 

  • Augustin JM, Kuzina V, Andersen SB, Bak S (2011) Molecular activities, biosynthesis and evolution of triterpenoidsaponins. Phytochemistry 72:435–457

    Article  PubMed  CAS  Google Scholar 

  • Augustin JM, Drok S, Shinoda T, Sanmiya K, Nielsen JK, Khakimov B et al (2012) UDP-glycosyltransferases from the UGT73C subfamily in Barbarea vulgaris catalyze sapogenin 3-O-glucosylation in saponin-mediated insect resistance. Plant Physiol 160:1881–1895

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Ayoola GA (2008) Phytochemical screening and antioxidant activities of some selected medicinal plants used for malaria therapy in southwestern Nigeria. Trop J Pharm Res 7:1019–1024

    Google Scholar 

  • Bak S, Kahn RA, Olsen CE, Halkier BA (1997) Cloning and expression in Escherichia coli of the obtusifoliol 14α-demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14α-demethylases (CYP51) from fungi and mammals. Plant J 11:191–201

    Article  PubMed  CAS  Google Scholar 

  • Cabello-Hurtado F, Taton M, Forthoffer N, Kahn R, Bak S, Rahier A, Werck-Reichhart D (1999) Optimized expression and catalytic properties of a wheat obtusifoliol 14α-demethylase (CYP51) expressed in yeast. Complementation of erg11Delta yeast mutants by plant CYP51. Eur J Biochem 262:435–446

    Article  PubMed  CAS  Google Scholar 

  • Cammareri M, Consiglio MF, Pecchia P, Corea G, Lanzotti V, Iebas JI, Tavae A, Conicella C (2008) Molecular characterization of β-amyrin synthase from Aster sedifolius L. and triterpenoid saponin analysis. Plant Sci 175:255–261

    Article  CAS  Google Scholar 

  • Challinor VL, De Voss JJ (2013) Open-chain steroidal glycosides, a diverse class of plant saponins. Nat Prod Rep 30:429–454

    Article  PubMed  CAS  Google Scholar 

  • Connolly JD, Hill RA (2000) Triterpenoids. Nat Prod Rep 17:463–482

    Article  PubMed  CAS  Google Scholar 

  • Davis EM, Croteau R (2000) Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes. Top Curr Chem 209:53–95

    Article  CAS  Google Scholar 

  • Field B, Osbourn AE (2008) Metabolic diversification-independent assembly of operon-like gene clusters in different plants. Science 320:543–547

    Article  CAS  PubMed  Google Scholar 

  • Guerriero G, Berni R, Muñoz-Sanchez JA, Apone F, Abdel-Salam EM, Qahtan AA, Alatar AA, Cantini C, Cai G, Hausman J-F, Siddiqui KS, Hernández-Sotomayor SMT, Faisal M (2018) Production of plant secondary metabolites: examples, tips and suggestions for biotechnologists. Genes 9:309

    Article  PubMed Central  CAS  Google Scholar 

  • Han JY, Kim HJ, Kwon YS, Choi YE (2011) The Cyt P450 enzyme CYP716A47 catalyzes the formation of protopanaxadiol from dammarenediol-II during ginsenoside biosynthesis in Panax ginseng. Plant Cell Physiol 52:2062–2073

    Article  PubMed  CAS  Google Scholar 

  • Han JY, Hwang HS, Choi SW, Kim HJ, Choi YE (2012) Cytochrome P450 CYP716A53v2 catalyzes the formation of protopanaxatriol from protopanaxadiol during ginsenoside biosynthesis in Panax ginseng. Plant Cell Physiol 53:1535–1545

    Article  PubMed  CAS  Google Scholar 

  • Han JY, Kim MJ, Ban YW, Hwang HS, Choi YE (2013) The involvement of β-amyrin 28-oxidase (CYP716A52v2) in oleanane-type ginsenoside biosynthesis in Panax ginseng. Plant Cell Physiol 54:2034–2046

    Article  PubMed  CAS  Google Scholar 

  • Haralampidis K, Trojanowska M, Osbourn AE (2002) Biosynthesis of triterpenoid saponins in plants. Adv Biochem Eng Biotech 75:31–49

    CAS  Google Scholar 

  • Hidalgo D, Sanchez R, Lalaleo L, Bonfill M, Corchete P, Palazon J (2018) Biotechnological production of pharmaceuticals and biopharmaceuticals in plant cell and organ cultures. Curr Med Chem 25:3577–3596

