Induced plant secondary metabolites for phytopatogenic fungi control: A review

Journal of Soil Science and Plant Nutrition

Volumn 12, Issue 4, 2012, Pages

  Ribera, A E ^a   Zuniga G ^b  

^a UNIVERSIDAD DE LA FRONTERA   (Chile)

^b UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

Author keywords

Antifungal activity; Phytoalexins; Phytopathogenic fungi; Secondary metabolites

Indexed keywords

EMBRYOPHYTA; FUNGI; TRACHEOPHYTA;

EID: 84875995817     PISSN: 07189516     EISSN: None     Source Type: Journal    
DOI: 10.4067/s0718-95162012005000040     Document Type: Review

References (108)

1. Adrian, M., Jeandet, P., Veneau, J., Weston, L.A., Bessis, R. 1997. Biological activity of resveratrol, a stilbenic compound from grapevines, against Botrytis cinerea, the causal agent for gray mold. J. Chem. Ecol. 23, 1689-1702.
2. Adrian, M., Rajei, H., Jeandet, P., Veneau, J., Bessis, R. 1998. Resveratrol oxidation in Botrytis cinerea conidia. Phytopathology. 88, 472-476.
3. Afek, U., Sztejnberg, A., Carmely, S. 1986. 6,7-Dimethoxycoumarin, a citrus phytoalexin conferring resistance against Phytophthora gummosis. Phytochemistry. 25, 1855-1856.
4. Agrios, G.N. 2004. Losses caused by plant diseases. p. 29-45. Plant Pathology. Elsevier, Oxford, UK.
5. Alfermann, A.W., Petersen, M. 1995. Natural product formation by plant cell biotechnology. Plant Cell, Tissue and Organ Culture. 43, pp. 199-205.
6. Alzate, O., Diego, A., Mier, M., Gonzalo, I.L., Afanador, K., Durango, R., Diego, L., García, P., Carlos, M. 2009. Evaluation of phytotoxicity and antifungal activity against Colletotrichum acutatum of essential oils of thyme (Thymus vulgaris), lemongrass (Cymbopogon citratus), and their main constituents. Vitae. 16, 116-125.
7. Arimoto, Y., Homma, Y., Ohsawa, T. 1986. Studies on citrus melanose and citrus stem-end rot by Diaporthe citri (Faw.) Wolf. Part 5. Identification of phytoalexin in melanose spot. Ann Phytopathol. Soc. Jpn. 52, 620-625.
8. Armah, C.N., Mackie, A.R., Roy, C., Price, K., Osbourn, A.E., Bowyer, P., Ladha, S. 1999. The membrane permeabilizing effect of avenacin A-1 involves the reorganization of bilayer cholesterol. Biophys. J. 76, 281-290.
9. Bala, A., Kollmann, A., Ducrot, P., Majira, A., Kerhoas, L., Leroux, P., Delorme, P., Einhorn, J. 2000. Cis-ε-viniferin, a new antifungal resveratrol dehydrodimer from Cyphostemma crotalaroides roots. J. Phytopathology. 148, 29-32.
10. Bar-Nun, N., Mayer, A.M. 1990. Cucurbitacins protect cucumber tissue against infection by Botrytis cinerea. Phytochemistry. 29, 3, 787-791.
11. Bednarek, P., Schneider, B., Svatos, A., Oldham, N.J., Hahlbrook, K. 2005. Structural complexity, dif- ferential response to infection and tissue specificity of indolic and phenylpropanoid secondary metabolism in Arabidopsis roots. Plant. Physiol. 138, 1058-1070.
12. Bednarek, P., Osbourn, A. 2009. Plant-microbe interactions: Chemical diversity in plant defense. Science. 324, 746-748.
13. Bostock, R.M., Wilcox, M., Wang, G., Adaskaveg, J.E. 1999. Suppression of Monilinia fructicola cutinase production by peach fruit surface phenolic acids. Physiol. Mol. Plant. Pathol. 54, 1-2, 37-50.
14. Brinker, A.M., Seigler, D.S. 1991. Isolation and identification of piceatannol as a phytoalexin from sugarcane. Pytochemistry. 30,10: 3229-3232.
