Prospects for cannabinoids as anti‐inflammatory agents

Zurier, Robert B.

doi:10.1002/jcb.10291

Cited by 59 publications

(55 citation statements)

References 25 publications

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“…1; ajulemic acid, AJA). The synthesis, chemistry, and biological activity of AJA have been the subjects of several reviews (3,4,24,25). The observation (26) that oral administration of low dose (0.1 mg/kg/day) AJA suppresses joint inflammation and tissue injury in rats with adjuvant arthritis led to further investigation of its mechanisms of action.…”

Section: Ajulemic Acid (Aja Ct3 Ip751)mentioning

confidence: 99%

“…Other reviews cover certain aspects of this subject and the reader is referred to them for a discussion of earlier reports (1)(2)(3)(4). In this review are reports published in the last 5 years on the activities of all classes of cannabinoids, including the endogenous cannabinoids such as anandamide, related compounds such as the elmiric acids (EMAs), and noncannabinoid components of Cannabis that show antiinflammatory action.…”

Section: Introductionmentioning

confidence: 99%

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Cannabinoids, Endocannabinoids, and Related Analogs in Inflammation

Burstein

Zurier

2009

AAPS J

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123

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Abstract. This review covers reports published in the last 5 years on the anti-inflammatory activities of all classes of cannabinoids, including phytocannabinoids such as tetrahydrocannabinol and cannabidiol, synthetic analogs such as ajulemic acid and nabilone, the endogenous cannabinoids anandamide and related compounds, namely, the elmiric acids, and finally, noncannabinoid components of Cannabis that show anti-inflammatory action. It is intended to be an update on the topic of the involvement of cannabinoids in the process of inflammation. A possible mechanism for these actions is suggested involving increased production of eicosanoids that promote the resolution of inflammation. This differentiates these cannabinoids from cyclooxygenase-2 inhibitors that suppress the synthesis of eicosanoids that promote the induction of the inflammatory process.

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Section: Ajulemic Acid (Aja Ct3 Ip751)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cannabinoids, Endocannabinoids, and Related Analogs in Inflammation

Burstein

Zurier

2009

AAPS J

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123

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“…The mechanisms responsible for the anti-inflammatory and joint protective properties of the synthetic cannabinoid AJA are have been studied (Zurier, 2003). Although the elmiric acids are structurally different than AJA, there are certain similarities in their actions so that a comparison of AJA with the elmiric acids may be helpful in understanding both.…”

Section: Ajulemic Acid (Aja)mentioning

confidence: 99%

The elmiric acids: Biologically active anandamide analogs

Burstein

2008

Neuropharmacology

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SummaryAs chemical entities, lipoamino acids have been known for some time. However, more recently their occurrence and importance in mammalian species has been discovered. They appear to have close relationships with the endocannabinoids not only structurally but also in terms of biological actions. The latter include analgesia, anti-inflammatory effects, inhibition of cell proliferation and calcium ion mobilization. To date about 40 naturally occurring members of this family have been identified and, additionally, several synthetic analogs have been prepared and studied. To facilitate their identity, a nomenclature system has been suggested based on the name elmiric acid (EMA). The prototypic example, N-arachidonoyl glycine does not bind to CB1, however it does inhibit the glycine transporter GLYT2a and also appears to be a ligand for the orphan G-protein-coupled receptor GPR18. It may also have a role in regulating tissue levels of anandamide by virtue of its inhibitory effect on FAAH the enzyme that mediates inactivation of anandamide. Its concentration in rat brain is several fold higher than anandamide supporting its possible role as a physiological mediator. Future studies should be aimed at elucidating the actions of all of the members of this interesting family of molecules. Keywordsendocannabinoid; lipoamino acid; eicosanoid; elmiric acid; inflammation; anandamide Lipoamino acids (fatty acid-amino acid conjugates): general considerationsThe older literature on this topic is mainly concerned with lipoamino acids of bacterial origin (Batrakov et al., 2000;Kawai et al., 1990;Kawazoe et al., 1991;Lerouge et al., 1988;Miyazaki et al., 1993). These involve amino acid conjugation with complex and unusual fatty acids and little is known about their function in bacteria.More recently, attention has been given to lipoamino acids present in mammalian species in part because of their possible relationships to the endocannabinoids. The closely related analog of anandamide, N-arachidonylglycine (NAGly), is in a sense, a comparable acid analog to anandamide as the THC metabolite, THC-11-oic acid is to THC. NAGly is an endogenous substance found in rat brain and other sites that occurs in amounts greater than the closely related endocannabinoid, anandamide (Huang et al., 2001). However, the origin of NAGly in vivo is not completely understood. Sumner.Burstein@umassmed.edu, Tel: 508-856-2850, Fax: 508-856-2003. Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Prior reports (Burstein et al. 1997;Huang et al., 2001), suggest that NAGly might have analgesic properties similar to tho...

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“…The major active constituent of the plant Cannabis sativa (marijuana), ∆ 9 -tetrahydrocannabinol, and a variety of natural and synthetic cannabinoids have been shown to possess antinociceptive and anti-inflammatory activities (6)(7)(8). For millennia, Cannabis preparations have been used in folk medicine for the treatment of a wide variety of disorders, including those affecting the gastrointestinal tract (9).…”

Section: Introductionmentioning

confidence: 99%

The endogenous cannabinoid system protects against colonic inflammation

Massa¹,

Marsicano²,

Hermann³

et al. 2004

J. Clin. Invest.

362

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Excessive inflammatory responses can emerge as a potential danger for organisms' health. Physiological balance between pro- and anti-inflammatory processes constitutes an important feature of responses against harmful events. Here, we show that cannabinoid receptors type 1 (CB1) mediate intrinsic protective signals that counteract proinflammatory responses. Both intrarectal infusion of 2,4-dinitrobenzene sulfonic acid (DNBS) and oral administration of dextrane sulfate sodium induced stronger inflammation in CB1-deficient mice (CB1 -/- ) than in wild-type littermates (CB1 +/+ ). Treatment of wild-type mice with the specific CB1 antagonist N-(piperidino-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3- carboxamide (SR141716A) mimicked the phenotype of CB1 -/- mice, showing an acute requirement of CB1 receptors for protection from inflammation. Consistently, treatment with the cannabinoid receptor ago- nist R(-)-7-hydroxy-delta6 -tetra-hydrocannabinol-dimethylheptyl (HU210) or genetic ablation of the endo- cannabinoid-degrading enzyme fatty acid amide hydrolase (FAAH) resulted in protection against DNBS-induced colitis. Electrophysiological recordings from circular smooth muscle cells, performed 8 hours after DNBS treatment, revealed spontaneous oscillatory action potentials in CB1 -/- but not in CB1 +/+ colons, indi- cating an early CB1-mediated control of inflammation-induced irritation of smooth muscle cells. DNBS treatment increased the percentage of myenteric neurons expressing CB1 receptors, suggesting an enhancement of cannabinoid signaling during colitis. Our results indicate that the endogenous cannabinoid system represents a promising therapeutic target for the treatment of intestinal disease conditions characterized by excessive inflammatory responses

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Prospects for cannabinoids as anti‐inflammatory agents

Cited by 59 publications

References 25 publications

Cannabinoids, Endocannabinoids, and Related Analogs in Inflammation

Cannabinoids, Endocannabinoids, and Related Analogs in Inflammation

The elmiric acids: Biologically active anandamide analogs

The endogenous cannabinoid system protects against colonic inflammation

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