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Identification of Endocannabinoid System-Modulating N-Alkylamides from Heliopsis helianthoides var. scabra and Lepidium meyenii

Overview of attention for article published in Journal of Natural Products, June 2014
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About this Attention Score

  • In the top 25% of all research outputs scored by Altmetric
  • High Attention Score compared to outputs of the same age (93rd percentile)
  • High Attention Score compared to outputs of the same age and source (97th percentile)

Mentioned by

blogs
1 blog
twitter
17 tweeters
facebook
1 Facebook page
reddit
1 Redditor

Citations

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31 Dimensions

Readers on

mendeley
70 Mendeley
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Title
Identification of Endocannabinoid System-Modulating N-Alkylamides from Heliopsis helianthoides var. scabra and Lepidium meyenii
Published in
Journal of Natural Products, June 2014
DOI 10.1021/np500292g
Pubmed ID
Authors

Zsanett Hajdu, Simon Nicolussi, Mark Rau, László Lorántfy, Peter Forgo, Judit Hohmann, Dezső Csupor, Jürg Gertsch

Abstract

The discovery of the interaction of plant-derived N-alkylamides (NAAs) and the mammalian endocannabinoid system (ECS) and the existence of a plant endogenous N-acylethanolamine signaling system have led to the re-evaluation of this group of compounds. Herein, the isolation of seven NAAs and the assessment of their effects on major protein targets in the ECS network are reported. Four NAAs, octadeca-2E,4E,8E,10Z,14Z-pentaene-12-ynoic acid isobutylamide (1), octadeca-2E,4E,8E,10Z,14Z-pentaene-12-ynoic acid 2'-methylbutylamide (2), hexadeca-2E,4E,9Z-triene-12,14-diynoic acid isobutylamide (3), and hexadeca-2E,4E,9,12-tetraenoic acid 2'-methylbutylamide (4), were identified from Heliopsis helianthoides var. scabra. Compounds 2-4 are new natural products, while 1 was isolated for the first time from this species. The previously described macamides, N-(3-methoxybenzyl)-(9Z,12Z,15Z)-octadecatrienamide (5), N-benzyl-(9Z,12Z,15Z)-octadecatrienamide (6), and N-benzyl-(9Z,12Z)-octadecadienamide (7), were isolated from Lepidium meyenii (Maca). N-Methylbutylamide 4 and N-benzylamide 7 showed submicromolar and selective binding affinities for the cannabinoid CB1 receptor (Ki values of 0.31 and 0.48 μM, respectively). Notably, compound 7 also exhibited weak fatty acid amide hydrolase (FAAH) inhibition (IC50 = 4 μM) and a potent inhibition of anandamide cellular uptake (IC50 = 0.67 μM) that was stronger than the inhibition obtained with the controls OMDM-2 and UCM707. The pronounced ECS polypharmacology of compound 7 highlights the potential involvement of the arachidonoyl-mimicking 9Z,12Z double-bond system in the linoleoyl group for the overall cannabimimetic action of NAAs. This study provides additional strong evidence of the endocannabinoid substrate mimicking of plant-derived NAAs and uncovers a direct and indirect cannabimimetic action of the Peruvian Maca root.

Twitter Demographics

The data shown below were collected from the profiles of 17 tweeters who shared this research output. Click here to find out more about how the information was compiled.

Mendeley readers

The data shown below were compiled from readership statistics for 70 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
United States 2 3%
Peru 1 1%
Unknown 67 96%

Demographic breakdown

Readers by professional status Count As %
Researcher 14 20%
Student > Master 12 17%
Student > Ph. D. Student 12 17%
Student > Bachelor 10 14%
Student > Doctoral Student 8 11%
Other 11 16%
Unknown 3 4%
Readers by discipline Count As %
Agricultural and Biological Sciences 26 37%
Pharmacology, Toxicology and Pharmaceutical Science 11 16%
Chemistry 11 16%
Biochemistry, Genetics and Molecular Biology 6 9%
Medicine and Dentistry 5 7%
Other 7 10%
Unknown 4 6%

Attention Score in Context

This research output has an Altmetric Attention Score of 22. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 13 June 2020.
All research outputs
#997,927
of 16,253,497 outputs
Outputs from Journal of Natural Products
#71
of 4,027 outputs
Outputs of similar age
#14,759
of 212,371 outputs
Outputs of similar age from Journal of Natural Products
#1
of 34 outputs
Altmetric has tracked 16,253,497 research outputs across all sources so far. Compared to these this one has done particularly well and is in the 93rd percentile: it's in the top 10% of all research outputs ever tracked by Altmetric.
So far Altmetric has tracked 4,027 research outputs from this source. They receive a mean Attention Score of 4.7. This one has done particularly well, scoring higher than 98% of its peers.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 212,371 tracked outputs that were published within six weeks on either side of this one in any source. This one has done particularly well, scoring higher than 93% of its contemporaries.
We're also able to compare this research output to 34 others from the same source and published within six weeks on either side of this one. This one has done particularly well, scoring higher than 97% of its contemporaries.