Eschscholtzia californica

Villegas, M., Leon, R. and Brodelius P. E. 1999. Effects of alginate and immobilization by entrapment in alginate on benzophenanthridine alkaloid production in cell suspension cultures of Eschscholtzia californica. Biotechnology Letters, 21(1) 49-55. 

CALIFORNIA POPPY -- Eschscholtzia californica. Family Papaveraceae (Poppy family). 

Enhanced production of some of the benzophenanthridine alkaloids was found in an in situ extraction system that was composed of silicone fluid and a suspension culture of Eschscholtzia californica [10]. The time course changes of alkaloid production and distribution are shown in Fig. 1. 

Argemone mexicana, Bocconia spp., Chelidonium majus [root], Eschscholtzia californica [cell culture] (Papaveraceae) ffinthoxylum zanthoxyloides (Fagara xanthoxylum) (Rutaceae) ffinthoxylum americanum, z(. spp. (Rutaceae)... 

Schumacher, H.-M. and Zenk, M.H. (1988) Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures. Plant Cell Rep., 7, 43-6. 

Hosel, W., Berlin, J., Hanzlik, T.N. and Conn, E.E. (1985) In vitro biosynthesis of l-(4 -hydroxyphenyl)-2-nitroethane and production of cyanogenic compounds in osmotically stressed cell suspension cultures of Eschscholtzia californica. Planta, 166, 176-81. 

Other herbal materials prepared by roller compaction included St. John s wort (22) and Eschscholtzia californica Cham (23). Tableting of the granulated extract markedly reduced the problems associated with dust and material feed as well as the incidence of capping. Tablets produced from granulated extracts disintegrated three limes faster than those tabletted from the powder blend. Hygroscopicity of . californica Cham, extracts decreased after roller compaction due to decreased material surface area. 

B. Pavine Alkaloids.—Eschscholtzine (70 R = Me) has been isolated from Eschscholtzia californica.89a The structure of ( )-bis-norargemonine (70 R = H) has been confirmed by synthesis.90 The key intermediate (69), prepared by two unexceptional methods, was converted into (70 R = H) in three steps. Interestingly, 1,2-dihydroisoquinoline derivatives do not give this type of product but rather undergo a variety of other reactions if excess acid is avoided [see reactions of compound (58)]. 

Cassy tha filiformis Erythrina ahyssinica Eschscholtzia californica E. douglasii Glaucium flavum... 

Pavines and Isopavines.—(—)-Norargemonine and (—)-bisnorargemonine have been isolated from the roots of Eschscholtzia californica, E. douglassi, and E. glauca (Papaveraceae). ... 

Eschscholamidine (34) Eschscholtzia oregano Escholamine (33) Eschscholtzia oregana Escholinine (22) Eschscholtzia californica... 

Cyclanoline (245) Argemone platyceras, Hunnemannia fumariaefolia Escholidine (246) Eschscholtzia californica, E. douglasii, E. glauca, Hunnemannia fumariaefolia... 

Storage capacity in a cell culture is available inside the cells (e.g., vacuoles) or in the extracellular compartment. The storage facilities of the latter can be remarkedly improved by the addition of liquid organic phases, resins, or other sorbents to the medium. Addition of XAD-7 to Catharanthus roseus cultures resulted in increased yields of indole alkaloids (SS). Addition of a dimethylsiloxane polymer to Eschscholtzia californica cultures improved yields of benzophenanthridine alkaloids ( 9), and increased yields of nicotine and anabasine were obtained by adding of XAD-2 and XAD-4 resins to Nicotiana transformed roots (90,91). 

Sanguinarine, norsanguinarine, dihydrosanguinarine, oxysanguinarine Papaver somniferum P. setigum, P. rhoeas, P. bracteatum, P. orientate, Eschscholtzia californica, Chelidonium japonicum, Macleaya cordata. Dicentra peregrina, Corydalis incisa, C. pallida Callus 418... 

P. nudicaule Papaver somniferum Fumaria capreolata Eschscholtzia californica... 

Chen Z, Lu Y, Wang Z, Tao X, Wei D (2007) Protective effects of satidroside on hypoxia/reoxygenation injury by sodium hydrosulfite in pcl2 cells. Pharm Biol 45(8) 604-612 Cheney RH (1963) Therapeutic potential of Eschscholtziae californicae herba. Pharm Biol 3(3) 413-416... 

Recently, Cho et al. (2008) reported that methyl jasmonate (MJ) and yeast extract (YE) was induced the protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cell cultures. These results were confirmed that the dihydrobenzophenan-thridine oxidase (DHBO) is induced by YE and not by MJ. YE and chitin had similar effects on sanguinarine production and DHBO expression. 

When methyl jasmonate was applied to the surface of tomato plants, the synthesis of a defensive proteinase inhibitor protein was induced, not only in the plant to which the application was made but also in nearby plants. In subsequent studies, this compound was shown to have a similar effect with plants of other families as well (Farmer and Ryan, 1990 Pearce et al., 1991). In a series of experiments, it was demonstrated that methyl jasmonate can be a component of interplant communication systems. Octadecanoid precursors of jasmonic acid were able to activate the synthesis of wound-inducible proteinase inhibitors (Crombie and Mistry, 1991 Farmer and Ryan, 1992). Jasmonic acid is a signal transducer in elicitor-induced plant cultures of Rauvolfia canescens and Eschscholtzia californica. Tissue cultures of 36 species of plants could be induced to accumulate second-... 

Berberine or protoberberine alkaloids [such as stylopine (79)] may be converted into alkaloids of the protopine type (60) (Fig. 32.24) (Geissman and Crout, 1969 Hartmann, 1991). Highly specific microsomal cytochrome P-450-de-pendent enzymes from cells of Eschscholtzia californica (and other species of the Papaveraceae and Fumariaceae) introduce two methylenedioxy bridges into (5)-scoulerine (72) to form (5)-stylopine (79), which is, in turn, an important precursor of the protopine, phthalideisoquinoline, and benzophenanthridine groups (Hartmann, 1991). 

Zenk, 1990). 6-Hydroxyprotopine (82) spontaneously rearranges to dihydrosanguinarine (83) (Tanahashi and Zenk, 1988,1990). Another enzyme (dihydrobenzophenanthridine oxidase) has been isolated from elicited cell suspension cultures of Eschscholtzia californica that catalyzed the oxidation of dihydrobenzophenanthridines to the quaternary alkaloids in the presence of oxygen (Schumacher and Zenk, 1988 Tanahashi and Zenk, 1988, 1990). The pro-R hydrogen at C-13 is retained in chelidonine (80) (Simanek, 1985). 

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