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2020 | OriginalPaper | Buchkapitel

5. Saponin-Detoxifying Enzymes

verfasst von : Mostafa Abdelrahman, Sudisha Jogaiah

Erschienen in: Bioactive Molecules in Plant Defense

Verlag: Springer International Publishing

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Abstract

Pathogenic fungi usually use different tactics to counteract induced and constitutive plant defense mechanisms that include degradation of any chemical compound and inhibition of plant triggered defenses by producing enzymes. Saponins as major bioactive compounds located in several monocot and dicot plant species and have been proposed to be involved in the defense of plants against pathogen outbreak. However, the capability of several pathogenic fungi to produce saponin-neutralizing enzymes would suggest that they play a major role in ascertaining the effect of interaction between plant and pathogen. Most of the saponin-detoxifying enzymes are glycosyl hydrolases, which catalyze hydrolysis of sugars from saponin aglycone that consists of a sugar chain attached to the C3 carbon, resulting in loss of saponin membranolytic properties and consequently loss of toxicity. In this chapter we will discuss and summarize different saponin-detoxifying enzymes and their effects in plant defense, as ultimate objective to increase crop plant productivity.

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Vorheriges Kapitel Saponins Versus Plant Fungal Pathogens

Nächstes Kapitel Isolation and Characterization of Triterpenoid and Steroidal Saponins

Arneson PA, Durbin RD (1968a) The sensitivity of fungi to α-tomatine. Phytopathology 58:536–537

Arneson PA, Durbin RD (1968b) Studies on the mode of action of tomatine as a fungitoxic agent. Plant Physiol 43:683–686PubMedPubMedCentralCrossRef

Bosetti C, Filomeno M, Riso P et al (2012) Cruciferous vegetables and cancer risk in a network of case-control studies. Ann Oncol 23:2198–2203PubMedCrossRef

Bouarab K, Melton R, Peart J, Baulcombe D, Osbourn A (2002) A saponin-detoxifying enzyme mediates suppression of plant defences. Nature 418:889–892PubMedCrossRef

Bowyer P, Clarke BR, Lunness P, Daniels MJ, Osbourn AE (1995) Host range of a plant pathogenic fungus determined by a saponin detoxifying enzyme. Science 267:371–374PubMedCrossRef

Bushway AA, Bushway RJ, Kim CH (1990) Isolation, partial purification, and characterization of a potato peel α-solanine cleaving glycosidase. Am Potato J 67:233–238CrossRef

Buxdorf K, Yaffe H, Barda O, Levy M (2013) The effects of glucosinolates and their breakdown products on necrotrophic fungi. PLoS One 8:e70771PubMedPubMedCentralCrossRef

Carter JP, Spink J, Cannon PF, Daniels MJ, Osbourn AE (1999) Isolation, characterization, and avenacin sensitivity of a diverse collection of cereal-root-colonizing fungi. Appl Environ Microbiol 65:3364–3372PubMedPubMedCentralCrossRef

Chen J, Ullah C, Reichelt M, Beran F, Yang Z-L, Gershenzon J, Hammerbacher A, Vassão DG (2020) The phytopathogenic fungus Sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an isothiocyanate hydrolase. Nat Comm 11:3090CrossRef

Chew FS (1988) Biological effects of glucosinolates. Am Chem Soc Symp Ser 380:155–181

Cipollini ML, Levey DJ (1997) Why are some fruits toxic? Glycoalkaloids in solanum and fruit choice by vertebrates. Ecology 78:782–798

Ciuffetti LM, VanEtten HD (1996) Virulence of a pisatin demethylase-deficient Nectria haematococca MPVI isolate is increased by transformation with a pisatin demethylase gene. Mol Plant Microbe Interact 9:787–792CrossRef

Crombie WML, Crombie L, Green JB, Lucas JA (1986) Pathogenicity of the take-all fungus to oats: its relationship to the concentration and detoxification of the four avenacins. Phytochemistry 25:2075–2083CrossRef

