Journal:Analysis of phenolic compounds in commercial Cannabis sativa L. inflorescences using UHPLC-Q-Orbitrap HRMS

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Full article title Analysis of phenolic compounds in commercial Cannabis sativa L. inflorescences using UHPLC-Q-Orbitrap HRMS
Journal Molecules
Author(s) Izzo, Luana; Castaldo, Luigi; Narváez, Alfonso; Graziani, Giulia; Gaspari, Anna; Rodríguez-Carrasco, Yelko; Ritieni, Alberto
Author affiliation(s) University of Naples "Federico II," University of Valencia
Primary contact Email: luana dot izzo at unina dot it
Editors Efferth, Thomas
Year published 2020
Volume and issue 25(3)
Article # 631
DOI 10.3390/molecules25030631
ISSN 1420-3049
Distribution license Creative Commons Attribution 4.0 International
Website https://www.mdpi.com/1420-3049/25/3/631/htm
Download https://www.mdpi.com/1420-3049/25/3/631/pdf (PDF)
Emblem-important-yellow.svg This article should be considered a work in progress and incomplete. Consider this article incomplete until this notice is removed.

Abstract

Industrial hemp (Cannabis sativa L., family Cannabaceae) contains a vast number of relevant bioactive organic compounds, namely polyphenols, including flavonoids, phenolic acids, phenol amides, and lignanamides, which are well known for their therapeutic properties. Nowadays, many polyphenol-containing products made from herbal extracts are marketed, claiming to have health-promoting effects. In this context, industrial hemp inflorescences may represent an innovative source of bioactive compounds to be used in nutraceutical formulations.

The aim of this work was to provide a comprehensive analysis of the polyphenolic fraction contained in polar extracts of four different commercial cultivars—Kompolti, Tiborszallasi, Antal, and Selected Carmagnola (CS)—of hemp inflorescence through spectrophotometric (total polyphenol content [TPC] and DPPH assays) and spectrometry measurement (using ultra high-performance liquid chromatography–quadrupole–orbitrap high-resolution mass spectrometry or UHPLC-Q-Orbitrap HRMS).

Results highlighted a high content of cannflavin A and B in inflorescence samples, which appear to be cannabis-specific, with a mean value of 61.8 and 84.5 mg/kg, meaning a ten-to-hundred times increase compared to other parts of the plant. Among flavonols, quercetin-3-glucoside reached up to 285.9 mg/kg in the CS cultivar. Catechin and epicatechin were the most representative flavanols, with a mean concentration of 53.3 and 66.2 mg/kg, respectively, for all cultivars. TPC in inflorescence samples was quantified in the range of 10.51 to 52.58 mg GAE/g, and free radical-scavenging included in the range from 27.5 to 77.6 mmol trolox/kg. As such, C. sativa inflorescence could be considered as a potential novel source of polyphenols intended for nutraceutical formulations.

Keywords: Cannabis sativa L., polyphenols, UHPLC-Q-Orbitrap HRMS

Introduction

Cannabis sativa is an annual herbaceous plant of the Cannabaceae family, native to Central Asia but with a wide distribution over different geographical areas, facilitated by climate adaptation. This plant has long been cultivated due to its large variety of applications, from textile uses to food and feed.[1]

Industrial hemp, characterized by a low content of psychoactive cannabinoids, contains bioactive organic compounds that are known to have a wide range of important biological properties.[2] Polyphenols represent one of the most relevant compounds found in C. sativa, including the likes of prenylated flavonoids, phenol amides, and lignanamides, which are specific metabolites of this plant. They are known to play multifunctional roles in the defense mechanisms of the plant, especially through their activity as antioxidants, preventing the generation of reactive oxygen species (ROS).[3][4][5][6] In humans, polyphenols can display health-promoting effects based on the modulation of several enzymes, such us lipoxygenase and the superfamily of cytochrome P450, showing cardio- or chemoprotective activity, among others.[5][7]

For this reason, polyphenol-containing products have been increasingly marketed as food supplements and nutraceuticals, and, currently, a great variety of supplements claiming to enhance specific physiological functions are commercially available. Nutraceuticals consist of naturally-occurring active substances, which are concentrated and administered in the suitable pharmaceutical form to properly develop its pharmacological effect. Furthermore, when compared to traditional drugs, nutraceuticals appear to be generally safer, with higher bioavailability and fewer side effects.[8] The manufacturing of nutraceuticals requires isolated ingredients that have to be extracted and purified for latter uses. Since certain polyphenols naturally occur inside insoluble structures, such as vacuoles, obtention of pure compounds can become a complex process.[9] In addition, several studies reported a decrease in the bioavailability and bioaccessibility of pure polyphenols in comparison with the administration of plant extracts rich in polyphenols, which may be due to the existence of other active compounds which can establish synergistic functions with them.[10][11][12] Because of this, food supplements could be a valuable resource to consume polyphenol-containing products. They consist of extracts from herbals and botanicals than can be delivered as the same pharmaceutical forms as nutraceuticals. Some of the most prevalent plants used as a source of polyphenols are tea, coffee, apple, basil, and turmeric, among others, each one intended for specific polyphenols.[13][14][15]

