Validation and Quantitation of Fifteen Cannabinoids in Cannabis and Marketed Products Using High-Performance Liquid Chromatography-Ultraviolet/Photodiode Array Method.

Article

作者: Elhendawy, Mostafa A ; Ibrahim, Elsayed A ; Chandra, Suman ; Radwan, Mohamed M ; Wanas, Amira S ; ElSohly, Mahmoud A ; Godfrey, Murrell

Background: Cannabis sativa is a psychoactive plant indigenous to Central and South Asia, traditionally used both for recreational and religious purposes, in addition to folk medicine. Cannabis is a rich source of natural compounds, the most important of which are commonly known as cannabinoids that cause a variety of effects through interaction with the endocannabinoid system. Materials and Methods: In this study, a high-performance liquid chromatography-ultraviolet/photodiode array (PDA) method was developed and validated for the analysis of 15 cannabinoids in cannabis plant materials and cannabis-based marketed products. These cannabinoids are cannabidivarinic acid, cannabidivarin, cannabidiolic acid, cannabigerolic acid, cannabigerol, cannabidiol, delta-9-tetrahydrocannabivarin, delta-9-tetrahydrocannabivarinic acid, cannabinol, delta-9-tetrahyrocannabinol, delta-8-tetrahyrocannabinol, cannabicyclol, cannabichromene, delta-9-tetrahyrocannabinolic acid A, and cannabichromenic acid. The separation was carried out using a reversed-phase Luna^® C18(2) column and a mobile phase consisting of 75% acetonitrile and 0.1% formic acid in water. A PDA detector was used, and data were extracted at λ=220 nm. Principal component analysis of cannabis four varieties was performed. Results: The method was linear over the calibration range of 5-75 μg/mL with R²>0.999 for all cannabinoids. This method was sensitive and gave good baseline separation of all examined cannabinoids with limits of detection ranging between 0.2 and 1.6 μg/mL and limits of quantification ranging between 0.6 and 4.8 μg/mL. The average recoveries for all cannabinoids were between 81% and 104%. The measured repeatability and intermediate precisions (% relative standard deviation) in all varieties ranged from 0.35% to 9.84% and 1.11% to 5.26%, respectively. Conclusions: The proposed method is sensitive, selective, reproducible, and accurate. It can be applied for the simultaneous determination of these cannabinoids in the C. sativa biomass and cannabis-derived marketed products.

2024-04-26·Journal of natural products

Phytochemical Characterization and TRPA1/TRPM8 Modulation Profile of the Cannabigerol-Rich Cannabis sativa L. Chemotype IV

Article

作者: Arnoldi, Lolita ; Pagni, Luca ; Vitale, Rosa Maria ; Benetti, Emanuele ; Taglialatela-Scafati, Orazio ; Chianese, Giuseppina ; De Petrocellis, Luciano ; Gargiulo, Ernesto ; Moriello, Aniello Schiano

The first detailed phytochemical analysis of the cannabigerol (CBG)-rich chemotype IV of Cannabis sativa L. resulted in the isolation of the expected cannabigerolic acid/cannabigerol (CBGA/CBG) and cannabidiolic acid/cannabidiol (CBDA/CBD) and of nine new phytocannabinoids (5-13), which were fully characterized by HR-ESIMS and 1D and 2D NMR. These included mono- or dihydroxylated CBGA/CBG analogues, a congener with a truncated side chain (10), cyclocannabigerol B (11), and the CBD derivatives named cannabifuranols (12 and 13). Cyclocannabigerol B and cannabifuranols are characterized by a novel phytocannabinoid structural architecture. The isolated phytocannabinoids were assayed on the receptor channels TRPA1 and TRPM8, unveiling a potent dual TRPA1 agonist/TRPM8 antagonist profile for compounds 6, 7, and 14. Chiral separation of the two enantiomers of 5 resulted in the discovery of a synergistic effect of the two enantiomers on TRPA1.

