ヤクモソウ成分の研究 (第1報)
1962 年 82 巻 7 号 p. 1020-1024
詳細
1962 年 82 巻 7 号 p. 1020-1024
The plant of Leonurus sibiricus L. (Japanese name “Yakumoso” or “Mehajiki”) (Labiatae) was colleted during the flowering season and extracted as shown in Chart 1. The alkaloid, leonurine, was obtained in 0.02-0.04% yield. Free leonurine, m.p. 238°(decomp.), C14H21O5N3⋅H2O; hydrochloride, m.p. 194° (monohydrate); styphnate, m.p. 214-215°; oxalate, m.p. 191-192°. At the begining of flowering, content of leonurine is small and 0.03% of fumaric acid was obtained from the fruiting season of the plant. Glucoside and rutin were obtained in 0.1% yield from the whole herb during the fruit-bearing season. Leonurine (I) possesses two methoxyls and is positive to phenolic and alcoholic hydroxyl. It gives positive Dragendorff and Sakaguchi reactions and negative Meyer reaction. Hydrolysis of (I) with hydrochloric acid gives syringic acid (II), m.p. 206°, C9H10O5, the acid and its ethyl ester, m.p. 90.5°, agreed with the synthesized specimens. The mother liquor of this hydrolysis afforded the picrate of (III), C5H13ON⋅C6H3O7N3, m.p. 155°. Hydrolysis of (I) with sodium hydroxide or barium hydroxide afforded (II) as well as ammonia and a C4-amino alcohol as a benzoate of m.p. 74.5°, C11H15O2N, and p-nitrobenzoate of m.p. 163°, C18H17O7N3 (Chart 2).
