Phytotoxic action mechanism of hapalocyclamide in lettuce seedlings

Plant Physiology and Biochemistry

Volumn 58, Issue , 2012, Pages 23-28

  Koodkaew, Intira ^a   Sunohara, Yukari ^a   Matsuyama, Shigeru ^a   Matsumoto, Hiroshi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Cell death; Hapalocyclamide; Hapalosiphon sp.; Lipid peroxidation; Mitosis; Reactive oxygen species

Indexed keywords

CYCLO THIAZOLE ALANINE OXAZOLE ALANINE THIAZOLINE PHENYLALANINE; CYCLO-THIAZOLE-ALANINE-OXAZOLE-ALANINE-THIAZOLINE-PHENYLALANINE; CYCLOPEPTIDE; REACTIVE OXYGEN METABOLITE; THIAZOLE DERIVATIVE;

ARTICLE; CELL DEATH; CELL MEMBRANE; CELL SURVIVAL; CHEMISTRY; CYANOBACTERIUM; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; LETTUCE; LIPID METABOLISM; METABOLISM; MITOSIS; OXIDATIVE STRESS; PLANT; PLANT ROOT; SEEDLING;

CELL DEATH; CELL MEMBRANE; CELL SURVIVAL; CYANOBACTERIA; LETTUCE; LIPID METABOLISM; MITOSIS; OXIDATIVE STRESS; PEPTIDES, CYCLIC; PLANT ROOTS; PLANT SHOOTS; REACTIVE OXYGEN SPECIES; SEEDLING; THIAZOLES;

HAPALOSIPHON; LACTUCA; LACTUCA SATIVA;

EID: 84863484072     PISSN: 09819428     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.plaphy.2012.06.002     Document Type: Article

References (42)

