Meconic acid as a chemotaxonomic marker in the papaveraceae

Of 48 species of Papaveraceae examined representing 12 genera, 24 were shown to contain meconic acid and of these, 21 were Papaver species. Meconopsis cambrica was also found to contain meconic acid, in contrast to other species of Meconopsis examined. One recent rearrangement of the Papaveraceae includes a grouping of Papaver, Roemeria and Stylomecon together with M. cambrica and our further discovery of meconic acid in two Roemaria species examined leads to the conclusion that meconic acid may be a distinctive taxonomic feature of this new grouping. Some attempt has also been made to correlate meconic acid occurrence with that of certain types of alkaloids, and of chelidonic acid.     

Formation of alkaloids in Corydalis ophiocarpa callus culture

Corydalis ophiocarpa callus tissue was examined for its isoquinoline alkaloid content. The culture has good biosynthetic capabilities for transformation of exogenous alkaloids.     

Three quinicine derived alkaloids from Guettarda trimera

Three alkaloids, isolated from the trunk bark of Guettarda trimera have been identified as derivatives of quinicine on the basis of mass spectrometry, ¹H and ¹³C NMR data.     

Identification of ergoline alkaloids in the genus Argyreia and related genera and their chemotaxonomic implications in the convolvulaceae

The results of the identification of 21 ergoline alkaloids of 14 species of Argyreia; viz.: A. barnesii, A. capitata, A. cuneata, A. luzoninsis, A. mollis, A. maingayi, A. nervosa, A. obtusifolia, A. philippinensis, A. reticulata. A. ridleyi, A. rubicunda, A. splendens and A. sp. and 2 closely related genera; Stictocardia tiliafolia and Rivea corymbosa, by using 2-D TLC procedures are given. A brief discussion of the implications of the ergoline alkaloids and the chemotaxonomy of the Convolvulaceae is also presented.     

Alkaloids of Argemone fruticosa and A. echinata

Argemone fruticosa Thurber ex Gray was analyzed and found to contain hunnemanine as the major alkaloid along with allocryptopine. A. echinata G. B. Ownb. was found to contain cryptopine and berberine as major alkaloids. These analyses indicate that these two species belong among the more specialized species of the genus.     

Morphinane alkaloids in cultured tissues and redifferentiated organs of Papaver somniferum

The capacity of alkaloid synthesis was examined in cultured tissues of Papaver somniferum. Callus, derived meristemoids, redifferentiated roots and     

Adlumidiceine and adlumiceine: New alkaloids of narceine type

The structures of new alkaloids of narceine type, adlumidiceine (II), adlumiceine (III), and enol lactone of adlumidiceine (IV), isolated from Papaver rhoeas L. and Corydalis sempervirens (L.) Pers. (Papaveraceae), were determined by PMR, MS and IR spectra.     

Source of some minor alkaloids in Glaucium flavum

Air oxidation of glaucine leads to 7,6′-dehydroglaucine and 1,2,9,10-tetramethoxyoxoaporphine, and UV irradiation gives dihydropontevedrine, pontevedrine, glaucine-N-oxide and corunine. These results support the view that glaucine, the main alkaloid in Glaucium flavum, may produce all the more oxidized minor alkaloids present in the plant.     

Oxindole alkaloids from Uncaria macrophylla

Four isomeric oxindole alkaloids, isorhynchophylline, rhynchophylline, corynoxine and corynoxine B, have been isolated from the leaves of Uncaria macrophylla Wall. Corynoxine B has not previously been reported as a natural product.     

Alkaloidal content of argentine Argemone

The alkaloid content of different Argentine Argemone has been determined. Two varieties of A. subfusiformis subsp. subfusiformis Ownb. and A. subfusiformis subsp. subinermis Ownb. yielded a similar ratio and content of the following alkaloids: protopine, allocrytopine, berberine, sanguinarine, and chelerythrine. The A. subfusiformis taxa showed a markedly high sanguinarine content in roots as opposed to aerial parts. A. polyanthemos (Fedde) Ownb. showed a different ratio between alkaloids but a qualitative similar result. N-Norchelerythrine was isolated from A. polyanthemos. The chemotaxonomic value of the alkaloid analyses is discussed.     

Rupestrines A-D,alkaloids from the aerial parts of Corydalis rupestris

Phytochemical investigation of the dichloromethane extract of the dried aerial parts of Corydalis rupestris (Papaveraceae) resulted in the identification of four new isoquinoline alkaloids rupestrines A-D and one known isoquinoline alkaloid, namely, stylopine. The structures of these compounds were characterized by extensive spectroscopic methods including 1D- (¹H and ¹³C) and 2D NMR experiments (COSY, HSQC, HMBC, and NOESY) as well as HRESIMS analyses. In addition, the absolute configurations of rupestrines A-D were determined using modified Mosher’s method. Cytotoxic effects of alkaloids and their interaction with albumin were also investigated in this study.     

Bound forms of alkaloids in Papaver somniferum and P. Bracteatum

The polysaccharide fraction of the pericarp and seed of Papaver somniferum were shown to contain bound forms of morphine which were derived from radioactive morphine fed to living plants. Bound forms of codeine, thebaine and some unidentified alkaloid-like compounds were also detected in the pericarp and bound thebaine occurred in the pericarp of Papaver bracteatum. The complexity and molecular weight of the bound alkaloids seemed to increase during ripening, and it is suggested that these substances represent transitional forms in the metabolism and transiocation of morphine from latex to seed.     

N-Oxides of the oxindole alkaloids,isorhynchophylline, rhynchophylline,rhynchociline and ciliaphylline

The N-oxides of isorhynchophylline, rhynchophylline, rhynchociline and ciliaphylline were prepared, for comparison with a new alkaloid from Mitragyna tubulosa.     

Peptide and tetrahydroisoquinoline alkaloids from Euonymus europaeus

Three p-aryloxy macrocyclic peptide alkaloids frangulanine, franganine and frangufoline together with the 1-benzyltetrahydroisoquinoline alkaloid armepavine have been isolated from Euonymus europaeus native to Poland. These types of alkaloids are new to the Celastraceae and are of chemotaxonomic interest.     

Caffeine from green beans of Mascarocoffea

Unequivocal evidence is presented for the presence of 0.55–0.81% caffeine in the beans of population A213 of Coffea kianjavatensis, one taxon of the Mascarocoffea, which traditionally have been viewed as caffeine-free.     

Chemotaxonomic significance of alkaloids in the genus Robynsiophyton

The alkaloids of the monotypic genus Robynsiophyton have been studied for the first time. Most of the quinolizidine alkaloids and esters of quinolizidine alkaloids found in the genus Pearsonia are also the major compounds in Robynsiophyton. These include lupanine, 3β-hydroxylupanine, lebeckianine, lupanine-13-angelate, cajanifoline, cryptanthine, sessilifoline and pearsonine. The results support the idea of a close affinity between Robynsiophyton, Pearsonia and Rothia. Except for the apparent absence of tigliate esters in Pearsonia, differences between the genera seem quantitative only.     

Stress induced formation of purine alkaloids in plant tissue culture of Coffea arabica

Reports that environmental stress may enhance the accumulation of secondary substances in plants led to the idea of introducing stress into tissue cultures with the aim of improving the in vitro production of pharmaceutically active compounds. The test was made with low- and high-producing cell suspension cultures of Coffea arabica. The production of the purine alkaloid caffeine was shown to be stimulated by stressors such as high light intensity and—depending on the culture type—high NACl concentration.