New selective acetylcholinesterase inhibitors designed from natural piperidine alkaloids

Five new piperidine alkaloids were designed from natural (-)-3-O-acetyl-spectaline and (-)-spectaline that were obtained from the flowers of Senna spectabilis (sin. Cassia spectabilis, Leguminosae). Two semi-synthetic analogues (7 and 9) inhibited rat brain acetylcholinesterase, showing IC50 of 7.32 and 15.1 mu M, and were 21 and 9.5 times less potent against rat brain butyrylcholinesterase, respectively. Compound 9 (1 mg/kg, ip) was fully efficacious in reverting scopolamine-induced amnesia in mice. The two active compounds (7 and 9) did not show overt toxic effects at the doses tested in vivo. (c) 2005 Elsevier Ltd. All rights reserved.

Anxiolytic effects of erythrinian alkaloids from Erythrina mulungu

One new erythrinian alkaloid derivative, (+)-11 alpha-hydroxyerythravine (1), and the known (+)-erythravine (2) and (+)-alpha-hydroxyerysotrine (3) were isolated from the flowers of Erythrina mulungu. Their structures were determined by spectroscopic/spectrometric data interpretation of H-1, C-13, and 2D NMR and MS experiments. The relative configuration was established by NOESY analysis, while the conformation adopted by these molecules was evaluated through molecular modeling studies and coupling constants obtained by NMR analysis. Furthermore, the anxiolytic effects of the E. mulungu aqueous alcoholic crude extract and of the purified alkaloids were evaluated using the elevated T-maze test.

Effects of erythrinian alkaloids isolated from Erythrina mulungu (Papilionaceae) in mice submitted to animal models of anxiety

The effects of acute oral administration of erythrinian alkaloids, Le. (+)-alpha-hydroxy-erysotrine, erythravine and (+)-11 alpha-hydroxy-erythravine isolated from the flowers of Erythrina mulungu were investigated in two animal models of anxiety in mice-the light-dark transition model (LDTM) and the elevated plus-maze (EPM). In the LDTM, erythravine (3, 10 mg/kg) and (+)-11 alpha-hydroxy-erythravine (10mg/kg) increased the time spent by the animals in the illuminated compartment and (+)-11 alpha-hydroxy-erythravine (3 mg/kg) increased the number of transitions between compartments of the LDTM, suggesting an anxiolytic-like effect of these erythrinian alkaloids. Nevertheless, the third alkaloid studied, (+)-alpha-hydroxy-erysotrine, did not change any behavioral response with the range of doses used (3-10 mg/kg). Since the oral administration of the crude extract of E. mulungu (EM) (100-400 mg/kg) did not modify the conventional measures of anxiety in the EPM, this animal model was not chosen to evaluate the anxiolytic properties of the isolated alkaloids. These results suggest that the alkaloids erythravine and (+)-11 alpha-hydroxy-erythravine are responsible for the anxiolytic effects of the crude extract of E. mulungu.

Tetrahydroisoquinoline alkaloids and 2-deoxyribonolactones from Aristolochia arcuata

2-Deoxyribonolactones and four tetrahydroisoquinoline alkaloids were isolated from the acetone extract of the leaves of Aristolochia arcuata Mast., together with pinitol, sequoyitol, glycerol, fructose, sucrose, eupomatenoid-7, salsolinol, and 6,7-dihydroxyl,1-dimethyl-1,2,3,4-tetrahydroisoquinoline. Their structures were determined on the basis of spectroscopic methods, mainly using H-1, C-13, N-15, and P-31 NMR. (C) 2003 Elsevier B.V. Ltd. All rights reserved.

BIOACTIVE AND OTHER PIPERIDINE ALKALOIDS FROM CASSIA-LEPTOPHYLLA

Four new piperidine alkaloids, leptophyllin A (4), 3-acetylleptophyllin A (5), leptophyllin B (8), and (-)-spectaline (1), and 3 known piperidine alkaloids, (-)-spectalinine (2), canavaline (3), and iso-6-canavaline (7), were isolated by a bioassay-guided fractionation of a leaf extract of Cassia leptophylla. The alkaloids 1 - 3 were active in a mechanism-based DNA-modifying yeast assay and 2 was moderately active in Vero monkey and Chinese hamster ovary cell cytotoxicity assays.

Gas chromatographic analysis of indole alkaloids from Tabernaemontana hilariana

A fast and efficient procedure was elaborated to identify the alkaloid constituents from Tabernaemontana hilariana (Apocynaceae). The strategy based on fractioning of the crude alkaloid fraction in small silica cartridges followed by thin-layer chromatography (TLC), capillary gas chromatography-flame ionization detection as well as high-resolution gas chromatography-mass spectrometry afforded voacangine, coronaridine, ibogamine, voacangine pseudoindoxyl, voacangine hydroxyindolenine, 3-hydroxycoronaridine and 3-(2-oxopropyl)coronaridine. (C) 1997 Elsevier B.V. B.V.

