Flavinantine

Cytotoxic Alkaloids from the Stem of Xylopia laevigata.[Pubmed:27399666]

Molecules. 2016 Jul 8;21(7). pii: molecules21070890.

Xylopia laevigata (Annonaceae), known locally as "meiu" or "pindaiba", is widely used in folk medicine in Northeastern Brazil. In the present work, we performed phytochemical analyses of the stem of X. laevigata, which led to the isolation of 19 alkaloids: (-)-roemerine, (+)-anonaine, lanuginosine, (+)-glaucine, (+)-xylopine, oxoglaucine, (+)-norglaucine, asimilobine, (-)-xylopinine, (+)-norpurpureine, (+)-N-methyllaurotetanine, (+)-norpredicentrine, (+)-discretine, (+)-calycinine, (+)-laurotetanine, (+)-reticuline, (-)-corytenchine, (+)-discretamine and (+)-Flavinantine. The in vitro cytotoxic activity toward the tumor cell lines B16-F10 (mouse melanoma), HepG2 (human hepatocellular carcinoma), K562 (human chronic myelocytic leukemia) and HL-60 (human promyelocytic leukemia) and non-tumor peripheral blood mononuclear cells (PBMCs) was tested using the Alamar Blue assay. Lanuginosine, (+)-xylopine and (+)-norglaucine had the highest cytotoxic activity. Additionally, the pro-apoptotic effects of lanuginosine and (+)-xylopine were investigated in HepG2 cells using light and fluorescence microscopies and flow cytometry-based assays. Cell morphology consistent with apoptosis and a marked phosphatidylserine externalization were observed in lanuginosine- and (+)-xylopine-treated cells, suggesting induction of apoptotic cell death. In addition, (+)-xylopine treatment caused G(2)/M cell cycle arrest in HepG2 cells. These data suggest that X. laevigata is a potential source for cytotoxic alkaloids.

Chemical and antiviral study on alkaloids from Papaver pseudocanescens M. Pop.[Pubmed:22486038]

Z Naturforsch C J Biosci. 2012 Jan-Feb;67(1-2):22-8.

The phytochemical investigation of the aerial parts of Papaver pseudocanescens M. Pop. of Mongolian origin resulted in the isolation and structural elucidation of 8 alkaloids of the isoquinoline and promorphinane type. 8,14-Dihydroamurine, 8,14-dihydroFlavinantine, and Flavinantine are promorphinanes. Alborine, mecambridine, and mecambridine methohydroxide are retroprotoberberines. Amurensinine is an isopavine alkaloid and O-methylarmepavine is a benzylisoquinoline alkaloid. O-Methylarmepavine is a new alkaloid for the genus Papaver. Promorphinane-type alkaloids have been found for the first time in the species. All structures were established by physical and spectral analysis. As a first attempt to describe some of the biological activities of these alkaloids, the antiviral effect was tested against the in vitro replication of several viruses which belong to different taxonomic groups and represent significant human pathogens. Based on the results, the conclusion could be drawn that particular alkaloids from P. pseudocanescens possess selective antiviral effects against the replication of poliovirus 1 and human rhinovirus 14, two viruses from the Enterovirus genus of the Picornaviridae family.

A new 8,14-dihydropromorphinane alkaloid from Papaver nudicaule L.[Pubmed:17763104]

Nat Prod Res. 2007 Jul 20;21(9):852-6.

A racem. 8,14-dihydroamurine is a new promorphinane alkaloid isolated from the aerial parts of Papaver nudicaule L. (Papaveraceae) of Mongolian origin. The known promorphinane and isopavine alkaloids (+)-amurine, (-)-amurensinine, (-)-O-methylthalisopavine, (-)-Flavinantine and (-)-amurensine were also described. All structures were established by physical and spectral analysis. Flavinantine has been found for the first time in the species.

Alkaloids from Croton flavens L. and their affinities to GABA-receptors.[Pubmed:14577695]

Nat Prod Res. 2003 Dec;17(6):437-40.

Phytochemical investigation of several plants of Croton flavens L. from Barbados has led to the isolation of the tetrahydroprotoberberine alkaloids scoulerine and coreximine, as well as the morphinanedienones salutaridine and its racemic form salutarine, sebiferine, norsinoacutine and Flavinantine. In a screening for 3H-GABA displacing activity coreximine showed the highest affinity to the GABA(A) receptor.

Croton ruizianus: platelet proaggregating activity of two new pregnane glycosides.[Pubmed:9544561]

J Nat Prod. 1998 Mar;61(3):318-22.

The MeOH extract of the aerial parts of Croton ruizianus afforded two new pregnane glycosides 1 and 2, together with the morphinandienone alkaloids Flavinantine (3) and O-methylFlavinantine (4). Their structures were elucidated by NMR experiments including 1H-1H (1D TOCSY and 2D DQF-COSY) and 1H-13C (HSQC, HMBC) spectroscopy. The proaggregating activity of the MeOH extract and the isolates were evaluated. Although the MeOH extract and pregnane glycosides (at different doses) were found to promote platelet aggregation, Flavinantine (3) and O-methylFlavinantine (4) showed only slight activity. The ability of the MeOH extract and the four compounds to act synergistically with thrombin was also evaluated. All the tested compounds were successful in augmenting the aggregating effect of thrombin, although to different degrees.