Ungernia alkaloids

The review is devoted to the study of the alkaloids of plants of the genusUngernia (Amaryllidaceae). It gives their characteristic reactions and information on the determination of their structures and stereochemistry and on the dynamics of the accumulation of alkaloids in the plants of the genusUngernia. A dependence of the physiological activity of the alkaloids on their structure is shown.Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek, SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 749–767, November–December, 1980.     

Berberis alkaloids

This review systematizes literature information on alkaloids of plants of the genusBerberis. The main chemical and spectral methods of establishing their structures, and also their pharmacological properties, are considered. The review includes literature sources up to 1992.     

Structures of nitramine and isonitramine — Alkaloids of a new type from plants of the genusNitraria

The proof of the structures of two isomeric alkaloids — nitramine and isonitramine — from two species of plants of the genusNitraria is given. Their diastereoisomerism with respect to the C₇ asymmetric atom has been established. This is the first time that alkaloids with the structure of 2-azaspiro[5,5]undecan-7-ol have been found.     

Chemical composition and pharmacological properties of plants of the genusStachys

This review gives information of the distribution of alkaloids, carbohydrates, lipids, essential oils, diterpenoids, iridoids, flavonoids, and pigments in plants of the genusStachys L. (fam. Lamiaceae). It has been shown that the genusStachys is of interest for researchers as a source of biologically active substances of various classes which are responsible for the broad spectrum of pharmaceutical-therapeutic action of plants of this genus and drugs prepared from them. Characteristic for these plants is a low content of saturated fatty acids in the seed lipids and, in the epigeal part, of essential oils, an accumulation of iridoids of the aucubin type, and the fact that all the flavone derivatives present have a large number of substituents in ring A of the flavone nucleus. This indicates the antiquity and phylogenetic primitiveness of theStachys genus. The results of chemical and pharmacological-therapeutic studies of plants of theStachys genus growing on the territory of the former USSR are given. Literature sources up to and including 1991 have been used.     

Alkaloids ofHaplophyllum foliosum

The alkaloids skimmianine, dubinidine, foliosidine, graveoline, and compounds (I) and (II) have been isolated from the epigeal part of the plantHaplophyllum foliosum Vved. (family Rutaceae). On the basis of the spectral characteristics of (I) and its 0-isopropylidene derivative it has been established that the compound is the alkaloid edulinine. Substance (II) was identified as ferulic acid by direct comparison with an authentic sample. This is the first time that edulinine and ferulic acid have been detected in plants of the genusHaplophyllum.     

Berberis alkaloids

This review systematizes literature information on alkaloids of plants of the genusBerberis. The main chemical and spectral methods of establishing their structures, and also their pharmacological properties, are considered. The review includes literature sources up to 1992.Andizhan State Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 481–506, July–August, 1993.     

Alkaloids ofHaplophyllum foliosum. II.

In addition to the alkaloids known previously from this plant, haplofoline and folifine, from the epigeal part ofHaplophyllum foliosum we have isolated norgraveoline with mp 288–289°C (decomp. from acetone), and myrtopsine with mp 201–202°C (from chloroform), [α]_D-5° (c 0.05; methanol), which were first obtained fromHaplophyllum dubium andMyrtopsis sellingii, respectively. We have confirmed by the PMR-spectroscopic method the positions of the substituents in the dihydrofuran ring of myrtopsine suggested previously on the basis of biogenetic considerations. In addition, it has been established that the substituents are present in the trans form. This is the first time that myrtopsine has been detected in plants of the genusHaplophyllum.     

Sesquiterpene derivatives of the genusFerula

The review is devoted to a study of the sequiterpene derivatives of the plants of the genusFerula (Apiaceae). Information is given on the determination of the structure, stereochemistry, and characteristic reactions of 78 coumarins, 39 esters, and six sesquiterpene alcohols isolated from plants of the genusFerula. The possible biogenetic interrelationships and mutual transitions of the sesquiterpenes that are derivatives of aliphatic and of mono- and bicyclic hydrocarbons are discussed. Some information confirming the hypotheses made is given.     

Alkaloids of the Genus Datura: Review of a Rich Resource for Natural Product Discovery

The genus Datura (Solanaceae) contains nine species of medicinal plants that have held both curative utility and cultural significance throughout history. This genus’ particular bioactivity results from the enormous diversity of alkaloids it contains, making it a valuable study organism for many disciplines. Although Datura contains mostly tropane alkaloids (such as hyoscyamine and scopolamine), indole, beta-carboline, and pyrrolidine alkaloids have also been identified. The tools available to explore specialized metabolism in plants have undergone remarkable advances over the past couple of decades and provide renewed opportunities for discoveries of new compounds and the genetic basis for their biosynthesis. This review provides a comprehensive overview of studies on the alkaloids of Datura that focuses on three questions: How do we find and identify alkaloids? Where do alkaloids come from? What factors affect their presence and abundance? We also address pitfalls and relevant questions applicable to natural products and metabolomics researchers. With both careful perspectives and new advances in instrumentation, the pace of alkaloid discovery—from not just Datura—has the potential to accelerate dramatically in the near future.     

13C-NMR studies on the cevanine alkaloids : the application of 13C-NMR spectrum for structure elucidation of new alkaloids,baimonidine and isoverticine

The ¹³C-NMR spectra of seven cavanine alkaloids isolated from Veratrum and Fritillaria plants were measured and their signals were assigned, and these results were applicated for structure elucidation of two new cevanine alkaloids, baimonidine and isoverticine, isolated from mature Fritillaria verticillata.     

