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Alkaloids of Thalictrum. XXII. Isolation of alkaloids with hypotensive and antimicrobial activity from Thalictrum revolutum.

Sixteen alkaloids were characterized from Thalictrum revolutum DC., namely; thalidasine, O-methylthalmethine, O-methylthalicberine, thalrugosaminine, thalicarpine, thalmelatine, pennsylvanine, palmatine, berberine, thalifendine, columbamine, jatrorrhizine, deoxythalidastine, thalphenine and magnoflorine. The structure of thairugosaminine (1) a bisbenzylisoquinoline type which was previously proposed on partial data was completely established, including the absolute configuration as S,S. Thalphenine, thalidasine, O-methylthalicberine, thalicarpine, thalrugosaminine and thaliglucinone were found to possess hypotensive activity in rabbits. Thalrugosaminine, thalicarpine, thalmelatine, O-methylthalmethine, pennsylvanine and thalphenine were found to be active against Mycobacterium smegmatis.

Alkaloids↗

Alkaloids of Thalictrum. XXI. Isolation and characterization of alkaloids from the roots of Thalictrum podocarpum.

Thirteen alkaloids, hernandezine, thalidezine, N-desmethylthalidezine, isothalidezine, thalistyline, thalistyline methodiiodide, N-desemethylthalistyline, berberine, columbamine, jatrorrhizine, palmatine, thalifendine, magnoflorine and the artifact, 8-trichloromethyldihydroberberine were isolated from the roots of Thalictrum podocarpum Humb. In addition, oxyberberine and thaliglucinone were obtained in very minor amounts and identified by tlc. Of these compounds, N-desmethylthalidezine and isothalidezine are new bisbenzylisoquinoline alkaloids. Sucrose was isolated from the alcoholic extract. Hernandezine, thalistyline, thalidezine, thalistyline methodiiodide and N-desmethylthalistyline were found to possess antimicrobial activity against Mycobacterium smegmatis at concentrations of 100 microgram/ml or less.

Alkaloids↗

Alkaloids of thalictrum. XX. Isolation, identification and structural elucidation of the alkaloids of the root of Thalictrum longistylum.

A study of the alkaloids of the roots of Thalictrum longistylum DC. resulted in the isolation of 12 alkaloids plus an artifact, 8-trichloromethyldihydroberberine. The 12 alkaloids were berberine, columbamine, jatrorrhizine, magnoflorine, methothalistyline, N-desmethylthalistyline, oxyberberine, palmatine, thalibrine, thalifendine, thaliglucinone, and thalistyline. Of these alkaloids, methothalistyline, N-desmethylthalistyline, and thalistyline are new compounds and with thaliglucinone possess hypotensive activity in dogs and rabbits. Methothalistyline, N-demethylthalistyline, thalistyline, and thalibrine were found to be active against Staphylococcus aureus and Mycobacterium smegmatis with with thalistyline being most active (50 microgram/ml).

Alkaloids↗

Alkaloids of Thalictrum. XV. Isolation and identification of the hypotensive alkaloids of the root of Thalictrum lucidum.

Sixteen alkaloids, namely homoaromoline, obaberine, O-methyl-thalicberine, oxyberberine, thalidasine, thaliglucinone, thalrugosine, obamegine, oxyacanthine, berberine, columbamine, jatrorrhizine, magnoflorine, palmatine, thalifendine and base A chloride, plus the artifact, 8-trichloromethyldihydroberberine, were isolated from the alkaloid fraction of the roots of Thalictrum lucidum L. Of these, obamegine, thalrugosine, O-methylthalicberine, thaliglucinone, obaberine and homoaromoline were found to possess hypotensive activity in normotensive dogs. Thalidasine, homoaromoline, thalrugosine, thaliglucinone, obamegine, jatrorrhizine, and columbamine were found to possess antimicrobial activity against Mycobacterium smegmatis at a concentration of 100 mug/ml or less.

Alkaloids↗

Alkaloids of Thalictrum XXVI. New hypotensive and other alkaloids from Thalictrum minus race B.

The roots of T. minus race B have yielded 9 alkaloids, thalirabine (1), thaliracebine (13), thalfine (19), thalfinine (20), thalrugosaminine (22), thalidasine (13), obaberine (24), thaliglucinone (25) and (S)-reticuline (26). The first two, possessing marked hypotensive activity, were assigned complete structures by physical and chemical methods. Thalfine (19) was given S-configuration at its one asymmetric center and was converted to thalfinine (20) and epithalfinine (21), thus the stereochemistry was established at one of the two optically active positions. The other alkaloids were identified by direct comparison with known samples. Antimicrobial testing showed thalirabine, thaliracebine, thalfine, and thalfinine to be active against Mycobacterium smegmatis.

Alkaloids↗

Alkaloids of Thalictrum XXVII. New hypotensive aporphine-benzylisoquinoline derived dimeric alkaloids from Thalictrum minus race B.

The roots of T. minus race B have yielded, in addition to adiantifoline (1) previously isolated from this source, two new related alkaloids, thaliadine (2) and thaliadanine (5). Both were assigned complete structures by spectral methods and by chemical interconversion to adiantifoline or its product. O-Desmethyladiantifoline should have structure 14, rather than the previously reported 5. All three isolated alkaloids show hypotensive activity in rabbits, and thaliadanine (5) has antimicrobial activity against Mycobacterium smegmatis.

Alkaloids↗

Natural products from medicinal plants: non-alkaloidal natural constituents of the Thalictrum species.

Thalictrum is an important plant genus that is widely used in traditional medicine. In this review considerable attention has been given to triterpenoid saponins in connection with their specific distribution in the Thalictrum genus and with their biological activity. All other non-alkaloid compounds isolated from the Thalictrum genus are also reviewed; these metabolites are discussed in relation to their structural features and to their role in the plants.

Biological Products↗