15. Bouchra, C., Achouri, M., Idrissi Hassani, L.M., Hmamouchi, M. 2003. Chemical composition and antifungal activity of essential oils of seven Moroccan Labiatae against Botrytis cinerea Pers: Fr. J. Ethnopharmacol. 89, 165-169.
16. Buzi, A., Chilosi1, G., Timperio, A., Zolla, L., Rossall, S., Magro1, P. 2003. Poplygalacturonase produced by Botrytis fabae as elicitor of two furanoacetylenic phytoalexins in Vicia faba pods. J. Plant. Pathol. 85, 2, 111-116.
17. Calva-Calva, G., Esparza García, F, Pérez Vargas, J., Martínez Juárez, V., Silva Cervantes, S., López Sánchez, C. 2002. Plantas como biorreactores para la producción de biomoléculas y remoción de xenobióticos. Avance y Perspectiva. 21, 307-312.
18. Camele, I., Altieri, L., De Martino, L., De Feo, V., Mancini, E., Rana, G.L. 2012. In vitro control of post-harvest fruit rot fungi by some plant essential oil components. Int. J. Mol. Sci. 13, 2290-2300.
19. Cline, S.D., Coscia, C.J. 1988. Stimulation of sanguinarine production by combined fungal elicitation and hormonal deprivation in cell suspension culture of Papaver bracteatum. Plant. Physiol. 86, 161-165.
20. Commun, C., Mauro, M., Chupeau, Y., Boulay, M., Burrus, M., Jeandet, P. 2003. Phytoalexin production in grapevine protoplasts during isolation and culture. Plant Physiology and Biochemistry. 41, 317-323.
21. Cotoras, M., Folch, C., Mendoza, L. 2004. Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3β-hydroxy-kaurenoic acid. J. Agric. Food Chem. 52, 2821-2826.
22. Croteau, R., Kutchan, T., Lewis, N. 2000. Chapter 24: Natural products (secondary metabolites). In: Buchanan, B., Gruissem, W., Joneas, R. (eds), Biochemistry and Molecular Biology of Plants, American Society of Plant Biologists, Rockville, MD, pp. 1250 -1268.
23. De Lange, J.H., Vincent, A.P., Du Plessis, L.M., Van Wyk, P.J., Ackerman, L.G.J. 1976. Scoparone (6,7-dimethoxycoumarin) induced in citrus peel by black spot, Guignardia citricarpa Kiely. Phytophylactica. 8, 83-84.
24. Dercks, W., Creasy, L. 1989. The significance of stilbene phytoalexins in the Plasmopara viticolagrapevine interaction. Physiol. Mol. Plant Pathol. 34, 189-202.
25. nd ed., ISBN 0-471-49641-3, 507 p.
26. Dixon, R. 2001. Natural products and plant disease resistance. Nature. 411, 843-847.
27. Duke, S.O. 1990. Natural pesticides from plants, In: Janick, J. and Simon, J.E. (eds.). Advances in new crops, Timber Press, Portland, OR, pp. 511-517.
28. Dumas, M.T., Strunz, G.M., Hubbes, M., Jeng, R.S. 1983. Isolation and identification of six mansonones from Ulmus americana infected with Ceratocystis ulmi. Experientia. 39, 1089-1090.
29. Durango, D., Quiñones, W., Torres, F., Rosero, Y., Gil, J., Echeverri, F. 2002. Phytoalexin accumulation in Colombian bean varieties and aminosugars as elicitors. Molecules. 7, 817-832.
30. Einhellig, F.A. 1995. Allelopathy: Current status and future goals. In: Allelopathy: Organisms, processes and applications, eds. Inherjit, Dakshini, K.M.M., Einhellig, F.A. ACS Symposium Series 582. Washington, DC: American Chemical Society, Washington, pp. 1-24.
31. Engelmeier, D., Hadacek, F. 2006. Antifungal natural products: Assays and applications. In: Rai, et al., (eds) Naturally occurring bioactive compounds, Elsevier Sci. Ltd. pp. 423-467.
32. Espinosa-Garcia, F.J., Langenheim, J.H. 1991. Effects of sabinene and γ-terpinene from coastal redwood leaves acting singly or in mixtures on the growth of some of their fungus endophytes. Biochem. Syst. Ecol. 19, 643-650.