References

  1. ↑ Andre, C.M.; Hausman, J.F.; Guerriero, G. (2016). "Cannabis sativa: The Plant of the Thousand and One Molecules". Frontiers in Plant Science 7: 19. doi:10.3389/fpls.2016.00019. PMC PMC4740396. PMID 26870049. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4740396. 
  2. ↑ Cushnie, T.P.T.; Lamb, A.J. (2005). "Antimicrobial activity of flavonoids". International Journal of Antimicrobial Agents 26 (5): 343–56. doi:10.1016/j.ijantimicag.2005.09.002. PMC PMC7127073. PMID 16323269. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7127073. 
  3. ↑ Mkpenie, V.N.; Essien, E.E.; Udoh, I.I. (2012). "Effect of extraction conditions on total polyphenol contents, antioxidant and antimicrobial activities of Cannabis sativa L.". Electronic Journal of Environmental, Agricultural and Food Chemistry 11 (4): 300–307. https://www.researchgate.net/publication/260824507_Effect_of_extraction_conditions_on_total_polyphenol_contents_antioxidant_and_antimicrobial_activities_of_Cannabis_sativa_L. 
  4. ↑ Siano, F.; Moccia, S.; Picariello, G. et al. (2019). "Comparative Study of Chemical, Biochemical Characteristic and ATR-FTIR Analysis of Seeds, Oil and Flour of the Edible Fedora Cultivar Hemp (Cannabis sativa L.)". Molecules 24 (1): 83. doi:10.3390/molecules24010083. 
  5. ↑ 5.0 5.1 Pollastro, F.; Minassi, A.; Fresu, L.G. (2019). "Cannabis Phenolics and their Bioactivities". Current Medicinal Chemistry 25 (10): 1160–1185. doi:10.2174/0929867324666170810164636. 
  6. ↑ Mandal, S.M.; Chakraporty, D.; Dey, S. (2010). "Phenolic acids act as signaling molecules in plant-microbe symbioses". Plant Signaling & Behavior 5 (4): 359–68. doi:10.4161/psb.5.4.10871. 
  7. ↑ Castaldo, L.; Narváez, A.; Izzo, L. et al. (2019). "Red Wine Consumption and Cardiovascular Health". Molecules 24 (19): 3626. doi:10.3390/molecules24193626. PMC PMC6804046. PMID 31597344. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804046. 
  8. ↑ Santini, A.; Tenore, G.C.; Novellino, E. (2017). "Nutraceuticals: A paradigm of proactive medicine". European Journal of Pharmaceutical Sciences 96: 53–61. doi:10.1016/j.ejps.2016.09.003. PMID 27613382. 
  9. ↑ Kelly, N.P.; Kelly, A.L.; O'Mahony, J.A. (2019). "Strategies for enrichment and purification of polyphenols from fruit-based materials". Trends in Food Science & Technology 83: 248–58. doi:10.1016/j.tifs.2018.11.010. 
  10. ↑ Lin, J.; Teo, L.M.; Leong, L.P. et al. (2016). "In vitro bioaccessibility and bioavailability of quercetin from the quercetin-fortified bread products with reduced glycemic potential". Food Chemistry 286: 629–35. doi:10.1016/j.foodchem.2019.01.199. PMID 30827656. 
  11. ↑ Gómez-Juaristi, M.; Martínez-López, S.; Sarria, B. et al. (2018). "Bioavailability of hydroxycinnamates in an instant green/roasted coffee blend in humans. Identification of novel colonic metabolites". Food & Function 9 (1): 331-343. doi:10.1039/c7fo01553d. PMID 29177345. 
  12. ↑ Shukla, M.; Jaiswal, S.; Sharma, A. et al. (2017). "A combination of complexation and self-nanoemulsifying drug delivery system for enhancing oral bioavailability and anticancer efficacy of curcumin". Drug Development and Industrial Pharmacy 43 (5): 847–61. doi:10.1080/03639045.2016.1239732. PMID 27648633. 
  13. ↑ Abbas, M.; Saeed, F.; Anjum, F.M. et al. (2017). "Natural polyphenols: An overview". International Journal of Food Properties 20 (8): 1689–99. doi:10.1080/10942912.2016.1220393. 
  14. ↑ Tenore, G.C.; Campiglia, P.; Ciampaglia, R. et al. (2017). "Antioxidant and antimicrobial properties of traditional green and purple "Napoletano" basil cultivars (Ocimum basilicum L.) from Campania region (Italy)". Natural Product Research 31 (17): 2067–71. doi:10.1080/14786419.2016.1269103. PMID 28025898. 
  15. ↑ Castaldo, L.; Graziani, G.; Gaspari, A. et al. (2018). "Study of the Chemical Components, Bioactivity and Antifungal Properties of the Coffee Husk". Journal of Food Research 7 (4): 43–54. doi:10.5539/jfr.v7n4p43. 

Notes

This presentation is faithful to the original, with only a few minor changes to presentation. Some grammar and punctuation was cleaned up to improve readability. In some cases important information was missing from the references, and that information was added.

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