Quaternary alkaloids of Thalictrum foliolosum

The isolation and identification of eleven alkaloids from the quaternary alkaloid fraction of a root extract of Thalictrum foliolosum are described     

Quaternary protoberberine alkaloids

This contribution reviews some general aspects of the quaternary iminium protoberberine alkaloids. The alkaloids represent a very extensive group of secondary metabolites with diverse structures, distribution in nature, and biological effects. The quaternary protoberberine alkaloids (QPA), derived from the 5,6-dihydrodibenzo[a,g]quinolizinium system, belong to a large class of isoquinoline alkaloids. Following a general introduction, the plant sources of QPA, their biosynthesis, and procedures for their isolation are discussed. Analytical methods and spectral data are summarized with emphasis on NMR spectroscopy. The reactivity of QPA is characterized by the sensitivity of the iminium bond CN(+) to nucleophilic attack. The addition of various nucleophiles to the protoberberine skeleton is discussed. An extended discussion of the principal chemical reactivity is included since this governs interactions with biological targets. Quaternary protoberberine alkaloids and some related compounds exhibit considerable biological activities. Recently reported structural studies indicate that the QPA interact with nucleic acids predominantly as intercalators or minor groove binders. Currently, investigations in many laboratories worldwide are focused on the antibacterial and antimalarial activity, cytotoxicity, and potential genotoxicity of QPA.     

Bioactive aporphine alkaloids from the stems of Dasymaschalon rostratum

Three undescribed aporphine alkaloids dasymaroine A (1), 3-methoxyoxoputerine N-oxide (2), and dasymaroine B (3), along with nine known analogues (4–12) were isolated from the stems of Dasymaschalon rostratum Merr. The structures were elucidated using spectroscopic methods and by comparison with published NMR spectroscopic data. Compound 1 is a rarely reported nitro aporphine alkaloid and its absolute configuration was defined based on negative specific rotation and single-crystal X-ray diffraction. Compound 2 represents the first example of oxoaporphine alkaloid N-oxide. All compounds were evaluated for their activities of six pathogenic bacteria, 1 exhibited significant inhibition against Escherichia coli and Saphylococcus aureus with MIC values of 1.2 and 2.5 μM, respectively. As well as compounds 1–5, 7, 10, 12 were evaluated for their anti-HIV activities with EC₅₀ ranged from 1.93 to 9.70 μM.     

Isoquinoline and isoindole alkaloids from Menispermum dauricum

Three isoquinoline alkaloids and an isoindole alkaloid, along with eight known compounds, were isolated from the roots of Menispermum dauricum (Menispermacese). The alkaloids were characterized as 7-hydroxy-6-methoxy-1(2H)-isoquinolinone, 6,7-dimethoxy-N-methyl-3,4-dioxo-1(2H)-isoquinolinone, 1-(4-hydroxybenzoyl)-7-hydroxy-6-methoxy-isoquinoline and 6-hydroxy-5-methoxy-N-methylphthalimide, on the basis of spectral evidence including 1D- and 2D-NMR and MS analyses.     

Isoquinoline alkaloids isolated from three Guatteria species

The chemical investigation of the aerial parts of Guatteria ferruginea collected in the National Park of Serra dos Órgãos, Teresópolis, Brazil and of Guatteria latifolia and Guatteria sellowiana collected in the National Park of Itatiaia, Itatiaia, Brazil resulted in the isolation and identification of six isoquinoline alkaloids, two aporphine alkaloids 3-hydroxy-nornuciferine (1), nornuciferine (2) and four oxoaporphine alkaloids lysicamine (3), isomoschatoline (4), liriodenine (5) and O-methylmoschatoline (6). The isoquinoline alkaloids were found in the species G. ferruginea, G. latifolia and G. sellowiana for the first time and they support the taxonomic position within the genus Guatteria. Isoquinoline alkaloids (5–6) can be considered chemotaxonomic markers of the subfamily Annonoideae.     

中国小檗属二新异名

通过模式标本检查以及原始文献分析,对《中国植物志》(第29卷)小檗属未收录的2种植物进行了分类修订,将Berberisheteropsis Ahrendt处理为鳞叶小檗B.lepidifolia Ahrendt的异名;将B.mairei Ahrendt处理为西山小檗B.wangii Schneid.的异名。     

Biological evaluation of phenolic constituents from the trunk of Berberis koreana

A bioassay-guided fractionation and chemical investigation of the trunk of Berberis koreana resulted in the isolation and identification of a new sesquilignan, named berbikonol (1), along with fourteen known lignan derivatives (2-15) and a new phenolic compound, named berfussinol (16), together with five known ones (17-21). The structures of these new compounds were elucidated on the basis of 1D and 2D NMR spectroscopic data analysis as well as circular dichroism (CD) spectroscopy studies. Compounds 1-5, 7-8, 11, and 14 showed significant cytotoxicity against the XF498 cell line with IC₅₀ values of 7.14-19.32 μM. In addition, compounds 3-8 and 15 strongly reduced nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells, a microglial cell line.     

