Phytotoxic effects and a phytotoxin from the invasive plant Xanthium italicum moretti

Molecules

Volumn 17, Issue 4, 2012, Pages 4037-4046

  Shao, Hua ^a   Huang, Xiaoli ^a   Wei, Xiaoyi ^b   Zhang, Chi ^a  

^a XINJIANG INSTITUTE OF ECOLOGY AND GEOGRAPHY   (China)

^b SOUTH CHINA INSTITUTE OF BOTANY   (China)

Author keywords

Allelopathic; Invasive plant; Phytotoxin; Xanthinosin; Xanthium italicum Moretti

Indexed keywords

LACTONE; PLANT EXTRACT; SESQUITERPENE; SOLVENT; XANTHINOSIN;

ARTICLE; ASTERACEAE; CHEMISTRY; DRUG EFFECT; FRUIT; ISOLATION AND PURIFICATION; PLANT; PLANT ROOT; PLANT STEM;

ASTERACEAE; FRUIT; LACTONES; PLANT EXTRACTS; PLANT ROOTS; PLANT SHOOTS; PLANT STEMS; SESQUITERPENES; SOLVENTS;

EID: 84860238206     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17044037     Document Type: Article

References (35)

1. Liu, Q.R.; Yu, M.; Zhou, Y.L. A preliminary study on the invasive plants in Beijing. J. Beijing Normal Univ. (Nat. Sci.) 2002, 38, 399-404.
2. Li, N.; Zhu, L.N.; Zhai, Q.; Zhu, M.W.; Chen, X.H.; Qu, B. A new alien invasive plant-Xanthium italicum Moretti in Liaoning Province. Plant Quar. 2010, 24, 49-52.
3. Wang, R.; Wan, F.H. Prediction of the potential survival area of Xanthium Italicum in China. Acta Pratacult. Sin. 2010, 19, 222-230.
4. Ministry of Agriculture of the People's Republic of China. The Directory of Imported Plant Quarantine Pests of the People's Republic of China. The Ministry of Agriculture Bulletin No. 862 of the People's Republic of China; Beijing, China, 2007.
5. Zhao, J. Physical Geography of China; Higher Education Press: Beijing, China, 1995.
6. Takakura, K.; Fujii, S. Reproductive interference and salinity tolerance differentiate habitat use between two alien cockleburs: Xanthium occidentale and X. italicum (Compositae). Plant Ecol. 2010, 206, 309-319.
7. Vitousek, P.M.; Antonio, C.M.D.; Loop, L.L.; Westbrooks, R. Biological invasions as global environmental change. Am. Sci. 1996, 84, 468-478.
8. Kitayama, K.; Mueller-Dombois, D. Biological invasion on an oceanic island mountain: Do alien plant species have wider ecological ranges than native species? J. Veg. Sci. 1995, 6, 667-674.
9. Goodall, D.W.; Perry, R.A. Arid Land Ecosystems: Volume 2, Structure, Functioning and Management; Cambridge University Press: Cambridge, UK, 2009.
10. Holzmueller, E.; Jose, S. Invasion success of cogongrass, an alien C4 perennial grass, in the southeastern United States: Exploration of the ecological basis. Biol. Invasions 2011, 13, 435-442.
11. 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 spotted knapweed invasion success. J. Chem. Ecol. 2006, 32, 2327-2331.
12. Duke, S.O.; Blair, A.C.; Dayan, F.E.; Johnson, R.D.; Meepagala, K.M.; Cook, D.; Bajsa, J. Is (-)-catechin a novel weapon of spotted knapweed (Centaurea stoebe)? J. Chem. Ecol. 2009, 35, 141-153.
13. Callaway, R.M.; Ridenour, W.M. Novel weapons: Invasive success and the evolution of increased competitive ability. Front. Ecol. Environ. 2004, 2, 436-433.
14. Thorpe, A.S.; Thelen, G.C.; Diaconu, A.; Callaway, R.M. Root exudate is allelopathic in invaded community but not in native community: Field evidence for the novel weapons hypothesis. J. Ecol. 2009, 97, 641-645.
15. Callaway, R.M.; Aschehoug, E.T. Invasive plants versus their new and old neighbors: A mechanism for exotic invasion. Science 2000, 290, 521-523.
16. Yan, J.; Bi, H.H.; Liu, Y.Z.; Zhang, M.; Zhou, Z.Y.; Tan, J.W. Phenolic Compounds from Merremia umbellata subsp. orientalis and their allelopathic effects on Arabidopsis seed germination. Molecules 2010, 15, 8241-8250.
17. Shao, H.; Peng, S.L.; Wei, X.Y.; Zhang, D.Q.; Zhang, C. Potential allelochemicals from an invasive weed Mikania micrantha H.B.K. J. Chem. Ecol. 2005, 31, 1657-1668.
