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Official websites use. Share sensitive information only on official, secure websites. To whom correspondence should be addressed. CB-1 receptor assay indicated that the esters, as well as the parent acids, are not active. The family Cannabaceae is currently recognized as containing only one genus, namely, Cannabis , which includes only one highly variable species: Cannabis sativa L. Other previously reported species include Cannabis indica Lam. Plants considered to have belonged to these species are now recognized as varieties of C. The chemotypes of C. Cannabis is very complex in its chemistry due to the vast number of its constituents and their possible interaction with one another. The compounds reported include many natural product classes, e. The medicinal properties of Cannabis have been much debated from scientific and political points of view, and the subject has lost and gained interest over the years. Features of this system include that cannabinoids act through receptors, that there are at least two types of receptors CB1 21 and CB2 22 , and that there are endogenous cannabinoid receptor agonists and antagonists ligands. The CB1 receptor, uniquely recognized by cannabinoids, is found in brain and peripheral tissue of the central nervous system CNS , 23 while the CB2 receptor is primarily found outside the CNS in tissues associated with immune function. We herein report the isolation and structure elucidation of 11 new esters from a high-potency variety of cannabis. All isolated compounds were evaluated for antimicrobial and antimalarial activity, as well as CB-1 receptor binding. The hexanes extract was subjected to vacuum liquid chromatography VLC on flash silica gel. Fractions were combined according to their TLC profiles and chromatographed using flash silica gel eluting with hexanes. This yielded 11 new esters 1 — The spectroscopic data of 7 and 11 were in accordance with that of CBGA. Detailed analyses of the spectroscopic data indicated that 7 and 11 were CBGA esters. The alcohol was identified as a terpineol isomer via a library search NIST and was subsequently found to be 4-terpineol through retention time comparison with an authentic sample and by comparison with published mass spectra. On the basis of these observations, 8 was assigned as 4-terpenyl cannabinolate. In identifying the mono- and sesquiterpene moieties of these esters, an extensive search was undertaken to determine whether these terpenols have previously been found in Cannabis. This was problematic, since in most cases only a general identification was made. Although the cannabis plant has been studied extensively over the past four decades, this is, to the best of our knowledge, the first phytochemical analysis of a high-potency material, 25 and the first newly isolated cannabinoids since , 7 indicating that the high-potency nature of the plant material could open the field to the isolation of other new metabolites. Compound 8 showed moderate antimicrobial activity against C. CB-1 receptor binding assay indicated that the esters, as well as the parent acids, are not active. IR spectra were recorded on a Bruker Tensor 27 spectrophotometer. Optical rotations were measured at ambient temperature using a Rudolph Research Analytical Autopol IV automatic polarimeter. Visualization was accomplished by spraying with Fast Blue B salt 0. Helium was used as the carrier gas at a constant pressure of 20 psi. Plants were grown from high-potency Mexican C. The plant material 9. The hexanes extract 0. Dried samples ca. After cooling to room temperature, CH 2 Cl 2 0. HPLC chromatograms of isolated compounds. GC-MS data of isolated compounds. This section collects any data citations, data availability statements, or supplementary materials included in this article. As a library, NLM provides access to scientific literature. J Nat Prod. Published in final edited form as: J Nat Prod. Find articles by Safwat A Ahmed. Find articles by Samir A Ross. Find articles by Desmond Slade. Find articles by Mohamed M Radwan. Find articles by Fazila Zulfiqar. Find articles by Mahmoud A ElSohly. Issue date Apr. PMC Copyright notice. The publisher's version of this article is available at J Nat Prod. Open in a new tab. Similar articles. Add to Collections. Create a new collection. Add to an existing collection. Choose a collection Unable to load your collection due to an error Please try again. Add Cancel.