Isolation of phytotoxic compounds from tree-of-heaven (Ailanthus altissima swingle)

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 5, 2003, Pages 1177-1180

  De Feo, Vincenzo ^a   De Martino, Laura ^a   Quaranta, Emilia ^a   Pizza, Cosimo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

Ailanthone; Ailanthus altissima; Allelopathic activity; Natural herbicides; Quassinoids; Tree of heaven

Indexed keywords

AILANTHINOL B; AILANTHINONE; AILANTHONE; AILANTHUS ALTISSIMA EXTRACT; CHAPARRINE; HERBICIDE; PLANT EXTRACT; QUASSINOID DERIVATIVE; UNCLASSIFIED DRUG;

AILANTHUS; AILANTHUS ALTISSIMA; ARTICLE; BIOASSAY; CHEMICAL COMPOSITION; CHEMISTRY; CHROMATOGRAPHY; CONCENTRATION RESPONSE; DRUG EFFECT; EXTRACTION; GERMINATION; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; LEPIDIUM; NONHUMAN; PHYTOTOXICITY; PLANT ROOT; PLANT SEED; PORTULACA; PURIFICATION; RADISH;

AILANTHUS; BIOLOGICAL ASSAY; GERMINATION; HERBICIDES; LEPIDIUM; PLANT EXTRACTS; PLANT ROOTS; PORTULACA; QUASSINS; RAPHANUS; SEEDS;

AILANTHUS; AILANTHUS ALTISSIMA; LEPIDIUM; LEPIDIUM SATIVUM; PORTULACA; PORTULACA OLERACEA; PORTULACACEAE; RAPHANUS SATIVUS;

EID: 0037467088     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020686+     Document Type: Article

References (55)

