Dehydroglaucine

Antiplatelet aggregation constituents from Annona purpurea.[Pubmed:9868142]

J Nat Prod. 1998 Dec;61(12):1457-61.

Bioactivity-directed fractionation led to the isolation of 19 compounds, including three oxoaporphines, oxopurpureine (5), oxonuciferine (6), and oxoglaucine (7); three aporphines, (+)-predicentrine (8), (-)-glaucine (9), and thalbaicalidine (10); one aporphine sensu stricto, N-formyl-purpureine (11); one proaporphine, glaziovine; one phenanthrene, thalicpureine (12); two 6a,7-dehydroaporphines, dehydrolirinidine (13) and 7-hydroxy-Dehydroglaucine (14); four flavonoids, quercetin-3-O-rhamnoside, kaempferol-3-O-rhamnoside, isorhamnetin-3-O-rhamnoside, and tanarixetin-3-O-rhamnoside; one purine, adenine; one lactam amide, squamolone; and two steroids, beta-sitosterol and beta-sitosterol-beta-D-glucoside from the MeOH extract of the leaves of Formosan Annona purpurea. Among them, 11-14 were characterized as new compounds and alkaloids, 5-8, 10, and 12-14 exhibited significant antiplatelet aggregation activity.

Glaucine analogues as inhibitors of mouse splenocyte activity.[Pubmed:9812336]

Pharmazie. 1998 Oct;53(10):694-8.

The inhibitory effect of 15 semi-synthetic analogues of glaucine (1) on the lipopolysaccharide (LPS)-induced and the concanavalin A (Con A)-induced proliferation of mouse splenocytes was compared in vitro. Isoboldine (3), bracteoline (4) and Dehydroglaucine (9) showed a significantly higher potency to suppress LPS-induced proliferation than 1, while 7-hydroxy-4-methylglaucine (8), 7-formylDehydroglaucine (11), 7-acetylDehydroglaucine (13), 7-benzoylDehydroglaucine (14), oxoglaucine (15) and glaucine-quinol (16) were less inhibitory. Compounds 3, 4, boldine (5), 15 and 16 surpassed significantly the inhibition expressed by 1 on Con A-induced proliferative response. The effect was equal to the inhibition determined for mitomycin C (Mit C) with both mitogens. In contrast to all others analogues, thaliporphine (2) stimulated splenocyte proliferation in both assays. Antibody response against sheep red blood cells (SRBC) was lowered most strongly by cataline (6), 7-methylDehydroglaucine (10) and 16.

Comparative study of the hypotensive effect of a group of structural derivatives of glaucine.[Pubmed:1819921]

Acta Physiol Pharmacol Bulg. 1991;17(2-3):98-103.

A comparative study was made on the hypotensive effect of a group of dehydrogenated structural derivatives of the alkaloid glaucine. The compounds studied induced a slowly occurring marked decrease in the blood pressure. Applied intravenously, they did not manifest the initial brief and very pronounced phase of the hypotensive effect, typical of glaucine, and failed to change substantially the respiration and the cardiac activity of the experimental animals. The most marked hypotensive effect was demonstrated by 7-benzoyl-Dehydroglaucine (DG4), which reduced the blood pressure by about 50 and 60% respectively, when applied in doses of 1 mg/kg and 2.5 mg/kg. Applied duodenally, the dehydrogenated glaucine derivatives also manifested a gradually occurring hypotensive effect, whereby DG4 again caused the most pronounced blood pressure drop. Depending on the DG4 and glaucine doses used, the pressor effects of noradrenaline (NA) and nicotine (NIC) were moderately to strongly suppressed or completely inhibited. In experiments on cat membrana nictitans glaucine also suppressed moderately (2.5 mg/kg) or markedly (5 mg/kg) the contractile effects of NIC and NA, while DG4 did not influence (1 mg/kg) or potentiated (2.5 mg/kg) these effects.

Minor Alkaloids of Corydalis bulbosa, Structure of Bulbodione.[Pubmed:17340280]

Planta Med. 1984 Apr;50(2):136-8.

As a result of the reinvestigation of the alkaloid content of CORYDALIS BULBOSA (L.) DC. (Papaveraceae), growing in Bulgaria, a new 8,11-dioxoaporphine alkaloid, named bulbodione, together with dihydrosanguinarine, Dehydroglaucine, (+/-)-sinactine, glaucinone and bicucullinine were isolated. These six alkaloids had not been detected in our initial study of the plant. The structure of buldodione was elucidated on the basis of spectral data and confirmed by synthesis of the alkaloid by means of Fremy's radical oxidation of bulbocapnine. The identification of the known alkaloids was obtained from their IR and (1)H-NMR spectral data and by direct comparison with authentic samples.

Pharmacological studies of a group of semi-synthetic structural analogues of glaucine.[Pubmed:543409]

Acta Physiol Pharmacol Bulg. 1979;5(4):3-12.

Glaucine and the newly-synthesized compounds possess some general properties conditioned by the common apomorphine structure - inhibition of the central nervous system, brief decrease in blood pressure and spasmolytic action. At the same time the changes in the structure of glaucine lead to quantitative or qualitative changes in some of its effects. Substitution of hydrogen in 3rd position with -CH2. NH-group reduces glaucine toxicity 3.5 times. Still greater decrease in the toxicity (7.5-10 times) is found in the case of N-oxidation or dehydrogenation of glaucine. The extension of the methyl group in 3rd position with a hydroxy group or with an amide residue of the benzoic acid, as well as the dehydrogenation and N-oxidation of glaucine, lead to intensification of the inhibitory action on the central nervous system. With the exception of 7-methyl Dehydroglaucine which has antitussive action similar to glaucine, the other glaucine structural analogues do not possess this property. Both glaucine and its structural analogues exercise a bronchoconstrictor effect. 3-Aminomethyl derivatives preserve the spasmolytic activity of glaucine, and their several-fold lower toxicity makes them more promising spasmolytic agents than glaucine. Dehydrogenation and N-oxidation of glaucine reduce considerably its spasmolytic action.

Two antimicrobial alkaloids from heartwood of Liriodendron tulipifera L.[Pubmed:807704]

J Pharm Sci. 1975 May;64(5):789-92.

Alcoholic extracts of the heartwood of Liriodendron tulipifera have demonstrated antimicrobial activity against Staphylococcus aureus, Mycobacterium smegmatis, Candida albicans, and Aspergillus niger. The antimicrobial activity was associated only with the alkaloidal fraction. Separation of the active alkaloidal fraction by chromatography led to the isolation and identification of Dehydroglaucine and liriodenine as the active components. Several other alkaloidal derivatives were prepared and tested. In addition to the active alkaloids, michelabine was also identified in the tertiary nonphenolic base fraction along with the lignan, lirioresinol-B-dimethyl ether, and two N-acetylnoraporphine alkaloids from the nonbasic fraction.