Talk:2-Arachidonoylglycerol

Copyright violation?

The text is a simple copy from http://www.caymanchem.com/app/template/Product.vm/catalog/62160. Someone should change it. —Preceding unsigned comment added by 82.166.182.11 (talk) 16:35, 3 November 2007 (UTC)

IUPAC Name incorrect

The IUPAC name is for a carboxylate group but the article is for the di-carboxylic acid. is there a reason for this?--ChemSpiderMan (talk) 23:58, 5 January 2008 (UTC)

i'm pretty sure the IUPAC name is correct. the article is about a diol, not a di-carboxylate. the IUPAC name is (5Z,8Z,11Z,14Z)-1,3-dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate - the first part is 1,3-dihyroxypropane which is the glycerol-backbone, and the second part is icosa-5,8,11,14-tetraenoate which refers to the arachidonic acid (aka icosatetraenoate). does that make sense? Roadnottaken (talk) 02:08, 6 January 2008 (UTC)

Sorry...I misread the structure..I reworked the structure and suggest the actual IUPAC Name is: 1,3-Dihydroxy-2-propanyl (5Z,8Z,11Z,14Z)-5,8,11,14-icosatetraenoate If you agree I'll let you change it.--ChemSpiderMan (talk) 04:35, 6 January 2008 (UTC)

done. thanks :) Roadnottaken (talk) 05:01, 6 January 2008 (UTC)

milk

Is paternal bovine different than maternal bovine milk? Shjacks45 (talk) 10:23, 15 July 2008 (UTC)

Function

Erm... I understand that this chemical is basically a neurotransmitter, but what does it actually do? Would anyone be willing to tell me or point me to a link that explains it in terms a high school C-grade physiology student could understand? EvangelionUnit01 (talk) 22:13, 30 March 2011 (UTC)

2-AG acts upon the CB1 and CB2 receptors in the brain and body. Once you find out what the purpose of those receptors are, you'll have your answer. - Gunnanmon (talk) 11:33, 11 January 2012 (UTC)

GA Review

This review is transcluded from Talk:2-Arachidonoylglycerol/GA1. The edit link for this section can be used to add comments to the review.

Reviewer: Sasata (talk) 16:28, 8 June 2011 (UTC)

I will review this article; will have comments up here in a day or two. Sasata (talk) 16:28, 8 June 2011 (UTC)

I do not feel that the article meets the GA criteria at this time, and am failing the GAN, as the improvements required will probably take more time to implement than the week or two recommended for GA reviews. Hopefully the list below will help in this article's development. Sasata (talk) 17:12, 10 June 2011 (UTC)

GA review (see here for criteria)

1. It is reasonably well written.

   a (prose): b (MoS):

Many issues with prose, typos. Examples:

• "It is present at relatively high levels in the central nervous system, which started cannabinoid nueromodulatory system in the nervous system." Huh?
• "The chemical was first described in 1994-1995, although had been discovered some time before that." missing word?
• " The activities of Phospholipase C..." enyzme names shouldn't be capitalized.
• "2-Arachidonoylglycerol, next with Anandamide, was the second endocannabinoid discovered. The cannabinoid established the existence of a cannabinoid nueromodulatory system in the nervous system." Ambiguous: which of the two cannabinoids established this existence? (nuero -> neuro)
• "It has been found in maternal bovine and human milk." Is there a type of milk other than maternal?
• Reference 6 (Sugiura et al 1994) is not formatted properly. Is there a title? Ref 12 (Savinainen et al) is missing details. There are other minor issues with inconsistent reference formatting, but these are over and above the lightweight GA criteria.
• Please used title case consistently for journal titles
• Several more wikilinks would be helpful for the average reader who might might be familiar with the science jargon, e.g.: nM, affinity, signaling

1. It is factually accurate and verifiable.

   a (references): b (citations to reliable sources): c(OR):

I'm having problems confirming several of the statements made in the article, e.g.:

• "Shimon Ben-Shabat, School of Pharmacy, discovered the chemical.[5] " This is not what the source says; rather, Ben-Shabat along with several other researchers (Mechoulam, Hanus and colleagues) discovered it. Sasata (talk) 17:12, 10 June 2011 (UTC)
• "it is the most abundant molecular species of monoacylglycerol found in mouse and rat brain (~5-10 nmol/g tissue).[2][3]" The second cited source clearly states it is one of the most abundant (not the most abundant). I couldn't find where the source claims "5-10 nmol/g tissue" (I did see "... the level of total arachidonoylglycerol being 4.75 nmol/g tissue..." Sasata (talk) 17:12, 10 June 2011 (UTC)
• "Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions." Not cited, and not covered by the source cited in the following sentence. I stopped checking here, it seems clear that every statement in the article should be checked against the source.

