Ptesculentoside, a novel norsesquiterpene glucoside from the Australian bracken fern Pteridium esculentum

Tetrahedron Letters

Volumn 51, Issue 15, 2010, Pages 1997-1999

  Fletcher, Mary T ^a   Hayes, Patrica Y ^b   Somerville, Michael J ^a   De Voss, James J ^b  

^a DEPARTMENT OF AGRICULTURE AND FISHERIES   (Australia)

^b UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Bracken; Caudatoside; Ptaquiloside; Pteridium esculentum; Pterosin; Ptesculentoside; Sesquiterpene glucoside

Indexed keywords

CARCINOGEN; CAUDATOSIDE; GLUCOSIDE; PTAQUILOSIDE; PTEROSIN G; PTESCULENTOSIDE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AUSTRALIA; BRACKEN FERN; CARCINOGEN TESTING; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PTERIDIUM ESCULENTUM;

PTERIDIUM AQUILINUM; PTERIDIUM ESCULENTUM;

EID: 77649271171     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.032     Document Type: Article

References (25)

1. Vetter J. Acta Vet. Hung. 57 (2009) 183-196
2. Yamada K., Ojika M., and Kigoshi H. Nat. Prod. Rep. 24 (2007) 798-813
3. Thomson J.A., Mickel J.T., and Mehltreter K. Bot. J. Linn. Soc. 157 (2008) 1-17
4. Der J.P., Thomson J.A., Stratford J.K., and Wolf P.G. Am. J. Bot. 96 (2009) 1041-1049
5. Niwa H., Ojika M., Wakamatsu K., Yamada K., Hirono I., and Matsushita K. Tetrahedron Lett. 24 (1983) 4117-4120
6. Van der Hoeven J.C.M., Lagerweij W.J., Posthumus M.A., Van Veldhuizen A., and Holterman H.A.J. Carcinogenesis 4 (1983) 1587-1590
7. Ojika M., Wakamatsu K., Niwa H., and Yamada K. Tetrahedron 43 (1987) 5261-5274
8. Oelrichs P.B., Ng J.C., and Bartley J. Phytochemistry 40 (1995) 53-56
9. Castillo U.F., Wilkins A.L., Lauren D.R., Smith B.L., Towers N.R., Alonso-Amelot E., and Jaimes-Espinoza R. Phytochemistry 44 (1997) 901-906
10. Castillo U.F., Ojika M., Alonso-Amelot M., and Sakagami Y. Bioorg. Med. Chem. 6 (1998) 2229-2233
11. Castillo U.F., Wilkins A.L., Lauren D.R., Smith B.L., and Alonso-Amelot M. J. Agric. Food Chem. 51 (2003) 2559-2564
12. Alonso-Amelot M.E., Rodulfo-Baechler S., and Jaimes-Espinoza R. Biochem. Syst. Ecol. 23 (1995) 709-716
13. Agnew M.P., and Lauren D.R. J. Chromatogr. 538 (1991) 462-468
14. Smith B.L., Seawright A.A., Ng J., Hertle A.T., Thomson J.A., and Bostock P.D. In: Colegate S.M., and Dorling P.R. (Eds). Plant-associated Toxins: Agricultural, Phytochemical and Ecological Aspects (1994), CAB International, Wallingford UK 45-50
15. Smith B.L., Seawright A.A., Ng J.C., Hertle A.T., Thomson J.A., and Bostock P.D. Nat. Toxins 2 (1994) 347-353
16. Smith B.L., Embling P.P., Agnew M.P., Lauren D.R., and Holland P.T. N. Z. Vet. J. 36 (1988) 56-58
17. Rasmussen L.H., Lauren D.R., Smith B.L., and Hansen H.C.B. N. Z. Vet. J. 56 (2008) 304-309
18. Rasmussen L.H., Bruun Hansen H.C., and Lauren D. Chemosphere 58 (2005) 823-835
19. Williams D.H., and Fleming I. Spectroscopic Methods in Organic Chemistry. 5th ed. (1995), McGraw-Hill, Glasgow
20. 7,8 but the C-2 stereochemistry in these compounds is 2R as the methyl group is of lower priority order.
21. Fukuoka M., Kuroyanagi M., Yoshihira K., and Natori S. Chem. Pharm. Bull. 26 (1978) 2365-2385
22. Yoshihira K., Fukuoka M., Kuroyanagi M., Natori S., Umeda M., Morohoshi T., Enomoto M., and Saito M. Chem. Pharm. Bull. 26 (1978) 2346-2354
23. Tanaka N., Murakami T., Saiki Y., Chen C.-M., and Gomez P.L.D. Chem. Pharm. Bull. 29 (1981) 3455-3463
24. König W.A., Benecke I., and Bretting H. Angew. Chem., Int. Ed. Engl. 20 (1981) 693-694
25. 24