Isolation of carinatine and pretazettine from the bulbs of Zephyranthes carinate Herb. (Amaryllidaceae).

Chemical and Pharmaceutical Bulletin
1977.0

Abstract

The bulbs of Zephyranthes carinata HERB. (Amaryllidaceae) were found to contain pretazettine (I) and a new phenolic base, carinatine (II), as well as lycorine (III), galanthine (IV), and haemanthamine (V). This paper reports the isolation of these alkaloids from the bulbs of Z. carinata and the structural assignment of carinatine. Carinatine (II), C₁₇H₂₁NO₄, was established to be O-demethylgalanthine based on its physical and spectral data (mass, IR, UV, NMR, ORD), the remarkable similarity of its chemical shifts to those of galanthine (IV), and confirmation by methylation with diazomethane to yield galanthine (IV). Carinatine was found to be a structural isomer of goleptine, as their optical rotations and the melting points of their picrates were different.

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