Assessment of N-Acylethanolamines levels in dry achenes from four cultivars of cannabis sativa L.

R.  Ouhtit; S.  Banni; E. Murru; Z. Lamrani; A. Ouhtit; A. Merzouki

doi:10.3989/gya.1200232.2049

Authors

R. Ouhtit Laboratory of Biology, Environment and Sustainable Development (LERBEDD), ENS of Martil - Applied Botany Laboratory, Department of Biology, Faculty of Sciences of Tetouan, Abdelmalek Es-saâdi University https://orcid.org/0009-0001-4509-2880
S. Banni University of Cagliari, Department of Biomedical Sciences, Physiology Section Cittadella Universitaria https://orcid.org/0000-0003-4805-1387
E. Murru University of Cagliari, Department of Biomedical Sciences, Physiology Section Cittadella Universitaria https://orcid.org/0000-0002-7394-5780
Z. Lamrani Laboratory of Biology, Environment and Sustainable Development (LERBEDD), ENS of Martil https://orcid.org/0000-0002-4864-1988
A. Ouhtit ICNODERM Laboratory, Sardegna Ricerche https://orcid.org/0009-0006-6238-4769
A. Merzouki Applied Botany Laboratory, Department of Biology, Faculty of Sciences of Tetouan, Abdelmalek Es-saâdi University - CANN-MED & BALDIYA CROPS Sarl https://orcid.org/0000-0001-8918-9679

DOI:

https://doi.org/10.3989/gya.1200232.2049

Keywords:

Cannabis Sativa.L, cannabis achenes, N-acylethanolamines (NAEs), NAE-Saturated (NAE-SFA), NAE-Monounsaturated (NAE-MUFA), NAE-Polyunsaturated (NAE-PUFA)

Abstract

We utilized high-performance liquid chromatography-mass spectrometry (HPLC-MS/MS), on dry achenes from four cultivars of Cannabis Sativa L.; CA, Cannabis Sativa L. Cultivar Amnesia; CB, Cannabis Sativa L. Cultivar Beldia; CM, Cannabis Sativa L. Cultivar Mexicana; CK, Cannabis Sativa L. Cultivar Khardala, to detect and quantify N-acylethanolamines (NAEs), which are bioactive compounds involved in lipid and energy metabolism. These plants were grown in Chefchaouen, northern Morocco. All four varieties displayed identical NAE lipid profiles, dominated by those derived from 16C and 18C fatty acids. In general, the NAE species presented the following concentration order: [LEA] > [OEA > POEA] > [SEA] > [PEA]. NAE-MUFA was the most abundant type, followed by NAE-PUFA and NAE-SFA, comprising 44, 37, and 19% of all NAEs, respectively, across the varieties. This research provides first-time quantification of NAEs in Cannabis achenes, thus enriching our understanding of these plants’ pharmaceutical and nutritional potential.

Downloads

Download data is not yet available.

References

Arias Gaguancela O, Chapman K. 2022. The biosynthesis and roles of N-acylethanolamines in plants, in: Adv. Bot. Res. pp. 345–373.

Baldini M, Ferfuia C, Piani B, Sepulcri A, Dorigo G, Zuliani F, Danuso F, Cattivello C. 2018. The performance and potentiality of monoecious hemp (Cannabis sativa L.) cultivars as a multipurpose crop. Agronomy 8 (9), 162.

Benabid A. 1982. Bref aperçu sur la zonation altitudinale de la végétation climacique du Maroc. Ecol. Medit. 8 (1), 301–315.

Bandres-Meriz J, Kunz C, Havelund JF, Færgeman NJ, Majali-Martinez A, Ensenauer R, Desoye G. 2023. Distinct maternal metabolites are associated with obesity and glucose-insulin axis in the first trimester of pregnancy. Int. J. Obesity 47, 529–537.

Blancaflor EB, Kilaru A, Keereetaweep J, Khan BR, Faure L, Chapman KD. 2014. N-Acylethanolamines: lipid metabolites with functions in plant growth and development. Plant J. 79 (4), 568–583.

Blancaflor EB, Chapman KD. 2006. Similarities Between Endocannabinoid Signaling in Animal Systems and N-Acylethanolamine Metabolism in Plants, in: Baluška F, Mancuso S, Volkmann D. (Eds.), Communication in Plants: Neuronal Aspects of Plant Life. Springer Berlin Heidelberg, Berlin, Heidelberg, pp. 205–219.

Bomstein RA. 1965. A new class of phosphatides isolated from soft wheat flour. Biochem. Biophys. Res. Commun. 21 (1), 49–54.

Brown JD, Karimian Azari E, Ayala JE. 2017. Oleoylethanolamide: A fat ally in the fight against obesity. Physiol. Behav. 176, 50–58.

Chapman KD, Venables B, Markovic R, Blair RW, Bettinger C. 1999. N -Acylethanolamines in Seeds. Quantification of Molecular Species and Their Degradation upon Imbibition. Plant Physiol. 120, 1157–1164.

