Examinations were made on quaternary bases in
Stephania japonica MIERS (Japanese name “Hasunoha-kazura”) and a new crystalline base was isolated. This base, named steponine, agrees with the molecular formula C
20H
24O
4N
+, possessing two methoxyls, two phenolic hydroxyls, and one N-methyl group. Its chloride, C
20H
24O
4NCl⋅H
2O, m.p. 235° (decomp.), shows following constants: [α]
D21-129.89°(H
2O); U.V. λ
maxMeOH mμ (logε): 234 (4.12), 282 (3.85); λ
minMeOH 256mμ (logε 2.76). It colors slightly greenish with ferric chloride and deep blue with the Gibbs reagent.
Recently, Tomita and Kikuchi isolated a new quaternary base, cyclanoline, from
Cyclea insularis (MAKINO) DIELS and determined its structure as
l-α-N-methylscoulerine (IV). Cyclanoline chloride, C
20H
24O
4NCl⋅H
2O, m.p. 214-215°(decomp.); [α]
D8-115.8° (MeOH); U.V. λ
maxMeOH mμ (log ε): 233 (4.13), 286 (3.88); λ
minMeOH 255mμ (log ε 2.79). It was described as giving almost no change with ferric chloride and coloring deep blue with Gibbs reagent. Although steponine and cyclanoline (IV) are extremely alike, the infrared spectra of the two chlorides were not identical. Since the infrared spectra of their respective O, O-dimethyl-methine (VI) were completely identical, it was assumed that steponine might be α, β-steric isomer of the N-methyl group in cyclanoline or position isomers of the substituents (two methoxyls and two phenolic hydroxyls) in the protoberberine skeleton.
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