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Conversion Characteristics of Some Major Cannabinoids from Hemp (Cannabis Sativa L.) Raw Materials by New Rapid Simultaneous Analysis Method

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Conversion Characteristics of Some Major Cannabinoids from Hemp (Cannabis Sativa L.) Raw Materials by New Rapid Simultaneous Analysis Method molecules Article Conversion Characteristics of Some Major Cannabinoids from Hemp (Cannabis sativa L.) Raw Materials by New Rapid Simultaneous Analysis Method Byeong Ryeol Ryu 1,† , Md. Jahirul Islam 1,2,† , Md. Obyedul Kalam Azad 1 , Eun-Ji Go 1, Md. Hafizur Rahman 1, Md. Soyel Rana 1, Young-Seok Lim 1,* and Jung-Dae Lim 1,* 1 Department of Bio-Health Convergence, Kangwon National University, Chuncheon 24341, Korea; [email protected] (B.R.R.); [email protected] (M.J.I.); [email protected] (M.O.K.A.); [email protected] (E.-J.G.); hafi[email protected] (M.H.R.); [email protected] (M.S.R.) 2 Physiology and Sugar Chemistry Division, Bangladesh Sugarcrop Research Institute, Ishurdi, Pabna 6620, Bangladesh * Correspondence: [email protected] (Y.-S.L.); [email protected] (J.-D.L.); Tel.: +82-33-250-6474 (Y.-S.L.); +82-33-540-3323 (J.-D.L.) † These authors contribute equally. Abstract: This study was carried out to develop a high-performance liquid chromatography method for short-time analysis of the main cannabinoids in the inflorescence of hemp (Cannabis sativa L.). We also performed decarboxylation of the raw material using our advanced analysis technique. In this study, the UV spectrum was considered to analyze each of the four common cannabinoids, solvents, and samples, where the uniform elution of acidic cannabinoids without peak tailing and Citation: Ryu, B.R.; Islam, M..J.; acids was tested. Optimal results were obtained when readings were taken at a wavelength of 220 nm Azad, M..O.K.; Go, E.-J.; Rahman, using water and methanol containing trifluoroacetic acid as mobile phases in a solvent gradient M..H.; Rana, M..S.; Lim, Y.-S.; Lim, J.-D. Conversion Characteristics of system. The established conditions were further validated by system suitability, linearity, precision, Some Major Cannabinoids from detection limit, and quantitation limit tests. The decarboxylation index (DT50) confirmed that D9- Hemp (Cannabis sativa L.) Raw THCA decarboxylated faster than CBDA, and both maintained a linear relationship with time and Materials by New Rapid temperature. In addition, the loss of cannabidiol was better prevented during the decarboxylation Simultaneous Analysis Method. process in the natural state than in the extracted state. Molecules 2021, 26, 4113. https:// doi.org/10.3390/molecules26144113 Keywords: cannabis; decarboxylation; cannabinoid; chromatography; cannabidiol Academic Editor: Andrea Mastinu Received: 16 June 2021 1. Introduction Accepted: 4 July 2021 Published: 6 July 2021 Linnaeus classified hemp in Europe as a single species (Cannabis sativa L.) [1], and de Lamarck separately classified Indian varieties as Cannabis indica Lam. [2]. Janischevsky Cannabis ruderalis Publisher’s Note: MDPI stays neutral classified Russian-born hemp as Jansich. without any characteristics [3]. with regard to jurisdictional claims in Even today, it remains controversial whether all cannabis should be viewed as a single published maps and institutional affil- species of C. sativa or as multiple species divided into C. sativa, C. indica, and C. ruderalis [4]. iations. For convenience, it is indicated as ‘Cannabis sativa L.’. Hemp (Cannabis sativa L.) is an annual herb belonging to the Cannabaceae family, first recorded in China for the purpose of obtaining fiber [5]. Since then, it has been exploited for medical purposes for more than 10,000 years [6]. As many countries have approved hemp for medical applications, there has been a surge in the use of hemp drug Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. therapy for pain relief [7]. Hemp contains more than 525 compounds and is known to This article is an open access article express approximately 109 cannabinoids [8]. Cannabinoid refers to the C21 terpenophenol distributed under the terms and compound uniquely found in hemp [9]. Although expressed in small amounts in leaves, conditions of the Creative Commons cannabinoid is mostly concentrated in the trichome part distributed in the bracts of the Attribution (CC BY) license (https:// female flower of the plant. Its concentration is higher in the stalked-type trichome among creativecommons.org/licenses/by/ the two types, ‘sessile’ and ‘stalked’ [10]. They are mostly present in the resin secreted from 4.0/). the trichomes of female plants, while male C. sativa have few glandular trichomes that can Molecules 2021, 26, 4113. https://doi.org/10.3390/molecules26144113 https://www.mdpi.com/journal/molecules Molecules 2021, 26, x FOR PEER REVIEW 2 of 11 the two types, ‘sessile’ and ‘stalked’ [10]. They are mostly present in the resin secreted