20068-96-6

Upstream product

• 35587-63-4 O-acetylthaliporphine 
• 371196-15-5 N-formyl-laurolitsine 
• 5630-11-5 (+/-)-glaucine 
• 475-81-0 glaucine 
• 71609-80-8 epiglaufidine 
• 51015-10-2 (+/-)-N-ethoxycarbonylnorthaliporphine 
• 371196-16-6 (6aS)-4,5,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6H-dibenzo[de,g]quinoline-6-carbaldehyde 
• 5890-18-6 (+)-norboldine 

Relevant academic research and scientific papers

ALKALOIDS OF Glaucium fimbrilligerum. II

The alkaloids of the epigeal part and roots of the plant Glaucium fimbrilligerum have been studied.A total of 18 alkaloids has been isolated, of which epiglaufidine proved to be new, and its structure has been established.Columbamine has been isolated from the genus Glaucium for the first time, and magnoflorine and stilopine α-hydroxymethylate from this species of plant for the first time.

BIOSYNTHESIS OF THALICARPINE IN THALICTRUM MINUS

Feeding experiments with 14C-labelled reticuline, protosinomenine, orientaline, their N-nor-analogues and 3H-labelled isoboldine have shown reticuline and isoboldine to be the most efficient precursors of thalicarpine in Thalictrum minus.A biosynthetic pathway for thalicarpine with reticuline and isoboldine at the benzylisoquinoline and aporphine stages respectively has been suggested.Support for this proposal has been provided by the demonstration by radioisotopic dilution that reticuline and isoboldine are minor constituents of the plant.Key Word Index - Thalictrum minus; Ranuncula ceae; biosynthesis; alkaloids; thalicarpine; reticuline; isoboldine.

Thaliporphine increases survival rate and attenuates multiple organ injury in LPS-induced endotoxaemia

This study addressed the question of whether thaliporphine, a phenolic aporphine alkaloid obtained from Chinese herbs and possessing antioxidant and α-1 adrenoceptor antagonistic activity, has protective effects in endotoxaemic rats and we attempted to elucidate the mechanisms contributing to such protective effects. Injection of rats with endotoxin (E. coli lipopolysaccharide, LPS) induced severe hypotension and tachycardia as well as vascular hyporeactivity to noradrenaline. Pretreatment of LPS-treated rats with thaliporphine attenuated the delayed hypotension significantly whilst only a higher dose (1 mg/kg) of thaliporphine decreased LPS-induced tachycardia. LPS significantly increased nitric oxide (NO.) and superoxide anion (O2-.) levels, a response that was reduced by pretreatment with 1 mg/kg thaliporphine. Endotoxaemia for 240 min resulted in a bell-shaped time course for the change of serum tumour necrosis factor-α (TNF-α) level with a peak at 60 min. Pretreatment of LPS-treated rats with 1 mg/kg thaliporphine significantly reduced the serum TNF-α level at 60 min. In addition, LPS caused a biphasic change in blood glucose and thaliporphine attenuated the late-phase decrease in blood glucose. Endotoxaemia induced multiple organ injury in the liver, kidney and heart, as indicated by increases of aspartate aminotransferase (GOT), alanine aminotransferase (GPT), creatinine (CRE), lactate dehydrogenase (LDH) and creatine phosphate kinase muscle-brain (CKMB) levels in serum. These increases of biochemical markers and inflammatory cell infiltration into injured tissues were reduced significantly by treatment with thaliporphine. In addition, thaliporphine increased the survival rate of LPS-treated mice dose-dependently. In conclusion, our results suggest that thaliporphine could be a novel agent for attenuating endotoxin-induced circulatory failure and multiple organ injury and may increase the survival rate. These beneficial effects of thaliporphine may be attributed to the suppression of TNF-α, NO. and O2-. production. Springer-Verlag 2005.

Semisynthesis and myocardial activity of thaliporphine N-homologues

The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from laurolitsine (1), an abundant aporphine present in Phoebe formosana. Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (±)-wilsonirine. 1H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution. Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.

LIPASE-CATALYZED RESOLUTION OF ACETATES OF RACEMIC PHENOLIC APORPHINES AND HOMOAPORPHINES IN ORGANIC SOLVENT

Enzymatic resolution of (+/-)-1-acetoxy-2,9,10-trimethoxyaporphine (O-acetylthaliporphine) (3), (+/-)-2-acetoxy-1,9,10-trimethoxyaporphine (O-acetylpredicentrine) (4), and (+/-)-3-acetoxy-2,9,10-trimethoxyaporphines (5) by use of immobilized lipase in organic solvent gave resolved 3-5 and the corresponding hydroxyaporphines (9-11) in fair to good chemical and optical yields.Analogous reaction of (+/-)-1-acetoxy-2,10,11-trimethoxyhomoaporphine (6) did not take place, whereas that of (+/-)-2-acetoxy-1,10,11-trimethoxy- and (+/-)-3-acetoxy-1,10,11-trimethoxyhomoaporhines (7 and 8) produced optical active 7, 8 and hydroxyhomoaporphines (13,14).

PHOTOCHEMICAL SYNTHESIS OF APORPHINES: (+/-)-THALIPORPHINE, (+/-)-N-METHYLLAUROTETANINE AND (+/-)-ISOBOLDINE.

Aporphines, (+/-)-thaliporphine (1), (+/-)-N-methyllaurotetaline (2), and (+/-)-isoboldine (3) were synthesised using photochemical cyclization as the key step.

THE DEMETHYLATION OF APORPHINES WITH SULFURIC ACID

Sulfuric acid at room temperature has been found a useful reagent for interconverting aporphine alkaloids by selective O-demethylation.This was controlled by electronic or steric effects.

Synthesis of hernandaline

There is disclosed a novel and improved method of synthesizing aporphines utilizing the Pschorr cyclization of 1-(2'-aminobenzyl)-7 hydroxy-1,2,3,4-tetrahydroisoquinolines in place of the corresponding 7-methoxy compounds. In the novel process of the present invention the amino group is diazotized and cyclized in the presence of copper powder.