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We have isolated from the tubers ofAconitum karakolicum collected in the Kirghiz SSR, Kungei Alatau range, songorine, napelline, a base with mp 159–160°C, and the new alkaloids karakoline and a base with mp 222–224°C.

A structure has been proposed for lappaconitine on the basis of its chemical and spectral characteristics.

1. The structure of the new alkaloid lapaconidine has been established. 2. The structure proposed previously for the product of the reaction of lappaconine with sulfuric acid has been confirmed on the basis of chemical and spectral studies.

The main routes of fragmentation of diterpene alkaloids with the lycoctonine skeleton under the action of electron impact are discussed.

The known alkaloids isotalatisidine, nevadensine, delcosine, delsoline, and isobaldine have been isolated form the epigeal part ofDelphinium confusum M. Pop., collected in the flowering period, and also a new alkaloid with the composition C24H39NO5, mp 136–137°C (acetone), for which the structure of 14-methylisotalatisidine has been established on the basis of spectral characteristics and of passages from condelphine and isotalatisidine. This is the first time that the alkaloids nevadensine, delcosine, delsoline, isobaldine, and 14-methylisotalatisidine have been isolated from this plant.

The dynamics of the accumulation of alkaloids in the epigeal part ofAconitum karakolicum according to vegetation periods has been studied. It has been established that the highest content of alkaloids is found in the early period. On separating the combined alkaloids, the aporphine alkaloid isoboldine has been isolated from this plant for the first time and a new base has been obtained — napelline N-oxide, the structure of which has been shown on the basis of the results of a study of spectral characteristics and direct transition to napelline.

The epigeal part ofAconitum monticola Steinb. has yielded two C18 diterpene alkaloids which, on the basis of the results of a study of NMR, IR, and mass spectra, and also of chemical transitions, have been shown to be identical with synthetic deoxydelosline and dihydromonticamine. This is the first time that these alkaloids have been found in a plant.

The structures of the new diterpene alkaloid zeraconine and its N-oxide, isolated fromAconitum zeravschanicum, have been established on the basis of spectral characteristics and chemical transformations.

Continuing the separation of the total alkaloids of the plantPapaver arenarium M.B., collected in the region of Lake Sevan in the flowering period, we have isolated macrostomine, glycomarine, cheilanthifoline, sevanine, arenine, and two isomeric macrostomine N-oxides not previously described in the literature.

1. It has been established that on protonation the threo isomers of phthalide-isoquinolines undergo an inversion of the signs of the CE's in the 290 and 200 nm regions, while in the case of the erythro compounds only the amplitudes of the corresponding CE's in the CD curves change. 2. An interconnection has been established between the preferred conformations of the threo and erythro forms and the relative intensities of the 'Lb CE's in the CD curves of the phthalide-isoquinolines.

A new C20-diterpene alkaloid of the coryphine type has been isolated from the plantAconitum coreanum (Levl.) Rapaics, and it has been called coryphidine. Its structure has been established on the basis of an analysis of IR and1H and13C NMR spectra. This is the second diterpene alkaloid having a hexahydro-N-methylindole fragment at C-17. Coryphidine contains an imide grouping, which is unusual for a diterpene skeleton.

From the epigeal part ofAconitum karakolicum growing in the upper reaches of the R. Tyup (KirghizSSR) have been isolated phenyl-β-naphthylamine, aconitine, aconifine, songorine, napelline, and the new base acetylnapelline. On the basis of a study of spectral characteristics and chemical transformations it has been shown that the alkaloid is the C-11-monoacetate of napelline.

The alkaloids of the epigeal part and roots ofCorydalis stricta have been studied. Of the 23 alkaloids isolated, N-methylcorypalline proved to be new, and its structure has been determined. Stilopine hydroxymethylate and pycnarrhine have been isolated from the genusCorydalis for the first time, and cheilanthiofoline isocorypalmine, scoulerine, isoboldine, reticuline, N-methylcoclaurine, coreximine, juziphine, pancorydine, corypalline, wilsonirine, stilopine, adlumidine, dihydrosanguinarine, adlumine, and bicucculine have been isolated from this species of plant for the first time.

Isocorydine, corydine, protopine,l-adlumine, d-bicuculline,l-adlumidine, gortschakoine, juziphine, domesticine, isoboldine, corytuberine, stylopine, sendaverine, and the new alkaloids sendaverine N-oxide and juziphine N-oxide have been isolated from the epigeal part ofCorydalis gortschakovii growing in the upper regions of the R. Pskem.

The reaction of C19-diterpene alkaloids with sodium and liquid ammonia in the presence and in the absence of a proton donor — an alcohol — has been investigated. In the absence of the proton donor the hydroxy group is converted into a carbonyl group, which is characteristic only for C-6-hydroxy or -acetoxy derivatives.

Periodic acid does not oxidize delterine, an alkaloid fromDelphinium ternatum. However, the further oxidation of 19-oxodelterine, obtained on oxidation by Marion's method, led to oxosecodelterine, which is a semiacetal formed through the C-7 carbonyl group and the C-10 hydroxy group. The treatment of this compound with sulfuric acid led to oxosecodemethanoldelterine.

From the epigeal part ofPapaver bracteatum Lindl. (family Papaveraceae) growing in the region of Mt. Beshtau (Pyatigorsk) 12 bases have been isolated: isothebaine and oripavine, isolated previously, and thebaine, mecambridine, orientalidine, alpinine, alpigenine, salutaridine, floripavidine, bracteoline, and bases (I) and (II), isolated for the first time.

