Biological activity of defence-related plant secondary metabolites

Plant-derived Natural Products: Synthesis, Function, and Application

Volumn , Issue , 2009, Pages 283-299

  Morrissey, John P ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84919980958     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-0-387-85498-4_13     Document Type: Chapter

References (81)

1. Aerts, A.M., Francois, I.E., Meert, E.M., Li, Q.T., Cammue, B.P., and Thevissen, K. (2007) The antifungal activity of RsAFP2, a plant defensin from raphanus sativus, involves the induction of reactive oxygen species in Candida albicans. J Mol Microbiol Biotechnol 13: 243 - 247.
2. Akiyama, K., and Hayashi, H. (2006) Strigolactones: chemical signals for fungal symbionts and parasitic weeds in plant roots. Ann Bot (Lond) 97: 925 - 931.
3. Akiyama, K., Matsuzaki, K., and Hayashi, H. (2005) Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi. Nature 435: 824 - 827.
4. Armah, C.N., Mackie, A.R., Roy, C., Price, K., Osbourn, A.E., Bowyer, P., and Ladha, S. (1999) The membrane-permeabilizing effect of avenacin A-1 involves the reorganization of bilayer cholesterol. Biophys J 76: 281 - 290.
5. Baerson, S.R., Sanchez-Moreiras, A., Pedrol- Bonjoch, N., Schulz, M., Kagan, I.A., Agarwal, A.K., et al. (2005) Detoxification and transcriptome response in Arabidopsis seedlings exposed to the allelochemical benzoxazolin-2(3H)-one. J Biol Chem 280: 21867 - 21881.
6. Bais, H.P., Walker, T.S., Stermitz, F.R., Hufbauer, R.A., and Vivanco, J.M. (2002) Enantiomericdependent phytotoxic and antimicrobial activity of (+/-)-catechin. A rhizosecreted racemic mixture from spotted knapweed. Plant Physiol 128: 1173 - 1179.
7. Bais, H.P., Walker, T.S., Kennan, A.J., Stermitz, F.R., and Vivanco, J.M. (2003a) Structure-dependent phytotoxicity of catechins and other flavonoids: flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots. J Agric Food Chem 51: 897 - 901.
8. Bais, H.P., Vepachedu, R., Gilroy, S., Callaway, R.M., and Vivanco, J.M. (2003b) Allelopathy and exotic plant invasion: from molecules and genes to species interactions. Science 301: 1377 - 1380.
9. Bais, H.P., Weir, T.L., Perry, L.G., Gilroy, S., and Vivanco, J.M. (2006) The role of root exudates in rhizosphere interactions with plants and other organisms. Annu Rev Plant Biol 57: 233 - 266.
10. Baker, D.D., Chu, M., Oza, U., and Rajgarhia, V. (2007) The value of natural products to future pharmaceutical discovery. Nat Prod Rep 24: 1225 - 1244.
11. Balunas, M.J., and Kinghorn, A.D. (2005) Drug discovery from medicinal plants. Life Sci 78: 431 - 441.
12. Bouarab, K., Melton, R., Peart, J., Baulcombe, D., and Osbourn, A. (2002) A saponin-detoxifying enzyme mediates suppression of plant defences. Nature 418: 889 - 892.
13. Buck, C.B. (2008) Defensins' offensive play: exploiting a viral achilles' heel. Cell Host Microbe 3: 3 - 4.
14. Cabral, K.M., Almeida, M.S., Valente, A.P., Almeida, F.C., and Kurtenbach, E. (2003) Production of the active antifungal Pisum sativum defensin 1 (Psd1) in Pichia pastoris: overcoming the inefficiency of the STE13 protease. Protein Expr Purif 31: 115 - 122.
15. Codogno, P., and Meijer, A.J. (2005) Autophagy and signaling: Their role in cell survival and cell death. Cell Death Differ 12 Suppl 2: 1509 - 1518.
16. Cole, D., Pallet, K., and Rodgers, M. (2000) Discovering new modes of action for herbicides and the impact of genomics. Pesticide Outlook 11: 223 - 229.
17. D'Auria, J.C., and Gershenzon, J. (2005) The secondary metabolism of Arabidopsis thaliana: growing like a weed. Curr Opin Plant Biol 8: 308 - 316.
18. Eckstein-Ludwig, U., Webb, R.J., Van Goethem, I.D., East, J.M., Lee, A.G., Kimura, M., et al. (2003) Artemisinins target the SERCA of Plasmodium falciparum. Nature 424: 957 - 961.