Molecules 2021, 26, 4113 from the trichomes of female plants, while male C. sativa have few glandular2 oftrichomes 11 that can produce small amounts of psychoactive molecules [11]. The most abundant of these are the ∆9-tetrahydrocannabinol (∆9-THC) and cannabidiol (CBD) families [12]. The compoundproduce small ∆9-THC amounts is a of major psychoactive psychotropic molecules cannabinoid [11]. The most [13] abundant known of to these induce are thetransient psychoticD9-tetrahydrocannabinol and anxiety symptoms (D9-THC) [14,15]. and cannabidiol It was recently (CBD) families found to [12 be]. The effective compound in treating D9-THC is a major psychotropic cannabinoid [13] known to induce transient psychotic and Alzheimer’s disease and glaucoma [5]. CBD has an effect on anti-anxiety and anti-psychi- anxiety symptoms [14,15]. It was recently found to be effective in treating Alzheimer’s atricdisease diseases and glaucoma[16,17], and [5]. more CBD hasthan an 1000 effect CBD-containing on anti-anxiety andproducts anti-psychiatric are available dis- in the market.eases [16 It, 17is ],thought and more to thancontain 1000 ingredients CBD-containing that productscan cure are mental available illness in the [18]. market. Each Itof these neutralis thought cannabinoids to contain ingredientsis formed thatby non-enzy can cure mentalmatic illnessdecarboxylation [18]. Each of of these acidic neutral precursor cannabinoidscannabinoids called is formed Δ9-tetrahydrocannabinolic by non-enzymatic decarboxylation acid (∆9-THCA) of acidic precursorand cannabidiolic cannabi- acid (CBDA)noids called (FigureD9-tetrahydrocannabinolic 1) [19,20], and heating acid temperature (D9-THCA) and and time cannabidiolic are known acid to (CBDA) significantly influence(Figure1 )[this19 ,decarboxylation20], and heating temperature process [21]. and time are known to significantly influence this decarboxylation process [21]. FigureFigure 1. 1.CarboxylCarboxyl group group of acid of cannabinoids. acid cannabinoids. (A) Cannabidiolic (A) Cannabidiolic acid, (B) acid,∆9-tetrahydrocanna- (B) D9- binolictetrahydrocannabinolic acid. Carboxyl groups acid. Carboxyl are removed groups by are he removedat treatment by heat and treatment converted and converted into neutral into canna- binoids.neutral cannabinoids. In this study, high-performance liquid chromatography (HPLC) was used to efficiently andIn accurately this study, quantify high-performance four major cannabinoids liquid chromatography (D9-THC, D9-THCA, (HPLC) CBD, was and CBDA)used to effi- cientlythat can and be accurately naturally and quantify artificially four converted. major cannabinoids These compounds (∆9-THC, exhibit ∆9-THCA, physiological CBD, and CBDA)activities. that Simultaneous can be naturally analysis and conditions artificially were converted. developed, These established, compounds and employed exhibit to physio- logicalstudy activities. the decarboxylation Simultaneous of cannabis analysis inflorescence. conditions were developed, established, and em- ployed to study the decarboxylation of cannabis inflorescence. 2. Materials and Methods 2.1. Standard and Sample Preparation 2. Materials and Methods A sample of the inflorescence part of cannabis (Cannabis sativa L.) was received from 2.1.the Standard Korea Cannabis and Sample Genetic Preparation Resource Center (Chuncheon, Korea). An inflorescence sample of aA plant sample grown of the for 105inflorescence days (50 days part after of cannabis flowering (Cannabis treatment) sativa in a nutrientL.) was solutionreceived from thecultivation Korea Cannabis system afterGenetic sowing Resource was used. Center The (Chuncheon, standard products Korea). cannabidiol An inflorescence (CBD) sam- pleand of Da9-tetrahydrocannabinol plant grown for 105 days (D9-THC) (50 days were afte obtainedr flowering from treatment) CAYMAN (Annin a nutrient Arbor, MI, solution cultivationUSA), the cannabidiolicsystem after acidsowing (CBDA) was standardused. Th producte standard was fromproducts Cerilliant cannabidiol (Round Rock,(CBD) and TX, USA), and the D9-tetrahydrocannabinolic acid (D9-THCA) standard product was Δ9-tetrahydrocannabinol (∆9-THC) were obtained from CAYMAN (Ann Arbor, MI, manufactured by Sigma-Aldrich (St. Louis, MO, USA). USA), Thethe inflorescencecannabidiolic of acid freeze-dried (CBDA) hempstandard was pulverizedproduct was using from a chopper Cerilliant (YPT-1402, (Round Rock, TX,Young USA), Polymer and Techthe Δ Co.,9-tetrahydrocannabinolic Incheon, Korea) certified byacid Korea (∆9-THCA) Conformity standard Laboratories product and was manufacturedfiltered through by a 12-meshSigma-Aldrich test sieve. (St. The Louis, furnace MO, particles USA). were found to be homogeneous. In brief,The inflorescence 0.1 g of hemp sampleof freeze-dried was sonicated hemp (JEIO was TECHpulverized Co., Ltd., using Daejeon, a chopper Korea) (YPT-1402, for Young30 min Polymer with 30 Tech mL extra Co.,
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