Norsesquiterpene glycosides in bracken ferns (Pteridium esculentum and Pteridium aquilinum subsp. wightianum) from eastern Australia: Reassessed poisoning risk to animals

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 9, 2011, Pages 5133-5138

  Fletcher, Mary T ^a   Brock, Ian J ^a   Reichmann, Keith G ^a   McKenzie, Ross A ^a   Blaney, Barry J ^a  

^a DEPARTMENT OF AGRICULTURE AND FISHERIES   (Australia)

Author keywords

Bracken; Caudatoside; Ptaquiloside; Pteridium aquilinum; Pteridium esculentum; Ptesculentoside

Indexed keywords

BRACKEN; CAUDATOSIDE; PTAQUILOSIDE; PTERIDIUM AQUILINUM; PTERIDIUM ESCULENTUM; PTESCULENTOSIDE;

ANIMALS; DEGRADATION; FORESTRY;

SUGARS;

GLYCOSIDE; PLANT EXTRACT; SESQUITERPENE;

ANIMAL; ANIMAL DISEASE; ARTICLE; AUSTRALIA; BRACKEN FERN; CATTLE; CHEMISTRY; EVALUATION; FOOD POISONING; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVESTOCK; METHODOLOGY;

ANIMALS; AUSTRALIA; CATTLE; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FOODBORNE DISEASES; GLYCOSIDES; LIVESTOCK; PLANT EXTRACTS; PTERIDIUM; SESQUITERPENES;

ANIMALIA; PTERIDIUM AQUILINUM; PTERIDIUM AQUILINUM SUBSP. WIGHTIANUM; PTERIDIUM ESCULENTUM;

EID: 79955700594     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104267c     Document Type: Article

References (22)

