Cactus Alkaloids XV: β-Phenethylamine Derivatives from Coryphantha macromeris var. runyonii

Keller, William J.; McLaughlin, Jerry L.; Brady, L.R.

doi:10.1002/jps.2600620311

Cited by 29 publications

(4 citation statements)

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“…These reactions, catalyzed by the aromatic amino acid decarboxylase, are commonly the first step in the biosynthesis of many important alkaloids in higher plants (4). Among these amines, β-phenethylamine (β-PEA), C6H5CH2CH2NH2, the decarboxylated product of phenylalanine, has been reported as the major component of alkaloids in cactus (74,93) and certain perennial legume trees such as Alhagi pseudalhagi (48) and many species of Desmodium (45-47), Prosopis nigra (97), and Acacia (15,28). Leaf, stem or root extracts of these plants generally contain various β-PEA derivatives, which show sympatho-mimetic properties, psychic effects, and other versatile pharmacological actions in higher animals (48,73,145).…”

Section: Biogenic Amines In Legume Root Nodulesmentioning

confidence: 99%

Biogenic Amines in Rhizobia and Legume Root Nodules

Fujihara

2009

Microb. Environ.

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Root-nodule bacteria (rhizobia) are of great importance for nitrogen acquisition through symbiotic nitrogen fixation in a wide variety of leguminous plants. These bacteria differ from most other soil microorganisms by taking dual forms, i.e. a free-living form in soils and a symbiotic form inside of host legumes. Therefore, they should have a versatile strategy for survival, whether inhabiting soils or root nodules formed through rhizobia-legume interactions. Rhizobia generally contain large amounts of the biogenic amine homospermidine, an analog of spermidine which is an essential cellular component in most living systems. The external pH, salinity and a rapid change in osmolarity are thought to be significant environmental factors affecting the persistence of rhizobia. The present review describes the regulation of homospermidine biosynthesis in response to environmental stress and its possible functional role in rhizobia. Legume root nodules, an alternative habitat of rhizobia, usually contain a variety of biogenic amines besides homospermidine and the occurrence of some of these amines is closely associated with rhizobial infections. In the second half of this review, novel biogenic amines found in certain legume root nodules and the mechanism of their synthesis involving cooperation between the rhizobia and host legume cells are also described.

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Section: Biogenic Amines In Legume Root Nodulesmentioning

confidence: 99%

Biogenic Amines in Rhizobia and Legume Root Nodules

Fujihara

2009

Microb. Environ.

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“…These reactions, catalyzed by the aromatic amino acid decarboxylase (E.C.4.1.1.28), are commonly the first step in the biosynthesis of many important alkaloids (Berlin and Fecker, 2000;Facchini and DeLuca, 1995;Gu¨gler et al, 1988;Marques and Brodelius, 1988). b-Phenethylamine (b-PHA), the decarboxylated form of phenylalanine, has formerly been reported as the usual component of alkaloids in cactus (Keller et al, 1973;Mata and McLaughlin, 1980) and in perennial legume trees such as Alhagi pseudalhagi , Prosopis nigra (Moro et al, 1975), and many species of Desmodium (Ghosal and Banerjee, 1969;Ghosal et al, 1972;Ghosal and Mehta, 1974) and Acacia (Camp and Norvell, 1966;Fitzgerald, 1964). Tissue extracts of these plant species generally contain a variety of b-PHA derivatives (e.g., mescaline, N-methyl-b-PHA, and hordenine), often referred to as PHA alkaloids, which show sympatho-mimetic properties, psychic effects, and other versatile pharmacological actions on higher animals Kapadia and Fayez, 1970;Smith, 1977a).…”

Section: Introductionmentioning

confidence: 99%

Accumulation of an Aromatic Amine, β-Phenethylamine, in Root Nodules of Adzuki Bean Vigna angularis

