Dioflorin, a Minor Flavonoid from Dioclea grandiflora

Dioflorin (1) was isolated as a minor constituent from the rootbark of Dioclea grandiflora, the crude extract of which demonstrated analgesic activity. The structure of 1 has been determined to be 5,7,2'-trihydroxy-8-methoxy-6-(3-methyl-2-butenyl)flavanone on the basis of spectral analysis.

Analgesic effect of Dioclea grandiflora constituents in rodents.

An aqueous fraction and dioclein (5,2',5'-trihydroxy-6,7-dimethoxyflavanone) obtained from the ethanolic extract of the Dioclea grandiflora were tested for their analgesic effect in mice and rats employing acetic-induced writhing and tail flick tests, respectively. When administered intraperitoneally the two agents exhibited significant analgesic effects. The activity of both dioclein and aqueous fraction apparently involves an opiate-like mechanism, since their analgesic action was attenuated by naloxone pretreatment.

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.

Convulsive action of (25S)-isosolafloridine isolated from Solanum pseudo-quina bark.

The crude ethanolic extract prepared from the stem bark of Solanum pseudo-quina produced excitatory effects dominated by convulsions in rats and mice. Solvent extraction followed by alumina column chromatography resulted in the isolation of a pharmacologically active material (AP) which was identified to be (25S)-isosolafloridine. The convulsions produced by AP were predominantly clonic and invariably preceded by generalized fine and coarse tremors. This convulsive behaviour did not entirely resemble the convulsions produced by strychnine, pentylenetetrazol, bicuculline, picrotoxin or 3-mercaptopropionic acid. The tremor and convulsions were only slightly affected by drugs interfering with cholinergic, catecholaminergic, serotoninergic or encephalinergic neurotransmission. Only diazepam and particularly gamma-vinyl-GABA blocked AP-induced effects. After section of the spinal cord at a mid-theoretic level, AP produced convulsions only in the anterior part of the body. After intracerebroventricular administration, AP produced only sedation. A depressive effect was also observed on the blood pressure of conscious rats before and after the convulsions. In subconvulsive doses AP enhanced spontaneous motor activity in mice.