Alkaloids ofHaplophyllum perforatum

Chemistry of Natural Compounds
1985.0

Abstract

The alkaloids skimmianine, evoxine, perfamine, flindersine, haplamine and the lignan eudesmin have been isolated previously from the epigeal part of Haplophyllum perforatum collected in the budding and incipient flowering period in the Baisun region. In the present study, the epigeal part of H. perforatum from the same growth site but at the end of flowering was investigated. A methanolic extract of the epigeal part (5.5 kg) was separated into basic (19 g of ether-soluble and 17 g of chloroform-soluble) and neutral (160 g) fractions. By chromatography, the ethereal fraction yielded eudesmin (0.009% on the weight of the dry raw material), skimmianine (0.017%), base I (anhydroevoxine, 0.001%, mp 125-126°C, mol. wt. 329 identified by mass spectrometry, IR and PMR spectra), base II (methylevoxine, 0.005%, mp 86-87°C identified by NMR spectrum and melting point), flindersine (<0.001%), and haplamine (0.008%); the chloroform fraction yielded evoxine (0.036%); and the neutral fraction yielded eudesmin (0.02%), perfamine (0.036%), and haplamine (0.07%). The known compounds were identified by direct comparison with authentic samples. A comparative study with the results of the epigeal part collected in an earlier vegetation period showed that as the plant developed, the amounts of eudesmin, haplamine, flindersine, perfamine, and skimmianine decreased considerably, while the amount of evoxine and the formation of its analogs (methylevoxine and anhydroevoxine) increased. In previous investigations on the dynamics of alkaloid accumulation in H. perforatum from other growth sites, the opposite pattern was observed: the level of evoxine and its analogs decreased considerably as the plant grew, and that of skimmianine increased.

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