Distinct mechanisms underlying local antinociceptive and pronociceptive effects of natural alkylamides from Acmella oleracea compared to synthetic isobutylalkyl amide

Dallazen, Jorge Luiz; Maria-Ferreira, Daniele; Luz, Bruna Barbosa da; Nascimento, Adamara Machado; Cipriani, Thales R.; Souza, Lauro Mera de; Glugoski, Letícia Polli; Silva, Bruno José Gonçalves; Geppetti, Pierangelo; Werner, Maria Fernanda de Paula

doi:10.1016/j.fitote.2018.11.001

Cited by 19 publications

(8 citation statements)

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“…Also, the NO-K + channel pathway was thought to be involved in its mechanism of action since pretreatment with 1 H -[1,2,4]oxadiazolo[1,2- a ]quinoxalin-1-one (1 mg/kg, s. c. ) and glibenclamide (10 mg/kg, s. c. ) reduced the antinociceptive effects of affinin (Déciga-Campos et al 2010 ). Other studies showing the mechanisms associated with the antinociceptive and pro-nociceptive effects of alkylamides as evaluated in chemical and sensorial tests revealed that they promoted analgesia in neurogenic and inflammatory phases of formalin test against glutamate-induced nociception (Dallazen et al 2018 ).…”

Section: Antinociceptive Effects Of Alkylamidesmentioning

confidence: 99%

“…The pericarps from the fruits of Z. bungeanum are used in traditional medicine for the treatment of vomiting, toothache, stomachache, abdominal pain, and diarrhea (Wang et al 2017 ). Acmella oleracea (L.) R.K. Jansen, Asteraceae, is used in ethnomedicine to relieve toothache (Dallazen et al 2018 ). A. pyrethrum is used as an aphrodisiac in Indian ayurvedic medicine for the treatment of male sexual dysfunction, including infertility (Sharma et al 2013 ).…”

Section: Ethnomedicinal Uses Of Alkylamide-containing Plantsmentioning

confidence: 99%

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Chemistry and Pharmacology of Alkylamides from Natural Origin

Elufioye

Habtemariam

Adejare

2020

Rev. Bras. Farmacogn.

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Interest in alkylamide, as a class of compound, has grown tremendously in recent years. This interest is due to the many presumed benefits in food, cosmetics, and medicine. This review focuses on the different alkylamides naturally occurring in many plant species. Several methods have been employed for their identification as well as isolation and several in vitro and in vivo studies have revealed their therapeutic effects in various diseases. In general, alkylamides have been reported to have several biological activities and pharmacological effects which include immunomodulatory, antithrombotic, antimicrobial, antiviral, antioxidant, anti-inflammatory, analgesic, anticancer, antidiabetic, and antiprotozoal activities. Moreover, many studies have reported on their mechanisms of action, structure-activity relationship, pharmacokinetics, and toxicity. We herein present an updated report on the chemistry and pharmacology of alkylamides of natural origin.

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Section: Antinociceptive Effects Of Alkylamidesmentioning

confidence: 99%

Section: Ethnomedicinal Uses Of Alkylamide-containing Plantsmentioning

confidence: 99%

Chemistry and Pharmacology of Alkylamides from Natural Origin

Elufioye

Habtemariam

Adejare

2020

Rev. Bras. Farmacogn.

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“…This points to dual actions of alkamides as both TRPV1 agonists and antagonists, which can both lead to channel inactivation and pain relief. Interestingly, low dose synthetic isobutylalkylamide administration was shown the be anti-nociceptive, whereas high doses induced nociceptive behaviors in mice, with the authors suggesting the anti-nociceptive effects arising from blocking of ion channels [63]. Further, lingual application of synthetic isobutylalkylamide activated mechanosensitive neurons through modulation of potassium channels in human testing and caused a tingling sensation, while repeated exposure to the isobutylalkylamide causes desensitization of the channels and lessened tingling [64] supporting the concept of inhibition of neuron activities through desensitization of ion channels.…”

