Enzymatic transformations of morphinane alkaloids

Horseradish peroxidase transforms morphinane alkaloids into N-oxides and morphine to pseudomorphine in the presence of hydrogen peroxide. The crude poppy enzyme fraction shows the same activities. The rates of reactions were influenced by phenolic compounds and their relation controlled by the concentration of hydrogen peroxide and the presence of ascorbic acid.     

A rapid quantitative method for the determination of thebaine in Papaver bracteatum

A rapid method enabling a quantitative analysis of thebaine in capsules and latex of Papaver bracteatum has been devised, based on a TLC technique. This method was compared to the commonly used GLC procedure, and highly significant correlation coefficient (r = 0.90) and linear regression were found between the two methods. Values for concentrations to the nearest ±0.25% of the standard spots can be reached by this simple and rapid thebaine determination.     

Production of monoclonal antibodies and ELISA for thebaine and codeine

The ratio of hapten and bovine serum albumin in antigen conjugate was exactly determined by matrix-assisted laser desorption/ionization mass spectrometry. Monoclonal antibodies against thebaine and codeine were produced by hybridoma fused with the sprenocytes immunized with thebaine- and codeine-bovine serum albumin conjugate and HAT-sensitive mouse myeloma cell line, P3-X63-Ag8-653. No cross-reaction of anti-thebaine antibody against morphine was observed. Very small cross-reaction appeared in codeine (0.004%). The cross-reaction of anti-codeine antibody against morphine and thebaine was 2.97 and 5.98%, respectively. The full measuring range of the assay extends from 60 pg mL to 1 ng mL for thebaine and 1 ng mL to 100 ng mL for codeine.     

Biotransformation of thebaine by cell suspension cultures of Papaver somniferum cv. Marianne

Thebaine is biotransformed to neopine by cell suspension cultures of Papaver somniferum cv. Marianne grown in O-B5 medium. Results of precursor stu     

Using AFLP markers for species differentiation and assessment of genetic variability of in vitro-cultured Papaver bracteatum (section Oxytona)

Summary Amplified fragment length polymorphism (AFLP) markers were employed to deteet genetic variation among species of Papever (section Oxytona) and assess genetic fidelity between in vitro cell lines of Papaver bracteatum and mature plants derived from the propagation of their callus cultures. Regenerated plants exhibited morphological and phytochemical characteristics dissimilar to those of their source material. Thebaine, the dominant alkaloid produced by Papaver bracteatum, was not detected in capsules from mature regenerated accessions, indicating that there may have been a loss of genetic uniformity. Instead, the dominant alkaloid produced by the regenerated plant was shown to be isothebaine (by TLC and GC/MS), a metabolic characteristic of P. pseudo-orientale. A Neighbor-Joining tree constructed from AFLP fingerprints distinetly separates the three species of Oxytona while firmly grouping the in vitro-cultured plants with P. pseudo-orientale. Additionally phytochemical data and chromosome counts indicate that the seed used to initiate cultures was of hybrid origin and ihat the loss in genetic uniformity was not due to somaclonal variation occurring during the in vitro culture process. AFLP fingerprinting was therefore able to differentiate Oxytona species and invesgigate allopolyploidy in closely related papaver species.     

吗啡对于蟾蜍离体脊髓的兴奋作用

在蟾蜍离体脊髓标本上,吗啡10~(-5)—10~(-3)M 能增大背根-腹根反射(DR-VRR),此增大作用不被纳洛酮拮抗,但10~(-4)M 的纳洛酮可轻度增大 DR-VRR。含菲核结构的阿片生物碱蒂巴因、可待因的兴奋作用强于吗啡,这三种药物在更高浓度时则抑制、甚至取消 DR-VRR。不含菲核结构的合成镇痛药美沙酮、哌替啶及脑啡肽类似物 FK33-824对 DR-VRR只起抑制作用。虽然吗啡能阻滞脊髓突触前抑制,并以可被纳洛酮逆转的方式取消刺激腹根诱发的背根电位(VR-DDRP),吗啡增大 DR-VRR 并非由于它的去抑制作用。本文结果提示,吗啡的兴奋作用与阿片受体无关,并为含菲核结构的阿片生物碱所特有。     

Morphinan alkaloids in Papaver bracteatum: Biosynthesis and fate

The known metabolic pathway for hydrophenanthrene alkaloids in Papaver somniferum has been examined for occurrence in P. bracteatum, a species reported to contain thebaine but no codeine or morphine. 1,2-Dehydro-reticulinium-[3-¹⁴C] chloride and (±)-reticuline-[3-¹⁴C] were fed to P. bracteatum plants and both were incorporated, the former into reticuline and thebaine and the latter into thebaine, suggesting that thebaine biosynthesis is the same in the two species. Studies of the natural abundance of morphinan alkaloids in P. bracteatum and the results from feeding codeinone-[16-³H] and codeine-[16-³H] indicate that this species can reduce codeinone to codeine but can not perform either of the demethylations to produce codeinone or morphine. Fed thebaine-[16-³H] was substantially metabolized but not by pathways that involved demethylations to either oripavine or northebaine.     

罂粟体内蒂巴因变化规律及水氮耦合对蒂巴因的影响

该文采用HPLC法,分析测定一年生罂粟植株体开花后不同生育期根、茎、叶、果壳中的蒂巴因含量,研究了罂粟体内蒂巴因的变化规律和水氮耦合对蒂巴因的影响。结果表明:一年生罂粟植株体的蒂巴因含量的变化范围在果壳中为1.81%～4.54%,成熟期达到最高;叶片中为0.30%～0.68%,膨大后期最高,采收期最低;根中为0.03%～0.28%,膨大前期最高,采收期最低;茎秆中为0.23%～0.60%,呈递减趋势,采收期最低,茎上、中、下部的蒂巴因含量的变化范围分别为0.42%～0.97%、0.15%～0.60%、0.13%～0.37%。滴灌量和施氮量对一年生罂粟果壳中蒂巴因含量的影响差异显著。罂粟壳质量最佳的水氮偶合条件为I_(130)N_(14),即滴灌量为130 m~3·667 m~(-2),施氮量为14 kg·667 m~(-2)时,蒂巴因含量达最高。