Studies on the Alkaloids of Zephyranthes candida HERB. I

The Isolation of Bases

Abstract

Four known alkaloids, lycorine (I), tazettin (II), nerinine (III), haemanthidine (IV) and a new alkaloid C₁₆H₁₉O₄N, m.p. 201-202° (decomp.), were isolated from Zephyranthes candida HERB., Amaryllidaceae (Japanese name “Tamasudare”) which has been cultured in Japan as decorative plants.
Physical constants of the new alkaloid which is designated zephyranthine are as follows: [α]_D²⁴ -43.17° (c=0.47, CHCl₃); IR ν_max^KBrcm^-1: 3470 (-OH), 1040, 945 (methylenedioxy group); pKa′ 9.20 in water; UV λ_max^EtOH 291mμ (log ε 3.71). The alkaloid contains one methylenedioxyphenyl group, two hydroxyl groups and one tertiary nitrogen, but no N-methyl, O-methyl or olefinic unsaturated functional groups. It gives diacetate, C₂₀H₂₃O₆N, m.p. 68-70° and acetate hydrochloride, C₂₀H₂₃O₆N⋅HCI, m.p. 294-295° (decomp.).