Section: Neuronsmentioning

confidence: 99%

The Structure and Function of Alkamides in Mammalian Systems

Johnstone¹,

Laster²

2022

Natural Drugs From Plants

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Alkamides, or alkylamides, are fatty acid amides produced by plants from the genera Echinacea, Acmella, Spilanthes, and Heliopsis among others. Alkamides contain varying head groups, an amide moiety, and a fatty acid tail with varying numbers of carbons and double and triple bonds. Extracts from these plants have been used worldwide by native peoples for the treatment of numerous medical disorders, including bacterial and viral infections, inflammation, liver and kidney disorders, and pain. In vitro, these molecules display a variety of different activities depending on the cell type tested. Studies with neurons, macrophages and mast cells have revealed interactions between alkamides and a number of different cells surface receptors and intracellular signaling molecules. Generally, the alkamides have been found to exert suppressive effects, inhibiting cellular activation. In this report we introduce the structure of alkamides and review their effects in a number of different cellular systems. We also describe structure:function studies that have been performed with alkamides. While these studies have not as yet revealed general rules for alkamide activity, interesting insights have been revealed. The stage is set for the development of synthetic, designer alkamides with targeted in vivo activities.

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“…Among the alkylamides, spilanthol ((E, E, Z)-2,6,8-decatrienoic acid N-isobutylamide) is considered to be the most potent bioactive compound found in A. oleracea. First identified by Gerber in 1903 as identical to affinin 1, spilanthol has been mostly found in Acmella flowers, leaves, and stems [4,7,8,[12][13][14][15][16], but also in roots [17,18], and its accumulation in in vitro cell cultures has been documented [2,3]. Due to its pharmacological importance, based on a series of effects typical of alkylamides, such as analgesic, neuroprotective, antioxidant, antimutagenic, anti-cancer, anti-inflammatory, antimicrobial, anti-larvicidal, and insecticidal activities [19], many protocols for spilanthol production and extraction have been developed (see [19] for a review; [20]).…”

Section: Introductionmentioning

confidence: 99%

An Efficient Method for the Genetic Transformation of Acmella oleracea L. (Spilanthes acmella Linn.) with Agrobacterium tumefaciens

Maggini

Bettini

Firenzuoli

et al. 2021

Plants

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Acmella oleracea L. is an important medicinal plant, commonly known as the toothache plant. It is a rich source of secondary metabolites used for the treatment of different human disorders. The demand for Acmella oleracea L. has increased due to its putative health benefits (in terms of both biomass quantity and bioactive compound purification). In vitro plant cultures have allowed the rapid increase of raw material availability through the use of suitable regeneration and multiplication systems. On the other hand, there is a general lack of methods for Acmella genetic transformation as a promising new technological approach for the improvement of secondary metabolites. In this work, an efficient transformation protocol has been established using the Agrobacterium tumefaciens LBA4404 strain bearing the binary vector pBI121 containing the NPTII gene for the resistance to kanamycin. Plant genetic transformation has been verified by direct polymerase chain reaction and GUS assay on regenerants. Transformation efficiency has been affected by the high level of the selection agent kanamycin. To our knowledge, this is the first report on the genetic transformation of A. oleracea, paving the way to further studies to improve in vitro plant growth and secondary metabolite production.

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Distinct mechanisms underlying local antinociceptive and pronociceptive effects of natural alkylamides from Acmella oleracea compared to synthetic isobutylalkyl amide

Cited by 19 publications

References 50 publications

Chemistry and Pharmacology of Alkylamides from Natural Origin

Chemistry and Pharmacology of Alkylamides from Natural Origin

The Structure and Function of Alkamides in Mammalian Systems

An Efficient Method for the Genetic Transformation of Acmella oleracea L. (Spilanthes acmella Linn.) with Agrobacterium tumefaciens

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