Alkaloids from Embryo of the Seed of Nelumbo Nucifera

Journal of Natural Products
1986.0

Abstract

Previous chemical studies of heartwood and root from genera of Bignonaceae and Proteaceae have shown the presence of the compound known as lapachol, an important quinone (1) having antimicrobial characteristics (2,3). This work describes the isolation of lapachol from Diphysa robinoider Bent (Leguminosae). The plant material was collected near the central coast of Veracruz State, Mexico, where the tree grows wild on a limited scale, and was authenticated by the Herbarium of the Universidad Veracruzana at Xalapa, where a voucher specimen has been deposited. There is no previous report of the isolation of lapachol from other species of the genus Diphysa. The embryo of the seed of Nelumbo nucifera Gaertn. (Nymphaeaceae) (embryo loti) has been used in traditional medicine as an antifebrile, antipsychotic, and antihypertensive agent (1). Chao et al. (2) reported the isolation of liensinine from the embryo loti of Chinese origin, which had antihypertensive activity. On the other hand, Tomita et al. (3) reported the isolation of isoliensinine from the embryo loti of Taiwan origin, which is inactive. Despite the absence of liensinine, we have observed that the aqueous extract of the embryo loti of Taiwan origin shows antihypertensive activity on spontaneously hypertensive rats. Our interest has been directed to the investigation of the constituents of the embryo loti, with the aim of isolating biologically active substances; this paper describes the isolation of four alkaloids, i.e., isoliensinine, neferine, (2)-armepavine, and 4'-methyl-N-methylcolaurine. The antihypertensive principle was characterized as neferine. The isolation of 4'-methyl-N-methylcoclaurine is the first report of its occurring as a natural product, though it is synthetically known as a product from cleavage of neferine by sodium in liquid NH3 (4). This is the first time that co-occurrence of bis-coclaurine-type alkaloids (isoliensinine and neferine) and coclaurine-type alkaloids [(2)-armepavine and 4'-methyl-N-methylcoclaurine] in the embryo loti is reported. Fungal metabolites have gained attention recently in view of their chemical diversity. There are no reports on the chemical constituents of Ulocladium botrytis Preuss, a seed-borne fungus of pearl millet (Pennisetum typhoides) and hence the present investigation. Monosporic cultures of U. botrytis in modified Czapeks medium (1) were incubated at 27-29°C for 15 days. The whole cultures were extracted in a liquid-liquid extractor using CHCl3. Silica gel column chromatography of the extract using petroleum ether and C6H6 yielded dodecane (ir, ¹H nmr, ms) (2) and 9,10,12,13-tetrahydroxyheneicosanoic acid (ir, ¹H nmr, ms) (3,4). The latter compound was earlier reported from the fungus Haematomma ventosum (4). The details of isolation and identification of the compounds are available on request.

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