A new base, neferine (methiodide, m.p. 180-182°, C
38H
44O
6N
2⋅2CH
3I⋅2H
2O), as well as isoliensinine (I) has been isolated from “Lien Tze Hsin” (embryo of
Nelumbo nucifera GAERTN.), in Hong Kong market. O-Methylneferine (IV) (styphnate, m.p. 139-140°, [α]
D -93.3° (acetone)) was found to be completely identical with the synthesized O, O-dimethylisoliensinine (IV), reported previously. When O-ethylneferine (V) was subjected to the cleavage reaction by metallic sodium in liquid ammonia, D-1, 2, 3, 4-tetrahydro-6-methoxy-1-(
p-methoxybenzyl)-2-methyl-7-isoquinolinol (VI) and D-O-ethylarmepavine (VII) were obtained. Therefore, it has been verified that the structure of neferine was represented by the formula III.
The neferine (III), synthesized from VI and D-3′-bromoarmepavine (VIII) in the presence of cupric oxide and anhyd. potassium carbonate in pyridine was completely identical with the natural product (Table I).
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