18. Ens, E.J.; Bremner, J.B.; French, K.; Korth, J. Identification of volatile compounds released by roots of an invasive plant, bitou bush (Chrysanthemoides monilifera spp. rotundata), and their inhibition of native seedling growth. Biol. Invasions 2009, 11, 275-287.
19. Xie, L.J.; Zeng, R.S.; Bi, H.H.; Song, Y.Y.; Wang, R.L.; Su, Y.J.; Chen, M.; Chen, S.; Liu, Y.H. Allelochemical mediated invasion of exotic plants in China. Allelopathy J. 2010, 25, 31-50.
20. Bohlmann, F.; Jakupovic, J.; Schuster, A. Further eudesmanolides and xanthanolides from Telekia speciosa. Phytochemistry 1981, 20, 1891-1893.
21. Bohlmann, F.; Mahanta, P.K.; Jakupovic, J.; Rastogi, R.; Natu, A.A. New sesquiterpene lactones from Inula species. Phytochemistry 1978, 17, 1165-1172.
22. Marco, J.A.; Sanz-cervera, J.F.; Corral, J.; Carda, M.; Jakupovic, J. Xanthanolides from Xanthium: Absolute configuration of xanthanol, isoxanthanol and their C-4 epimers. Phytochemistry 1993, 34, 1569-1576.
23. Irving; R.; Huang, Y.; Hickie, R.A.; Sutherland, R.G.; Barl, B. Xanthatin and xanthinosin from the burs of Xanthium strumarium L. as potential anticancer agents. Can. J. Physiol. Pharmacol. 2007, 85, 1160-1172.
24. Lavault, M.; Landreau, A.; Larcher, G.; Bouchara, J.P.; Pagniez, F.; Pape, P.L.; Richomme, P. Antileishmanial and antifungal activities of xanthanolides isolated from Xanthium macrocarpum. Fitoterapia 2005, 76, 363-366.
25. Yoon, J.H.; Lim, H.J.; Lee, H.J.; Kim, H.; Jeon, R.; Ryu, J. Inhibition of lipopolysaccharide-induced inducible nitric oxide synthase and cyclooxygenase-2 expression by xanthanolides isolated from Xanthium strumarium. Bioorg. Med. Chem. Lett. 2008, 18, 2179-2182.
26. Vasas, A.; Hohmann, J. Xanthane sesquiterpenoids: Structure, synthesis and biological activity. Nat. Prod. Rep. 2011, 28, 824-842.
27. Sato, Y.; Oketani, H.; Yamada, T.; Singyouchi, K.; Ohtsubo, T.; Kihara, M.; Higuti, T. A xanthanolide with potent antibacterial activity against methicillin-resistant Staphylococcus aureus. J. Pharm. Pharmacol. 1997, 49, 1042-1044.
28. Favier, L.S.; María, A.O.M.; Wendel, G.H.; Borkowski, E.J.; Giordano, O.S.; Pelzer, L.; Tonn, C.E. Anti-ulcerogenic activity of xanthanolide sesquiterpenes from Xanthium cavanillesii in rats. J. Ethnopharmacol. 2005, 100, 260-267.
29. Kovacs, A.; Vasas, A.; Forgo, P.; Rethy, B.; Zupko, I.; Hohmann, J. Xanthanolides with antitumour activity from Xanthium italicum. Z. Naturforsch. C 2009, 64, 343-349.
30. Tsankova, E.T.; Trendafilova, A.B. Xanthanolides of Xanthium italicum Moretti and their biological activity. Z. Naturforsch. C 1994, 49, 154-155.
31. Geissman, T.A.; Deuel, P.; Bonde, E.K.; Addicott, F.A. Xanthinin: A plant growth-regulating compound from Xanthium pennsylvanicum. J. Am. Chem. Soc. 1954, 76, 685-687.
32. Yokotani-Tomita, K.; Katol, J.; Yamadal, K.; Kosemura, S.; Yamamura, S.; Bruinsma, J.; Hasegawal, K. 8-Epixanthatin, a light-induced growth inhibitor, mediates the phototropic curvature in sunflower (Helianthus annuus) hypocotyls. Physiol. Plant. 1999, 106, 326-330.
33. Leao, N.P.; Pereira, A.R.; Liu, W.; Ng, J.; Pevzner, P.A.; Dorrestein, P.C.; Konig, G.M.; Vasconcelos, V.M.; Gerwick, W.H. Synergistic allelochemicals from a freshwater cyanobacterium. Proc. Natl. Acad. Sci. USA 2007, 107, 11183-11188.
34. Mitchell, G.; Bartlett, D.W.; Fraser, T.E.; Hawkes, T.R.; Holt, D.C.; Townson, J.K.; Wichert, R.A. Mesotrione: A new selective herbicide for use in maize. Pest Manag. Sci. 2001, 57, 120-128.
35. Grayson, B.T.; Williams, K.S.; Freehauf, P.A.; Pease, R.R.; Ziesel, W.T.; Sereno, R.L.; Reinsfelder, R.E. The physical and chemical properties of the herbicide cinmethylin (SD 95481). Pestic. Sci. 1987, 143-153.