2006

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Neuroactive aromatic amines acting on the central nervous system are widespread in the plant kingdom. We have previously found b-phenethylamine (b-PHA), one of the aromatic alkaloids, in root nodules of various annual legume crops. The present study was undertaken to determine the site of b-PHA accumulation within root nodules of the adzuki bean Vigna angularis. High concentrations of b-PHA were always detected in the alkaloid fraction of adzuki bean root nodules. Related aromatic amines such as tyramine, dopamine, and other b-PHA derivatives, which are found in various medicinal plants, were not detected in adzuki bean root nodules. The amounts of b-PHA in root nodules varied not only with the growth stage of the host plant, but also with nodule age; b-PHA levels increased with nodule development, but declined with nodule senescence. Adzuki bean nodules, after crushing with a grinding medium, were separated into bacteroids and a nodule cytosol fraction. A large amount of b-PHA was detected in the bacteroids, while a very small amount was prsent in the nodule cytosol fraction derived from plant cells. The bacteroids in the mature nodules contained considerably higher amounts of b-PHA than did those in immature or senescent nodules. The formation of b-PHA in root-nodule bacteria was then tested using eight strains of Rhizobiaceae (Rhizobium, Bradyrhizobium and Sinorhizobium), including a strain isolated from root nodules of field-grown adzuki bean plant. None of the cultured cells produced b-PHA in liquid media in the presence or absence of phenylalanine, a putative precursor of b-PHA. Nitrogen-fixing bacteroids within nodules are the cells uniquely differentiated from root-nodule bacteria. The present results suggest that b-PHA is formed associated with the differentiation of vegetative bradyrhizobia into nitrogenfixing bacteroids with the plant host cells.

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“…Kikuchi, Uchiyama, Ogata, Kikura-Hanajiri, and Goda [41] evaluated the presence of alkaloids in one herbal product that was sold as incense in Japan, and they identified, using chromatographic and spectrometric approaches, two hallucinogenic phenethylamines (normacromerine and macromerine); additionally, by means of DNA sequence analyses, they found that the psychotropic product may include C. macromeris as one of its constituents. Similarly, in a series of papers, Keller and McLaughlin [47], Keller et al [48], and Keller [49] reported the presence of alkaloids such as macromerine and normacromerine in C. macromeris sp. Runyonii, suggesting thatin past decades-this plant species was promoted as a natural and legal psychedelic agent; nevertheless, we did not find the reported molecules, suggesting that among the varieties there may exist phytochemical differences.…”

Section: Resultsmentioning

confidence: 85%

Alkaloid and Nitrogenated Compounds from Different Sections of Coryphantha macromeris Plants and Callus Cultures

Viera-Escareño,

Perez-Molphe Balch,

Gómez-Aguirre

et al. 2023

Applied Sciences

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One of the distinctive characteristics of cacti species is the presence of alkaloids. Alkaloids are nitrogenated molecules with hallucinogenic and pharmacological properties in humans and other animals. Plant cell, tissue, and organ culture have emerged as an effective tool for investigating the biosynthesis of a variety of functional metabolites and for studying the preservation of endangered plant species. In this study, we examined the alkaloid and nitrogenated compound profiles of the aerial and radicular sections of Coryphantha macromeris plants that were cultivated in both greenhouse and in vitro conditions. Additionally, we analyzed the callus cultures generated from stem discs. To perform these analyses, Ultra-High-Performance Liquid Chromatography coupled with High-Resolution Mass Spectrometry (UHPLC-PDA-HESI-Orbitrap-MS/MS) was utilized. Under the working parameters, 78 compounds were detected, and 61 of them were identified. Among the identified compounds, the in vitro plants presented 24 compounds, greenhouse plants a total of 21 compounds, and callus tissue 16 compounds. On the other hand, 7 compounds (laurydiethanolamine, toluic acids, and their derivatives) were detected in all systems, suggesting that these metabolites may serve as markers to help find the authenticity of C. macromeris preparations, and that, plant and cell-tissue cultures with this plant species are suitable for the biosynthesis of the selected compounds. In addition, our research suggests that no alkaloids with reported psychotropic properties are present in C. macromeris.

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Cactus Alkaloids XV: β-Phenethylamine Derivatives from Coryphantha macromeris var. runyonii

Cited by 29 publications

References 11 publications

Biogenic Amines in Rhizobia and Legume Root Nodules

Biogenic Amines in Rhizobia and Legume Root Nodules

Accumulation of an Aromatic Amine, β-Phenethylamine, in Root Nodules of Adzuki Bean Vigna angularis

Alkaloid and Nitrogenated Compounds from Different Sections of Coryphantha macromeris Plants and Callus Cultures

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