Minor alkaloids of Glaucium flavum

Daskalova, Elmira; Iskrenova, E.; Kiryakov, H. G.; Evstatieva, L.

doi:10.1016/0031-9422(88)84134-7

Cited by 16 publications

(10 citation statements)

References 16 publications

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“…Studies on chemical composition of G. flavium have identified several isoquinoline alkaloids of the aporphine class such as glaucine, pontevedrine, oxoglaucine, and catalane which were isolated from the aerial plant parts (Arafa et al, 2016). In an earlier study of Daskalova et al (1988), ethanolic extracts of aerial parts at full blossom, revealed the presence of some minor alkaloids, namely dihydropontevedrine, dihydrosanguinarine, dihydrochelerythrine and dihydrochelirubine, while Petitto et al (2010) identified apart from glaucine, talikmidine, isocorydine and norisocorydine (Fig. 1c).…”

Section: Chemical Compositionmentioning

confidence: 81%

Halophytic herbs of the Mediterranean basin: An alternative approach to health

Petropoulos

Karkanis

Martins

et al. 2018

Food and Chemical Toxicology

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Wild native species are usually grown under severe and stressful conditions, while a special category includes halophytic species that are tolerant to high salinity levels. Native halophytes are valuable sources of bioactive molecules whose content is higher in saline than normal conditions, since the adaptation to salinity mechanisms involve apart from changes in physiological functions the biosynthesis of protectant molecules. These compounds include secondary metabolites with several beneficial health effects which have been known since ancient times and used for medicinal purposes. Recent trends in pharmaceutical industry suggest the use of natural compounds as alternative to synthetic ones, with native herbs being strong candidates for this purpose due to their increased and variable content in health promoting compounds. In this review, an introductory section about the importance of native herbs and halophyte species for traditional and modern medicine will be presented. A list of the most important halophytes of the Mediterranean basin will follow, with special focus on their chemical composition and their reported by clinical and ethnopharmacological studies health effects. The review concludes by suggesting future requirements and perspectives for further exploitation of these valuable species within the context of sustainability and climate change.

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Section: Chemical Compositionmentioning

confidence: 81%

Halophytic herbs of the Mediterranean basin: An alternative approach to health

Petropoulos

Karkanis

Martins

et al. 2018

Food and Chemical Toxicology

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“…The alkaloid root extract showed the most potent effect and using HPLC analysis, we demonstrated the presence of protopine as the major alkaloid in this extract. It has been reported earlier that the aerial part of this plant is very rich in isoquinoline alkaloids, principally the aporphine base S -(+)-glaucine (C 21 H 25 NO 4 ) [ 11 , 12 ]. The amount of glaucine in yellow horn poppy grass has been previously determined by HPLC analysis [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Identification and Quantification of the Main Active Anticancer Alkaloids from the Root of Glaucium flavum

Bournine

Bensalem

Wauters

et al. 2013

IJMS

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Glaucium flavum is used in Algerian folk medicine to remove warts (benign tumors). Its local appellations are Cheqiq el-asfar and Qarn el-djedyane. We have recently reported the anti-tumoral activity of Glaucium flavum root alkaloid extract against human cancer cells, in vitro and in vivo. The principal identified alkaloid in the extract was protopine. This study aims to determine which component(s) of Glaucium flavum root extract might possess potent antitumor activity on human cancer cells. Quantitative estimation of Glaucium flavum alkaloids was realized by HPLC-DAD. Glaucium flavum effect on human normal and cancer cell viability was determined using WST-1 assay. Quantification of alkaloids in Glaucium flavum revealed that the dried root part contained 0.84% of protopine and 0.07% of bocconoline (w/w), while the dried aerial part contained only 0.08% of protopine, glaucine as the main alkaloid, and no bocconoline. In vitro evaluation of the growth inhibitory activity on breast cancer and normal cells demonstrated that purified protopine did not reproduce the full cytotoxic activity of the alkaloid root extract on cancer cell lines. On the other hand, bocconoline inhibited strongly the viability of cancer cells with an IC50 of 7.8 μM and only a low cytotoxic effect was observed against normal human cells. Our results showed for the first time that protopine is the major root alkaloid of Glaucium flavum. Finally, we are the first to demonstrate a specific anticancer effect of Glaucium flavum root extract against breast cancer cells, which can be attributed, at least in part, to bocconoline.

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“…HPLC-UV analysis showed that glaucine predominates in aerial organs, whereas protopine occurs mostly in roots (Bournine et al, 2013). Isocorydine, an aporphine alkaloid with one free hydroxyl group, has also been reported in G. flavum (Daskalova et al, 1988;Peled et al, 1988;Kintsurashvili and Vachnadze 2000;Petitto et al, 2010;). Our highresolution, FTMS analysis provided unequivocal confirmation of the alkaloid profile in G. flavum, with glaucine found predominantly in aerial organs (Fig.…”

Section: Preferred (Rs)-6-o-laudanosoline and (Rs)-6-omethyllaudanomentioning

confidence: 99%

Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum

2015

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Transcriptome resources for the medicinal plant Glaucium flavum were searched for orthologs showing identity with characterized O-methyltransferases (OMTs) involved in benzylisoquinoline alkaloid biosynthesis. Seven recombinant proteins were functionally tested using the signature alkaloid substrates for six OMTs: norlaudanosoline 6-OMT, 6-O-methyllaudanosoline 49-OMT, reticuline 7-OMT, norreticuline 7-OMT, scoulerine 9-OMT, and tetrahydrocolumbamine OMT. A notable alkaloid in yellow horned poppy (G. flavum [GFL]) is the aporphine alkaloid glaucine, which displays C8-C69 coupling and four O-methyl groups at C6, C7, C39, and C49 as numbered on the 1-benzylisoquinoline scaffold. Three recombinant enzymes accepted 1-benzylisoquinolines with differential substrate and regiospecificity. GFLOMT2 displayed the highest amino acid sequence identity with norlaudanosoline 6-OMT, showed a preference for the 6-O-methylation of norlaudanosoline, and O-methylated the 39 and 49 hydroxyl groups of certain alkaloids. GFLOMT1 showed the highest sequence identity with 6-O-methyllaudanosoline 49OMT and catalyzed the 6-O-methylation of norlaudanosoline, but more efficiently 49-O-methylated the GFLOMT2 reaction product 6-O-methylnorlaudanosoline and its N-methylated derivative 6-O-methyllaudanosoline. GFLOMT1 also effectively 39-O-methylated both reticuline and norreticuline. GFLOMT6 was most similar to scoulerine 9-OMT and efficiently catalyzed both 39-and 79-O-methylations of several 1-benzylisoquinolines, with a preference for N-methylated substrates. All active enzymes accepted scoulerine and tetrahydrocolumbamine. Exogenous norlaudanosoline was converted to tetra-O-methylated laudanosine using combinations of Escherichia coli producing (1) GFLOMT1, (2) either GFLOMT2 or GFLOMT6, and (3) coclaurine N-methyltransferase from Coptis japonica. Expression profiles of GFLOMT1, GFLOMT2, and GFLOMT6 in different plant organs were in agreement with the O-methylation patterns of alkaloids in G. flavum determined by high-resolution, Fourier-transform mass spectrometry.

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Minor alkaloids of Glaucium flavum

Cited by 16 publications

References 16 publications

Halophytic herbs of the Mediterranean basin: An alternative approach to health

Halophytic herbs of the Mediterranean basin: An alternative approach to health

Identification and Quantification of the Main Active Anticancer Alkaloids from the Root of Glaucium flavum

Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum

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