On-line identification of tropane alkaloids from Erythroxylum vacciniifolium by liquid chromatography-UV detection-multiple mass spectrometry and liquid chromatography-nuclear magnetic resonance spectrometry.

The bark of catuaba (Erythroxylum vacciniifolium Martius, Erythroxylaceae), a tree native to the northern part of Brazil, was investigated for its alkaloid content. With the aim of obtaining preliminary structure information on-line, the alkaloid extract was analysed by high-performance liquid chromatography coupled to diode array UV detection, to mass spectrometry and to nuclear magnetic resonance. Interpretation of on-line spectroscopic data obtained from this extract led to structural elucidation of six new alkaloids and partial identification of 18 potentially original alkaloids bearing the same tropane skeleton esterified in positions 3 and 6 by 1-methyl-1H-pyrrol-2-carboxylic acid and/or 4-hydroxy-3,5-dimethoxybenzoic acid.

A new bistetrahydrofuran acetogenin from the roots of Annona salzmanii.

A new bistetrahydrofuran acetogenin, salzmanin (1), was isolated from the MeOH extract of Annona salzmanii, in addition to the known compounds, squamocin, almunequin, bullatalicin, and annonacin. The structure of 1 was elucidated by spectroscopic methods, including LSIMS-MS technique, and confirmed by a chemical transformation. The cytotoxic activity of 1 and squamocin was investigated.

Antinociceptive effect in mice of a hydroalcoholic extract of Neurolaena lobata (L.) R. Br. and its organic fractions.

An infusion of the aerial parts of Neurolaena lobata (L.) R. Br. (Compositae-Asteraceae) is used in Caribbean folk medicine to treat several kinds of pain. In this investigation we studied the acute oral toxicity of the hydroalcoholic extract of the plant and the antinociceptive effect of the extract and of its hexane- and chloroform-partitioned fractions, given orally, in nociception and inflammatory models in mice. No signs of toxicity were observed for oral doses up to 5000 mg kg(-1) in mice. Morphine hydrochloride (100 mg kg(-1)), dipyrone sodium (200 mg kg(-1)), the hydroalcoholic extract (1000 mg kg(-1)), and its chloroform- and hexane-partitioned fractions (100 mg kg(-1)) significantly inhibited acetic acid-induced abdominal constriction in mice (100, 95, 47, 62 and 60% inhibition, respectively when compared with the negative control). In the hot-plate test in mice, morphine hydrochloride, the chloroform- and hexane-partitioned fractions, but not the hydroalcoholic extract, resulted in a significant latency increase in all observation times. In the acetic acid-induced abdominal constriction in mice, pretreatment of the animals with naloxone significantly reversed the analgesic effect of morphine, but not that of the hydroalcoholic extract or of its hexane- and chloroform-partitioned fractions. Finally, administration of the hexane- and chloroform-partitioned fractions (100 mg kg(-1)) had a significant anti-oedematogenic effect on carrageenan-induced oedema in mice. These data show that the hydroalcoholic extract of N. lobata and, in particular, its partitioned fractions have significant analgesic properties when assessed through these pain models. Their antinociceptive effect might be the result of interference with the inflammatory process.

Pessoine and spinosine, two catecholic berbines from Annona spinescens.

The trunk bark and roots of Annona spinescens have been investigated for their alkaloid content. Two new berbine alkaloids, pessoine (1) and spinosine (2), have been isolated from the bark, and their structures were elucidated by spectroscopic methods. Eight known isoquinoline alkaloids were also obtained. The trypanocidal and antileishmanial activities of these isolated compounds have been investigated.

In vitro antifungal activity of essential oils obtained from officinal plants against dermatophytes.

Thirteen essential oils were isolated from officinal plants and tested in vitro against dermatophyte strains isolated from patients with dermatophytosis. Of the tested oils, those obtained from Cinnamomum zeylanicum, Ocimum gratissimum, Cymbopogon citratus, Eugenia uniflora and Alpinia speciosa were found to be the most active, inhibiting 80% of the dermatophyte strains tested and producing inhibition zones more than 10 mm in diameter.

Chemical and pharmacological investigation of Solanum species of Brazil--a search for solasodine and other potentially useful therapeutic agents.

A systematic search for solasodine, an important starting material for the partial synthesis of steroidal hormones as well as other potentially bioactive constituents of various Solanum species of Brazil has been undertaken. Thus, the fruits of S. paludosum, S. asperum, S. sessiliflorum and Solanum sp. were found to contain significant amounts of solasodine. The root bark of S. paludosum which showed curare like activity yielded tomatidenol and another yet unidentified alkaloid responsible for the biological activity. The fruits of S. asperum yielded a new spirosolane alkaloid, solaparnaine. The stem bark of S. pseudo-quina showed convulsive and excitatory activity from which (25S)-isosolafloridine was identified as the active principle. In addition, the latter alkaloid was also found to show antimicrobial activity.

Chemical and pharmacological investigation of Solanum species of Brazil: a search for solasodine and other potentially useful therapeutic agents

A systematic search for solasodine, an important staring material for the partial synthesis of steroidal hormones as well as other potentially bioactive constituents of various Solanum species of Brazil has been undertaken. Thus, the fruits of S. paludosum, S. asperum, S. sessiliforum and Solanum sp. were found to contain significant amounts of solasodine. The root bark of S. paludosum which showe durare like activity yelded tomatidenol and another yet unidentified alkaloid responsible for the biological activity. The fruits of S. asperum yelded a new spirosolane alkaloid, solaparnaine. The stem bark of S. pseudo-quina showed convulsive and exitatory activity from which (25S)-isosolafloridine was identified as the active principle. In addition, the latter alkaloid was also found to show antimicrobial activity.