    Article  PubMed  CAS  Google Scholar 

  • Huang L, Li J, Ye H, Li C, Wang H, Liu B, Zhang Y (2012) Molecular characterization of the pentacyclictriterpenoid biosynthetic pathway in Catharanthusroseus. Planta 236:1571–1581

    Article  PubMed  CAS  Google Scholar 

  • Itkin M, Heinig U, Tzfadia O, Bhide AJ, Shinde B, Cardenas PD, Bocobza SE, Unger T, Malitsky S, Finkers R, Tikunov Y, Bovy A, Chikate Y, Singh P, Rogachev I, Beekwilder J, Giri AP, Aharoni A (2013) Biosynthesis of antinutritional alkaloids in solanaceous crops is mediated by clustered genes. Science 341:175–179

    Article  PubMed  CAS  Google Scholar 

  • Jung SC et al (2014) Two ginseng UDP-Glycosyltransferases synthesize Ginsenoside Rg(3) and Rd. Plant Cell Physiol 55:2177–2188

    Article  PubMed  CAS  Google Scholar 

  • Kahn RA, Durst F (2000) Function and evolution of plant cytochrome P450. Recent Adv Phytochem 34:151–189

    Article  CAS  Google Scholar 

  • Kalra S, Puniya PL, Kulshreshtha D, Kumar S, Kaur J, Ramachandran S, Singh K (2013) De novo transcriptome sequencing reveals important molecular networks and metabolic pathways of the plant, Chlorophytum borivilianum. PLoS One 8:e83336

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Kuo RY, Qian K, Morris-Natschke SL, Lee KH (2009) Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents. Nat Prod Rep 26:1321–1344

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Lanzotti V, Romano A, Lanzuise S, Bonanomi G, Scala F (2012) Antifungal saponins from bulbs of white onion, Allium cepa L. Phytochemistry 74:133–139

    Article  PubMed  CAS  Google Scholar 

  • Ma YX, Fu HZ, Li M, Sun W, Xu B, Cui JR (2007) An anticancer effect of a new saponin component from Gymnocladus chinensis Baillon through inactivation of nuclear factor-kappa B. Anti-Cancer Drugs 18:41–46

    Article  PubMed  CAS  Google Scholar 

  • Ma C-H, Gao Z-J, Zhang J-J, Zhang W, Shao J-H, Hai M-R, Chen J-W, Yang S-C, Zhang G-H (2016) Candidate genes involved in the biosynthesis of triterpenoid saponins in Platycodon grandiflorum identified by transcriptome analysis. Front Plant Sci 7:673

    PubMed  PubMed Central  Google Scholar 

  • Meesapyodsuk D, Balsevich J, Reed DW, Covello PS (2007) Saponin biosynthesis in Saponaria vaccaria. cDNAs encoding β-amyrin synthase and a triterpene carboxylic acid glucosyltransferase. Plant Physiol 143:959–969

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Moses T, Papadopoulou KK, Osbourn A (2014) Metabolic and functional diversity of saponins, biosynthetic intermediates and semi-synthetic derivatives. Crit Rev Biochem Mol Biol 49:439–462

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Mostafa A, Sudisha J, El-Sayed M, Ito S-I, Ikeda T, Yamauchi N, Shigyo M (2013) Aginosidesaponin, a potent antifungal compound, and secondary metabolite analyses from Allium nigrum L. Phytochem Lett 6:274–280

    Article  CAS  Google Scholar 

  • Ncube B, Staden V, Tilting J (2015) Plant metabolism for improved metabolite biosynthesis and enhanced human benefit. Molecules 20:12698–12731

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Nelson D (2006) Plant cytochrome P450s from moss to poplar. Phytochem Rev 5:193–204

    Article  CAS  Google Scholar 

  • Paquette SM, Bak S, Feyereisen R (2000) Intron–exon organization and phylogeny in a large superfamily, the paralogous cytochrome P450 genes of Arabidopsis thaliana. DNA Cell Biol 19:307–317

    Article  PubMed  CAS  Google Scholar 

  • Paquette S, Møller BL, Bak S (2003) On the origin of family 1 plant glycosyltransferases. Phytochemistry 62:399–413

    Article  PubMed  CAS  Google Scholar 

  • Pérez AJ, Calle JM, Simonet AM, Guerra JO, Stochmal A, Macías FA (2013) Bioactive steroidal saponins from Agave offoyana flowers. Phytochemistry 95:298–307

    Article  PubMed  CAS  Google Scholar 

  • Rohdich F, Kis K, Bacher A, Eisenreich W (2001) The nonmevalonate pathway of isoprenoids: genes, enzymes and intermediates. Curr Opin Chem Biol 5:535–540