A new alkaloid has been isolated from the eipgeal part of theAconitum karakolicum Rapaics. and has been called 12-epinapelline. The structure of the new alkaloid has been shown by the preparation of a diacetate and an iso derivative and also by the direct passage from songorine to 12-epinapelline and a study of their spectral characteristics.

Fifteen bases have been isolated from three species ofCorydalis. Dihydrosanguinarine has been isolated from a plant of the genusCorydalis for the first time.

The alkaloids from the epigeal part of the wild blackspot horn poppy have been studied. Twelve alkaloids have been isolated of which one — norbracteoline — proved to be new. Its structure has been established. Dehydrocorydine, predicentrine, glaufidine, thalicmidine, reticuline, and stylopine α-methohydroxide have been isolated from this plant for the first time.

Relative difficulty of saponifying an acetoxy group at C1 and ease of acylation of a hydroxy group in this position as compared with a hydroxy group C10 has been shown for alkaloids with a lycoctonine skeleton. The anomalously easy saponification of a C1-acetoxy group in karakolidine acetates is due to the influence of the neighboring C13-hydroxy group.

The epigeal part ofAconitum barbatum gathered in the early vegetation period in the environs of Ulan-Bator has yielded delcosine, lycoctonine, songorine, and the new base bataconine. The structure of bataconine has been shown on the basis of spectral characteristics (IR, NMR, and mass spectra) and also of a correlation with the known alkaloid neoline.

A mass spectrometric method for determining the configuration of the substituent at C-1 in the lycoctonine alkaloids has been proposed. The mass spectra of the carbinolamine ethers of three diterpene alkaloids have been studied. The possibility of using these spectra for determining the nature of the substituent at C-4 has been shown.

The most probable structures have been proposed for fumaridine and fumaramine on the basis of their spectral characteristics and chemical transformations.

It has been shown that with a decrease in the number of substitutents in ring E the ease of pyrolysis of the aconitum alkaloids falls.

Uraline, a new norditerpenoid alkaloid, was isolated from aerial parts of Delphinium uralense. The structure of 1alpha,7,8-trihydroxy-6beta,14alpha,16beta-trimethoxy-18-N-(2-methyl)succinylanthranoyloxyaconane was ascribed to the new compound on the basis of 1H and 13C NMR, IR, and mass spectra. The known alkaloids methyllycaconitine and delcorine were also isolated from the plant.

The plantFumaria vaillantii Loisl. has yielded protopine, fumaridine, fumaramine, d-α-hydrastine,l-adlumine, d-bicuculline, andl-adlumidine (this being the first time thatl-adlumidine has been isolated from the genusFumaria), and the new base vaillantine. On the basis of UV, IR, NMR, and mass spectra, and also the identity of O,O-dimethylvaillantine with muramine, the structure of vaillantine has been established as 2,3-didemethylmuramine.

UV spectrum: ~ethanol 221, 290, 326 nm (log e 4.35, 3.44 3.51) max ' ' The IR spectrum of the base shows absorption bands at (cm -I) 920, 1040 (methylenedioxy group), 1610 (aromatic ring), 1750 (carbonyl group), and 3350 (hydroxy group). The mass spectrum of corledine lacks the peak of the molecular ion, and the maximum ion is one with m/e 192. There are also ions with m/e 177, 149, and 135. The characteristics of its UV, IR, and mass spectra enable us to assign corledine to the phthalide-isoquinoline alkaloids [3, 4]. In harmony with this conclusion is also the PMR spectrum of (I) (CDCIa, 0 -HMDS), which shows the following signals (ppm): singlets at 2.60 (3H, N--CHa), 3.74 (3H, OCHa), 5.98 (2H, -OCH=O--), 6.35 and 6.63 (IH, IH, p-aromatlc protons); doublets at 4.02 (IH, aj = 3.8 Hz, C,-H), 5.61 (IH, aj = 3.8 Hz, Cg--H), 6.80 and 7.14 (IH, IH, aj = 8.0 Hz, o-aromatic protons). The protons of the methylenedioxy groups are represented by a multiplet at 2.22-3.04 ppm. The signal from the hydroxy group is strongly broadened and is found at 4.90 ppm. The acetylation of the base with acetic anhydride in pyridine gave an O-acetyl derivative with mp 162-164°C.

In order to confirm the structures of the alkaloids delcorine and delcoridine (O-demethyldelcorine) suggested previously, a direct passage has been performed from delcoridine to delcorine and from delcorine to delphatine. It has been shown that the α configuration of C1 - OCH3 previously suggested for delcorine and delcoridine is incorrect — it should be β.

From the combined alkaloids ofPapaver orientale we have isolated isothebaine, oripavine, thebaine, mecambridine, orientalidine, alpinigenine, protopine, bracteoline, oripavidine, and the new alkaloid isothebaidine, the structure of which has been established.

The new spirobenzylisoquinoline base lederine with mp 208–209°C (methanol), [α]D +13° (c 0.84; chloroform) has been isolated fromCorydalis ledebouriana Kar et Kir andDicentra peregrina (Rudolphi) Fedde. Its structure has been established on the basis of spectral characteristics and chemical reactions.

Together with delcorine, lycoctonine, eldeline, dehydrodelcorine, ilidine, browniine, and dictyocarpinine, we have isolated a new alkaloid, delcoridine, from the epigeal part ofDelphinium iliense Huth. Its structure has been established on the basis of the results of a study of the chemical transformations and spectra characteristics. This is the first time that the alkaloid dictyocarpinine has been isolated from this plant.