Meconopsis

Tanaka, M. et al., A malonylated anthocyanin and flavonols in blue Meconopsis flowers, Phytochemistry, 56, 373, 2001. 

The aforementioned eight bases have already been reviewed in relevant sections of Vols. 12 and 17 of this treatise. However, only a brief reference has been made in Vol. 17 to amurensinine iV-metho salt (31). Originally isolated as an unidentified quaternary base from Meconopsis napaulensis (79), it was later reisolated from various species of Meconopsis and shown to be the quaternary analog of (—)-amurensinine (25) by direct comparison with the A -metho salt prepared from authentic (—)-amurensinine (80). It should be mentioned that ( )-amurensinine A7-metho salt had been previously prepared through total synthesis (81). Two new tertiary bases have been isolated since the previous review by Santavy (5) (—)-thalidine (21) and (-)-thalidicine (23). 

It has been suggested that the presence of (—)-amurensinine (25) as the main alkaloid in various Meconopsis species indicates the relationship of this genus with Papaver species of the Section Scapiflora 80). By way of parallel thinking, the genus Roemeria, which is known to produce isopavine bases, can be interrelated with the Papaver species of the Section Scapiflora as well as with Meconopsis species. 

Croton discolor (Euphorbiaceae) rlq 1,140 70 Croton plumieri (Euphorbiaceae) phy 8, 777 69 Meconopsis cambrica (Papaveraceae) jnp 44, 67 81 Papaver triniaefolium (Papaveraceae) pm 63,575 97... 

Meconopsis speciosa (Papaveraceae) zh 27,459 96 Roemeria refracta (Papaveraceae) jnp 46,293 83... 

Slavik (380) was the first to isolate mecambroline (1,2-methylene-dioxy-10-hydroxyaporphine) from Meconopsis cambrica. It has hypotensive effects upon mice and rabbits (393). The question of the structure-activity relationships between the pharmacological actions of this alkaloid and aporheine has been discussed (393). 

Cryptocarya longifolia14 Fumaria judaica111 Fumaria schleicheri112 Meconopsis cambrica113 Stephania glabra114 Thalictrum alpinum13... 

Codeine, 14-hydroxycodeine, neopine, and O-methylflavinantine have been isolated from Papaver bracteatum,146 flavinantine and amurine from Meconopsis cambrica,113 isosinoacutine from Stephania elegans,174 and a new alkaloid, tridictyophylline, for which the structure (96) was determined by X-ray crystallography, from Triclisia dictyophylla.175 Bound morphine, codeine, and thebaine have been found in P. bracteatum and P. somniferum,176 and the effect of the period of maturation of the plants on the yield of these three alkaloids from P. somniferum has been studied.177,178 Codeine has been isolated from cell suspension cultures of P. somniferum under conditions where no morphine, norcodeine, or thebaine could be detected.179... 

Bocconia frutescens110 Corydalis incisa522 Meconopsis cambrica113 Zanthoxylum monophyllum116 Zanthoxylum nitidum146... 

Mecambroline was isolated from Meconopsis carnbrica Vig. (Papaver-aceae), and the elemental data indicated the value C18H17O3N. The alkaloid melts at 145°, and exhibits [aj +76° (in CHCI3). A hydrochloride salt was obtained (inp 264°-266°) as well as a picrate (mp 179°-180°). Color tests showed the presence of a methylenedioxy and a phenolic group. The UV-spectrum had 308 and 275 mp, (log e 4.0 and 4.2), with a shoulder at 269 mp (log e 4.1), typical of a 1,2,10-tri-substituted aporphine. 0-Methylation with diazomethane gave a base (mp 111°-112°) 6). 

G. Tayl. (Meconopsis heterophylla Benth.) protopine, sai uinarine, stylophylline [(—)- -hydrastine] c/x > a... 

Formerly, rhoeadine and papaverrubine alkaloids were known to occur only in the plants of the genus Papaver. Recently, Slavik et al. have shown that rhoeadine and papaverrubine E are present in Bocconia frutescens and papaverrubine D in Meconopsis betonicifolia, M. horridula, M. napaulensis, M. paniculata, M. robusta, M. rudis, and M. sinuata (33, 50). The genus Meconopsis is botanically closely related to the genus Papaver, a relation thus confirmed chemotaxonomically (see structures 152-154 in Table V). 

Slavik isolated, the alkaloid MR-1 from Meconopsis rudis Prain. It is an N-methyltetrahydronorharmane (6-methoxy-2-methyl-l,2,3,4-tetrahydro-j8-carboline) (210) (221). 

Slavik showed that the presence of the rhoeadane alkaloids is not restricted to the plants of the genus Papaver but also to those of Bocconia and Meconopsis (33, 50,221). Dimeric alkaloids were found in the plants of the genus Bocconia, Dicentra, Papaver, and Sanguinaria (see Table I). 

Amurensinine methohydroxide Meconopsis horridula, M. napaulensis, M. rudis... 

Amurensinine methohydroxide (62) Meconopsis betonicifolia, M. horridula, M. nepalensis,... 

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