Alkaloids Derived from Histidine: Imidazole (Pilocarpine, Pilosine)

Santos, Ana Paula; Moreno, Paulo Roberto Hrihorowitsch

doi:10.1007/978-3-642-22144-6_27

Cited by 20 publications

(9 citation statements)

References 60 publications

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“…Histidine is involved in many biosynthetic pathways. For example, histidine and histidine derivatives are used during the construction of imidazole-containing alkaloids, 275 while βhydroxyhistidine is an important intermediate in the biosynthesis of nikkomycin. 276 In this section, we will review the biosynthesis of two unusual histidine derivatives, ergothioneine and ovothiol, which have a wide range of physiological roles in bacteria.…”

Section: Histidine-derivedmentioning

confidence: 99%

Biosynthetic Pathways to Nonproteinogenic α-Amino Acids

2019

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Natural nonproteinogenic amino acids vastly outnumber the well-known 22 proteinogenic amino acids. Such amino acids are generated in specialized metabolic pathways. In these pathways, diverse biosynthetic transformations, ranging from isomerizations to the stereospecific functionalization of C–H bonds, are employed to generate structural diversity. The resulting nonproteinogenic amino acids can be integrated into more complex natural products. Here we review recently discovered biosynthetic routes to freestanding nonproteinogenic α-amino acids, with an emphasis on work reported between 2013 and mid-2019.

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Section: Histidine-derivedmentioning

confidence: 99%

Biosynthetic Pathways to Nonproteinogenic α-Amino Acids

2019

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“…Pilocarpus alkaloids are one of the most important classes of histidine-derived alkaloids. Pilosine has similar imidazole and c-lactone structures with other pilocarpus alkaloids, which are characterized by an a-hydroxylbenzyl group instead of the ethyl substituent at C-2 in the lactone ring (Santos et al 2013). Some studies indicated that pilocarpine could be synthesized from 2-oxobutyric acid and urocanic acid, suggesting that pilosine might have the same biosynthetic pathway.…”

Section: Metabolic Profiling Analysis and Comparison Of D Huoshanense And D Officinalementioning

confidence: 99%

Metabolomics analysis of nitrogen-containing metabolites between two Dendrobium plants

Song

Chen

Jin

et al. 2020

Physiol Mol Biol Plants

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Nitrogen-containing compounds especially alkaloids are important medicinal ingredients in caulis dendrobii plants. Using solid-phase extraction coupled with liquid chromatography tandem mass spectrometry and multivariate data analysis methods, metabolic profiling of the nitrogen-containing compounds was established to distinguish Dendrobium huoshanense and Dendrobium officinale. Hundreds of nitrogen-containing compounds from the two caulis dendrobii were purified by the MCX cartridges. Some compounds were identified by high-resolution tandem mass spectrometry technology. Together with multivariate data analysis methods, comparative analysis of the metabolic profiling from two caulis dendrobii was conducted. A total of 133 nitrogen-containing compounds were identified, including amino acids, pyrrolidines, tropanes, pyrimidines, purines, indoles, piperidines, guanidines, quinolines, isoquinolines and terpenoids. Metabolic profiling analysis showed that the composition and contents of these chemical components were significantly different between D. huoshanense and D. officinale.Moreover, some components were species-specific, distributed in the two caulis dendrobii, such as pilosine, ternatusine, etc. Because alkaloids are mainly derived from amino acids via multistep biochemical reactions, the correlation analysis suggested that amino acids were partially associated with several types of components and significantly correlated with certain alkaloids. Arginine was extremely correlated with guanidines. Pyrimidines, purines and niacin-nicotinamide metabolic intermediates were associated with three independent networks. The results further enriched the chemical components currently identified from caulis dendrobii and provided a technical reference for detecting nitrogen-containing compounds in other medicinal plants.

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“…In comparison with the above-mentioned alkaloids, there are fewer reports on their occurrence, and a considerable part of imidazole alkaloids have been identified in marine organisms over the last few decades. 2 The most popular representative of the imidazole alkaloids is undeniably pilocarpine, which was first isolated from Pilocarpus jaborandi Holmes leaves 3 and is known for its therapeutic use as a miotic agent and sialagogue. 4 In general, the occurrence of imidazole alkaloids in plants has been primarily described in the genus Pilocarpus, belonging to the family Rutaceae.…”

Section: Introductionmentioning

confidence: 99%

Detection of Novel Cytotoxic Imidazole Alkaloids in Tomato Products by LC-MS/MS

Hövelmann

Hahn

Hübner

et al. 2019

J. Agric. Food Chem.

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Imidazole alkaloids represent a rather small group of alkaloids and are assumed not to be of significance to the human food chain so far. In this study, novel imidazole alkaloids occurring in tomato products were synthesized and structurally characterized by nuclear-magnetic-resonance spectroscopy and high-resolution mass spectrometry. These alkaloids are amides of either histidinol or histamine and short-chain fatty acids and could be quantitated in all of the 28 analyzed tomato products using a newly developed and validated LC-MS/MS-based method. Levels ranged from approximately 5 μg/kg to almost 3 mg/kg in the analyzed tomato products, and N-caprylhistidinol and its putative isomer were shown to occur in the highest amounts. These imidazole alkaloids are thus regularly ingested in considerable amounts as part of the human diet. In the course of evaluating their effects on the viability of HT-29 cells, all compounds were shown to significantly reduce cell viability starting at concentrations of 100 μM.

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Alkaloids Derived from Histidine: Imidazole (Pilocarpine, Pilosine)

Cited by 20 publications

References 60 publications

Biosynthetic Pathways to Nonproteinogenic α-Amino Acids

Biosynthetic Pathways to Nonproteinogenic α-Amino Acids

Metabolomics analysis of nitrogen-containing metabolites between two Dendrobium plants

Detection of Novel Cytotoxic Imidazole Alkaloids in Tomato Products by LC-MS/MS

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