2917. Desaspidin BB

Nomenclature

CAS number: 114-43-2
2-[[2,4-Dihydroxy-6-methoxy-3-(1-oxobutyl)phenyl]methyl]-3,5-dihydroxy-4,4-dimethyl-6-(1-oxobutyl)-2,5-cyclohexadien-1-one; 3′-[(5-butyryl-2,4-dihydroxy-3,3-dimethyl-6-oxo-1,4-cyclohexadien-1-yl)methyl]-2′,6′-dihydroxy-4′-methoxybutyrophenone; desaspidin; rosapin.
C24H30O8; mol wt 446.49.
C 64.56%, H 6.77%, O 28.67%.

Description and references

Isoln from the rhizome of Dryopteris austriaca (Jacq.) Wojnar, Polypodiaceae: Aebi et al., Helv. Chim. Acta 40, 266 (1957); from D. caucasica (A. Br.) Fraser-Jenkins et Corley: Widén et al., ibid. 56, 831 (1973). Structure: Aebi et al., ibid. 40, 572 (1957). Toxicity study: Airaksinan et al., Acta Pharmacol. Toxicol. 25, 33 (1967).

Chemical structure

Properties

Crystals from ether + petr ether, mp 150-150.5°. uv max: 230, 274 nm (ε 23000, 16800) in cyclohexane. Freely sol in ether, benzene, acetone. Practically insol in methanol, ethanol, petr ether. LD50 orally in mice: 340 mg/kg (Airaksinan).