Curir P, Dolci M, Corea G, Galeotti F, Lanzotti V (2006) The plant antifungal isoflavone genistein is metabolized by Armillaria mellea Vahl to give non-fungitoxic products. Plant Biosyst 140:156–162CrossRef

Davis RH (1991) Glucosinolates. In: D’Mello JP, Duffus CM, Duffus JH (eds) Toxic substances in crop plants. The Royal Society of Chemistry, Cambridge, UK, pp 202–225

Défago G, Kern H (1983) Induction of Fusarium solani mutants insensitive to tomatine, their pathogenicity and aggressiveness to tomato fruits and pea plants. Physiol Plant Pathol 22:29–37CrossRef

Défago G, Kern H, Sedlar L (1983) Genetic analysis of tomatine insensitivity, sterol content and pathogenicity for green tomato fruits in mutants of Fusarium solani. Physiol Mol Plant Pathol 22:39–43CrossRef

Duncan AJ (1991) Glucosinolates. In: D’Mello JP, Duffus CM, Duffus JH (eds) Toxic substances in crop plants. The Royal Society of Chemistry, Cambridge, UK, pp 126–147CrossRef

Essers AJA, Jurgens CMGA, Nout MJR (1995) Contribution of selected fungi to the reduction of cyanogen levels during solid substrate fermentation of cassava. Int J Food Microbiol 26:251–257PubMedCrossRef

Fahey JW, Zalcmann AT, Talalay P (2001) The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56:5–51PubMedCrossRef

Fewell AM, Roddick JG (1993) Interactive antifungal activity of the glycoalkaloids α-solanine and α-chaconine. Phytochemistry 33:323–328CrossRef

Franco P, Spinozzi S, Pagnotta E, Lazzeri L, Ugolini L, Camborata C et al (2016) Development of a liquid chromatography—electrospray ionization—tandem mass spectrometry method for the simultaneous analysis of intact glucosinolates and isothiocyanates in Brassicaceae seeds and functional foods. J Chromatogr A 1428:154–161PubMedCrossRef

Friedman M, Dao L (1992) Distribution of glycoalkaloids in potato plants and commercial potato products. J Agric Food Chem 40:419–423CrossRef

Friedman M, McDonald GM (1997) Potato glycoalkaloids: chemistry, analysis, safety, and plant physiology. Crit Rev Plant Sci 16:55–l 32CrossRef

Fry WE, Myers DF (1981) Hydrogen cyanide metabolism by fungal pathogens of cyanogenic plants. In: Vennesland B, Knowles CJ, Conn EE, Westley J, Wissing F (eds) Cyanide in biology. Academic, London, pp 321–334

Giamoustaris A, Mithen R (1995) The effect of modifying the glucosinolate content of leaves of oilseed rape (Brassica napus ssp. oleifera) on its interaction with specialist and generalist pests. Ann Appl Biol 126:347–363CrossRef

Goodwin RH, Pollock BM (1954) Studies on roots. I. Properties and distribution of fluorescent constituents in Avena roots. Am J Bot 4:516–520CrossRef

Halkier BA, Gershenzon J (2006) Biology and biochemistry of glucosinolates. Ann Rev Plant Biol 57:303–333CrossRef

Hurst WJ, Glinski JA, Miller KB, Apgar J, Davey MH, Stuart DA (2008) Survey of the trans-resveratrol and trans-piceid content of cocoa-containing and chocolate products. J Agric Food Chem 56:8374–8378PubMedCrossRef

Jeschke V et al (2017) How glucosinolates affect generalist Lepidopteran larvae: growth, development and glucosinolate metabolism. Front Plant Sci 8:1995PubMedPubMedCentralCrossRef

Kuroda M, Mimaki Y, Kameyama A et al (1995) Steroidal saponins from Allium chinense and their inhibitory activities on cyclic AMP phosphodiesterase and Na⁺K⁺ ATPase. Phytochemistry 40:1071–1076PubMedCrossRef

Lanzotti V (2012) Bioactive polar natural compounds from garlic and onions. Phytochem Rev 11:179–196CrossRef

