4829-46-3Relevant academic research and scientific papers
THE ALKALOIDAL CONSTITUENTS OF PAPAVER BRACTEATUM ARYA II
Meshulam, Haim,Lavie, David
, p. 2633 - 2636 (1980)
Seven alkaloids were isolated from Papaver bracteatum Arya II, six of which; thebaine, 14β-hydroxycodeine, codeine, neopine, alpinigenine and protopine, have been previously found to be present in other types of this species.It is the first report of the isolation of O-methylflavinantine from P. bracteatum. - Key Word Index: Papaver bracteatum; Papaveraceae; alkaloids; O-methylflavinantine; thebaine; 14β-hydroxycodeine; codeine; neopine; alpinigenine; protopine.
Biotransformations of morphine alkaloids by fungi: N-demethylations, oxidations, and reductions
Chaudhary, Vigi,Leisch, Hannes,Moudra, Alena,Allen, Blake,De Luca, Vincenzo,Cox, D. Phillip,Hudlicky, Tomas
experimental part, p. 1179 - 1193 (2010/04/26)
Morphine alkaloids and some of its derivatives (morphine, codeine, thebaine, oripavine, hydrocodone, and oxycodone) were subjected to fermentations with six fungal strains. The alkaloids were transformed to a variety of products via biological oxidations, reductions, and oxidative demethylations. The strain Cunninghamella echinulata proved to be the most effective for demethylations of all of the above compounds, except for morphine. The time profile of the conversion of 3-[14CH3]thebaine to 3-[ 14CH3]northebaine by C. echinulata cultures was also determined.
Direct reductive amination and selective 1,2-reduction of α,β-unsaturated aldehydes and ketones by NaBH4 using H3PW12O40 as catalyst
Heydari, Akbar,Khaksar, Samad,Akbari, Jafar,Esfandyari, Maryam,Pourayoubi, Mehrdad,Tajbakhsh, Mahmoud
, p. 1135 - 1138 (2007/10/03)
A simple and convenient procedure for direct reductive amination of aldehydes and ketones with sodium borohydride is described. The reaction has been carried out in methanol in the presence of a catalytic amount of H3PW12O40 (0.5 mol %). α,β-Unsaturated aldehydes and ketones can be easily converted into the corresponding allyl alcohols by reaction with H3PW12O40 (0.5 mol %)/NaBH4.
Transformations of morphine, codeine and their analogues by Bacillus sp
Madyastha,Reddy,Sridhar
, p. 749 - 753 (2007/10/03)
A bacterial strain belonging to the genus Bacillus islolated by enrichment culture technique using morphine as a sole source of carbon transforms morphine and codeine into 14-hydroxymorphinone and 14-hydroxycodeinone as major and 14-hydroxymorphine and 14-hydroxycodeine as minor metabolites, respectively. When the N-methyl group in morphine and codeine are replaced by higher alkyl groups, the organism still retains its ability to carry out 14-hydroxylation as well as oxidation of the C6-hydroxyl group in these N-variants, although the level of metabolites formed are considerably low. The organism readily transforms dihydromorphine and dihydrocodeine into only dihydromorphinone and dihydrocodeinone, respectively, suggesting that the 7,8-double bond is a necessary structural feature to carry out 14-hydroxylation reaction. The cell free extract (20,000 × g supernatant), prepared from morphine grown cells, transforms morphine into 14-hydroxymorphinone in the presence of NAD+, but fails to show activity against testosterone. However, the cell free extract prepared from testosterone grown cells contains significant levels of 17β- hydroxysteroid dehydrogenase but shows no activity against morphine.
