Alkaloids fromNarcissus primigenius

Planta Medica
1994.0

Abstract

As part of our ongoing search for biologically active compounds from desert plants, we investigated Cowainea mexicana D. Don (Rosaceae), which has a history of use as a topical anti-infective agent by the Native Americans of this region. The above-ground biomass of the plant (voucher specimen SPM 5834) was collected on October 8, 1989 in the Santa Rita Mountains of Pima County, Arizona, U.S.A. We found this unexplored plant to be rich in ursolic acid and the three known derivatives, pomolic, 2a-hydroxyursolic, and 2-epi-tormentic acids. Tormentic acid has been reported to be an effective topical antibiotic against Streptococcus mutans (1); pomolic and 2a-hydroxyursolic acids have reported cytotoxic and potential antitumor activity (2, 3). Until recently, many different species and subspecies were found under the name Narcissus pseudonarcissus L. In some regions of Spain, infusions of their flowers are used for the treatment of coughs and colds, as well as for their emetic and purgative properties (1). In our studies on Amaryllidaceae species, we have worked with Narcissus primigenius (Fdez. Suarez ex Lainz) Fdez. Casas & Lainz (= N. pseudonarcissus subsp. primigenius) (2), a new taxon belonging to the Pseudonarcissus DC. section. We have studied the alkaloidal content of the whole plant, and four compounds have been obtained: homolycorine, 8-O-demethylhomolycorine, haemanthamine, and 8-O-demethylmaritidine (1). Alkaloid 1 has been isolated only twice before, from Hymenocallis rotata Herb. (3) and Sternbergia species (4). Dichrostachys glomerata (Forsk) Schouw (Mimosaceae) [voucher specimen (A 300) Laboratoire de Botanique et de Cryptogamie, Faculté de Pharmacie, Montpellier (Prof. C. Andary)] is a tree frequently occurring in the Bangui region. The bark is used in local medicine in decoctions against bad coughs in children and gynecological troubles in adults. The species Dichrostachys cinerea has been studied earlier and some common constituents as those described here have been obtained (1, 2). The barks were collected in the Bangui region, Village P.K. 55, road of Baikah (September 1991, rainy season). From 400 g of air-dried bark extracted with boiling hexane, 3.8 g of a residue were obtained (yield 1%), that gave a positive reaction with Liebermann-Burchard reagent. The residue stirred with CH2Cl2 which led to a yellow precipitate (250 mg) and a filtrate. The precipitate consisted of 1 (10 mg) and 2 (40 mg). The filtrate after evaporation and chromatography over silica gel on elution with CHCl3 gave 3 (14 mg), 4 (70 mg), 5 (17 mg), and 6 (24 mg): 1, m.p. 243°C; ElMS: m/z (M+, 426), was identified essentially by NMR (COSY, HMQC, HMBC), as friedelan-3-one, [α]D: -24° (CHCl3) (3). 2, m.p. 276°C (ElMS: m/z (M+, 428), the NMR spectrum was in accordance with that of friedelan-3-β-ol, [α]D: +21° (CHCl3) (4). 3, m.p. 273—275°C ElMS: m/z (M+, 456), was identified by the same NMR methods and comparison with authentical sample as betulinic acid, [α]D: +4° (CHCl3) (5, 6). 4, m.p. 80°C, ElMS: m/z (M+, 396), the NMR spectrum is identical to that of hexacosanoic acid (7). 5, m.p. 85—89°C, ElMS: m/z (M+, 426) (8, 9), was identified by NMR and comparison with an authentic sample obtained by Oppenhauer oxidation of β-sitosterol, to β-sitostenone, [α]D: +81° (CHCl3). 6, the 1H- and 13C-NMR spectra identified it as a triglyceride consisting of 2 molecules of palmitic acid and one of an unsaturated fatty acid.

Knowledge Graph

Similar Paper