2024-02-01·Biotechnology journal

Engineering cannabinoid production in Saccharomyces cerevisiae

Article

作者: Kayser, Oliver ; Schmidt, Christina ; Aras, Marco

Abstract:

Phytocannabinoids are natural products with highly interesting pharmacological properties mainly produced by plants. The production of cannabinoids in a heterologous host system has gained interest in recent years as a promising alternative to production from plant material. However, the systems reported so far do not achieve industrially relevant titers, highlighting the need for alternative systems. Here, we show the production of the cannabinoids cannabigerolic acid and cannabigerol from glucose and hexanoic acid in a heterologous yeast system using the aromatic prenyltransferase NphB from Streptomyces sp. strain CL190. The production was significantly increased by introducing a fusion protein consisting of ERG20WW and NphB. Furthermore, we improved the production of the precursor olivetolic acid to a titer of 56 mg L−1. The implementation of the cannabinoid synthase genes enabled the production of Δ9‐tetrahydrocannabinolic acid, cannabidiolic acid as well as cannabichromenic acid, where the heterologous biosynthesis of cannabichromenic acid in a yeast system was demonstrated for the first time. In addition, we found that the product spectrum of the cannabinoid synthases localized to the vacuoles of the yeast cells was highly dependent on extracellular pH, allowing for easy manipulation. Finally, using a fed‐batch approach, we showed cannabigerolic acid and olivetolic acid titers of up to 18.2 mg L−1 and 117 mg L−1, respectively.

项与 Cannabidivarin/Cannabigerolic acid 相关的新闻（医药）

2024-02-05

·BioSpace

Avicanna Announces Supply and Licensing Agreement with Multinational Pharmaceutical Company

Exclusive supply agreement for two of Avicanna’s proprietary topical products in the European region Right of first refusal agreement for the Avicanna’s SEDDs capsules in the European region TORONTO, Feb. 05, 2024 (GLOBE NEWSWIRE) -- Avicanna Inc. (“Avicanna” or the “Company) (TSX: AVCN) (OTCQX: AVCNF) (FSE: 0NN) a biopharmaceutical company focused on the development, manufacturing, and commercialization of plant-derived cannabinoid-based products is pleased to announce an exclusive supply agreement for two of the Company’s proprietary topical products with a multinational pharmaceutical company (“Pharma”). “We look forward to expanding our proprietary topical products into the European region and to be doing so through the utilization of our own international infrastructure for manufacturing. We are confident that through this strategic relationship and the Pharma’s established commercial infrastructure, we can facilitate the expansion of our proprietary products into several international markets,” stated Aras Azadian, CEO. Pharma manufactures and markets a wide range of pharmaceuticals across 4 continents and has established commercial infrastructure in the European region that will be utilized for the initial launch of the selected products. Pharma has committed to launch the initial products in 6 European countries during 2024 with expectations of expanding throughout the region shortly after. Avicanna will be earning licensing fees associated to specific milestones and the parties have also agreed to specific minimum order quantities and efforts for Pharma to maintain the exclusivity. The exclusive supply agreement is for the Company’s proprietary topical products that have been commercialized in the Canadian market under the RHO Phyto brand across several medical cannabis platforms including MyMedi.ca. Products Selected: The Ultra-CBD cream is a 3% CBD localized cream developed to target dermatology conditions. The cream is enrolled in previously announced observational real world evidence clinical trial with the Hospital for Sick Children related to Epidermolysis Bullosa. The CBG Transdermal Gel is a 2% CBD and 0.5% CBG gel developed to target local inflammatory and pain conditions. The gel is enrolled in previously announced observational real world evidence clinical trial on musculoskeletal pain and inflammation. The products have completed dossiers and will be registered and commercialized under applicable cosmetics legislation providing a route to market with the expected launch during the first half of 2024. The products will be manufactured