Pyrrolizidine Alkaloids fromSyneilesis aconitifolia*

Planta Medica
1995.0

Abstract

Ervatainia corymbosa Roxb. ex Wall (Apocynaceae) is a tree growing to 15 meters in height in Malaysia. The different parts of this plant are used in traditional medicine for treatment of syphilic and orchitis ulcerations. Barks and roots are also utilised in making arrow poison (1). The present note reports on the isolation and identification of the alkaloids from the leaves and stem bark of this species. This work is a part of our continuing research on the genus Ervatamia (2—4). Plant material (leaves: 0.5 kg and stem bark: 1.5 kg) was collected in June 1990 at Keluang (Johore) and identified by two of us (H. S. and T. S.). Voucher specimens are kept in the Herbarium of the Department of Phytochemistry of Malaya (Numbers F.H.S. 248 A and 249 A). Leaves and stem bark were extracted with EtOH and the dried extracts were dissolved in 2% H₂SO₄. This aqueous solution was basified with ammonia and extracted with CHCl₃. The organic layer was concentrated to give the alkaloid mixture (A. M.) with following yields: 4.2 % (leaves), 2 % (stem bark). Purification was performed by column chromatography (silica gel, CHCl₃ with increasing amount of MeOH). Isolation of seven alkaloids was realised by preparative TLC, except for yohimbine and β-yohimbine, which were obtained by direct crystallization of column fractions. The isolated alkaloids were identified by direct comparison (co-TLC, UV, IR, MS, NMR) with authentic samples available in the laboratory (4), and with published data for modestanine (6) and vandrikine (7). These findings are of taxonomic interest because of the presence of several alkaloids with the yohimbine skeleton which is exceptional in the genus Ervatainia. Thus, E. corymbosa seems chemically close to E. hirta (4), another Malaysian species; Syneilesis aconitfolia Maxim. (Compositae, subtribe Senecioneae) is a traditional folk remedy which is called "Tu er shan" in China. The whole plant is used as an analgesic and antirheumatic medicine (1). Some terpene glucosides were detected previously in the title plant (2). The present paper describes the isolation of a mixture of two pyrrolizidine alkaloids. Both alkaloids have been isolated previously from Syneilesis palinata (3, 4) but some data have been improved. On the basis of structure-toxicity-relationships, both alkaloids should be toxic (5); Tinospora cordifolia Miers (Menispermaceae) is widely used in the Indian system of medicine for its general tonic, anti-malarial, anti-diabetic, anti-inflammatory and hepato-protective properties (1, 2). The roots of T. cordifolia were collected from Varanasi, India in September, 1993 (a voucher specimen number PH/02/92 is deposited at the author's department). Chemically, the plant is known to elaborate alkaloids, diterpenoidal furanolactones, and their glycosides (1, 3). In the present study, the alcoholic extract of the defatted root powder of T. cordifolia (1.0 kg) was dried, treated with citric acid solution (7%, 0.5 l) and to the acidic extract was added the Mayer's reagent in excess. The Mayer's complex was stirred with Amberlite IRA-400 (Cl⁻), the supernatant was filtered, concentrated, dried, and eluted on a column of silica gel (70 g). The CHCl₃: CH₃OH (85: 15) eluates (140—150 ml) yielded an isoquinoline alkaloid (35 mg). The spectral data (mass, UV, ¹H-NMR, and ¹³C-NMR) of the isolated compound and its acetate and borohydride-reduced product were found to be in complete agreement with those reported in the literature for jatrorrhizine and its derivatives (4). Their identities were further confirmed by direct comparison with authentic samples.

Knowledge Graph

Similar Paper