19. Ellington, A.A., Berhow, M.A., and Singletary, K.W. (2006) Inhibition of Akt signaling and enhanced ERK1/2 activity are involved in induction of macroautophagy by triterpenoidB-group soyasaponins in colon cancer cells. Carcinogenesis 27: 298 - 306.
20. Field, B., Jordan, F., and Osbourn, A. (2006) First encounters - deployment of defence-related natural products by plants. New Phytol 172: 193 - 207.
21. Francois, I.E., Aerts, A.M., Cammue, B.P., and Thevissen, K. (2005) Currently used antimycotics: spectrum, mode of action and resistance occurrence. Curr Drug Targets 6: 895 - 907.
22. Friedman, M. (2002) Tomato glycoalkaloids: role in the plant and in the diet. J Agric Food Chem 50: 5751 - 5780.
23. Friedman, M. (2006) Potato glycoalkaloids and metabolites: roles in the plant and in the diet. J Agric Food Chem 54: 8655 - 8681.
24. Friedman, M. (2007) Overview of antibacterial, antitoxin, antiviral, and antifungal activities of tea flavonoids and teas. Mol Nutr Food Res 51: 116 - 134.
25. Golenser, J., Waknine, J.H., Krugliak, M., Hunt, N.H., and Grau, G.E. (2006) Current perspectives on the mechanism of action of artemisinins. Int J Parasitol 36: 1427 - 1441.
26. Gomez-Roldan, V., Fermas, S., Brewer, P.B., Puech- Pages, V., Dun, E.A., Pillot, J.P., et al. (2008) Strigolactone inhibition of shoot branching. Nature 455: 189 - 194.
27. Gutterman, J.U., Lai, H.T., Yang, P., Haridas, V., Gaikwad, A., and Marcus, S. (2005) Effects of the tumor inhibitory triterpenoid avicin G on cell integrity, cytokinesis, and protein ubiquitination in fission yeast. Proc Natl Acad Sci U S A 102: 12771 - 12776.
28. Hale, J.D., and Hancock, R.E. (2007) Alternative mechanisms of action of cationic antimicrobial peptides on bacteria. Expert Rev Anti Infect Ther 5: 951 - 959.
29. Halkier, B.A., and Gershenzon, J. (2006) Biology and biochemistry of glucosinolates. Annu Rev Plant Biol 57: 303 - 333.
30. Haridas, V., Li, X., Mizumachi, T., Higuchi, M., Lemeshko, V.V., Colombini, M., and Gutterman, J.U. (2007) Avicins, a novel plant-derived metabolite lowers energy metabolism in tumor cells by targeting the outer mitochondrial membrane. Mitochondrion 7: 234 - 240.
31. Haridas, V., Higuchi, M., Jayatilake, G.S., Bailey, D., Mujoo, K., Blake, M.E., et al. (2001) Avicins: Triterpenoid saponins from Acacia victoriae (Bentham) induce apoptosis by mitochondrial perturbation. Proc Natl Acad Sci U S A 98: 5821 - 5826.
32. Huang, P.R., Yeh, Y.M., and Wang, T.C. (2005) Potent inhibition of human telomerase by helenalin. Cancer Lett 227: 169 - 174.
33. Ito, S., Ihara, T., Tamura, H., Tanaka, S., Ikeda, T., Kajihara, H., et al. (2007) alpha-Tomatine, the major saponin in tomato, induces programmed cell death mediated by reactive oxygen species in the fungal pathogen Fusarium oxysporum. FEBS Lett 581: 3217 - 3222.
34. Iwashina, T. (2003) Flavonoid function and activity to plants and other organisms. Biol Sci Space 17: 24 - 44.
35. Kartal, M. (2007) Intellectual property protection in the natural product drug discovery, traditional herbal medicine and herbal medicinal products. Phytother Res 21: 113 - 119.
36. Kennedy, J., Marchesi, J.R., and Dobson, A.D. (2007) Metagenomic approaches to exploit the biotechnological potential of the microbial consortia of marine sponges. Appl Microbiol Biotechnol 75: 11 - 20.
37. Klee, H. (2008) Plant biology: Hormones branch out. Nature 455: 176 - 177.
38. Konig, G.M., Kehraus, S., Seibert, S.F., Abdel-Lateff, A., and Muller, D. (2006) Natural products from marine organisms and their associated microbes. Chembiochem 7: 229 - 238.
39. Korpan, Y.I., Nazarenko, E.A., Skryshevskaya, I.V., Martelet, C., Jaffrezic-Renault, N., and El'skaya, A.V. (2004) Potato glycoalkaloids: True safety or false sense of security? Trends Biotechnol 22: 147 - 151.
