Peyote Constituents: Chemistry, Biogenesis, and Biological Effects

Kapadia, Govind J.; Fayez, M. B. E.

doi:10.1002/jps.2600591202

Cited by 80 publications

(53 citation statements)

References 220 publications

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“…The oxidative deamination leading to the formation of both the phenylacetic acid metabolite and the 2-(4-bromo-2,5-dimethoxyphenyl)-ethanol seems to be the most important pathway for 2C-B metabolism. This is also the case for the related hallucinogenic compound mescaline [18]. It is well known that monoamine oxidase (MAO) catalyses this metabolic transformation of mescaline in vivo [19,20].…”

Section: Discussionmentioning

confidence: 96%

Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration

Carmo

Boer²,

Remião

et al. 2004

Journal of Chromatography B

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Section: Discussionmentioning

confidence: 96%

Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration

Carmo

Boer²,

Remião

et al. 2004

Journal of Chromatography B

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“…b-PHA-containing plants generally produce various b-PHA derivatives (b-PHA alkaloids), which often cause various actions on the central nervous system of higher animals Kapadia and Fayez, 1970). For instance, N-methyl-b-PHA, which has previously been identified in Acacia berlandieri, is known to act as a toxin causing locomotor ataxia in sheep and goats grazing the browse of this plant (Camp and Norvell, 1966).…”

Section: Discussionmentioning

confidence: 99%

“…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). Some of these plants, therefore, have long been used in various countries and regions as medicinal plants for the purposes of preparing traditional medicines.…”

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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“…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). Most of these plants, therefore, have long been used in various countries and regions as medicinal plants in traditional medicines.…”

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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Peyote Constituents: Chemistry, Biogenesis, and Biological Effects

Cited by 80 publications

References 220 publications

Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration

Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration

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

Biogenic Amines in Rhizobia and Legume Root Nodules

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