Biodiversity in the alkaloids of Turkish Papaver species

Abstract

There are about 35 Papaver species growing in Turkey, which are grouped into eight sections, namely Argemonidium, Carinata, Glauca, Miltantha, Oxytona, Papaver, Pilosa, and Rhoeadium.As a result of our extensive work on the alkaloids of Turkish Papaver species the presence of several chemotypes has been shown. Among these chemotypes, medicinally important alkaloids such as noscapine (=narcotine), papaverine-and thebaine-containing samples have been found as new sources for the production of them.The infraspecific variation encountered within the Papaver species has been demonstrated mainly in two sections of the genus, Miltantha and Oxytona. The alkaloids of seven species (Papaver armeniacum, P. curviscapum, P. cylindricum, P. fugax, P. persicum, P. polychaetum, and P. triniifolium) of the section Miltantha have been studied, and the existence of chemical strains has been shown mainly in P. fugax, P. persicum, and P. triniifolium.Investigations on the species of the section Oxytona indicated that there is a relationship between the major alkaloid content and the chromosome numbers of the samples.Isolation of new secoberbine-type alkaloids as well as promorphinane-and morphinane-types has revealed the biosynthetic relationship between the alkaloids of Miltantha and Oxytona species. Chemical races are also known for species of Papaver within other sections of the genus.P. lateritium of Turkish origin from section Pilosa yielded some secoberbine and protoberberine types, whereas P. rhopalothece of the section Rhoeadium contained narcotine as a major alkaloid. Isolation of spirobenzylisoquinoline type from P. argemone (sect. Argemonidium) was the first report of the occurrence of this type in the Papaveraceae.

CYP82Y1 Is N-Methylcanadine 1-Hydroxylase, a Key Noscapine Biosynthetic Enzyme in Opium Poppy

“…A protoberberine, such as scoulerine, has also been hypothesized to potentially undergo N-methylation and C8 oxidation to the secoberbine macrantaldehyde, which could be reduced to macrantaline or oxidized to macrantoridine (7). Theoretically, macrantaldehyde could undergo oxidation to narcotinehemiacetal (37). As such, a hypothetical scheme for noscapine biosynthesis in opium poppy was proposed whereby N-methylcanadine is hydroxylated at C1 and possibly O-methylated to form 1-methoxy-N-methylcanadine (9).…”

“…The drawback of this hypothesis is the lack of empirical evidence for the occurrence of secoberbine alkaloids in opium poppy. Most known secoberbine alkaloids have been isolated from different Papaver species such as Papaver pseudo-oriental, Papaver armeiacum, and Papaver fugax (Sariyar 2002). However, the proposed pathway extrapolated from the partial physiological characterization of a putative noscapine biosynthetic gene cluster supports the natural occurrence of secoberbine alkaloids in opium poppy (10).…”

Characterization of Three O-Methyltransferases Involved in Noscapine Biosynthesis in Opium Poppy

“…The lactone carbonyl group of noscapine was suggested to derive from the N-methyl group of reticuline (Battersby and Hirst, 1965). Additional support for the enzymatic transformation of (S)-reticuline to noscapine has also been reported (Gözler, 1983;Sariyar, 1986Sariyar, , 2002Sariyar et al, 1990). Initial steps involved in the conversion of the protoberberine alkaloid (S)-scoulerine to a phthalideisoquinoline alkaloid intermediate ultimately leading to the formation of noscapine are proposed in Figure 1.…”

Antimicrobial activity of four annualPapaverspecies growing in Turkey

“…In some regions of Turkey, a decoction prepared from red poppy petals is used for mouth inflammations in children and the infusion of the aerial parts is drunk for lowering the blood sugar level. Previous reports on the alkaloid content of P. rhoeas showed great variation within this species and the presence of aporphine type (roemerine, isocorydine), protopine type (protopine, allocryptopine, coulteropine), protoberberine type (berberine, coptisine, sinactine), rhoeadine type (rhoeadine, rhoeagenine, isorhoeadine, papaverrubine A) alkaloids has been shown (Kalav & Sarıyar, 1989;Sarıyar et al, 2002).…”

“…The alkaloids of most of the species belonging to section Rhoeadium have been investigated and the presence of some medicinally important alkaloids has been shown (Sarıyar & Phillipson, 1981;Sarıyar & Kalav, 1990;Atay et al, 1996;Mat et al, 2000;Kalav & Sarıyar, 1989;Sarıyar et al, 2002).…”