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    Determination of 11 Cannabinoids in Biomass and Extracts of Different Varieties of Cannabis Using High-Performance Liquid Chromatography.
    J AOAC Int 2015 Nov-Dec;98(6):1523-8
    ElSohly Laboratories, Inc., 5 Industrial Park Dr, Oxford, MS 38655, USA.
    An HPLC single-laboratory validation was performed for the detection and quantification of the 11 major cannabinoids in most cannabis varieties, namely, cannabidiolic acid (CBDA), cannabigerolic acid (CBGA), cannabigerol (CBG), cannabidiol (CBD), tetrahydrocannabivarin (THCV), cannabinol (CBN), Δ9-trans-tetrahydrocannabinol (Δ9-THC), Δ8-trans-tetrahydrocannabinol (Δ8-THC), cannabicyclol (CBL), cannabichromene (CBC), and Δ9-tetrahydrocannabinolic acid-A (THCAA). The analysis was carried out on the biomass and extracts of these varieties. Methanol-chloroform (9:1, v/v) was used for extraction, 4-androstene-3,17-dione was used as the internal standard, and separation was achieved in 22. Read More

    Efficient and novel one-pot synthesis of polycycles bearing cyclols by FeCl3-promoted [2 + 2] cycloaddition: application to cannabicyclol, cannabicyclovarin, and ranhuadujuanine A.
    Org Biomol Chem 2014 Feb;12(8):1250-7
    School of Chemical Engineering, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
    Simple and facile synthetic routes for the preparation of biologically interesting cyclol bearing polycycles were developed using FeCl3-promoted [2 + 2] cycloaddition from readily available benzopyrans possessing a variety of substituents. As examples of this methodology, one-step syntheses of cannabicyclol, cannabicyclovarin, and ranhuadujuanine A were accomplished in good yield. Read More

    Total syntheses of cannabicyclol, clusiacyclol A and B, iso-eriobrucinol A and B, and eriobrucinol.
    Org Lett 2013 Jun 3;15(12):3130-3. Epub 2013 Jun 3.
    Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53705, United States, and School of Pharmaceutical Science and Technology, Tianjin University , Tianjin, 300072, P. R. China.
    Total syntheses of a series of chromane natural products that contain a cyclobutane ring are described. A unified theme in the strategy employed for all these syntheses is an oxa-[3 + 3] annulation for constructing the chromane nucleus and a stepwise cationic [2 + 2] cycloaddition for the cyclobutane formation. More importantly, the two reactions could be rendered in tandem, thereby providing an expeditious approach to this family of natural products. Read More

    New cannabinoid-like chromane and chromene derivatives from Rhododendron anthopogonoides.
    Chem Pharm Bull (Tokyo) 2011 ;59(11):1409-12
    School of Pharmacy, Nihon University, Funabashi, Chiba 274–8555, Japan.
    Two new cannabinoid-like chromane and chromene derivatives named anthopogocyclolic acid (1) and anthopogochromenic acid (2) and five related compounds (3-7) which are known as synthetic analogues of cannabinoids: cannabichromene (CBC) type, cannabicyclol (CBL) type, and cannabicitran (CBT) type, have been isolated together with geranyl orsellinic acid (8) from the Chinese medicinal plant Rhododendron anthopogonoides. Their structures were elucidated based on spectroscopic and chemical evidence. The absolute configuration of the asymmetric carbons at C-2 of 1-7 was determined to be S from their circular dichroism (CD) spectra. Read More

    Chemical constituents of malagasy liverworts, part V: prenyl bibenzyls and clerodane diterpenoids with nitric oxide inhibitory activity from Radula appressa and Thysananthus spathulistipus.
    Chem Pharm Bull (Tokyo) 2006 Jul;54(7):1046-9
    Faculty of Pharmaceutical Sciences, Tokushima Bunri University; Yamashiro-cho, Tokushima 770-8514, Japan.
    3Beta,4beta:15,16-diepoxy-13(16),14-clerodadiene (1) and a new clerodane diterpenoid designated thysaspathone (2) were isolated from the liverwort Thysananthus spathulistipus, while Radula appressa produced radulannin A (3), radulannin L (4), 2-geranyl-3,5-dihydroxybibenzyl (5), 2(S)-2-methyl-2-(4-methyl-3-pentenyl)-7-hydroxy-5-(2-phenylethyl) chromene (o-cannabichromene) (6), 6-hydroxy-4-(2-phenylethyl) benzofuran (7), and o-cannabicyclol (8). All of the isolated compounds inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and the greatest inhibition was attributed to compound 5, with an IC50 value of 4. Read More

    Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L.
    Phytochem Anal 2005 Jan-Feb;16(1):45-8
    National Center for Natural Products Research, University of Mississippi, University, Mississippi 38677-1848, USA.
    Chemical investigation of the pollen grain collected from male plants of Cannabis sativa L. resulted in the isolation for the first time of two flavonol glycosides from the methanol extract, and the identification of 16 cannabinoids in the hexane extract. The two glycosides were identified as kaempferol 3-O-sophoroside and quercetin 3-O-sophoroside by spectroscopic methods including high-field two-dimensional NMR experiments. Read More

    Prostaglandins and cannabis XIV. Tolerance to the stimulatory actions of cannabinoids on arachidonate metabolism.
    J Pharmacol Exp Ther 1985 Oct;235(1):87-91
    The stimulation of prostaglandin E2 synthesis by delta 1-tetrahydrocannabinol in cultured cells is rapidly diminished by successive exposures to the drug at 24-hr intervals. Cannabidiol and cannabicyclol, two other constituents of cannabis, also displayed this in vitro tolerance effect. The phenomenon could, in addition, be observed by measuring the release of arachidonic acid from these cells, suggesting that the site of action of the cannabinoids is at one or more of the lipases that are believed to control prostaglandin synthesis under most conditions. Read More

    Effects of delta 1-tetrahydrocannabinol on cyclic AMP in cultured human diploid fibroblasts.
    J Cyclic Nucleotide Res 1979 ;5(4):303-13
    (-)-trans-delta 1-Tetrahydrocannabinol (delta 1-THC) antagonized the cyclic AMP responses of WI-38 fibroblasts to both prostaglandin E1 (PGE1) and catecholamines. Both cellular cyclic AMP accumulation and cyclic AMP escape to the incubation medium were reduced, but the reduction of escape was much more dramatic at all concentrations of the drug. Conversely, long term incubations of cells with delta 1-THC alone resulted in substantial accumulations of cyclic AMP in the incubation medium. Read More

    Mass spectrometry of cannabinoids.
    J Pharm Sci 1977 Oct;66(10):1444-50
    The mechanism of fragmentation of cannabinoids to fragments m/e 314, 299, 271, 258, 246, 243, and 231 is given. Cannabidiol cannabinoidiol, cannabinol, delta6- and delta1-tetrahydrocannabinol, cannabichromene, cannabicyclol, derivatives with pentyl, propyl, and methyl side chains, their methyl ethers, and cis-trans and ortho-para isomers were analyzed by GLC-mass spectrometry using different energies for fragmentation during GLC elution. The following mechanism was distinguished: loss of a methyl radical, ring closure and rotation, McLafferty rearrangement, retro Diels-Alder, internal protonation, isomerization and internal bond formation, and one-step fragmentation to m/e 231. Read More

    Effects of cannabinoids on macromolecular synthesis and replication of cultured lymphocytes.
    Fed Proc 1977 Apr;36(5):1748-52
    The lymphocyte response to phytohemagglutinin (PHA) as measured by [13H]thymidine incorporation is equally inhibited by 10(-5) to 10(-4) M concentrations of delta8, and delta9-tetrahydrocannabinol (THC), their 11-hydroxymetabolites, cannabidiol, cannabinol, cannabichromene, cannabicyclol. A similar inhibiting effect is produced by olivetol, which has the structure of the C ring common to all of these cannabinoids and their metabolites that accumulate in tissues. THC inhibits intracellular and intramolecular incorporation of thymidine, uridine, and leucine. Read More

    The inhibition of DNA synthesis by cannabinoids.
    Cancer Res 1976 Jan;36(1):95-100
    Several of the cannabinoids found in marihuana have been shown to inhibit tumor growth and increase the life-span of mice bearing the Lewis lung adenocarcinoma. When trypsin-dispersed isolated Lewis lung cells are incubated in vitro, they maintain their capacity to carry out macromolecular synthesis (RNA, DNA, protein). This process can be inhibited by cytosine arabinoside, actinomycin D, or methyl-1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea, whereas cyclophosphamide, an agent that must be bioactivated, was inactive. Read More

    Constituents of Cannabis sativa L. VIII: Possible biological application of a new method to separate cannabidiol and cannabichromene.
    J Pharm Sci 1975 May;64(5):810-4
    Synthetic and naturally occurring cannabidiol and cannabichromene were distinctly separated without derivation by GLC using a 6% OV-1 column; an artifact of cannabichromene, cannabicyclol, was separated from (minus)-delta9-trans-tetrahydrocanna-bivarin. This procedure is versatile and applicable for the quantitation of Cannabis containing both cannabidiol and cannabichromene. Biological interaction among (minus)-delta9-trans-tetrhydrocanabinol, cannabichromene, and other cannabinoids in natural Cannabis preparations can now be studied. Read More

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