The Lycopodium alkaloids

Lycopodium alkaloids are quinolizine, or pyridine and alpha-pyridone type alkaloids. Some Lycopodium alkaloids are potent inhibitors of acetylcholinesterase (AChE). Huperzine A (HupA) is reported to increase efficiency for learning and memory in animals, and it shows promise in the treatment of Alzheimer's disease (AD). 201 Lycopodium alkaloids from 54 species of Lycopodium (sensu lato) have been reported so far. This review is intended to to cover the chemical, pharmacological and clinical research on Lycopodium alkaloids reported in the literature from the spring of 1993 to August 2004. Structures of 81 new Lycopodium alkaloids are presented, classified and analyzed. The structural characters and biogenetic relationships of the four major Lycopodium alkaloid groups (lycopodine, lycodine, fawcettimine and miscellaneous) are discussed. Bioactivities of Lycopodium alkaloids, especially HupA, are summarized. In particular, the effect of HupA and other cholinesterase inhibitors (anti-AD drugs) on acetylcholine esterase (AChE) activity in the rat cortex and butylcholine esterase activity are compared. Structure-activity relationships and structure modifications of HupA and its analogs are described. Information on clinical trials with HupA and its derivative ZT-1 is presented. The state of HupA availability and recent advances in in vitro propagation of HupA producing plants are outlined. Finally, hypotheses about Lycopodium alkaloid biosynthetic pathways are discussed.     

Indole alkaloids from camptotheca acuminata

Five minor alkaloids were isolated from the seeds of Camptotheca acuminata Decne. Two of them are new indole alkaloids named camptacumotine (1) and camptacumanine (2) respectively. The others are known indole alkaloids naucleficine (3), angustoline (4) and dihydroisoquinamine (5), which was isolated for the first time from the plant.     

Berberis alkaloids. XV. Structure of bargustanine

Bargustanine (I), belonging to a new type of isoquinoline alkaloids, has been isolated from the phenolic fraction of the total alkaloids from the roots ofBerberis vulgaris L. Its structure has been established by chemical and spectral methods.Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Andizhan State Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–47, January–February, 1993.     

Berberis alkaloids XXXIX. New alkaloids fromB. densiflora

The alkaloid composition of the leaves ofBerberis densiflora has been studied. Berberine, -allocryptopine. oxyacanthine, glaucine, thalicmidine, isocorydine, O-methylcorypalline and the new bases densinine and densiberine have been isolated. The structures of the new alkaloids have been established by a study of spectral characteristics and chemical transformations. This is the first time that any of the known alkaloids, apart from berberine, have been isolated from a plant of this pecies and it is the first time that -allocryptopine and O-methylcorypalline have been isolated from theBerberis genus.     

Simultaneous determination of the content of isoquinoline alkaloids in Dicranostigma leptopodum (Maxim) Fedde and the effective fractionation of the alkaloids by high‐performance liquid chromatography with diode array detection

A simple and efficient method was developed for the simultaneous determination of eight isoquinoline alkaloids in methanol extracts of Dicranostigma leptopodum (Maxim) Fedde and the effective fractionation of the alkaloids of D. leptopodum by high‐performance liquid chromatography with diode array detection. The chromatographic conditions were optimized on a SinoChrom ODS‐BP column to obtain a good separation of the four types of alkaloid analytes, including two aporphines (isocorydine, corydine), two protopines (protopine and allocryptopine), a morphine (sinoacutine), and three quaternary protoberberine alkaloids (berberrubine, 5‐hydroxycoptisine, and berberine). The separation of these alkaloids was significantly affected by the composition of the mobile phase, and particularly by its pH value. Acetonitrile (A) and 0.2% phosphoric acid solution adjusted to pH 6.32 with triethylamine (B) were selected as the mobile phase with a gradient elution. With this method, a new quaternary protoberberine alkaloid was isolated and the two structural isomers (isocorydine and corydine) were baseline separated. The appropriate harvest period for D. leptopodum was also recommended based on our analysis. The method for the effective fraction of the alkaloids of D. leptopodum was optimized under this method with regard to the varying significant pharmacological activities of the alkaloids.     

Triterpenoid alkaloids from Buxus rugulosa

A new triterpenoid alkaloid, buxrugulosamine (1), together with four known, ones was isolated from the ethanolic extract of the leaves and twigs of Buxus rugulosa. Their structures were determined by analysis of spectral data or comparing them with authentic samples. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 163–164, March–April, 2008.     

Berberis alkaloids. XXII. Interbrinine and intebrimine — New alkaloids from Berberis integerrima

The known alkaloids reticuline, isoboldine, isocorydine, glaucine, armepavine, oxyacanthine, and heliamine and the new alkaloids intebrinine and intebrimine have been isolated from the total alkaloids of the leaves ofBerberis integerrima, and structures have been proposed for the latter two on the basis of spectral characteristics and independent synthesis.Andizhan State Medical Institute. Institute of the Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedeninii, No. 1, pp. 70–73, January–February, 1993.     

Indole alkaloids from the roots of an african plant securidaca longipedunculata. I. Isolation by column chromatography and preliminary structural characterization by mass spectrometry

The extraction and the isolation of some alkaloids from the roots of an African plant (Securidaca Longipedunculata Fres) are reported. The structural characterization was performed by mass spectrometry. Alternative ionization methods (FAB and EI), collisionally-induced decomposition experiments and accurate mass measurements revealed the presence of elymoclavine and dehydroelymoclavine and the presence of a new ergoline alkaloid.     

