Chapter 1 Chemotaxonomy of Papaveraceae and Fumariaceae

Preininger, V.

doi:10.1016/s0099-9598(08)60246-1

Cited by 24 publications

(31 citation statements)

References 131 publications

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“…Among them cis-diamminedichloroplatinum II (cis-DDP), 1 organometallic compounds 2 and protoberberines 3,4 are worth mentioning. The medicinal value of protoberberine alkaloid found in the root, rhizome and stem bark of the Berberis vulgaris L. plant has been recognized from ancient times.…”

Section: Introductionmentioning

confidence: 99%

Quantum chemical and nuclear magnetic resonance spectral studies on molecular properties and electronic structure of berberine and berberrubine

Tripathi

Chauhan

Thankachan

et al. 2007

Magnetic Reson in Chemistry

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The structural and electronic properties of berberine and berberrubine have been studied extensively using density functional theory (DFT) employing B3LYP exchange correlation. The geometries of these molecules have been fully optimized at the B3LYP/6-311G** level. The chemical shift of 1H and 13C resonances in NMR spectra of these molecules have been calculated using the gauge invariant atomic model (GIAO) method as implemented in Gaussian 98. One- and two-dimensional HSQC (1H-13C), HMBC (1H-13C) and ROESY (1H-1H) spectra were recorded at 500 MHz for the berberine molecule in D(2)O solution. All proton and carbon resonances were unambiguously assigned, and inter-proton distances obtained from ten observed NOE contacts. A restrained molecular dynamics (RMD) approach was used to get the optimized solution structure of berberine. The structure of berberine and berberrubine molecules was also obtained using the ROESY data available in literature. Comparison of the calculated NMR chemical shifts with the experimental values revealed that DFT methods produce very good results for both proton and carbon chemical shifts. The importance of the basis sets to the calculated NMR parameters is discussed. It has been found that calculated structure and chemical shifts in the gas phase predicted with B3LYP/6-311G** are in very good agreement with the present experimental data and the measured values reported earlier.

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Section: Introductionmentioning

confidence: 99%

Quantum chemical and nuclear magnetic resonance spectral studies on molecular properties and electronic structure of berberine and berberrubine

Tripathi

Chauhan

Thankachan

et al. 2007

Magnetic Reson in Chemistry

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“…This species is used as an antitussive and sedative together with Papaver rhoeas L. in the folk medicine of Turkey (Baytop, 1984). Previous investigations on the alkaloids of this species revealed the existence of the benzylisoquinoline (macrostomine, dehydromacrostomine, sevanine), aporphine (isocorydine), protopine (protopine), and rhoeadine (rhoeadine, papaverrubine A, B, D, E), types (Preininger, 1986). Recently, we reported the isolation of isopavine (amurensine, amurensinine) and protoberberine (cheilantifoline) types from Papaver macrostomum collected from Northwestern Turkey (Saryar, 2002).…”

Section: Introductionmentioning

confidence: 96%

Antimicrobial Activity and Phytochemical Studies on Turkish Samples ofPapaver macrostomum.

Ünsal

Sarıyar

Akarsu

et al. 2007

Pharmaceutical Biology

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Three alkaloids, cheilantifoline, mecambrine, and laudanosine, and two flavonoids, luteoline and tricine, have been isolated from two samples of Papaver macrostomum Boiss. & Huet ex Boiss. (Papaveraceae) of Turkish origin. Antimicrobial tests have been performed on the extracts obtained from these species. It has been found that diethyl ether and acetone extracts of two samples obtained from the aerial parts of the plant have antimicrobial activity against almost all bacteria tested. The existence of flavonoids and the antimicrobial activity of this species are reported for the first time.

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“…The genus Papaver L. is represented by more than 120 species, rich in isoquinoline and morphinane alkaloids (Preininger, 1986). In our previous phytochemical studies on Papaver nudicaule L. growing in Mongolia, we reported the isolation and identifi cation of 13 alkaloids of the promorphinane, proaporphine, protopine, and isopavine type, respectively (Philipov et al, 2007;Istatkova et al, 2008).…”

Section: Introductionmentioning

confidence: 98%

“…There are data about the use of this species in Mongolian folk medicine as a sedative, antitussive, and respiratory regulative remedy, as well as against headache caused by nervous disorders, against painful menstruation, and acute and chronic infl ammation of the stomach (Ligaa, 1996). Chemical studies on this species have been reported, and several alkaloids of the retroprotoberberine, isopavine, protopine, rhoeadine, and papaverrubine type, respectively, have been isolated (Novák and Slavík, 1974;Preininger, 1986). To our knowledge no phytochemical investigations of P. pseudocanescens growing in Mongolia have been carried out till now.…”

Section: Introductionmentioning

confidence: 99%

Chemical and Antiviral Study on Alkaloids from Papaver pseudocanescens M. Pop.

Istatkova

Nikolaeva-Glomb

Galabov

et al. 2012

Zeitschrift Für Naturforschung C

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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-dihydrofl avinantine, and fl avinantine 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 fi rst time in the species. All structures were established by physical and spectral analysis. As a fi rst 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 signifi cant 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.

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Chapter 1 Chemotaxonomy of Papaveraceae and Fumariaceae

Cited by 24 publications

References 131 publications

Quantum chemical and nuclear magnetic resonance spectral studies on molecular properties and electronic structure of berberine and berberrubine

Quantum chemical and nuclear magnetic resonance spectral studies on molecular properties and electronic structure of berberine and berberrubine

Antimicrobial Activity and Phytochemical Studies on Turkish Samples ofPapaver macrostomum.

Chemical and Antiviral Study on Alkaloids from Papaver pseudocanescens M. Pop.

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