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Heliotropium crassifolium Boiss, (Boraginaceae) from a population of Ilam, western region of Iran was studied for pyrrolizidine alklaoids (PAs). Four alkaloids have been identified: europine 1, europine N-oxide 2 and a new pyrrolizidine alkaloids ilamine 3 and its N-oxide 4, respectively. Their structures were elucidated by IR, 1H-NMR and EIMS data.
Total reactive antioxidant potential (TRAP) of resinous exudates from Heliotropium species was evaluated by measuring the bleaching of stable free radicals. The antioxidant capacity of the resinous exudates in Trolox equivalents, evaluated from the bleaching of ABTS derived radical cations, ranged from 2.0 M (H. huascoense) to 5.2 M (H. stenophyllum), indicating a very high concentration of phenolic compounds. Considerably smaller values were obtained by measuring the bleaching of DPPH radicals. The ratio between the values obtained employing ABTS derived radicals and DPPH, ranged from 37 (H. megalanthum) to 4.5 (H. chenopodiaceum variety typica). The magnitude of the difference can be considered as an indication of the relative reactivity of the antioxidants present in the exudates. Similar ratios were observed when stoichiometric coefficients were evaluated for representative purified flavonoids obtained from the resinous exudates.
Experimental pyrrolizidine alkaloid intoxication was produced in inbred Swiss mice. Animals were fed diets containing 0, 1, 3, 5, or 10% Heliotropium dolosum seed for 24 w. The seeds contained 0.13% total alkaloid concentration composed of 4 specific components: lasiocarpine (78.79%), heliosupine (11.96%), echimidine (5.43%), and heliotrine (3.82%). Deaths occurred in all dosed groups and increased with dietary seed concentration. Massive to submassive liver necrosis together with sinusoidal congestion, and hemorrhage or multifocal hepatocytic necrosis was limited to animals which survived < 5 w and were fed on 10% seed. Moderate to severe hepatomegalocytosis, scattered single cell necrosis, and mild subcapsuler fibrosis were seen in all test group animals that survived > 5 w. Intranuclear eosinophilic inclusions in hepatocytes and bile duct and ductular cell hyperplasia were the most noticeable lesions in the 1, 3, and 5% groups. There was mild to moderate renal tubular megalocytosis in the 3, 5, and 10% groups. It seems likely that H dolosum seed, at least to a limited extent, constitutes a health hazard for certain animal species.
The disease produced by feeding chickens and ducks a commercial poultry feed containing heliotrine and lasiocarpine, pyrrolizidine alkaloids of Heliotropium europaeum, is described. Illthrift, ascites and degenerative lesions in the liver were the major findings. Similar lesions occurred in chickens fed a diet containing H. europaeum. The source of the alkaloids in commercial poultry feed was probably the seeds of H. europaeum harvested with wheat.
Investigation of the alkaloidal constituents of Heliotropium digynum resulted in the isolation of four alkaloids viz. heliotrine, europine, lasiocarpine and 7-angelylheliotrine. Moreover, HPLC and GLC showed the probable presence of heliotridine and some other unidentified minor constituents. A summary of the pharmacotoxicity and biological activity of the ethanolic extract, total alkaloids with special reference to heliotrine is presented.
Twenty-four hour ip median lethal doses (LD50) of freeze-dried aqueous extracts of Heliotropium scottae Rendle leaves and stems in mice were determined and clinical signs noted. The LD50 of the leaf extract was 3.0 g/kg, while that of the stems was 3.5 g/kg. Clinical signs were excitement, prostration, rapid breathing, gasping for breath and death. The signs were the same for both the leaf and stem extracts. It was concluded that both the leaves and stems of H scottae have slight acute toxicity.
Extracts of Heliotropium indicum Linn. (Boraginaceae) showed significant activity in several experimental tumor systems. The active principle is isolated and shown to be the N-oxide of the alkaloid, indicine, previously isolated from this plant. Supporting structural data and anti-tumor data are provided.
Seven sterols and triterpenoids have been isolated from H. ellipticum and tested for their antimicrobial activity.
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Five groups of 30 male Japanese quail, each 7-w-old, were fed diets containing 0, 1, 3, 5, or 10% (w/w) of dehulled H dolosum seed. Half of the birds from the each group were killed at 6 and 24 w after beginning of the trial. At the end of 6th w, neither mortality nor clinical sign occurred in test groups. In the 5 and 10% inclusion levels, mild to moderate hepatic injury was detected as evidenced by mild karyomegaly, moderate fatty change, focal or portal fibrosis, bile duct hyperplasie, and ovalocyte proliferation along with lower serum protein and albumin levels. By the termination of the experiment (24 w), 5 birds died in the 10% dosed group. Hepatic cirrhosis was the most prominent finding in the 5 and 10% group; at these levels, serum protein and albumin values decreased significanty while billuribin and ALP levels increased. Based on relative weights and histological evaluations, testicularatrophywasdosedependent. These results partly affirm earlier studies that the quail is highly resistant to the toxic effects of H dolosumseed. However, the resistance to H dolosum is less than Senecio Jacobae and Crotalaria spectabilis when considering tissue injury.
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