Tags

Type your tag names separated by a space and hit enter

Isolation, Purification, and Antimicrobial Characterization of Cannabidiolic Acid and Cannabidiol from Cannabis sativa L.
Biomolecules. 2020 06 12; 10(6)B

Abstract

The emergence of multi-drug resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA) causes a major threat to public health due to its limited therapeutic options. There is an urgent need for the development of new effective antimicrobial agents and alternative strategies that are effective against resistant bacteria. The parallel legalization of cannabis and its products has fueled research into its many therapeutic avenues in many countries around the world. This study aimed at the development of a reliable method for the extraction, purification, characterization, and quantification of cannabidiolic acid (CBDA) and its decarboxylated form cannabidiol (CBD) present in the fiber type Cannabis sativa L. The two compounds were extracted by ethanol, purified on a C18 sep-pack column, and the extracts were analyzed by high performance liquid chromatography coupled with ultraviolet (UV)-vis and ESI-MS (electrospray ionization mass spectrometry) detection. The antimicrobial effect of CBDA and CBD was also evaluated. CBD displayed a substantial inhibitory effect on Gram-positive bacteria with minimal inhibitory concentrations ranging from 1 to 2 µg/mL. Time kill analysis and minimal bactericidal concentration revealed potential bactericidal activity of CBDA and CBD. While cannabinoids showed a significant antimicrobial effect on the Gram-positive S. aureus and Staphylococcus epidermidis, no activity was noticed on Gram-negative Escherichia coli and Pseudomonas aeruginosa. CBDA presented a two-fold lower antimicrobial activity than its decarboxylated form, suggesting that the antimicrobial pharmacophore of the analyzed cannabinoids falls in the ability for permeabilizing the bacterial cell membrane and acting as a detergent-like agent. A synergy test performed on MRSA with CBD and a range of antibiotics did not indicate a synergetic effect, but noteworthy no antagonist influence either. CBD and CBDA manifested low hemolytic activity on human red blood cells. Likewise, the safety of CBD toward human keratinocyte cells presents no toxicity at a concentration of up to seven-fold higher than the antibacterial minimal inhibitory concentration. Similarly, both CBD and CBDA are well tolerated by mammals, including humans, and conserve a safe value limits for blood-contacting drug development. Overall, CBD exhibited a strong antimicrobial effect against Gram-positive strains and could serve as an alternative drug for tackling MRSA.

Authors+Show Affiliations

Department of Science and Environment, Roskilde University, 4000 Roskilde, Denmark.Department of Science and Environment, Roskilde University, 4000 Roskilde, Denmark.Department of Science and Environment, Roskilde University, 4000 Roskilde, Denmark.Department of Science and Environment, Roskilde University, 4000 Roskilde, Denmark.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

32545687

Citation

Martinenghi, Laura Daniela, et al. "Isolation, Purification, and Antimicrobial Characterization of Cannabidiolic Acid and Cannabidiol From Cannabis Sativa L." Biomolecules, vol. 10, no. 6, 2020.
Martinenghi LD, Jønsson R, Lund T, et al. Isolation, Purification, and Antimicrobial Characterization of Cannabidiolic Acid and Cannabidiol from Cannabis sativa L. Biomolecules. 2020;10(6).
Martinenghi, L. D., Jønsson, R., Lund, T., & Jenssen, H. (2020). Isolation, Purification, and Antimicrobial Characterization of Cannabidiolic Acid and Cannabidiol from Cannabis sativa L. Biomolecules, 10(6). https://doi.org/10.3390/biom10060900
Martinenghi LD, et al. Isolation, Purification, and Antimicrobial Characterization of Cannabidiolic Acid and Cannabidiol From Cannabis Sativa L. Biomolecules. 2020 06 12;10(6) PubMed PMID: 32545687.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isolation, Purification, and Antimicrobial Characterization of Cannabidiolic Acid and Cannabidiol from Cannabis sativa L. AU - Martinenghi,Laura Daniela, AU - Jønsson,Rie, AU - Lund,Torben, AU - Jenssen,Håvard, Y1 - 2020/06/12/ PY - 1970/01/01/received PY - 2020/06/09/revised PY - 2020/06/10/accepted PY - 2020/6/18/entrez PY - 2020/6/18/pubmed PY - 2021/4/2/medline KW - Cannabis sativa L KW - HPLC KW - Staphyloccoccus KW - antibacterial KW - cannabidiol KW - cannabidiolic acid KW - cannabinoids KW - cannabis KW - snergy JF - Biomolecules JO - Biomolecules VL - 10 IS - 6 N2 - The emergence of multi-drug resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA) causes a major threat to public health due to its limited therapeutic options. There is an urgent need for the development of new effective antimicrobial agents and alternative strategies that are effective against resistant bacteria. The parallel legalization of cannabis and its products has fueled research into its many therapeutic avenues in many countries around the world. This study aimed at the development of a reliable method for the extraction, purification, characterization, and quantification of cannabidiolic acid (CBDA) and its decarboxylated form cannabidiol (CBD) present in the fiber type Cannabis sativa L. The two compounds were extracted by ethanol, purified on a C18 sep-pack column, and the extracts were analyzed by high performance liquid chromatography coupled with ultraviolet (UV)-vis and ESI-MS (electrospray ionization mass spectrometry) detection. The antimicrobial effect of CBDA and CBD was also evaluated. CBD displayed a substantial inhibitory effect on Gram-positive bacteria with minimal inhibitory concentrations ranging from 1 to 2 µg/mL. Time kill analysis and minimal bactericidal concentration revealed potential bactericidal activity of CBDA and CBD. While cannabinoids showed a significant antimicrobial effect on the Gram-positive S. aureus and Staphylococcus epidermidis, no activity was noticed on Gram-negative Escherichia coli and Pseudomonas aeruginosa. CBDA presented a two-fold lower antimicrobial activity than its decarboxylated form, suggesting that the antimicrobial pharmacophore of the analyzed cannabinoids falls in the ability for permeabilizing the bacterial cell membrane and acting as a detergent-like agent. A synergy test performed on MRSA with CBD and a range of antibiotics did not indicate a synergetic effect, but noteworthy no antagonist influence either. CBD and CBDA manifested low hemolytic activity on human red blood cells. Likewise, the safety of CBD toward human keratinocyte cells presents no toxicity at a concentration of up to seven-fold higher than the antibacterial minimal inhibitory concentration. Similarly, both CBD and CBDA are well tolerated by mammals, including humans, and conserve a safe value limits for blood-contacting drug development. Overall, CBD exhibited a strong antimicrobial effect against Gram-positive strains and could serve as an alternative drug for tackling MRSA. SN - 2218-273X UR - https://www.unboundmedicine.com/medline/citation/32545687/Isolation_Purification_and_Antimicrobial_Characterization_of_Cannabidiolic_Acid_and_Cannabidiol_from_Cannabis_sativa_L_ L2 - https://www.mdpi.com/resolver?pii=biom10060900 DB - PRIME DP - Unbound Medicine ER -