An investigation of the alkaloids ofSenecio francheti, Trachelanthus hissoricus, andT. korolkovii

Chemistry of Natural Compounds
1967.0

Abstract

The comminuted roots of Polygonum coriarium Grig. collected in the autumn, 1966, at the Talgar Peak, Alma-Ata Region, were successively extracted with benzene and ether. After the evaporation of the benzene extract, an oily product remained with a yield of 1.8% (of the weight of the absolutely dry roots). By chromatographing it on alumina with subsequent elution with methanol, β-sitosterol with mp 136-137°C (from ethanol) was obtained. The acetate had mp 122-124°C, [α]D -40°C (c 0.23; chloroform), [α]D -89°C (c 0.28, chloroform). Yield 0.11% of the weight of the roots. When the ethereal extract of the roots was evaporated to small bulk, with subsequent storage at -5°C, β-sitosterol monoglucoside was obtained with mp 294-296°C (from ethanol). The acetate of the glucoside had mp 169-170°C, [α]D -32.3°C (c 0.30; pyridine). Yield 0.004%. The substances were identified by elemental analysis, IR spectra, and the products of acid hydrolysis. β-Sitosterol and its monoglucoside have been isolated previously from the seeds of jute and the roots of Delphinium dehudatum [1, 2]. For S. francheti C. Winkl., the raw material was collected in the flowering stage (15 June 1966) at Sary-Dashte, Tadzhik SSR. Four hundred grams of the epigeal part of the plant was extracted with isopropanol acidified with acetic acid, giving 1.23g of ether alkaloids and 3.2 g of chloroform alkaloids (1.1% of the weight of the dry raw material). By treatment with acetone, the chloroform fraction of the combined alkaloids (3.2 g) yielded 1.74 g of the N-oxide of sarracine [1]. The combined ether alkaloids (1.23 g) were separated by the polybuffer method, depositing 70 mg of crystals with mp 124-125°C (from ether) at pH 7 and 8, which was a new base named franchetine. For T. hissoricus Lipsky, the sample was obtained on the R. Obi'Khengau, Tadzhik SSR (8 June 1966) in the fruitbearing stage. Two hundred grams of the leaves was exhaustively extracted with methanol, obtaining 6.1 g of chloroform alkaloids and 9.31 g of reduced alkaloids (7.73% of the weight of the dry plant). From the combined chloroform alkaloids (6.7 g) were isolated 5.14 g of the N-oxide of viridiflorine [2] and 0.2 g of trachelanthine [8], and from the reduced alkaloids (9.37 g) was obtained 4.8 g of viridiflorine [4] and 2.24 g of trachelanthamine [8]. For T. korolkovii (Lipsky) Fedtsch., the plant was first studied by Men'shtkov and Borodin [8], who obtained 0.4-2.5% of combined alkaloids and isolated trachelanthamine and trachelanthine; we isolated the same alkaloids but in larger amount in its early vegetation period [5]. From the epigeal part of L. albertii Rgl. collected in the flowering stage in Fergana Region, chloroform extracted 1.75% of combined bases. From the latter were isolated thaspine [1], N-methylcytisine [2], and a crystalline base with mp 108-109°C (from petroleum ether), [α]D +59.3°C (c 1.30; ethanol), C15H24N2O, rel. wt. 248 (mass spectrometry). The base is monoacidic and ditertiary, forming a monomethiodide with mp 249°C (from a mixture of ethanol and acetone). Its IR spectrum has absorption bands for trans-linked quinolizidine (2800-2700 cm⁻¹) and six-membered lactam carbonyl (1655 cm⁻¹) [3]. Reduction with lithium aluminum hydride gave a deoxybase with mp 60-61°C, [α]D +41°C (c 0.219; ethanol), whose physicochemical properties (except rotation sign) agreed with sophoridine [4].

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