Bioactive sesquiterpene pyridine alkaloids from Maytenus aquifolium

Two new sesquiterpene evoninate alkaloids, were isolated together with the known compounds syringaresinol and 4'-O-methyl-(-)-epigallocatechin from the root bark of Maytenus aquifolium. The structures of the two alkaloids were elucidated by interpretation of their spectral data, and both exhibited very weak activity in a mechanism-based DNA-modifying yeast assay. (C) 1998 Elsevier B.V. Ltd. All rights reserved.

ALKALOIDS FROM ARISTOLOCHIA-ARCUATA

Phytochemical studies with Aristolochia arcuata led to the isolation of KNO3, fructose, sucrose, sitosterol, calarene, its 2-oxo derivative, and three neolignans. Besides which, two new 13-oxidodibenzo[a, g]-quinolizinium alkaloids were isolated. They present only one oxygenated substituent at rings A and D.

Bioactive guanidine alkaloids from Pterogyne nitens

Bioactivity-guided fractionation of a methanolic CHCl 3 extract of the leaves of Pterogyne nitens afforded the known guanidine alkaloid pterogynidine [2] and three new guanidine alkaloids, nitensidines A [3], B [4], and C [5], all of which exhibited selective activity towards the DNA repair-deficient yeast mutant RS 321 (IC 12=9.3-20.0 μg/ml); 3,4, and 5 were moderately cytotoxic to CHO Aux B 1 cells (IC 50=8.5-13.0 μg/ml).

Further sesquiterpene pyridine alkaloids from Maytenus aquifolium

Two new sesquiterpene evoninate alkaloids, aquifoliunine E-III and aquifoliunine E-IV, were isolated from the root bark of Maytenus aquifolium. The structures of the new compounds were elucidated on the basis of spectroscopic methods, including ES-MS.

Electrospray ionization mass spectrometry screening of piperidine alkaloids from Senna spectabilis (Fabaceae) extracts: Fast identification of new constituents and co-metabolites

The fragmentation pattern of a homologous series of piperidine alkaloids isolated from S. spectabilis was investigated using electrospray ionization tandem mass spectrometry (ESI-MS/MS). The ESI-MS and ESI-MS/MS analyses of EtOH extracts and fractions from flowers and fruits of S. spectabilis allowed to elucidate the structures of four new compounds. The identification of these co-metabolites, based on the fragmentation patterns of previously isolated compounds, and further confirmed by accurate mass spectrometry defines this technique as a powerful tool to determine the metabolomic profile of species which has pharmacological importance. ©2005 Sociedade Brasileira de Química.

Intraspecific and intracolonial variation in the profile of venom alkaloids and cuticular hydrocarbons of the fire ant Solenopsis saevissima smith (Hymenoptera: Formicidae)

Fire ants are aggressive Neotropical ants that are extensively similar in general biology and morphology, making species identification difficult. Some fire ant species are top-rated pests spreading throughout the world by trade vessels. Many researchers attempted to sort between invasive and native species by using chemical characters, including patterns of venom alkaloids. The present study is the first to report intraspecific variation in some chemical characters, namely, cuticular hydrocarbons and venom alkaloids, within the Brazilian fire ant species Solenopsis saevissima and also reports on within-nest variations among members of different castes. Two different haplotypes (cryptic species) of S. saevissima were clearly identified, one presenting a predominant combination of the venom alkaloids cis- and trans-2-methyl-6-undecylpiperidine with the cuticular hydrocarbons C23, 3-Me-C23, 10-C 25:1, C25, and 3-Me-C25, and the other a predominant combination of cis- and trans-2-methyl-6-tridecenylpiperidine with predominance of 12-C25:1, C25, 11-Me-C25, 3-Me-C25, 13-C27:1, C27, and 13-Me-C 27. Intranest variations revealed that the proportions among these compounds varied sensibly among workers of different sizes, gynes, and males (no alkaloids were detected in the latter). Larva contained vestiges of the same compounds. The recorded chemical profiles are quite different from previous reports with S. saevissima samples from So Paulo. The finds thus support other recent claims that S. saevissima includes cryptic species; the study, moreover, adds the find that they can occur in the same geographical location. © 2012 Eduardo Gonalves Paterson Fox et al.

Solanidane and iminosolanidane alkaloids from Solanum campaniforme

From the leaves of Solanum campaniforme (Solanaceae), eight solanidane alkaloids were isolated, four of which contain a p-hydroxyphenylethylamine unit. Their structures were established as: 22β,23β-epoxy-solanida-1,4-dien-3-one; 22α,23α-epoxy-10-epi-solanida-1,4,9-trien-3-one; 22α,23α-epoxy-solanida-4-en-3-one; 22β,23β-epoxy-solanida-4-en-3-one; (E)-N-[8′(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4,9-trien-3-imine; (E)-N-[8′(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4-dien-3-imine; (Z)-N-[8′(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4,9-trien-3-imine and (Z)-N-[8′(4-hydroxyphenyl)ethyl]-22α,23α-epoxy-solanida-1,4-dien-3-imine. All structures were determined using spectroscopic techniques, such as 1D and 2D NMR, and HRESIMS. The cytotoxicity and the antiophidic activities of the alkaloids were evaluated. The alkaloids did not show any cytotoxicity, but inhibited the main toxic actions of Bothrops pauloensis venom. © 2013 Elsevier Ltd. All rights reserved.