Chapman KD. 2004. Occurrence, metabolism, and prospective functions of N acylethanolamines in plants. Prog. Lipid Res. 43 (4), 302–327.

Costa B, Comelli F, Bettoni I, Colleoni M, Giagnoni G. 2008. The endogenous fatty acid amide, palmitoylethanolamide, has anti-allodynic and anti-hyperalgesic effects in a murine model of neuropathic pain: involvement of CB1, TRPV1 and PPARγ receptors and neurotrophic factors. Pain. 139 (3), 541–550.

De la Roche IA, Andrews CJ, Kates M. 1973. Changes in phospholipid composition of a winter wheat cultivar during germination at 2 ºC and 24 ºC. Plant Physiol. 51 (3), 468–473.

Dipatrizio NV. 2021. Endocannabinoids and the gut-brain control of food intake and obesity. Nutrients 13 (4), 1214.

Im DS. 2021. GPR119 and GPR55 as receptors for fatty acid ethanolamides, oleoylethanolamide and palmitoylethanolamide. Int. J. Mol. Sci. 22 (3), 1034.

Felder CC, Nielsen A, Briley EM, Palkovits M, Priller J, Axelrod J, Nguyen DN, Richardson JM, Riggin RM, Koppel GA, Paul SM, Becker GW. 1996. Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Letters. 393, 231–235.

Folch JML, Lees M, Stanley GHA. 1957. A Simple Method for the Isolation and Purification of Total Lipides from Animal Tissues. J. Biol. Chem. 226, 497–509.

Hansen HS, Moesgaard B, Hansen HH, Petersen G. 2000. N-Acylethanolamines and precursor phospholipids—relation to cell injury. Chem. Phys. Lipids 108 (1-2), 135–150.

Hesselink Keppel JM. 2017. Palmitoylethanolamid and Other Lipid Autacoids Against Neuroinflammation, Pain, and Spasms in Multiple Sclerosis. In: Nutrition and Lifestyle in Neurological Autoimmune Diseases. Watson RR, Killgore WDS. Eds.Academic Press: Boston, MA, USA, p. 29–37.

Innis SM, Sprecher H, Hachey D, Edmond J, Anderson RE. 1999. Neonatal polyunsaturated fatty acid metabolism. Lipids 34, 139–149. .

Kasatkina LA, Heinemann A, Hudz YA, Thomas D, Sturm EM. 2020. Stearoylethanolamide interferes with retrograde endocannabinoid signalling and supports the blood-brain barrier integrity under acute systemic inflammation. Biochem. Pharmacol. 174, 113783.

Keereetaweep J, Blancaflor EB, Hornung E, Feussner I, Chapman KD. 2015. Lipoxygenase-derived 9-hydro(pero)xides of linoleoylethanolamide interact with ABA signaling to arrest root development during Arabidopsis seedling establishment. Plant J. 82, 315–327.

Loverme J, La Rana G, Russo R, Calignano A, Piomelli D. 2005. The search for the palmitoylethanolamide receptor. Life Sci. 77 (14), 1685–1698.

Matthäus B, Brühl L. 2008. Virgin hemp seed oil: An interesting niche product. Eur. J. Lip. Sci. Technol. 110 (7), 655–661.

Murru E, Banni S, Carta G. 2013. Nutritional properties of dietary omega-3-enriched phospholipids. BioMed Res. Int. 2013, 965417.

Murru E, Lopes PA, Carta G, Manca C, Abolghasemi A, Guil-Guerrero JL, Prates JAM, Banni S. 2021. Different Dietary N-3 Polyunsaturated Fatty Acid Formulations Distinctively Modify Tissue Fatty Acid and N-Acylethanolamine Profiles. Nutrients 13, 625.

Ouhtit R, Ouhtit A, Redouan FZ, Lamrani Z, Merzouki A. 2024. Morphometry, Oil Yield and Fatty Acid Profile of Cannabis Achenes from the Chefchaouen Region, Mor. J. Chem. 12 (1), 43–60.

Sihag J, Jones PJH. 2018. Oleoylethanolamide: The role of a bioactive lipid amide in modulating eating behaviour. Obes Rev. 19 (2), 178–197.

Venables BJ, Waggoner CA, Chapman KD. 2005. N-acylethanolamines in seeds of selected legumes. Phytochem. 66 (16), 1913–1918.

Wang YS, Shrestha R, Kilaru A, Wiant W, Venables BJ, Chapman KD, Blancaflor EB. 2006. Manipulation of Arabidopsis fatty acid amide hydrolase expression modifies plant growth and sensitivity to N-acylethanolamines. Proc. Natl. Acad. Sci. USA. 103 (32), 12197–12202.

Weidenfeld J, Feldman S, Mechoulam R. 1994. Effect of the brain constituent anandamide, a cannabinoid receptor agonist, on the hypothalamo-pituitary-adrenal axis in the rat. Neuroendocrinol. 59 (2), 110–112.