Phenolics and plant allelopathy

Molecules

Volumn 15, Issue 12, 2010, Pages 8933-8952

  Li, Zhao Hui ^a,b   Wang, Qiang ^a,b   Ruan, Xiao ^a,b   Pan, Cun De ^c   Jiang, De An ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c XINJIANG AGRICULTURAL UNIVERSITY   (China)

Author keywords

Allelopathy; Analysis methods; Mechanisms; Phenolic compounds

Indexed keywords

8 QUINOLINOL; CATECHIN; HERBICIDE; PHENOL DERIVATIVE;

CENTAUREA; ECOSYSTEM; GROWTH, DEVELOPMENT AND AGING; METABOLISM; REVIEW;

CATECHIN; CENTAUREA; ECOSYSTEM; HERBICIDES; OXYQUINOLINE; PHENOLS;

EID: 78650636978     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15128933     Document Type: Review

References (90)

1. Rice, E.L. Allelopathy; Academic Press Inc: Norman, Oklahoma, 1984.
2. Weston, L.A.; Duke, S.O. Weed and crop allelopathy. Plant Sci. 2003, 22, 367-389.
3. Zeng, R.S.; Mallik, A.U.; Luo, S.M. Allelopathy in Sustainable Agriculture and Forestry; Springer Science+Business Media, LLC: New York, NY, USA, 2008.
4. Molisch, H. Der Einfluss einer Pflanze auf die andere-Allelopathie; Fischer: Jena, Austria 1937.
5. Singh, H.P.; Kohli, R.K.; Batish, D.R. Allelopathy in agroecosystems: An overview. J. Crop Prod. 2001, 4, 1-41.
6. Callaway, R.M.; Aschehoug, E.T. Invasive plants versus their new and old neighbors: A mechanism for exotic plant invasion. Science 2000, 290, 521-523.
7. Ridenour, W.M.; Callaway, R.M. The relative importance of allelopathy in interference: The effects of an invasive weed on a native bunchgrass. Oecologia 2001, 126, 444-450.
8. Haribal, M.; Enwick, J.A.A. Isovitexin 6-O-β-D-glucopyranoside: A feeding deterrent to Pieris napi oleracea from Alliaria petiolata. Phytochemistry 1998, 47, 1237-1240.
9. Wang, Q.; Ruan, X.; Li, Z.H.; Pan, C.D. Autotoxicity of plants and research of coniferous forest autotoxicity. Sci. Sil. Sin. 2006, 43, 134-142.
10. Capasso, R. The chemistry, biotechnology and ecotoxicology of the polyphenols naturally occurring in vegetable wastes. Curr. Topics Phytochem. 1997, 1, 145-156.
11. Capasso, R.; Cristinzio, G.; Evidente, A.; Scognamiglio, F. Isolation, spectroscopy and selective phytotoxic effects of polyphenols from vegetable waste waters. Phytochemistry 1992, 31, 4125-4128.
12. Hartmann, T. Diversity and variability of plant secondary metabolism: A mechanistic view. Entomol. Gen. Appl. 1996, 80, 177-188.
13. Franz, H. Secondary Metabolites as Plant Traits: Current Assessment and Future Perspectives. Plant Sci. 2002, 21, 273-322.
14. Santana, C.M.; Ferrera, Z.S.; Padrón, M.E.T.; Rodríguez, J.J.S. Methodologies for the extraction of phenolic compounds from environmental samples: New Approaches. Molecules 2009, 14, 298-320.
15. Chou, C.H.; Leu, L.L. Allelopathic substances and interactions of Delonix regia (BOJ) RAF. J. Chem. Ecol. 1992, 18, 2285-2303.
16. Chou, C.H.; Lin, H.J. Autointoxication mechanism of Oryza sativ I. Phytotoxic effects of decomposing rice residues in soil. J. Chem. Ecol. 1976, 2, 353-367.
17. Chou, C.H.; Muller, C.H. Allelopathic mechanisms of Arctostaphylos glandulosa var. zacaensis. Am. Midl. Nat. 1972, 88, 34-347.
18. Chou, C.H.; Lee, Y.Y. Allelopathic dominance of Miscanthus transmorrisonensis in an alpine grassland community in Taiwan. J. Chem. Ecol. 1991, 17, 2267-2281.