Isoquinoline alkaloids from cell suspension cultures of Fumaria capreolata

Fumaria capreolata was taken into cell suspension culture. The culture yielded a biomass of about 12 g dry weight per liter of medium; the dried cells contained ca. 0.1% of alkaloids. Besides choline, the following ten known isoquinoline alkaloids were isolated from the cell extract in crystalline form: coptisine, dehydrocheilanthifoline; (+)-isoboldine; magnoflorine; N-methylcoclaurine; (+)-reticuline; (–)-pallidine; protopine; sanguinarine; (–)-scoulerine. This is the most diverse isoquinoline alkaloid spectrum thus far published for a cell suspension culture.     

Isoquinoline alkaloids from the leaves of Annona leptopetala (Annonaceae)

The phytochemical investigation of the leaves of Annona leptopetala (R. E. Fr.) H. Rainer led to the characterization of tetrahydroprotoberberine corypalmine, and four aporphine (laurotetanine, anonaine, norannuradhapurine and nornuciferine) alkaloids. The structures were established after analysis of their NMR spectral data including 2D NMR experiments. This is the first report of laurotetanine and nornuciferine in A. leptopetala as well as norannuradhapurine in the genus Annona. The ¹³C NMR data of the natural alkaloid norannuradhapurine are reported here for the first time, and the NMR data for the compound corypalmine are reviewed.     

Isoquinoline alkaloids from the leaves of Xylopia laevigata (Annonaceae)

1. Download : Download full-size image

     

Isoquinoline alkaloids from Mahonia aquifolium stem bark are active against Malassezia spp

Bioassay directed fractionation of crude extract fromMahonia aquifolium led to the isolation of fraction A (bisbenzylisoquinoline alkaloid complex, BBI) and a fraction of protoberberine alkaloids, where the major compounds berberine and jatrorrhizine were isolated as their iodides. The antifungal activity of the crude extract, two protoberberine alkaloids and BBI fromM. aquifolium stem bark were evaluated against six strains ofMalassezia spp. The compounds tested were generally found to possess only weak to moderate antifungal properties: the MICs for individual strains were in the range ≤50–≥1000 mg/L.     

13C NMR spectral analysis of some isoquinoline alkaloids

The ¹³C NMR spectra of some isoquinoline and tetrahydroisoquinoline alkaloids and their corresponding N-methosalts and of the bisbenzylisoquinoline alkaloid isochondodendrine were recorded and the signals assigned. The substituent shielding effects and the ¹³C¹H long range couplings were analysed and utilized in the spectral interpretation.     

Taxonomic synopsis of Berberis (Berberidaceae) from the northern Hengduan mountains region in China,with descriptions of seven new species

Though Berberis (Berberidaceae) is widely distributed across the Eurasian landmass it is most diverse in the Himalaya–Hengduan Mountain (HHM) region. There are more than 200 species in China where it is one of the most common mountain shrubs. The study on the taxonomy and evolution of Berberis in this region can thus provide an important insight into the origin and diversification of its flora. A prerequisite to this is mapping and describing the various species of Berberis in the region – a task that despite recent progress is by no means complete. It is clear that in China there may be a significant number of species still to be described and that even with published species much about their distribution remains to be discovered. As a contribution to the first of these tasks seven new species from the northern Hengduan Mountain of N. Sichuan and S. Qinghai: Berberis chinduensis, Berberis degexianensis, Berberis jiajinshanensis, Berberis jinwu, Berberis litangensis, Berberis longquensis and Berberis riparia, are described here. Differences in overall morphology and especially in floral structures with each other and with similar species of Berberis in the same region are presented. The report is the result of phylogenetic analyses based on plastome and partial nrDNA sequences of both the seven proposed new species and a significant number of similar species already published. Provisional conclusions as to the insights provides on the history of the genetic divergence are discussed.     

Aporphine alkaloids of annona squamosa

The aporphine alkaloids anonaine, roemerine, norcorydine, corydine, norisocorydine, isocorydine and glaucine have been isolated from Annona squamosa.