Phytoecdysteroids of plants of the genusSilene

Ecdysteroids produced by plants of the genusSilene are considered. The discussion covers 17 species of plants, from which 45 ecdysteroids have been isolated. It has been shown that ecdysterone is the most characteristic representative of the biosynthesis of ecdysteroids in theSilene series.     

Chemical composition and pharmacological properties of plants of the genusStachys

This review gives information of the distribution of alkaloids, carbohydrates, lipids, essential oils, diterpenoids, iridoids, flavonoids, and pigments in plants of the genusStachys L. (fam. Lamiaceae). It has been shown that the genusStachys is of interest for researchers as a source of biologically active substances of various classes which are responsible for the broad spectrum of pharmaceutical-therapeutic action of plants of this genus and drugs prepared from them. Characteristic for these plants is a low content of saturated fatty acids in the seed lipids and, in the epigeal part, of essential oils, an accumulation of iridoids of the aucubin type, and the fact that all the flavone derivatives present have a large number of substituents in ring A of the flavone nucleus. This indicates the antiquity and phylogenetic primitiveness of theStachys genus. The results of chemical and pharmacological-therapeutic studies of plants of theStachys genus growing on the territory of the former USSR are given. Literature sources up to and including 1991 have been used.Division of the Institute of Chemical Physics of the Russian Academy of Sciences, Chernogolovka, fax 2926511 - BOX 18777; and Tashkent State University, fax 462472. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 699–709, November–December, 1994.     

Classification,Toxicity and Bioactivity of Natural Diterpenoid Alkaloids

Diterpenoid alkaloids are natural compounds having complex structural features with many stereo-centres originating from the amination of natural tetracyclic diterpenes and produced primarily from plants in the Aconitum, Delphinium, Consolida genera. Corals, Xenia, Okinawan/Clavularia, Alcyonacea (soft corals) and marine sponges are rich sources of diterpenoids, despite the difficulty to access them and the lack of availability. Researchers have long been concerned with the potential beneficial or harmful effects of diterpenoid alkaloids due to their structural complexity, which accounts for their use as pharmaceuticals as well as their lousy reputation as toxic substances. Compounds belonging to this unique and fascinating family of natural products exhibit a broad spectrum of biological activities. Some of these compounds are on the list of clinical drugs, while others act as incredibly potent neurotoxins. Despite numerous attempts to prepare synthetic products, this review only introduces the natural diterpenoid alkaloids, describing ‘compounds’ structures and classifications and their toxicity and bioactivity. The purpose of the review is to highlight some existing relationships between the presence of substituents in the structure of such molecules and their recognised bioactivity.     

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.     

Alkaloids of four species of Argemone

The alkaloid compositions of four species of plants of the genusArgemone (A. mexicana L.,A. alba L.,A. platyceras Link et Otto., andA. hybrida) collected in the flowering phase in the Tashkent Botanical Garden have been studied. They have yielded 16 alkaloids. Corydine and isocorydine have been detected in plants of this genus for the first time, and O-methyl-platycerine has been found in nature for the first time.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 204–206, March–April, 1986.     

Structure of ophiorines A and B; novel type gluco indole alkaloids isolated from ophiorrhiza spp.

Two novel type gluco indole alkaloids, ophiorines A and B, were found in Rubiaceous plants, Ophiorrhiza japonica B1. and O. kuroiwai Mak., and their structures were elucidated by chemical and spectroscopical methods.     

Cannabinoids,Phenolics, Terpenes and Alkaloids of Cannabis

Cannabis sativa is one of the oldest medicinal plants in the world. It was introduced into western medicine during the early 19th century. It contains a complex mixture of secondary metabolites, including cannabinoids and non-cannabinoid-type constituents. More than 500 compounds have been reported from C. sativa, of which 125 cannabinoids have been isolated and/or identified as cannabinoids. Cannabinoids are C₂₁ terpeno-phenolic compounds specific to Cannabis. The non-cannabinoid constituents include: non-cannabinoid phenols, flavonoids, terpenes, alkaloids and others. This review discusses the chemistry of the cannabinoids and major non-cannabinoid constituents (terpenes, non-cannabinoid phenolics, and alkaloids) with special emphasis on their chemical structures, methods of isolation, and identification.     

Alkaloids of Haplophyllum bungei

The alkaloids dictamnine, skimmianine, folimine, robustinine, and 4-methoxy-2-quinolone, found for the first time in plants of the genusHaplophyllum and the new alkaloid haplobungine, for which the structure of 4,7,8-trimethoxy-2-quinolone has been established, have been isolated from the epigeal part of the plantHaplophyllum bungei Trautv. growing in the Moiynkumy desert, Chimkent province, Kazakh SSR.Institute of Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 23–25, January–February, 1989.     

Three new Lycopodium alkaloids from Huperzia carinata and Huperzia squarrosa

Eleven Lycopodium alkaloids with lycodine-type, lycopodine-type, and fawcettimine-related skeletons were isolated from the whole plants of Huperzia carinata (Desv. Ex. Poir.) Trevis and Huperzia squarrosa (G. Forst) Trevis (Huperziaceae). Among them, 8,15-dihydrohuperzine A (2), lycocarinatine A (3), and lycoposerramine U N-oxide (11) are new compounds. The structures of these new alkaloids were elucidated on the basis of 2D NMR correlations. Some of these isolated alkaloids were assayed for acetylcholinesterase (AChE) inhibitory activity.