33. Fiori, A., Schwan, K., Stangarlin, J., Vida, J., Scapim, C., Cruz, M. and Pascholati, S. 2000. Antifungal activity of leaf extracts and essential oils of some medicinal plants against Didymella bryoniae. J. Phytopathology. 148, 483-487.
34. Glawischnig, E. 2007. Camalexin. Phytochemistry. 68, 401-406.
35. Goetz, G., Fkyerat, A., Métais, N., Kuns, M., Tabacchi, R., Pezet, R., Pont, V. 1999. Resistance factors to grey mould in grape berries: identification of some phenolics inhibitors of Botrytis cinerea stilbene oxidase. Phytochemistry. 52, 759-767.
36. González-Lamothe, R., Mitchell, G., Gattuso, M., Diarra, M.S., Malouin, F., Bouarab, K. 2009. Plant antimicrobial agents and their effects on plant and human pathogens. Int. J. Mol. Sci. 10, 3400-3419.
37. Gonen, L., Viterbo, A., Cantone, F., Staples, R.C., Mayer, A.M. 1996. Effect of cucurbitacins on mRNA coding for laccase in Botrytis cinerea. Phytochemistry. 42, 321-324.
38. Graham, T.L. 1995. Cellular biochemistry of phenylpropanoids responses of soybean to infection by Phytophthora sojae. In: Daniel, M. and Purkayastha, R.P. (Eds.), Handbook of Phytoalexin Metabolism and Action. Marcel Dekker, New York, pp. 85-116.
39. Graham, T.L., Graham, M.Y. 2000. Defense potentiation and competency, redox conditioning effects of salicylic acid and genistein. In: Keen, N. and Stacey, G. (Eds.). Plant-Microbe Interactions, Vol. 5. APS Press, St. Paul.
40. Grayer, R.J., Harborne, J.J. 1994. A survey of antifungal compounds from higher plants. Phytochemistry. 37, 19-42.
41. Grayer, R.J. and Kokubun, T. 2001. Plant-fungal interactions: The search for phytoalexins and other antifungal compounds from higher plants. Phytochemistry. 56, 253-263.
42. Hadacek, F. 2002. Secondary metabolites as plant traits: current assessment and future perspectives. Crit. Rev. Plant Sci. 21, 273-322.
43. Hain, R., Reif, H.J., Krause, E., Langebartels, R., Kindl, H., Vornam, B., Wiese, W., Schmelzer, E., Schreier, P.H., Stocker, R.H., Strenzel, K. 1993. Disease resistance results from foreign phytoalexin expression in a novel plant. Nature. 361, 153 -156.
44. Harris, J.E., Dennis, C. 1976. Antifungal activity of post-infectional metabolites from potato tubers. Physiol. Plant Pathol. 9, 155-165.
45. Harris, J.E., Dennis, C. 1977. The effect of post-infectional potato tuber metabolites and surfactants on zoospores of Oomycetes. Physiol. Plant Pathol. 11, 163-169.
46. Hewitt, G. 2000. New modes of action of fungicides. Pesticide Outlook. 11, 28-32.
47. Hipskind, J.D., Paiva, N.L. 2000. Constitutive accumulation of a resveratrol-glucoside in transgenic alfalfa increases resistance to Phoma medicaginis. Mol. Plant-Microbe Interact. 13, 551-562.
48. Keukens, E.A.J., De Vrije, T., Van Den Boom, C., De Waard, P., Plasmna, H.H., Thiel, F., Chupin, V.Jongen, W.M.F., De Kruijff, B. 1995. Molecular basis of glycoalkaloid induced membrane disruption. Biochim. Biophys. Acta. 1240, 216-228.
49. Kim, S.H., Kang, S.S. and Kim, C.M. 1992. Coumarin glycosides from the roots of Angelica dahurica. Arch. Pharm. Res. 15,73-77.
50. Kim, Y., Lee, C., Kim, H., Lee, H. 2004. Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi. J. Agric. Food Chem. 52, 6096-6100.
51. th International Botrytis Symposium, Reims, France.
52. Kliebenstein, D.J., Rowe, H.C., Denby, K.J. 2005Secondary metabolites influence Arabidopsis/ Botrytis interactions: Variation in host production and pathogen sensitivity. Plant J. 44, 25-36.
