A new base was isolated from Formosan
Cassytha filiformis L. (Japanese name “Sunazuru, ” Chinese name “wu-ken-ts'ao”) (Lauraceae) and was named cassyfiline. This base occurs as light orangeish brown, microgranules of m.p. 217° (decomp.), [α]
D15-89.6° (CHCl
3), and its composition corresponds to C
19H
19O
5N. Its solution in organic solvents exhibit a strong green fluorescence. The ultraviolet spectrum of cassyfiline has absorption maxima at 284.5 and 305mμ, suggesting an aporphine-type base. Its NMR spectrum (CDCl
3) indicated a phenolic secondary base possessing two benzene protons, one methylenedioxy group, and two methoxyl groups.
O, N-Dimethylcassyfiline (III) occurs as colorless columnar crystals of m.p. 139-140°, [α]
D24+42.6° (CHCl
3), C
21H
23O
5N, which was identified with ocoteine, m.p. 137-138°, by mixed melting point and comparison of infrared spectra (CHCl
3) (Fig. 3) and NMR spectra (CDCl
3) (Fig. 2).
Determination of the position of the hydroxyl group followed the method used by Barton and his co-workers for that in apo crotonosine. N-Methyldeuterocassyfiline (V) was prepared from N-methylcassyfiline (IV), and NMR spectra of these two were compared. From the disappearance of the peak at 3.20τ, hydrogen in 8-position was found to have been deuterated, which proved the presence of a hydroxyl in 9-position. From these results, the structure of cassyfiline was clarified as 1, 2-methylenedioxy-3, 10-dimethoxy-9-hydroxy-N-noraporphine (I).
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