using the Company’s Colombian operations while utilizing Avicanna’s own source of cannabinoids from majority owned subsidiary, Santa Marta Golden Hemp S.A.S. Additionally, the two companies have entered into a separate right of first refusal agreement related to the Company’s SEDDS technology capsules for the same region. About Avicanna Inc. Avicanna is a commercial-stage international biopharmaceutical company focused on the advancement and commercialization of evidence-based cannabinoid-based products for the global medical and pharmaceutical market segments. Avicanna has an established scientific platform including R&D and clinical development that has led to the commercialization of more than thirty products across various market segments: Medical Cannabis & Wellness Products (RHO Phyto™): The formulary offers a diverse range of proprietary formulations including oral, sublingual, topical, and transdermal deliveries with varying ratios of cannabinoids and is supported with ongoing patient, and medical community education. RHO Phyto has been established as a leading medical brand in Canada and is currently available nationwide to patients across several medical channels and continues to expand into new international markets. Pharmaceutical Preparations and Pipeline: Leveraging Avicanna’s scientific platform, vertical integration, and real-world evidence, Avicanna has developed an extensive a pipeline of patent-pending drug candidates that are indication-specific and in various stages of clinical development and commercialization. These cannabinoid-based drug candidates look to address unmet medical needs in the areas of dermatology, chronic pain, and various neurological disorders. Avicanna’s first pharmaceutical preparation (Trunerox™) is in the drug registration stage in South America. About MyMedi.ca MyMedi.ca is a medical cannabis care platform formed with the aim to better serve medical cannabis patients’ needs and enhance the patient journey. MyMedi.ca is operated by Northern Green Canada Inc., and features a diverse portfolio of products and pharmacist-led patient support programs. MyMedi.ca also provides specialty services to distinct patient groups such as veterans and collaborates with public and private providers for adjudication and reimbursement. MyMedi.ca provides educational resources to facilitate the incorporation of medical cannabis into health care regimens.  SOURCE Avicanna Inc. Stay Connected For more information about Avicanna, visit our website, contact Ivana Maric by email at info@avicanna.com or follow us on social media on LinkedIn, Twitter, Facebook, or Instagram. The Company posts updates through videos from the Company YouTube channel. Cautionary Note Regarding Forward-Looking Information and Statements This news release contains “forward-looking information” within the meaning of applicable securities laws. Forward-looking information contained in this news release may be identified using words such as, “may”, “would”, “could”, “will”, “likely”, “expect”, “anticipate”, “believe, “intend”, “plan”, “forecast”, “project”, “estimate”, “outlook” and other similar expressions. Although the Company believes that the expectations and assumptions on which such forward looking information is based are reasonable, undue reliance should not be placed on the forward-looking information because the Company can give no assurance that they will prove to be correct. Actual results and developments may differ materially from those contemplated by these statements. Forward-looking information is subject to a variety of risks and uncertainties that could cause actual events or results to differ materially from those projected in the forward-looking information. Such risks and uncertainties include but are not limited to current and future market conditions, including the market price of the common shares of the Company, and the risk factors set out in the Company’s annual information form dated March 31, 2023 filed with the Canadian securities regulators and available under the Company’s pro SEDAR at The statements in this news release are made as of the date of this release. The Company disclaims any intent or obligation to update any forward-looking information, whether as a result of new information, future events or results or otherwise, other than as required by applicable securities laws.

