No abstract
A new glycoalkaloid, edpetinosine, has been isolated from Petilium eduardi bulbs, and its structure has been established on the basis of chemical transformations and spectral characteristics.Continuing a study of the alkaloids of Petilium eduardi (Regel) VVed.[1], we have isolated from the bulbs, in addition to the alkaloids peimisine and edpetiline obtained previously [1, 2], the new alkaloid edpetinosine (1) with mp 174-176~ composition C33H55NO 7.The IR spectrum of (1) (KBr, v, cm -I) contained absorption bands at 3335 (OH), 2870-2925 (-CH 2,-CH3), and 1024-1160 (C-O of the sugar moiety).In the mass spectrum the main peaks were those of ions with m/z (Irel, %): 98
Among the neuroreceptors of the organism, the muscarinic receptors are the most widely distributed and take part in the regulation of the activity of all the vitally important organs [1]. It was previously considered that the muscatinergic system was a unity. Of the group of muscarinotropic agents, the M-cholinoblocker atropine and substances similar to it are used in cardiology, gastroenterology, ophthalmology, anesthesiology, etc. In view of the fact that these substances block the Mreceptors of various organs simultaneously, their therapeutic use is accompanied by many side-effects, and the search for selective M-cholinotropic agents is an urgent task in pharmacology.In recent years proofs have appeared of the existence of four subtypes of M-cholinoreceptors [2]. The process of differentiating M-receptors is obviously still incomplete. The clinical use of selective M-cholinotropic substances is in its initial stage. It is known that the Ml-cholinoblocker pirenzepine or gastrozepin is being used successfully for the treatment of stomach and duodenal ulcers [3]. The possibility has been suggested of using selective M-cholinotropic compounds in the treatment of Alzheimer's disease [4].It has been established previously that imperialine and a number of its esters possess a selective M2-cholinoblocking property [5][6][7][8]. In this paper we give the results of an investigation of features of the cholinoblocking activity of chlorine derivatives of imperialine: o~-chloroimperialine, ~3-chloroimperialine, and a mixture of the a-and E-isomers (ce,/3chloroimperialine).We isolated imperialine (1) from the bulbs and epigeal parts of a plant of the Petilium genus [9], and from it obtained a mixture of ce-and j3-chloroimperialines, the subsequent separation of which led to ce-chloroimperialine (2) and 8chloroimperialine (3). The structures of (2) and (3) were established on the basis of spectral characteristics [8]. We carried out a comparative investigation of the chlorine derivatives with atropine and imperialine. We investigated the antagonism of the compounds to the action on the heart of the negative chronotropic action of carbachol administered in the maximum tolerated dose, 0.02 mg/kg i/v, to narcotized rats. In these experiments we evaluated the M2-cholinoblocking activities of the compounds. The antagonism of the compounds to the secretory action of carbachol was taken as M3-cholinoblocking activity; antagonism to the spasmogenic action of carbachol on isolated ileum as M4-cholinoblocking activity; and antagonism of the alkaloids to the tremor action of arecoline as the central M-blocking activity.We calculated the doses of the substances lowering the effects of carbachol and arecoline by 50%, i.e., EDs0 and ECs0. The activity indices were expressed in micromoles --#mole/kg and #mole/liter -, and also in percentages of the activ/ty of the standard M-cholinoblocker atropine sulfate. As the results of the investigation (Table 1) show, ot-chloroimperialine proved to be the most active, and its ~3-isomer the least act...
547.944]945Three new compounds, the structures of which are confirmed using chemical and spectral data, are prepared by modification of imperialin.Imperialin (1) is the main component in Petilium eduardi and P. raddeana [ 1 ]. Esters and halide-containing derivatives of imperialin exhibit high M-,-choline blocking activity [2][3][4]. Three new compounds (3, 5, 6) (Scheme 1) were synthesized from 1 in order to produce more physiologically active compounds and to study the nature of their activity.
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