53. Kodama, O., Suzuki, T., Miyakawa, J., Akatsuka, T1988. Ultraviolet-induced accumulation of phytoalexins in rice leaves. Agric. Biol. Chem. 522469-2473.
54. Kúc, J. 1995. Phytoalexins stress metabolism and disease resistance in plants. Annu. Rev. Phytopathol33,275-297.
55. Kurita, N., Miyaji, M., Kurane, R., Takahara, Y., Ichimura, K. 1979. Antifungal activity and molecular orbital energies of aldehyde compounds from oils of higher plants. Agric. Biol. Chem. 43, 2365-2371.
56. Kutschy, S.P., Monde, K., Goto, H., Harada, N., Takasugi, M., Dzurilla, M. and Balentova, E. 2001 Synthesis, absolute configuration and enantiomeric enrichment of a cruciferous oxindole phytoalexin, (S)-(-)-spirobrassinin, and its oxazoline analog. J. Organic Chemistry. 66, 3940-3947.
57. Lambers, H., Chapin, F.SIII. and Pons, T.L. 2000. Plant Physiological Ecology. Springer-Verlag, New York Inc. 539 p.
58. Langcake, P., Pryce, R.J. 1976. The production of resveratrol by Vitis vinifera and other members of the Vitaceae as a response to infection or injury. Physiol. Plant Pathol. 9, 77-86.
59. Luo, M., Jiang, L.K., Zou, G.L. 2002. The mechanism of loss of germination ability of A. flavus spore with citral. Zhongguo Shengwu Huaxue Yu Fenzi Shengwu Xuebao 18, 227-233; Chem. Abs. 137, 60144.
60. Minamikawa, T., Akazawa, T., Uritani, I. 1962. Isolation of esculetin from sweet potato roots with black rot. Nature. 195, 726.
61. Minamikawa, T., Akazawa, T., Uritani, I. 1964. Two glucosides of coumarin derivatives in sweet potato roots infected by Ceratocystis fibriata. Agr. Biol. Chem. 28, 230-233.
62. Monde, K., Sasaki, A., Shirata, A., Takasugi, M. 1991. Brassicanal C and two dioxindoles from cabbage. Phytochemistry. 30, 2915-2917.
63. Morrissey, J., Osbourn, A. 1999. Fungal resistance to plant antibiotics as a mechanism of pathogenesis. Microbiology and Molecular Biology Reviews. 63,3,708-724.
64. Müller-Riebau, F., Beger, B., Yegen, O. 1995. Chemical composition and fungitoxic properties to phytopathogenic fungi of essential oils selected aromatic plants growing wild in Turkey. J. Agric. Food Chem. 43, 2262-2266.
65. Nicholson, R., Kollipara, S., Vincent, J., Lyons, P.C., Cadena-Gomez, G. 1987. Phytoalexin synthesis by the Sorghum mesocotyl in response to infection by pathogenic and nonpathogenic fungi. Pro ceedings of the National Academy of Sciences of the United States of America. 84,16, 5520-5524.
66. Nordlund, D.A. 1981. Semichemicals: A review of the terminology; Semiochemicals-their role in pest control, pp. 13-28; eds. Nordlund, D.A., Jones, R.L., Lewis, W.J. New York: John, Wiley. 306 p.
67. Osbourn, A. 1996. Performed antimicrobial compounds and plant defense against fungal attack. Plant Cell. 8, 1821-1831.
68. Osbourn, A. 1999. Review - Antimicrobial phytoprotectants and fungal pathogens, a commentary. Fungal Genetic and Biology. 26, 163-168.
69. Paulitz, T. and Bélanger, R. 2001. Biological control in greenhouse systems. Annu. Rev. Phytopathol. 39, 103-133.
70. Pedras, M.S., Sorensen, J.L. 1998. Phytoalexin accumulation and antifungal compounds from the crucifer wasabi. Phytochemistry. 49, 7, 1959-1965.
71. Pedras, M.S., Sorensen, J.L., Okanga, F.I., Zaharia, I.L. 1999. Wasalexins A and B, new phytoalexins from wasabi: isolation, synthesis, and antifungal activity. Bioorganic & Medicinal Chemistry Letters. 9, 20, 3015-3020.