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2022-10-25

·BioSpace

BioHarvest Introduces its 1st Cannabis Breakthrough Composition with Major Medical and Commercial Implications

BioHarvest demonstrates unprecedented Cannabinoids tuning and elicitation capabilities (12X increase versus original plant) using its proprietary Bio-Plant CELLicitation™ platform technology Contains high amounts of minor Cannabinoids such as THCV (2.5%) and CBDV (4.4%) providing unique medical and commercial benefits The Company plans to reveal additional information related to its high THC Cannabis product line by year end Vancouver, British Columbia and Rehovot, Israel--(News - October 25, 2022) - BioHarvest Sciences Inc. (CSE: BHSC) (OTCQB: CNVCF) (FSE: 8MV) ("BioHarvest" or "the Company") reveals today the detailed analysis (tabled below) of the unique composition of one of its Bio CELLicitation™ based Cannabis products that were grown from a CBD Hemp plant. The analysis is derived from using industry standard HPLC measurements conducted by an independent third-party analytical laboratory which is ISO17025 cGMP accredited and is certified by the Israeli Ministry of Health. To view an enhanced version of this graphic, please visit: In addition to the Cannabinoids described in the table above, the β-caryophyllene, Beta-panasinsene and Selina terpenes were present in the composition. Dr. Christopher D'Adamo, Director, Center for Integrated Medicine at the University of Maryland, School of Medicine said "The medical establishment has been eyeing the potential of full spectrum Cannabis to address many chronic health indications in need of better treatment options. These achievements by BioHarvest in naturally eliciting important minor Cannabinoids to significant biologically active levels, combined with high levels of major Cannabinoids, all produced with high level of consistency represent a major breakthrough towards the development of efficient Cannabis-based botanical drugs". Unique scientific, medicinal, and commercial features of this composition: • Ground-breaking Science - Increasing the total Cannabinoids from 3% in the original plant flower to 36% and increasing THC from 0.09% to 7.5% in the final product (83X) demonstrate the power of BHSC's Bio-Plant CELLicitation™ technology to control the Cannabinoids levels and ratios in a full spectrum composition. In addition, naturally eliciting rare minor cannabinoids such as CBDV (88X) and THCV (249X) to significant biological active levels in the same composition with high level of major Cannabinoids is unprecedented. • Medical Impact - Unique composition of significant amounts of major and minor Cannabinoids, in a full spectrum form, paves the road for multiple Cannabis-based therapeutic solutions targeting key chronic indications such as pain management, anxiety, sleep disorder and ADHD. • Commercial Implications - The ability to start from a CBD Hemp plant and control the THC levels in the final composition would allow BioHarvest to sell unique Hemp-based non-synthetic therapeutic products (including distillates) on a federally legal base in the US. The sales & marketing of such products will take advantage of the already established "Direct to Consumer" commercial platform successfully employed by BioHarvest for its VINIA® product. BioHarvest can also target a wider range of health and wellness applications with unique products that combine its Polyphenols-based (VINIA®, olives and pomegranate) compounds with the Hemp-based compositions. "This rich Cannabinoids composition is unprecedented, and the wealth of features described above opens the door for many lucrative commercial and medical applications", said Ilan Sobel, CEO, and added "the ability to produce unique Cannabis and Hemp based compositions gives us tremendous flexibility to decide which markets to pursue, what would be the optimal products offerings and partnerships. In addition, the high level of Cannabinoids, combined with our unique cost advantage opens the door for the production of distillates and isolates of specific cannabinoids resulting in multiple levers to optimize revenue and profitability from this vertical". Dr. Brian Cornblatt, CMO, who leads BioHarvest Sciences' product supportive clinical trial efforts shared "The ability for us to create novel compositions with vast intellectual property opportunities is exciting. The clinical trial potential using these compositions is endless and we are going to focus our efforts on bringing to the world safe, effective, consistent, and easily accessible solutions for, in time, many of the major health challenges that we now face". Q3 Shareholder Update October 25, 11am PST | 2PM EST This composition breakthrough will be discussed in detail at today's live Shareholder Update, and all shareholder partners, investors, media, and members of the scientific community are invited to register here: . The presentation will be approximately 45 minutes, followed by a live question and answer session. All registrants will receive a recording of the session, and any questions regarding the Company or the Q3 2022 Shareholder Update can be sent to info@bioharvest.com. About BioHarvest Sciences Inc. BioHarvest Sciences Inc. (CSE: BHSC) is a fast-growing Biotech firm listed on the Canadian Securities Exchange. BioHarvest has developed a patented bio-cell growth platform technology capable of growing the active and beneficial ingredients in fruit and plants, at industrial scale, without the need to grow the plant itself. This technology is economical, ensures consistency, and avoids the negative environmental impacts associated with traditional agriculture. BioHarvest is currently focused on nutraceuticals and the medicinal cannabis markets. Visit: BioHarvest Sciences Inc. Ilan Sobel, Chief Executive Officer For further information, please contact: Dave Ryan, VP Investor Relations & Director Phone: 1 (604) 622-1186 Email: dave@bioharvest.com Twitter: Facebook: LinkedIn: YouTube: Forward-Looking Statements Information set forth in this news release includes forward-looking statements that are based on management's current estimates, beliefs, intentions, and expectations, and are subject to a number of risks and uncertainties that could cause actual results to differ materially from those described in the forward-looking statements. There is no assurance that strong sales metrics experienced to date will result in future demand or that proposed additional marketing expenditures will result in increased sales. Markets for nutraceuticals are unpredictable and subject to changes in consumer tastes and trends as well as economic factors beyond our control. Delays and cost overruns may result in delays achieving our objectives obtaining market acceptance, and regulatory approvals for geographic expansion is subject to risk and cannot be guaranteed. There is no assurance of commercial availability of our Cannabis product in 2022 or that the Company achieves the conversion of the two tons VINIA® facility to Cannabis production in 2022. These things are subject to construction and approval delays and uncertainties that may be beyond the control of BioHarvest. Projected sales of Cannabis will require the Company to obtain production and/or export licensing which cannot be assured. There is no assurance that the company will develop medical solutions targeting key indicators such as ADHD, pain management and anxiety. Marketing products with such claims would require FDA approval in the US and similar approvals in other jurisdictions which would require a lengthy and expensive approval process including clinical trials the outcome of which would be uncertain and cannot be assured. Although the Farm Act has removed prohibitions on the sale of CBD from hemp products there is no assurance the company will be able to successfully market such products nationwide which would require significant marketing expenditures and customer acceptance that is uncertain and cannot be assured All forward-looking statements are inherently uncertain and actual results may be affected by a number of material factors beyond our control. Readers should not place undue reliance on forward-looking statements. BHSC does not intend to update forward-looking statement disclosures other than through our regular management discussion and analysis disclosures. Neither the Canadian Securities Exchange nor its Regulation Services Provider accept responsibility for the adequacy or accuracy of this release. To view the source version of this press release, please visit

