Phenylalkylamine alkaloids from<b><i>Stapelia hirsuta L.</i></b>

Shabana, M.; Gonaid, Mariam; Salama, Maha M.; Abdel‐Sattar, Essam

doi:10.1080/14786410500137718

Cited by 11 publications

(14 citation statements)

References 14 publications

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“…Although PEA is quite rare in plant kingdom, there are some reports on its presence in algae (Rolle et al 1977;Percot et al 2009) and plants (Smith 1977;Shabana et al 2006). PEA has been mainly studied as a metabolite of neurotransmitters in animals and in the human brain (Blau 1978;Saavedra 1978).…”

Section: Discussionmentioning

confidence: 96%

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The effect of methyl jasmonate on accumulation of 2-phenylethylamine and putrescine in seedlings of common buckwheat (Fagopyrum esculentum)

Horbowicz

Kosson²,

Wiczkowski

et al. 2010

Acta Physiol Plant

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The effects of exogenously applied methyl jasmonate on content of biogenic amines: putrescine, spermidine, tyramine, cadaverine and 2-phenylethylamine in seedlings of common buckwheat (Fagopyrum esculentum Moench) were investigated. The studies have shown that methyl jasmonate stimulates the conversion of L-phenylalanine into 2-phenylethylamine and increases the endogenous levels of putrescine in hypocotyls and cotyledons of buckwheat seedlings. Simultaneous feeding the seedlings with L-phenylalanine and methyl jasmonate has indicated that conversion of L-phenylalanine into 2-phenylethylamine can be one of possible reasons, caused by the methyl jasmonate suppression of anthocyanins synthesis in hypocotyls. To our knowledge, the stimulation of conversion of L-phenylalanine into 2-phenylethylamine by methyl jasmonate, as found in the present study, is described for the first time in higher plants.

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Section: Discussionmentioning

confidence: 96%

“…PEA occurrence has been shown in marine algae (Percot et al 2009), and some terrestrial plants (Shabana et al 2006). The role of PEA in plants remains unclear.…”

Section: Introductionmentioning

confidence: 98%

The effect of methyl jasmonate on accumulation of 2-phenylethylamine and putrescine in seedlings of common buckwheat (Fagopyrum esculentum)

Horbowicz

Kosson²,

Wiczkowski

et al. 2010

Acta Physiol Plant

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“…Our results revealed the QSI potentiality of alkaloids such as hordenine ( ID 283 ), 1248 , and 3492 . Hordenin (CAS# 3595-05-9) is a natural alkaloid of the phenethylamine class exhibiting a widespread occurrence in plants (ornamentals, fruits and vegetables), including those that are used for human and animal consumption [22] – [23] . Following injection, hordenine stimulates the release of norepinephrine in mammals hence acting indirectly as an adrenergic drug [24] – [25] .…”

Section: Discussionmentioning

confidence: 99%

At a Supra-Physiological Concentration, Human Sexual Hormones Act as Quorum-Sensing Inhibitors

et al. 2013

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N-Acylhomoserine lactone (AHL)-mediated quorum-sensing (QS) regulates virulence functions in plant and animal pathogens such as Agrobacterium tumefaciens and Pseudomonas aeruginosa. A chemolibrary of more than 3500 compounds was screened using two bacterial AHL-biosensors to identify QS-inhibitors (QSIs). The purity and structure of 15 QSIs selected through this screening were verified using HPLC MS/MS tools and their activity tested on the A. tumefaciens and P. aeruginosa bacterial models. The IC50 value of the identified QSIs ranged from 2.5 to 90 µg/ml, values that are in the same range as those reported for the previously identified QSI 4-nitropyridine-N-oxide (IC50 24 µg/ml). Under the tested culture conditions, most of the identified QSIs did not exhibit bacteriostatic or bactericidal activities. One third of the tested QSIs, including the plant compound hordenine and the human sexual hormone estrone, decreased the frequency of the QS-regulated horizontal transfer of the tumor-inducing (Ti) plasmid in A. tumefaciens. Hordenine, estrone as well as its structural relatives estriol and estradiol, also decreased AHL accumulation and the expression of six QS-regulated genes (lasI, lasR, lasB, rhlI, rhlR, and rhlA) in cultures of the opportunist pathogen P. aeruginosa. Moreover, the ectopic expression of the AHL-receptors RhlR and LasR of P. aeruginosa in E. coli showed that their gene-regulatory activity was affected by the QSIs. Finally, modeling of the structural interactions between the human hormones and AHL-receptors LasR of P. aeruginosa and TraR of A. tumefaciens confirmed the competitive binding capability of the human sexual hormones. This work indicates potential interferences between bacterial and eukaryotic hormonal communications.

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“…2-Phenylethylamine (PEA) rarely occurs in plants, and its physiological role remains unclear (Smith, 1977;Shabana et al, 2006). It is product of l-phenylalanine (l-PHE) decarboxylation by aromatic l-amino acid decarboxylase (Smith, 1977).…”

Section: Introductionmentioning

confidence: 99%

Methyl jasmonate stimulates biosynthesis of 2-phenylethylamine, phenylacetic acid and 2-phenylethanol in seedlings of common buckwheat

et al. 2015

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Methyl jasmonate has a strong effect on secondary metabolizm in plants, by stimulating the biosynthesis a number of phenolic compounds and alkaloids. Common buckwheat (Fagopyrum esculentum Moench) is an important source of biologically active compounds. This research focuses on the detection and quantification of 2-phenylethylamine and its possible metabolites in the cotyledons, hypocotyl and roots of common buckwheat seedlings treated with methyl jasmonate. In cotyledons of buckwheat sprouts, only traces of 2-phenylethylamine were found, while in the hypocotyl and roots its concentration was about 150 and 1000-times higher, respectively. Treatment with methyl jasmonate resulted in a 4-fold increase of the 2-phenylethylamine level in the cotyledons of 7-day buckwheat seedlings, and an 11-fold and 5-fold increase in hypocotyl and roots, respectively. Methyl jasmonate treatment led also to about 4-fold increase of phenylacetic acid content in all examined seedling organs, but did not affect the 2-phenylethanol level in cotyledons, and slightly enhanced in hypocotyl and roots. It has been suggested that 2-phenylethylamine is a substrate for the biosynthesis of phenylacetic acid and 2-phenylethanol, as well as cinnamoyl 2-phenethylamide. In organs of buckwheat seedling treated with methyl jasmonate, higher amounts of aromatic amino acid transaminase mRNA were found. The enzyme can be involved in the synthesis of phenylpyruvic acid, but the presence of this compound could not be confirmed in any of the examined organs of common buckwheat seedling.

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Phenylalkylamine alkaloids fromStapelia hirsuta L.

Cited by 11 publications

References 14 publications

The effect of methyl jasmonate on accumulation of 2-phenylethylamine and putrescine in seedlings of common buckwheat (Fagopyrum esculentum)

The effect of methyl jasmonate on accumulation of 2-phenylethylamine and putrescine in seedlings of common buckwheat (Fagopyrum esculentum)

At a Supra-Physiological Concentration, Human Sexual Hormones Act as Quorum-Sensing Inhibitors

Methyl jasmonate stimulates biosynthesis of 2-phenylethylamine, phenylacetic acid and 2-phenylethanol in seedlings of common buckwheat

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