Identification of -Coumaric Acid and Ethyl -Coumarate As the Main Phenolic Components of Hemp ( L.) Roots

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2022 May 14

PMID 35566134

Authors

Chang Min Oh

Joon Yong Choi

In Ah Bae

Hong Taek Kim

Seong Su Hong

Jay Kyun Noah

Yong Chool Boo

Affiliations

Soon will be listed here.

Abstract

Hemp ( L.) contains a variety of secondary metabolites, including cannabinoids, such as psychoactive (-)--Δ⁹-tetrahydrocannabinol. The present study was conducted to identify the major phenolic components contained in hemp root, which has been relatively under-researched compared to other parts of hemp. The aqueous ethanol extract of hemp roots was fractionated into methylene chloride (MC), ethyl acetate (EA), and water (WT) fractions, and high-performance liquid chromatography with photodiode array detection (HPLC-DAD) analysis was performed. The main ultraviolet (UV)-absorbing phenolic compound contained in the EA fraction was identified as -coumaric acid by comparing the retention time and UV absorption spectrum with a standard. Silica gel column chromatography was performed to isolate a hydrophobic derivative of -coumaric acid contained in the MC fraction. Nuclear magnetic resonance (NMR) analysis identified the isolated compound as ethyl -coumarate. For comparative purposes, ethyl -coumarate was also chemically synthesized by the esterification reaction of -coumaric acid. The content of -coumaric acid and ethyl -coumarate in the total extract of hemp root was estimated to be 2.61 mg g and 6.47 mg g, respectively, by HPLC-DAD analysis. These values correspond to 84 mg Kg dry root and 216 mg Kg dry root, respectively. In conclusion, this study identified -coumaric acid and ethyl -coumarate as the main phenolic compounds contained in the hemp roots.

Citing Articles

Chemical Analysis of the Antihyperglycemic, and Pancreatic α-Amylase, Lipase, and Intestinal α-Glucosidase Inhibitory Activities of L. Seed Extracts.

Haddou S, Elrherabi A, Loukili E, Abdnim R, Hbika A, Bouhrim M Molecules. 2024; 29(1).

PMID: 38202676 PMC: 10779963. DOI: 10.3390/molecules29010093.

Protective Effects of Hemp () Root Extracts against Insulin-Deficient Diabetes Mellitus In Mice.

Kim Y, Kim W, Kim S, Sim K, Kim K, Cho K Molecules. 2023; 28(9).

PMID: 37175224 PMC: 10179809. DOI: 10.3390/molecules28093814.

Recent Research on L.: Phytochemistry, New Matrices, Cultivation Techniques, and Recent Updates on Its Brain-Related Effects (2018-2023).

Siracusa L, Ruberto G, Cristino L Molecules. 2023; 28(8).

PMID: 37110621 PMC: 10146690. DOI: 10.3390/molecules28083387.

References

Song K, An S, Kim M, Koh J, Boo Y . Comparison of the antimelanogenic effects of p-coumaric acid and its methyl ester and their skin permeabilities. J Dermatol Sci. 2011; 63(1):17-22. DOI: 10.1016/j.jdermsci.2011.03.012. View

Lee S, Mun G, An S, Boo Y . Evidence for the association of peroxidases with the antioxidant effect of p-coumaric acid in endothelial cells exposed to high glucose plus arachidonic acid. BMB Rep. 2009; 42(9):561-7. DOI: 10.5483/bmbrep.2009.42.9.561. View

An S, Lee S, Choi S, Moon S, Boo Y . p-Coumaric acid, a constituent of Sasa quelpaertensis Nakai, inhibits cellular melanogenesis stimulated by alpha-melanocyte stimulating hormone. Br J Dermatol. 2008; 159(2):292-9. DOI: 10.1111/j.1365-2133.2008.08653.x. View

Malfait A, Gallily R, Sumariwalla P, Malik A, Andreakos E, Mechoulam R . The nonpsychoactive cannabis constituent cannabidiol is an oral anti-arthritic therapeutic in murine collagen-induced arthritis. Proc Natl Acad Sci U S A. 2000; 97(17):9561-6. PMC: 16904. DOI: 10.1073/pnas.160105897. View

Lopes S, Yepes L, Perez-Castillo Y, Robledo S, de Sousa D . Alkyl and Aryl Derivatives Based on -Coumaric Acid Modification and Inhibitory Action against and . Molecules. 2020; 25(14). PMC: 7397144. DOI: 10.3390/molecules25143178. View