72. Pedras, M.S.C., Okanga, F.I., Khan, A.Q., Zaharia, I.L. 2000. Phytoalexins from crucifers: synthesis, biosynthesis, and biotransformation. Phytochemistry. 53,161-176.
73. Pedras, M.S., Chumala, P.B., Suchy, M. 2003. Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans, structures, synthesis and antifungal activity. Phytochemistry. 64, 949-956.
74. Pedras, M.S.C., Ahiahonu, P.W.K. 2004. Phytotoxin production and phytoalexin elicitation by the phytopathogenic fungus Sclerotinia sclerotiorum. J. Chem. Ecol. 30, 2163-2179.
75. Pedras, M.S.C., Montaut, S., Suchy, M. 2004. Phytoalexins from the crucifer rutabaga: structuressyntheses, biosyntheses and antifungal activityJournal of Organic Chemistry. 69.4471-4476.
76. Pedras, M.S., Jha, M. 2006. Toward the control oLeptosphaeria maculans: Design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin. Bioorganic & Medicinal Chemistry14,14, 4958-4979.
77. Pelicice, F., Dietrich, S., Bragga, M. 2000. Phytoalexin response of fifteen Brazilian soybeans cultivars. R. Bras. Fisiol.Veg. 12, 1, 45-53.
78. Pezet, R., Pont, V. 1990. Ultrastructural observationof pterostilbene fungitoxicity in dormant conidia oBotrytis cinerea Pers. J. Phytopatho. 129, 29-30.
79. Rizvi, S.J.H., Rizvi, V. 1992. Exploitation of allelochemicals in improving crop productivity. InRizvi, S.J.H. and Rizvi, V. Allelopathy, basic and applied aspects. Chapman and Hall, London. pp443-473.
80. Roetschi, A., Si-Ammour, A., Belbahri, L., MauchF. and Mauch-Mani, B. 2001. Characterization oan Arabidopsis-Phytophthora pathosystem: resistance requires a functional PAD2 gene and is independent of salicylic acid, ethylene and jasmonic acid signaling. Plant. J. 28, 293-305.
81. Saddiq A.A., Khayyat S.A. 2010. Chemical and antimicrobial studies of monoterpene: Citral. Pestic Biochem. Phys. 98, 89-93.
82. Serazetdinova, L., Oldach, K.H., Lörz, H. 2005. Expression of transgenic stilbene synthases in wheacauses the accumulation of unknown stilbene derivatives with antifungal activity. J. Plant. Physiol. 162, 9, 985-1002.
83. Schuhegger, R., Rauhut, T., Glawischnig, E. 2007 Regulatory variability of camalexin biosynthesis., J. Plant. Physiol. 164, 636-644.
84. Seeman, P., Cheng, D., Iles, G.H. 1973. Structure of membrane holes in osmatic and saponin hemolysis. J Cell Biol. 56, 519-527.
85. Shanker, V., Bhalla, R. and Luthura, R. 2003. An overview of the non-mevalonic pathway for terpenoid biosynthesis in plants. J. Biosci. 28, 637-646.
86. Singh, H., Batish, D. and Kohlil, R. 2003. Allelopathic interactions and allelochemicals, new possibilities for sustainable weed management. Critical Review in Plant Sciences. 22 3-4, 239-311.
87. Smith, C.J. 1996. Accumulation of phytoalexins, defense mechanism and stimulus response system. New Phytol. 132, 1-45.
88. Snyder, B.A., Nicholson, R.L. 1990. Synthesis of phytoalexins in sorghum as a site specific response to fungal ingress. Science. 248, 1637-1639.
89. Spring, O., Albert, K., Hager, A. 1982. Three biologically active heliangolides from Helianthus annuus. Phytochemistry. 21,10, 2551-2553.
90. Takasugi, M., Okinaka, S., Katsui, N., Masamune, E., Shirata, A., Ohuchi, M.J. 1985. Isolation and structure of lettucinin A, a novel guaianolide phytoalexin from Lactuca sativa var. capitata (Compositae). J. Chem. Soc. Chem. Commun. 621-622.
91. Takasugi, M., Monde, K., Katsui, N., Shirata, A. 1987. Spirobrassinin, a novel sulfur-containing phytoalexin from the daikon Raphanus sativus L. var. hortensis (Cruciferae). Chem Lett. 1631-1632.