1. Der, J. P.; Thomson, J. A.; Stratford, J. K.; Wolf, P. G. Global chloroplast phylogeny and biogeography of bracken (Pteridium; Dennstaedtiaceae). Am. J. Bot. 2009, 96, 1041-1049.
2. Brownsey, P. J. The taxonomy of bracken (Pteridium: Dennstaedtiaceae) in Australia. Aust. Syst. Bot. 1989, 2, 113-128.
3. McKenzie, R. A. Bovine enzootic haematuria in Queensland. Aust. Vet. J. 1978, 54, 61-64.
4. Everist, S. L. Poisonous Plants of Australia, 2nd ed.; Angus & Robertson: Sydney, Australia, 1981; pp 405-421.
5. Yamada, K.; Ojika, M.; Kigoshi, H. Ptaquiloside, the major toxin of bracken, and related terpene glycosides: chemistry, biology and ecology. Nat. Prod. Rep. 2007, 24, 798-813. (Pubitemid 47106917)
6. Fletcher, M. T.; Hayes, P. Y.; Somerville, M. J.; De Voss, J. J. Ptesculentoside, a novel norsesquiterpene glucoside from the Australian bracken fern Pteridium esculentum. Tetrahedron Lett. 2010, 51, 1997-1999.
7. Smith, B. L.; Embling, P. P.; Agnew, M. P.; Lauren, D. R.; Holland, P. T. Carcinogenicity of bracken fern (Pteridium esculentum) in New Zealand. N. Z. Vet. J. 1988, 36, 56-58.
8. Agnew, M. P.; Lauren, D. R. Determination of ptaquiloside in bracken fern (Pteridium esculentum). J. Chromatogr. 1991, 538, 462-468.
9. Smith, B. L.; Seawright, A. A.; Ng, J. C.; Hertle, A. T.; Thomson, J. A.; Bostock, P. D. Concentration of ptaquiloside, a major carcinogen in bracken fern (Pteridium spp.), from eastern Australia and from a cultivated worldwide collection held in Sydney, Australia. Nat. Toxins 1994, 2, 347-353.
10. Smith, B. L.; Seawright, A. A.; Ng, J.; Hertle, A. T.; Thomson, J. A.; Bostock, P. D. Ptaquiloside in bracken ferns (Pteridium spp.) from eastern Australia and from a cultivated collection of bracken from worldwide sources. In Plant-Associated Toxins: Agricultural, Phytochemical and Ecological Aspects; Colegate, S. M., Dorling, P. R., Eds.; CAB International: Wallingford, U.K., 1994; pp 45-50.
11. Rasmussen, L. H.; Lauren, D. R.; Smith, B. L.; Hansen, H. C. B. Variation in ptaquiloside content in bracken (Pteridium esculentum (Forst. f) Cockayne) in New Zealand. N. Z. Vet. J. 2008, 56, 304-309.
12. Bonadies, F.; Borzacchiello, G.;Dezzi, S.;Nicoletti, R.; Roperto, S. Mass spectrometric analysis of ptaquiloside, the toxic sesquiterpene from bracken fern. Rapid Commun. Mass Spectrom. 2004, 18, 825-828. (Pubitemid 38451030)
13. Castillo, U. F.; Wilkins, A. L.; Lauren, D. R.; Smith, B. L.; Alonso-Amelot, M. Pteroside A2, a new illudane-type sesquiterpene glucoside from Pteridium caudatum L. Maxon, and the spectrometric characterization of caudatodienone. J. Agric. Food Chem. 2003, 51, 2559-2564.
14. Ng, E. K.-M.; McMorris, T. C. An efficient synthesis of pterosin C and other pterosins. Can. J. Chem. 1984, 62, 1945-1953. (Pubitemid 15220196)
15. Tanaka, N.; Murakami, T.; Saiki, Y.; Chen, C. M.; Gomez, P. L. D. Chemical and chemotaxonomical studies of ferns. XXXVII. Chemical studies on the constituents of Costa Rican ferns (2). Chem. Pharm. Bull. 1981, 29, 3455-3463. (Pubitemid 12154614)
16. Fukuoka, M.; Kuroyanagi, M.; Yoshihira, K.; Natori, S. Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. II. Structure of pterosins, sesquiterpenes having 1-indanone skeleton. Chem. Pharm. Bull. 1978, 26, 2365-2385. (Pubitemid 9006552)
17. McGlone, M. S.; Wilmshurst, J. M.; Leach, H. M. An ecological and historical review of bracken (Pteridium esculentum) in New Zealand, and its cultural significance. N. Z. J. Ecol. 2005, 28, 165-184. (Pubitemid 43025814)
18. Oelrichs, P. B.; Ng, J. C.; Bartley, J. Purification of ptaquiloside, a carcinogen from Pteridium aquilinum. Phytochemistry 1995, 40, 53-56.
19. Van der Hoeven, J. C. M.; Lagerweij, W. J.; Posthumus, M. A.; Van Veldhuizen, A.; Holterman, H. A. J.; Aquilide, A a new mutagenic compound isolated from bracken fern (Pteridium aquilinum (L.) Kuhn). Carcinogenesis 1983, 4, 1587-1590. (Pubitemid 14206922)
20. Niwa, H.; Ojika, M.; Wakamatsu, K.; Yamada, K.; Hirono, I.; Matsushita, K. Ptaquiloside, a novel norsesquiterpene glucoside from bracken, Pteridium aquilinum var. latiusculum. Tetrahedron Lett. 1983, 24, 4117-4120.
21. Ojika, M.; Wakamatsu, K.; Niwa, H.; Yamada, K. Ptaquiloside, a potent carcinogen isolated from bracken fern Pteridium aquilinum var. latiusculum. Structure elucidation based on chemical and spectral evidence, and reactions with amino acids, nucleosides, and nucleotides. Tetrahedron 1987, 43, 5261-5274. (Pubitemid 17157035)
22. Prakash, A. S.; Pereira, T. N.; Smith, B. L.; Shaw, G.; Seawright, A. A. Mechanism of bracken fern carcinogenesis: evidence for H-ras activation via initial adenine alkylation by ptaquiloside. Nat. Toxins 1996, 4, 221-227. (Pubitemid 26411543)