Radwa Mahmoud, Amir Khajavinia, Sedigheh Barzegar, Randy W. Purves, Robert B. Laprairie, Anas El-Aneed
{"title":"电喷雾正离子模式下最常见植物大麻素质谱指纹图谱的建立。","authors":"Radwa Mahmoud, Amir Khajavinia, Sedigheh Barzegar, Randy W. Purves, Robert B. Laprairie, Anas El-Aneed","doi":"10.1002/rcm.9952","DOIUrl":null,"url":null,"abstract":"<div>\n \n \n <section>\n \n <h3> Background</h3>\n \n <p>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.</p>\n </section>\n \n <section>\n \n <h3> Materials and Methods</h3>\n \n <p>Eight phytocannabinoids, namely, ∆<sup>9</sup>-tetrahydrocannabinol (THC), cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), tetrahydrocannabivarin (THCV), 11-hydroxy-Δ<sup>9</sup>-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 (MS<sup>3</sup>) analyses.</p>\n </section>\n \n <section>\n \n <h3> Results</h3>\n \n <p>An abundant, singly charged [M + H]<sup>+</sup> 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 MS<sup>3</sup> experiments.</p>\n </section>\n \n <section>\n \n <h3> Conclusions</h3>\n \n <p>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.</p>\n </section>\n </div>","PeriodicalId":225,"journal":{"name":"Rapid Communications in Mass Spectrometry","volume":"39 4","pages":""},"PeriodicalIF":1.8000,"publicationDate":"2024-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Establishment of a Mass Spectrometric Fingerprint of the Most Common Phytocannabinoids in Electrospray Ionization in Positive Ion Mode\",\"authors\":\"Radwa Mahmoud, Amir Khajavinia, Sedigheh Barzegar, Randy W. Purves, Robert B. Laprairie, Anas El-Aneed\",\"doi\":\"10.1002/rcm.9952\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n \\n <section>\\n \\n <h3> Background</h3>\\n \\n <p>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.</p>\\n </section>\\n \\n <section>\\n \\n <h3> Materials and Methods</h3>\\n \\n <p>Eight phytocannabinoids, namely, ∆<sup>9</sup>-tetrahydrocannabinol (THC), cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), tetrahydrocannabivarin (THCV), 11-hydroxy-Δ<sup>9</sup>-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 (MS<sup>3</sup>) analyses.</p>\\n </section>\\n \\n <section>\\n \\n <h3> Results</h3>\\n \\n <p>An abundant, singly charged [M + H]<sup>+</sup> 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 MS<sup>3</sup> experiments.</p>\\n </section>\\n \\n <section>\\n \\n <h3> Conclusions</h3>\\n \\n <p>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.</p>\\n </section>\\n </div>\",\"PeriodicalId\":225,\"journal\":{\"name\":\"Rapid Communications in Mass Spectrometry\",\"volume\":\"39 4\",\"pages\":\"\"},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-12-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Rapid Communications in Mass Spectrometry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/rcm.9952\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMICAL RESEARCH METHODS\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Rapid Communications in Mass Spectrometry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/rcm.9952","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMICAL RESEARCH METHODS","Score":null,"Total":0}
Establishment of a Mass Spectrometric Fingerprint of the Most Common Phytocannabinoids in Electrospray Ionization in Positive Ion Mode
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.
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.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