2022-06-14

·PRNewswire

Open Book Extracts & Biopharmaceutical Research Company Establish Research & Development Collaboration

BRC's DEA registration allows Open Book Extracts and BRC to conduct formulation efficacy research across the full range of cannabinoids. ROXBORO, N.C., June 14, 2022 /PRNewswire/ -- Open Book Extracts (OBX), an NSF-certified manufacturer and distributor of the industry's most innovative and highest quality cannabinoid ingredients and finished products, today announces a collaboration with Biopharmaceutical Research Company (BRC). Under the terms of the collaboration, OBX will leverage BRC's research platforms, in order to develop research-backed formulations and products including Delta-9 THC. From preclinical and first-in-human (FIH) dosage forms to optimization of formulations for late-stage development and market following clinical evaluation, OBX will work closely with BRC to develop the most appropriate formulation based on the physicochemical and biopharmaceutics properties of the cannabinoids of interest, the intended route of administration and the phase of development. The partnership with BRC also supports the study of Delta-9 THC products and formulations, allowing OBX to identify the phase appropriate, optimal products for formulations including Delta-9 THC. "Current political and economic situations have created non-science-based products that are not serving today's consumers, and are not designed to fill the research gaps we desperately need to fill to legitimize the emerging anecdotal evidence," said Dave Neundorfer, OBX CEO. "Companies that base their brands on the research-backed formulations guided by science and develop corresponding products will rule global market share, and recreate how we choose to find therapeutic relief along with relaxation and stimulation. We are excited to expand our research capabilities through our collaboration with BRC, in particular being able to add Delta-9 THC as a cannabinoid of interest for our formulation research." With a 76,000 sf. research and production facility near Durham, North Carolina, OBX has developed proven methods to efficiently manufacture a broad range of cannabinoids from hemp and natural sources, including CBD, CBN, CBC, CBG, CBGa, CBT, CBDa, CBDv, and THCv. OBX offers concept-to-market formulation and product development and manufacturing services, leveraging leading water soluble technology and unique delivery mechanisms to help its clients bring to market a wide range of finished goods, from core softgels, capsules, and gummies, to orally dissolving tablets, tongue strips, and aerosol sprays. "BRC is pleased to partner with OBX, joining forces to further build the body of evidence to support the cannabis industry," shares George Hodgin, BRC CEO. "It is time we investigate the real science, and develop products for brands that take our culture to the next step. It will take a concerted effort. Developing appealing and effective cannabis-based products requires a multidisciplinary approach in food and pharma chemistry. BRC is a one-stop-shop for developing, modifying and improving these new products, and we're excited to work with OBX to help bring novel, well-studied, effective products to consumers everywhere." For those interested in learning more about OBX's products and services, or how OBX and BRC can support your research and development needs, please reach out directly to Nicole Brown, Chief Innovation Officer, at [email protected]. About Open Book Extracts Headquartered in Roxboro, N.C., Open Book Extracts is an NSF-certified manufacturer of premium cannabinoid products, aiming to be the industry's true north by delivering premium products, exceptional service, and industry-leading transparency. With control of the entire supply chain, a state-of-the-art extraction campus near North Carolina's Research Triangle, proprietary refinement and conversion methods backed by a growing IP portfolio, and a team of PhD chemists and seasoned business leaders, OBX is the trusted partner for global brands seeking to enter the marketplace. About Biopharmaceutical Research Company (BRC) Biopharmaceutical Research Company (BRC) was founded in 2017 to serve the needs of the pharmaceutical, research and biotech communities. In addition to our standard panels, our laboratory conducts specialty, tailored research projects for clients worldwide. Contact: Nicole Brown 9146450898 [email protected] SOURCE Open Book Extracts

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