Lanzotti V, Romano A, Lanzuise S, Bonanomi G, Scala F (2011) Antifungal saponins from bulbs of white onion, Allium cepa L. Phytochemistry 74:133–139PubMedCrossRef

Maizel JV, Burkhardt HJ, Mitchell HK (1964) Avenacin, an antimicrobial substance isolated from Avena sativa. I. Isolation and antimicrobial activity. Biochemistry 3:424–431PubMedCrossRef

Margolles-Clark E, Tenkanen M, Nakari-Setälä T, Penttila M (1996) Cloning of genes encoding β-l-arabinofuranoside and β-xylosidase from Trichoderma reesei by expression in Saccharomyces cerevisiae. Appl Environ Microbiol 62:3840–3846PubMedPubMedCentralCrossRef

Martínez-Ballesta MC, Moreno DA, Carvajall M (2013) The physiological importance of glucosinolates on plant response to abiotic stress in Brassica. Int J Mol Sci 14:11607–11625CrossRef

Martin-Hernandez AM, Dufresne M, Hugouvieux V, Melton R, Osbourn A (2000) Effects of targeted replacement of the tomatinase gene on the interaction of Septoria lycopersici with tomato plants. Mol Plant Microbe Interact 13:1301–1311PubMedCrossRef

Mimaki Y, Nikaido T, Matsumoto K et al (1994) New steroidal saponins from the bulbs of Allium giganteum exhibiting potent inhibition of cAMP phosphodiesterase activity. Chem Pharm Bull 42:710–714CrossRef

Mirsalikhova NM, Kravets SS, Sokolova SF et al (1993) Inhibition of highly purified porcine kidney Na, K-ATPase by steroid glycosides of the spirostan and furostan series and a study of structure–activity relationships. Chem Nat Comp 29:490–497CrossRef

Mithen R (1992) Leaf glucosinolate profiles and their relationship to pest and disease resistance in oilseed rape. Euphytica 63:71–83CrossRef

Morrissey JP, Osbourn AE (1999) Fungal resistance to plant antibiotics as a mechanism of pathogenesis. Microbiol Mol Biol Rev 63:708–724PubMedPubMedCentralCrossRef

Oda Y, Saito K, Ohara-Takada A, Mori M (2002) Hydrolysis of the potato glycoalkaloid α-chaconine by filamentous fungi. J Biosci Bioeng 94:321–325PubMedCrossRef

Oka K, Okubo A, Kodama M, Otani H (2006) Detoxification of α-tomatine by tomato pathogens Alternaria alternata tomato pathotype and Corynespora cassiicola and its role in infection. J Gen Plant Pathol 72:152–158CrossRef

Osbourn AE (1996) Saponins and plant defence-a soap story. Trends Plant Sci 1:4–9CrossRef

Osbourn AE, Clarke BR, Dow JM, Daniels MJ (1991) Partial characterization of avenacinase from Gaeumannomyces graminis var. avenae. Physiol Mol Plant Pathol 38:301–312CrossRef

Osbourn AE, Clarke BR, Lunness P, Scott PR, Daniels MJ (1994) An oat species lacking avenacin is susceptible to infection by Gaeumannomyces graminis var. tritici. Physiol Mol Plant Pathol 45:457–467CrossRef

Osbourn AE, Bowyer P, Lunness P, Clarke B, Daniels M (1995) Fungal pathogens of oat roots and tomato leaves employ closely related enzymes to detoxify different host plant saponins. Mol Plant Microbe Interact 8:971–978PubMedCrossRef

Osbourn AE, Bowyer P, Daniels MJ (1996) Saponin detoxification by plant pathogenic fungi. In: Waller GR, Yamasaki K (eds) Saponins used in traditional and modern medicine. Advances in experimental medicine and biology, vol 404. Springer, Boston, MA

Papadopoulou K, Melton RE, Leggett M, Daniels MJ, Osbourn AE (1999) Compromised disease resistance in saponin-deficient plants. PNAS 96:12923–12928PubMedCrossRefPubMedCentral

