Alkaloidal constituents of Hymenocallis rotata Herb. (Amaryllidaceae).

Chemical and Pharmaceutical Bulletin
1987.0

Abstract

We previously reported the isolation of leucotamine (1), β-methylleucotamine (2) and 3-β-acetylungiminorine (3) from Leucojum asetivum L. (Amaryllidaceae). This paper reports the isolation of two new alkaloids, demethylmaritidine (4) and (-)-N-demethyllycoramine (5), together with eleven known alkaloids (vittatine (6), alkaloid-13 (7), 3-epimacronine (8), ismine (9), pretazettine (10), lycoramine (11), lycorine (12), tazettine (13), haemanthamine (14), galanthamine (15), and N-demethylgalanthamine (16)) from the bulbs of Hymenocallis rotata HERB. (Amaryllidaceae). Boit and Dopke isolated lycorine (12), galanthamine (15) along with hipeastrine and homolycorine from this plant. Compound 4 was isolated as colorless prisms from acetone and identified as β-demethylmaritidine based on spectral data (IR, 1H-NMR, MS, ORD) and conversion to maritidine via methylation with diazomethane. Compound 5 was isolated as pale yellow prisms and determined to be (-)-N-demethyllycoramine by spectral analysis (IR, 1H-NMR, MS) and methylation to lycoramine using boric acid, formalin, and sodium borohydride. The eleven known alkaloids were confirmed by comparing their spectral data (IR, 1H-NMR, MS) and mixed melting points with authentic samples.

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