1. Rice, E. L. Allelopathy, 2nd ed.; Academic Press: New York, 1984 and references therein.
2. De Feo, V.; De Simone, F.; Senatore, F. Potential allelochemicals from the essential oil of Ruta graveolens. Phytochemistry 2002. 61, 573-578 and references therein.
3. Shah, B. The checkered career of Ailanthus altissima. Arnoldia 1997, 57, 21-27.
4. Casinovi, G. C.; Ceccherelli, P.; Fardella, G.; Grandolini, G. Isolation and structure of a quassinoid from Ailanthus glandulosa. Phytochemistry 1983, 22, 2871-2873 and references therein.
5. Chiarlo, B.; Pinca, M. C. Ricerche sui costituenti della corteccia di Ailanthus glandulosa Desf. subspontaneo in Liguria. I. Identificazione di due amaroidi. Boll. Chim. Farm. 1965, 104, 485-489.
6. Furuno, T.; Naora, H.; Murae, T.; Hirota, H.; Tsuyuki, T.; Takahashi, T.; Itai, A.; Iitaka, Y.; Matsushita, K. Structure of shinjulactone B, a new bitter principle from Ailanthus altissima. Chem. Lett. 1981, 12, 1597-1598.
7. Niimi, Y.; Tsuyuki, T.; Takahashi, T.; Matsushita, K. Bitter principles of Ailanthus altissima Swingle. Structure determination of shinjuglycosides E and F. Chem. Pharm. Bull. 1987, 35, 4302-4306 and references therein.
8. Kubota, K.; Fukamiya, N.; Hamada, T.; Okano, M.; Tagahara, K.; Lee, K.-H. Two New Quassinoids, Ailantinols A and B, and Related Compounds from Ailanthus altissima. J. Nat. Prod. 1996, 59, 683-686.
9. Ohmoto, T.; Koike, K.; Sakamoto, Y. Studies on the constituents of Ailanthus altissima Swingle. II. Alkaloidal constituents. Chem. Pharm. Bull. 1981, 29, 390-395 and references therein.
10. Varga, E.; Szendrei, K.; Reisch, J.; Maroti, G. Indole alkaloids of Ailanthus altissima. II. Fitoterapia 1981, 52, 183-186 and references therein.
11. Oomoto, T.; Koike, K. Studies on the constituents of Ailanthus altissima Swingle. III. The alkaloidal constituents. Chem. Pharm. Bull. 1984, 32, 170-173.
12. Souleles, C.; Waigh, R. Indole alkaloids of Ailanthus altissima. J. Nat. Prod. 1984, 47, 741.
13. Souleles, C.; Kokkalou, E. A new β-carboline alkaloid from Ailanthus altissima. Planta Med. 1989, 55, 286-287.
14. Chiarlo, B.; Tacchino, E. Constituents of the bark of Ailanthus altissima. II. Content of fatty acids to C22. Riv. Ital. Sostanze Grasse 1965, 42, 122-124.
15. Bory, G.; Clair-Maezulajtys, D. Lipid content and fatty acid composition of seeds of Ailanthus altissima (Mill.) Swingle (Simaroubaceae). Indian J. Plant Physiol. 1989, 32, 12-16; Chem. Abstr. 1991, 115, 89072.
16. Bory, G.; Clair-Maezulajtys, D. Lipid content and fatty acid composition of seeds of Ailanthus altissima (Mill.) Swingle (Simaroubaceae). Indian J. Plant Physiol. 1989, 32, 12-16; Chem. Abstr. 1991, 115, 89072.
17. Kapoor, N.; Bedi, K. L.; Tikoo, M. K.; Kapoor, S. K.; Sarin, Y. K. Some lesser known tree-borne oilseeds of India. J. Oil Technol. Assoc. India (Bombay) 1990, 22, 65-66; Chem. Abstr. 1991, 115, 110549.
18. Kapoor, N.; Bedi, K. L.; Tikoo, M. K.; Kapoor, S. K.; Sarin, Y. K. Some lesser known tree-borne oilseeds of India. J. Oil Technol. Assoc. India (Bombay) 1990, 22, 65-66; Chem. Abstr. 1991, 115, 110549.
19. Kucuk, M, M.; Demirbas, A.; Ayas, A. Fatty acids of Ailanthus altissima. Modell., Meas. Control, C 1994, 46, 45-48; Chem. Abstr. 1995, 123, 115790.
20. Kucuk, M, M.; Demirbas, A.; Ayas, A. Fatty acids of Ailanthus altissima. Modell., Meas. Control, C 1994, 46, 45-48; Chem. Abstr. 1995, 123, 115790.
21. Souleles, C.; Philianos, S. Constituents of Ailanthus glandulosa leaves. Plant. Med. Phytother. 1983, 17, 157-160.
22. Barakat, H. H. Chemical investigation of the constitutive phenolics of Ailanthus altissima; the structure of a new flavone glycoside gallate. Nat. Prod. Sci. 1998, 4, 153-157.
23. El-Baky, A. M.; Darwish, F. M.; Ibraheim, Z. Z.; Gouda, Y. G. Phenolic compounds from Ailanthus altissima Swingle. Bull. Pharm. Sci., Assiut Univ. 2000, 23, 111-116; Chem. Abstr. 2001, 134, 307890.
24. El-Baky, A. M.; Darwish, F. M.; Ibraheim, Z. Z.; Gouda, Y. G. Phenolic compounds from Ailanthus altissima Swingle. Bull. Pharm. Sci., Assiut Univ. 2000, 23, 111-116; Chem. Abstr. 2001, 134, 307890.
25. Mastelic, J.; Jerkovic, I. Volatile constituents from the leaves of young and old Ailanthus altissima (Mill.) Swingle tree. Croat. Chem. Acta 2002, 75, 189-197; Chem. Abstr. 2002, 136, 298362.
26. Mastelic, J.; Jerkovic, I. Volatile constituents from the leaves of young and old Ailanthus altissima (Mill.) Swingle tree. Croat. Chem. Acta 2002, 75, 189-197; Chem. Abstr. 2002, 136, 298362.
27. Hwang, S.-G.; Lee, H. C.; Kim, C. K.; Kim, D. G.; Lee, G. O.; Yun, Y. G.; Jeon, B. H. Effect of Ailanthus altissima water extract on cell cycle control genes in Jurkat T lymphocytes. Yakhak Hoechi 2002, 46, 18-23; Chem. Abstr. 2002, 136, 182902.
