Aporphine alkaloids, from

Langlois, A., Mulholland, D. A., Crouch, N. R. and Grace, O. M. 2004. Aporphine alkaloid from Papaver aculeatum (sect. Horrida Papaveraceae) of southern Africa. Biochem. Syst. Ecol. 32 1087-1090... 

Goren, A. C., Zhou, B.-N. and Kingston, D. G. I. 2003. Cytotoxic and DNA damaging activity of some aporphine alkaloids from Stephania dinklagei. Planta Medica, 69 867-868. 

Barton and Cohen (48) were the first to suggest the seminal idea that dienones could be intermediates in the biosynthesis of aporphine alkaloids from benzylisoquinolines, since such dienones could rearrange to the aporphine nucleus either through a dienone-phenol or a dienol-benzene rearrangement as shown in the scheme on the following page. 

An aporphine alkaloid from Ocotea variabilis (Lauraceae), C32H32N2O2, Mr 476.62, cryst., mp. 116-117°C, as hydrochloride mp. 230-232°C (decomp.). 

Stevigny C, Block S, De Pauw-GiUet MC, Hoffmann E, de Llabres G, Adjakidje V, et aL Cytotoxic aporphine alkaloids from Cassytha filiformis. Planta Med 2002 68 1042. ... 

You M, Wickramaratne DB, Silva GL, Chai H, Chagwedera TE, Farnsworth NR, Cordell GA, Kinghom AD, Pezzuto JM (1995) (-)-Roemerine, an aporphine alkaloid from Annona senegalensis that reverses the mrrltidrug-resistance phenotype with cultured cells. J Nat Prod 58(4) 598-604... 

Borup I, Kingston DGI1981 Isolation and structure elucidation of cytotoxic aporphine alkaloids from Annona acuminata. (Abstract). Proc Joint Mt Am Soc Pharmacog and Soc for Economic Botany, Boston, July 13-18. American Society of Pharmacognosy, Dept of Pharmaceutical Sciences, University of Pittsburgh, Pittsburgh PA p. 31... 

Borup-Grochtmann I, Kingston DGI 1982 Aporphine alkaloids from Annona acuminata. J Nat Prod 45 102... 

The pseudobenzylisoquinoline alkaloids are fairly widespread in nature, being found among members of Berberidaceae, Annonaceae, Fumariaceae, and Ranunculaceae. The biogenesis of the pseudobenzylisoquinoline alkaloids assumes their formation from protoberberinium salts by C-8—C-8a bond scission in a Baeyer-Villiger-type oxidative rearrangement to produce the enamides of type 73 and 74. These amides may be further biotransformed either to rugosinone (76) type alkaloids by hydrolytic N-deformylation followed by oxidation or to ledecorine (75) by enzymatic reduction. These transformations were corroborated by in vitro studies (80-82). It is suggested that enamide seco alkaloids may be precursors of aporphine alkaloids (80), on one hand, and of cularine alkaloids (77), on the other. 

The potential properties of A. suaveolens Bl. has a source of topoisomerase II inhibitor is open for exploration. The plant probably elaborates aporphine alkaloids because aporphines are known to occur in the genus Artabotrys (2,3), Liriodenine and athero-spermidine from Artabotrys undnatus and artabotrine from Artabotrys zeylanicus abrogated the survival of cancer cells cultured in vitro (4). 

Later, squamolone was isolated from Hexalobus crispiflorus A.Rich, along with aporphine alkaloids, and the methoxyurea 31 (70) H. crispiflorus was collected in Nigeria. The genus Hexalobus consists of five species growing in southern and tropical Africa and Madagascar. The possibility of 31 being an extraction artifact of an unknown precursor has been considered. 

Misik, V., L. Bezakova, L. Malekova, and D. Kostalova. 1995. Lipoxygenase inhibition and antioxidant properties of protoberberine and aporphine alkaloids isolated from Mahonia aquifolium. Planta Med. 61 372-373. 

Woldemariam, T. Z., J. M. Betz, and P. J. Houghton. 1997. Analysis of aporphine and quinolizidine alkaloids from Caulophyllum thalictroides by densitometry and HPLC. J. Pharm. Biomed. Anal. 15 839-843. 

The novel aporphine alkaloids romucosine F (1140) from Annona purpurea... 

V-Formylnornantenine (54), a new amidic aporphine alkaloid, has been isolated from Cyclea atjehensis. Analysis of the NMR spectrum at... 

Since previous work on the aporphine alkaloids had shown that the absolute configuration may be determined from the sign of their high-amplitude Cotton effect centered at 235-245 nm and that the positive Cotton effect corresponds to (S) configuration of a twisted diphenyl system, the coincidence of the CD curves of (— )-anhydrolycorine methiodide and (+ )-anhydrolycorine methiodide at 240 nm with those... 

Aporphine and Berberine Alkaloids.—The aporphine alkaloid magnoflorine (42) has been shown to be formed specifically from reticuline (33) in Aquilegia species40... 

Alkaloids of Aconitum karakolicum Rapes.—Workers at Tashkent have completed the elucidation of the structure of aconitine (C34H47N012 m.pt 195—197 °C),28 isolated from the tubers and aerial parts of plants collected in the Terskei Ala-Tau mountain range. Aconitine (55), napelline (70), songorine (71), and the aporphine alkaloid isoboldine were also isolated from the tubers. Aconitine was assigned structure (72) from chemical and H and 13C n.m.r. and mass-spectral analyses. Alkaline hydrolysis of (72) afforded benzoic acid and the amino-alcohol aconifidine... 

In a pair of back-to-back papers, the author and co-workers first reported the isolation and characterization of thalibealine (70), a novel tetrahydro-protoberberine-aporphine dimeric alkaloid from Thalictrum wangii,143 That report was followed by a paper reporting the synthesis of thalprezwalskinone (71) and a revision of the structure of that alkaloid.144... 

The phenanthrene alkaloids are derivatives of l-(2-aminoethyl)phenanthrene (1). Although they do not contain a nitrogen heterocycle, they are considered alkaloids because of their close relationship with aporphine alkaloids (2). In fact, they occur in the same plant families as aporphines, from which they are biogenetically derived, and they are usually included within the aporphi-noids. Phenanthrene alkaloids with a 2-(methylamino)ethyI side chain are... 

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