40. Krishna, S., Woodrow, C.J., Staines, H.M., Haynes, R.K., and Mercereau-Puijalon, O. (2006) Re-evaluation of how artemisinins work in light of emerging evidence of in vitro resistance. Trends Mol Med 12: 200 - 205.
41. Krungkrai, J. (2004) The multiple roles of the mitochondrion of the malarial parasite. Parasitology 129: 511 - 524.
42. Krungkrai, J., Burat, D., Kudan, S., Krungkrai, S., and Prapunwattana, P. (1999) Mitochondrial oxygen consumption in asexual and sexual blood stages of the human malarial parasite, Plasmodium falciparum. Southeast Asian J Trop Med Public Health 30: 636 - 642.
43. Landon, C., Pajon, A., Vovelle, F., and Sodano, P. (2000) The active site of drosomycin, a small insect antifungal protein, delineated by comparison with the modeled structure of Rs-AFP2, a plant antifungal protein. J Pept Res 56: 231 - 238.
44. Lemeshko, V.V., Haridas, V., Quijano Perez, J.C., and Gutterman, J.U. (2006) Avicins, natural anticancer saponins, permeabilize mitochondrial membranes. Arch Biochem Biophys 454: 114 - 122.
45. Li, W., Mo, W., Shen, D., Sun, L., Wang, J., Lu, S., et al. (2005a) Yeast model uncovers dual roles of mitochondria in action of artemisinin. PLoS Genet 1: e36.
46. Li, X.X., Davis, B., Haridas, V., Gutterman, J.U., and Colombini, M. (2005b) Proapoptotic triterpene electrophiles (avicins) form channels in membranes: cholesterol dependence. Biophys J 88: 2577 - 2584.
47. Macias, F.A., Molinillo, J.M., Varela, R.M., and Galindo, J.C. (2007) Allelopathy - A natural alternative for weed control. Pest Manag Sci 63: 327 - 348.
48. Madden, L.V., and Wheelis, M. (2003) The threat of plant pathogens as weapons against U.S. crops. Annu Rev Phytopathol 41: 155 - 176.
49. Maor, R., and Shirasu, K. (2005) The arms race continues: battle strategies between plants and fungal pathogens. Curr Opin Microbiol 8: 399 - 404.
50. Meazza, G., Scheffler, B.E., Tellez, M.R., Rimando, A.M., Romagni, J.G., Duke, S.O., et al. (2002) The inhibitory activity of natural products on plant p-hydroxyphenylpyruvate dioxygenase. Phytochemistry 60: 281 - 288.
51. Morre, D.J., Grieco, P.A., and Morre, D.M. (1998) Mode of action of the anticancer quassinoids - inhibition of the plasma membrane NADH oxidase. Life Sci 63: 595 - 604.
52. Morrissey, J.P., and Osbourn, A.E. (1999) Fungal resistance to plant antibiotics as a mechanism of pathogenesis. Microbiol Mol Biol Rev 63: 708 - 724.
53. Mujoo, K., Haridas, V., Hoffmann, J.J., Wachter, G.A., Hutter, L.K., Lu, Y., et al. (2001) Triterpenoid saponins from Acacia victoriae (Bentham) decrease tumor cell proliferation and induce apoptosis. Cancer Res 61: 5486 - 5490.
54. Nagamune, K., Beatty, W.L., and Sibley, L.D. (2007a) Artemisinin induces calcium-dependent protein secretion in the protozoan parasite Toxoplasma gondii. Eukaryot Cell 6: 2147 - 2156.
55. Nagamune, K., Moreno, S.N., and Sibley, L.D. (2007b) Artemisinin-resistant mutants of Toxoplasma gondii have altered calcium homeostasis. Antimicrob Agents Chemother 51: 3816 - 3823.
56. Odds, F.C., Brown, A.J., and Gow, N.A. (2003) Antifungal agents: mechanisms of action. Trends Microbiol 11: 272 - 279.
57. Osbourn, A.E. (2003) Saponins in cereals. Phytochemistry 62: 1 - 4.
58. Parniske, M. (2005) Plant-fungal associations: cue for the branching connection. Nature 435: 750 - 751.
59. Perret, X., Staehelin, C., and Broughton, W.J. (2000) Molecular basis of symbiotic promiscuity. Microbiol Mol Biol Rev 64: 180 - 201.
60. Peters, N.K., Frost, J.W., and Long, S.R. (1986) A plant flavone, luteolin, induces expression of Rhizobium meliloti nodulation genes. Science 233: 977 - 980.
