Alkaloids, benzophenanthridine

Work on alkaloid isolation is summarized in Table 11.3 2—396 Arnottianamide (145 R = H, R = Me) and isoarnottianamide (145 R = Me, R = H) have been isolated as minor constituents of Zanthoxylum cuspidatum. These amides can be obtained chemically by Baeyer-Villiger-type oxidation of the immonium group in chelery-thrine and nitidine respectively and a similar biogenesis is suggested. Three Argemone subfusiformis taxa and A, polyanthemos contained mainly the same [Pg.139]

Nagata, K. Okada, H. Itazaki, and S, Uyeo, Chem. and Pharm. Bull. (Japan), 1975, 23, 2878. [Pg.139]

Some lactams, e.g. (146 = COjMe, = /8-H), obtained by enamide photocyc- [Pg.140]

A review of selected potential anticancer principles includes chelidimerine, san-guidimerine, and fagaronine. Extracts of the roots of Fagara xanthoxybides [Pg.141]

Das S (2000) Biophysical studies on the interaction of benzophenanthridine alkaloids with polymorphic nucleic acid structures. PhD Thesis, Jadavpim University... [Pg.208]

DITTRICH, H., KUTCHAN, T.M., Molecular cloning, expression, and induction of berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogenic attack, Proc. Natl. Acad. Sci. USA, 1991,88, 9969-9973. [Pg.177]

KUTCHAN, T.M., DITTRICH, H., Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants, J. Biol. Chem., 1995,270,24475-24481. [Pg.177]

VavreCkova, C., Gawlik, I. and MUller, K. 1996. Benzophenanthridine alkaloids of Chelidonium majus. I. Inhibition of 5- and 12-lipoxygenase by a non-redox mechanism. Planta Medica, 62 397-401. [Pg.241]

Dupont, C., Couillerot, E., Gillet, R., Caron, C., Zeches-Hanrot, M., Riou, J.-F. and Trentesaux, Ch. 2005. The benzophenanthridine alkaloid fagaronine induces erythroleukemic cell differentiation by gene activation. Planta Medica, 71 489 94. [Pg.242]

Lenfeld, J., Kroutil, M., Marsalek, E., Slavik, J Preininger, V. and Simanek, V. 1981. Anti-inflammatory activity of quaternary benzophenanthridine alkaloids from Chelidonium majus. Planta Medica, 43 161-165. [Pg.263]

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. [Pg.278]

Sanguinarine 1 is the prototype of benzophenanthridine alkaloids which occur frequently in plants of the family Papaveraceae. It has anticancer activity and has become of commercial interest because of its antibacterial properties. It is known from biosynthetic studies that protopine 2 is a metabolite on the pathway to sanguinarine, and recent work has shown that a microsomal cytochrome P-450 NADPH dependent enzyme will hydroxylate protopine... [Pg.77]

During synthetic studies on the benzophenanthridine alkaloids, the nitrile ester 1 was treated with sodium hydride in THF in the expectation that a Thorpe-Dieckmann type of reaction would... [Pg.107]

The benzo[ a Jphenanthridine ring system resembles the structure of chrysene, another carcinogen. It is intriguing to note that the carcinogenicity of chrysene is drastically increased by the addition of a methyl group at position 5 of that molecule [86-90]. The position of this methyl group (see structure 9) corresponds to that in the aforementioned benzophenanthridine alkaloids. [Pg.39]

The structural elucidation of a new benzophenanthridine alkaloid, luguine (100) was reported (61) in which the 13C spectrum confirmed both the aromatic nature of ring B and the presence of a hydroxyl group at C-11. The spectrum showed four aliphatic carbon resonances and these were assigned by off-resonance decoupling. [Pg.251]

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. [Pg.66]

Elicitation in conjunction with an in situ extraction phase altered alkaloid production patterns. In particular, elicitors isolated from yeast extract can accelerate the production and the levels of benzophenanthridine alkaloids in E. [Pg.66]

SCHUMACHER, H.-M., GUNDLACH, H FIEDLER, F ZENK, M.H., Elicitation of benzophenanthridine alkaloid synthesis in Eschscholtzia califomica cell cultures. Plant Cell Rep., 1987,6,410-413. [Pg.176]

MAHADY, G.B., BEECHER, C.W., Elicitor-stimulated benzophenanthridine alkaloid biosynthesis in bloodroot suspension cultures is mediated by calcium. Phytochemistry, 1994,37,415-419. [Pg.176]

PARK, S.-U., YU, M., FACCHINI, P.J., Antisense RNA-mediated suppression of benzophenanthridine alkaloid biosynthesis in transgenic cell cultures of California poppy. Plant Physiol., 2002,128, 696-706. [Pg.179]

TANAHASHI, T., ZENK, M.H., Elicitor induction and characterization of microsomal protopine-6-hydroxylase, the central enzyme in benzophenanthridine alkaloid biosynthesis. Phytochemistry, 1990,29,1113-1122. [Pg.180]

Caffeine and related purine alkaloids (AA) papaverine (AA) chelerythrine, sanguinarine, and related benzophenanthridine alkaloids (AA) colchicines (AA) infractine and related indole alkaloids (AA)... [Pg.8]

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