19. Tang, C.S. Continuous trapping techniques for the study of allelochemicals from higher plants. In The Science of Allelopathy; Putnam, A.R., Tang, C.S., Eds.; Wiley: New York, NY, 1986; pp. 113-131.
20. Waller, G.R. Atlelochemicals: Role in Agriculture and Forestry. In ACS Symposium Series 330; American Chemical Society: Washington, DC, USA, 1987; p. 606.
21. Batish, D.R.; Kaur, S.; Singh, H.P.; Kohli, R.K. Role of root-mediated interactions in phytotoxic interference of Ageratum conyzoides with rice (Oryza sativa). Flora 2008, 204, 388-395.
22. Mahall, B.E.; Callaway R.M. Root communication mechanisms and intercommunity distributions of 2 mojave desert shrubs. Ecology 1992, 73, 2145-2151.
23. Ghafar, A.; Saleem, B.; Qureshi, M.J. Allelopathic effects of sunflower on germination and seedling growth of wheat. Pak. J. Biol. Sci. 2000, 3, 1301-1302.
24. Sasikumar, K.; Vijayalakshmi, C.; Parthiban, K.T. Allelopathic effects of Eucalyptus on blackgram (Phaseolus mungo L.). Allelopathy J. 2002, 9, 205-214.
25. Willis, R.J. The historical bases of the concept of allelopathy. J. Hist. Biol. 1985, 18, 71-102.
26. Hostettmann, K.; Marston, A.; Hostettmann, M. Preparative Chromatography Techniques: Application in Natural Product Isolation; Springer: Berlin, Germany, 1997.
27. Djurdjevic, L.; Mitrovic, M.; Pavlovic, P. Methodology of allelopathy research: 2. Forest ecosystems. Allelopathy J. 2007, 20, 1-24.
28. Putnam, A.R.; Tang, C.S. The science of Allelopathy; Wiley: New York, NY, USA, 1986; pp. 1-19.
29. Schmidt, S.K. Ecological implications of the destruction of juglone (5-hydroxy-1,4-naphthoquinone) by soil bacteria. J. Chem. Ecol. 1990, 16, 3547-3549.
30. Wu, H.; Haig, T.; Pratley, J.; Lemerle, D.; An, M. Allelochemicals in wheat (Triticum aestivum L.): Production and exudation of 2,4-dihydroxy-7- methoxy-1,4- benzoxazin-3-one. J. Chem. Ecol. 2001, 27, 1691-1700. (Pubitemid 32734768)
31. Inderjit. Plant phenolics in allelopathy. Bot. Rev. 1996, 62, 186-202.
32. Hadacek, F. Secondary metabolites as plant traits: Current assessment and future perspectives. Crit. Rev. Plant Sci. 2002, 21, 273-322.
33. Liebler, D.C.; Burr, J.A.; Philips, L.; Ham, A.J.L. Gas chromatography-mass spectrometry analysis of vitamin E and its oxidation products. Anal. Biochem. 1996, 263, 27-34.
34. Durant, A.A.; Fente, C.A.; Franco, C.M.; Vazquez, B.I.; Cepeda, A. Gas-chromatography-tandem mass spectrometry determination of 17 a-ethinylestradiol residue in the hair of cattle, application to treated animals. J. Agric. Food Chem. 2002, 50, 436-440.
35. Van Pelt, C.D.; Haggarty, H.; Brenna, J.T. Quantitative subfemtomole analysis of a-tocopherol and deuterated isotopomers in plasma using tabletop GC/MS/MS. Anal. Chem. 1998, 70, 4369-4375.
36. Seal, A.N.; Pratley, J.E.; Haig, T; An, M. Identification and quantitation of compounds in a series of allelopathic and non-allelopathic rice root exudates. J. Chem. Ecol. 2004, 30, 1647-1662.
37. Politycka, B. Free and glucosylated phenolics, phenol-beta- glucosyltransferase activity and membrane perability in cucumber roots affected by derivatives of cinnamic and benzoic acid. Acta Physiol. Plantarum. 1997, 19, 311-317.