1. Prasanna R., Sood A., Jaiswal P., Nayak S., Gupta V., Chaudhary V., Joshi M., Natarajan C. Rediscovering cyanobacteria as valuable sources of bioactive compounds (review). Appl. Biochem. Microbiol. 2010, 46:119-134.
2. Smith G.D., Doan N.T. Cyanobacterial metabolites with bioactivity against photosynthesis in cyanobacteria, algae and higher plants. J. Appl. Phycol. 1999, 11:337-344.
3. Burja A.M., Banaigs B., Abou-Mansour E., Burgess J.G., Wright P.C. Marine cyanobacteria-a prolific source of natural products. Tetrahedron 2001, 57:9347-9377.
4. Nunnery J.K., Mevers E., Gerwick W.H. Biologically active secondary metabolites from marine cyanobacteria. Curr. Opin. Biotechnol. 2010, 21:787-793.
5. MacKintosh C., Beattie K.A., Klumpp S., Cohen P., Codd G.A. Cyanobacterial microcystin-LR is a potent and specific inhibitor of protein phosphatases 1 and 2A from both mammals and higher plants. FEBS Lett. 1990, 264:187-192.
6. Chen J., Song L., Dai J., Gan N., Liu Z. Effects of microcystins on the growth and the activity of superoxide dismutase and peroxidase of rape (Brassica napus L.) and rice (Oryza sativa L.). Toxicon 2004, 43:393-400.
7. Kurki-Helasmo K., Meriluoto J. Microcystin uptake inhibits growth and protein phosphatase activity in mustard (Sinapsis alba L.) seedlings. Toxicon 1998, 12:1921-1926.
8. M-Hamvas M., Máthé C., Molnár E., Vasas G., Grigorszky I., Borbely G. Microcystin-LR alters the growth, anthocyanin content and single-stranded DNase enzyme activities in Sinapis alba L. seedlings. Aquat. Toxicol. 2003, 62:1-9.
9. Welker M., Döhren H. Cyanobacterial peptides - nature's own combinatorial biosynthesis. FEMS Microbiol. Rev. 2006, 30:530-563.
10. Sivonen K., Leikoski N., Fewer D.P. Cyanobactins-ribosomal cyclic peptides produced by cyanobacteria. Appl. Microbiol. Biot. 2010, 86:1213-1225.
11. Carmichael W.W. Cyanobacterial secondary metabolites-the cyanotoxins. J. Appl. Bacteriol. 1992, 72:445-459.
12. Hu Z., Liu Y., Li D., Dauta A. Growth and antioxidant system of the cyanobacterium Synechococcus elongatus in response to microcystin-RR. Hydrobiologia 2005, 534:23-29.
13. Gehringer M.M., Kewada V., Coates N., Downing T.G. The use of Lepidium sativum in a plant bioassay system for the detection of microcystin-LR. Toxicon 2003, 41:871-876.
14. Peuthert A., Chakrabarti S., Pflugmacher S. Uptake of microcystins-LR and -LF (cyanobacterial toxins) in seedlings of several important agricultural plant species and the correlation with cellular damage (lipid peroxidation). Environ. Toxicol. 2007, 22:436-442.
15. Moore R.E., Cheuk C., Yang X.Q.G., Patterson G.M.L. Hapalindoles, antibacterial and antimycotic alkaloids from the cyanophyte Hapalosiphon fontinalis. J. Org. Chem. 1987, 52:1036-1043.
16. Moore R.E., Yang X.Q.G., Patterson G.M.L. Fontonamide and anhydrohapaloxindole A, two new alkaloids from the blue-green alga Hapalosiphon fontinalis. J. Org. Chem. 1987, 52:3733-3777.
17. Stratmann K., Moore R.E., Bonjouklian R., Deeter J.B., Patterson G.M.L., Shaffer S., Smith C.D., Smitka T.A. Welwitindolinones, unusual alkaloids from the blue-green algae Hapalosiphon welwitschii and Westiella intricate. Relationship to fischerindoles and hapalindoles. J. Am. Chem. Soc. 1994, 116:9935-9942.
18. Stratmann K., Burgoyne D.L., Moore R.E., Patterson G.M.L. Hapalosin, a cyanobacterial cyclic depsipeptide with multidrug-resistance reversing activity. J. Org. Chem. 1994, 59:7219-7226.
19. Smitka T.A., Boujouklian R., Doolin L., Jones N.D., Deeter J.B. Ambiguine isonitriles, fungicidal hapalindole-type alkaloids from three genera of blue-green algae belonging to the Stigonemataceae. J. Org. Chem. 1992, 57:857-861.
20. Prinsep M.R., Caplan F.R., Moore R.E., Patterson G.M.L., Honkanen R.E., Boynton A.L. Microcystin-LA from a blue green alga belonging to the Stigonematales. Phytochemistry 1992, 31:1247-1248.
21. Sanevas N., Sunohara Y., Matsumoto H. Crude extract of the cyanobacterium, Hapalosiphon sp., causes a cessation of root elongation and cell division in several plant species. Weed Biol. Manag. 2006, 6:25-29.
22. Sanevas N., Sunohara Y., Matsumoto H. Characterization of reactive oxygen species-involved oxidative damage in Hapalosiphon species crude extract-treated. Weed Biol. Manag. 2007, 7:172-177.
23. Koodkaew I., Matsuyama S., Sunohara Y., Matsumoto H. Hapalocyclamide: a novel hexapeptide of the cyanobacterium Hapalosiphon sp. Tetrahedron Lett. 2012, 53:977-979.
24. Planchais S., Glab N., Inźe D., Bergounioux C. Chemical inhibitors: a tool for plant cell cycle studies. FEBS Lett. 2000, 476:78-83.
25. Chen X., Smith G.D., Waring P. Human cancer cell (Jurket) killing by the cyanobacterial metabolite calothrixin A. J. Appl. Phycol. 2003, 15:269-277.
26. Reichheld J.-P., Vernoux T., Lardon F., Montagu M.V., Inzé D. Specific checkpoints regulate plant cell cycle progression in response to oxidative stress. Plant J. 1999, 17:647-656.
27. Baker C.J., Mock N.M. An improved method for monitoring cell death in cell suspension and leaf disc assays using Evans blue. Plant Cell Tissue Organ. Cult. 1994, 39:7-12.
28. Gaff D.F., Okong'o-Ogola O. The use of non-permeating pigments for testing the survival of cells. J. Exp. Bot. 1971, 22:756-758.
29. Overmyer K., Brosche M., Kangasjärvi J. Reactive oxygen species and hormonal control of cell death. TRENDS Plant Sci. 2003, 8:335-342.
30. Morel J.B., Dangl J.L. The hypersensitive response and the induction of cell death in plants. Cell Death Differ. 1997, 4:671-683.
31. Gechev T.S., Breusegem F.V., Stone J.M., Denev I., Laloi C. Reactive oxygen species as signals that modulate plant stress responses and programmed cell death. BioEssays 2006, 28:1091-1101.
32. Babula P., Adam V., Kizek R., Sladky Z., Havel L. Naphthoquinones as allelochemical triggers of programmed cell death. Environ. Exp. Bot. 2009, 65:330-337.
33. Garnczarska M. Response of the ascorbate-glutathione cycle to re-aeration following hypoxia in lupine roots. Plant Physiol. Biochem. 2005, 43:583-590.
34. Sunohara Y., Shirai S., Yamazaki H., Matsumoto H. Involvement of antioxidant capacity in quinclorac tolerance in Eleusine indica. Environ. Exp. Bot. 2011, 74:74-81.
35. Katsuhara M., Otsuka T., Ezaki B. Salt stress-induced lipid peroxidation is reduced by glutathione S-transferase, but this reduction of lipid peroxides is not enough for a recovery of root growth in Arabidopsis. Plant Sci. 2005, 169:369-373.
36. Gutteridge J.M.C. Lipid peroxidation and anoxidants as biomarkers of tissue damage. Clin. Chem. 1995, 41/42:1819-1828.
37. Bolwell G.P., Bindschedler L.V., Blee K.A., Butt V.S., Davies D.R., Gardner S.L., Gerrish C., Minibayeva F. The apoplastic oxidative burst in response to biotic stress in plants: a three-component system. J. Exp. Bot. 2002, 53:1367-1376.
38. Hao F., Wang X., Chen J. Involvement of plasma-membrane NADPH oxidase in nickel-induced oxidative stress in roots of wheat seedlings. Plant Sci. 2006, 170:151-158.
39. 2 by Phytophthora elicitor-stimulated rose cells. Plant Physiol. 1995, 107:1241-1247.
40. Richmond A. Handbook of Microalgal Mass Culture 1986, CRC Press, Florida.
41. Sunohara Y., Matsumoto H. Quinclorac-induced cell death is accompanied by generation of reactive oxygen species in maize root tissue. Phytochemistry 2008, 69:2312-2319.
42. Velikova V., Yordanov I., Edreva A. Oxidative stress and some antioxidant systems in acid rain-treated bean plants: protective role of exogenous polyamines. Plant Sci. 2000, 151:59-66.