Abstract
The title compound, C20H22N2O2, an alkaloid isolated from the Madagascar periwinkle, crystallizes in P1 with two independent but closely similar mol-ecules in the unit cell. The mol-ecules are linked into pairs by two N-H⋯O=C hydrogen bonds. The absolute configuration was confirmed by anomalous dispersion effects as S at the 3 and 15 positions, and R at the 7 position.
Highlights
The title compound crystallizes in space group P1 with two independent molecules (Fig. 1)
The title compound was isolated using a combination of highperformance countercurrent chromatography (HPCCC) (Ito, 2005), preparative C18 high-performance liquid chromatography (HPLC) and silica-gel column chromatography (Ito, 2005)
The dried powder was immersed in water adjusted to pH 2 by trifluoroacetic acid (TFA), homogenized by a T-25 digital ULTRA-TURRAX (IKA, Staufen, Germany) at maximum speed (25 000 rpm for 10 min) and shaken overnight for extraction
Summary
Aerial parts of the plant contain between 0.2 and 1% of a mixture of more than 120 alkaloids (van Der Heijden et al, 2004). The dimeric alkaloids that result from the joining of two compounds can display interesting pharmaceutical activities. Ajmalicine, a monomeric indole alkaloid present in the root of C. roseus, is an antihypertensive alkaloid (Noble, 1990). Roseus, is an antihypertensive alkaloid (Noble, 1990) In view of their medical and commercial value, the appropriate methods of extraction and purification have been well studied. We have undertaken the X-ray crystal structure determination of the title compound in order to establish its absolute stereochemistry. As the final purification step was performed with an alkaline solvent mixture, the NMR data of akuammicine correspond to the free base, and can be linked to the determined stereochemistry
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