Zuh struktur von mecambridin (oreophilin)

Pfeifer, S; Mann, Ian; Dolejš, L.; Hanuš, V.; Cross, A. D.

doi:10.1016/s0040-4039(00)90951-1

Cited by 13 publications

(6 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 1, 4, 5, and 6 were identifi ed by comparison of their UV, IR, EI-mass, and 1 H NMR spectral data with those of authentic samples originating from other plant material (Philipov et al, 2007;Istatkova et al, 2008). The data of the provided UV, EI-mass, and 1 H NMR spectra for compounds 2, 3, and 8 are in a good agreement with the literature data (Pfeifer et al, 1967;Preininger et al, 1969Preininger et al, , 1970. The structure of alkaloid 7 was determined by comparison of its EI-mass and 1 H NMR spectra with the literature data (Tomita et al, 1966;Shamma, 1972).…”

Section: Phytochemical Studysupporting

confidence: 89%

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

Istatkova

Nikolaeva-Glomb

Galabov

et al. 2012

Zeitschrift Für Naturforschung C

View full text Add to dashboard Cite

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.

show abstract

Section: Phytochemical Studysupporting

confidence: 89%

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

Istatkova

Nikolaeva-Glomb

Galabov

et al. 2012

Zeitschrift Für Naturforschung C

View full text Add to dashboard Cite

show abstract

“…The formation of ions b, c, and d has been discussed by Ohashi et al (3). Ion c is derived by a retro Diels-Alder opening of ring C and ion d by loss of R, or R, from ion c. Loss of a single hydrogen from the neutral nitrogencontaining fragment formed in retro Diels-Alder fragmentation results in ion b. Ions of type n were of negligible intensity in the spectra of the alkaloids examined by Ohashi et al, but have been detected in the mass spectra of other alkaloids in this family (4,5). The formation of ions of type a requires the transfer of a hydrogen from either of rings C or D to ring B.…”

mentioning

confidence: 86%

“…A similar pattern has been reported in the p.m.r. spectrum of tetrahydrojatrorrhizine (5). In alkaloids with 10,ll-substitution the C-8 protons appear to be a broad singlet (T ~5 .…”

Section: ( C )mentioning

confidence: 99%

Mass spectra and proton magnetic resonance spectra of some tetrahydroprotoberberine alkaloids

Chen¹,

MacLean²

1968

Can. J. Chem.

View full text Add to dashboard Cite

The mass spectra and the proton magnetic resonance spectra of tetrahydroprotoberberine alkaloids, oxygenated at the 9-and 10-positions, show marked differences from the spectra of those oxygenated at the 10-and 11-positions. These differences may be useful in structural studies on new members of this group of alkaloids.Canadian Journal o r Chemistry, 46, 2501 (1968) The tetrahydroprotoberberines are a group of alkaloids biogenetically related to benzylisoquinolines and occur in a wide variety of botanical families. The basic skeleton (1) can be identified (1) by its characteristic ultraviolet (u.v.) spectrum ; however, no information regarding the oxygenation pattern of the alkaloids in question can be secured by this method. Recently, in the course of structural studies (2) on two tetrahydroprotoberberine alkaloids, substituted at 1-, 2-, lo-, and 11-positions, namely, caseamine and caseadine, we examined the mass spectra and the proton magnetic resonance @.m.r.) spectra of ten tetrahydroprotoberberine alkaloids. Our results show that there is a systematic way to characterize this group of alkaloids which should be useful to others engaged in structural studies on the tetrahydroprotoberberines. Mass Spectra of Tetrahydroprotoberberine Alkaloids The main fragment ions observed in the mass spectra of tetrahydroprotoberberines are given in The mass spectra of the ten tetrahydroprotoberberine alkaloids which we have examined are found in Figs. 2 and 3 and the pertinent data derived from them are summarized in Table I. With the exclusion of stylopine, the alkaloids may be divided into three groups; (i) those with a hydroxyl group in ring D, dl-scoulerine, capaurimine, and caseamine, (ii) those with 9,lOdimethoxy substitution, dl-canadine, dl-tetrahydropalmatine, capaurine, and, (iii) those with 10,ll-dimethoxy substitution, caseadine, caseadine-0-methyl ether and norcoralydine. Can. J. Chem. Downloaded from www.nrcresearchpress.com by 54.149.104.195 on 05/08/18For personal use only.

show abstract

“…By comparing the UV and high resolution ESI-MS/MS spectra data and retention time with the authentic compounds, eight of them were unequivocally identified, namely tricin (1), hydnocarpin (2), O-methylflavinantine (3), oleracein E (4), mecambridine (5), protopine (6), alborine (7) and berberine (8) 4 , respectively. Seven other peaks (peaks 9-18) could only be tentatively identified as 8,9-dihydroprooxocryptochine (9) [11], magnofloring (10) [38], 6-methoxy-17-methyl-2,3-[methylenebis(oxy)]-morphinan-5-en-7-one (11) [39], reframoline (12) [11], mecambroline (13) [38], amurensine (14) [40], amurensinine (15) [38], meconoquintupline (16) [41], cryptopine (17) [38], and corysamine (18) [38], by comparing the HR-MS and MS/MS data with literature. In general, all nine samples of the six Meconopsi species contain compounds 6, 7, 8, and 18, with high contents of compounds 6 and 18.…”

Section: Identification Of Main Alkaloids In Meconopsis Speciesmentioning

confidence: 99%