Izzo L, Castaldo L, Narvaez A, Graziani G, Gaspari A, Rodriguez-Carrasco Y . Analysis of Phenolic Compounds in Commercial L. Inflorescences Using UHPLC-Q-Orbitrap HRMS. Molecules. 2020; 25(3). PMC: 7037164. DOI: 10.3390/molecules25030631. View

Nigro E, Crescente G, Formato M, Pecoraro M, Mallardo M, Piccolella S . Hempseed Lignanamides Rich-Fraction: Chemical Investigation and Cytotoxicity towards U-87 Glioblastoma Cells. Molecules. 2020; 25(5). PMC: 7179246. DOI: 10.3390/molecules25051049. View

Pei K, Ou J, Huang J, Ou S . p-Coumaric acid and its conjugates: dietary sources, pharmacokinetic properties and biological activities. J Sci Food Agric. 2015; 96(9):2952-62. DOI: 10.1002/jsfa.7578. View

Russo E, Guy G . A tale of two cannabinoids: the therapeutic rationale for combining tetrahydrocannabinol and cannabidiol. Med Hypotheses. 2005; 66(2):234-46. DOI: 10.1016/j.mehy.2005.08.026. View

10.

Andre C, Hausman J, Guerriero G . Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016; 7:19. PMC: 4740396. DOI: 10.3389/fpls.2016.00019. View

11.

Smeriglio A, Galati E, Monforte M, Lanuzza F, DAngelo V, Circosta C . Polyphenolic Compounds and Antioxidant Activity of Cold-Pressed Seed Oil from Finola Cultivar of Cannabis sativa L. Phytother Res. 2016; 30(8):1298-307. DOI: 10.1002/ptr.5623. View

12.

Ryz N, Remillard D, Russo E . Cannabis Roots: A Traditional Therapy with Future Potential for Treating Inflammation and Pain. Cannabis Cannabinoid Res. 2017; 2(1):210-216. PMC: 5628559. DOI: 10.1089/can.2017.0028. View

13.

Lima Filho A, Silva I, Sousa F, de Souza L, Gomes B, Gomes Goncalves R . Inhibition of neutrophil migration and reduction of oxidative stress by ethyl p-coumarate in acute and chronic inflammatory models. Phytomedicine. 2019; 57:9-17. DOI: 10.1016/j.phymed.2018.09.034. View

14.

Elhendawy M, Wanas A, Radwan M, Azzaz N, Toson E, ElSohly M . Chemical and Biological Studies of Roots. Med Cannabis Cannabinoids. 2020; 1(2):104-111. PMC: 7158750. DOI: 10.1159/000495582. View

15.

Kilic I, Yesiloglu Y . Spectroscopic studies on the antioxidant activity of p-coumaric acid. Spectrochim Acta A Mol Biomol Spectrosc. 2013; 115:719-24. DOI: 10.1016/j.saa.2013.06.110. View

16.

Sethi V, Jain M, Thakur R . Chemical investigation of wild Cannabis sativa L. roots. Planta Med. 1977; 32(4):378-9. DOI: 10.1055/s-0028-1097617. View

17.

Jin D, Henry P, Shan J, Chen J . Identification of Chemotypic Markers in Three Chemotype Categories of Cannabis Using Secondary Metabolites Profiled in Inflorescences, Leaves, Stem Bark, and Roots. Front Plant Sci. 2021; 12:699530. PMC: 8283674. DOI: 10.3389/fpls.2021.699530. View

18.

Gul W, Gul S, Chandra S, Lata H, Ibrahim E, ElSohly M . Detection and Quantification of Cannabinoids in Extracts of Cannabis sativa Roots Using LC-MS/MS. Planta Med. 2018; 84(4):267-271. DOI: 10.1055/s-0044-100798. View

19.

Lima K, Eduarda Gomes da Cruz Silva M, Cicero de Lima Araujo T, Silva C, Santos B, de Araujo Ribeiro L . Cannabis roots: Pharmacological and toxicological studies in mice. J Ethnopharmacol. 2021; 271:113868. DOI: 10.1016/j.jep.2021.113868. View

20.

Ha J, Boo Y . Siegesbeckiae Herba Extract and Chlorogenic Acid Ameliorate the Death of HaCaT Keratinocytes Exposed to Airborne Particulate Matter by Mitigating Oxidative Stress. Antioxidants (Basel). 2021; 10(11). PMC: 8615115. DOI: 10.3390/antiox10111762. View