Nicotine alkaloids biosynthesis

Oksman-Caldentey, K.M. (2007) Tropane and nicotine alkaloid biosynthesis-novel approaches towards biotechnological production of plant-derived pharmaceuticals. Curr. Pharm. 

Hibi et al. " have reported on putrescine A-methyltransferase isolated from the nicotine biosynthetic pathway coded by cDNA. Recent advances in cell and molecular biology of alkaloid biosynthesis have heightened awareness of the genetic importance. 

NT437 Leete, E., and S. A. Slattery. Incorporation of (2- C) nicotinic acid into the tobacco alkaloids. Biosynthesis of anatabine and alpha, beta-dipyridyl. J Am Chem Soc 1976 98 6326. 

The Rutaceae oxazoles are evidently derived from /V-nicotinoyl-p-(p-hydroxy)-phenylethylamide (51), with the exception of balsoxin (25) and texamine (26) in which the nicotinoyl moiety is replaced by benzoyl. The condensation of these tyramine and nicotinic acid residues does not represent any major departure from the standard routes of alkaloid biosynthesis in the Rutaceae, for it has long been recognized that the alkaloids of this family are all derived from either phenylalanine (52), tyrosine, (53), or anthranilic acid (54) (22), the latter being the acknowledged precursor to nicotinic acid in most organisms (23). The formation of the putative oxazole precursor 51 or its equivalent therefore constitutes a convergence of the two predominant modes of alkaloid biosynthesis in the family. 

The production of toxins is only one aspect of plant defense strategy. As a result of the persistent battle of plants and herbivores, many optimized phenotypes have evolved, such as the preferential accumulation of alkaloids in tissues with a pattern that is consistent with predictions of optimal defense theory,65 i.e., the defense metabolites are allocated preferentially to tissues with a high probability of attack.66 The inducibility of pathways leading to plant secondary compounds as a strategy to minimize the costs of plant defense is a result of permanent optimization. One of a few examples of inducible alkaloid biosynthesis is the different Nicotiana species that exhibit dramatic wound-induced increases of nicotine, nomicotine, or anabasine.67... 

Keywords alkaloid biosynthesis alkaloid genes nicotine tropane alkaloids pyrrolizidine alkaloids benzylisoquinoline alkaloids monoterpene indole alkaloids ergot alkaloids acridone alkaloids purine alkaloids taxol betalains... 

Figure 3 (a) Representative tropane and nicotine alkaloids, (b) Tropane biosynthesis. ODC, ornithine decarboxylase PMT, putrescine N-methyltransferase MPO, diamine oxidase TRl, tropinone reductase 1 H6H, hyocyamine 6b-hydroxylase. 

Figure 1.6. Routes from L-tyrosine to alkaloids. Alkaloid biosynthesis is often grouped into categories based on the initiating amino acid i.e. the ornithine/cysteine route (e.g. nicotine) the phenylalanine/tyrosine/tryptophan route (e.g. the isoquinoline alkaloids,...

Amino acids act as precursor foe biosynthesis of alkaloids. Ornithine and lysine are common amino acids used as starting material for alkaloid biosynthesis. Cocaine and nicotine are classical examples form this series. 

There are some difficulties associated with a highly attractive model for piperidine alkaloid biosynthesis (this Report, p. 9). There is still debate about the symmetrical or unsymmetrical incorporation of into nicotine (this... 

The A-methyl-A -pyrrolinium cation is the last common intermediate in both tropane alkaloid and nicotine biosynthesis (Scheme 3). A-Methyl-A -pyrrolinium cation formation begins with the decarboxylation of ornithine and arginine by ornithine decarboxylase (ODC) and arginine decarboxylase (ADQ, respectively. Putresdne is formed directly from ornithine by ODC, whereas agmatine and A-carbamoylputresdne serve as intermediates when putrescine is formed via ADC. An ODC cDNA isolated from Datura stramonium showed similarity to ADCs and other ODCs 127). ADC cDNAs have been isolated from oat and tomato 128,129). Arginine appears to supply most of the putrescine for alkaloid biosynthesis (l30). 

Hamill JD, Robins RJ, Rhodes MJC (1989) Alkaloid production by transformed root cultures of Cinchona ledgeriana. Planta Med 55 354-357 Hamill JD, Robins RJ, Parr AJ, Evans DM, Furze JM, Rhodes MJC (1990) Overexpressing a yeast ornithine decarboxylase gene in transgenic roots of Nicotiana rustica can lead tq enhanced nicotine accumulation. Plant Mol Biol 15 27-38 Hamill JD, Rounsley S, Spencer A, Todd G, Rhodes MJC (1991) The use of the polymerase chain reaction in plant transformation studies. Plant Cell Rep 10 221-224 Hartmann T, Toppel G (1987) Senecionine N-oxide, the primary product of pyrrolizidine alkaloid biosynthesis in root cultures of Senecio vulgaris. Phytochemistry 26 1639-1643... 

Tropane alkaloid Biosynthesis Scopolamine, nicotine, hygrine, calystegines Bl, calystegines B2, spermidine, spermine, cocaine, tropinone, littorine, tropine... 

Zador E, Jones D (1986) The biosynthesis of a novel nicotine alkaloid in the trichomes of Nicotiana stocktonii. Plant Physiol 82 479-484... 

In a preliminary experiment, it was shown that [7- C] nicotinic acid was significantly incorporated into both ricinine and N-demethylricinine during the first day of germination, which indicated that alkaloid biosynthesis is one of the earliest metabolic processes initiated with growth and differentiation in R. communis. 

Floss et al. (1974) have recently published a review entitled Regulatory Control Mechanisms in Alkaloid Biosynthesis. While the article is not all-inclusive on the subject of alkaloid biology and metabolism, we will use some of its arguments and examples, since it represents the first extensive treatment of the subject of regulation. The pyridine alkaloids, e.g., nicotine, anabasine, and ricinine, have a special relationship to primary metabolic reactions that occur in Nicotiana spp. and Ricinus communis, The control mechanism appears to involve the regulation of the pyri-... 

Another aspect is also frequently applied, which is the alkaloid origin. Nicotine, for example, is included among the tobacco alkaloids and quinolizidine alkaloids occurring in different types of lupine are lupine alkaloids. For practical reasons, classification based on these principles has also been used in the following sections. Today, classification according to the precursors of alkaloid biosynthesis is often promoted. This, however, requires a detailed knowledge of the biogenesis mechanisms (Table 10.2). 

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