61. Rao, A.V., and Gurfinkel, D.M. (2000) The bioactivity of saponins: Triterpenoid and steroidal glycosides. Drug Metabol Drug Interact 17: 211 - 235.
62. Rimando, A.M., Dayan, F.E., Czarnota, M.A., Weston, L.A., and Duke, S.O. (1998) A new photosystem II electron transfer inhibitor from sorghum bicolor. J Nat Prod 61: 1456.
63. Romagni, J.G., Duke, S.O., and Dayan, F.E. (2000) Inhibition of plant asparagine synthetase by monoterpene cineoles. Plant Physiol 123: 725 - 732.
64. Schmidt, B.M., Ribnicky, D.M., Lipsky, P.E., and Raskin, I. (2007) Revisiting the ancient concept of botanical therapeutics. Nat Chem Biol 3: 360 - 366.
65. Simons, V., Morrissey, J.P., Latijnhouwers, M., Csukai, M., Cleaver, A., Yarrow, C., and Osbourn, A. (2006) Dual effects of plant steroidal alkaloids on Saccharomyces cerevisiae. Antimicrob Agents Chemother 50: 2732 - 2740.
66. Singh, S.B., and Pelaez, F. (2008) Biodiversity, chemical diversity and drug discovery. Prog Drug Res 65: 141, 143 - 174.
67. Smith, J.G., and Nemerow, G.R. (2008) Mechanism of adenovirus neutralization by Human alphadefensins. Cell Host Microbe 3: 11 - 19.
68. Sparg, S.G., Light, M.E., and van Staden, J. (2004) Biological activities and distribution of plant saponins. J Ethnopharmacol 94: 219 - 243.
69. Thevissen, K., Ferket, K.K., Francois, I.E., and Cammue, B.P. (2003a) Interactions of antifungal plant defensins with fungal membrane components. Peptides 24: 1705 - 1712.
70. Thevissen, K., Kristensen, H.H., Thomma, B.P., Cammue, B.P., and Francois, I.E. (2007) Therapeutic potential of antifungal plant and insect defensins. Drug Discov Today 12: 966 - 971.
71. Thevissen, K., Francois, I.E., Takemoto, J.Y., Ferket, K.K., Meert, E.M., and Cammue, B.P. (2003b) DmAMP1, an antifungal plant defensin from dahlia (Dahlia merckii), interacts with sphingolipids from Saccharomyces cerevisiae. FEMS Microbiol Lett 226: 169 - 173.
72. Thevissen, K., Warnecke, D.C., Francois, I.E., Leipelt, M., Heinz, E., Ott, C., et al. (2004) Defensins from insects and plants interact with fungal glucosylceramides. J Biol Chem 279: 3900 - 3905.
73. Thevissen, K., Idkowiak-Baldys, J., Im, Y.J., Takemoto, J., Francois, I.E., Ferket, K.K., et al. (2005) SKN1, a novel plant defensin-sensitivity gene in Saccharomyces cerevisiae, is implicated in sphingolipid biosynthesis. FEBS Lett 579: 1973 - 1977.
74. Thomma, B.P., Cammue, B.P., and Thevissen, K. (2002) Plant defensins. Planta 216: 193 - 202.
75. Umehara, M., Hanada, A., Yoshida, S., Akiyama, K., Arite, T., Takeda-Kamiya, N., et al. (2008) Inhibition of shoot branching by new terpenoid plant hormones. Nature 455: 195 - 200.
76. VanEtten, H.D., Mansfield, J.W., Bailey, J.A., and Farmer, E.E. (1994) Two Classes of Plant Antibiotics: Phytoalexins versus "Phytoanticipins". Plant Cell 6: 1191 - 1192.
77. Verma, C., Seebah, S., Low, S.M., Zhou, L., Liu, S.P., Li, J., and Beuerman, R.W. (2007) Defensins: Antimicrobial peptides for therapeutic development. Biotechnol J 2: 1353 - 1359.
78. Vincken, J.P., Heng, L., de Groot, A., and Gruppen, H. (2007) Saponins, classification and occurrence in the plant kingdom. Phytochemistry 68: 275 - 297.
79. Wink, M. (2003) Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry 64: 3 - 19.
80. Wong, J.H., Xia, L., and Ng, T.B. (2007) A review of defensins of diverse origins. Curr Protein Pept Sci 8: 446 - 459.
81. Xiao, J.X., Huang, G.Q., and Zhang, S.H. (2007) Soyasaponins inhibit the proliferation of Hela cells by inducing apoptosis. Exp Toxicol Pathol 59: 35 - 42.