38. Cruz, O.R.; Anaya, A.L.; Hernandez-Bautista, B.E. Effects of allelochemical stress produced by sicyosdeppei on seedling root ultrastructure of Phaseolous valgaris and Cucubita ficifolia. J. Chem. Ecol. 1998, 24, 2039-2057.
39. Li, H.H.; Inoue, M.; Nishimura, H; Mizutani, J.; Tsuzuki, E. Interaction of trans-cinnamic acid, its related phenolic allelochemicals, and abscisic-acid in seedling growth and seed-germination of lettuce. J. Chem. Ecol. 1993, 19, 1775-1787.
40. Patterson, D.T. Effects of allelopathic chemicals on growth and physiological response of soybean(Glycine max).Weed Sci. 1981, 29, 53-58.
41. Yu, J.Q.; Ye, S.F.; Zhang, M.F.; Hu, W.H. Effects of root exudates and aqueous root extracts of cucumber (Cucumis sativus) and allelochemicals, on photosynthesis and antioxidant enzymes in cucumber. Biochem. Syst. Ecol. 2003, 31, 129-139.
42. Rice, E.L. Allelopathy; Academic Press: New York, NY, USA, 1974; p. 353.
43. Politycka, B. Phenolics and the activities of phenylalanine ammonia-1yase, phenol-beta-glucosyltransferase and beta-glucosidase in cucumber roots as affected by phenolic allelochemicals. Acta Physiol. Plantarum. 1998, 20, 405-410.
44. Batish, D.R.; Singh, H.P.; Kaur, S.; Kohli, R.K.; Yadav, S.S. Caffeic acid affects early growth, and morphogenetic response of hypocotyl cuttings of mung bean (Phaseolus aureus). J. Plant Physiol. 2008, 165, 297-305.
45. Devi, S.R. Effects of ferulic acid on growth and hydrolytic enzyme activities of germinating maize seeds. J. Chem. Ecol. 1992, 18, 1981-1990.
46. He, H.Q.; Lin, W.X. Studies on allelopathic physiobiochemical characteristics of rice. Chin. J. Eco-Agric. 2001, 9, 56-57.
47. Zeng, R.S.; Luo, S.M.; Shi, Y.H. Physiological and biochemical mechanism of allelopathy of secalonic acid on higher plants. Agron. J. 2001, 93, 72-79.
48. Leslie, C.A. Romani R.J. Inhibition of ethylene biosynthesis by salicylic acid. Plant Physiol. 1998, 88, 833-837.
49. Ni, H.W. Present status and prospect of crop allelopathy in China. In Rice Allelopathy; Kim, K.U.; Shin, D.H., Eds. Kyunpook National University: Kyungpook, Korea, 2000; pp. 41-48.
50. Einhellig, F.A.; Galindo, J.C.G.; Molinillo, J.M.G.; Cutler, H.G. Mode of allelochemical action of phenolic compounds. In Allelopathy: Chemistry and Mode of Action of Allelochemicals; CRC Press: Boca Raton, FL, USA, 2004; pp. 217-238.
51. Watson, A.K.; Renney, A.J. The biology of Canadian weeds. 6. Centaurea diffusa and Centaurea maculosa. Can. J. Plant Sci. 1974, 54, 687-701.
52. Tyser, R.W.; Key, C.H. Spotted knapweed in natural area fescue grasslands: An ecological assessment. Northwest Sci. 1988, 62, 981-987.
53. Callaway, R.M.; Ridenour W.M. Novel weapons: Invasive success and the evolution of increased competitive ability. Front. Ecol. Environ. 2004, 2, 436.
54. Bais, H.P.; Walker, T.S.; Stermitz, F.R.; Hufbauer, R.A.; Vivanco, J.M. Enantiomeric-dependent phytotoxic and antimicrobial activity of (±)-catechin. A rhizosecreted racemic mixture from spotted knapweed. Plant Physiol. 2002, 128, 1173-1179.
55. Bais, H.P.; Vepachedu, R.; Gilroy, S.; Callaway, R.M.; Vivanco, J M. Allelopathy and exotic plant invasion: From molecules and genes to species interactions. Science 2003, 301, 1377-1380.