Poulton JE (1988) Localization and catabolism of cyanogenic glycosides. Ciba Found Symp 140:67–91PubMed

Poulton JE, Moller BL (1993) Glucosinolates. Methods Plant Biochem 9:209–237

Rask L et al (2000) Myrosinase: gene family evolution and herbivore defense in Brassicaceae. Plant Mol Biol 42:93–113PubMedCrossRef

Roddick J (1974) The steroidal glycoalkaloid tomatine. Phytochemistry 13:9–25CrossRef

Sánchez-Maldonado AF, Schieber A, Gänzle MG (2016) Antifungal activity of secondary plant metabolites from potatoes (Solanum tuberosum L.): glycoalkaloids and phenolic acids show synergistic effects. J Appl Microbiol 120:955–965PubMedCrossRef

Sandrock RW, VanEtten HD (1998) Fungal sensitivity to and enzymatic degradation of the phytoanticipin α-tomatine. Phytopathology 88:137–143PubMedCrossRef

Sandrock RW, VanEtten HD (2001) The relevance of tomatinase activity in pathogens of tomato: disruption of the β2-tomatinase gene in Colletotrichum coccodes and Septoria lycopersici and heterologous expression of the Septoria lycopersici β2-tomatinase in Nectria haematococca, a pathogen of tomato fruit. Physiol Mol Plant Pathol 58:159–171CrossRef

Sandrock RW, DellaPenna D, VanEtten HD (1995) Purification and characterization of β2-tomatinase, an enzyme involved in the degradation of α-tomatine and isolation of the gene encoding β2-tomatinase from Septoria lycopersici. Mol Plant Microbe Interact 8:960–970PubMedCrossRef

Senegupta S, Prasanna TB, Kasbekar DP (1995) Sterol 14,15 reductase (erg-3) mutations switch the phenotype of Neurospora crassa from sensitivity to the tomato saponin α-tomatine to sensitivity to the pea phytoalexin pisatin. Fungal Genet Newsl 42:71–72

Smith JD, Woldemariam MG, Mescher MC, Jander G, De Moraes CM (2016) Glucosinolates from host plants influence growth of the parasitic plant Cuscuta gronovii and its susceptibility to aphid feeding. Plant Physiol 172:181–197PubMedPubMedCentralCrossRef

Suleman P, Tohamy AM, Saleh AA, Madkour MA, Straney DC (1996) Variation in sensitivity to tomatine and rishitin among isolates of Fusarium oxysporum f.sp. lycopersici, and strains not pathogenic to tomato. Physiol Mol Plant Pathol 48:131–144CrossRef

Teshima Y et al (2013) Identification and biological activity of antifungal saponins from shallot (Allium cepa L. Aggregatum Group). Agric Food Chem (31):7440–7445

VanEtten HD, Sandrock RW, Wasmann CC, Soby SD, McCluskey K, Wang P (1995) Detoxification of phytoanticipins and phytoalexins by phytopathogenic fungi. Can J Bot 73:S518–S525CrossRef

Weltring KM, Wessels J, Geyert R (1997) Metabolism of the potato saponins ɑ-chaconine and ɑ-solanine by Gibberella pilicaris. Phytochemistry 46:1005–1009CrossRef

Wubben JP, Price KR, Daniels MJ, Osbourn AE (1996) Detoxification of oat leaf saponins by Septoria avenae. Phytopathology 86:986–992CrossRef

Yue Q, Bacon CW, Richardson MD (1998) Biotransformation of 2-benzoxazolinone and 6-methoxy-benzoxazolinone by Fusarium moliliforme. Phytochemistry 48:451–454CrossRef

Titel: Saponin-Detoxifying Enzymes
verfasst von: Mostafa Abdelrahman
Sudisha Jogaiah
Verlag: Springer International Publishing
Buch: Bioactive Molecules in Plant Defense
Print ISBN: 978-3-030-61148-4

Electronic ISBN: 978-3-030-61149-1

Copyright-Jahr: 2020
DOI: https://doi.org/10.1007/978-3-030-61149-1_5

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