7930. Ptaquiloside
Nomenclature
CAS number: 87625-62-5
7′a-(β-d-Glucopyranosyloxy)-1′,3′a,4′,7′a-tetrahydro-4′-hydroxy-2′,4′,6′-trimethyl-(2′R,3′aR,4′S,7′aR)-spiro[cyclopropane-1,5′-[5H]inden]-3′(2′H)-one; braxin C; PT. C20H30O8; mol wt 398.45.
C 60.29%, H 7.59%, O 32.12%.
Description and references
Norsequiterpene glucoside identified as the carcinogenic priniciple of the bracken ferns, Pteridium spp. Isoln from P. aquilinum var. latiusculum: H. Niwa et al., Tetrahedron Lett. 24, 4117 (1983). Structure elucidation: eidem, ibid. 5371. HPLC determn in ferns: M. P. Agnew, D. R. Lauren, J. Chromatogr. 538, 462 (1991). Mechanism of carcinogenesis: M. Ojika et al., Tetrahedron 43, 5261 (1987); A. S. Prakash et al., Nat. Toxins 4, 221 (1996). Levels in cow's milk and health implications: M. E. Alonso-Amelot et al., Lait 78, 413 (1998). Review of chemistry and carcinogenic mechanisms: K. Yamada et al., Angew. Chem. Int. Ed. 37, 1818-1826 (1998); of biological activity: M. Shahin et al., Mutat. Res. 443, 69-79 (1999).
