N-Alkyl dien- and trienamides from the roots of Otanthus maritimus with binding affinity for opioid and cannabinoid receptors

Ruiu, Stefania; Anzani, Nicola; Orrù, Alessandro; Floris, C.; Caboni, Pierluigi; Maccioni, Elias; Distinto, Simona; Alcaro, Stefano; Cottiglia, Filippo

doi:10.1016/j.bmc.2013.09.017

Cited by 26 publications

(19 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Over 30 compounds have been identified in essential oils, with a primary emphasis on chrysanthenone (40.4-57.2%), filifolone (12.2-15.5%), cis-chrysantenyl acetate (10.1-11.2%) and ␣-pinene (6.7-7.2%) with anti-fungal and anti-inflammatory activity. Chrysanthenone, the main compound of O. maritimus essential oil, is a rare bicyclic monoterpene ketone with a slightly oily-floral aroma suitable for aromatic industry, being found only in members of the Asteraceae family (Cabral et al, 2013;Muselli et al, 2007;Ruiu et al, 2013).…”

Section: Otanthus Maritimus Lmentioning

confidence: 99%

Asteraceae species with most prominent bioactivity and their potential applications: A review

Bessada

Barreira

Oliveira

2015

Industrial Crops and Products

111

View full text Add to dashboard Cite

a b s t r a c tOxidative stress has a relevant part in the etiology of several diseases and metabolic disorders, being reasonable to expect that antioxidant compounds might have beneficial effects in health maintenance or disease prevention. Antioxidant compounds might be isolated and characterized from different plant constituents, such as roots, stems, bark, leaves, flowers, fruits and seeds, using proper extraction methods. The Asteraceae family has a worldwide distribution, with special relevance in the Mediterranean, Eastern Europe and Asia Minor, being acknowledged about 25 000 species integrated in approximately 1000 genera. In addition to the anti-inflammatory, analgesic and antipyretic potential of some of these species, their high antioxidant power, as proven in research works with extracts (of roots, stems, bark, leaves, flowers, fruits and seeds) should be highlighted. Herein, the Asteraceae species with highest potential as sources of natural antioxidants with potential uses in medicine and in pharmaceutical, cosmetic and food industries were identified. The species were selected based on their botanical representativeness, being identified the 9 most relevant species: Achillea millefolium L., Acmella oleraceae Murr., Artemisia absinthium L., Bidens pilosa L., Carthamus tinctorius L., Inula crithmoides L., Matricaria recutita L., Otanthus maritimus L. and Parthenium hysterophorus L.. With the obtained information, it could be concluded that the bioactivity of the selected Asteraceae species lacks a complete characterization, constituting a research scope with great potential to be exploited in the development of dietary supplements, bioactive food ingredients or pharmaceutical based products with application in food industry, dermocosmetics or medicine.

show abstract

Section: Otanthus Maritimus Lmentioning

confidence: 99%

Asteraceae species with most prominent bioactivity and their potential applications: A review

Bessada

Barreira

Oliveira

2015

Industrial Crops and Products

111

View full text Add to dashboard Cite

show abstract

“…Following the progress in chemical isolation and screening techniques, several novel lead molecules were isolated and characterized from the natural products for the development of new drugs. In current years, numerous molecules have been isolated and characterized which showed cannabinoid receptor affinity, efficacy, and therapeutic benefits in the in vitro , in silico , and in vivo studies [ 15 – 21 ]. The agents were also found to inhibit endocannabinoid metabolizing enzymes, FAAH, DAGL, and MAGL inhibitors, and exhibit their potential efficacy mediated by the cannabinoid mediated mechanism [ 7 ].…”

Section: Phytochemicals As Lead Compounds Targeting Ecsmentioning

confidence: 99%

“…Several alkylamides have been isolated from dichloromethane root extract of Otanthus maritimus L. (family: Asteraceae), an aromatic herb growing on sandy beaches along the Mediterranean coasts. These compounds exhibit cannabinoid receptors binding affinity as demonstrated in the in vitro , in silico , and in vivo studies [ 15 , 31 ]. The in silico studies were carried out by generating 3D models of hCB 2 receptors in homology modeling [ 31 ].…”