1. It is broad in its coverage.

   a (major aspects): b (focused):

   There are major deficiencies in this criterion. Pubmed alone lists over 200 review papers with the search term "2-Arachidonoylglycerol", which is totally at odds with the limited number of sources and article length seen here. Here are some major aspects of the topic which are glossed over or not even mentioned at all:

• The role of 2-AG in feeding regulation in the newborn (covered in Fride, E.; Bregman, T.; Kirkham, T. C. (2005). "Endocannabinoids and food intake: Newborn suckling and appetite regulation in adulthood". Experimental biology and medicine (Maywood, N.J.). 230 (4): 225–234. PMID 15792943., a source used in the article)
• Biosynthesis is inadequately covered by two sentences. There have been research papers written about this (and review papers summarizing that research, Ueda, N.; Tsuboi, K.; Uyama, T.; Ohnishi, T. (2011). "Biosynthesis and degradation of the endocannabinoid 2-arachidonoylglycerol". BioFactors. 37 (1): 1–7. doi:10.1002/biof.131. PMID 21328621.). Why no mention of 2-AG catabolism?
• No mention of effects of 2-AG oversigalling Lichtman, A. H.; Blankman, J. L.; Cravatt, B. F. (2010). "Endocannabinoid Overload". Molecular Pharmacology. 78 (6): 993–995. doi:10.1124/mol.110.069427. PMC 2993463. PMID 20952498.
• Role of 2-AG in neurodegenerative and neuroinflammatory disorders Bisogno, T.; Di Marzo, V. (2010). "Cannabinoid receptors and endocannabinoids: Role in neuroinflammatory and neurodegenerative disorders". CNS & neurological disorders drug targets. 9 (5): 564–573. doi:10.2174/187152710793361568. PMID 20632970.
• Pharmacology/physiology should really be expanded, there's a lot more known about this subject than is implied by the length of the section. See reviews like Reggio, P. H. (2010). "Endocannabinoid binding to the cannabinoid receptors: What is known and what remains unknown". Current medicinal chemistry. 17 (14): 1468–1486. doi:10.2174/092986710790980005. PMID 20166921., Yates, M. L.; Barker, E. L. (2009). "Inactivation and Biotransformation of the Endogenous Cannabinoids Anandamide and 2-Arachidonoylglycerol". Molecular Pharmacology. 76 (1): 11–17. doi:10.1124/mol.109.055251. PMID 19389920., Sugiura, T. (2009). "Physiological roles of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand". BioFactors. 35 (1): 88–97. doi:10.1002/biof.18. PMID 19319851., Placzek, E. A.; Okamoto, Y.; Ueda, N.; Barker, E. L. (2008). "Membrane microdomains and metabolic pathways that define anandamide and 2-arachidonyl glycerol biosynthesis and breakdown". Neuropharmacology. 55 (7): 1095–1104. doi:10.1016/j.neuropharm.2008.07.047. PMC 2645998. PMID 18760289., Sugiura, T.; Kishimoto, S.; Oka, S.; Gokoh, M. (2006). "Biochemistry, pharmacology and physiology of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand". Progress in Lipid Research. 45 (5): 405–446. doi:10.1016/j.plipres.2006.03.003. PMID 16678907. (as well as many, many more) for ideas.

1. It follows the neutral point of view policy.

   Fair representation without bias:

2. It is stable.

   No edit wars etc.:

3. It is illustrated by images, where possible and appropriate.

   a (images are tagged and non-free images have fair use rationales): b (appropriate use with suitable captions):

   When the Biosynthesis section gets expanded, a diagram showing the biosynthetic pathway would be helpful.

4. Overall:

   Pass/Fail:

Someone inserted - with a couple of typos - the following reference nº 17 in this page:

Köfalvi, Attila (2008). Cannabinoids and the Brain. New York City: Axel Springer AG. p. 15. ISBN 978-0-387-74348-6. "2-Arachidonoylglycerol can be synthesized from arachidonic acid-containing diacylglycerol derived from increaded inositol phospholid metabolism by the action of a diacylglycerol lipase. 2-Arachidonoylglycerol can also be formed via other pathways such as the hydrolysis of the diaclygly derived from PC and phosphatidic acid by the action of a diacyglycerol lipase and the hydrolysis of arachidonic acid-containing lysophosphatidic acid by the action of a phosphatase. The relative importance of these pathways may depend on the types of cells and stimuli."

This happened without my consent and since it contains an excerpt from the book (which was transcribed with typos), I now make an attempt to delete the reference in question. The author of this text was not me but Dr Takayuki Sugiura from the Teikyo University.

Please do not reinsert text like this from my book, instead, try to look up the original report. Thank you! — Preceding unsigned comment added by Akofalvi (talk • contribs) 20:03, 10 September 2015 (UTC)