Investigation of retention behavior of natural cannabinoids on differently substituted polysaccharide-based chiral stationary phases under reversed-phase liquid chromatographic conditions

Luca, Chiara De; Buratti, Alessandro; Umstead, Weston J.; Franco, Pilar; Cavazzini, Alberto; Felletti, Simona; Catani, Martina

doi:10.1016/j.chroma.2022.463076

Cited by 15 publications

(10 citation statements)

References 37 publications

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“…Evidence showing that both reversed-phase and normal-phase chiral HPLC can be used for enantio-purification based on polysaccharide stationary phases is reported in some recently published studies (49)(50)(51).…”

Section: Chirality Of Cannabinoids Has Been Knownmentioning

confidence: 99%

Purification and Isolation of Cannabinoids: Current Challenges and Perspectives

et al. 2023

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The recent legalization of cannabis in many countries and its increased use in scientific and medical research as a result of its therapeutic properties have focused attention on the need for large quantities of highly purified cannabinoids. This is particularly important for the production of (new) analytical-grade standards, used as reference materials, and for the execution of clinical trials to test the biological activity of the single compounds that could potentially be used as new drugs or active pharmaceutical ingredients (APIs). To date, various purification strategies, usually based on several steps, have been proposed with different outcomes. However, all these methods have both advantages and disadvantages. This review will report on the challenges and future perspectives in the purification and isolation of major and minor cannabinoids from cannabis extracts.

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Section: Chirality Of Cannabinoids Has Been Knownmentioning

confidence: 99%

Purification and Isolation of Cannabinoids: Current Challenges and Perspectives

et al. 2023

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“…De Luca et al published a paper in 2022, which covered the screening on all available immobilized-type CSPs available from Daicel Corporation (at the time of publication). They found CHIRALPAK IC and IF to be very effective at the separation of a mixture containing cannabidiolic acid (CDBA), cannabidiol (CBD), tetrahydrocannabidiolic acid (THCA), CBC (racemic), and Δ 9 THC [67]. Because CBC is a racemic cannabinoid, two peaks were observed (Figure 7), with good baseline resolution for all cannabinoids.…”

Section: High Performance Liquid Chromatography (Hplc) Separationsmentioning

confidence: 99%

“…Figure 7.Reversed phase separation of CBDA, CBD, THC, CBC, and THCA with CHIRALPAK IC (in blue) and IF (in red). Adapted from ref [67]. with author permission.…”

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confidence: 99%

Polysaccharide Chiral Stationary Phases for the Achiral and Chiral Separation of Cannabinoids

Umstead¹

2023

Cannabinoids - Recent Perspectives and Applications in Human Health

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Polysaccharide-based chiral stationary phases (CSPs) have been widely utilized in the pharmaceutical, agricultural, and natural product industries since their first-reported use and subsequent commercialization more than 50 years ago. Although they have been traditionally used for the separation of small drug molecules containing one or more chiral centers, their uses have recently grown to include achiral separations in emerging fields like the cannabis industry. The ability to separate and study individual cannabinoids is critical to understanding their impact in both medicinal and recreational applications. Furthermore, it is not difficult to envision a future where cannabinoids, particularly for medicinal use, are treated like pharmaceuticals—that is requiring rigorous purity testing, including the determination of chiral purity. While current methods of analysis are sufficient for the separation of achiral cannabinoid mixtures, some critical chiral pairs like cannabichromene cannot be separated fully. This is where the use of polysaccharide CSPs is and will continue to be important, as a chiral resolution will be needed to satisfy these potential requirements. This chapter will cover an introduction and evolution of polysaccharide CSPs, including a discussion on their unique separations mechanism, and review a number of the applications described in the literature of their uses for the achiral and chiral separation of cannabinoids.

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“…This was followed by a considerable lull until the late 2000s and into the 2010s. More recently, the activity has picked up not only for chiral separations of cannabinoids but also for the achiral separation of cannabinoid mixtures on polysaccharide CSPs [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ]. Unlike the many non-chiral methods on C18 or silica, chiral phases can achieve a mixed-mode separation of both chiral and non-chiral, making them a powerful tool for complex separations.…”

Section: Introductionmentioning

confidence: 99%

Chiral Separation of Cannabichromene, Cannabicyclol, and Their Acidic Analogs on Polysaccharide Chiral Stationary Phases

Ferraro¹,

Umstead²

2023

Molecules

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Until recently, chirality has not been a major focus in the study of cannabinoids, as most cannabinoids of interest, such as cannabidiol and tetrahydrocannabinol, exist as a single isomer from natural sources. However, this is changing as more cannabinoids are identified, and compounds such as cannabichromene and cannabicyclol are emerging as potential investigatory candidates for varying indications. Because these molecules are chiral, the separation and study of the individual enantiomers’ biological and physiological effects should therefore be of interest. The purpose of this study was to identify analytical separation conditions and then adapt those conditions to preparative separation. This was accomplished with a column-screening approach on Daicel’s immobilized polysaccharide chiral stationary phases using non-traditional mobile phases, which included dichloromethane, ethyl acetate, and methyl tert-butyl ether under high-performance liquid chromatography conditions. CHIRALPAK® IK was found to separate all four compounds well with mobile phases containing hexane-dichloromethane (with or without an acidic additive). From these methods, the separation productivities were calculated to better visualize the separation scalability, which shows that the kilogram-scale separations of each are feasible.

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Investigation of retention behavior of natural cannabinoids on differently substituted polysaccharide-based chiral stationary phases under reversed-phase liquid chromatographic conditions

Cited by 15 publications

References 37 publications

Purification and Isolation of Cannabinoids: Current Challenges and Perspectives

Purification and Isolation of Cannabinoids: Current Challenges and Perspectives

Polysaccharide Chiral Stationary Phases for the Achiral and Chiral Separation of Cannabinoids

Chiral Separation of Cannabichromene, Cannabicyclol, and Their Acidic Analogs on Polysaccharide Chiral Stationary Phases

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