Section: Phytochemicals As Lead Compounds Targeting Ecsmentioning

confidence: 99%

“…The alkylamides, N-substituted with an isobutyl or dimethylbutyl group and represented by a secondary alkylamide as the amide part, appear to be involved in the CB 2 receptor interaction [ 32 ]. However, it is observed that the tertiary amide 1-[(2 E ,4 E ,8 Z )-tetradecatrienoyl] piperidine which contains a piperidinyl moiety linked to a C14 acyl chain appears to have more affinity and potency on CB 2 than dodeca-2 E ,4 E -dienoic acid isobutylamide, an active principle of Echinacea species [ 15 ]. Overall, alkylamides from Echinacea and Otanthus spp.…”

Section: Phytochemicals As Lead Compounds Targeting Ecsmentioning

confidence: 99%

See 1 more Smart Citation

Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development

Sharma

Sadek

Goyal

et al. 2015

Evidence-Based Complementary and Alternative Medicine

View full text Add to dashboard Cite

The cannabinoid molecules are derived from Cannabis sativa plant which acts on the cannabinoid receptors types 1 and 2 (CB1 and CB2) which have been explored as potential therapeutic targets for drug discovery and development. Currently, there are numerous cannabinoid based synthetic drugs used in clinical practice like the popular ones such as nabilone, dronabinol, and Δ9-tetrahydrocannabinol mediates its action through CB1/CB2 receptors. However, these synthetic based Cannabis derived compounds are known to exert adverse psychiatric effect and have also been exploited for drug abuse. This encourages us to find out an alternative and safe drug with the least psychiatric adverse effects. In recent years, many phytocannabinoids have been isolated from plants other than Cannabis. Several studies have shown that these phytocannabinoids show affinity, potency, selectivity, and efficacy towards cannabinoid receptors and inhibit endocannabinoid metabolizing enzymes, thus reducing hyperactivity of endocannabinoid systems. Also, these naturally derived molecules possess the least adverse effects opposed to the synthetically derived cannabinoids. Therefore, the plant based cannabinoid molecules proved to be promising and emerging therapeutic alternative. The present review provides an overview of therapeutic potential of ligands and plants modulating cannabinoid receptors that may be of interest to pharmaceutical industry in search of new and safer drug discovery and development for future therapeutics.

show abstract

“…68 While the interactions of Echinacea NAAs with CB receptors have been studied in more detail, ECS-interacting NAAs from other plants have been described only recently. 72,73,75,76 The assumption that NAAs may interfere with the ECS due to their structural similarity to endocannabinoids such as anandamide (N-arachidonoylethanolamide, AEA) and palmitoylethanolamide 35 is intuitive, but the confirmation of this assumption is hampered by the lack of structure -activity relationship (SAR) data.…”

Section: Analgesic and Anticonvulsant Effectsmentioning

confidence: 99%

An ethnopharmacological survey conducted in the Bolivian Amazon, and identification of N-alkylamides and lignans from Lepidium meyenii and Heliopsis helianthoides var. scabra with effects on the central nervous system

Zsanett

View full text Add to dashboard Cite

N-Alkyl dien- and trienamides from the roots of Otanthus maritimus with binding affinity for opioid and cannabinoid receptors

Cited by 26 publications

References 37 publications

Asteraceae species with most prominent bioactivity and their potential applications: A review

Asteraceae species with most prominent bioactivity and their potential applications: A review

Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development

An ethnopharmacological survey conducted in the Bolivian Amazon, and identification of N-alkylamides and lignans from Lepidium meyenii and Heliopsis helianthoides var. scabra with effects on the central nervous system

Contact Info

Product

Resources

About