56. Perry, L.G.; Thelen, G.C.; Ridenour, W.M.; Weir, T.L.; Callaway, R.M.; Paschke, M.W.; Vivanco, J.M. Dual role for an allelochemical (±)-catechin from Centaurea maculosa root exudates regulates conspecific seedling establishment. J. Ecol. 2005, 93, 1126-1135.
57. Thelen, G.C.; Vivanco, J.M.; Newingham, B.; Good, W.; Bais, H.P.; Landers, P.; Caesar, A.; Callaway, R.M. Insect herbivory stimulates allelopathic exudation by an invasive plant and the suppression of natives. Ecol. Lett. 2005, 8, 209-217.
58. Weir, T.L.; Bais, H.P.; Stull, V.J.; Callaway, R.M.; Thelen, G.C.; Ridenour, W.M.; Bhamidi, S.; Stermitz, F. R.; Vivanco, J. M. Oxalate contributes to the resistance of Gaillardia grandiflora and Lupinus sericeus to a phytotoxin produced by Centaurea maculosa. Planta 2006, 223, 785-795.
59. Weir, T.L.; Bais, H.P.; Vivanco, J.M. Intraspecific and interspecific interactions mediated by a phytotoxin, (-)-catechin, secreted by the roots of Centaurea maculosa (spotted knapweed). J. Chem. Ecol. 2003, 29, 2379-2394.
60. Perry, L.G.; Johnson, C.; Alford, É.R.; Vivanco, J.M.; Paschke, M.W. Screening of grassland plants for restoration after spotted knapweed invasion. Restor. Ecol. 2005, 13, 725-735.
61. Thorpe, A. Biochemical effects of Centaurea maculosa on soil nutrient cycles and plant communities; PhD Dissertation, University of Montana, Missoula, MT, USA, 2006.
62. Blair, A.C.; Hanson, B.D.; Brunk, G.R.; Marrs, R.A.; Westra, P.; Nissen, S.J.; Hufbauer, R.A. New techniques and findings in the study of a candidate allelochemical implicated in invasion success. Ecol. Lett. 2005, 8, 1039-1047.
63. Blair, A.C.; Nissen, S.J.; Brunk, G.R.; Hufbauer, R.A. A lack of evidence for an ecological role of the putative allelochemical (±)-catechin in Centaurea maculosa invasion process. J. Chem. Ecol. 2006, 32, 2327-2331.
64. Duke, S.O.; Blaie, A.C.; Dayan, F.E.; Johnson, R.D.; Meepagala, K.M.; Cook, D.; Bajsa, J. Is (-)-cathchin a novel weapon of Spooted Knapweed (Centaurea stoebe)? J. Chem. Ecol. 2009, 35, 141-153.
65. Tharayil, N.; Bhowmik, P.C.; Xing, B. Bioavailability of allelochemicals as affected by companion compounds in oil matrices. J. Agric. Food Chem. 2008, 56, 3706-3713.
66. Blair, A.C.; Weston, L.A.; Nissen, S.J.; Brunk, G.R.; Hufbauer, R. The importance of analytical techniques in allelopathy studies with the reported allelochemical catechin as an example. Biol. Invasions 2009, 11, 325-332.
67. Furubayashi, A.; Hiradate, S.; Fujii, Y. Role of catechol structure in the adsorption and transformation reactions of L-DOPA in soils. J. Chem. Ecol. 2007, 33, 239-250.
68. Inderjit.; Pollock, J.; Callaway, R.M.; Hoben, W. Phytotoxic effects of (±)-catechin in vitro, in soil, and in the field. Plos One 2008, 3, 1-11.
69. Vivanco, J.M.; Bais, H.P.; Stermitz, F.R.; Thelen, G.C.; Callaway, R.M. Biogeographical variation in community response to root allelochemistry: Novel weapons and exotic invasion. Ecol. Lett. 2004, 7, 285-292.
70. Norton, A.P.; Blair, A.C.; Hardin, J.G.; Nissen, S.J.; Brunk, G.R. Herbivory and novel weapons: No evidence for enhanced competitive ability or allelopathy induction of Centaurea diffusa by biological controls. Biol. Invasions 2008, 10, 79-88.
71. Romagni, J.G.; Allen, S.N.; Dayan, F.E. Allelopathic effects of volatile cineoles on two weedy plant species. J. Chem. Ecol. 2000, 26, 303-313.
