O-Methyl Phytocannabinoids: Semi-synthesis, Analysis in Cannabis Flowerheads, and Biological Activity
| Autor: | Diego Caprioglio, Orazio Taglialatela-Scafati, Eduardo Muñoz, Stefano Valera, Gianna Allegrone, Federica Pollastro, Giovanni Appendino, Annalisa Lopatriello, Juan A. Collado |
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| Přispěvatelé: | Caprioglio, D., Allegrone, G., Pollastro, F., Valera, S., Lopatriello, A., Collado, J. A., Munoz, E., Appendino, G., Taglialatela-Scafati, O. |
| Rok vydání: | 2019 |
| Předmět: |
Cannabidivarin
Magnetic Resonance Spectroscopy Stereochemistry Cannabigerol Peroxisome Proliferator-Activated Receptors Cannabaceae Pharmaceutical Science Flowers PPAR 01 natural sciences Analytical Chemistry HEK293 Cell phytocannabinoid Drug Discovery medicine Humans Cannabi meroterpenoid Cannabinoid Cannabis Pharmacology Molecular Structure biology Chemotype Cannabinoids 010405 organic chemistry Chemistry Organic Chemistry O-methylation Biological activity Cannabis sativa Peroxisome biology.organism_classification 0104 chemical sciences 010404 medicinal & biomolecular chemistry HEK293 Cells Complementary and alternative medicine Flower Molecular Medicine Cannabidiol Human medicine.drug |
| Zdroj: | Planta Medica. 85:981-986 |
| ISSN: | 1439-0221 0032-0943 |
| DOI: | 10.1055/a-0883-5383 |
| Popis: | A general protocol for the selective mono-O-methylation of resorcinyl phytocannabinoids was developed. The availability of semisynthetic monomethyl analogues of cannabigerol, cannabidiol, and cannabidivarin (1a–3a, respectively) made it possible to quantify these minor phytocannabinoids in about 40 different chemotypes of fiber hemp. No chemotype significantly accumulated mono-O-methyl cannabidiol (2b) or its lower homologue (3b), while at least three chemotypes containing consistent amounts (≥ 400 mg/kg) of O-methylcannabigerol (1b) were identified. O-Methylation of alkyl phytocannabinoids (1b–3b) does not significantly change the activity on peroxisome proliferator-activated receptors in contrast to what was reported for phenethyl analogues. |
| Databáze: | OpenAIRE |
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