Establishment of a Mass Spectrometric Fingerprint of the Most Common Phytocannabinoids in Electrospray Ionization in Positive Ion Mode

IF 1.8 3区化学 Q4 BIOCHEMICAL RESEARCH METHODS Rapid Communications in Mass Spectrometry Pub Date : 2024-12-14 DOI:10.1002/rcm.9952

Radwa Mahmoud, Amir Khajavinia, Sedigheh Barzegar, Randy W. Purves, Robert B. Laprairie, Anas El-Aneed

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Abstract

Background

Analysis of the phytocannabinoids holds significant importance because of their various pharmacological properties and potential therapeutic applications. Tandem mass spectrometry (MS/MS) coupled with electrospray ionization in positive ion mode is employed in this study to describe the collision-induced dissociation (CID) behavior of a series of common phytocannabinoids with the aim of establishing a generalized MS/MS fingerprint.

Materials and Methods

Eight phytocannabinoids, namely, ∆⁹-tetrahydrocannabinol (THC), cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), tetrahydrocannabivarin (THCV), 11-hydroxy-Δ⁹-tetrahydrocannabinol (11-OH-THC), 6-hydroxy-cannabidiol (6-OH-CBD), and 7-hydroxy-cannabidiol (7-OH-CBD), were studied. A Quadrupole-Orbitrap mass spectrometer equipped with a heated electrospray ionization (HESI-Q Orbitrap) is used to provide accurate mass measurement data for single-stage and MS/MS analysis. In addition, a triple quadrupole-linear ion trap mass spectrometer was used to perform MS/MS and second-generation MS/MS (MS³) analyses.

Results

An abundant, singly charged [M + H]⁺ species during single-stage MS analysis was observed for all phytocannabinoids, with mass accuracies less than 5 ppm. Because of their structural similarities, all compounds showed some common fragmentation behavior in their MS/MS analysis. By comparing the fragmentation patterns and identifying diagnostic ions, a universal MS/MS fragmentation pattern was established. The structures of the various product ions proposed in the fragmentation pathway were confirmed with exact mass measurements and MS³ experiments.

Conclusions

The evaluated compounds contain varying functional groups, resulting in unique product ions, specific to each structure. The MS/MS fingerprints will be utilized in the future for the identification of new structures as well as the development of targeted quantification methods.

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背景：由于植物大麻素具有多种药理特性和潜在的治疗用途，因此对其进行分析具有重要意义。本研究采用串联质谱（MS/MS）结合电喷雾离子化正离子模式，描述了一系列常见植物大麻素的碰撞诱导解离（CID）行为，旨在建立一个通用的 MS/MS 指纹：研究了 11-羟基-Δ9-四氢大麻酚（11-OH-THC）、6-羟基-大麻二酚（6-OH-CBD）和 7-羟基-大麻二酚（7-OH-CBD）。使用配备加热电喷雾离子化装置（HESI-Q Orbitrap）的四极杆-轨道阱质谱仪为单级和 MS/MS 分析提供精确的质量测量数据。此外，还使用三重四极杆线性离子阱质谱仪进行 MS/MS 和第二代 MS/MS (MS3) 分析：结果：在单级质谱分析过程中，所有植物大麻素都观察到了丰富的单电荷[M + H]+ 物种，质量精确度低于 5 ppm。由于结构相似，所有化合物在 MS/MS 分析中都表现出一些共同的碎片行为。通过比较碎片模式和识别诊断离子，建立了通用的 MS/MS 碎片模式。通过精确的质量测量和 MS3 实验，确认了碎片路径中提出的各种产物离子的结构：结论：所评估的化合物含有不同的官能团，从而产生了针对每种结构的独特产物离子。今后将利用 MS/MS 指纹来鉴定新结构，并开发有针对性的定量方法。

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来源期刊

Rapid Communications in Mass Spectrometry 化学-分析化学

CiteScore

4.10

自引率

5.00%

发文量

219

审稿时长

2.6 months

期刊介绍： Rapid Communications in Mass Spectrometry is a journal whose aim is the rapid publication of original research results and ideas on all aspects of the science of gas-phase ions; it covers all the associated scientific disciplines. There is no formal limit on paper length ("rapid" is not synonymous with "brief"), but papers should be of a length that is commensurate with the importance and complexity of the results being reported. Contributions may be theoretical or practical in nature; they may deal with methods, techniques and applications, or with the interpretation of results; they may cover any area in science that depends directly on measurements made upon gaseous ions or that is associated with such measurements.