72. Duke, S.O.; Dayan, F.E.; Hernández, A.; Duke, M.V.; Abbas, H.K. Natural products as leads for new herbicide modes of action. In Proceedings Brighton Crop Protection Conference-Weeds, Brighton, UK, 17-20 November, British Crop Protection Council, Brighton, UK, 1997; pp. 579-586.
73. Rimando, A.M.; Olofsdotter, M.; Dayan, F.E.; Duke, S.O. Searching for Rice Allelochemicals. Agron. J. 1999, 93, 16-20.
74. Nakano, H.; Fujii, Y.; Suzuki, T.; Yamada, K.; Kosemura, S.S.; Yamamura, S.; Suzuki, T.; Hasegawa, K.A growth-inhibitory substance exuded from freeze-dried mesquite (Prosopis juliflora (Sw.) DC.) leaves. Plant Growth Regul. 2001, 33, 165-168.
75. Iqbal, Z.; Hiradate, S.; Noda, A.; Fujii, Y. Allelopathic activity of buckwheat: Isolzation and characterization of phenolics. Weed Sci. 2003, 51, 657-662.
76. Shiraishi, S.; Watanabe, I.; Kuno, K.; Fujii, Y. Evaluation of the allelopathic activity of five Oxalidaceae cover plants and the demonstration of potent weed suppression by Oxalis species. Weed Biol. Manag. 2005, 5, 128-136.
77. Parvez, M.M.; Tomita-Yokotani, K.; Fujii, Y.; Konishi, T.; Iwashina, T. Effects of quercetin and its seven derivatives on the growth of Arabidopsis thaliana and Neurospora crassa. Biochem. Syst. Ecol. 2004, 32, 631-635.
78. Inderjit; Callaway, R.M.; Experimantal designs for the study of allelopathy. Plant Soil. 2003, 256, 1-11.
79. Inderjit; Kaur, M.; Foy, C.L. On the significance of field studies in allelopathy. Weed Technol. 2001, 15, 792-797.
80. Ai Hamdi, B.; Inderjit; Olofsdotter, M.; Streibig, J.C. Laboratory bioassay for phytotoxicity: An example from wheat straw. Agron J. 2001, 93, 43-48.
81. Yu, J.Q.; Matsui,Y. Effects of root exudates of cucumber (Cucumis sativus.) and allelochemicals on ion uptake by cucumber seedlings. J. Chem. Ecol. 1997, 23, 817-827.
82. Yu, J.Q.; Matsui,Y. Phytotoxic substances in root exudates of cucumber (Cucumis sativus L.). J. Chem. Ecol. 1994, 20, 21-31.
83. Ye, S.F.; Zhou, Y.H.; Sun, Y.; Zou, L.Y.; Yu, J.Q. Cinnamic acid causes oxidative stress in cucumber roots, and promotes incidence of Fusarium wilt. Environ. Exp. Bot. 2006, 56, 255-262.
84. Luo, X.; Pan, C.D.; Huang, M.M.; Liu, C.L. Autotoxicity of Picea schrenkiana litter aqueous extracts on seed germination and seedling growth. Xinjiang Agr. Sci. 2006, 43, 1-5.
85. Wang, Q.; Ruan, X.; Pan, C.D;, Xu, N.Y.; Luo, X.; Huang, M.M. Need for sustainability policy-A case study of the National Forest Conservation Program (NFCP) in the western region of Tianshan Mountain, China. Forest. Chron. 2006, 82, 31-39.
86. Appel, H.M. Phenolics in ecological interactions: The importance of oxidation. J. Chem. Ecol. 1993, 19, 1521-1552.
87. Blum, U. Allelopathic interactions involving phenolic acids. J. Nematol. 1996, 28, 259-267.
88. Blum, U.; Dalton, B.R. Effects of ferulic acid, an allelopathic compound on leaf expansion of cucumber seedlings in nutrient culture. J. Chem. Ecol. 1985, 11, 279-301.
89. Blum, U.; Shafer, S.R. Microbial populations and phenolic acids in soil. Soil Biol. Biochem. 1988, 20, 793-800.
90. Blum, U. Effects of microbial utilization of phenolic acids and their phenolic acid breakdown products on allelopathic interactions. J. Chem. Ecol. 1998, 24, 685-708.