New cholinesterase inhibiting bisbenzylisoquinoline alkaloids from Cocculus pendulus

Phytochemical investigation on Cocculus pendulus (J. R. & G. FORST.) resulted in the isolation of two new and three known bisbenzylisoquinoline alkaloids. The structures of the new alkaloids, kurramine-2'-beta-N-oxide (1) and kurramine-2'-alpha-N-oxide (2), were elucidated with the help of spectroscopic techniques. The cholinesterase inhibitory activities of these bisbenzylisoquinoline alkaloids are reported here for the first time.     

Separation of vinca alkaloids by GLC

Summary A new GLC method was developed for the separation of vinca alkaloids. OV-101 stationary phase and programmed temperature analysis were used for the investigations. By this method the separation of closely related vinca alkaloids can be performed such as stereo and structural isomers, ester homologues of vincaminic and apovincaminic acids.

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Trennung von Vinca-Alkaloiden durch Gas-Chromatographie

Zusammenfassung Mit Hilfe von OV-101 als stationä-rer Phase und einem Temperaturprogramm (200–300° C, 5° C/min) konnten nahe verwandte Vinca-Alkaloide (Stereo- und Strukturisomere, Esterhomologe von Vincamin- und Apovincaminsäure) gas-chromatographisch getrennt werden.

     

Norditerpenoid alkaloids from the processed tubers of Aconitum carmichaeli

Four new and five known norditerpenoid alkaloids were isolated from the processed tubers of Aconitum carmichaeli. The new alkaloids are 14-O-cinnamoylneoline (3), 14-O-anisoylneoline (4) 14-O-veratroylneoline (5), and lipo-14-O-anisoylbikhaconine (8). The known alkaloids are neoline (1), 14-O-acetylneoline (2), foresaconitine (6), crassicauline A (7), and lipohypaconitine (9). Alkaloids 2, 6, and 7 were isolated from this plant for the first time. The structures of the new alkaloids were established by spectroscopic and chemical methods.     

New C18-diterpenoid alkaloids from Delphinium anthriscifolium var. savatieri

Five new C18-diterpenoid alkaloids, anthriscifolcines A (1), B (2), C (3), D (4), and E (5), together with a known C19-diterpenoid alkaloid delcorine (6), were isolated from the whole herb of Delphinium anthriscifolium var. savatieri. The structures of these new alkaloids were established on the basis of spectral data (1D- and 2D-NMR, HR-ESI-MS).     

选择性远程DEPT技术用于吡咯里西啶类生物碱的结构测定和核磁共振研究

本文从峨眉千里光中分得二个吡咯里西啶类生物碱.经测定,一个为阔叶千里光碱,另一个为新阔叶千里光碱.采用选择性远程^13CDEPT技术对这二个化合物的结构及其^1H和^13CNMR谱峰归属作了研究.     

Two new alkaloids from Crinum asiaticum var. sinicum

Two new alkaloids (1, 2) were isolated from the whole plants of Crinum asiaticum var. sinicum together with seven known alkaloids. The structures of the new alkaloids were elucidated by spectroscopic analyses and chemical conversions from known alkaloids. New alkaloid 1 was isolated for the first time as a natural product, although it has been prepared as a synthetic product.     

Minor alkaloids of Aspidosperma subincanum mart.: isolation, structure proof and synthesis of 1,2-dihydro-ellipticine, 1,2-dihydro-ellipticine methonitrate and ellipticine methonitrate

Three alkaloids named in the title were isolated from the Peruvian plant “Quillo-bordon.” The structures assigned were confirmed by partial syntheses.     

Berberis alkaloids. XXXVII. Investigation of the alkaloids ofB. oblongata andB. integerrima. Crystal structure of 8-trichloromethyldihydroberberine

Two species of Berberis have yielded 10 isoquinoline alkaloids. In addition to known bases, two artifacts have been isolated — 8-trichloromethyldihydroberberine (I) and 8-trichloromethyldihydropalmatine. An x-ray structural analysis has been made of (1).Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 889–893, November–December, 1996. Original article submitted April 15, 1996.     

Three new C_(20)-diterpenoid alkaloids from Delphinium anthriscifolium var.savatieri

Three new C20-diterpenoid alkaloids, designated as anthriscifolmines A-C (1-3), together with two known alkaloids denudatine and delgramine, were isolated from the whole herb of Delphinium anthriscifolium var. savatieri. The structures of these new alkaloids were elucidated on the basis of spectral data.     

Berberis alkaloids. XVII. Investigation of the alkaloids of Berberis heteropoda

The alkaloid composition of young shoots and leaves ofBerberis heteropoda Schrenk has been studied. In addition to known alkaloids, two new ones have been isolated — N-methyldihydroberberine and 8-oxoberberrubine, the structures of which were established by chemical transformations and a study of spectral properties. Of known alkaloids, berbamunine, aromoline, glaucine, thalicmidine, isocorydine, and reticuline have been found in this plant for the first time. Pseudopalmitine and laudanosine have been found for the first time in plants of the genusBerberis.Andizhan State Medical Institute. Institute of the Chemistry of Plant Substances of Uzbek Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 53–59, January–February, 1993.     

New bisbenzylisoquinoline alkaloids from Cocculus laurifolius

Two new bisbenzylisoquinoline alkaloids, alpha, alpha'-dioxo-7'-O-demethylstebisimine (1) and 7'-O-demethylstebisimine (2), along with 14 known alkaloids, were isolated from the roots of Cocculus laurifolius. These alkaloids were characterized mainly by spectroscopic methods.     

New C19-diterpenoid alkaloids from Aconitum piepunense

Two new C(19)-diterpenoid alkaloids, piepunensine A (1) and 18-acetylcammaconine (2), have been isolated from the roots of Aconitum piepunense together with five known alkaloids pengshenine B (3), talatisamine (4), aconosine (5), yunaconitine (6), and talatizidine (7). The structures of the new alkaloids were established on the basis of spectral data (1D- and 2D-NMR, HR-MS).