209. Albaspidin

Nomenclature

CAS number: 58409-52-2
2,2′-Methylenebis[6-butyryl-3,5-dihydroxy-4,4-dimethyl-2,5-cyclohexadien-1-one]; polystichalbin; methylenebis(butyrylfilicinic acid); albaspidin-BB.
C25H32O8; mol wt 460.52.
C 65.20%, H 7.00%, O 27.79%.

Description and references

Found in the rhizomes of the male fern, Aspidium filix mas (L.) Schott., Dryopteris filix mas (L.) Schott., A. spinulosum, Polypodiaceae and other ferns. Isoln from Aspidium extract: Boehm, Ann. 318, 305 (1901); McGookin et al., J. Chem. Soc. 1953, 1828; see also Tryon et al., Phytochemistry 12, 683 (1973). Isoln as one component of a homologous mixture: Penttila, Sundman, Acta Chem. Scand. 18, 344 (1964). Synthesis: Riedl, Mitteldorf, Ber. 89, 2595 (1956); Inagaki et al., J. Pharm. Soc. Jpn. 76, 1258 (1956). Biosynthetic studies: Penttila, Fales, J. Am. Chem. Soc. 88, 2327 (1966).

Chemical structure

Properties

Crystals from ethanol or methanol, mp 149°. Freely sol in chloroform; moderately sol in ether, benzene; sparingly sol in alc, acetone, glacial acetic acid, sol in KOH solns; very sparingly sol in Na2CO3 solns. Practically insol in methanol.