    Article  PubMed  CAS  Google Scholar 

  • Sawai S, Saito K (2011) Triterpenoid biosynthesis and engineering in plants. Front Plant Sci 2:25

    Article  PubMed  PubMed Central  Google Scholar 

  • Seki H, Ohyama K, Sawai S, Mizutani M, Ohnishi T, Sudo H, Akashi T, Aoki T, Saito K, Muranaka T (2008) Licorice β-amyrin 11-oxidase, a cytochrome P450 with a key role in the biosynthesis of the triterpene sweetener glycyrrhizin. Proc Natl Acad Sci USA 105:14204–14209

    Article  PubMed  PubMed Central  Google Scholar 

  • Shibuya M, Hoshino M, Katsube Y, Hayashi H, Kushiro T, Ebizuka Y (2006) Identification of β-amyrin and sophoradiol 24-hydroxylase by expressed sequence tag mining and functional expression assay. FEBS J 273:948–959

    Article  PubMed  CAS  Google Scholar 

  • Sparg SG, Light ME, Staden JV (2004) Biological activities and distribution of plant saponins. J Ethnopharmacol 94:219–243

    Article  PubMed  CAS  Google Scholar 

  • Tan N, Zhou J, Zhao S (1999) Advances in structural elucidation of glucuronideoleanane-type triterpene carboxylic acid 3,28-O-bisdesmosides (1962–1997). Phytochemistry 52:153–192

    Article  CAS  Google Scholar 

  • Vincken JP, Heng L, Groot A, Gruppen H (2007) Saponins, classification and occurrence in the plant kingdom. Phytochemistry 68:275–297

    Article  PubMed  CAS  Google Scholar 

  • Wei W, Wang P, Wei Y, Liu Q, Yang C, Zhao G, Yue J, Yan X, Zhou Z (2015) Characterization of Panax ginseng UDP-Glycosyltransferases catalyzing protopanaxatriol and biosyntheses of bioactive ginsenosides F1 and Rh1 in metabolically engineered yeasts. Mol Plant 8:1412–1424

    Article  PubMed  CAS  Google Scholar 

  • Werck-Reichhart D, Bak S, Paquette S (2002) Cytochrome P450. Arabidopsis Book 1:e0028

    Article  PubMed  PubMed Central  Google Scholar 

  • Yan MC, Liu Y, Chen H, Ke Y, Xu QC, Cheng MS (2006) Synthesis and antitumor activity of two natural N-acetylglucosamine-bearing triterpenoidsaponins: lotoidoside D and E. Bioorg Med Chem Lett 16:4200–4204

    Article  PubMed  CAS  Google Scholar 

  • Yan X, Fan Y, Wei W, Wang P, Liu Q, Wei Y, Zhang L, Zhao G, Yue J, Zhou Z (2014) Production of bioactive ginsenoside compound K in metabolically engineered yeast. Cell Res 24:770–773

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Yendo ACA, de Costa F, Gosmann G, Fett-Neto AG (2010) Production of plant bioactive triterpenoid saponins: elicitation strategies and target genes to improve yields. Mol Biotechnol 46:94–104

    Article  PubMed  CAS  Google Scholar 

  • Zhao YJ, Li C (2018) Biosynthesis of plant triterpenoid saponins in microbial cell factories. J Agric Food Chem 66:12155–12165

    Article  PubMed  CAS  Google Scholar 

  • Zhao M, Lin Y, Wang Y, Li X, Han Y, Wang K, Sun C, Wang W, Zhang M (2019) Transcriptome analysis identifies strong candidate genes for ginsenoside biosynthesis and reveals its underlying molecular mechanism in Panax ginseng C.A. Meyer. Sci Rep 9:615

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Zheng X, Xu H, Ma X, Zhan R, Chen W (2014) Triterpenoid Saponin biosynthetic pathway profiling and candidate gene mining of the Ilex asprella root using RNA-Seq. Int J Mol Sci 15:5970–5987

    Article  PubMed  PubMed Central  CAS  Google Scholar 

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Authors and Affiliations

  1. Botany Department, Faculty of Science, Aswan University, Aswan, Egypt

    Mostafa Abdelrahman

  2. Department of Biotechnology, Karnatak University, Dharwad, India

    Sudisha Jogaiah

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  1. Mostafa Abdelrahman
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  2. Sudisha Jogaiah
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Abdelrahman, M., Jogaiah, S. (2020). Production of Plant Bioactive Triterpenoid and Steroidal Saponins. In: Bioactive Molecules in Plant Defense. Springer, Cham. https://doi.org/10.1007/978-3-030-61149-1_2

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