92. Takasugi, M., Monde, K., Katsui, N., Shirata, A. 1988. Novel sulfur-containing phytoalexins from the chinese cabbage Brassica campestris L. ssp. pekinensis (Cruciferae). Journal: Bulletin of the chemical society of Japan. Bull Chem Soc JPN. 61,1,285-289.
93. Tanaka, Y., Data, E.S., Hirose, S., Taniguchi, T. and Uritani, I. 1983. Biochemical changes in second- ary metabolites in wounded and deteriorated cassava roots. Agric. Bio.Chem. 47, 693-700.
94. Talbot, N.J. 2003. On the trail of a cereal killer: exploring the biology of Magnaporthe grisea. Annu. Rev. Microbiol. 57, 177-202.
95. Tamogami, S., Mitani, M., Kodama, O. and Akatsuka, T. 1993. Oryzalexin S structure: a new stemaranetype rice plant phytoalexins and its biogenesis. Tetrahedron. 49, 2025-2032.
96. Thomma, B.P., Nelissen, I., Eggermont, K., Broekaert, W.F. 1999. Deficiency in phytoalexin production causes enhanced susceptibility of Arabidopsis thaliana to the fungus Alternaria brassicicola. Plant J. 19, 163-171.
97. Thomzik, J.E., Stenzel, K., Stocker, R., Schreier, P.H., Hain, R., Stahl, D.J. 1997. Synthesis of a grapevine phytoalexin in transgenic tomatoes (Lycopersicon esculentum Mill.) conditions resistance against Phytophthora infestans. Physiol. Molec. Plant Pathol. 51, 265-278.
98. Tsao, R., Zhou, T. 2000. Antifungal activity of monoterpenoids against postharvest pathogens Botrytis cinerea and Monilinia fructicola. J. Essent. Oil Res. 12, 113-121.
99. Uritani, I., Hoshiya, I. 1953. Phytopathological chemistry of the black-rotted sweet potato. Part 6. Isolation of coumarin substances from potato and their physiology. J. Agric. Chem. Soc. 27, 161-164
100. VanEtten, H.D., Bateman, D.F. 1971. Studies on the mode of action of phaseollin. Phytopathology. 61, 1363-1372
101. Vanisree, M., Lee, C., Lo, S., Nalawade, S., Lin, C., Tsay, H. 2004. Studies on the production of some important secondary metabolites from medicinal plants by plant tissue cultures. Bot. Bull. Acad. Sin. 45, 1-22.
102. Verpoorte, R., Contin, A., Memelink, J. 2002. Biotechnology for the production of plant secondary metabolites. Phytochemistry Reviews, 1, 13-25
103. Veshkurova, O., Golubenko, Z., Pshenichnov, E., Arzanova, I., Uzbekov, V., Sultanova, E., Salikhov, S., Williams, H.J., Reibenspies, J.H., Puckhaber, L.S. 2006. Malvone A. A phytoalexin found in Malva sylvestris (family Malvaceae). Phytochemistry. 67, 21, 2376-2379.
104. Wharton, P., Nicholson, R. 2000. Temporal synthesis and radiolabelling of the sorghum 3-deoxyanthocyanidin phytoalexins and the anthocyanin, cyanidin 3-dimalonyl glucoside. New Phytol. 145, 457-469.
105. Wink, M. 2010. Functions and biotechnology of plant secondary metabolites. Annual Plant Reviews 39, Blackwell Publishing Ltda, USA.
106. Yazdani, D., Tan, Y.H., Zainal Abidin, M.A. and Jaganath, I.B. 2011. A review on bioactive compounds isolated from plants against plant pathogenic fungi. Journal of Medicinal Plants Research. 5,30, 6584-6589.
107. Yourman, L.F., Jeffers, S.N. 1999. Resistance to benzimidazole and dicarboximide fungicides in greenhouse isolates of Botrytis cinerea. Plant. Dis. 83, 569-575.
108. Zhao, C.L., Cui, X.M., Chen, Y.P., Liang, Q. 2010. Key enzymes of triterpenoid saponin biosynthesis and the induction of their activities and gene expressions in plants. Nat. Prod. Commun. 5,7, 1147-58.