Chapter 3 Pyridine and Piperidine Alkaloids

Strunz, George M.; Findlay, John A.

doi:10.1016/s0099-9598(08)60194-7

Cited by 78 publications

(62 citation statements)

References 276 publications

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“…Similarly, nicotinic acid seems to be used effectively for the production of high amounts of anatabine, for which both heterocyclic rings are derived from nicotinic acid (Fig. 2B) (43). In contrast to the other nicotine alkaloids, anatalline had not been detected in BY-2 cells before.…”

Section: ϫ3mentioning

confidence: 95%

A functional genomics approach toward the understanding of secondary metabolism in plant cells

Goossens

Häkkinen

Laakso

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

371

244

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Despite the tremendous importance of secondary metabolites for humans as for the plant itself, plant secondary metabolism remains poorly characterized. Here, we present an experimental approach, based on functional genomics, to facilitate gene discovery in plant secondary metabolism. Targeted metabolite analysis was combined with cDNA-amplified fragment length polymorphism-based transcript profiling of jasmonate-elicited tobacco Bright yellow 2 cells. Transcriptome analysis suggested an extensive jasmonatemediated genetic reprogramming of metabolism, which correlated well with the observed shifts in the biosynthesis of the metabolites investigated. This method, which in addition to transcriptome data also generates gene tags, in the future might lead to the creation of novel tools for metabolic engineering of medicinal plant systems in general. P lants are capable of synthesizing an overwhelming variety of low-molecular-weight organic compounds called secondary metabolites, usually with unique and complex structures. Presently, Ϸ100,000 such compounds have been isolated from higher plants (1). Numerous plant secondary metabolites possess interesting biological activities and find applications, such as pharmaceuticals, insecticides, dyes, flavors, and fragrances. Although secondary metabolism offers attractive targets for plant breeding, the enormous biosynthetic potential of plant cells is still not being exploited. In sharp contrast, metabolism of microorganisms has been successfully engineered for increased production of pharmaceuticals or novel compounds (2, 3). Despite a few decades of research, plant secondary metabolism remains poorly characterized (4). Genetic maps of biosynthetic pathways are still far from complete, whereas knowledge on the regulation of these pathways is practically nonexistent. However, such knowledge is of crucial importance to bypass the low product yield of various secondary metabolites in plants or plant cell cultures.Functional genomics approaches are powerful tools to accelerate comprehensive investigations of cellular metabolism in specialized tissues or whole organisms (5). Yet, related to plant secondary metabolism, only a few reports have been published on such studies, which include the use of comparative quantitative trait loci mapping (6), 2D gel electrophoresis-based proteomics (7), or transcript analysis tools, such as differential display (8, 9), EST databases (10-12), and microarrays (13,14). Nevertheless, still little is known about the genetics that control quantitatively and qualitatively natural variation in secondary metabolism.Because of the lack of extensive genomic data for the vast majority of medicinal plants, it is difficult to use the commonly used microarray-based approach for transcriptome analysis in these plant systems. Such an approach requires prior development of large EST or cDNA clone collections (13,14). As such, the cDNA-amplified fragment length polymorphism (AFLP) technology (15-17) offers an attractive alternative to identify genes involved i...

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Section: ϫ3mentioning

confidence: 95%

A functional genomics approach toward the understanding of secondary metabolism in plant cells

Goossens

Häkkinen

Laakso

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

371

244

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“…Piperidine alkaloids [1] often possess potent biological activity and are therefore of interest for organic and medicinal chemists. [2] Structural types that were addressed in our work are described in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

A Configurational Switch Based on Iridium‐Catalyzed Allylic Cyclization: Application in Asymmetric Total Syntheses of Prosopis, Dendrobate, and Spruce Alkaloids

Gnamm

Brödner

Krauter

et al. 2009

Chemistry A European J

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A method for the stereoselective synthesis of 2,6-disubstituted piperidines has been developed that is based on the use of an intramolecular iridium-catalyzed allylic substitution as a configurational switch. The procedure allows the preparation of 2-vinylpiperidines with enantiomeric excesses (ee) of greater than 99%. As applications, total syntheses of piperidine alkaloids have been elaborated, most often by using Ru-catalyzed cross-metatheses as a key step for introduction of a side chain. Asymmetric total syntheses of the prosopis alkaloids (+)-prosopinine, (+)-prosophylline, (+)-prosopine, and of the dendrobate alkaloid (+)-241D and its C6 epimer are described.

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“…The determination of E was based on equation E ln[(1 ± ee S )/(1 ee S /ee P )]/ln[(1 ee S )/(1 ee S /ee P )] with c ee S /(ee S ee P ) as based on the original equations of Chen et al [26] The equation is valid for irreversible acyl transfers when no side reactions of the substrates or products is observed. 1 H NMR and 13 C NMR spectra were recorded in CDCl 3 on a Jeol Lambda 400 or a Bruker 200 spectrometer with tetramethylsilane as an internal standard. Mass spectra (MS) were taken on Agilent GC-MS instrument equipped with 5973 network mass selective detector and 6890 N network GC-system.…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

“…[1] Piperidine is the nitrogen analogue of a pyranose ring, and as such its derivatives are potential inhibitors of enzymes working on glycosidic bonds. [2,3] The above cases suffice to emphasise the importance of producing piperidine-based structures for synthetic pharmaceuticals and natural products.…”

Section: Introductionmentioning

confidence: 99%

Chemo‐ and Enantioselective Acyl Transfers by Lipases and Acylase I: Preparative Applications in Hydroxymethylpiperidine Chemistry

Lundell¹,

Lehtinen²,

Kanerva³

2003

Adv Synth Catal

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The lipase-and acylase I-catalysed acylation of bifunctional 2-and 3-hydroxymethylpiperidines (1 and 2) and the alcoholysis of the corresponding diacylated counterparts 7 and 8 have been studied. Lipase AK from Pseudomonas fluorescens allowed the preparative-scale resolution of 7 in neat butanol at 50% conversion whereas the 3-regioisomer 8 reacted with negligible enantioselectivity (E 7). The lipase-and acylase I-catalysed acylations of 1 and 2 in organic solvents proceeded with low enantioselectivity. On the other hand, more than 90% of 1 and 2 were transformed to amino esters 3 and 4, respectively, in a highly chemoselective Oacylation with 2,2,2-trifluoroethyl butanoate in the presence of Candida antarctica lipase A in TBME. The O-protected product 3 in the reaction mixture was readily available to another transformation at the piperidine nitrogen although 3 was not separated due to intramolecular O3N acyl migration. The tendency for acyl migration was much less significant in the case of 4.

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Chapter 3 Pyridine and Piperidine Alkaloids

Cited by 78 publications

References 276 publications

A functional genomics approach toward the understanding of secondary metabolism in plant cells

A functional genomics approach toward the understanding of secondary metabolism in plant cells

A Configurational Switch Based on Iridium‐Catalyzed Allylic Cyclization: Application in Asymmetric Total Syntheses of Prosopis, Dendrobate, and Spruce Alkaloids

Chemo‐ and Enantioselective Acyl Transfers by Lipases and Acylase I: Preparative Applications in Hydroxymethylpiperidine Chemistry

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