28. Hwang, S.-G.; Lee, H. C.; Kim, C. K.; Kim, D. G.; Lee, G. O.; Yun, Y. G.; Jeon, B. H. Effect of Ailanthus altissima water extract on cell cycle control genes in Jurkat T lymphocytes. Yakhak Hoechi 2002, 46, 18-23; Chem. Abstr. 2002, 136, 182902.
29. Crespi-Perellino, N.; Guicciardi, A.; Minghetti, A.; Speroni, E. Comparison of biological activity induced by Ailanthus altissima plant or cell cultures extracts. Pharmacol. Res. Commun. 1988, 20 (Suppl. 5), 45-48.
30. Kraus, W.; Koll-Weber, M.; Maile, R.; Wunder, T.; Vogler, B. Biologically active constituents of tropical and subtropical plants. Pure Appl. Chem. 1994, 66, 2347-2352.
31. Rahman, S.; Fukamiya, N.; Okano, M.; Tagahara, K.; Lee, K.H. Antitubercolosis activity of quassinoids. Chem. Pharm. Bull. 1997, 45, 1527-1529.
32. Bray, D. H.; Boardman, P.; O'Neill, M. J.; Chan, K. L.; Phillipson, J. D.; Warhurst, D. C.; Suffness, M. Plants as a source of antimalarial drugs. 5. Activities of Ailanthus altissima stem constituents and of some related quassinoids. Phytother. Res. 1987, 1, 22-24.
33. Tamura, S.; Fukamiya, N.; Mou, X.-Y.; Mukainaka, T.; Tokuda, H.; Nishino, H.; Tagahara, K.; Koike, K.; Lee, K.-H.; Okano, M. Conversion of quassinoids for enhancement of inhibitory effect against Epstein-Barr virus early antigen activation. Introduction of lipophilic side chain and esterification of diosphenol. Chem. Pharm. Bull. 2000, 48, 876-878.
34. Ohmoto, T.; Koike, K. Antiherpes activity of Simaroubaceae alkaloids in vitro. Shoyakugaku Zasshi 1988, 42, 160-162; Chem. Abstr. 1989, 110, 111567.
35. Ohmoto, T.; Koike, K. Antiherpes activity of Simaroubaceae alkaloids in vitro. Shoyakugaku Zasshi 1988, 42, 160-162; Chem. Abstr. 1989, 110, 111567.
36. Ohmoto, T.; Sung, Y. 1. Antimycotic substances in the crude drugs. II. Shoyakugaku Zasshi 1982, 36, 307-314; Chem. Abstr. 1983, 98, 204263.
37. Ohmoto, T.; Sung, Y. 1. Antimycotic substances in the crude drugs. II. Shoyakugaku Zasshi 1982, 36, 307-314; Chem. Abstr. 1983, 98, 204263.
38. Ohmoto, T.; Sung, Y. I.; Koike, K.; Nikaido, T. Effect of alkaloids of simaroubaceous plants on the local blood flow rate. Shoyakugaku Zasshi 1985, 39, 28-34; Chem. Abstr. 1985, 103. 206469.
39. Ohmoto, T.; Sung, Y. I.; Koike, K.; Nikaido, T. Effect of alkaloids of simaroubaceous plants on the local blood flow rate. Shoyakugaku Zasshi 1985, 39, 28-34; Chem. Abstr. 1985, 103. 206469.
40. Mergen, F. A toxic principle in the leaves of Ailanthus. Bot. Gaz. 1959, 121, 32-36.
41. Voigt, G. K.; Mergen, F. Seasonal variation in toxicity of ailanthus leaves to pine seedlings. Bot. Gaz. 1962, 123, 262-265.
42. Heisey, R. M. Evidence for allelopathy by tree-of-heaven (Ailanthus altissima). J. Chem. Ecol. 1990, 16, 2039-2055.
43. Heisey, R. M. Allelopathic and herbicidal effects of extracts from tree of heaven (Ailanthus altissima). Am. J. Bot. 1990, 77, 662-670.
44. Heisey, R. M. Allelopathy and the secret life of Ailanthus altissima. Arnoldia 1997, 57, 28-36.
45. Lawrence, J. G.; Colwell, A.; Sexton, O. J. The ecological impact of allelopathy in Ailanthus altissima (Simaroubaceae). Am. J. Bot. 1991, 78, 948-958.
46. Heisey, R. M. Identification of an allelopathic compound from Ailanthus altissima (Simaroubaceae) and characterization of its herbicidal activity. Am. J. Bot. 1996, 83, 192-200.
47. Lin, L.-J.; Peiser, G.; Ying, B.-P.; Mathias, K.; Karasina, F.; Wang, Z.; Itatani, J.; Green, L.; Hwang, Y.-S. Identification of Plant Growth Inhibitory Principles in Ailanthus altissima and Castela tortuosa. J. Agric. Food Chem. 1995, 43, 1708-1711.
48. Heisey, R. M. Potential of ailanthone, an allelochemical from Ailanthus altissima, as a natural-product herbicide. Abstracts of Papers, 214th National Meeting of the American Chemical Society, Las Vegas, NV, September 7-11, 1997; ACS: Washington, DC, 1997; AGRO-037.
49. Heisey, R. M. Development of an allelopathic compound from tree-of-heaven (Ailanthus altissima) as a natural product herbicide. In Biologically Active Natural Products: Agrochemicals; Cutler, H. G., Cutler, S. J., Eds.; CRC: Boca Raton, FL, 1999; pp 57-68.
50. Koike, K.; Ohmoto, T. Carbon-13 magnetic resonance study of canthin-6-one alkaloids. Chem. Pharm. Bull. 1985, 33, 5239-5244.
51. Regnier, E. E.; Janke, R. R. Evolving strategies for managing weeds. In Sustaineble Agricultural Systems: Edwars, C. A., Lal, R., Madden, P., Miller, R. H., House. G., Eds.; St. Lucie Press: Detray Beach, FL, 1994.
52. Fo, E. R.; Fernandes, J. B.; Vieira, P. C.; da Silva, M. F.; Zukerman-Schpector, J.; de Lima Correa, R. M. O.; Nascimento, S. C.; Wait, T. Protolimonoids and quassinoids from Picrolemma granatensis. Phytochemistry 1996, 43, 857-862.
53. European Pharmacopoeia, Vol. 3; Maisonneuve SA: SainteRufine, 1975; p 68.
54. Bewley, D., Black, M. Seeds. Physiology of Development and Germination: Plenum Press: New York, 1985.
55. Narwal, S. S. Allelopathy in Crop Production; Scientific Publishers: Jodhpur, India, 1994.